MiMeDB: Showing metabocard for 2,3-didehydroadipoyl-CoA (MMDBc0055284)

Microbial

Record Information

Version

2.0

Status

Detected and Quantified

Creation Date

2022-06-17 19:48:17 UTC

Update Date

2025-10-07 16:09:03 UTC

Metabolite ID

MMDBc0055284

Metabolite Identification

Common Name

2,3-didehydroadipoyl-CoA

Description

2,3-didehydroadipoyl-CoA is a member of the CoA thioester class of compounds, characterized by the presence of a didehydro-adipoyl moiety. Its chemical structure features a CoA moiety linked to a didehydro-adipate, which is derived from the dehydrogenation of adipic acid derivatives. This compound plays a role in various metabolic pathways, particularly in the catabolism of aromatic compounds. Notably, it is involved in the conversion process catalyzed by the enzyme PaaG, which transforms cis-3,4-didehydroadipoyl-CoA into trans-2,3-didehydroadipoyl-CoA, showcasing a Δ3,Δ2-enoyl-CoA isomerase-like mechanism that facilitates proton shuttling between distinct substrates (PMID:31689071 ). The presence of 2,3-didehydroadipoyl-CoA in metabolic pathways highlights its significance in the degradation of aromatic compounds, contributing to the overall understanding of microbial metabolism and the biochemical transformations of CoA derivatives.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652306172221482D          

 62 64  0  0  1  0            999 V2000
   -1.7347   14.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097   15.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6804   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9660   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6804   16.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2515   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3936   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1081   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3235   15.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0366   15.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4948   13.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8542   12.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0379   15.2177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9647   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3949   16.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5370   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1599   12.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3436   14.9402    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7916   15.5532    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6077   14.8052    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -9.9136   12.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0737   13.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9311   14.2257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3222   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9998   11.3240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.6791   14.8052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.8213   14.8052    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  -10.5810   12.6294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7411   13.7854    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.4062   12.1444    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2667   13.4720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9647   16.0427    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    9.3949   17.2802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.1094   16.0427    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.5370   13.9802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1641   15.0264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077   13.9802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068   16.0427    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -6.7980   16.2992    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -7.9021   17.5253    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -6.7369   17.4643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4820   14.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3070   16.3447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8781   14.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0531   16.3447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6090   15.2177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7511   15.2177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1242   14.3972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9631   16.3602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1800   16.0427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3500   16.9123    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8945   15.6302    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4656   15.6302    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.0811   16.0416    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.6201   14.7463    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.7550   14.1825    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  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
 15 11  1  1  0  0  0
 16  7  1  0  0  0  0
 17  5  1  0  0  0  0
  6 18  1  4  0  0  0
 21 15  1  0  0  0  0
 21 20  1  0  0  0  0
 23 19  2  0  0  0  0
 24 19  1  0  0  0  0
 25 22  1  0  0  0  0
 26 20  1  0  0  0  0
 27  1  1  0  0  0  0
 27  2  1  0  0  0  0
 27 12  1  0  0  0  0
 27 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29  9  1  4  0  0  0
 29 16  2  0  0  0  0
 30  8  1  4  0  0  0
 30 25  2  0  0  0  0
 31 13  2  0  0  0  0
 31 23  1  0  0  0  0
 32 13  1  0  0  0  0
 32 24  2  0  0  0  0
 33 14  2  0  0  0  0
 33 19  1  0  0  0  0
 34 14  1  0  0  0  0
 34 24  1  0  0  0  0
 26 34  1  1  0  0  0
 35 16  1  0  0  0  0
 36 17  2  0  0  0  0
 37 17  1  0  0  0  0
 38 18  2  0  0  0  0
 20 39  1  6  0  0  0
 22 40  1  1  0  0  0
 41 25  1  0  0  0  0
 49 11  1  0  0  0  0
 50 12  1  0  0  0  0
 51 15  1  0  0  0  0
 51 26  1  0  0  0  0
 21 52  1  1  0  0  0
 54 42  1  0  0  0  0
 54 43  1  0  0  0  0
 54 44  2  0  0  0  0
 54 52  1  0  0  0  0
 55 45  1  0  0  0  0
 55 46  2  0  0  0  0
 55 49  1  0  0  0  0
 55 53  1  0  0  0  0
 56 47  1  0  0  0  0
 56 48  2  0  0  0  0
 56 50  1  0  0  0  0
 56 53  1  0  0  0  0
 57 10  1  0  0  0  0
 57 18  1  0  0  0  0
 15 58  1  6  0  0  0
 20 59  1  1  0  0  0
 21 60  1  1  0  0  0
 22 61  1  1  0  0  0
 26 62  1  6  0  0  0
M  CHG  5  35  -1  37  -1  41  -1  42  -1  43  -1
M  END


  Mrv1652306172221482D          

 62 64  0  0  1  0            999 V2000
   -1.7347   14.5032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9097   15.9322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6804   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9660   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6804   16.0427    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2515   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2502   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5357   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3936   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1081   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3235   15.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0366   15.6302    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.4948   13.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8542   12.7575    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0379   15.2177    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9647   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3949   16.4552    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5370   14.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1599   12.4800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3436   14.9402    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -7.7916   15.5532    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   -9.9136   12.1444    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0737   13.3005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9311   14.2257    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3222   15.2177    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.9998   11.3240    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.2667   13.4720    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.9647   16.0427    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
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   10.1094   16.0427    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
    6.5370   13.9802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1641   15.0264    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077   13.9802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1068   16.0427    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -6.7980   16.2992    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -7.9021   17.5253    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   -6.7369   17.4643    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4820   14.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3070   16.3447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8781   14.9157    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0531   16.3447    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6090   15.2177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7511   15.2177    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1242   14.3972    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9631   16.3602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1800   16.0427    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3500   16.9123    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8945   15.6302    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4656   15.6302    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
    5.8226   15.2177    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0811   16.0416    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6393   15.7104    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6201   14.7463    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6077   15.6302    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7550   14.1825    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  3  1  0  0  0  0
  5  3  1  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
 15 11  1  1  0  0  0
 16  7  1  0  0  0  0
 17  5  1  0  0  0  0
  6 18  1  4  0  0  0
 21 15  1  0  0  0  0
 21 20  1  0  0  0  0
 23 19  2  0  0  0  0
 24 19  1  0  0  0  0
 25 22  1  0  0  0  0
 26 20  1  0  0  0  0
 27  1  1  0  0  0  0
 27  2  1  0  0  0  0
 27 12  1  0  0  0  0
 27 22  1  0  0  0  0
 28 23  1  0  0  0  0
 29  9  1  4  0  0  0
 29 16  2  0  0  0  0
 30  8  1  4  0  0  0
 30 25  2  0  0  0  0
 31 13  2  0  0  0  0
 31 23  1  0  0  0  0
 32 13  1  0  0  0  0
 32 24  2  0  0  0  0
 33 14  2  0  0  0  0
 33 19  1  0  0  0  0
 34 14  1  0  0  0  0
 34 24  1  0  0  0  0
 26 34  1  1  0  0  0
 35 16  1  0  0  0  0
 36 17  2  0  0  0  0
 37 17  1  0  0  0  0
 38 18  2  0  0  0  0
 20 39  1  6  0  0  0
 22 40  1  1  0  0  0
 41 25  1  0  0  0  0
 49 11  1  0  0  0  0
 50 12  1  0  0  0  0
 51 15  1  0  0  0  0
 51 26  1  0  0  0  0
 21 52  1  1  0  0  0
 54 42  1  0  0  0  0
 54 43  1  0  0  0  0
 54 44  2  0  0  0  0
 54 52  1  0  0  0  0
 55 45  1  0  0  0  0
 55 46  2  0  0  0  0
 55 49  1  0  0  0  0
 55 53  1  0  0  0  0
 56 47  1  0  0  0  0
 56 48  2  0  0  0  0
 56 50  1  0  0  0  0
 56 53  1  0  0  0  0
 57 10  1  0  0  0  0
 57 18  1  0  0  0  0
 15 58  1  6  0  0  0
 20 59  1  1  0  0  0
 21 60  1  1  0  0  0
 22 61  1  1  0  0  0
 26 62  1  6  0  0  0
M  CHG  5  35  -1  37  -1  41  -1  42  -1  43  -1
M  END
> <DATABASE_ID>
MMDBc0055284

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](O)(C([O-])=NCCC([O-])=NCCSC(=O)C=CCCC([O-])=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/C27H42N7O19P3S/c1-27(2,22(40)25(41)30-8-7-16(35)29-9-10-57-18(38)6-4-3-5-17(36)37)12-50-56(47,48)53-55(45,46)49-11-15-21(52-54(42,43)44)20(39)26(51-15)34-14-33-19-23(28)31-13-32-24(19)34/h4,6,13-15,20-22,26,39-40H,3,5,7-12H2,1-2H3,(H,29,35)(H,30,41)(H,36,37)(H,45,46)(H,47,48)(H2,28,31,32)(H2,42,43,44)/p-5/t15-,20-,21-,22+,26-/m1/s1

> <INCHI_KEY>
ZFXICKRXPZTFPB-BIEWRJSYSA-I

> <FORMULA>
C27H37N7O19P3S

> <MOLECULAR_WEIGHT>
888.61

> <EXACT_MASS>
888.110522067

> <JCHEM_ACCEPTOR_COUNT>
21

> <JCHEM_ATOM_COUNT>
94

> <JCHEM_AVERAGE_POLARIZABILITY>
77.74177755819724

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-5

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-({2-[(3-{[(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-1-oxidobutylidene]amino}-1-oxidopropylidene)amino]ethyl}sulfanyl)-6-oxohex-4-enoate

> <JCHEM_LOGP>
-3.30196526711576

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-5

> <JCHEM_PKA>
1.8893105186847947

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8194271333902705

> <JCHEM_PKA_STRONGEST_BASIC>
3.959934643711384

> <JCHEM_POLAR_SURFACE_AREA>
422.06000000000006

> <JCHEM_REFRACTIVITY>
224.1343000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
24

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
6-({2-[(3-{[(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]-2-hydroxy-3,3-dimethyl-1-oxidobutylidene]amino}-1-oxidopropylidene)amino]ethyl}sulfanyl)-6-oxohex-4-enoate

> <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      -3.238  27.073   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.698  29.740   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      16.203  28.406   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      14.870  27.636   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.203  29.946   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.536  28.406   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.200  27.636   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.867  28.406   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.201  28.406   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.535  27.636   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0     -11.804  29.176   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.802  29.176   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0     -19.590  25.106   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0     -14.661  23.814   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0     -13.137  28.406   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.534  28.406   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.537  30.716   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      12.202  27.636   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0     -17.098  23.296   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0     -15.575  27.888   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0     -14.544  29.033   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.134  27.636   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0     -18.505  22.670   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0     -16.937  24.828   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       0.199  28.406   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0     -14.805  26.555   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.468  28.406   0.000  0.00  0.00           C+0
HETATM   28  N   UNK     0     -18.666  21.138   0.000  0.00  0.00           N+0
HETATM   29  N   UNK     0       6.868  27.636   0.000  0.00  0.00           N+0
HETATM   30  N   UNK     0       1.533  27.636   0.000  0.00  0.00           N+0
HETATM   31  N   UNK     0     -19.751  23.575   0.000  0.00  0.00           N+0
HETATM   32  N   UNK     0     -18.183  25.733   0.000  0.00  0.00           N+0
HETATM   33  N   UNK     0     -15.692  22.670   0.000  0.00  0.00           N+0
HETATM   34  N   UNK     0     -15.431  25.148   0.000  0.00  0.00           N+0
HETATM   35  O   UNK     0       5.534  29.946   0.000  0.00  0.00           O-1
HETATM   36  O   UNK     0      17.537  32.256   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0      18.871  29.946   0.000  0.00  0.00           O-1
HETATM   38  O   UNK     0      12.202  26.096   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0     -17.106  28.049   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -1.134  26.096   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       0.199  29.946   0.000  0.00  0.00           O-1
HETATM   42  O   UNK     0     -12.690  30.425   0.000  0.00  0.00           O-1
HETATM   43  O   UNK     0     -14.751  32.714   0.000  0.00  0.00           O-1
HETATM   44  O   UNK     0     -12.576  32.600   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      -8.366  27.843   0.000  0.00  0.00           O+0
HETATM   46  O   UNK     0      -9.906  30.510   0.000  0.00  0.00           O+0
HETATM   47  O   UNK     0      -7.239  27.843   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      -5.699  30.510   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0     -10.470  28.406   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      -5.135  28.406   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0     -13.298  26.875   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0     -14.864  30.539   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      -7.803  29.946   0.000  0.00  0.00           O+0
HETATM   54  P   UNK     0     -13.720  31.570   0.000  0.00  0.00           P+0
HETATM   55  P   UNK     0      -9.136  29.176   0.000  0.00  0.00           P+0
HETATM   56  P   UNK     0      -6.469  29.176   0.000  0.00  0.00           P+0
HETATM   57  S   UNK     0      10.869  28.406   0.000  0.00  0.00           S+0
HETATM   58  H   UNK     0     -13.218  29.944   0.000  0.00  0.00           H+0
HETATM   59  H   UNK     0     -16.127  29.326   0.000  0.00  0.00           H+0
HETATM   60  H   UNK     0     -14.224  27.526   0.000  0.00  0.00           H+0
HETATM   61  H   UNK     0      -1.134  29.176   0.000  0.00  0.00           H+0
HETATM   62  H   UNK     0     -16.343  26.474   0.000  0.00  0.00           H+0
CONECT    1   27                                                            
CONECT    2   27                                                            
CONECT    3    4    5                                                       
CONECT    4    3    6                                                       
CONECT    5    3   17                                                       
CONECT    6    4   18                                                       
CONECT    7    8   16                                                       
CONECT    8    7   30                                                       
CONECT    9   10   29                                                       
CONECT   10    9   57                                                       
CONECT   11   15   49                                                       
CONECT   12   27   50                                                       
CONECT   13   31   32                                                       
CONECT   14   33   34                                                       
CONECT   15   11   21   51   58                                             
CONECT   16    7   29   35                                                  
CONECT   17    5   36   37                                                  
CONECT   18    6   38   57                                                  
CONECT   19   23   24   33                                                  
CONECT   20   21   26   39   59                                             
CONECT   21   15   20   52   60                                             
CONECT   22   25   27   40   61                                             
CONECT   23   19   28   31                                                  
CONECT   24   19   32   34                                                  
CONECT   25   22   30   41                                                  
CONECT   26   20   34   51   62                                             
CONECT   27    1    2   12   22                                             
CONECT   28   23                                                            
CONECT   29    9   16                                                       
CONECT   30    8   25                                                       
CONECT   31   13   23                                                       
CONECT   32   13   24                                                       
CONECT   33   14   19                                                       
CONECT   34   14   24   26                                                  
CONECT   35   16                                                            
CONECT   36   17                                                            
CONECT   37   17                                                            
CONECT   38   18                                                            
CONECT   39   20                                                            
CONECT   40   22                                                            
CONECT   41   25                                                            
CONECT   42   54                                                            
CONECT   43   54                                                            
CONECT   44   54                                                            
CONECT   45   55                                                            
CONECT   46   55                                                            
CONECT   47   56                                                            
CONECT   48   56                                                            
CONECT   49   11   55                                                       
CONECT   50   12   56                                                       
CONECT   51   15   26                                                       
CONECT   52   21   54                                                       
CONECT   53   55   56                                                       
CONECT   54   42   43   44   52                                             
CONECT   55   45   46   49   53                                             
CONECT   56   47   48   50   53                                             
CONECT   57   10   18                                                       
CONECT   58   15                                                            
CONECT   59   20                                                            
CONECT   60   21                                                            
CONECT   61   22                                                            
CONECT   62   26                                                            
MASTER        0    0    0    0    0    0    0    0   62    0  128    0
END

Synonyms

Value	Source
2,3-Didehydroadipoyl-CoA	ChEBI
2,3-Didehydroadipoyl-coenzyme A(5-)	ChEBI

Molecular Formula

C₂₇H₃₇N₇O₁₉P₃S

Average Mass

888.61

Monoisotopic Mass

888.110522067

IUPAC Name

6-({2-[(3-{[(2R)-4-({[({[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonooxy)oxolan-2-yl]methoxy}(hydroxy)phosphoryl)oxy](hydroxy)phosphoryl}oxy)-2-hydroxy-3,3-dimethyl-1-oxidobutylidene]amino}-1-oxidopropylidene)amino]ethyl}sulfanyl)-6-oxohex-4-enoate

Traditional Name

6-({2-[(3-{[(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]-2-hydroxy-3,3-dimethyl-1-oxidobutylidene]amino}-1-oxidopropylidene)amino]ethyl}sulfanyl)-6-oxohex-4-enoate

CAS Registry Number

Not Available

SMILES

[H][C@](O)(C([O-])=NCCC([O-])=NCCSC(=O)C=CCCC([O-])=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/C27H42N7O19P3S/c1-27(2,22(40)25(41)30-8-7-16(35)29-9-10-57-18(38)6-4-3-5-17(36)37)12-50-56(47,48)53-55(45,46)49-11-15-21(52-54(42,43)44)20(39)26(51-15)34-14-33-19-23(28)31-13-32-24(19)34/h4,6,13-15,20-22,26,39-40H,3,5,7-12H2,1-2H3,(H,29,35)(H,30,41)(H,36,37)(H,45,46)(H,47,48)(H2,28,31,32)(H2,42,43,44)/p-5/t15-,20-,21-,22+,26-/m1/s1

InChI Key

ZFXICKRXPZTFPB-BIEWRJSYSA-I

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain 2-enoyl coas. These are organic compounds containing a coenzyme A substructure linked to a medium-chain 2-enoyl chain of 5 to 12 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Medium-chain 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
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Imidazopyrimidine
Purine
Medium-chain fatty acid
Aminopyrimidine
Hydroxy fatty acid
Thia fatty acid
Monoalkyl phosphate
Alkyl phosphate
Monosaccharide
N-substituted imidazole
Organic phosphoric acid derivative
Phosphoric acid ester
Fatty acid
Imidolactam
Pyrimidine
Unsaturated fatty acid
Tetrahydrofuran
Azole
Imidazole
Heteroaromatic compound
Secondary alcohol
Carbothioic s-ester
Thiocarboxylic acid ester
Amino acid
Amino acid or derivatives
Organoheterocyclic compound
Carboximidic acid
Azacycle
Oxacycle
Carboximidic acid derivative
Carboxylic acid derivative
Carboxylic acid
Thiocarboxylic acid or derivatives
Monocarboxylic acid or derivatives
Sulfenyl compound
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Primary amine
Organic oxide
Alcohol
Organic nitrogen compound
Organooxygen compound
Organosulfur compound
Hydrocarbon derivative
Organonitrogen compound
Amine
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

acyl-CoA oxoanion (CHEBI:71044 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
logP	-3.3	ChemAxon
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	3.96	ChemAxon
Physiological Charge	-5	ChemAxon
Hydrogen Acceptor Count	21	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	422.06 Å²	ChemAxon
Rotatable Bond Count	24	ChemAxon
Refractivity	224.13 m³·mol⁻¹	ChemAxon
Polarizability	77.74 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

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Chromatography Type	Technique	Column	Deposition Date	Retention Time (s)
Liquid Chromatography	HILIC	Waters Acquity UPLC-BEH Amide column (void)	2025-10-24	569.8
Liquid Chromatography	HILIC	Accucore 150 Amide HILIC (eluted)	2025-10-24	366.8
Liquid Chromatography	Reversed-phase	Hypersil Gold 1.9 µm C18 (eluted)	2025-10-24	476.1
Liquid Chromatography	Reversed-phase	Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) (eluted)	2025-10-24	510.2
Liquid Chromatography	Reversed-phase	XBridge C18 3.5u 2.1x50 mm (eluted)	2025-10-24	387.8
Liquid Chromatography	Reversed-phase	Ascentis Express C18 (eluted)	2025-10-24	166.2
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	2038.6
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	398.1
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC (eluted)	2025-10-24	374.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	167.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-HILIC (eluted)	2025-10-24	201.5
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC HSS T3 C18 (eluted)	2025-10-24	160.0
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	119.4
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	268.3
Liquid Chromatography	HILIC	Merck SeQuant ZIC-pHILIC column (eluted)	2025-10-24	363.3
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (void)	2025-10-24	100.8
Liquid Chromatography	Reversed-phase	Waters ACQUITY UPLC BEH C18 (eluted)	2025-10-24	216.8
Liquid Chromatography	Reversed-phase	Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex (eluted)	2025-10-24	950.7
Liquid Chromatography	Reversed-phase	Waters Atlantis T3 (2.1 x 150 mm, 5 um) (eluted)	2025-10-24	784.5

Retention Indices

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

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0019191	3-Oxo-5,6-dehydrosuberyl-CoA	2,3-didehydroadipoyl-CoA	3-oxoadipyl-CoA/3-oxo-5,6-dehydrosuberyl-CoA thiolase	Carbon‚Äìcarbon-bond formation	PathBank	31602464
MMDBr0019192	2,3-didehydroadipoyl-CoA	3-Hydroxyadipyl-CoA	2,3-dehydroadipyl-CoA hydratase	Hydration/dehydration of C-O bond	PathBank	31602464

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference

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

28533423

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139031597

PDB ID

Not Available

ChEBI ID

71044

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Wishart DS, Li C, Marcu A, Badran H, Pon A, Budinski Z, Patron J, Lipton D, Cao X, Oler E, Li K, Paccoud M, Hong C, Guo AC, Chan C, Wei W, Ramirez-Gaona M: PathBank: a comprehensive pathway database for model organisms. Nucleic Acids Res. 2020 Jan 8;48(D1):D470-D478. doi: 10.1093/nar/gkz861. [PubMed:31602464 ]
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 2,3-didehydroadipoyl-CoA (MMDBc0055284)

MOL for #<Metabolite:0x00007f9af25dd308>

3D MOL for #<Metabolite:0x00007f9af25dd308>

3D SDF for #<Metabolite:0x00007f9af25dd308>

3D-SDF for #<Metabolite:0x00007f9af25dd308>

PDB for #<Metabolite:0x00007f9af25dd308>

3D PDB for #<Metabolite:0x00007f9af25dd308>

SMILES for #<Metabolite:0x00007f9af25dd308>

INCHI for #<Metabolite:0x00007f9af25dd308>

Structure for #<Metabolite:0x00007f9af25dd308>

3D Structure for #<Metabolite:0x00007f9af25dd308>