MiMeDB: Showing metabocard for Crotonoyl-CoA (MMDBc0029676)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-17 23:37:07 UTC

Update Date

2023-12-14 16:53:06 UTC

Metabolite ID

MMDBc0029676

Metabolite Identification

Common Name

Crotonoyl-CoA

Description

Crotonoyl-CoA is an important component in several metabolic pathways, notably fatty acid and amino acid metabolism. It is the substrate of a group of enzymes acyl-Coenzyme A oxidases 1, 2, 3 (E.C.: 1.3.3.6) corresponding to palmitoyl, branched chain, and pristanoyl, respectively, in the peroxisomal fatty acid beta-oxidation, producing hydrogen peroxide. It is also a substrate of a group of enzymes called acyl-Coenzyme A dehydrogenase (E.C.:1.3.99-, including 1.3.99.2, 1.3.99.3) in the metabolism of fatty acids. In addition, crotonoyl-CoA is the substrate of enoyl coenzyme A hydratase (E.C.4.2.1.17) during lysine degradation and tryptophan metabolism, benzoate degradation via CoA ligation; in contrast it is the product of this enzyme in the butanoate metabolism. Moreover, it is produced from multiple enzymes in the butanoate metabolism pathway, including 3-Hydroxybutyryl-CoA dehydratase (E.C.:4.2.1.55), glutaconyl-CoA decarboxylase (E.C.: 4.1.1.70), vinylacetyl-CoA delta-isomerase (E.C.: 5.3.3.3), and trans-2-enoyl-CoA reductase (NAD+) (E.C.: 1.3.1.44). In lysine degradation and tryptophan metabolism, crotonoyl CoA is produced by glutaryl-Coenzyme A dehydrogenase (E.C.:1.3.99.7) lysine and tryptophan metabolic pathway.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02231219192D          

 53 55  0  0  1  0            999 V2000
   12.8179   -5.3302    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.9860  -11.2510    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.0463  -12.2089    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.7277  -12.9039    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.7927  -11.4240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1794  -11.0781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2999  -12.9940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8126  -13.7245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1589  -10.4444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2612  -12.4626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6429  -12.0833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5484  -12.8191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7594  -10.5593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8094  -15.5193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8739  -14.6186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8131  -12.0576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8313  -11.9555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9071  -12.9887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6121   -8.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4915   -6.6341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4582   -5.7695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2523   -8.9893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1317   -7.0733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6064  -18.3849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1015  -16.0710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1015  -17.3988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8920  -17.1474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6064  -15.9099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1191  -10.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3124   -9.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0716   -6.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9258  -10.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8782   -6.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987   -8.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1066  -13.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1920   -8.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9463  -10.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2920   -9.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6974   -3.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3577  -15.2869    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.3600  -13.9520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.1428  -15.0333    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.1442  -14.2083    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.0589   -9.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9384   -7.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0112   -5.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9510   -4.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7577   -4.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6064  -17.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3209  -16.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3209  -17.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5830  -16.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8920  -16.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 31  1  0  0  0  0
  1 46  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  9  1  0  0  0  0
  2 16  2  0  0  0  0
  3  5  1  0  0  0  0
  3  7  1  0  0  0  0
  3 10  1  0  0  0  0
  3 17  2  0  0  0  0
  4  8  1  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  4 18  2  0  0  0  0
  6 32  1  0  0  0  0
  7 35  1  0  0  0  0
 43  8  1  1  0  0  0
 13 30  1  0  0  0  0
 42 14  1  1  0  0  0
 15 40  1  0  0  0  0
 15 41  1  0  0  0  0
 19 44  2  0  0  0  0
 20 45  2  0  0  0  0
 21 46  2  0  0  0  0
 22 34  1  0  0  0  0
 22 44  1  0  0  0  0
 23 33  1  0  0  0  0
 23 45  1  0  0  0  0
 24 49  1  0  0  0  0
 40 25  1  6  0  0  0
 25 50  1  0  0  0  0
 25 52  1  0  0  0  0
 26 51  1  0  0  0  0
 26 52  2  0  0  0  0
 27 49  1  0  0  0  0
 27 53  2  0  0  0  0
 28 50  2  0  0  0  0
 28 53  1  0  0  0  0
 29 30  1  0  0  0  0
 29 32  1  0  0  0  0
 29 37  1  0  0  0  0
 29 38  1  0  0  0  0
 30 44  1  0  0  0  0
 31 33  1  0  0  0  0
 34 36  1  0  0  0  0
 41 35  1  6  0  0  0
 36 45  1  0  0  0  0
 39 47  1  0  0  0  0
 40 42  1  0  0  0  0
 41 43  1  0  0  0  0
 42 43  1  0  0  0  0
 46 48  1  0  0  0  0
 47 48  2  0  0  0  0
 49 51  2  0  0  0  0
 50 51  1  0  0  0  0
M  END


  Mrv0541 02231219192D          

 53 55  0  0  1  0            999 V2000
   12.8179   -5.3302    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.9860  -11.2510    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.0463  -12.2089    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   23.7277  -12.9039    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   20.7927  -11.4240    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1794  -11.0781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.2999  -12.9940    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8126  -13.7245    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.1589  -10.4444    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.2612  -12.4626    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.6429  -12.0833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.5484  -12.8191    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.7594  -10.5593    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.8094  -15.5193    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8739  -14.6186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8131  -12.0576    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8313  -11.9555    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9071  -12.9887    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.6121   -8.5500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.4915   -6.6341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4582   -5.7695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.2523   -8.9893    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1317   -7.0733    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6064  -18.3849    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1015  -16.0710    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   22.1015  -17.3988    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.8920  -17.1474    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.6064  -15.9099    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.1191  -10.1201    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3124   -9.9471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0716   -6.1153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.9258  -10.2931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8782   -6.2882    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9987   -8.2043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1066  -13.1669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1920   -8.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9463  -10.9268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2920   -9.3136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.6974   -3.4143    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.3577  -15.2869    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.3600  -13.9520    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   23.1428  -15.0333    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   23.1442  -14.2083    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   17.0589   -9.1623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.9384   -7.2462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0112   -5.1574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9510   -4.1994    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7577   -4.3722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6064  -17.5599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3209  -16.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.3209  -17.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5830  -16.7349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8920  -16.3224    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 31  1  0  0  0  0
  1 46  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  2  9  1  0  0  0  0
  2 16  2  0  0  0  0
  3  5  1  0  0  0  0
  3  7  1  0  0  0  0
  3 10  1  0  0  0  0
  3 17  2  0  0  0  0
  4  8  1  0  0  0  0
  4 11  1  0  0  0  0
  4 12  1  0  0  0  0
  4 18  2  0  0  0  0
  6 32  1  0  0  0  0
  7 35  1  0  0  0  0
 43  8  1  1  0  0  0
 13 30  1  0  0  0  0
 42 14  1  1  0  0  0
 15 40  1  0  0  0  0
 15 41  1  0  0  0  0
 19 44  2  0  0  0  0
 20 45  2  0  0  0  0
 21 46  2  0  0  0  0
 22 34  1  0  0  0  0
 22 44  1  0  0  0  0
 23 33  1  0  0  0  0
 23 45  1  0  0  0  0
 24 49  1  0  0  0  0
 40 25  1  6  0  0  0
 25 50  1  0  0  0  0
 25 52  1  0  0  0  0
 26 51  1  0  0  0  0
 26 52  2  0  0  0  0
 27 49  1  0  0  0  0
 27 53  2  0  0  0  0
 28 50  2  0  0  0  0
 28 53  1  0  0  0  0
 29 30  1  0  0  0  0
 29 32  1  0  0  0  0
 29 37  1  0  0  0  0
 29 38  1  0  0  0  0
 30 44  1  0  0  0  0
 31 33  1  0  0  0  0
 34 36  1  0  0  0  0
 41 35  1  6  0  0  0
 36 45  1  0  0  0  0
 39 47  1  0  0  0  0
 40 42  1  0  0  0  0
 41 43  1  0  0  0  0
 42 43  1  0  0  0  0
 46 48  1  0  0  0  0
 47 48  2  0  0  0  0
 49 51  2  0  0  0  0
 50 51  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0029676

> <DATABASE_NAME>
MIME

> <SMILES>
C\C=C\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=C(N)N=CN=C12

> <INCHI_IDENTIFIER>
InChI=1S/C25H40N7O17P3S/c1-4-5-16(34)53-9-8-27-15(33)6-7-28-23(37)20(36)25(2,3)11-46-52(43,44)49-51(41,42)45-10-14-19(48-50(38,39)40)18(35)24(47-14)32-13-31-17-21(26)29-12-30-22(17)32/h4-5,12-14,18-20,24,35-36H,6-11H2,1-3H3,(H,27,33)(H,28,37)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/b5-4+/t14-,18-,19-,20?,24-/m1/s1

> <INCHI_KEY>
KFWWCMJSYSSPSK-BOGFJHSMSA-N

> <FORMULA>
C25H40N7O17P3S

> <MOLECULAR_WEIGHT>
835.608

> <EXACT_MASS>
835.141423115

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
73.18784114799007

> <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)-2-{[({[(3-{[2-({2-[(2E)-but-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
-0.11

> <JCHEM_LOGP>
-5.598949534966354

> <ALOGPS_LOGS>
-2.36

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
2.6787711798581504

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8252479627216065

> <JCHEM_PKA_STRONGEST_BASIC>
4.946047024039826

> <JCHEM_POLAR_SURFACE_AREA>
363.6299999999999

> <JCHEM_REFRACTIVITY>
182.5292

> <JCHEM_ROTATABLE_BOND_COUNT>
21

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.67e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-({[(3-{[2-({2-[(2E)-but-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

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  S   UNK     0      23.927  -9.950   0.000  0.00  0.00           S+0
HETATM    2  P   UNK     0      37.307 -21.002   0.000  0.00  0.00           P+0
HETATM    3  P   UNK     0      39.286 -22.790   0.000  0.00  0.00           P+0
HETATM    4  P   UNK     0      44.292 -24.087   0.000  0.00  0.00           P+0
HETATM    5  O   UNK     0      38.813 -21.325   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      35.802 -20.679   0.000  0.00  0.00           O+0
HETATM    7  O   UNK     0      39.760 -24.255   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      44.450 -25.619   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      37.630 -19.496   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      37.821 -23.264   0.000  0.00  0.00           O+0
HETATM   11  O   UNK     0      44.133 -22.555   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0      45.824 -23.929   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0      31.284 -19.711   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0      44.444 -28.969   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      40.831 -27.288   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0      36.984 -22.508   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      40.752 -22.317   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      42.760 -24.246   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      32.876 -15.960   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      28.917 -12.384   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      21.389 -10.770   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0      30.338 -16.780   0.000  0.00  0.00           N+0
HETATM   23  N   UNK     0      26.379 -13.203   0.000  0.00  0.00           N+0
HETATM   24  N   UNK     0      38.465 -34.318   0.000  0.00  0.00           N+0
HETATM   25  N   UNK     0      41.256 -29.999   0.000  0.00  0.00           N+0
HETATM   26  N   UNK     0      41.256 -32.478   0.000  0.00  0.00           N+0
HETATM   27  N   UNK     0      37.132 -32.008   0.000  0.00  0.00           N+0
HETATM   28  N   UNK     0      38.465 -29.698   0.000  0.00  0.00           N+0
HETATM   29  C   UNK     0      33.822 -18.891   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      32.316 -18.568   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      24.400 -11.415   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      35.328 -19.214   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      25.906 -11.738   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      29.864 -15.315   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      41.266 -24.578   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      28.358 -14.992   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      33.500 -20.397   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      34.145 -17.385   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      19.968  -6.373   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      41.734 -28.536   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      41.739 -26.044   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      43.200 -28.062   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0      43.203 -26.522   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0      31.843 -17.103   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      27.885 -13.526   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      22.421  -9.627   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      20.442  -7.839   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      21.948  -8.161   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      38.465 -32.778   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      39.799 -30.468   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      39.799 -32.008   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      42.155 -31.238   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      37.132 -30.468   0.000  0.00  0.00           C+0
CONECT    1   31   46                                                       
CONECT    2    5    6    9   16                                             
CONECT    3    5    7   10   17                                             
CONECT    4    8   11   12   18                                             
CONECT    5    2    3                                                       
CONECT    6    2   32                                                       
CONECT    7    3   35                                                       
CONECT    8    4   43                                                       
CONECT    9    2                                                            
CONECT   10    3                                                            
CONECT   11    4                                                            
CONECT   12    4                                                            
CONECT   13   30                                                            
CONECT   14   42                                                            
CONECT   15   40   41                                                       
CONECT   16    2                                                            
CONECT   17    3                                                            
CONECT   18    4                                                            
CONECT   19   44                                                            
CONECT   20   45                                                            
CONECT   21   46                                                            
CONECT   22   34   44                                                       
CONECT   23   33   45                                                       
CONECT   24   49                                                            
CONECT   25   40   50   52                                                  
CONECT   26   51   52                                                       
CONECT   27   49   53                                                       
CONECT   28   50   53                                                       
CONECT   29   30   32   37   38                                             
CONECT   30   13   29   44                                                  
CONECT   31    1   33                                                       
CONECT   32    6   29                                                       
CONECT   33   23   31                                                       
CONECT   34   22   36                                                       
CONECT   35    7   41                                                       
CONECT   36   34   45                                                       
CONECT   37   29                                                            
CONECT   38   29                                                            
CONECT   39   47                                                            
CONECT   40   15   25   42                                                  
CONECT   41   15   35   43                                                  
CONECT   42   14   40   43                                                  
CONECT   43    8   41   42                                                  
CONECT   44   19   22   30                                                  
CONECT   45   20   23   36                                                  
CONECT   46    1   21   48                                                  
CONECT   47   39   48                                                       
CONECT   48   46   47                                                       
CONECT   49   24   27   51                                                  
CONECT   50   25   28   51                                                  
CONECT   51   26   49   50                                                  
CONECT   52   25   26                                                       
CONECT   53   27   28                                                       
MASTER        0    0    0    0    0    0    0    0   53    0  110    0
END

Synonyms

Value	Source
2-Butenoyl-CoA	HMDB
2-Butenoyl-coenzyme A	HMDB
But-2-enoyl-CoA	HMDB
But-2-enoyl-coenzyme A	HMDB
Crotonyl-coenzyme A	HMDB
S-But-2-enoylcoenzyme A	HMDB
trans-But-2-enoyl-CoA	HMDB
trans-But-2-enoyl-coenzyme A	HMDB
Crotonyl-CoA	HMDB

Molecular Formula

C₂₅H₄₀N₇O₁₇P₃S

Average Mass

835.608

Monoisotopic Mass

835.141423115

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-2-{[({[(3-{[2-({2-[(2E)-but-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy)(hydroxy)phosphoryl]oxy}(hydroxy)phosphoryl)oxy]methyl}-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

Traditional Name

[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-2-({[(3-{[2-({2-[(2E)-but-2-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}-3-hydroxy-2,2-dimethylpropoxy(hydroxy)phosphoryl)oxy(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxyphosphonic acid

CAS Registry Number

102680-35-3

SMILES

C\C=C\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=C(N)N=CN=C12

InChI Identifier

InChI=1S/C25H40N7O17P3S/c1-4-5-16(34)53-9-8-27-15(33)6-7-28-23(37)20(36)25(2,3)11-46-52(43,44)49-51(41,42)45-10-14-19(48-50(38,39)40)18(35)24(47-14)32-13-31-17-21(26)29-12-30-22(17)32/h4-5,12-14,18-20,24,35-36H,6-11H2,1-3H3,(H,27,33)(H,28,37)(H,41,42)(H,43,44)(H2,26,29,30)(H2,38,39,40)/b5-4+/t14-,18-,19-,20?,24-/m1/s1

InChI Key

KFWWCMJSYSSPSK-BOGFJHSMSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a 2-enoyl chain.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

2-enoyl 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
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Thiocarboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organosulfur compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	3.67 g/L	ALOGPS
logP	-0.11	ALOGPS
logP	-5.6	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	21	ChemAxon
Refractivity	182.53 m³·mol⁻¹	ChemAxon
Polarizability	73.19 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-1901000120-017aeb03ebd91e701248	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1912000000-1727557fedacd67ecc0c	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2911000000-476bc5abc1a151d6d872	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00lr-7930140550-fee62adcd8bdf1cc9ba2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00o0-6910100010-21179bc614a07310997e	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-973d74ae97aba1d99ab1	2015-09-15	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane
Mitochondria
Peroxisome

Biospecimen Locations

Feces
Liver

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

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000064	Crotonoyl-CoA	3-Hydroxybutyryl-CoA	Enoyl coa hydratase domain containing 2	3-Hydroxybutyryl Coenzyme A Dehydratase, Mitochondrial	VMH	9073515
MMDBr0000194	Butyryl-CoA	Crotonoyl-CoA	Acyl-coa dehydrogenase family, member 10	Acyl Coenzyme A Dehydrogenase (Butanoyl Coenzyme A), Mitochondrial	VMH	2565344
MMDBr0000850	3-Hydroxybutyryl-CoA	Crotonoyl-CoA	Au rna binding protein/enoyl-coa hydratase	3-Hydroxyacyl Coenzyme A Dehydratase (3-Hydroxybutanoyl Coenzyme A), Mitochondrial	VMH	7558027
MMDBr0000851	3-Hydroxybutyryl-CoA	Crotonoyl-CoA	Enoyl coa hydratase 1, peroxisomal	3-Hydroxyacyl Coenzyme A Dehydratase (3-Hydroxybutanoyl Coenzyme A) (Perioxisome)	VMH	7558027
MMDBr0001344	FAD	Crotonoyl-CoA	Glutaryl-coa dehydrogenase	Glutaryl Coenzyme A Dehydrogenase, Mitochondrial	VMH	30371894
MMDBr0002588	Glutaryl-CoA	Crotonoyl-CoA	Glutaryl-coa dehydrogenase	Glutaryl Coenzyme A: (Acceptor) 2, 3-Oxidoreductase (Decarboxylating)	VMH	3081514
MMDBr0002959	Butyryl-CoA	Crotonoyl-CoA	Acyl-coa oxidase 1, palmitoyl	Acyl-CoA Oxidase	VMH	17603022 1774065 3597357 6240978 7876265
MMDBr0006895	Crotonoyl-CoA	Butyryl-CoA	Not Available	Acyl-CoA dehydrogenase (butanoyl-CoA)	VMH	30371894
MMDBr0006927	3-Hydroxybutyryl-CoA	Crotonoyl-CoA	Not Available	3-hydroxyacyl-CoA ((R)-3-hydroxybutanoyl-CoA)	VMH	30371894
MMDBr0007004	L-3-Aminobutyryl-CoA	Crotonoyl-CoA	Not Available	3-aminobutyryl-CoA ammonia-lyase	VMH	30371894
MMDBr0007011	Glutaconoyl-CoA	Crotonoyl-CoA	Not Available	Glutaconyl-CoA decarboxylase	VMH	30371894
MMDBr0007032	FAD	Crotonoyl-CoA	Not Available	Glutaryl-CoA dehydrogenase	VMH	30371894
MMDBr0007033	3-Hydroxybutyryl-CoA	Crotonoyl-CoA	Not Available	3-hydroxyacyl-CoA dehydratase (3-hydroxybutanoyl-CoA)	VMH	30371894
MMDBr0008530	Crotonoyl-CoA	Butyryl-CoA	Not Available	Acyl-CoA dehydrogenase (butanoyl-CoA)	VMH	30371894
MMDBr0008534	Butyryl-CoA	Crotonoyl-CoA	Not Available	Acyl-CoA dehydrogenase (butanoyl-CoA)	VMH	30371894
MMDBr0010038	Butyryl-CoA	Crotonoyl-CoA	Acyl-coa oxidase 1, palmitoyl	Acyl Coenzyme A Oxidase	VMH	30371894
MMDBr0010983	Butyryl-CoA	Crotonoyl-CoA	Not Available	Acyl-CoA dehydrogenase (butanoyl-CoA)	VMH	30371894
MMDBr0012847	(3S)-3-aminobutanoyl-CoA	Crotonoyl-CoA	3-aminobutyryl-CoA ammonia lyase	Non-hydrolytic bond cleavage (or its reversal); Non-hydrolytic bond cleavage (or its reversal)	RHEA	34755880
MMDBr0012923	vinylacetyl-CoA	Crotonoyl-CoA	4-hydroxybutyryl-CoA dehydratase/vinylacetyl-CoA-Delta-isomerase	Isomerization	RHEA	34755880
MMDBr0013694	(3R)-3-hydroxybutanoyl-CoA	Crotonoyl-CoA	3-hydroxybutyryl-CoA dehydratase	Hydration/dehydration of C-O bond	RHEA	34755880
MMDBr0013695	(3R)-3-hydroxybutanoyl-CoA	Crotonoyl-CoA	3-hydroxybutyryl-CoA dehydratase	Hydration/dehydration of C-O bond	RHEA	34755880
MMDBr0014403	(2E)-Glutaconyl-CoA	Crotonoyl-CoA	Glutaconyl-CoA decarboxylase subunit beta	Decarboxylation	RHEA	34755880
MMDBr0014406	butanoyl-CoA	Crotonoyl-CoA	Acyl-CoA dehydrogenase, short-chain specific	Dehydrogenation	RHEA	34755880
MMDBr0014653	4-Hydroxybutyryl-CoA	Crotonoyl-CoA	4-hydroxybutyryl-CoA dehydratase/vinylacetyl-CoA-Delta-isomerase	Isomerization	RHEA	34755880
MMDBr0014750	butanoyl-CoA	Crotonoyl-CoA	Crotonyl-CoA carboxylase/reductase	Carboxylation; Reduction	RHEA	34755880
MMDBr0014779	Ethylmalonyl Coenzyme A	Crotonoyl-CoA	Crotonyl-CoA carboxylase/reductase	Carboxylation	RHEA	34755880
MMDBr0014780	Crotonoyl-CoA	Ethylmalonyl Coenzyme A	Crotonyl-CoA carboxylase/reductase	Carboxylation	RHEA	34755880
MMDBr0016140	3-hydroxybutanoyl-CoA	Crotonoyl-CoA	Carnitinyl-CoA dehydratase	Hydration/dehydration of C-O bond	RHEA	34755880
MMDBr0016285	(2R)-hydroxybutanoyl-CoA	Crotonoyl-CoA	Lactoyl-CoA dehydratase subunit alpha	Hydration/dehydration of C-O bond	RHEA	34755880
MMDBr0016607	butanoyl-CoA	Crotonoyl-CoA	Enoyl-[acyl-carrier-protein] reductase [NADH] 1	Reduction	RHEA	34755880
MMDBr0016608	Crotonoyl-CoA	butanoyl-CoA	Enoyl-[acyl-carrier-protein] reductase [NADH] 1	Reduction	RHEA	34755880
MMDBr0018704	Crotonoyl-CoA	Water	2,3-dehydroadipyl-CoA hydratase	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0019726	Butyryl-CoA	Crotonoyl-CoA	Not Available		PathBank	31602464
MMDBr0019727	3-Hydroxybutyryl-CoA	Water	3-hydroxyisobutyryl-CoA hydrolase, mitochondrial	Hydrolysis of bond	PathBank	31602464
MMDBr0019729	Glutaryl-CoA	Carbon dioxide	Not Available		PathBank	31602464
MMDBr0025470	Crotonoyl-CoA	Hydrogen Ion	Histone acetyltransferase esa1	N-Acetylation	RHEA	34755880
MMDBr0025471	Crotonoyl-CoA	Hydrogen Ion	Histone acetyltransferase esa1	N-Acetylation	RHEA	34755880
MMDBr0038725	Crotonoyl-CoA	But-2-enoic 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	Proteobacteria	156	Human feces; Human sputum; Human ; Human unknown; Pig ; Human pleural fluid plaque; Human stool; Human feces; pleural fluid plaque; bal	Unknown; Metabolic reconstruction
Bacteria	Firmicutes	232	Pig ; Human feces; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Cattle ; Goat feces	Metabolic reconstruction
Bacteria	Actinobacteria	68	Human feces; Human ; Human subgingival plaque; Human supragingival plaque	Metabolic reconstruction
Bacteria	Bacteroidetes	22	Human feces; Human ; Human supragingival plaque; Human subgingival plaque; Human saliva	Metabolic reconstruction
Bacteria	Spirochaetes	1	Human feces	Metabolic reconstruction
Archaea	Thaumarchaeota	1		Metabolic reconstruction
Bacteria	Fusobacteria	19	Human feces; Human	Metabolic reconstruction
Bacteria	Synergistetes	2	Human feces	Metabolic reconstruction
Archaea	Euryarchaeota	1		Metabolic reconstruction
Bacteria	Planctomycetes	1	Human feces	Metabolic reconstruction
Archaea	Crenarchaeota	1		Metabolic reconstruction
Bacteria/NULL	Firmicutes	1	Pig ; Human feces; Human sputum; Human ; Human subgingival plaque; Human saliva; Human urine; Human mucosa; Cattle ; Goat feces	Metabolic reconstruction
Eukaryota/Fungi	Ascomycota	1	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	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
Human Liver	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

HMDB0002009

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022792

KNApSAcK ID

Not Available

Chemspider ID

4444072

KEGG Compound ID

C00877

BioCyc ID

Not Available

BiGG ID

36265

Wikipedia Link

Not Available

METLIN ID

440

PubChem Compound

5280381

PDB ID

Not Available

ChEBI ID

15473

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Gregersen N, Brandt NJ, Christensen E, Gron I, Rasmussen K, Brandt S: Glutaric aciduria: clinical and laboratory findings in two brothers. J Pediatr. 1977 May;90(5):740-5. doi: 10.1016/s0022-3476(77)81239-0. [PubMed:853337 ]
Lenich AC, Goodman SI: The purification and characterization of glutaryl-coenzyme A dehydrogenase from porcine and human liver. J Biol Chem. 1986 Mar 25;261(9):4090-6. [PubMed:3081514 ]
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Showing metabocard for Crotonoyl-CoA (MMDBc0029676)

MOL for #<Metabolite:0x00007fe2963709d0>

3D MOL for #<Metabolite:0x00007fe2963709d0>

3D SDF for #<Metabolite:0x00007fe2963709d0>

3D-SDF for #<Metabolite:0x00007fe2963709d0>

PDB for #<Metabolite:0x00007fe2963709d0>

3D PDB for #<Metabolite:0x00007fe2963709d0>

SMILES for #<Metabolite:0x00007fe2963709d0>

INCHI for #<Metabolite:0x00007fe2963709d0>

Structure for #<Metabolite:0x00007fe2963709d0>

3D Structure for #<Metabolite:0x00007fe2963709d0>