MiMeDB: Showing metabocard for (E)-feruloyl-CoA (MMDBc0055017)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:39:56 UTC

Update Date

2022-08-12 20:09:11 UTC

Metabolite ID

MMDBc0055017

Metabolite Identification

Common Name

(E)-feruloyl-CoA

Description

Feruloyl-CoA, also known as (e)-feruloyl-CoA, 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. Based on a literature review a significant number of articles have been published on Feruloyl-CoA.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221392D          

 68 71  0  0  1  0            999 V2000
   -1.4052   -6.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0461   -6.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4959  -11.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0872   -8.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6661   -7.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7547   -8.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9124   -8.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9816   -7.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2280   -7.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0702   -7.9842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8239   -7.6486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2473   -9.2527    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5683   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3119   -5.4102    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6538    1.5229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.3335   -8.4323    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.9147   -9.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -1.0091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6491   -7.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2450   -7.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -0.5966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8838   -1.2640    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.1394   -7.0512    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.6378    2.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.1104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8069   -7.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2257   -6.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    3.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4028   -7.4992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5605   -7.2005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3523    1.9354    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6378    0.6979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    2.1904    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.8555    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -13.3359   -9.8870    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -5.5628   -8.6553    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -9.3312   -6.9775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1937   -0.5966    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3857   -7.3867    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7206   -8.3566    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.0264   -2.1097    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    1.1998   -3.2137    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0347   -3.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -3.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344   -2.1319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9102   -4.0186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5512   -4.1910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8285  -10.5581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4820   -2.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.7307   -4.1048    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4913   -8.1335    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7523   -7.1269    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8262   -9.1034    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2282   -1.8239    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7432   -1.3316    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6288   -0.4794    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8931   -6.7156    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986    0.1999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 17  4  1  0  0  0  0
 17  5  1  0  0  0  0
 17 12  2  0  0  0  0
 18  6  1  0  0  0  0
 19 12  1  0  0  0  0
 19 18  2  0  0  0  0
 20 13  1  1  0  0  0
 21  8  1  0  0  0  0
 22  7  1  0  0  0  0
 25 20  1  0  0  0  0
 25 24  1  0  0  0  0
 27 23  2  0  0  0  0
 28 23  1  0  0  0  0
 29 26  1  0  0  0  0
 30 24  1  0  0  0  0
 31  1  1  0  0  0  0
 31  2  1  0  0  0  0
 31 14  1  0  0  0  0
 31 26  1  0  0  0  0
 32 27  1  0  0  0  0
 33 10  1  4  0  0  0
 33 21  2  0  0  0  0
 34  9  1  4  0  0  0
 34 29  2  0  0  0  0
 35 15  2  0  0  0  0
 35 27  1  0  0  0  0
 36 15  1  0  0  0  0
 36 28  2  0  0  0  0
 37 16  2  0  0  0  0
 37 23  1  0  0  0  0
 38 16  1  0  0  0  0
 38 28  1  0  0  0  0
 30 38  1  1  0  0  0
 39 18  1  0  0  0  0
 40 21  1  0  0  0  0
 41 22  2  0  0  0  0
 24 42  1  6  0  0  0
 26 43  1  6  0  0  0
 44 29  1  0  0  0  0
 52  3  1  0  0  0  0
 52 19  1  0  0  0  0
 53 13  1  0  0  0  0
 54 14  1  0  0  0  0
 55 20  1  0  0  0  0
 55 30  1  0  0  0  0
 25 56  1  1  0  0  0
 58 45  1  0  0  0  0
 58 46  1  0  0  0  0
 58 47  2  0  0  0  0
 58 56  1  0  0  0  0
 59 48  1  0  0  0  0
 59 49  2  0  0  0  0
 59 53  1  0  0  0  0
 59 57  1  0  0  0  0
 60 50  1  0  0  0  0
 60 51  2  0  0  0  0
 60 54  1  0  0  0  0
 60 57  1  0  0  0  0
 61 11  1  0  0  0  0
 61 22  1  0  0  0  0
 62  5  1  0  0  0  0
 63  7  1  0  0  0  0
 20 64  1  6  0  0  0
 24 65  1  1  0  0  0
 25 66  1  1  0  0  0
 26 67  1  6  0  0  0
 30 68  1  6  0  0  0
M  CHG  4  39  -1  40  -1  44  -1  45  -1
M  END


  Mrv1652306172221392D          

 68 71  0  0  1  0            999 V2000
   -1.4052   -6.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0461   -6.3169    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.4959  -11.0431    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0872   -8.0967    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.6661   -7.9473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.7547   -8.5816    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9124   -8.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9816   -7.3499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2280   -7.6854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.5683   -1.4940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  -11.9147   -9.7377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -1.0091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -5.6491   -7.8348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2450   -7.7980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9233    1.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3687   -0.5966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -2.1394   -7.0512    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -2.8069   -7.5361    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8838    0.0709    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.2257   -6.2307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -6.4028   -7.4992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5605   -7.2005    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -9.3312   -6.9775    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.7206   -8.3566    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.0264   -2.1097    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
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    0.0347   -3.2748    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6646   -3.4668    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6344   -2.1319    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9102   -4.0186    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5512   -4.1910    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.8285  -10.5581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4820   -2.3145    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6444   -4.9253    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0992   -0.1841    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387   -2.0486    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8169   -3.2843    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5867   -2.6617    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1495   -2.7994    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7307   -4.1048    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4913   -8.1335    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -10.7523   -7.1269    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8931   -6.7156    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6986    0.1999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  4  2  0  0  0  0
  7  5  2  0  0  0  0
  9  8  1  0  0  0  0
 11 10  1  0  0  0  0
 17  4  1  0  0  0  0
 17  5  1  0  0  0  0
 17 12  2  0  0  0  0
 18  6  1  0  0  0  0
 19 12  1  0  0  0  0
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 20 13  1  1  0  0  0
 21  8  1  0  0  0  0
 22  7  1  0  0  0  0
 25 20  1  0  0  0  0
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 28 23  1  0  0  0  0
 29 26  1  0  0  0  0
 30 24  1  0  0  0  0
 31  1  1  0  0  0  0
 31  2  1  0  0  0  0
 31 14  1  0  0  0  0
 31 26  1  0  0  0  0
 32 27  1  0  0  0  0
 33 10  1  4  0  0  0
 33 21  2  0  0  0  0
 34  9  1  4  0  0  0
 34 29  2  0  0  0  0
 35 15  2  0  0  0  0
 35 27  1  0  0  0  0
 36 15  1  0  0  0  0
 36 28  2  0  0  0  0
 37 16  2  0  0  0  0
 37 23  1  0  0  0  0
 38 16  1  0  0  0  0
 38 28  1  0  0  0  0
 30 38  1  1  0  0  0
 39 18  1  0  0  0  0
 40 21  1  0  0  0  0
 41 22  2  0  0  0  0
 24 42  1  6  0  0  0
 26 43  1  6  0  0  0
 44 29  1  0  0  0  0
 52  3  1  0  0  0  0
 52 19  1  0  0  0  0
 53 13  1  0  0  0  0
 54 14  1  0  0  0  0
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 55 30  1  0  0  0  0
 25 56  1  1  0  0  0
 58 45  1  0  0  0  0
 58 46  1  0  0  0  0
 58 47  2  0  0  0  0
 58 56  1  0  0  0  0
 59 48  1  0  0  0  0
 59 49  2  0  0  0  0
 59 53  1  0  0  0  0
 59 57  1  0  0  0  0
 60 50  1  0  0  0  0
 60 51  2  0  0  0  0
 60 54  1  0  0  0  0
 60 57  1  0  0  0  0
 61 11  1  0  0  0  0
 61 22  1  0  0  0  0
 62  5  1  0  0  0  0
 63  7  1  0  0  0  0
 20 64  1  6  0  0  0
 24 65  1  1  0  0  0
 25 66  1  1  0  0  0
 26 67  1  6  0  0  0
 30 68  1  6  0  0  0
M  CHG  4  39  -1  40  -1  44  -1  45  -1
M  END
> <DATABASE_ID>
MMDBc0055017

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\[H])C1=CC(OC)=C([O-])C=C1)C(=O)SCCN=C([O-])CCN=C([O-])[C@]([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)([O-])=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H44N7O19P3S/c1-31(2,26(43)29(44)34-9-8-21(40)33-10-11-61-22(41)7-5-17-4-6-18(39)19(12-17)52-3)14-54-60(50,51)57-59(48,49)53-13-20-25(56-58(45,46)47)24(42)30(55-20)38-16-37-23-27(32)35-15-36-28(23)38/h4-7,12,15-16,20,24-26,30,39,42-43H,8-11,13-14H2,1-3H3,(H,33,40)(H,34,44)(H,48,49)(H,50,51)(H2,32,35,36)(H2,45,46,47)/p-4/b7-5+/t20-,24-,25-,26+,30-/m1/s1

> <INCHI_KEY>
GBXZVJQQDAJGSO-NBXNMEGSSA-J

> <FORMULA>
C31H40N7O19P3S

> <MOLECULAR_WEIGHT>
939.67

> <EXACT_MASS>
939.133448584

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
101

> <JCHEM_AVERAGE_POLARIZABILITY>
85.3930327853731

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-(hydrogen phosphonooxy)-4-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-{2-[(2-{[(2E)-3-(3-methoxy-4-oxidophenyl)prop-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanecarboximidate

> <JCHEM_LOGP>
-2.1154256617199745

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.891635921610324

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8196430158487353

> <JCHEM_PKA_STRONGEST_BASIC>
4.158898242385794

> <JCHEM_POLAR_SURFACE_AREA>
411.3900000000001

> <JCHEM_REFRACTIVITY>
242.64090000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
23

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3-(hydrogen phosphonooxy)-4-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-N-{2-[(2-{[(2E)-3-(3-methoxy-4-oxidophenyl)prop-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanecarboximidate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-JUN-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JUN-22         0                                  
HETATM    1  C   UNK     0      -2.623 -11.470   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.686 -11.792   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -23.326 -20.614   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -22.563 -15.114   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -19.910 -14.835   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -23.809 -16.019   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -18.503 -15.461   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.299 -13.720   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.892 -14.346   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -13.198 -14.904   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -14.605 -14.277   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0     -20.995 -17.272   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.061  -2.789   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -4.316 -10.099   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -21.156 -15.740   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -23.648 -17.551   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -22.241 -18.177   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       0.185  -1.884   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -10.545 -14.625   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -17.257 -14.556   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.555  -1.114   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.650  -2.359   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.994 -13.162   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -5.239 -14.067   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -4.155 -11.631   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0       4.924   5.923   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0     -11.952 -13.999   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0      -6.646 -13.441   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0       6.258   3.613   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0       4.924   1.303   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   38  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   39  O   UNK     0     -24.894 -18.456   0.000  0.00  0.00           O-1
HETATM   40  O   UNK     0     -10.384 -16.157   0.000  0.00  0.00           O-1
HETATM   41  O   UNK     0     -17.418 -13.025   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       4.095  -1.114   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -2.587 -13.789   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -5.078 -15.599   0.000  0.00  0.00           O-1
HETATM   45  O   UNK     0      -0.049  -3.938   0.000  0.00  0.00           O-1
HETATM   46  O   UNK     0       2.240  -5.999   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0       0.065  -6.113   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      -1.241  -6.471   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      -3.051  -3.980   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -1.699  -7.501   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -4.762  -7.823   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0     -22.080 -19.709   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      -0.900  -4.320   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      -3.070  -9.194   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       0.185  -0.344   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0       2.126  -3.824   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      -3.392  -6.131   0.000  0.00  0.00           O+0
HETATM   58  P   UNK     0       1.095  -4.969   0.000  0.00  0.00           P+0
HETATM   59  P   UNK     0      -2.146  -5.226   0.000  0.00  0.00           P+0
HETATM   60  P   UNK     0      -3.231  -7.662   0.000  0.00  0.00           P+0
HETATM   61  S   UNK     0     -15.850 -15.183   0.000  0.00  0.00           S+0
HETATM   62  H   UNK     0     -20.071 -13.303   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0     -18.342 -16.993   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.426  -3.405   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0       3.254  -2.486   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0       1.174  -0.895   0.000  0.00  0.00           H+0
HETATM   67  H   UNK     0      -5.400 -12.536   0.000  0.00  0.00           H+0
HETATM   68  H   UNK     0       3.171   0.373   0.000  0.00  0.00           H+0
CONECT    1   31                                                            
CONECT    2   31                                                            
CONECT    3   52                                                            
CONECT    4    6   17                                                       
CONECT    5    7   17   62                                                  
CONECT    6    4   18                                                       
CONECT    7    5   22   63                                                  
CONECT    8    9   21                                                       
CONECT    9    8   34                                                       
CONECT   10   11   33                                                       
CONECT   11   10   61                                                       
CONECT   12   17   19                                                       
CONECT   13   20   53                                                       
CONECT   14   31   54                                                       
CONECT   15   35   36                                                       
CONECT   16   37   38                                                       
CONECT   17    4    5   12                                                  
CONECT   18    6   19   39                                                  
CONECT   19   12   18   52                                                  
CONECT   20   13   25   55   64                                             
CONECT   21    8   33   40                                                  
CONECT   22    7   41   61                                                  
CONECT   23   27   28   37                                                  
CONECT   24   25   30   42   65                                             
CONECT   25   20   24   56   66                                             
CONECT   26   29   31   43   67                                             
CONECT   27   23   32   35                                                  
CONECT   28   23   36   38                                                  
CONECT   29   26   34   44                                                  
CONECT   30   24   38   55   68                                             
CONECT   31    1    2   14   26                                             
CONECT   32   27                                                            
CONECT   33   10   21                                                       
CONECT   34    9   29                                                       
CONECT   35   15   27                                                       
CONECT   36   15   28                                                       
CONECT   37   16   23                                                       
CONECT   38   16   28   30                                                  
CONECT   39   18                                                            
CONECT   40   21                                                            
CONECT   41   22                                                            
CONECT   42   24                                                            
CONECT   43   26                                                            
CONECT   44   29                                                            
CONECT   45   58                                                            
CONECT   46   58                                                            
CONECT   47   58                                                            
CONECT   48   59                                                            
CONECT   49   59                                                            
CONECT   50   60                                                            
CONECT   51   60                                                            
CONECT   52    3   19                                                       
CONECT   53   13   59                                                       
CONECT   54   14   60                                                       
CONECT   55   20   30                                                       
CONECT   56   25   58                                                       
CONECT   57   59   60                                                       
CONECT   58   45   46   47   56                                             
CONECT   59   48   49   53   57                                             
CONECT   60   50   51   54   57                                             
CONECT   61   11   22                                                       
CONECT   62    5                                                            
CONECT   63    7                                                            
CONECT   64   20                                                            
CONECT   65   24                                                            
CONECT   66   25                                                            
CONECT   67   26                                                            
CONECT   68   30                                                            
MASTER        0    0    0    0    0    0    0    0   68    0  142    0
END

Synonyms

Value	Source
(e)-Feruloyl-CoA	ChEBI
(e)-Feruloyl-CoA(4-)	ChEBI
(e)-Feruloyl-coenzyme A(4-)	ChEBI
trans-4-Hydroxy-3-methoxycinnamoyl-CoA(4-)	ChEBI
trans-4-Hydroxy-3-methoxycinnamoyl-coenzyme A(4-)	ChEBI
trans-Feruloyl-coenzyme A(4-)	ChEBI
Feruloyl-coenzyme A	MeSH

Molecular Formula

C₃₁H₄₀N₇O₁₉P₃S

Average Mass

939.67

Monoisotopic Mass

939.133448584

IUPAC Name

(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-3-(hydrogen phosphonooxy)-4-hydroxyoxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-N-{2-[(2-{[(2E)-3-(3-methoxy-4-oxidophenyl)prop-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanecarboximidate

Traditional Name

(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3-(hydrogen phosphonooxy)-4-hydroxyoxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-2-hydroxy-N-{2-[(2-{[(2E)-3-(3-methoxy-4-oxidophenyl)prop-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-3,3-dimethylbutanecarboximidate

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC(OC)=C([O-])C=C1)C(=O)SCCN=C([O-])CCN=C([O-])[C@]([H])(O)C(C)(C)COP(O)(=O)OP(O)(=O)OC[C@@]1([H])O[C@@]([H])(N2C=NC3=C(N)N=CN=C23)[C@]([H])(O)[C@]1([H])OP(O)([O-])=O

InChI Identifier

InChI=1S/C31H44N7O19P3S/c1-31(2,26(43)29(44)34-9-8-21(40)33-10-11-61-22(41)7-5-17-4-6-18(39)19(12-17)52-3)14-54-60(50,51)57-59(48,49)53-13-20-25(56-58(45,46)47)24(42)30(55-20)38-16-37-23-27(32)35-15-36-28(23)38/h4-7,12,15-16,20,24-26,30,39,42-43H,8-11,13-14H2,1-3H3,(H,33,40)(H,34,44)(H,48,49)(H,50,51)(H2,32,35,36)(H2,45,46,47)/p-4/b7-5+/t20-,24-,25-,26+,30-/m1/s1

InChI Key

GBXZVJQQDAJGSO-NBXNMEGSSA-J

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 diphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside 3',5'-bisphosphate
Pentose-5-phosphate
Pentose phosphate
Ribonucleoside 3'-phosphate
Hydroxycinnamic acid or derivatives
Cinnamic acid or derivatives
N-glycosyl compound
Glycosyl compound
Beta amino acid or derivatives
Methoxyphenol
Monosaccharide phosphate
Organic pyrophosphate
6-aminopurine
Purine
Imidazopyrimidine
Anisole
Phenol ether
Styrene
Methoxybenzene
Phenoxy compound
Aminopyrimidine
Alkyl aryl ether
Phenol
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Fatty amide
Imidolactam
Benzenoid
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Alkyl phosphate
Phosphoric acid ester
Pyrimidine
Tetrahydrofuran
Azole
Heteroaromatic compound
Imidazole
Secondary alcohol
Secondary carboxylic acid amide
Thiocarboxylic acid ester
Carboxamide group
Carbothioic s-ester
Amino acid or derivatives
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Sulfenyl compound
Ether
Oxacycle
Carboxylic acid derivative
Organopnictogen compound
Organonitrogen compound
Primary amine
Carbonyl group
Organooxygen compound
Organosulfur compound
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Amine
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

feruloyl-CoA(4-) (CHEBI:87305 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-2.1	ChemAxon
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.16	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	411.39 Å²	ChemAxon
Rotatable Bond Count	23	ChemAxon
Refractivity	242.64 m³·mol⁻¹	ChemAxon
Polarizability	85.39 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

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

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	nah	1
Bacteria	Proteobacteria	1	Human ; Human subgingival plaque

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

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00007264

Chemspider ID

58145554

KEGG Compound ID

Not Available

BioCyc ID

FERULOYL-COA

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

44229137

PDB ID

Not Available

ChEBI ID

87305

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bansal P, Morgat A, Axelsen KB, Muthukrishnan V, Coudert E, Aimo L, Hyka-Nouspikel N, Gasteiger E, Kerhornou A, Neto TB, Pozzato M, Blatter MC, Ignatchenko A, Redaschi N, Bridge A: Rhea, the reaction knowledgebase in 2022. Nucleic Acids Res. 2022 Jan 7;50(D1):D693-D700. doi: 10.1093/nar/gkab1016. [PubMed:34755880 ]

Showing metabocard for (E)-feruloyl-CoA (MMDBc0055017)

MOL for #<Metabolite:0x00007fed147880d0>

3D MOL for #<Metabolite:0x00007fed147880d0>

3D SDF for #<Metabolite:0x00007fed147880d0>

3D-SDF for #<Metabolite:0x00007fed147880d0>

PDB for #<Metabolite:0x00007fed147880d0>

3D PDB for #<Metabolite:0x00007fed147880d0>

SMILES for #<Metabolite:0x00007fed147880d0>

INCHI for #<Metabolite:0x00007fed147880d0>

Structure for #<Metabolite:0x00007fed147880d0>

3D Structure for #<Metabolite:0x00007fed147880d0>