MiMeDB: Showing metabocard for malonyl-CoA methyl ester (MMDBc0031784)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 01:49:11 UTC

Update Date

2022-08-31 18:24:43 UTC

Metabolite ID

MMDBc0031784

Metabolite Identification

Common Name

malonyl-CoA methyl ester

Description

Malonyl-CoA methyl ester is an intermediate in biotin synthesis. It a substrate for the enzyme Malonyl-CoA O-methyltransferase BioC which onverts the free carboxyl group of a malonyl-thioester to its methyl ester by transfer of a methyl group from S-adenosyl-L-methionine (SAM). It allows to synthesize pimeloyl-ACP via the fatty acid synthetic pathway. E.coli employs a methylation and demethylation strategy to allow elongation of a temporarily disguised malonate moiety to a pimelate moiety by the fatty acid synthetic enzymes.

Structure

MOL SDF PDB SMILES InChI

 
  Mrv0541 07101213512D          
 
 55 57  0  0  1  0            999 V2000
    8.3325  -14.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6725  -14.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125  -14.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6725  -13.2413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3113  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0750  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7763  -14.4375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4775  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2200  -14.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9213  -14.0250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6225  -14.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3650  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0663  -14.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7675  -14.0250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5100  -14.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2113  -14.0250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.9125  -14.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6138  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3563  -14.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0750  -13.2413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6225  -15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5100  -15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2113  -13.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9125  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9125  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1813  -14.4375    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.0063  -14.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1813  -15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3450  -11.5088    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1700  -11.5088    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.4175  -10.7250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7575  -10.2300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0975  -10.7250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.2013  -10.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8500  -12.1688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6650  -12.1688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4900  -12.1688    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.4900  -11.3438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3150  -12.1688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4900  -12.9938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6638   -9.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6638  -10.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1075  -10.4775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1075   -9.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3650   -9.2400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9625   -9.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2200   -9.6525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2200  -10.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9625  -10.8900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9625   -8.4150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3563  -10.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1813  -10.7250    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.1813   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0063  -10.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1813  -12.6225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  3  5  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  6 20  2  0  0  0  0
 11 21  2  0  0  0  0
 15 22  2  0  0  0  0
 16 23  1  6  0  0  0
 17 24  1  0  0  0  0
 17 25  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 33  1  0  0  0  0
 31 34  1  6  0  0  0
 29 35  1  1  0  0  0
 30 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  2  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 41 45  1  0  0  0  0
 41 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 42 49  1  0  0  0  0
 46 50  1  0  0  0  0
 33 43  1  6  0  0  0
 34 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  2  0  0  0  0
 52 55  1  0  0  0  0
 26 55  1  0  0  0  0
M  END

 
  Mrv0541 07101213512D          
 
 55 57  0  0  1  0            999 V2000
    8.3325  -14.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6725  -14.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0125  -14.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6725  -13.2413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3113  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0750  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7763  -14.4375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   10.4775  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2200  -14.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9213  -14.0250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.6225  -14.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3650  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0663  -14.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7675  -14.0250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5100  -14.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2113  -14.0250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.9125  -14.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6138  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3563  -14.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0750  -13.2413    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6225  -15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5100  -15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2113  -13.2000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.9125  -13.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9125  -15.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1813  -14.4375    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.0063  -14.4375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1813  -15.2625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.3450  -11.5088    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.1700  -11.5088    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.4175  -10.7250    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.7575  -10.2300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0975  -10.7250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   17.2013  -10.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8500  -12.1688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6650  -12.1688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4900  -12.1688    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   17.4900  -11.3438    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.3150  -12.1688    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.4900  -12.9938    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6638   -9.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6638  -10.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1075  -10.4775    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1075   -9.6525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3650   -9.2400    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9625   -9.2400    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2200   -9.6525    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.2200  -10.4775    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9625  -10.8900    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.9625   -8.4150    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.3563  -10.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1813  -10.7250    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   19.1813   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.0063  -10.7250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1813  -12.6225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  3  5  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  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
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
  6 20  2  0  0  0  0
 11 21  2  0  0  0  0
 15 22  2  0  0  0  0
 16 23  1  6  0  0  0
 17 24  1  0  0  0  0
 17 25  1  0  0  0  0
 19 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 29 33  1  0  0  0  0
 31 34  1  6  0  0  0
 29 35  1  1  0  0  0
 30 36  1  1  0  0  0
 36 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  2  0  0  0  0
 41 42  2  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 41 45  1  0  0  0  0
 41 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 48 49  2  0  0  0  0
 42 49  1  0  0  0  0
 46 50  1  0  0  0  0
 33 43  1  6  0  0  0
 34 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 52 54  2  0  0  0  0
 52 55  1  0  0  0  0
 26 55  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0031784

> <DATABASE_NAME>
MIME

> <SMILES>
COC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](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/c1-25(2,20(37)23(38)28-5-4-14(33)27-6-7-55-16(35)8-15(34)46-3)10-48-54(44,45)51-53(42,43)47-9-13-19(50-52(39,40)41)18(36)24(49-13)32-12-31-17-21(26)29-11-30-22(17)32/h11-13,18-20,24,36-37H,4-10H2,1-3H3,(H,27,33)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,18-,19-,20+,24-/m1/s1

> <INCHI_KEY>
CHQAJZULNPRMEN-ITIYDSSPSA-N

> <FORMULA>
C25H40N7O19P3S

> <MOLECULAR_WEIGHT>
867.607

> <EXACT_MASS>
867.131252359

> <JCHEM_ACCEPTOR_COUNT>
18

> <JCHEM_AVERAGE_POLARIZABILITY>
74.61164751929988

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
-0.48

> <JCHEM_LOGP>
-6.937088367966353

> <ALOGPS_LOGS>
-2.34

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.8334045176178528

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8252479627216065

> <JCHEM_PKA_STRONGEST_BASIC>
4.946047024039826

> <JCHEM_POLAR_SURFACE_AREA>
389.9299999999999

> <JCHEM_REFRACTIVITY>
183.3212

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.96e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3R)-3-hydroxy-3-{[2-({2-[(3-methoxy-3-oxopropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxyphosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 10-JUL-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   10-JUL-12         0                                  
HETATM    1  C   UNK     0      15.554 -26.950   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.322 -26.257   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      13.090 -26.950   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      14.322 -24.717   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      11.781 -26.180   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.940 -26.180   0.000  0.00  0.00           C+0
HETATM    7  S   UNK     0      18.249 -26.950   0.000  0.00  0.00           S+0
HETATM    8  C   UNK     0      19.558 -26.180   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.944 -26.950   0.000  0.00  0.00           C+0
HETATM   10  N   UNK     0      22.253 -26.180   0.000  0.00  0.00           N+0
HETATM   11  C   UNK     0      23.562 -26.950   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.948 -26.180   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.257 -26.950   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      27.566 -26.180   0.000  0.00  0.00           N+0
HETATM   15  C   UNK     0      28.952 -26.950   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      30.261 -26.180   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      31.570 -26.950   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.879 -26.180   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      34.265 -26.950   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      16.940 -24.717   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      23.562 -28.490   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      28.952 -28.490   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      30.261 -24.640   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      31.570 -25.410   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      31.570 -28.490   0.000  0.00  0.00           C+0
HETATM   26  P   UNK     0      35.805 -26.950   0.000  0.00  0.00           P+0
HETATM   27  O   UNK     0      37.345 -26.950   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      35.805 -28.490   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      28.644 -21.483   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      30.184 -21.483   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      30.646 -20.020   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      29.414 -19.096   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      28.182 -20.020   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      32.109 -19.558   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      27.720 -22.715   0.000  0.00  0.00           O+0
HETATM   36  O   UNK     0      31.108 -22.715   0.000  0.00  0.00           O+0
HETATM   37  P   UNK     0      32.648 -22.715   0.000  0.00  0.00           P+0
HETATM   38  O   UNK     0      32.648 -21.175   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      34.188 -22.715   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      32.648 -24.255   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0      23.639 -18.018   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      23.639 -19.558   0.000  0.00  0.00           C+0
HETATM   43  N   UNK     0      26.334 -19.558   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      26.334 -18.018   0.000  0.00  0.00           C+0
HETATM   45  N   UNK     0      24.948 -17.248   0.000  0.00  0.00           N+0
HETATM   46  C   UNK     0      22.330 -17.248   0.000  0.00  0.00           C+0
HETATM   47  N   UNK     0      20.944 -18.018   0.000  0.00  0.00           N+0
HETATM   48  C   UNK     0      20.944 -19.558   0.000  0.00  0.00           C+0
HETATM   49  N   UNK     0      22.330 -20.328   0.000  0.00  0.00           N+0
HETATM   50  N   UNK     0      22.330 -15.708   0.000  0.00  0.00           N+0
HETATM   51  O   UNK     0      34.265 -20.020   0.000  0.00  0.00           O+0
HETATM   52  P   UNK     0      35.805 -20.020   0.000  0.00  0.00           P+0
HETATM   53  O   UNK     0      35.805 -18.480   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      37.345 -20.020   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      35.805 -23.562   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2    5                                                       
CONECT    4    2                                                            
CONECT    5    3                                                            
CONECT    6    1    7   20                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   21                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17   23                                                  
CONECT   17   16   18   24   25                                             
CONECT   18   17   19                                                       
CONECT   19   18   26                                                       
CONECT   20    6                                                            
CONECT   21   11                                                            
CONECT   22   15                                                            
CONECT   23   16                                                            
CONECT   24   17                                                            
CONECT   25   17                                                            
CONECT   26   19   27   28   55                                             
CONECT   27   26                                                            
CONECT   28   26                                                            
CONECT   29   30   33   35                                                  
CONECT   30   29   31   36                                                  
CONECT   31   30   32   34                                                  
CONECT   32   31   33                                                       
CONECT   33   32   29   43                                                  
CONECT   34   31   51                                                       
CONECT   35   29                                                            
CONECT   36   30   37                                                       
CONECT   37   36   38   39   40                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   37                                                            
CONECT   41   42   45   46                                                  
CONECT   42   41   43   49                                                  
CONECT   43   42   44   33                                                  
CONECT   44   43   45                                                       
CONECT   45   44   41                                                       
CONECT   46   41   47   50                                                  
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   42                                                       
CONECT   50   46                                                            
CONECT   51   34   52                                                       
CONECT   52   51   53   54   55                                             
CONECT   53   52                                                            
CONECT   54   52                                                            
CONECT   55   52   26                                                       
MASTER        0    0    0    0    0    0    0    0   55    0  114    0
END

Synonyms

Value	Source
(2R)-4-({[({[(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)-2-hydroxy-N-[2-({2-[(3-methoxy-3-oxopropanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidate	Generator
(2R)-4-({[({[(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)-2-hydroxy-N-[2-({2-[(3-methoxy-3-oxopropanoyl)sulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidate	Generator
(2R)-4-({[({[(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)-2-hydroxy-N-[2-({2-[(3-methoxy-3-oxopropanoyl)sulphanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]-3,3-dimethylbutanimidic acid	Generator

Molecular Formula

C₂₅H₄₀N₇O₁₉P₃S

Average Mass

867.607

Monoisotopic Mass

867.131252359

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-3-{[2-({2-[(3-methoxy-3-oxopropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3R)-3-hydroxy-3-{[2-({2-[(3-methoxy-3-oxopropanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-2,2-dimethylpropoxyphosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

CAS Registry Number

Not Available

SMILES

COC(=O)CC(=O)SCCNC(=O)CCNC(=O)[C@H](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/c1-25(2,20(37)23(38)28-5-4-14(33)27-6-7-55-16(35)8-15(34)46-3)10-48-54(44,45)51-53(42,43)47-9-13-19(50-52(39,40)41)18(36)24(49-13)32-12-31-17-21(26)29-11-30-22(17)32/h11-13,18-20,24,36-37H,4-10H2,1-3H3,(H,27,33)(H,28,38)(H,42,43)(H,44,45)(H2,26,29,30)(H2,39,40,41)/t13-,18-,19-,20+,24-/m1/s1

InChI Key

CHQAJZULNPRMEN-ITIYDSSPSA-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
Aminopyrimidine
Monoalkyl phosphate
Organic phosphoric acid derivative
N-substituted imidazole
N-acyl-amine
Phosphoric acid ester
Monosaccharide
Alkyl phosphate
Imidolactam
Pyrimidine
1,3-dicarbonyl compound
Fatty amide
Imidazole
Azole
Heteroaromatic compound
Tetrahydrofuran
Methyl ester
Carbothioic s-ester
Thiocarboxylic acid ester
Secondary carboxylic acid amide
Secondary alcohol
Carboxamide group
Carboxylic acid ester
Amino acid or derivatives
Thiocarboxylic acid or derivatives
Sulfenyl compound
Carboxylic acid derivative
Organoheterocyclic compound
Azacycle
Oxacycle
Monocarboxylic acid or derivatives
Organic oxygen compound
Amine
Organonitrogen compound
Carbonyl group
Organic nitrogen compound
Organosulfur compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Primary amine
Alcohol
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	3.96 g/L	ALOGPS
logP	-0.48	ALOGPS
logP	-6.9	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	18	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	389.93 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	183.32 m³·mol⁻¹	ChemAxon
Polarizability	74.61 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-1911000130-7ec4913dc885ca0c311c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0912000000-27289dd346d4bf2fa94c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2911000000-d9ea2c85350a03c21b68	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00o0-9821140460-6cd71ffedc1f6bf135fb	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-003r-5910010010-ec3af4a8c64ab1635995	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-7ce4f36975b302bc9c95	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-21	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0007664	S-Adenosylmethionine	S-Adenosylhomocysteine	Not Available		VMH	30371894

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	2	Human feces; Human ; Human feces; pleural fluid plaque; bal; Human stool	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Proteobacteria	34	Human feces; Human ; Human feces; pleural fluid plaque; bal; Human stool	Unknown; Metabolic reconstruction
Bacteria/Eubacteria	Verrucomicrobia	1	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Firmicutes	2	Human ; Human feces	Metabolic reconstruction
Bacteria/Eubacteria	Bacteroidetes	45	Human feces; Human ; Human stool; Human saliva	Metabolic reconstruction
Bacteria/Eubacteria	Fusobacteria	14	Human feces	Metabolic reconstruction

Exposure Sources

Other Exposures

Source Type	Activity	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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

46926156

PDB ID

Not Available

ChEBI ID

Not Available

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 malonyl-CoA methyl ester (MMDBc0031784)

MOL for #<Metabolite:0x000055eeeb9df050>

3D MOL for #<Metabolite:0x000055eeeb9df050>

3D SDF for #<Metabolite:0x000055eeeb9df050>

3D-SDF for #<Metabolite:0x000055eeeb9df050>

PDB for #<Metabolite:0x000055eeeb9df050>

3D PDB for #<Metabolite:0x000055eeeb9df050>

SMILES for #<Metabolite:0x000055eeeb9df050>

INCHI for #<Metabolite:0x000055eeeb9df050>

Structure for #<Metabolite:0x000055eeeb9df050>

3D Structure for #<Metabolite:0x000055eeeb9df050>