MiMeDB: Showing metabocard for Methylmalonyl-CoA (MMDBc0031995)

Microbial

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:57:55 UTC

Update Date

2025-11-05 17:13:01 UTC

Metabolite ID

MMDBc0031995

Metabolite Identification

Common Name

Methylmalonyl-CoA

Description

Methylmalonyl-CoA is a key metabolite in the class of acyl-CoA derivatives, specifically involved in the metabolism of branched-chain amino acids and odd-chain fatty acids. Its chemical structure features a malonyl moiety attached to coenzyme A, facilitating its role in various biochemical pathways. Methylmalonyl-CoA is primarily involved in the catabolism of propionate, where it is converted into succinyl-CoA by the enzyme methylmalonyl-CoA mutase, a process that requires vitamin B12 as a cofactor (PMID:40790789 ). Additionally, it plays a role in lipid synthesis, with pathways stimulated by methylmalonyl-CoA influencing growth and metabolism in certain mutants (PMID:41040295 ). The compound is also implicated in metabolic stress responses, as seen in kidney damage linked to methylmalonyl-CoA mutase deficiency (PMID:40998969 ). Furthermore, it is involved in maintaining energy balance under hypoxic conditions by redirecting carbon flux through the methylmalonyl-CoA pathway (PMID:40871463 ). Overall, methylmalonyl-CoA serves as a crucial intermediate in multiple metabolic processes, highlighting its importance in both energy metabolism and the synthesis of vital biomolecules.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02231219012D          

 55 57  0  0  1  0            999 V2000
    0.3282    2.3631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4121    2.1625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9299    1.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6017    3.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6418    1.4514    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0357    2.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5754    2.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737    1.1195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3712    3.0450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4186    1.4514    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1896    0.8351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6556    2.1735    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2609    1.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6629    0.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015    0.9080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3704    2.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3047    1.1961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9246    2.3485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.9117    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4060    1.9073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3549    0.8934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6184    0.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6839    1.7577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6824    1.3602    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6824   -0.1787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6933    2.1078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4445    1.3748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6824   -1.7504    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8545   -1.7504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6860   -2.5782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4408   -1.7504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1398   -1.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4251   -1.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7067   -1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4251   -2.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4288   -0.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0429   -1.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7103   -0.5033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3282   -1.2982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0467   -2.5418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3865   -1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1013   -1.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8160   -1.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5345   -1.2872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8124   -2.5345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2492   -1.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9640   -1.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6787   -1.6958    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3935   -1.2799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1083   -1.6921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3899   -0.4522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8230   -1.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0973   -2.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5377   -1.6885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8157   -0.4485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  6  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8 14  2  0  0  0  0
 10 15  1  6  0  0  0
 12 16  1  1  0  0  0
 13 17  2  0  0  0  0
 13 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  2  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 34 37  1  0  0  0  0
 34 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  2  0  0  0  0
 50 52  1  0  0  0  0
 50 53  1  6  0  0  0
 52 54  1  0  0  0  0
 52 55  2  0  0  0  0
  7  9  1  0  0  0  0
 10 12  1  0  0  0  0
 14 17  1  0  0  0  0
M  END

HMDB0001269
     RDKit          3D
Methylmalonyl-CoA
 95 97  0  0  0  0  0  0  0  0999 V2000
   13.0444   -1.2484   -1.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2427   -1.9168    0.2262 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7527   -0.9503    1.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9701    0.2537    1.0352 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9674   -1.5160    2.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0630   -2.6641    0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1105   -3.9048    0.3935 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6633   -2.0313    1.5136 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7200   -0.3143    1.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5917    0.6078    0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3359    0.3759    0.0066 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0645    0.5269    0.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9686    0.8779    1.7873 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8489    0.2691   -0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6416    0.5024    0.6759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.2650   -0.0511 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738    0.4390    0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1902    0.7877    1.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8373    0.2416    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8461    0.1964    1.0284 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4535    1.4208   -0.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4560    1.5631   -1.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3821    2.6744   -0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0663    1.0952   -1.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3837    2.1271   -2.2350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9059    1.8051   -2.8619 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.1118    0.3390   -3.1267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0704    2.6769   -4.3097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1200    2.3388   -1.8194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3840    1.2059   -1.8404 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.1841    1.3029   -3.1226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7014   -0.3255   -1.7079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4324    1.4472   -0.5440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6874    0.2205    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6321    0.3753    1.2342 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8386    0.9036    0.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8121   -0.0564    0.9099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.7088    0.0165   -0.2269 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4158    0.2424   -1.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5419    0.2270   -2.2431 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5850   -0.0102   -1.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9501   -0.1281   -1.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4640    0.0130   -2.9632 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7198   -0.3740   -0.5753 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1844   -0.5010    0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8666   -0.3902    0.8962 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0454   -0.1400   -0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1284   -1.3999    1.0241 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8617   -2.3147    1.7717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8852   -1.0060    1.7939 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2336   -0.9135    3.1379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2522   -1.8921    4.1056 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.7942   -1.0666    5.2940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0988   -3.2228    4.7169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8873   -2.4047    3.2254 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4291   -0.2058   -1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5954   -1.7992   -1.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9596   -1.2017   -1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1027   -2.6577    0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3370   -0.9194    3.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8948   -0.0925    2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6633   -0.0543    2.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4468    0.6486    0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4833    1.6784    1.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4021    0.0785   -1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8808   -0.7865   -0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7977    0.9204   -1.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6944    1.5318    1.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7275   -0.1892    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4241   -0.0370   -1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7509   -0.6694   -0.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470    1.1205    1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4108    1.9932   -1.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6468    0.5783   -2.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0888    2.2926   -2.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7075    3.5736   -0.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3338    2.8767    0.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9845    2.6107    0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6751    1.0105   -0.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126    0.1202   -1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3956    3.3824   -4.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9895   -0.3530   -1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1333   -0.4511   -0.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7632   -0.2833    0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1159    0.9912    2.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4139    0.0875    1.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3878    0.4093   -1.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0345    0.5774   -3.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.3552   -0.4996   -3.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8226   -0.7007    1.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8934   -1.8544    0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8039   -2.2580    1.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0406   -1.6972    1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4543   -3.9650    4.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1443   -2.4532    3.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 30 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
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 37 48  1  0
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 48 50  1  0
 50 51  1  0
 51 52  1  0
 52 53  2  0
 52 54  1  0
 52 55  1  0
 50 35  1  0
 47 38  1  0
 47 41  1  0
  1 56  1  0
  1 57  1  0
  1 58  1  0
  2 59  1  6
  5 60  1  0
  9 61  1  0
  9 62  1  0
 10 63  1  0
 10 64  1  0
 11 65  1  0
 14 66  1  0
 14 67  1  0
 15 68  1  0
 15 69  1  0
 16 70  1  0
 19 71  1  0
 20 72  1  0
 22 73  1  0
 22 74  1  0
 22 75  1  0
 23 76  1  0
 23 77  1  0
 23 78  1  0
 24 79  1  0
 24 80  1  0
 28 81  1  0
 32 82  1  0
 34 83  1  0
 34 84  1  0
 35 85  1  1
 37 86  1  1
 39 87  1  0
 43 88  1  0
 43 89  1  0
 45 90  1  0
 48 91  1  6
 49 92  1  0
 50 93  1  1
 54 94  1  0
 55 95  1  0
M  END


  Mrv0541 02231219012D          

 55 57  0  0  1  0            999 V2000
    0.3282    2.3631    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4121    2.1625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9299    1.8854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6017    3.0815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6418    1.4514    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0357    2.6184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5754    2.3047    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9737    1.1195    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.3712    3.0450    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4186    1.4514    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1896    0.8351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6556    2.1735    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2609    1.9620    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6629    0.7731    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8015    0.9080    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3704    2.4032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3047    1.1961    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9246    2.3485    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111    0.9117    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4060    1.9073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3549    0.8934    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6184    0.1458    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6839    1.7577    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6824    1.3602    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6824   -0.1787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6933    2.1078    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4445    1.3748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6824   -1.7504    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8545   -1.7504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6860   -2.5782    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4408   -1.7504    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1398   -1.3347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4251   -1.7467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7067   -1.3310    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4251   -2.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4288   -0.9190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0429   -1.7140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7103   -0.5033    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3282   -1.2982    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0467   -2.5418    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3865   -1.7103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1013   -1.2945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8160   -1.7067    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5345   -1.2872    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.8124   -2.5345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2492   -1.6994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9640   -1.2836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6787   -1.6958    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3935   -1.2799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1083   -1.6921    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    5.3899   -0.4522    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8230   -1.2763    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0973   -2.5199    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5377   -1.6885    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8157   -0.4485    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  6  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8 14  2  0  0  0  0
 10 15  1  6  0  0  0
 12 16  1  1  0  0  0
 13 17  2  0  0  0  0
 13 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  2  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 34 37  1  0  0  0  0
 34 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  2  0  0  0  0
 50 52  1  0  0  0  0
 50 53  1  6  0  0  0
 52 54  1  0  0  0  0
 52 55  2  0  0  0  0
  7  9  1  0  0  0  0
 10 12  1  0  0  0  0
 14 17  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031995

> <DATABASE_NAME>
MIME

> <SMILES>
C[C@@H](C(O)=O)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

> <INCHI_IDENTIFIER>
InChI=1S/C25H40N7O19P3S/c1-12(23(37)38)24(39)55-7-6-27-14(33)4-5-28-21(36)18(35)25(2,3)9-48-54(45,46)51-53(43,44)47-8-13-17(50-52(40,41)42)16(34)22(49-13)32-11-31-15-19(26)29-10-30-20(15)32/h10-13,16-18,22,34-35H,4-9H2,1-3H3,(H,27,33)(H,28,36)(H,37,38)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t12-,13+,16+,17+,18?,22+/m0/s1

> <INCHI_KEY>
MZFOKIKEPGUZEN-PNEPRAIJSA-N

> <FORMULA>
C25H40N7O19P3S

> <MOLECULAR_WEIGHT>
867.607

> <EXACT_MASS>
867.131252359

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_AVERAGE_POLARIZABILITY>
75.35219926302744

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S)-3-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-2-methyl-3-oxopropanoic acid

> <ALOGPS_LOGP>
-0.60

> <JCHEM_LOGP>
-6.5444667387921704

> <ALOGPS_LOGS>
-2.39

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-5

> <JCHEM_PKA>
1.82941451824599

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8248176615517999

> <JCHEM_PKA_STRONGEST_BASIC>
4.974397514089584

> <JCHEM_POLAR_SURFACE_AREA>
400.9299999999999

> <JCHEM_REFRACTIVITY>
183.12660000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.57e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S)-3-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-2-methyl-3-oxopropanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0001269
     RDKit          3D
Methylmalonyl-CoA
 95 97  0  0  0  0  0  0  0  0999 V2000
   13.0444   -1.2484   -1.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2427   -1.9168    0.2262 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7527   -0.9503    1.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9701    0.2537    1.0352 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9674   -1.5160    2.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0630   -2.6641    0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1105   -3.9048    0.3935 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6633   -2.0313    1.5136 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7200   -0.3143    1.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5917    0.6078    0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3359    0.3759    0.0066 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0645    0.5269    0.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9686    0.8779    1.7873 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8489    0.2691   -0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6416    0.5024    0.6759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.2650   -0.0511 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738    0.4390    0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1902    0.7877    1.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8373    0.2416    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8461    0.1964    1.0284 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4535    1.4208   -0.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4560    1.5631   -1.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3821    2.6744   -0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0663    1.0952   -1.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3837    2.1271   -2.2350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9059    1.8051   -2.8619 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.1118    0.3390   -3.1267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0704    2.6769   -4.3097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1200    2.3388   -1.8194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3840    1.2059   -1.8404 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.1841    1.3029   -3.1226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7014   -0.3255   -1.7079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4324    1.4472   -0.5440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6874    0.2205    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6321    0.3753    1.2342 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8386    0.9036    0.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8121   -0.0564    0.9099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.7088    0.0165   -0.2269 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4158    0.2424   -1.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5419    0.2270   -2.2431 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5850   -0.0102   -1.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9501   -0.1281   -1.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4640    0.0130   -2.9632 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7198   -0.3740   -0.5753 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1844   -0.5010    0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8666   -0.3902    0.8962 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0454   -0.1400   -0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1284   -1.3999    1.0241 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8617   -2.3147    1.7717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8852   -1.0060    1.7939 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2336   -0.9135    3.1379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2522   -1.8921    4.1056 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.7942   -1.0666    5.2940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0988   -3.2228    4.7169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8873   -2.4047    3.2254 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4291   -0.2058   -1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5954   -1.7992   -1.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9596   -1.2017   -1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1027   -2.6577    0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3370   -0.9194    3.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8948   -0.0925    2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6633   -0.0543    2.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4468    0.6486    0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4833    1.6784    1.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4021    0.0785   -1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8808   -0.7865   -0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7977    0.9204   -1.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6944    1.5318    1.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7275   -0.1892    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4241   -0.0370   -1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7509   -0.6694   -0.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470    1.1205    1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4108    1.9932   -1.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6468    0.5783   -2.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0888    2.2926   -2.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7075    3.5736   -0.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3338    2.8767    0.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9845    2.6107    0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6751    1.0105   -0.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126    0.1202   -1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3956    3.3824   -4.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9895   -0.3530   -1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1333   -0.4511   -0.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7632   -0.2833    0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1159    0.9912    2.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4139    0.0875    1.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3878    0.4093   -1.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0345    0.5774   -3.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.3552   -0.4996   -3.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8226   -0.7007    1.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8934   -1.8544    0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8039   -2.2580    1.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0406   -1.6972    1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4543   -3.9650    4.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1443   -2.4532    3.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 30 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 42 44  1  0
 44 45  2  0
 45 46  1  0
 46 47  2  0
 37 48  1  0
 48 49  1  0
 48 50  1  0
 50 51  1  0
 51 52  1  0
 52 53  2  0
 52 54  1  0
 52 55  1  0
 50 35  1  0
 47 38  1  0
 47 41  1  0
  1 56  1  0
  1 57  1  0
  1 58  1  0
  2 59  1  6
  5 60  1  0
  9 61  1  0
  9 62  1  0
 10 63  1  0
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 14 66  1  0
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 19 71  1  0
 20 72  1  0
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 23 77  1  0
 23 78  1  0
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 28 81  1  0
 32 82  1  0
 34 83  1  0
 34 84  1  0
 35 85  1  1
 37 86  1  1
 39 87  1  0
 43 88  1  0
 43 89  1  0
 45 90  1  0
 48 91  1  6
 49 92  1  0
 50 93  1  1
 54 94  1  0
 55 95  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0       0.613   4.411   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -0.769   4.037   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.736   3.519   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.123   5.752   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.198   2.709   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -1.933   4.888   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.941   4.302   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0       1.818   2.090   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0       2.560   5.684   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -2.648   2.709   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.354   1.559   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -3.090   4.057   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.220   3.662   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.104   1.443   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -3.363   1.695   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -4.425   4.486   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0       4.302   2.233   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0       5.459   4.384   0.000  0.00  0.00           N+0
HETATM   19  P   UNK     0      -4.874   1.702   0.000  0.00  0.00           P+0
HETATM   20  O   UNK     0      -6.358   3.560   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -6.262   1.668   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -4.888   0.272   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -5.010   3.281   0.000  0.00  0.00           O+0
HETATM   24  P   UNK     0      -8.740   2.539   0.000  0.00  0.00           P+0
HETATM   25  O   UNK     0      -8.740  -0.334   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -8.761   3.935   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0     -10.163   2.566   0.000  0.00  0.00           O+0
HETATM   28  P   UNK     0      -8.740  -3.267   0.000  0.00  0.00           P+0
HETATM   29  O   UNK     0      -7.195  -3.267   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0      -8.747  -4.813   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -10.156  -3.267   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -5.861  -2.491   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -4.527  -3.261   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.186  -2.485   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -4.527  -4.806   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.534  -1.715   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -1.947  -3.199   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.193  -0.939   0.000  0.00  0.00           O+0
HETATM   39  N   UNK     0      -0.613  -2.423   0.000  0.00  0.00           N+0
HETATM   40  O   UNK     0      -1.954  -4.745   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       0.721  -3.193   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.056  -2.416   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       3.390  -3.186   0.000  0.00  0.00           C+0
HETATM   44  N   UNK     0       4.731  -2.403   0.000  0.00  0.00           N+0
HETATM   45  O   UNK     0       3.383  -4.731   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       6.065  -3.172   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       7.399  -2.396   0.000  0.00  0.00           C+0
HETATM   48  S   UNK     0       8.734  -3.165   0.000  0.00  0.00           S+0
HETATM   49  C   UNK     0      10.068  -2.389   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      11.402  -3.159   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      10.061  -0.844   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      12.736  -2.382   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      11.382  -4.704   0.000  0.00  0.00           C+0
HETATM   54  O   UNK     0      14.070  -3.152   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      12.723  -0.837   0.000  0.00  0.00           O+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   13    9                                                  
CONECT    8    3   14                                                       
CONECT    9    4    7                                                       
CONECT   10    5   15   12                                                  
CONECT   11    5                                                            
CONECT   12    6   16   10                                                  
CONECT   13    7   17   18                                                  
CONECT   14    8   17                                                       
CONECT   15   10   19                                                       
CONECT   16   12   20                                                       
CONECT   17   13   14                                                       
CONECT   18   13                                                            
CONECT   19   15   21   22   23                                             
CONECT   20   16   24                                                       
CONECT   21   19                                                            
CONECT   22   19                                                            
CONECT   23   19                                                            
CONECT   24   20   25   26   27                                             
CONECT   25   24   28                                                       
CONECT   26   24                                                            
CONECT   27   24                                                            
CONECT   28   25   29   30   31                                             
CONECT   29   28   32                                                       
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32   29   33                                                       
CONECT   33   32   34   35   36                                             
CONECT   34   33   37   38                                                  
CONECT   35   33                                                            
CONECT   36   33                                                            
CONECT   37   34   39   40                                                  
CONECT   38   34                                                            
CONECT   39   37   41                                                       
CONECT   40   37                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43   46                                                       
CONECT   45   43                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49   52   53                                                  
CONECT   51   49                                                            
CONECT   52   50   54   55                                                  
CONECT   53   50                                                            
CONECT   54   52                                                            
CONECT   55   52                                                            
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

COMPND    HMDB0001269
HETATM    1  C1  UNL     1      13.044  -1.248  -1.107  1.00  0.00           C  
HETATM    2  C2  UNL     1      13.243  -1.917   0.226  1.00  0.00           C  
HETATM    3  C3  UNL     1      13.753  -0.950   1.266  1.00  0.00           C  
HETATM    4  O1  UNL     1      13.970   0.254   1.035  1.00  0.00           O  
HETATM    5  O2  UNL     1      13.967  -1.516   2.529  1.00  0.00           O  
HETATM    6  C4  UNL     1      12.063  -2.664   0.673  1.00  0.00           C  
HETATM    7  O3  UNL     1      12.111  -3.905   0.393  1.00  0.00           O  
HETATM    8  S1  UNL     1      10.663  -2.031   1.514  1.00  0.00           S  
HETATM    9  C5  UNL     1      10.720  -0.314   1.900  1.00  0.00           C  
HETATM   10  C6  UNL     1      10.592   0.608   0.717  1.00  0.00           C  
HETATM   11  N1  UNL     1       9.336   0.376   0.007  1.00  0.00           N  
HETATM   12  C7  UNL     1       8.065   0.527   0.596  1.00  0.00           C  
HETATM   13  O4  UNL     1       7.969   0.878   1.787  1.00  0.00           O  
HETATM   14  C8  UNL     1       6.849   0.269  -0.200  1.00  0.00           C  
HETATM   15  C9  UNL     1       5.642   0.502   0.676  1.00  0.00           C  
HETATM   16  N2  UNL     1       4.397   0.265  -0.051  1.00  0.00           N  
HETATM   17  C10 UNL     1       3.174   0.439   0.626  1.00  0.00           C  
HETATM   18  O5  UNL     1       3.190   0.788   1.847  1.00  0.00           O  
HETATM   19  C11 UNL     1       1.837   0.242   0.021  1.00  0.00           C  
HETATM   20  O6  UNL     1       0.846   0.196   1.028  1.00  0.00           O  
HETATM   21  C12 UNL     1       1.454   1.421  -0.855  1.00  0.00           C  
HETATM   22  C13 UNL     1       2.456   1.563  -1.966  1.00  0.00           C  
HETATM   23  C14 UNL     1       1.382   2.674  -0.006  1.00  0.00           C  
HETATM   24  C15 UNL     1       0.066   1.095  -1.408  1.00  0.00           C  
HETATM   25  O7  UNL     1      -0.384   2.127  -2.235  1.00  0.00           O  
HETATM   26  P1  UNL     1      -1.906   1.805  -2.862  1.00  0.00           P  
HETATM   27  O8  UNL     1      -2.112   0.339  -3.127  1.00  0.00           O  
HETATM   28  O9  UNL     1      -2.070   2.677  -4.310  1.00  0.00           O  
HETATM   29  O10 UNL     1      -3.120   2.339  -1.819  1.00  0.00           O  
HETATM   30  P2  UNL     1      -4.384   1.206  -1.840  1.00  0.00           P  
HETATM   31  O11 UNL     1      -5.184   1.303  -3.123  1.00  0.00           O  
HETATM   32  O12 UNL     1      -3.701  -0.325  -1.708  1.00  0.00           O  
HETATM   33  O13 UNL     1      -5.432   1.447  -0.544  1.00  0.00           O  
HETATM   34  C16 UNL     1      -5.687   0.220   0.050  1.00  0.00           C  
HETATM   35  C17 UNL     1      -6.632   0.375   1.234  1.00  0.00           C  
HETATM   36  O14 UNL     1      -7.839   0.904   0.874  1.00  0.00           O  
HETATM   37  C18 UNL     1      -8.812  -0.056   0.910  1.00  0.00           C  
HETATM   38  N3  UNL     1      -9.709   0.016  -0.227  1.00  0.00           N  
HETATM   39  C19 UNL     1      -9.416   0.242  -1.517  1.00  0.00           C  
HETATM   40  N4  UNL     1     -10.542   0.227  -2.243  1.00  0.00           N  
HETATM   41  C20 UNL     1     -11.585  -0.010  -1.430  1.00  0.00           C  
HETATM   42  C21 UNL     1     -12.950  -0.128  -1.648  1.00  0.00           C  
HETATM   43  N5  UNL     1     -13.464   0.013  -2.963  1.00  0.00           N  
HETATM   44  N6  UNL     1     -13.720  -0.374  -0.575  1.00  0.00           N  
HETATM   45  C22 UNL     1     -13.184  -0.501   0.665  1.00  0.00           C  
HETATM   46  N7  UNL     1     -11.867  -0.390   0.896  1.00  0.00           N  
HETATM   47  C23 UNL     1     -11.045  -0.140  -0.167  1.00  0.00           C  
HETATM   48  C24 UNL     1      -8.128  -1.400   1.024  1.00  0.00           C  
HETATM   49  O15 UNL     1      -8.862  -2.315   1.772  1.00  0.00           O  
HETATM   50  C25 UNL     1      -6.885  -1.006   1.794  1.00  0.00           C  
HETATM   51  O16 UNL     1      -7.234  -0.914   3.138  1.00  0.00           O  
HETATM   52  P3  UNL     1      -6.252  -1.892   4.106  1.00  0.00           P  
HETATM   53  O17 UNL     1      -5.794  -1.067   5.294  1.00  0.00           O  
HETATM   54  O18 UNL     1      -7.099  -3.223   4.717  1.00  0.00           O  
HETATM   55  O19 UNL     1      -4.887  -2.405   3.225  1.00  0.00           O  
HETATM   56  H1  UNL     1      13.429  -0.206  -1.074  1.00  0.00           H  
HETATM   57  H2  UNL     1      13.595  -1.799  -1.880  1.00  0.00           H  
HETATM   58  H3  UNL     1      11.960  -1.202  -1.385  1.00  0.00           H  
HETATM   59  H4  UNL     1      14.103  -2.658   0.131  1.00  0.00           H  
HETATM   60  H5  UNL     1      14.337  -0.919   3.249  1.00  0.00           H  
HETATM   61  H6  UNL     1       9.895  -0.093   2.635  1.00  0.00           H  
HETATM   62  H7  UNL     1      11.663  -0.054   2.482  1.00  0.00           H  
HETATM   63  H8  UNL     1      11.447   0.649   0.051  1.00  0.00           H  
HETATM   64  H9  UNL     1      10.483   1.678   1.112  1.00  0.00           H  
HETATM   65  H10 UNL     1       9.402   0.079  -1.006  1.00  0.00           H  
HETATM   66  H11 UNL     1       6.881  -0.786  -0.557  1.00  0.00           H  
HETATM   67  H12 UNL     1       6.798   0.920  -1.111  1.00  0.00           H  
HETATM   68  H13 UNL     1       5.694   1.532   1.074  1.00  0.00           H  
HETATM   69  H14 UNL     1       5.728  -0.189   1.542  1.00  0.00           H  
HETATM   70  H15 UNL     1       4.424  -0.037  -1.035  1.00  0.00           H  
HETATM   71  H16 UNL     1       1.751  -0.669  -0.595  1.00  0.00           H  
HETATM   72  H17 UNL     1       0.647   1.121   1.268  1.00  0.00           H  
HETATM   73  H18 UNL     1       3.411   1.993  -1.609  1.00  0.00           H  
HETATM   74  H19 UNL     1       2.647   0.578  -2.422  1.00  0.00           H  
HETATM   75  H20 UNL     1       2.089   2.293  -2.743  1.00  0.00           H  
HETATM   76  H21 UNL     1       1.707   3.574  -0.581  1.00  0.00           H  
HETATM   77  H22 UNL     1       0.334   2.877   0.291  1.00  0.00           H  
HETATM   78  H23 UNL     1       1.985   2.611   0.919  1.00  0.00           H  
HETATM   79  H24 UNL     1      -0.675   1.010  -0.588  1.00  0.00           H  
HETATM   80  H25 UNL     1       0.113   0.120  -1.912  1.00  0.00           H  
HETATM   81  H26 UNL     1      -1.396   3.382  -4.383  1.00  0.00           H  
HETATM   82  H27 UNL     1      -2.989  -0.353  -1.030  1.00  0.00           H  
HETATM   83  H28 UNL     1      -6.133  -0.451  -0.713  1.00  0.00           H  
HETATM   84  H29 UNL     1      -4.763  -0.283   0.410  1.00  0.00           H  
HETATM   85  H30 UNL     1      -6.116   0.991   2.001  1.00  0.00           H  
HETATM   86  H31 UNL     1      -9.414   0.087   1.827  1.00  0.00           H  
HETATM   87  H32 UNL     1      -8.388   0.409  -1.875  1.00  0.00           H  
HETATM   88  H33 UNL     1     -13.034   0.577  -3.703  1.00  0.00           H  
HETATM   89  H34 UNL     1     -14.355  -0.500  -3.202  1.00  0.00           H  
HETATM   90  H35 UNL     1     -13.823  -0.701   1.530  1.00  0.00           H  
HETATM   91  H36 UNL     1      -7.893  -1.854   0.049  1.00  0.00           H  
HETATM   92  H37 UNL     1      -9.804  -2.258   1.484  1.00  0.00           H  
HETATM   93  H38 UNL     1      -6.041  -1.697   1.621  1.00  0.00           H  
HETATM   94  H39 UNL     1      -6.454  -3.965   4.789  1.00  0.00           H  
HETATM   95  H40 UNL     1      -4.144  -2.453   3.875  1.00  0.00           H  
CONECT    1    2   56   57   58
CONECT    2    3    6   59
CONECT    3    4    4    5
CONECT    5   60
CONECT    6    7    7    8
CONECT    8    9
CONECT    9   10   61   62
CONECT   10   11   63   64
CONECT   11   12   65
CONECT   12   13   13   14
CONECT   14   15   66   67
CONECT   15   16   68   69
CONECT   16   17   70
CONECT   17   18   18   19
CONECT   19   20   21   71
CONECT   20   72
CONECT   21   22   23   24
CONECT   22   73   74   75
CONECT   23   76   77   78
CONECT   24   25   79   80
CONECT   25   26
CONECT   26   27   27   28   29
CONECT   28   81
CONECT   29   30
CONECT   30   31   31   32   33
CONECT   32   82
CONECT   33   34
CONECT   34   35   83   84
CONECT   35   36   50   85
CONECT   36   37
CONECT   37   38   48   86
CONECT   38   39   47
CONECT   39   40   40   87
CONECT   40   41
CONECT   41   42   42   47
CONECT   42   43   44
CONECT   43   88   89
CONECT   44   45   45
CONECT   45   46   90
CONECT   46   47   47
CONECT   48   49   50   91
CONECT   49   92
CONECT   50   51   93
CONECT   51   52
CONECT   52   53   53   54   55
CONECT   54   94
CONECT   55   95
END

HMDB0001269
     RDKit          3D
Methylmalonyl-CoA
 95 97  0  0  0  0  0  0  0  0999 V2000
   13.0444   -1.2484   -1.1068 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2427   -1.9168    0.2262 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.7527   -0.9503    1.2663 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9701    0.2537    1.0352 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.9674   -1.5160    2.5292 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.0630   -2.6641    0.6727 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1105   -3.9048    0.3935 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.6633   -2.0313    1.5136 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.7200   -0.3143    1.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5917    0.6078    0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3359    0.3759    0.0066 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0645    0.5269    0.5957 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9686    0.8779    1.7873 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8489    0.2691   -0.1998 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6416    0.5024    0.6759 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3974    0.2650   -0.0511 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.1738    0.4390    0.6263 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1902    0.7877    1.8471 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8373    0.2416    0.0210 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8461    0.1964    1.0284 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4535    1.4208   -0.8554 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4560    1.5631   -1.9664 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3821    2.6744   -0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0663    1.0952   -1.4076 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3837    2.1271   -2.2350 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9059    1.8051   -2.8619 P   0  0  0  0  0  5  0  0  0  0  0  0
   -2.1118    0.3390   -3.1267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0704    2.6769   -4.3097 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1200    2.3388   -1.8194 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3840    1.2059   -1.8404 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.1841    1.3029   -3.1226 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7014   -0.3255   -1.7079 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4324    1.4472   -0.5440 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6874    0.2205    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6321    0.3753    1.2342 C   0  0  1  0  0  0  0  0  0  0  0  0
   -7.8386    0.9036    0.8740 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8121   -0.0564    0.9099 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.7088    0.0165   -0.2269 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4158    0.2424   -1.5169 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5419    0.2270   -2.2431 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5850   -0.0102   -1.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.9501   -0.1281   -1.6482 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4640    0.0130   -2.9632 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.7198   -0.3740   -0.5753 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.1844   -0.5010    0.6653 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8666   -0.3902    0.8962 N   0  0  0  0  0  0  0  0  0  0  0  0
  -11.0454   -0.1400   -0.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1284   -1.3999    1.0241 C   0  0  2  0  0  0  0  0  0  0  0  0
   -8.8617   -2.3147    1.7717 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8852   -1.0060    1.7939 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.2336   -0.9135    3.1379 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2522   -1.8921    4.1056 P   0  0  0  0  0  5  0  0  0  0  0  0
   -5.7942   -1.0666    5.2940 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0988   -3.2228    4.7169 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8873   -2.4047    3.2254 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4291   -0.2058   -1.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
   13.5954   -1.7992   -1.8799 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.9596   -1.2017   -1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.1027   -2.6577    0.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   14.3370   -0.9194    3.2494 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8948   -0.0925    2.6351 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.6633   -0.0543    2.4825 H   0  0  0  0  0  0  0  0  0  0  0  0
   11.4468    0.6486    0.0513 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4833    1.6784    1.1119 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4021    0.0785   -1.0060 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8808   -0.7865   -0.5571 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7977    0.9204   -1.1112 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6944    1.5318    1.0742 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7275   -0.1892    1.5416 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4241   -0.0370   -1.0347 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7509   -0.6694   -0.5951 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6470    1.1205    1.2677 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4108    1.9932   -1.6093 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6468    0.5783   -2.4220 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0888    2.2926   -2.7432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7075    3.5736   -0.5808 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3338    2.8767    0.2906 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9845    2.6107    0.9186 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6751    1.0105   -0.5884 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1126    0.1202   -1.9116 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3956    3.3824   -4.3833 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9895   -0.3530   -1.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1333   -0.4511   -0.7129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7632   -0.2833    0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1159    0.9912    2.0008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.4139    0.0875    1.8269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3878    0.4093   -1.8751 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.0345    0.5774   -3.7029 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.3552   -0.4996   -3.2016 H   0  0  0  0  0  0  0  0  0  0  0  0
  -13.8226   -0.7007    1.5300 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8934   -1.8544    0.0485 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8039   -2.2580    1.4843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0406   -1.6972    1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4543   -3.9650    4.7894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1443   -2.4532    3.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  0
  3  5  1  0
  2  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  2  0
 17 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
 21 23  1  0
 21 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  2  0
 26 28  1  0
 26 29  1  0
 29 30  1  0
 30 31  2  0
 30 32  1  0
 30 33  1  0
 33 34  1  0
 34 35  1  0
 35 36  1  0
 36 37  1  0
 37 38  1  0
 38 39  1  0
 39 40  2  0
 40 41  1  0
 41 42  2  0
 42 43  1  0
 42 44  1  0
 44 45  2  0
 45 46  1  0
 46 47  2  0
 37 48  1  0
 48 49  1  0
 48 50  1  0
 50 51  1  0
 51 52  1  0
 52 53  2  0
 52 54  1  0
 52 55  1  0
 50 35  1  0
 47 38  1  0
 47 41  1  0
  1 56  1  0
  1 57  1  0
  1 58  1  0
  2 59  1  6
  5 60  1  0
  9 61  1  0
  9 62  1  0
 10 63  1  0
 10 64  1  0
 11 65  1  0
 14 66  1  0
 14 67  1  0
 15 68  1  0
 15 69  1  0
 16 70  1  0
 19 71  1  0
 20 72  1  0
 22 73  1  0
 22 74  1  0
 22 75  1  0
 23 76  1  0
 23 77  1  0
 23 78  1  0
 24 79  1  0
 24 80  1  0
 28 81  1  0
 32 82  1  0
 34 83  1  0
 34 84  1  0
 35 85  1  1
 37 86  1  1
 39 87  1  0
 43 88  1  0
 43 89  1  0
 45 90  1  0
 48 91  1  6
 49 92  1  0
 50 93  1  1
 54 94  1  0
 55 95  1  0
M  END

Synonyms

Value	Source
(R)-Methylmalonyl-CoA	HMDB
(R)-Methylmalonyl-coenzyme A	HMDB
(S)-2-Methyl-3-oxopropanoyl-CoA	HMDB
(S)-Methyl-malonyl-CoA	HMDB
(S)-Methyl-malonyl-coenzyme A	HMDB
CH3-Malonyl-CoA	HMDB
CH3-Malonyl-coenzyme A	HMDB
D-Methylmalonyl-CoA	HMDB
D-Methylmalonyl-coenzyme A	HMDB
L-Methylmalonyl-CoA	HMDB
L-Methylmalonyl-coenzyme A	HMDB
Methyl-malonyl-coenzyme A	HMDB

Molecular Formula

C₂₅H₄₀N₇O₁₉P₃S

Average Mass

867.607

Monoisotopic Mass

867.131252359

IUPAC Name

(2S)-3-{[2-(3-{3-[({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)methyl]-2-hydroxy-3-methylbutanamido}propanamido)ethyl]sulfanyl}-2-methyl-3-oxopropanoic acid

Traditional Name

(2S)-3-({2-[3-(3-{[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]methyl}-2-hydroxy-3-methylbutanamido)propanamido]ethyl}sulfanyl)-2-methyl-3-oxopropanoic acid

CAS Registry Number

Not Available

SMILES

C[C@@H](C(O)=O)C(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@H]1O[C@H]([C@H](O)[C@@H]1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C25H40N7O19P3S/c1-12(23(37)38)24(39)55-7-6-27-14(33)4-5-28-21(36)18(35)25(2,3)9-48-54(45,46)51-53(43,44)47-8-13-17(50-52(40,41)42)16(34)22(49-13)32-11-31-15-19(26)29-10-30-20(15)32/h10-13,16-18,22,34-35H,4-9H2,1-3H3,(H,27,33)(H,28,36)(H,37,38)(H,43,44)(H,45,46)(H2,26,29,30)(H2,40,41,42)/t12-,13+,16+,17+,18?,22+/m0/s1

InChI Key

MZFOKIKEPGUZEN-PNEPRAIJSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyl coas. These are organic compounds containing a coenzyme A substructure linked to an acyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Acyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Alkyl phosphate
1,3-dicarbonyl compound
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Heteroaromatic compound
Azole
Thiocarboxylic acid ester
Carbothioic s-ester
Secondary alcohol
Amino acid
Carboxamide group
Amino acid or derivatives
Secondary carboxylic acid amide
Organoheterocyclic compound
Sulfenyl compound
Thiocarboxylic acid or derivatives
Azacycle
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Monocarboxylic acid or derivatives
Organic oxygen compound
Primary amine
Hydrocarbon derivative
Carbonyl group
Organosulfur compound
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Organic nitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.57 g/L	ALOGPS
logP	-0.6	ALOGPS
logP	-6.5	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.97	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	400.93 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	183.13 m³·mol⁻¹	ChemAxon
Polarizability	75.35 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-4911000020-3f5d871d28d1f2657e02	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1913000000-eb05e99fd73a630e7c4a	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-3911000000-ec1f0018f511db865738	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-017j-9811140550-4b48b6e3d5690659e256	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-4911110010-d9e5414e595f184f73ca	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-464114c146993e32adb3	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-014i-0000000490-c603c70c007f70ef33b6	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-9100001110-674e7f26ced429f76abf	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0fia-6002504900-00628ec73e3d0c21b3b1	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-014i-0000000190-d1ac902744892ad8fd49	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0900002540-5a0ea7d9050df0a16eac	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-03di-1159000000-73eadba5e764ea21f78b	2021-09-25	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)		2021-09-29	View Spectrum

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (retained)	2025-10-23	681.3
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-23	549.7
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-23	247.6
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-23	421.8
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-23	355.5
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-23	173.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	1027.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	876.9
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-23	389.7
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	143.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-23	352.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-23	163.6
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	81.5
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	600.0
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-23	498.4
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	77.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-23	261.1
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-23	718.2
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-23	639.6

Retention Indices

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane
Mitochondria

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0191725	Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial	Unknown	Q02252	Homo sapiens
MMDBp0191926	Methylmalonyl-CoA epimerase, mitochondrial	Enzyme	Q96PE7	Homo sapiens
MMDBp0191927	Methylmalonyl-CoA mutase, mitochondrial	Enzyme	P22033	Homo sapiens
MMDBp0191928	Propionyl-CoA carboxylase beta chain, mitochondrial	Enzyme	P05166	Homo sapiens
MMDBp0191929	Propionyl-CoA carboxylase alpha chain, mitochondrial	Enzyme	P05165	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Name	SMPDB/PathBank	Species
3-Hydroxypropionate bi-cycle
Erythromycin biosynthesis		Escherichia coli Pseudomonas aeruginosa Escherichia coli UTI89 Mycobacterium marinum M Pseudomonas aeruginosa PA7 Acinetobacter sp. ADP1 Escherichia coli CFT073 Myxococcus xanthus DK 1622 Ochrobactrum anthropi Bacillus subtilis Mycobacterium tuberculosis Bacillus cereus Pseudomonas fluorescens Pf-5 Streptomyces griseus subsp. griseus NBRC 13350 Mycobacterium tuberculosis CDC1551 Bacillus amyloliquefaciens Clostridium saccharoperbutylacetonicum N1-4(HMT) Clostridium acetobutylicum ATCC 824 Clostridium sporogenes Aromatoleum aromaticum EbN1 Saccharopolyspora erythraea NRRL 2338 Streptomyces avermitilis MA-4680 Bacillus cereus AH187 (F4810/72) Bacillus halodurans C-125 Alkalihalobacillus pseudofirmus OF4 Brevibacillus brevis NBRC 100599 Clostridium beijerinckii NCIMB 8052 Methylobacterium nodulans Ochrobactrum anthropi ATCC 49188 Ochrobactrum intermedium LMG 3301 Parabacteroides distasonis Parabacteroides distasonis ATCC 8503 Parabacteroides goldsteinii dnLKV18 Thermus thermophilus Comamonas testosteroni Burkholderia cepacia Pseudomonas fluorescens Pseudomonas mendocina Bradyrhizobium japonicum Mesorhizobium loti Sinorhizobium meliloti Methylococcus capsulatus Shigella dysenteriae Aeromonas hydrophila Deinococcus radiodurans Streptococcus mutans Bacillus licheniformis Priestia megaterium Bacillus mycoides Bacillus pumilus Bacillus thuringiensis Cellulomonas flavigena Mycobacterium avium Roseobacter denitrificans Acidothermus cellulolyticus Campylobacter upsaliensis Enterococcus avium Stenotrophomonas maltophilia Actinosynnema mirum Bacillus clausii Bacillus pseudofirmus Bacillus selenitireducens Achromobacter xylosoxidans Burkholderia multivorans Burkholderia cenocepacia Syntrophobacter fumaroxidans Burkholderia ambifaria Alicycliphilus denitrificans Bacteroides faecis Agrobacterium tumefaciens Campylobacter coli Campylobacter jejuni Clostridium beijerinckii Parabacteroides goldsteinii Rothia dentocariosa Rothia mucilaginosa Achromobacter xylosoxidans A8 Aeromonas hydrophila subsp. hydrophila ATCC 7966 Agrobacterium tumefaciens str. C58 Bacillus cereus ATCC 10987 Bacillus megaterium QM B1551 Bacillus thuringiensis serovar konkukian str. 97-27 Bacillus licheniformis ATCC 14580 Bacillus clausii KSM-K16 Bacillus amyloliquefaciens FZB42 Bacillus pumilus SAFR-032 Bacillus cereus B4264 Bacillus cereus AH820 Bacillus cereus G9842 Bacillus cereus Q1 Priestia megaterium DSM 319 Bacillus subtilis subsp. spizizenii str. W23 Bacillus amyloliquefaciens DSM 7 Bradyrhizobium japonicum USDA 110 Campylobacter jejuni subsp. jejuni 81-176 Campylobacter jejuni subsp. doylei 269.97 Clostridium botulinum A str. Hall Clostridium botulinum A2 str. Kyoto Cryptobacterium curtum DSM 15641 Delftia acidovorans SPH-1 Escherichia coli APEC O1 Lysinibacillus sphaericus C3-41 Mesorhizobium loti MAFF303099 Methylobacterium radiotolerans JCM 2831 Methylobacterium populi BJ001 Mycobacterium avium subsp. paratuberculosis K-10 Mycobacterium avium 104 Escherichia coli 042 Pseudomonas putida KT2440 Pseudomonas fluorescens Pf0-1 Pseudomonas fluorescens SBW25 Rhizobium leguminosarum bv. viciae 3841 Rhizobium leguminosarum bv. trifolii WSM2304 Rhodococcus erythropolis PR4 Rothia mucilaginosa DY-18 Rothia dentocariosa ATCC 17931 Salmonella enterica subsp. enterica serovar Typhimurium str. LT2 Salmonella enterica subsp. enterica serovar Newport str. SL254 Salmonella enterica subsp. enterica serovar Heidelberg str. SL476 Salmonella enterica subsp. enterica serovar Agona str. SL483 Salmonella enterica subsp. enterica serovar Dublin str. CT02021853 Shigella dysenteriae Sd197 Spirosoma linguale DSM 74 Staphylococcus haemolyticus JCSC1435 Stenotrophomonas maltophilia K279a Streptococcus mutans UA159 Bacteroides sp. D2 Parabacteroides sp. D13 Spirosoma linguale Beijerinckia indica Bradyrhizobium elkanii Methylobacterium mesophilicum Methylobacterium mesophilicum SR1.6/6 Rhizobium etli Azorhizobium caulinodans Xanthobacter autotrophicus Alcaligenes faecalis Burkholderia cepacia GG4 Methyloversatilis universalis Methyloversatilis universalis FAM5 Cedecea davisae Cedecea davisae DSM 4568 Enterobacter hormaechei Klebsiella aerogenes Salmonella enterica subsp. enterica serovar Typhimurium Trabulsiella guamensis Trabulsiella guamensis ATCC 49490 Serratia marcescens subsp. marcescens Db11 Yersinia pseudotuberculosis Actinomyces viscosus C505 Bifidobacterium boum Gordonia terrae C-6 Rhodococcus erythropolis Brevibacterium casei Brevibacterium casei S18 Brevibacterium linens Rothia aeria F0474 Cellulosimicrobium cellulans Streptomyces avermitilis Thermomonospora curvata Cryptobacterium curtum Bacillus altitudinis Lysinibacillus sphaericus Aneurinibacillus aneurinilyticus Aneurinibacillus aneurinilyticus ATCC 12856 Paenibacillus lactis 154 Clostridium celatum DSM 1785 [Eubacterium] cellulosolvens 6 Halococcus morrhuae DSM 1307 Halococcus morrhuae Streptomyces coelicolor A3(2) Ralstonia eutropha H16 Clostridioides difficile 630 Clostridioides difficile NAP08 Bacillus cytotoxicus NVH 391-98 Acidothermus cellulolyticus 11B Alicyclobacillus acidocaldarius subsp. acidocaldarius DSM 446 Amycolatopsis mediterranei U32 Arthrobacter sp. FB24 Arthrobacter aurescens TC1 Arthrobacter chlorophenolicus A6 Bacillus selenitireducens MLS10 Beutenbergia cavernae DSM 12333 Catenulispora acidiphila DSM 44928 Cellulomonas flavigena DSM 20109 Clavibacter michiganensis subsp. michiganensis NCPPB 382 Clostridium kluyveri DSM 555 Clostridium kluyveri NBRC 12016 Conexibacter woesei DSM 14684 Deinococcus radiodurans R1 Deinococcus geothermalis DSM 11300 Deinococcus proteolyticus MRP Frankia alni ACN14a Frankia sp. EuI1c Gordonia bronchialis DSM 43247 Intrasporangium calvum DSM 43043 Kineococcus radiotolerans SRS30216 Kribbella flavida DSM 17836 Mycobacterium leprae TN Mycobacterium bovis AF2122/97 Mycobacterium ulcerans Agy99 Mycobacterium vanbaalenii PYR-1 Mycobacterium bovis BCG str. Pasteur 1173P2 Mycobacterium tuberculosis H37Ra Mycobacterium abscessus ATCC 19977 Mycobacterium leprae Br4923 Mycobacterium sp. Spyr1 Mycobacterium sp. JDM601 Mycobacterium canettii CIPT 140010059 Nakamurella multipartita DSM 44233 Nocardia farcinica IFM 10152 Nocardioides sp. JS614 Thermobaculum terrenum ATCC BAA-798 Pseudonocardia dioxanivorans CB1190 Renibacterium salmoninarum ATCC 33209 Rhodococcus opacus B4 Rhodococcus jostii RHA1 Rhodococcus equi 103S Rubrobacter xylanophilus DSM 9941 Saccharomonospora viridis DSM 43017 Salinispora tropica CNB-440 Slackia heliotrinireducens DSM 20476 Sphaerobacter thermophilus DSM 20745 Stackebrandtia nassauensis DSM 44728 Streptomyces scabiei 87.22 Streptomyces violaceusniger Tu 4113 Streptosporangium roseum DSM 43021 Symbiobacterium thermophilum IAM 14863 Thermobispora bispora DSM 43833 Thermomonospora curvata DSM 43183 Tsukamurella paurometabola DSM 20162 Aspergillus nomiae NRRL 13137 Aspergillus novofumigatus Aspergillus novofumigatus IBT 16806 Aspergillus parasiticus SU-1 Aspergillus phoenicis Aspergillus ruber Aspergillus sclerotioniger Aspergillus glaucus Aspergillus aculeatus ATCC 16872 Aspergillus leporis Aspergillus niger ATCC 1015 Aspergillus oryzae RIB40 Aspergillus terreus NIH2624 Aspergillus wentii Aspergillus clavatus NRRL 1 Aspergillus fischeri NRRL 181 Aspergillus fumigatus A1163 Aspergillus fumigatus Af293 Aspergillus calidoustus Aspergillus nidulans FGSC A4 Aspergillus taichungensis Aspergillus tamarii Aspergillus thermomutatus Aspergillus tubingensis Aspergillus ustus Aspergillus violaceofuscus Aspergillus viridinutans Penicillium brasilianum Penicillium brevicompactum Penicillium canescens Penicillium chermesinum Penicillium citrinum Penicillium concentricum Penicillium daleae Penicillium decumbens Penicillium griseofulvum Penicillium hordei Penicillium italicum Penicillium nalgiovense Penicillium oxalicum Penicillium polonicum Penicillium roqueforti FM164 Penicillium solitum Penicillium steckii Penicillium thymicola Penicillium vulpinum Verticillium alfalfae VaMs.102 Trichoderma arundinaceum Trichoderma asperellum Trichoderma atroviride IMI 206040 Trichoderma citrinoviride Trichoderma harzianum Trichoderma longibrachiatum Trichoderma parareesei Trichoderma reesei QM6a Trichoderma virens Trichoderma virens Gv29-8 Fusarium acutatum Fusarium fujikuroi IMI 58289 Fusarium mangiferae Fusarium nygamai Fusarium proliferatum ET1 Fusarium subglutinans Fusarium verticillioides 7600 Fusarium heterosporum Fusarium equiseti Fusarium oxysporum Fo5176 Fusarium oxysporum f. sp. lycopersici 4287 Fusarium austroamericanum Fusarium graminearum PH-1 Fusarium poae Fusarium pseudograminearum CS3096 Fusarium sporotrichioides Fusarium vanettenii Fusarium vanettenii 77-13-4 Fusarium tricinctum Paraburkholderia graminis C4D1M Mycolicibacterium fortuitum subsp. fortuitum DSM 46621 = ATCC 6841 Rhodococcus hoagii ATCC 33707 Acidipropionibacterium acidipropionici ATCC 4875 Klebsiella aerogenes KCTC 2190 Acaryochloris marina MBIC11017 Acidobacterium capsulatum ATCC 51196 Acidovorax citrulli AAC00-1 Acidovorax sp. JS42 Aeromonas salmonicida subsp. salmonicida A449 Agrobacterium vitis S4 Agrobacterium radiobacter K84 Rhodoferax ferrireducens T118 Alcanivorax borkumensis SK2 Alicycliphilus denitrificans K601 Anabaena variabilis ATCC 29413 Anaeromyxobacter sp. Fw109-5 Aquifex aeolicus VF5 Azorhizobium caulinodans ORS 571 Beijerinckia indica subsp. indica ATCC 9039 Bradyrhizobium sp. ORS278 Bradyrhizobium sp. BTAi1 Brucella melitensis bv. 1 str. 16M Brucella abortus bv. 1 str. 9-941 Brucella canis ATCC 23365 Brucella suis ATCC 23445 Brucella abortus S19 Brucella melitensis ATCC 23457 Brucella microti CCM 4915 Burkholderia mallei ATCC 23344 Burkholderia pseudomallei 1710b Burkholderia sp. 383 Burkholderia xenovorans LB400 Burkholderia ambifaria AMMD Burkholderia mallei NCTC 10229 Burkholderia pseudomallei 1106a Burkholderia cenocepacia MC0-3 Burkholderia ambifaria MC40-6 Burkholderia phymatum STM815 Burkholderia phytofirmans PsJN Burkholderia cenocepacia J2315 Burkholderia rhizoxinica HKI 454 Candidatus Koribacter versatilis Ellin345 Caulobacter crescentus CB15 Caulobacter crescentus NA1000 Caulobacter segnis ATCC 21756 Cellulophaga algicola DSM 14237 Cellvibrio gilvus ATCC 13127 Chitinophaga pinensis DSM 2588 Chloroflexus aurantiacus J-10-fl Chloroflexus aggregans DSM 9485 Cupriavidus metallidurans CH34 Cupriavidus taiwanensis LMG 19424 Cupriavidus necator N-1 Cyanothece sp. ATCC 51142 Cyanothece sp. PCC 8801 Cyanothece sp. PCC 7424 Deinococcus deserti VCD115 Dickeya dadantii Ech703 Dickeya zeae Ech1591 Dickeya dadantii Ech586 Dickeya dadantii 3937 Dinoroseobacter shibae DFL 12 Erythrobacter litoralis HTCC2594 Gloeobacter violaceus PCC 7421 Gluconacetobacter diazotrophicus PAl 5 Gramella forsetii KT0803 Hahella chejuensis KCTC 2396 Haliangium ochraceum DSM 14365 Haloterrigena turkmenica DSM 5511 Halothiobacillus neapolitanus c2 Herpetosiphon aurantiacus DSM 785 Hyphomonas neptunium ATCC 15444 Jannaschia sp. CCS1 Maricaulis maris MCS10 Marinobacter aquaeolei VT8 Marinomonas mediterranea MMB-1 Methylobacterium chloromethanicum CM4 Methylobacterium nodulans ORS 2060 Methylobacterium extorquens AM1 Methylobacterium extorquens DM4 Methylocella silvestris BL2 Microcystis aeruginosa NIES-843 Nitrobacter winogradskyi Nb-255 Nitrobacter hamburgensis X14 Nitrosococcus halophilus Nc4 Nitrosomonas eutropha C91 Nitrosospira multiformis ATCC 25196 Nostoc sp. PCC 7120 Nostoc punctiforme PCC 73102 Novosphingobium aromaticivorans DSM 12444 Bordetella bronchiseptica RB50 Xanthomonas axonopodis pv. citri str. 306 Thermus thermophilus HB27 Sorangium cellulosum 'So ce 56' Opitutus terrae PB90-1 Rhodobacter capsulatus SB1003 Paracoccus denitrificans PD1222 Parvibaculum lavamentivorans DS-1 Pectobacterium atrosepticum SCRI1043 Pectobacterium carotovorum subsp. carotovorum PC1 Pedobacter heparinus DSM 2366 Phenylobacterium zucineum HLK1 Photobacterium profundum SS9 Photorhabdus luminescens subsp. laumondii TTO1 Pirellula staleyi DSM 6068 Planctomyces limnophilus DSM 3776 Polaromonas sp. JS666 Prochlorococcus marinus str. MIT 9313 Prochlorococcus marinus str. MIT 9303 Pseudomonas entomophila L48 Ralstonia solanacearum GMI1000 Rhizobium etli CFN 42 Rhizobium etli CIAT 652 Rhizobium leguminosarum bv. trifolii WSM1325 Rhodopseudomonas palustris CGA009 Rhodopseudomonas palustris HaA2 Rhodopseudomonas palustris BisB5 Roseiflexus sp. RS-1 Roseiflexus castenholzii DSM 13941 Roseobacter denitrificans OCh 114 Roseobacter litoralis Och 149 Ruegeria pomeroyi DSS-3 Ruegeria sp. TM1040 Salmonella enterica subsp. enterica serovar Paratyphi A str. Segniliparus rotundus DSM 44985 Sinorhizobium meliloti 1021 Sinorhizobium medicae WSM419 Sphingobium japonicum UT26S Sphingomonas wittichii RW1 Sphingopyxis alaskensis RB2256 Synechococcus sp. WH 8102 Synechococcus sp. CC9902 Synechococcus sp. CC9311 Synechococcus sp. WH 7803 Synechococcus sp. RCC307 Synechococcus sp. PCC 7002 Syntrophobacter fumaroxidans MPOB Variovorax paradoxus EPS Vibrio splendidus LGP32 Xanthobacter autotrophicus Py2 Xanthomonas campestris pv. vesicatoria str. 85-10 Xenorhabdus bovienii SS-2004 Xenorhabdus nematophila ATCC 19061 Zunongwangia profunda SM-A87
Threonine Biosynthesis		Escherichia coli Pseudomonas aeruginosa Escherichia coli SMS-3-5 Escherichia coli UTI89 Escherichia coli 55989 Escherichia coli SE11 Mycobacterium marinum M Pseudomonas aeruginosa PA7 Actinobacillus succinogenes 130Z Escherichia coli CFT073 Ochrobactrum anthropi Bacillus subtilis Pseudomonas stutzeri Klebsiella pneumoniae Bacillus cereus Pseudomonas fluorescens Pf-5 Mycobacterium tuberculosis CDC1551 Bacillus amyloliquefaciens Streptococcus pneumoniae Clostridium saccharoperbutylacetonicum N1-4(HMT) Salmonella enterica Helicobacter pylori Staphylococcus aureus Haemophilus influenzae Haemophilus influenzae Rd KW20 Clostridium sporogenes Rhodospirillum rubrum ATCC 11170 Lactobacillus fermentum IFO 3956 Streptococcus pneumoniae TIGR4 Aromatoleum aromaticum EbN1 Shewanella denitrificans OS217 Acidaminococcus fermentans DSM 20731 Acidaminococcus intestini RyC-MR95 Arcobacter butzleri RM4018 Bacillus cereus AH187 (F4810/72) Bacteroides caccae Bacteroides cellulosilyticus Bacteroides eggerthii Bacteroides fragilis Bacteroides fragilis 638R Bacteroides fragilis YCH46 Bacteroides ovatus Bacteroides stercoris Bacteroides stercoris ATCC 43183 Bacteroides thetaiotaomicron Bacteroides thetaiotaomicron VPI-5482 Bacteroides vulgatus Bacteroides xylanisolvens XB1A Bifidobacterium mongoliense DSM 21395 Brevibacillus brevis NBRC 100599 Clostridium beijerinckii NCIMB 8052 Clostridium botulinum Dysgonomonas gadei ATCC BAA-286 Geobacter metallireducens Limosilactobacillus fermentum Lactobacillus paracasei Lactobacillus reuteri Methylobacterium nodulans Ochrobactrum anthropi ATCC 49188 Ochrobactrum intermedium LMG 3301 Parabacteroides distasonis Parabacteroides distasonis ATCC 8503 Parabacteroides goldsteinii dnLKV18 Prevotella ruminicola 23 Streptococcus salivarius Pelobacter carbinolicus Spirochaeta thermophila Campylobacter lari Comamonas testosteroni Burkholderia cepacia Pseudomonas fluorescens Pseudomonas mendocina Pseudomonas putida Pseudomonas syringae Xanthomonas campestris Bradyrhizobium japonicum Mesorhizobium loti Sinorhizobium meliloti Moraxella catarrhalis Neisseria flavescens Neisseria gonorrhoeae Neisseria mucosa Acidiphilium cryptum Chromobacterium violaceum Citrobacter koseri Proteus mirabilis Shigella boydii Shigella dysenteriae Shigella flexneri Shigella sonnei Aeromonas hydrophila Vibrio cholerae Vibrio vulnificus Bacteroides uniformis Campylobacter gracilis Fusobacterium ulcerans Syntrophomonas wolfei Desulfovibrio salexigens Desulfovibrio piger Cytophaga hutchinsonii Rhodopseudomonas palustris Chlorobium phaeobacteroides Leuconostoc mesenteroides Staphylococcus epidermidis Deinococcus radiodurans Streptococcus gordonii Streptococcus sanguinis Streptococcus mutans Streptococcus agalactiae Streptococcus dysgalactiae Streptococcus equinus Streptococcus equi Streptococcus uberis Bacillus licheniformis Priestia megaterium Bacillus mycoides Bacillus pumilus Clostridium kluyveri Lactobacillus delbrueckii Lactobacillus helveticus Lactobacillus plantarum Lactobacillus amylovorus Actinomyces viscosus Corynebacterium diphtheriae Corynebacterium glutamicum Desulfobacterium autotrophicum Thermotoga neapolitana Xylella fastidiosa Roseobacter denitrificans Staphylococcus lugdunensis Acidothermus cellulolyticus Campylobacter upsaliensis Neisseria subflava Staphylococcus saprophyticus Pelobacter propionicus Caldicellulosiruptor bescii Helicobacter pullorum Thiobacillus denitrificans Helicobacter bilis Stenotrophomonas maltophilia Leptotrichia buccalis Caldicellulosiruptor saccharolyticus Streptococcus cristatus Desulfotomaculum reducens Burkholderia vietnamiensis Holdemania filiformis Sodalis glossinidius Streptococcus peroris Enterobacter cancerogenus Streptococcus constellatus Bifidobacterium gallicum Bacillus selenitireducens Achromobacter xylosoxidans Burkholderia multivorans Burkholderia cenocepacia Actinomyces urogenitalis Methylibium petroleiphilum Pelotomaculum thermopropionicum Syntrophobacter fumaroxidans Citrobacter youngae Leuconostoc kimchii Burkholderia ambifaria Prevotella copri Ilyobacter polytropus Alicycliphilus denitrificans Desulfovibrio magneticus Shewanella denitrificans Methylocella silvestris Bacteroides massiliensis Escherichia albertii Dialister invisus Geobacter bemidjiensis Lactobacillus ultunensis Streptococcus pseudopneumoniae Bacteroides nordii Bacteroides plebeius Phocaeicola coprocola Geobacter lovleyi Streptococcus gallolyticus Syntrophus aciditrophicus Bacteroides intestinalis Bacteroides salanitronis Actinomyces oris Bacteroides fluxus Bacteroides oleiciplenus Bacteroides faecis Agrobacterium tumefaciens Bacteroides helcogenes Bacteroides xylanisolvens Bifidobacterium animalis Campylobacter coli Campylobacter jejuni Clostridium beijerinckii Dysgonomonas gadei Klebsiella variicola Lactobacillus rhamnosus Lactococcus lactis Leuconostoc citreum Parabacteroides goldsteinii Prevotella ruminicola Streptococcus parasanguinis Streptococcus suis Streptococcus thermophiles Rothia dentocariosa Rothia mucilaginosa Barnesiella intestinihominis Achromobacter xylosoxidans A8 Actinobacillus pleuropneumoniae serovar 5b str. L20 Actinobacillus pleuropneumoniae serovar 7 str. AP76 Aeromonas hydrophila subsp. hydrophila ATCC 7966 Agrobacterium tumefaciens str. C58 Atopobium parvulum DSM 20469 Bacillus cereus ATCC 10987 Bacillus megaterium QM B1551 Bacillus licheniformis ATCC 14580 Bacillus amyloliquefaciens FZB42 Bacillus pumilus SAFR-032 Bacillus cereus AH820 Bacillus cereus Q1 Priestia megaterium DSM 319 Bacillus subtilis subsp. spizizenii str. W23 Bacillus amyloliquefaciens DSM 7 Bifidobacterium animalis subsp. lactis AD011 Bradyrhizobium japonicum USDA 110 Campylobacter jejuni subsp. jejuni 81-176 Campylobacter jejuni subsp. doylei 269.97 Campylobacter lari RM2100 Citrobacter koseri ATCC BAA-895 Clostridium botulinum A str. Hall Clostridium botulinum B1 str. Okra Clostridium botulinum A2 str. Kyoto Clostridium botulinum Ba4 str. 657 Corynebacterium aurimucosum ATCC 700975 Corynebacterium kroppenstedtii DSM 44385 Cronobacter sakazakii ATCC BAA-894 Delftia acidovorans SPH-1 Dyadobacter fermentans DSM 18053 Enterobacter cloacae subsp. cloacae ATCC 13047 Escherichia coli APEC O1 Escherichia coli E24377A Escherichia coli O127:H6 str. E2348/69 Escherichia coli UMN026 Escherichia fergusonii ATCC 35469 Escherichia coli ED1a Escherichia coli IAI39 Haemophilus influenzae 86-028NP Haemophilus influenzae PittGG Helicobacter pylori J99 Helicobacter pylori G27 Helicobacter pylori P12 Klebsiella pneumoniae subsp. pneumoniae MGH 78578 Kytococcus sedentarius DSM 20547 Lactobacillus plantarum WCFS1 Lactobacillus acidophilus NCFM Lactobacillus casei ATCC 334 Lactobacillus amylovorus GRL 1112 Lactobacillus reuteri SD2112 Lactococcus lactis subsp. lactis Il1403 Lactococcus lactis subsp. cremoris SK11 Lactococcus lactis subsp. cremoris MG1363 Laribacter hongkongensis HLHK9 Leptotrichia buccalis C-1013-b Leuconostoc mesenteroides subsp. mesenteroides ATCC 8293 Mesorhizobium loti MAFF303099 Methylobacterium radiotolerans JCM 2831 Methylobacterium populi BJ001 Neisseria gonorrhoeae FA 1090 Neisseria meningitidis MC58 Neisseria meningitidis Z2491 Neisseria meningitidis FAM18 Neisseria gonorrhoeae NCCP11945 Escherichia coli 042 Edwardsiella tarda FL6-60 Bifidobacterium animalis subsp. lactis CNCM I-2494 Propionibacterium freudenreichii subsp. shermanii CIRM-BIA1 Proteus mirabilis HI4320 Pseudomonas putida KT2440 Pseudomonas fluorescens Pf0-1 Pseudomonas stutzeri A1501 Pseudomonas fluorescens SBW25 Pseudomonas putida GB-1 Rhizobium leguminosarum bv. viciae 3841 Rhizobium leguminosarum bv. trifolii WSM2304 Rothia mucilaginosa DY-18 Rothia dentocariosa ATCC 17931 Salmonella enterica subsp. enterica serovar Typhimurium str. LT2 Salmonella enterica subsp. enterica serovar Newport str. SL254 Salmonella enterica subsp. enterica serovar Heidelberg str. SL476 Salmonella enterica subsp. enterica serovar Agona str. SL483 Salmonella enterica subsp. enterica serovar Dublin str. CT02021853 Shigella sonnei Ss046 Shigella dysenteriae Sd197 Shigella flexneri 5 str. 8401 Spirosoma linguale DSM 74 Staphylococcus aureus subsp. aureus Mu50 Staphylococcus aureus subsp. aureus COL Staphylococcus aureus subsp. aureus MRSA252 Staphylococcus epidermidis RP62A Staphylococcus epidermidis ATCC 12228 Staphylococcus haemolyticus JCSC1435 Staphylococcus saprophyticus subsp. saprophyticus ATCC 15305 Staphylococcus aureus subsp. aureus NCTC 8325 Stenotrophomonas maltophilia K279a Stenotrophomonas maltophilia R551-3 Streptococcus agalactiae 2603V/R Streptococcus mutans UA159 Streptococcus agalactiae NEM316 Streptococcus thermophilus LMG 18311 Streptococcus pneumoniae D39 Streptococcus sanguinis SK36 Streptococcus gordonii str. Challis substr. CH1 Streptococcus pneumoniae Hungary19A-6 Streptococcus uberis 0140J Streptococcus pneumoniae JJA Streptococcus equi subsp. equi 4047 Streptococcus oralis Uo5 Vibrio parahaemolyticus RIMD 2210633 Yersinia enterocolitica subsp. enterocolitica 8081 Yersinia pseudotuberculosis IP 31758 Bacteroides cellulosilyticus DSM 14838 Bacteroides eggerthii 1_2_48FAA Bacteroides fluxus YIT 12057 Bacteroides graminisolvens Bacteroides graminisolvens DSM 19988 = JCM 15093 Bacteroides intestinalis DSM 17393 Bacteroides nordii CL02T12C05 Bacteroides oleiciplenus YIT 12058 Bacteroides ovatus ATCC 8483 Bacteroides pyogenes DSM 20611 = JCM 6294 Bacteroides uniformis ATCC 8492 Bacteroides xylanisolvens SD CC 1b Bacteroides sp. 1_1_14 Bacteroides sp. 1_1_30 Bacteroides sp. 2_1_22 Bacteroides sp. 2_2_4 Bacteroides sp. D2 Bacteroides sp. D20 Bacteroides sp. D22 Barnesiella intestinihominis YIT 11860 Paraprevotella clara YIT 11840 Paraprevotella xylaniphila YIT 11841 Parabacteroides johnsonii DSM 18315 Parabacteroides sp. D13 Bacteroides coprophilus DSM 18228 = JCM 13818 Bacteroides dorei DSM 17855 Spirosoma linguale Chlorobium limicola Bartonella quintana Beijerinckia indica Bradyrhizobium elkanii Methylobacterium mesophilicum Methylobacterium mesophilicum SR1.6/6 Rhizobium etli Azorhizobium caulinodans Xanthobacter autotrophicus Alcaligenes faecalis Burkholderia cepacia GG4 Lautropia mirabilis Lautropia mirabilis ATCC 51599 Laribacter hongkongensis Eikenella corrodens Eikenella corrodens ATCC 23834 Kingella oralis Kingella oralis ATCC 51147 Neisseria cinerea ATCC 14685 Neisseria elongata Neisseria elongata subsp. glycolytica ATCC 29315 Neisseria macacae Neisseria macacae ATCC 33926 Neisseria meningitidis Neisseria mucosa ATCC 25996 Neisseria subflava NJ9703 Nitrosospira multiformis Methyloversatilis universalis Methyloversatilis universalis FAM5 Desulfococcus oleovorans Bilophila wadsworthia 3_1_6 Desulfovibrio piger ATCC 29098 Arcobacter butzleri Campylobacter gracilis RM3268 Campylobacter hyointestinalis Campylobacter upsaliensis JV21 Helicobacter bilis ATCC 43879 Helicobacter pullorum MIT 98-5489 Aeromonas caviae Aeromonas media Aeromonas veronii Succinatimonas hippei Succinatimonas hippei YIT 12066 Succinivibrio dextrinosolvens Allochromatium vinosum Cedecea davisae Cedecea davisae DSM 4568 Citrobacter amalonaticus Citrobacter amalonaticus Y19 Citrobacter freundii Citrobacter youngae ATCC 29220 Enterobacter hormaechei Escherichia albertii TW07627 Klebsiella aerogenes Salmonella Salmonella enterica subsp. enterica serovar Typhimurium Trabulsiella guamensis Trabulsiella guamensis ATCC 49490 Tatumella ptyseos Tatumella ptyseos ATCC 33301 Edwardsiella tarda Edwardsiella tarda ATCC 23685 Hafnia alvei Hafnia alvei ATCC 51873 Morganella morganii Morganella morganii subsp. morganii KT Providencia rustigianii DSM 4541 Providencia stuartii ATCC 25827 Serratia marcescens subsp. marcescens Db11 Yersinia enterocolitica Yersinia pestis Yersinia pseudotuberculosis Plesiomonas shigelloides 302-73 Legionella pneumophila Actinobacillus pleuropneumoniae Haemophilus haemolyticus Haemophilus sputorum Francisella tularensis Grimontia hollisae CIP 101886 Vibrio fluvialis Vibrio fluvialis PG41 Vibrio parahaemolyticus Vibrio mimicus Leptospira interrogans Acetomicrobium hydrogeniformans Actinomyces naeslundii Actinomyces naeslundii str. Howell 279 Actinomyces urogenitalis DSM 15434 Actinomyces viscosus C505 Trueperella pyogenes Bifidobacterium gallicum DSM 20093 = LMG 11596 Bifidobacterium mongoliense Scardovia inopinata F0304 Corynebacterium amycolatum Corynebacterium aurimucosum Corynebacterium durum Corynebacterium durum F0235 Corynebacterium tuberculostearicum Corynebacterium tuberculostearicum SK141 Rothia aeria F0474 Cellulosimicrobium cellulans Propionibacterium Thermomonospora curvata Atopobium minutum 10063974 Olsenella profusa F0195 Collinsella intestinalis DSM 13280 Slackia exigua ATCC 700122 Slackia piriformis YIT 12062 Bacillus altitudinis Bacillus infantis NRRL B-14911 Bacillus firmus DS1 Lactobacillus paracasei subsp. paracasei 8700:2 Lactobacillus rhamnosus LMS2-1 Lactobacillus ultunensis DSM 16047 Lactobacillus hilgardii DSM 20176 = ATCC 8290 Lactobacillus reuteri CF48-3A Leuconostoc lactis Leuconostoc mesenteroides subsp. cremoris ATCC 19254 Oenococcus oeni Streptococcus constellatus subsp. pharyngis SK1060 = CCUG 46377 Streptococcus australis ATCC 700641 Streptococcus equi subsp. zooepidemicus H70 Streptococcus equi subsp. zooepidemicus MGCS10565 Streptococcus equinus ATCC 9812 Streptococcus infantis ATCC 700779 Streptococcus vestibularis F0396 Clostridium celatum DSM 1785 Clostridium sartagoforme AAU1 Anaerofustis stercorihominis Anaerofustis stercorihominis DSM 17244 Peptostreptococcus stomatis DSM 17678 Mogibacterium timidum Mogibacterium timidum ATCC 33093 [Clostridium] innocuum 2959 Clostridium spiroforme Holdemania filiformis DSM 12042 Solobacterium moorei F0204 Acidaminococcus intestini Phascolarctobacterium succinatutens YIT 12067 Dialister invisus DSM 15470 Megasphaera elsdenii Streptomyces coelicolor A3(2) Bordetella pertussis Tohama I Bordetella parapertussis 12822 Ralstonia eutropha H16 Xanthomonas campestris pv. campestris str. ATCC 33913 Xanthomonas campestris pv. campestris str. B100 Xanthomonas campestris pv. campestris str. 8004 Vibrio cholerae M66-2 Vibrio cholerae O1 biovar El Tor str. N16961 Corynebacterium glutamicum ATCC 13032 Clostridioides difficile 630 Clostridioides difficile NAP08 Shewanella frigidimarina NCIMB 400 Bacillus cytotoxicus NVH 391-98 Eggerthella sp. YY7918 Leuconostoc citreum KM20 Streptococcus mitis B6 Streptococcus parasanguinis ATCC 15912 Streptococcus parasanguinis FW213 Streptococcus pasteurianus ATCC 43144 Streptococcus suis GZ1 Acidothermus cellulolyticus 11B Alicyclobacillus acidocaldarius subsp. acidocaldarius DSM 446 Anoxybacillus flavithermus WK1 Bacillus selenitireducens MLS10 Beutenbergia cavernae DSM 12333 Caldicellulosiruptor bescii DSM 6725 Catenulispora acidiphila DSM 44928 Clostridium novyi NT Clostridium thermocellum ATCC 27405 Clostridium kluyveri DSM 555 Clostridium kluyveri NBRC 12016 Corynebacterium glutamicum R Corynebacterium urealyticum DSM 7109 Corynebacterium resistens DSM 45100 Deinococcus radiodurans R1 Deinococcus geothermalis DSM 11300 Deinococcus proteolyticus MRP Desulfotomaculum reducens MI-1 Frankia alni ACN14a Gardnerella vaginalis ATCC 14019 Geobacillus kaustophilus HTA426 Leuconostoc kimchii IMSNU 11154 Macrococcus caseolyticus JCSC5402 Meiothermus ruber DSM 1279 Mycobacterium bovis AF2122/97 Mycobacterium ulcerans Agy99 Mycobacterium vanbaalenii PYR-1 Mycobacterium bovis BCG str. Pasteur 1173P2 Mycobacterium tuberculosis H37Ra Mycobacterium sp. Spyr1 Mycobacterium canettii CIPT 140010059 Natranaerobius thermophilus JW/NM-WN-LF Corynebacterium diphtheriae NCTC 13129 Oceanobacillus iheyensis HTE831 Caldicellulosiruptor saccharolyticus DSM 8903 Bacillus tusciae DSM 2912 Oenococcus oeni PSU-1 Pelotomaculum thermopropionicum SI Saccharomonospora viridis DSM 43017 Slackia heliotrinireducens DSM 20476 Staphylococcus carnosus subsp. carnosus TM300 Streptococcus equi subsp. zooepidemicus Streptococcus suis BM407 Streptococcus gallolyticus UCN34 Thermobispora bispora DSM 43833 Thermomonospora curvata DSM 43183 Paraburkholderia graminis C4D1M Schaalia odontolytica ATCC 17982 Schaalia turicensis ACS-279-V-Col4 Acidipropionibacterium acidipropionici ATCC 4875 Leuconostoc mesenteroides subsp. cremoris Absiella dolichum DSM 3991 Holdemanella biformis DSM 3989 Bacteroides helcogenes P 36-108 Bacteroides salanitronis DSM 18170 Klebsiella aerogenes KCTC 2190 Halanaerobium hydrogeniformans Acaryochloris marina MBIC11017 Acidiphilium cryptum JF-5 Acidiphilium multivorum AIU301 Acidovorax citrulli AAC00-1 Acidovorax sp. JS42 Acidovorax ebreus TPSY Aeromonas salmonicida subsp. salmonicida A449 Agrobacterium vitis S4 Agrobacterium radiobacter K84 Rhodoferax ferrireducens T118 Alcanivorax borkumensis SK2 Alicycliphilus denitrificans K601 Vibrio fischeri MJ11 Aliivibrio salmonicida LFI1238 Alkalilimnicola ehrlichii MLHE-1 Arcobacter nitrofigilis DSM 7299 Azorhizobium caulinodans ORS 571 Azotobacter vinelandii DJ Bartonella tribocorum CIP 105476 Bartonella grahamii as4aup Mannheimia succiniciproducens MBEL55E Beijerinckia indica subsp. indica ATCC 9039 Bordetella petrii DSM 12804 Bordetella avium 197N Bradyrhizobium sp. ORS278 Bradyrhizobium sp. BTAi1 Brucella melitensis bv. 1 str. 16M Brucella abortus bv. 1 str. 9-941 Brucella ovis ATCC 25840 Brucella canis ATCC 23365 Brucella suis ATCC 23445 Brucella abortus S19 Brucella melitensis ATCC 23457 Brucella microti CCM 4915 Burkholderia mallei ATCC 23344 Burkholderia pseudomallei 1710b Burkholderia sp. 383 Burkholderia xenovorans LB400 Burkholderia ambifaria AMMD Burkholderia mallei NCTC 10229 Burkholderia pseudomallei 1106a Burkholderia vietnamiensis G4 Burkholderia cenocepacia MC0-3 Burkholderia ambifaria MC40-6 Burkholderia phymatum STM815 Burkholderia phytofirmans PsJN Burkholderia cenocepacia J2315 Burkholderia rhizoxinica HKI 454 Candidatus Liberibacter asiaticus str. psy62 Candidatus Pelagibacter ubique HTCC1062 Caulobacter crescentus CB15 Caulobacter crescentus NA1000 Cellulophaga algicola DSM 14237 Cellvibrio japonicus Ueda107 Chitinophaga pinensis DSM 2588 Chlorobium tepidum TLS Chlorobium phaeobacteroides DSM 266 Chlorobium limicola DSM 245 Chloroherpeton thalassium ATCC 35110 Chromohalobacter salexigens DSM 3043 Citrobacter rodentium ICC168 Colwellia psychrerythraea 34H Cronobacter turicensis z3032 Cupriavidus metallidurans CH34 Cupriavidus taiwanensis LMG 19424 Cupriavidus necator N-1 Cytophaga hutchinsonii ATCC 33406 Desulfitobacterium hafniense Y51 Desulfitobacterium hafniense DCB-2 Desulfobacterium autotrophicum HRM2 Desulfococcus oleovorans Hxd3 Desulfomicrobium baculatum DSM 4028 Desulfotalea psychrophila LSv54 Desulfovibrio magneticus RS-1 Desulfovibrio salexigens DSM 2638 Dickeya dadantii Ech703 Dickeya zeae Ech1591 Dickeya dadantii Ech586 Dickeya dadantii 3937 Dinoroseobacter shibae DFL 12 Edwardsiella ictaluri 93-146 Enterobacter sp. 638 Enterobacter cloacae SCF1 Erwinia tasmaniensis Et1/99 Erwinia amylovora CFBP1430 Erwinia billingiae Eb661 Erythrobacter litoralis HTCC2594 Ferrimonas balearica DSM 9799 Francisella tularensis subsp. holarctica LVS Geobacter metallireducens GS-15 Geobacter uraniireducens Rf4 Geobacter lovleyi SZ Geobacter bemidjiensis Bem Geobacter sp. FRC-32 Geobacter sp. M18 Gluconacetobacter diazotrophicus PAl 5 Gluconobacter oxydans 621H Gramella forsetii KT0803 Granulibacter bethesdensis CGDNIH1 Hahella chejuensis KCTC 2396 Haliangium ochraceum DSM 14365 Halorhodospira halophila SL1 Halothermothrix orenii H 168 Helicobacter acinonychis str. Sheeba Helicobacter mustelae 12198 Helicobacter pylori B8 Helicobacter felis ATCC 49179 Helicobacter bizzozeronii CIII-1 Herminiimonas arsenicoxydans Hyphomonas neptunium ATCC 15444 Idiomarina loihiensis L2TR Ilyobacter polytropus DSM 2926 Jannaschia sp. CCS1 Janthinobacterium sp. Marseille Klebsiella pneumoniae 342 Leadbetterella byssophila DSM 17132 Legionella pneumophila subsp. pneumophila str. Philadelphia 1 Legionella pneumophila str. Lens Legionella longbeachae NSW150 Leifsonia xyli subsp. xyli str. CTCB07 Leptospira borgpetersenii serovar Hardjo-bovis JB197 Leptothrix cholodnii SP-6 Magnetospirillum magneticum AMB-1 Maricaulis maris MCS10 Marinobacter aquaeolei VT8 Marinomonas mediterranea MMB-1 Marinomonas posidonica IVIA-Po-181 Meiothermus silvanus DSM 9946 Methylibium petroleiphilum PM1 Methylobacillus flagellatus KT Methylobacterium chloromethanicum CM4 Methylobacterium nodulans ORS 2060 Methylobacterium extorquens AM1 Methylobacterium extorquens DM4 Methylocella silvestris BL2 Methylotenera mobilis JLW8 Methylovorus glucosetrophus SIP3-4 Microbacterium testaceum StLB037 Neisseria meningitidis alpha14 Neisseria lactamica 020-06 Nitrobacter winogradskyi Nb-255 Nitrobacter hamburgensis X14 Nitrosomonas eutropha C91 Nitrosospira multiformis ATCC 25196 Novosphingobium aromaticivorans DSM 12444 Bordetella bronchiseptica RB50 Geobacter sulfurreducens PCA Xanthomonas axonopodis pv. citri str. 306 Leptospira interrogans serovar Lai str. 56601 Nitrosomonas europaea ATCC 19718 Helicobacter hepaticus ATCC 51449 Chromobacterium violaceum ATCC 12472 Bdellovibrio bacteriovorus HD100 Leptospira interrogans serovar Copenhageni str. Fiocruz L1-130 Sodalis glossinidius str. 'morsitans' Syntrophomonas wolfei subsp. wolfei str. Goettingen Magnetococcus sp. MC-1 Sorangium cellulosum 'So ce 56' Opitutus terrae PB90-1 Leptospira biflexa serovar Patoc strain 'Patoc 1 (Paris)' Elusimicrobium minutum Pei191 Alteromonas macleodii str. 'Deep ecotype' Deferribacter desulfuricans SSM1 Denitrovibrio acetiphilus DSM 12809 Calditerrivibrio nitroreducens DSM 19672 Rhodobacter capsulatus SB1003 Pantoea ananatis LMG 20103 Paracoccus denitrificans PD1222 Parvibaculum lavamentivorans DS-1 Pectobacterium atrosepticum SCRI1043 Pectobacterium carotovorum subsp. carotovorum PC1 Pedobacter heparinus DSM 2366 Pelobacter carbinolicus DSM 2380 Pelobacter propionicus DSM 2379 Chlorobium luteolum DSM 273 Pelodictyon phaeoclathratiforme BU-1 Phenylobacterium zucineum HLK1 Photobacterium profundum SS9 Photorhabdus luminescens subsp. laumondii TTO1 Photorhabdus asymbiotica subsp. asymbiotica ATCC 43949 Pirellula staleyi DSM 6068 Polaromonas sp. JS666 Polaromonas naphthalenivorans CJ2 Polynucleobacter necessarius subsp. asymbioticus QLW-P1DMWA-1 Prosthecochloris aestuarii DSM 271 Pseudoalteromonas haloplanktis TAC125 Pseudomonas syringae pv. tomato str. DC3000 Pseudomonas syringae pv. phaseolicola 1448A Pseudomonas syringae pv. syringae B728a Pseudomonas entomophila L48 Pseudomonas fulva 12-X Psychrobacter arcticus 273-4 Psychrobacter cryohalolentis K5 Psychromonas ingrahamii 37 Ralstonia solanacearum GMI1000 Rhizobium etli CFN 42 Rhizobium etli CIAT 652 Rhizobium leguminosarum bv. trifolii WSM1325 Rhodopirellula baltica SH 1 Rhodopseudomonas palustris CGA009 Rhodopseudomonas palustris HaA2 Rhodopseudomonas palustris BisB5 Rhodospirillum centenum SW Roseobacter denitrificans OCh 114 Roseobacter litoralis Och 149 Ruegeria pomeroyi DSS-3 Ruegeria sp. TM1040 Saccharophagus degradans 2-40 Salmonella enterica subsp. enterica serovar Paratyphi A str. Sebaldella termitidis ATCC 33386 Shewanella oneidensis MR-1 Shewanella sp. ANA-3 Shewanella amazonensis SB2B Shewanella sp. W3-18-1 Shewanella baltica OS155 Shewanella loihica PV-4 Shewanella sediminis HAW-EB3 Shewanella pealeana ATCC 700345 Shewanella baltica OS195 Shewanella halifaxensis HAW-EB4 Shewanella woodyi ATCC 51908 Shewanella piezotolerans WP3 Shewanella violacea DSS12 Shigella flexneri 2a str. 301 Shigella boydii Sb227 Shigella boydii CDC 3083-94 Sinorhizobium meliloti 1021 Sinorhizobium medicae WSM419 Sphingobium japonicum UT26S Sphingomonas wittichii RW1 Sphingopyxis alaskensis RB2256 Spirochaeta thermophila DSM 6192 Synechococcus sp. PCC 7002 Syntrophobacter fumaroxidans MPOB Syntrophus aciditrophicus SB Taylorella equigenitalis MCE9 Teredinibacter turnerae T7901 Thermotoga neapolitana DSM 4359 Thioalkalivibrio sp. K90mix Thiobacillus denitrificans ATCC 25259 Tolumonas auensis DSM 9187 Variovorax paradoxus EPS Verminephrobacter eiseniae EF01-2 Vibrio vulnificus CMCP6 Vibrio vulnificus YJ016 Vibrio splendidus LGP32 Xanthobacter autotrophicus Py2 Xanthomonas oryzae pv. oryzae KACC10331 Xanthomonas campestris pv. vesicatoria str. 85-10 Xanthomonas oryzae pv. oryzae PXO99A Xenorhabdus bovienii SS-2004 Xenorhabdus nematophila ATCC 19061 Xylella fastidiosa 9a5c Xylella fastidiosa Temecula1 Xylella fastidiosa M23 Zunongwangia profunda SM-A87 Zymomonas mobilis subsp. pomaceae ATCC 29192 Sphingobacterium paucimobilis HER1398 Neisseria meningitidis serogroup C Atlantibacter hermannii NBRC 105704 Klebsiella michiganensis KCTC 1686 Chania multitudinisentens RB-25

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018591	Succinyl-CoA	Methylmalonyl-CoA	Methylmalonyl-CoA mutase	Interconversion of succinyl-CoA and methylmalonyl-CoA	PathBank	31602464
MMDBr0018592	Methylmalonyl-CoA	Propionyl-CoA	Methylmalonyl-CoA decarboxylase	Carboxylation	PathBank	31602464
MMDBr0025931	propanoyl-CoA	Methylmalonyl-CoA	Biotin-dependent acetyl-/propionyl-coenzyme A carboxylase beta5 subunit	Carboxylation	RHEA	34755880
MMDBr0038782	Methylmalonyl-CoA	Methylmalonic acid	Thioesterase TesA	Hydrolysis	RHEA	34755880

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Proteobacteria	131	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human sputum; Human pleural fluid plaque; Human unknown	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	85	Human feces; Human ; Human pleural fluid plaque; Human dental plaque; Human sputum; Human nasopharyngeal swab; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	121	Human feces; Human appendix biopsy; Human ; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	237	Human ; Human feces; Pig ; Human subgingival plaque; Cattle	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	5	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	3		Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	1	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

HMDB0001269

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022523

KNApSAcK ID

Not Available

Chemspider ID

388424

KEGG Compound ID

C00683

BioCyc ID

Not Available

BiGG ID

Wikipedia Link

METLIN ID

PubChem Compound

PDB ID

Not Available

ChEBI ID

15466

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Morrow G 3rd, Barness LA, Cardinale GJ, Abeles RH, Flaks JG: Congenital methylmalonic acidemia: enzymatic evidence for two forms of the disease. Proc Natl Acad Sci U S A. 1969 May;63(1):191-7. doi: 10.1073/pnas.63.1.191. [PubMed:5257962 ]
Shevell MI, Matiaszuk N, Ledley FD, Rosenblatt DS: Varying neurological phenotypes among muto and mut- patients with methylmalonylCoA mutase deficiency. Am J Med Genet. 1993 Mar 1;45(5):619-24. doi: 10.1002/ajmg.1320450521. [PubMed:7681251 ]
Ludwig ML, Matthews RG: Structure-based perspectives on B12-dependent enzymes. Annu Rev Biochem. 1997;66:269-313. doi: 10.1146/annurev.biochem.66.1.269. [PubMed:9242908 ]
Gu P, Welch WH, Guo L, Schegg KM, Blomquist GJ: Characterization of a novel microsomal fatty acid synthetase (FAS) compared to a cytosolic FAS in the housefly, Musca domestica. Comp Biochem Physiol B Biochem Mol Biol. 1997 Oct;118(2):447-56. doi: 10.1016/s0305-0491(97)00112-0. [PubMed:9440236 ]
Rincon A, Aguado C, Desviat LR, Sanchez-Alcudia R, Ugarte M, Perez B: Propionic and methylmalonic acidemia: antisense therapeutics for intronic variations causing aberrantly spliced messenger RNA. Am J Hum Genet. 2007 Dec;81(6):1262-70. doi: 10.1086/522376. [PubMed:17966092 ]
Loewy AD, Niles KM, Anastasio N, Watkins D, Lavoie J, Lerner-Ellis JP, Pastinen T, Trasler JM, Rosenblatt DS: Epigenetic modification of the gene for the vitamin B(12) chaperone MMACHC can result in increased tumorigenicity and methionine dependence. Mol Genet Metab. 2009 Apr;96(4):261-7. doi: 10.1016/j.ymgme.2008.12.011. Epub 2009 Feb 5. [PubMed:19200761 ]
Quadros EV: Advances in the understanding of cobalamin assimilation and metabolism. Br J Haematol. 2010 Jan;148(2):195-204. doi: 10.1111/j.1365-2141.2009.07937.x. Epub 2009 Oct 12. [PubMed:19832808 ]
Watkins D, Rosenblatt DS: Inborn errors of cobalamin absorption and metabolism. Am J Med Genet C Semin Med Genet. 2011 Feb 15;157C(1):33-44. doi: 10.1002/ajmg.c.30288. Epub 2011 Feb 10. [PubMed:21312325 ]

Showing metabocard for Methylmalonyl-CoA (MMDBc0031995)

MOL for #<Metabolite:0x00007f9ac4a15700>

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