MiMeDB: Showing metabocard for (E)-caffeoyl-CoA (MMDBc0055016)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:39:54 UTC

Update Date

2022-08-12 20:09:11 UTC

Metabolite ID

MMDBc0055016

Metabolite Identification

Common Name

(E)-caffeoyl-CoA

Description

(E)-caffeoyl-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 very few articles have been published on (E)-caffeoyl-CoA.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221392D          

 67 70  0  0  1  0            999 V2000
   -5.2497   -0.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9209   -2.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.2868   -2.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.8657   -2.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.9542   -2.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1120   -2.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1812   -1.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4275   -1.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2698   -2.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -12.0234   -1.8684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -15.4469   -3.4726    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
   -4.8316   -1.9421    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
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  -16.8680   -3.6219    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.1143   -3.9575    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
   -9.8486   -2.0546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -13.4445   -2.0178    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
   -6.3390   -1.2710    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
   -7.0064   -1.7559    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
   -5.5853   -1.6065    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
  -10.6023   -1.7191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7601   -1.4203    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
  -17.5354   -4.1068    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -16.0281   -4.7780    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -9.7624   -2.8751    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -13.5308   -1.1973    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
   -6.4252   -0.4505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9202   -2.5764    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.0264   -2.1097    0.0000 O   0  0  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
   -2.4743   -0.9759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5045   -2.3108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0749   -1.0390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7461   -2.5464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -1.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -1.9894   -1.6433    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -1.7927    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6909   -2.3533    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -14.9519   -1.3467    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0257   -3.3232    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
   -6.2527   -2.0914    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
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 16  3  1  0  0  0  0
 16  4  1  0  0  0  0
 16 11  2  0  0  0  0
 17  5  1  0  0  0  0
 18 11  1  0  0  0  0
 18 17  2  0  0  0  0
 19 12  1  1  0  0  0
 20  7  1  0  0  0  0
 21  6  1  0  0  0  0
 24 19  1  0  0  0  0
 24 23  1  0  0  0  0
 26 22  2  0  0  0  0
 27 22  1  0  0  0  0
 28 25  1  0  0  0  0
 29 23  1  0  0  0  0
 30  1  1  0  0  0  0
 30  2  1  0  0  0  0
 30 13  1  0  0  0  0
 30 25  1  0  0  0  0
 31 26  1  0  0  0  0
 32  9  1  4  0  0  0
 32 20  2  0  0  0  0
 33  8  1  4  0  0  0
 33 28  2  0  0  0  0
 34 14  2  0  0  0  0
 34 26  1  0  0  0  0
 35 14  1  0  0  0  0
 35 27  2  0  0  0  0
 36 15  2  0  0  0  0
 36 22  1  0  0  0  0
 37 15  1  0  0  0  0
 37 27  1  0  0  0  0
 29 37  1  1  0  0  0
 38 17  1  0  0  0  0
 39 18  1  0  0  0  0
 40 20  1  0  0  0  0
 41 21  2  0  0  0  0
 23 42  1  6  0  0  0
 25 43  1  1  0  0  0
 44 28  1  0  0  0  0
 52 12  1  0  0  0  0
 53 13  1  0  0  0  0
 54 19  1  0  0  0  0
 54 29  1  0  0  0  0
 24 55  1  1  0  0  0
 57 45  1  0  0  0  0
 57 46  1  0  0  0  0
 57 47  2  0  0  0  0
 57 55  1  0  0  0  0
 58 48  1  0  0  0  0
 58 49  2  0  0  0  0
 58 52  1  0  0  0  0
 58 56  1  0  0  0  0
 59 50  1  0  0  0  0
 59 51  2  0  0  0  0
 59 53  1  0  0  0  0
 59 56  1  0  0  0  0
 60 10  1  0  0  0  0
 60 21  1  0  0  0  0
 61  4  1  0  0  0  0
 62  6  1  0  0  0  0
 19 63  1  6  0  0  0
 23 64  1  1  0  0  0
 24 65  1  1  0  0  0
 25 66  1  1  0  0  0
 29 67  1  6  0  0  0
M  CHG  4  38  -1  39  -1  40  -1  44  -1
M  END


  Mrv1652306172221392D          

 67 70  0  0  1  0            999 V2000
   -5.2497   -0.8528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9209   -2.3602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.2868   -2.3165    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.8657   -2.1672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -16.9542   -2.8014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -14.1120   -2.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1812   -1.5697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4275   -1.9052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -11.2698   -2.2040    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -4.8316   -1.9421    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0992   -1.0091    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    1.3687   -0.5966    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -6.3390   -1.2710    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   -5.5853   -1.6065    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
  -10.6023   -1.7191    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7601   -1.4203    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
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   -9.7624   -2.8751    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
  -13.5308   -1.1973    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
   -6.4252   -0.4505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9202   -2.5764    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -0.0264   -2.1097    0.0000 O   0  0  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
   -2.4743   -0.9759    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5045   -2.3108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0749   -1.0390    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7461   -2.5464    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3220   -1.1584    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1642   -1.4572    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
   -2.6568   -2.1283    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
   -1.9894   -1.6433    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4105   -1.7927    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
  -12.6909   -2.3533    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
  -14.9519   -1.3467    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  -14.0257   -3.3232    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
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    1.6986    0.1999    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  5  3  2  0  0  0  0
  6  4  2  0  0  0  0
  8  7  1  0  0  0  0
 10  9  1  0  0  0  0
 16  3  1  0  0  0  0
 16  4  1  0  0  0  0
 16 11  2  0  0  0  0
 17  5  1  0  0  0  0
 18 11  1  0  0  0  0
 18 17  2  0  0  0  0
 19 12  1  1  0  0  0
 20  7  1  0  0  0  0
 21  6  1  0  0  0  0
 24 19  1  0  0  0  0
 24 23  1  0  0  0  0
 26 22  2  0  0  0  0
 27 22  1  0  0  0  0
 28 25  1  0  0  0  0
 29 23  1  0  0  0  0
 30  1  1  0  0  0  0
 30  2  1  0  0  0  0
 30 13  1  0  0  0  0
 30 25  1  0  0  0  0
 31 26  1  0  0  0  0
 32  9  1  4  0  0  0
 32 20  2  0  0  0  0
 33  8  1  4  0  0  0
 33 28  2  0  0  0  0
 34 14  2  0  0  0  0
 34 26  1  0  0  0  0
 35 14  1  0  0  0  0
 35 27  2  0  0  0  0
 36 15  2  0  0  0  0
 36 22  1  0  0  0  0
 37 15  1  0  0  0  0
 37 27  1  0  0  0  0
 29 37  1  1  0  0  0
 38 17  1  0  0  0  0
 39 18  1  0  0  0  0
 40 20  1  0  0  0  0
 41 21  2  0  0  0  0
 23 42  1  6  0  0  0
 25 43  1  1  0  0  0
 44 28  1  0  0  0  0
 52 12  1  0  0  0  0
 53 13  1  0  0  0  0
 54 19  1  0  0  0  0
 54 29  1  0  0  0  0
 24 55  1  1  0  0  0
 57 45  1  0  0  0  0
 57 46  1  0  0  0  0
 57 47  2  0  0  0  0
 57 55  1  0  0  0  0
 58 48  1  0  0  0  0
 58 49  2  0  0  0  0
 58 52  1  0  0  0  0
 58 56  1  0  0  0  0
 59 50  1  0  0  0  0
 59 51  2  0  0  0  0
 59 53  1  0  0  0  0
 59 56  1  0  0  0  0
 60 10  1  0  0  0  0
 60 21  1  0  0  0  0
 61  4  1  0  0  0  0
 62  6  1  0  0  0  0
 19 63  1  6  0  0  0
 23 64  1  1  0  0  0
 24 65  1  1  0  0  0
 25 66  1  1  0  0  0
 29 67  1  6  0  0  0
M  CHG  4  38  -1  39  -1  40  -1  44  -1
M  END
> <DATABASE_ID>
MMDBc0055016

> <DATABASE_NAME>
MIME

> <SMILES>
[H]\C(=C(\[H])C1=CC([O-])=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/C30H42N7O19P3S/c1-30(2,25(43)28(44)33-8-7-20(40)32-9-10-60-21(41)6-4-16-3-5-17(38)18(39)11-16)13-53-59(50,51)56-58(48,49)52-12-19-24(55-57(45,46)47)23(42)29(54-19)37-15-36-22-26(31)34-14-35-27(22)37/h3-6,11,14-15,19,23-25,29,38-39,42-43H,7-10,12-13H2,1-2H3,(H,32,40)(H,33,44)(H,48,49)(H,50,51)(H2,31,34,35)(H2,45,46,47)/p-4/b6-4+/t19-,23-,24-,25+,29-/m1/s1

> <INCHI_KEY>
QHRGJMIMHCLHRG-ZSELIEHESA-J

> <FORMULA>
C30H38N7O19P3S

> <MOLECULAR_WEIGHT>
925.65

> <EXACT_MASS>
925.117798519

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
98

> <JCHEM_AVERAGE_POLARIZABILITY>
83.22086136546957

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(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)-N-{2-[(2-{[(2E)-3-(3,4-dioxidophenyl)prop-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-2-hydroxy-3,3-dimethylbutanecarboximidate

> <JCHEM_LOGP>
0.06881212266666759

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.895384175137535

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8199930265630204

> <JCHEM_PKA_STRONGEST_BASIC>
-6.282405676964939

> <JCHEM_POLAR_SURFACE_AREA>
422.3900000000001

> <JCHEM_REFRACTIVITY>
249.8306000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
22

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R)-4-[({[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy(hydroxy)phosphoryl}oxy(hydroxy)phosphoryl)oxy]-N-{2-[(2-{[(2E)-3-(3,4-dioxidophenyl)prop-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-2-hydroxy-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      -9.800  -1.592   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0     -11.052  -4.406   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0     -30.402  -4.324   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0     -27.749  -4.045   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0     -31.648  -5.229   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0     -26.342  -4.672   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0     -17.138  -2.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0     -15.731  -3.556   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0     -21.037  -4.114   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0     -22.444  -3.488   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -28.834  -6.482   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.061  -2.789   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -9.019  -3.625   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.258   2.073   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.220   2.843   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0     -28.995  -4.951   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0     -31.487  -6.761   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0     -30.080  -7.387   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       0.185  -1.884   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -18.384  -3.835   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -25.096  -3.767   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.590   3.613   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.555  -1.114   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.650  -2.359   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0     -11.833  -2.372   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       4.924   4.383   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       3.590   2.073   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0     -13.079  -3.278   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.650   0.132   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -10.426  -2.999   0.000  0.00  0.00           C+0
HETATM   31  N   UNK     0       4.924   5.923   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0     -19.791  -3.209   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0     -14.485  -2.651   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0       6.258   3.613   0.000  0.00  0.00           N+0
HETATM   35  N   UNK     0       4.924   1.303   0.000  0.00  0.00           N+0
HETATM   36  N   UNK     0       2.126   4.089   0.000  0.00  0.00           N+0
HETATM   37  N   UNK     0       2.126   1.597   0.000  0.00  0.00           N+0
HETATM   38  O   UNK     0     -32.733  -7.666   0.000  0.00  0.00           O-1
HETATM   39  O   UNK     0     -29.919  -8.919   0.000  0.00  0.00           O-1
HETATM   40  O   UNK     0     -18.223  -5.367   0.000  0.00  0.00           O-1
HETATM   41  O   UNK     0     -25.257  -2.235   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     -11.994  -0.841   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0     -12.918  -4.809   0.000  0.00  0.00           O-1
HETATM   45  O   UNK     0      -0.049  -3.938   0.000  0.00  0.00           O+0
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      -4.619  -1.822   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      -2.808  -4.313   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -5.740  -1.940   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      -6.993  -4.753   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -2.468  -2.162   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      -7.773  -2.720   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0       0.185  -0.344   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0       2.126  -3.824   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      -4.959  -3.973   0.000  0.00  0.00           O+0
HETATM   57  P   UNK     0       1.095  -4.969   0.000  0.00  0.00           P+0
HETATM   58  P   UNK     0      -3.714  -3.068   0.000  0.00  0.00           P+0
HETATM   59  P   UNK     0      -6.366  -3.346   0.000  0.00  0.00           P+0
HETATM   60  S   UNK     0     -23.690  -4.393   0.000  0.00  0.00           S+0
HETATM   61  H   UNK     0     -27.910  -2.514   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0     -26.181  -6.203   0.000  0.00  0.00           H+0
HETATM   63  H   UNK     0       0.426  -3.405   0.000  0.00  0.00           H+0
HETATM   64  H   UNK     0       3.254  -2.486   0.000  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.174  -0.895   0.000  0.00  0.00           H+0
HETATM   66  H   UNK     0     -11.672  -3.904   0.000  0.00  0.00           H+0
HETATM   67  H   UNK     0       3.171   0.373   0.000  0.00  0.00           H+0
CONECT    1   30                                                            
CONECT    2   30                                                            
CONECT    3    5   16                                                       
CONECT    4    6   16   61                                                  
CONECT    5    3   17                                                       
CONECT    6    4   21   62                                                  
CONECT    7    8   20                                                       
CONECT    8    7   33                                                       
CONECT    9   10   32                                                       
CONECT   10    9   60                                                       
CONECT   11   16   18                                                       
CONECT   12   19   52                                                       
CONECT   13   30   53                                                       
CONECT   14   34   35                                                       
CONECT   15   36   37                                                       
CONECT   16    3    4   11                                                  
CONECT   17    5   18   38                                                  
CONECT   18   11   17   39                                                  
CONECT   19   12   24   54   63                                             
CONECT   20    7   32   40                                                  
CONECT   21    6   41   60                                                  
CONECT   22   26   27   36                                                  
CONECT   23   24   29   42   64                                             
CONECT   24   19   23   55   65                                             
CONECT   25   28   30   43   66                                             
CONECT   26   22   31   34                                                  
CONECT   27   22   35   37                                                  
CONECT   28   25   33   44                                                  
CONECT   29   23   37   54   67                                             
CONECT   30    1    2   13   25                                             
CONECT   31   26                                                            
CONECT   32    9   20                                                       
CONECT   33    8   28                                                       
CONECT   34   14   26                                                       
CONECT   35   14   27                                                       
CONECT   36   15   22                                                       
CONECT   37   15   27   29                                                  
CONECT   38   17                                                            
CONECT   39   18                                                            
CONECT   40   20                                                            
CONECT   41   21                                                            
CONECT   42   23                                                            
CONECT   43   25                                                            
CONECT   44   28                                                            
CONECT   45   57                                                            
CONECT   46   57                                                            
CONECT   47   57                                                            
CONECT   48   58                                                            
CONECT   49   58                                                            
CONECT   50   59                                                            
CONECT   51   59                                                            
CONECT   52   12   58                                                       
CONECT   53   13   59                                                       
CONECT   54   19   29                                                       
CONECT   55   24   57                                                       
CONECT   56   58   59                                                       
CONECT   57   45   46   47   55                                             
CONECT   58   48   49   52   56                                             
CONECT   59   50   51   53   56                                             
CONECT   60   10   21                                                       
CONECT   61    4                                                            
CONECT   62    6                                                            
CONECT   63   19                                                            
CONECT   64   23                                                            
CONECT   65   24                                                            
CONECT   66   25                                                            
CONECT   67   29                                                            
MASTER        0    0    0    0    0    0    0    0   67    0  140    0
END

Synonyms

Value	Source
(e)-3,4-Dihydroxycinnamoyl-CoA(4-)	ChEBI
(e)-3,4-Dihydroxycinnamoyl-coenzyme A(4-)	ChEBI
(e)-Caffeoyl-CoA(4-)	ChEBI
(e)-Caffeoyl-coenzyme A(4-)	ChEBI
trans-3,4-Dihydroxycinnamoyl-CoA(4-)	ChEBI
trans-3,4-Dihydroxycinnamoyl-coenzyme A(4-)	ChEBI
trans-Caffeoyl-coenzyme A(4-)	ChEBI

Molecular Formula

C₃₀H₃₈N₇O₁₉P₃S

Average Mass

925.65

Monoisotopic Mass

925.117798519

IUPAC Name

(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)-N-{2-[(2-{[(2E)-3-(3,4-dioxidophenyl)prop-2-enoyl]sulfanyl}ethyl)-C-hydroxycarbonimidoyl]ethyl}-2-hydroxy-3,3-dimethylbutanecarboximidate

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])C1=CC([O-])=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/C30H42N7O19P3S/c1-30(2,25(43)28(44)33-8-7-20(40)32-9-10-60-21(41)6-4-16-3-5-17(38)18(39)11-16)13-53-59(50,51)56-58(48,49)52-12-19-24(55-57(45,46)47)23(42)29(54-19)37-15-36-22-26(31)34-14-35-27(22)37/h3-6,11,14-15,19,23-25,29,38-39,42-43H,7-10,12-13H2,1-2H3,(H,32,40)(H,33,44)(H,48,49)(H,50,51)(H2,31,34,35)(H2,45,46,47)/p-4/b6-4+/t19-,23-,24-,25+,29-/m1/s1

InChI Key

QHRGJMIMHCLHRG-ZSELIEHESA-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
Beta amino acid or derivatives
Glycosyl compound
Monosaccharide phosphate
Organic pyrophosphate
6-aminopurine
Imidazopyrimidine
Purine
Styrene
Catechol
Aminopyrimidine
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Pyrimidine
Alkyl phosphate
Monocyclic benzene moiety
Benzenoid
Fatty amide
Phosphoric acid ester
Imidolactam
Monosaccharide
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Tetrahydrofuran
Azole
Heteroaromatic compound
Imidazole
Secondary alcohol
Thiocarboxylic acid ester
Secondary carboxylic acid amide
Carboxamide group
Amino acid or derivatives
Carbothioic s-ester
Organoheterocyclic compound
Azacycle
Oxacycle
Sulfenyl compound
Thiocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Amine
Organooxygen compound
Organonitrogen compound
Carbonyl group
Alcohol
Organosulfur compound
Organopnictogen compound
Primary amine
Organic oxide
Hydrocarbon derivative
Organic nitrogen compound
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

caffeoyl-CoA(4-) (CHEBI:87136 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	0.069	ChemAxon
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	-6.3	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	422.39 Å²	ChemAxon
Rotatable Bond Count	22	ChemAxon
Refractivity	249.83 m³·mol⁻¹	ChemAxon
Polarizability	83.22 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

Spectrum Type	Description	Deposition Date	View
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

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	Proteobacteria	1	Human ; Human subgingival plaque
Bacteria	Firmicutes	1

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

Not Available

Chemspider ID

58145541

KEGG Compound ID

Not Available

BioCyc ID

CAFFEOYL-COA

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

45266599

PDB ID

Not Available

ChEBI ID

87136

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)-caffeoyl-CoA (MMDBc0055016)

MOL for #<Metabolite:0x00007fecf39a5b18>

3D MOL for #<Metabolite:0x00007fecf39a5b18>

3D SDF for #<Metabolite:0x00007fecf39a5b18>

3D-SDF for #<Metabolite:0x00007fecf39a5b18>

PDB for #<Metabolite:0x00007fecf39a5b18>

3D PDB for #<Metabolite:0x00007fecf39a5b18>

SMILES for #<Metabolite:0x00007fecf39a5b18>

INCHI for #<Metabolite:0x00007fecf39a5b18>

Structure for #<Metabolite:0x00007fecf39a5b18>

3D Structure for #<Metabolite:0x00007fecf39a5b18>