MiMeDB: Showing metabocard for 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate (MMDBc0029823)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:43:12 UTC

Update Date

2022-08-31 17:18:53 UTC

Metabolite ID

MMDBc0029823

Metabolite Identification

Common Name

5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate

Description

5-amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate is an intermediate in purine metabolism. 5-amino-1-(5-phospho-D-ribosyl) imidazole-4-carboxylate is converted from aminoimidazole ribotide via phosphoribosylaminoimidazole carboxylase [EC: 4.1.1.21].

Structure

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

HMDB0006273
     RDKit          3D
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
    2.8364    1.6281    1.4030 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0687    0.6231    0.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2478    0.3787   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875    1.1387   -0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5295    2.0972    0.7474 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6364    0.8450   -0.7687 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0203   -0.6685   -1.0445 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7258   -1.0580   -0.8709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1454   -0.2632    0.0433 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7976   -0.3845    0.4693 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0450   -0.8394   -0.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763   -0.8139    0.0858 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4313   -0.9935   -0.8667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6008   -0.9471   -0.0745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9854   -1.1407   -1.0497 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.6882   -1.9756   -2.2659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5212    0.3891   -1.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2257   -1.8134   -0.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3227    0.6280    0.5684 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1604    0.8070    1.6422 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1465    0.8572    0.9375 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1961    0.9031    2.3298 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944    2.6216    1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8824    1.4805    2.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1233    1.5105   -1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3180   -1.8938   -1.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6807   -1.1604    1.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3449   -1.4940    0.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3931   -2.0105   -1.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4644   -0.2369   -1.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4823    1.0475   -0.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8439   -2.2539    0.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6170    1.2366   -0.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3904   -0.0121    2.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4477    1.7799    0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0914   -0.0125    2.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 12 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  9  2  1  0
 21 10  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  8 26  1  0
 10 27  1  1
 12 28  1  1
 13 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  6
 20 34  1  0
 21 35  1  6
 22 36  1  0
M  END


  Mrv1652309042000322D          

 22 23  0  0  0  0            999 V2000
10001.7525 9999.2289    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10003.152210000.1468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.868710000.5597    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.1522 9999.3209    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10000.5881 9998.6981    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.330910000.5597    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7981 9998.7063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9997.615710000.1468    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.900310000.5597    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
 9997.312410001.2761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.181210000.1447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.486610001.2761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.711410000.6408    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9999.044010000.1558    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9999.2989 9999.3712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.1239 9999.3712    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10000.378810000.1558    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
10001.770610000.0655    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.438010000.5505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.183110001.3351    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.358110001.3351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.103210000.5505    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 11  1  0  0  0  0
  9 12  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 18 19  2  0  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 18 22  1  0  0  0  0
 21 22  1  0  0  0  0
 16  5  1  6  0  0  0
 14  6  1  1  0  0  0
 15  7  1  6  0  0  0
  1 18  1  0  0  0  0
 17 22  1  1  0  0  0
 19  2  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029823

> <DATABASE_NAME>
MIME

> <SMILES>
NC1=C(N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C(O)=O

> <INCHI_IDENTIFIER>
InChI=1S/C9H14N3O9P/c10-7-4(9(15)16)11-2-12(7)8-6(14)5(13)3(21-8)1-20-22(17,18)19/h2-3,5-6,8,13-14H,1,10H2,(H,15,16)(H2,17,18,19)/t3-,5-,6-,8-/m1/s1

> <INCHI_KEY>
XFVULMDJZXYMSG-ZIYNGMLESA-N

> <FORMULA>
C9H14N3O9P

> <MOLECULAR_WEIGHT>
339.1959

> <EXACT_MASS>
339.046765573

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
28.489435960826928

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazole-4-carboxylic acid

> <ALOGPS_LOGP>
-2.05

> <JCHEM_LOGP>
-3.7317525536992675

> <ALOGPS_LOGS>
-2.08

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-2

> <JCHEM_PKA>
2.25890510038018

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.1825891616118538

> <JCHEM_PKA_STRONGEST_BASIC>
7.112770228283477

> <JCHEM_POLAR_SURFACE_AREA>
197.59

> <JCHEM_REFRACTIVITY>
67.3199

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.81e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazole-4-carboxylic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0006273
     RDKit          3D
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
    2.8364    1.6281    1.4030 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0687    0.6231    0.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2478    0.3787   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875    1.1387   -0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5295    2.0972    0.7474 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6364    0.8450   -0.7687 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0203   -0.6685   -1.0445 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7258   -1.0580   -0.8709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1454   -0.2632    0.0433 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7976   -0.3845    0.4693 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0450   -0.8394   -0.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763   -0.8139    0.0858 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4313   -0.9935   -0.8667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6008   -0.9471   -0.0745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9854   -1.1407   -1.0497 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.6882   -1.9756   -2.2659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5212    0.3891   -1.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2257   -1.8134   -0.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3227    0.6280    0.5684 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1604    0.8070    1.6422 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1465    0.8572    0.9375 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1961    0.9031    2.3298 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944    2.6216    1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8824    1.4805    2.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1233    1.5105   -1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3180   -1.8938   -1.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6807   -1.1604    1.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3449   -1.4940    0.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3931   -2.0105   -1.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4644   -0.2369   -1.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4823    1.0475   -0.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8439   -2.2539    0.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6170    1.2366   -0.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3904   -0.0121    2.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4477    1.7799    0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0914   -0.0125    2.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 12 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  9  2  1  0
 21 10  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  8 26  1  0
 10 27  1  1
 12 28  1  1
 13 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  6
 20 34  1  0
 21 35  1  6
 22 36  1  0
M  END

HEADER    PROTEIN                                 04-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   04-SEP-20         0                                  
HETATM    1  N   UNK     0    8669.9388665.227   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0    8672.5518666.941   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0    8673.8888667.711   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8672.5518665.399   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8667.7648664.236   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0    8663.5518667.711   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0    8664.4238664.252   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0    8662.2168666.941   0.000  0.00  0.00           O+0
HETATM    9  P   UNK     0    8660.8818667.711   0.000  0.00  0.00           P+0
HETATM   10  O   UNK     0    8661.6508669.049   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0    8659.5388666.937   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0    8660.1088669.049   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0    8666.1288667.863   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8664.8828666.957   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8665.3588665.493   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8666.8988665.493   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8667.3748666.957   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8669.9728666.789   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8671.2188667.694   0.000  0.00  0.00           C+0
HETATM   20  N   UNK     0    8670.7428669.159   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0    8669.2028669.159   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0    8668.7268667.694   0.000  0.00  0.00           N+0
CONECT    1   18                                                            
CONECT    2    3    4   19                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5   16                                                            
CONECT    6    8   14                                                       
CONECT    7   15                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10   11   12                                             
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    9                                                            
CONECT   13   14   17                                                       
CONECT   14   15   13    6                                                  
CONECT   15   14   16    7                                                  
CONECT   16   15   17    5                                                  
CONECT   17   16   13   22                                                  
CONECT   18   19   22    1                                                  
CONECT   19   18   20    2                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   18   21   17                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   46    0
END

COMPND    HMDB0006273
HETATM    1  N1  UNL     1       2.836   1.628   1.403  1.00  0.00           N  
HETATM    2  C1  UNL     1       3.069   0.623   0.444  1.00  0.00           C  
HETATM    3  C2  UNL     1       4.248   0.379  -0.231  1.00  0.00           C  
HETATM    4  C3  UNL     1       5.487   1.139  -0.063  1.00  0.00           C  
HETATM    5  O1  UNL     1       5.529   2.097   0.747  1.00  0.00           O  
HETATM    6  O2  UNL     1       6.636   0.845  -0.769  1.00  0.00           O  
HETATM    7  N2  UNL     1       4.020  -0.668  -1.044  1.00  0.00           N  
HETATM    8  C4  UNL     1       2.726  -1.058  -0.871  1.00  0.00           C  
HETATM    9  N3  UNL     1       2.145  -0.263   0.043  1.00  0.00           N  
HETATM   10  C5  UNL     1       0.798  -0.385   0.469  1.00  0.00           C  
HETATM   11  O3  UNL     1      -0.045  -0.839  -0.567  1.00  0.00           O  
HETATM   12  C6  UNL     1      -1.276  -0.814   0.086  1.00  0.00           C  
HETATM   13  C7  UNL     1      -2.431  -0.993  -0.867  1.00  0.00           C  
HETATM   14  O4  UNL     1      -3.601  -0.947  -0.075  1.00  0.00           O  
HETATM   15  P1  UNL     1      -4.985  -1.141  -1.050  1.00  0.00           P  
HETATM   16  O5  UNL     1      -4.688  -1.976  -2.266  1.00  0.00           O  
HETATM   17  O6  UNL     1      -5.521   0.389  -1.590  1.00  0.00           O  
HETATM   18  O7  UNL     1      -6.226  -1.813  -0.116  1.00  0.00           O  
HETATM   19  C8  UNL     1      -1.323   0.628   0.568  1.00  0.00           C  
HETATM   20  O8  UNL     1      -2.160   0.807   1.642  1.00  0.00           O  
HETATM   21  C9  UNL     1       0.147   0.857   0.938  1.00  0.00           C  
HETATM   22  O9  UNL     1       0.196   0.903   2.330  1.00  0.00           O  
HETATM   23  H1  UNL     1       2.594   2.622   1.114  1.00  0.00           H  
HETATM   24  H2  UNL     1       2.882   1.480   2.443  1.00  0.00           H  
HETATM   25  H3  UNL     1       7.123   1.510  -1.350  1.00  0.00           H  
HETATM   26  H4  UNL     1       2.318  -1.894  -1.431  1.00  0.00           H  
HETATM   27  H5  UNL     1       0.681  -1.160   1.281  1.00  0.00           H  
HETATM   28  H6  UNL     1      -1.345  -1.494   0.935  1.00  0.00           H  
HETATM   29  H7  UNL     1      -2.393  -2.010  -1.297  1.00  0.00           H  
HETATM   30  H8  UNL     1      -2.464  -0.237  -1.650  1.00  0.00           H  
HETATM   31  H9  UNL     1      -5.482   1.047  -0.855  1.00  0.00           H  
HETATM   32  H10 UNL     1      -5.844  -2.254   0.687  1.00  0.00           H  
HETATM   33  H11 UNL     1      -1.617   1.237  -0.307  1.00  0.00           H  
HETATM   34  H12 UNL     1      -2.390  -0.012   2.134  1.00  0.00           H  
HETATM   35  H13 UNL     1       0.448   1.780   0.449  1.00  0.00           H  
HETATM   36  H14 UNL     1      -0.091  -0.013   2.636  1.00  0.00           H  
CONECT    1    2   23   24
CONECT    2    3    3    9
CONECT    3    4    7
CONECT    4    5    5    6
CONECT    6   25
CONECT    7    8    8
CONECT    8    9   26
CONECT    9   10
CONECT   10   11   21   27
CONECT   11   12
CONECT   12   13   19   28
CONECT   13   14   29   30
CONECT   14   15
CONECT   15   16   16   17   18
CONECT   17   31
CONECT   18   32
CONECT   19   20   21   33
CONECT   20   34
CONECT   21   22   35
CONECT   22   36
END

HMDB0006273
     RDKit          3D
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylic acid
 36 37  0  0  0  0  0  0  0  0999 V2000
    2.8364    1.6281    1.4030 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.0687    0.6231    0.4445 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2478    0.3787   -0.2305 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4875    1.1387   -0.0630 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5295    2.0972    0.7474 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6364    0.8450   -0.7687 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.0203   -0.6685   -1.0445 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7258   -1.0580   -0.8709 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1454   -0.2632    0.0433 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.7976   -0.3845    0.4693 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.0450   -0.8394   -0.5667 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2763   -0.8139    0.0858 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.4313   -0.9935   -0.8667 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6008   -0.9471   -0.0745 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9854   -1.1407   -1.0497 P   0  0  0  0  0  5  0  0  0  0  0  0
   -4.6882   -1.9756   -2.2659 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5212    0.3891   -1.5904 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2257   -1.8134   -0.1160 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3227    0.6280    0.5684 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.1604    0.8070    1.6422 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1465    0.8572    0.9375 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1961    0.9031    2.3298 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5944    2.6216    1.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8824    1.4805    2.4431 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1233    1.5105   -1.3501 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3180   -1.8938   -1.4314 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6807   -1.1604    1.2809 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3449   -1.4940    0.9352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3931   -2.0105   -1.2972 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4644   -0.2369   -1.6496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4823    1.0475   -0.8553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8439   -2.2539    0.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6170    1.2366   -0.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3904   -0.0121    2.1344 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4477    1.7799    0.4488 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0914   -0.0125    2.6358 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  3  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 15 17  1  0
 15 18  1  0
 12 19  1  0
 19 20  1  0
 19 21  1  0
 21 22  1  0
  9  2  1  0
 21 10  1  0
  1 23  1  0
  1 24  1  0
  6 25  1  0
  8 26  1  0
 10 27  1  1
 12 28  1  1
 13 29  1  0
 13 30  1  0
 17 31  1  0
 18 32  1  0
 19 33  1  6
 20 34  1  0
 21 35  1  6
 22 36  1  0
M  END

Synonyms

Value	Source
1-(5'-Phosphoribosyl)-4-carboxy-5-aminoimidazole	ChEBI
1-(5'-Phosphoribosyl)-5-amino-4-carboxyimidazole	ChEBI
1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxylate	ChEBI
1-(5-Phospho-D-ribosyl)-5-amino-4-imidazolecarboxylate	ChEBI
5'-Phosphoribosyl-4-carboxy-5-aminoimidazole	ChEBI
5'-Phosphoribosyl-5-amino-4-imidazolecarboxylate	ChEBI
5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate	ChEBI
1-(5'-Phosphoribosyl)-5-amino-4-imidazolecarboxylic acid	Generator
1-(5-Phospho-D-ribosyl)-5-amino-4-imidazolecarboxylic acid	Generator
5'-Phosphoribosyl-5-amino-4-imidazolecarboxylic acid	Generator
5-amino-1-(5-phospho-D-Ribosyl)imidazole-4-carboxylic acid	Generator
4-Carboxy-5-aminoimidazole ribonucleotide	HMDB
5'Phosphoribosyl-4-carboxy-5-aminoimidazole	HMDB
5-Amino-4-carboxyimidazole ribonucleotide	HMDB
5-amino-4-Imidazolecarboxylic acid ribonucleotide	HMDB, MeSH
5-Aminoimidazole carboxilic acid ribonucleotice	HMDB
5-Aminoimidazole-4-carboxilic acid ribonucleotide	HMDB
Carboxyaminoimidazole ribonucleotide	HMDB
Carboxy-AIR	MeSH, HMDB
AICOR	MeSH, HMDB
Carboxyaminoimidazole ribotide	MeSH, HMDB
CAIR	MeSH, HMDB
5-Amino-1-(5-O-phosphonopentofuranosyl)-1H-imidazole-4-carboxylic acid	MeSH, HMDB
1-(5’-Phosphoribosyl)-4-carboxy-5-aminoimidazole	HMDB
1-(5’-Phosphoribosyl)-5-amino-4-carboxyimidazole	HMDB
1-(5’-Phosphoribosyl)-5-amino-4-imidazolecarboxylate	HMDB
5-Amino-1-(5-O-phosphono-beta-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid	HMDB
5-Amino-1-(5-O-phosphono-β-D-ribofuranosyl)-1H-imidazole-4-carboxylic acid	HMDB
5-Aminoimidazole 4-carboxylic acid ribonucleotide	HMDB
5-Aminoimidazolecarboxylic acid ribonucleotide	HMDB
5’-Phosphoribosyl-4-carboxy-5-aminoimidazole	HMDB
5’-Phosphoribosyl-5-amino-4-imidazolecarboxylate	HMDB

Molecular Formula

C₉H₁₄N₃O₉P

Average Mass

339.1959

Monoisotopic Mass

339.046765573

IUPAC Name

5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1H-imidazole-4-carboxylic acid

Traditional Name

5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]imidazole-4-carboxylic acid

CAS Registry Number

Not Available

SMILES

NC1=C(N=CN1[C@@H]1O[C@H](COP(O)(O)=O)[C@@H](O)[C@H]1O)C(O)=O

InChI Identifier

InChI=1S/C9H14N3O9P/c10-7-4(9(15)16)11-2-12(7)8-6(14)5(13)3(21-8)1-20-22(17,18)19/h2-3,5-6,8,13-14H,1,10H2,(H,15,16)(H2,17,18,19)/t3-,5-,6-,8-/m1/s1

InChI Key

XFVULMDJZXYMSG-ZIYNGMLESA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pentose phosphates. These are carbohydrate derivatives containing a pentose substituted by one or more phosphate groups.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbohydrates and carbohydrate conjugates

Direct Parent

Pentose phosphates

Alternative Parents

Substituents

Pentose phosphate
Pentose-5-phosphate
Imidazole ribonucleoside
N-glycosyl compound
Glycosyl compound
Monosaccharide phosphate
Monoalkyl phosphate
Imidazole-4-carbonyl group
Alkyl phosphate
Phosphoric acid ester
Aminoimidazole
Organic phosphoric acid derivative
N-substituted imidazole
Azole
Vinylogous amide
Tetrahydrofuran
Imidazole
Heteroaromatic compound
1,2-diol
Secondary alcohol
Amino acid
Amino acid or derivatives
Oxacycle
Carboxylic acid derivative
Carboxylic acid
Azacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Alcohol
Organic nitrogen compound
Hydrocarbon derivative
Amine
Organopnictogen compound
Organic oxide
Primary amine
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

1-(phosphoribosyl)imidazole (CHEBI:28413 )
aminoimidazole (CHEBI:28413 )
imidazole-4-carboxylic acid (CHEBI:28413 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.81 g/L	ALOGPS
logP	-2	ALOGPS
logP	-3.7	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.18	ChemAxon
pKa (Strongest Basic)	7.11	ChemAxon
Physiological Charge	-2	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	197.59 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	67.32 m³·mol⁻¹	ChemAxon
Polarizability	28.49 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Cytoplasm

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
MMDBp0192512	Multifunctional protein ADE2	Enzyme	P22234	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0018511	N5-Carboxyaminoimidazole ribonucleotide	5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate	N5-carboxyaminoimidazole ribonucleotide mutase		PathBank	31602464
MMDBr0018512	L-Aspartic acid	SAICAR	Phosphoribosylaminoimidazole-succinocarboxamide synthase	Synthesis	PathBank	31602464
MMDBr0019209	5-Phosphoribosyl-5-carboxyaminoimidazole	5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate	N5-carboxyaminoimidazole ribonucleotide mutase		PathBank	31602464
MMDBr0019841	N5-Carboxyaminoimidazole ribonucleotide	5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate	Unknown Protein		PathBank	31602464
MMDBr0019842	L-Aspartic acid	SAICAR	Unknown Protein		PathBank	31602464

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	Proteobacteria	12	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Cattle ; River trout ; Rat ; Sheep ; Chicken ; American dog tick	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	438	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool; Catfish	Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	418	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human dental plaque; Human nasal swab; Human stool; Human feces; pleural fluid plaque; bal; Cattle ; River trout ; Rat ; Sheep ; Chicken ; American dog tick	Unknown; Metabolic reconstruction
Bacteria	Actinobacteria	15	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Actinobacteria	147	Human feces; Human sputum; Human bronchial brush; Human nasopharyngeal swab; Human pleural fluid plaque; Human dental plaque; Human ; Human supragingival plaque; Human mucosa; Human subgingival plaque; Human saliva; Cattle	Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	129	Human feces; Human appendix biopsy; Human ; Human stool; Human saliva; Human gastric fluid; Human urine; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria/Eubacteria	Synergistetes	3	Human feces	Metabolic reconstruction
Bacteria	Firmicutes	29	Human feces; Human pleural fluid plaque; Pig ; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Human supragingival plaque; Cattle ; Human stool; Catfish	Metabolic reconstruction
Bacteria/Eubacteria	Spirochaetes	4	Human feces; Human	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	20	Human feces; Human	Metabolic reconstruction
Archaea	Euryarchaeota	6	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Planctomycetes	2	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria	Synergistetes	1	Human feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	12	Human feces; Human saliva; Human supragingival plaque	Unknown
Eukaryota/Fungi	Basidiomycota	3
Archaea/Archaea	Euryarchaeota	18	Human feces; Human	Metabolic reconstruction
Bacteria/Eubacteria	Aquificae	2
Bacteria	nah	1
Bacteria/Eubacteria	Thermotogae	3
Bacteria/Eubacteria	Cyanobacteria	23
Archaea/Archaea	Crenarchaeota	5		Metabolic reconstruction
Archaea/Archaea	Thaumarchaeota	2		Metabolic reconstruction
Bacteria/Eubacteria	Chloroflexi	6
Bacteria/Eubacteria	Chlorobi	11
Bacteria/Eubacteria	Deinococcus-thermus	3
Bacteria/Eubacteria	Elusimicrobia	1
Bacteria/Eubacteria	Nitrospirae	1

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

HMDB0006273

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023871

KNApSAcK ID

Not Available

Chemspider ID

144983

KEGG Compound ID

C04751

BioCyc ID

PHOSPHORIBOSYL-CARBOXY-AMINOIMIDAZOLE

BiGG ID

44477

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

165388

PDB ID

C2R

ChEBI ID

28413

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for 5-Amino-1-(5-phospho-D-ribosyl)imidazole-4-carboxylate (MMDBc0029823)

MOL for #<Metabolite:0x00007f923891ba28>

3D MOL for #<Metabolite:0x00007f923891ba28>

3D SDF for #<Metabolite:0x00007f923891ba28>

3D-SDF for #<Metabolite:0x00007f923891ba28>

PDB for #<Metabolite:0x00007f923891ba28>

3D PDB for #<Metabolite:0x00007f923891ba28>

SMILES for #<Metabolite:0x00007f923891ba28>

INCHI for #<Metabolite:0x00007f923891ba28>

Structure for #<Metabolite:0x00007f923891ba28>

3D Structure for #<Metabolite:0x00007f923891ba28>