MiMeDB: Showing metabocard for 3-Oxooctadecanoyl-CoA (MMDBc0030306)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-18 00:02:39 UTC

Update Date

2022-08-31 17:43:29 UTC

Metabolite ID

MMDBc0030306

Metabolite Identification

Common Name

3-Oxooctadecanoyl-CoA

Description

3-Oxooctadecanoyl-CoA is a metabolite intermediate in the microsomal fatty acid chain elongation system. Microsomal electron-transport components NADPH-cytochrome P450 reductase (EC 1.6.2.4) and cytochrome b5 (EC 1.6.2.2) participate in the conversion from 3-Oxooctadecanoyl-CoA to beta-hydroxystearoyl-CoA, the first reductive step of the microsomal chain elongating system initiated by NADPH. (PMID: 6404652 )

Structure

MOL SDF PDB SMILES InChI


  Mrv1652305221921272D          

 73 75  0  0  1  0            999 V2000
    1.1370   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2527   26.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6027   26.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8514   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5659   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2804   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9948   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7093   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4238   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1383   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8527   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5672   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2817   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9961   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7106   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4251   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1396   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5698   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2843   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4264   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7119   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5685   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5711   31.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4277   27.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7424   33.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1018   33.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8540   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2856   31.5096    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.8553   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2830   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4075   34.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.5913   31.7871    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   24.0392   31.1740    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.4277   25.7346    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   26.1612   34.5828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3213   33.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.7132   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1788   32.5016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.4277   26.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.2474   35.4033    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1409   25.7346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9987   25.7346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.8286   34.0979    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.9887   32.9419    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.6539   34.5828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5143   33.2553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8540   26.5596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8553   24.4971    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.2830   26.5596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4117   31.7009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1421   25.3221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7132   24.4971    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   23.0456   30.4281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1497   29.2019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9846   29.2630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2691   29.1451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4441   30.5740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.9671   28.6221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3171   28.6221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5711   30.2721    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1421   27.7971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3718   32.3301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2108   30.3670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1421   29.4471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5977   29.8150    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.8566   29.8596    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.1421   28.6221    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.9974   25.3221    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.3287   30.6857    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.8869   31.0169    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.8677   31.9810    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.7132   26.1471    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.0026   32.5448    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 19 18  1  0  0  0  0
 21 20  1  0  0  0  0
 27 17  1  0  0  0  0
 27 22  1  0  0  0  0
 28 23  1  1  0  0  0
 29 18  1  0  0  0  0
 30 22  1  0  0  0  0
 33 28  1  0  0  0  0
 33 32  1  0  0  0  0
 35 31  2  0  0  0  0
 36 31  1  0  0  0  0
 37 34  1  0  0  0  0
 38 32  1  0  0  0  0
 39  2  1  0  0  0  0
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 39 24  1  0  0  0  0
 39 34  1  0  0  0  0
 40 35  1  0  0  0  0
 41 20  1  4  0  0  0
 41 29  2  0  0  0  0
 42 19  1  4  0  0  0
 42 37  2  0  0  0  0
 43 25  2  0  0  0  0
 43 35  1  0  0  0  0
 44 25  1  0  0  0  0
 44 36  2  0  0  0  0
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 45 31  1  0  0  0  0
 46 26  1  0  0  0  0
 46 36  1  0  0  0  0
 38 46  1  1  0  0  0
 47 27  2  0  0  0  0
 48 29  1  0  0  0  0
 49 30  2  0  0  0  0
 32 50  1  6  0  0  0
 34 51  1  6  0  0  0
 52 37  1  0  0  0  0
 60 23  1  0  0  0  0
 61 24  1  0  0  0  0
 62 28  1  0  0  0  0
 62 38  1  0  0  0  0
 33 63  1  1  0  0  0
 65 53  1  0  0  0  0
 65 54  1  0  0  0  0
 65 55  2  0  0  0  0
 65 63  1  0  0  0  0
 66 56  1  0  0  0  0
 66 57  2  0  0  0  0
 66 60  1  0  0  0  0
 66 64  1  0  0  0  0
 67 58  1  0  0  0  0
 67 59  2  0  0  0  0
 67 61  1  0  0  0  0
 67 64  1  0  0  0  0
 68 21  1  0  0  0  0
 68 30  1  0  0  0  0
 28 69  1  6  0  0  0
 32 70  1  1  0  0  0
 33 71  1  1  0  0  0
 34 72  1  6  0  0  0
 38 73  1  6  0  0  0
M  CHG  2  48  -1  52  -1
M  END


  Mrv1652305221921272D          

 73 75  0  0  1  0            999 V2000
    1.1370   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2527   26.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6027   26.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8514   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5659   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2804   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9948   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7093   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4238   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1383   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8527   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5672   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2817   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9961   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7106   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4251   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1396   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.5698   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.2843   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4264   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7119   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.5685   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5711   31.0971    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4277   27.3846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.7424   33.2774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1018   33.9697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8540   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2856   31.5096    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   16.8553   25.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2830   25.7346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.5913   31.7871    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   20.4277   25.7346    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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   25.3213   33.4268    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   24.1788   32.5016    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   20.4277   26.5596    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.1409   25.7346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9987   25.7346    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
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   24.6539   34.5828    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.5143   33.2553    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.8540   26.5596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.8553   24.4971    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   13.2830   26.5596    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4117   31.7009    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1421   25.3221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7132   24.4971    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   23.0456   30.4281    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.1497   29.2019    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.9846   29.2630    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.2691   29.1451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.4441   30.5740    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   20.3171   28.6221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   21.1421   27.7971    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.3718   32.3301    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.2108   30.3670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1421   29.4471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.5977   29.8150    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.8566   29.8596    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   21.1421   28.6221    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.9974   25.3221    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.3287   30.6857    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.8869   31.0169    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   23.8677   31.9810    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   19.7132   26.1471    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   25.0026   32.5448    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  1  1  0  0  0  0
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  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
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 62 38  1  0  0  0  0
 33 63  1  1  0  0  0
 65 53  1  0  0  0  0
 65 54  1  0  0  0  0
 65 55  2  0  0  0  0
 65 63  1  0  0  0  0
 66 56  1  0  0  0  0
 66 57  2  0  0  0  0
 66 60  1  0  0  0  0
 66 64  1  0  0  0  0
 67 58  1  0  0  0  0
 67 59  2  0  0  0  0
 67 61  1  0  0  0  0
 67 64  1  0  0  0  0
 68 21  1  0  0  0  0
 68 30  1  0  0  0  0
 28 69  1  6  0  0  0
 32 70  1  1  0  0  0
 33 71  1  1  0  0  0
 34 72  1  6  0  0  0
 38 73  1  6  0  0  0
M  CHG  2  48  -1  52  -1
M  END
> <DATABASE_ID>
MMDBc0030306

> <DATABASE_NAME>
MIME

> <SMILES>
[H][C@](O)(C([O-])=NCCC([O-])=NCCSC(=O)CC(=O)CCCCCCCCCCCCCCC)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/C39H68N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27(47)22-30(49)68-21-20-41-29(48)18-19-42-37(52)34(51)39(2,3)24-61-67(58,59)64-66(56,57)60-23-28-33(63-65(53,54)55)32(50)38(62-28)46-26-45-31-35(40)43-25-44-36(31)46/h25-26,28,32-34,38,50-51H,4-24H2,1-3H3,(H,41,48)(H,42,52)(H,56,57)(H,58,59)(H2,40,43,44)(H2,53,54,55)/p-2/t28-,32-,33-,34+,38-/m1/s1

> <INCHI_KEY>
LGOGWHDPDVAUNY-LFZQUHGESA-L

> <FORMULA>
C39H66N7O18P3S

> <MOLECULAR_WEIGHT>
1045.964

> <EXACT_MASS>
1045.339788569

> <JCHEM_ACCEPTOR_COUNT>
20

> <JCHEM_ATOM_COUNT>
134

> <JCHEM_AVERAGE_POLARIZABILITY>
104.03288281620652

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
-2

> <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)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(3-oxooctadecanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanecarboximidate

> <ALOGPS_LOGP>
3.27

> <JCHEM_LOGP>
2.4548256942276425

> <ALOGPS_LOGS>
-2.64

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.8916023308455228

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8196398768215625

> <JCHEM_PKA_STRONGEST_BASIC>
4.158013163671497

> <JCHEM_POLAR_SURFACE_AREA>
393.3400000000001

> <JCHEM_REFRACTIVITY>
268.6871000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
36

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.51e+00 g/l

> <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]-2-hydroxy-3,3-dimethyl-N-[2-({2-[(3-oxooctadecanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanecarboximidate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 22-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-MAY-19         0                                  
HETATM    1  C   UNK     0       2.122  47.268   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      39.672  49.578   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      36.592  49.578   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.456  48.038   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.790  47.268   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.123  48.038   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.457  47.268   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.791  48.038   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.124  47.268   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      11.458  48.038   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.792  47.268   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      14.125  48.038   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      15.459  47.268   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.793  48.038   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.126  47.268   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      19.460  48.038   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      20.794  47.268   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.797  48.038   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      34.131  47.268   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      28.796  47.268   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      27.462  48.038   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      23.461  47.268   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      42.133  58.048   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      38.132  51.118   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      49.919  62.118   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      44.990  63.410   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      22.128  48.038   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      43.466  58.818   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      31.463  47.268   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      24.795  48.038   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      47.427  63.928   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      45.904  59.336   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      44.873  58.191   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      38.132  48.038   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      48.834  64.555   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      47.266  62.397   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      36.798  47.268   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      45.134  60.670   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      38.132  49.578   0.000  0.00  0.00           C+0
HETATM   40  N   UNK     0      48.995  66.086   0.000  0.00  0.00           N+0
HETATM   41  N   UNK     0      30.130  48.038   0.000  0.00  0.00           N+0
HETATM   42  N   UNK     0      35.464  48.038   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      50.080  63.649   0.000  0.00  0.00           N+0
HETATM   44  N   UNK     0      48.512  61.491   0.000  0.00  0.00           N+0
HETATM   45  N   UNK     0      46.021  64.555   0.000  0.00  0.00           N+0
HETATM   46  N   UNK     0      45.760  62.076   0.000  0.00  0.00           N+0
HETATM   47  O   UNK     0      22.128  49.578   0.000  0.00  0.00           O+0
HETATM   48  O   UNK     0      31.463  45.728   0.000  0.00  0.00           O-1
HETATM   49  O   UNK     0      24.795  49.578   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0      47.435  59.175   0.000  0.00  0.00           O+0
HETATM   51  O   UNK     0      39.465  47.268   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      36.798  45.728   0.000  0.00  0.00           O-1
HETATM   53  O   UNK     0      43.019  56.799   0.000  0.00  0.00           O+0
HETATM   54  O   UNK     0      45.079  54.510   0.000  0.00  0.00           O+0
HETATM   55  O   UNK     0      42.905  54.624   0.000  0.00  0.00           O+0
HETATM   56  O   UNK     0      41.569  54.404   0.000  0.00  0.00           O+0
HETATM   57  O   UNK     0      40.029  57.072   0.000  0.00  0.00           O+0
HETATM   58  O   UNK     0      41.005  53.428   0.000  0.00  0.00           O+0
HETATM   59  O   UNK     0      37.925  53.428   0.000  0.00  0.00           O+0
HETATM   60  O   UNK     0      42.133  56.508   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0      39.465  51.888   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      43.627  60.349   0.000  0.00  0.00           O+0
HETATM   63  O   UNK     0      45.193  56.685   0.000  0.00  0.00           O+0
HETATM   64  O   UNK     0      39.465  54.968   0.000  0.00  0.00           O+0
HETATM   65  P   UNK     0      44.049  55.655   0.000  0.00  0.00           P+0
HETATM   66  P   UNK     0      40.799  55.738   0.000  0.00  0.00           P+0
HETATM   67  P   UNK     0      39.465  53.428   0.000  0.00  0.00           P+0
HETATM   68  S   UNK     0      26.129  47.268   0.000  0.00  0.00           S+0
HETATM   69  H   UNK     0      43.547  57.280   0.000  0.00  0.00           H+0
HETATM   70  H   UNK     0      46.456  57.898   0.000  0.00  0.00           H+0
HETATM   71  H   UNK     0      44.553  59.698   0.000  0.00  0.00           H+0
HETATM   72  H   UNK     0      36.798  48.808   0.000  0.00  0.00           H+0
HETATM   73  H   UNK     0      46.672  60.750   0.000  0.00  0.00           H+0
CONECT    1    4                                                            
CONECT    2   39                                                            
CONECT    3   39                                                            
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   27                                                       
CONECT   18   19   29                                                       
CONECT   19   18   42                                                       
CONECT   20   21   41                                                       
CONECT   21   20   68                                                       
CONECT   22   27   30                                                       
CONECT   23   28   60                                                       
CONECT   24   39   61                                                       
CONECT   25   43   44                                                       
CONECT   26   45   46                                                       
CONECT   27   17   22   47                                                  
CONECT   28   23   33   62   69                                             
CONECT   29   18   41   48                                                  
CONECT   30   22   49   68                                                  
CONECT   31   35   36   45                                                  
CONECT   32   33   38   50   70                                             
CONECT   33   28   32   63   71                                             
CONECT   34   37   39   51   72                                             
CONECT   35   31   40   43                                                  
CONECT   36   31   44   46                                                  
CONECT   37   34   42   52                                                  
CONECT   38   32   46   62   73                                             
CONECT   39    2    3   24   34                                             
CONECT   40   35                                                            
CONECT   41   20   29                                                       
CONECT   42   19   37                                                       
CONECT   43   25   35                                                       
CONECT   44   25   36                                                       
CONECT   45   26   31                                                       
CONECT   46   26   36   38                                                  
CONECT   47   27                                                            
CONECT   48   29                                                            
CONECT   49   30                                                            
CONECT   50   32                                                            
CONECT   51   34                                                            
CONECT   52   37                                                            
CONECT   53   65                                                            
CONECT   54   65                                                            
CONECT   55   65                                                            
CONECT   56   66                                                            
CONECT   57   66                                                            
CONECT   58   67                                                            
CONECT   59   67                                                            
CONECT   60   23   66                                                       
CONECT   61   24   67                                                       
CONECT   62   28   38                                                       
CONECT   63   33   65                                                       
CONECT   64   66   67                                                       
CONECT   65   53   54   55   63                                             
CONECT   66   56   57   60   64                                             
CONECT   67   58   59   61   64                                             
CONECT   68   21   30                                                       
CONECT   69   28                                                            
CONECT   70   32                                                            
CONECT   71   33                                                            
CONECT   72   34                                                            
CONECT   73   38                                                            
MASTER        0    0    0    0    0    0    0    0   73    0  150    0
END

Synonyms

Value	Source
3-Ketostearoyl-CoA	HMDB
3-Ketostearoyl-coenzyme A	HMDB
3-Oxostearoyl-CoA	HMDB
3-Oxostearoyl-coenzyme A	HMDB
beta-Ketostearoyl-CoA	HMDB
beta-Ketostearoyl-coenzyme A	HMDB

Molecular Formula

C₃₉H₆₆N₇O₁₈P₃S

Average Mass

1045.964

Monoisotopic Mass

1045.339788569

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)-2-hydroxy-3,3-dimethyl-N-[2-({2-[(3-oxooctadecanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanecarboximidate

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]-2-hydroxy-3,3-dimethyl-N-[2-({2-[(3-oxooctadecanoyl)sulfanyl]ethyl}-C-hydroxycarbonimidoyl)ethyl]butanecarboximidate

CAS Registry Number

86370-20-9

SMILES

[H][C@](O)(C([O-])=NCCC([O-])=NCCSC(=O)CC(=O)CCCCCCCCCCCCCCC)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/C39H68N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27(47)22-30(49)68-21-20-41-29(48)18-19-42-37(52)34(51)39(2,3)24-61-67(58,59)64-66(56,57)60-23-28-33(63-65(53,54)55)32(50)38(62-28)46-26-45-31-35(40)43-25-44-36(31)46/h25-26,28,32-34,38,50-51H,4-24H2,1-3H3,(H,41,48)(H,42,52)(H,56,57)(H,58,59)(H2,40,43,44)(H2,53,54,55)/p-2/t28-,32-,33-,34+,38-/m1/s1

InChI Key

LGOGWHDPDVAUNY-LFZQUHGESA-L

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated long aliphatic chain of 13 to 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acyl thioesters

Direct Parent

Long-chain 3-oxoacyl CoAs

Alternative Parents

Substituents

Coenzyme a or derivatives
Purine ribonucleoside 3',5'-bisphosphate
Purine ribonucleoside bisphosphate
Purine ribonucleoside diphosphate
Ribonucleoside 3'-phosphate
Pentose phosphate
Pentose-5-phosphate
Beta amino acid or derivatives
Glycosyl compound
N-glycosyl compound
6-aminopurine
Monosaccharide phosphate
Organic pyrophosphate
Pentose monosaccharide
Imidazopyrimidine
Purine
Monoalkyl phosphate
Aminopyrimidine
Alkyl phosphate
1,3-dicarbonyl compound
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Ketone
Thiocarboxylic acid ester
Secondary carboxylic acid amide
Amino acid or derivatives
Carboxamide group
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organopnictogen compound
Hydrocarbon derivative
Organic oxygen compound
Primary amine
Carbonyl group
Organic nitrogen compound
Organic oxide
Organosulfur compound
Organooxygen compound
Organonitrogen compound
Alcohol
Amine
Organic anion
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.51 g/L	ALOGPS
logP	3.27	ALOGPS
logP	2.45	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.16	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	20	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	393.34 Å²	ChemAxon
Rotatable Bond Count	36	ChemAxon
Refractivity	268.69 m³·mol⁻¹	ChemAxon
Polarizability	104.03 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-20	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference
MMDBr0000157	3-Oxooctadecanoyl-CoA	Acetyl-CoA	Acetyl-coa acyltransferase 1	Acetyl Coenzyme A Acyltransferase (Hexadecanoyl Coenzyme A), Peroxisomal	VMH	1679347
MMDBr0003864	Hydrogen Ion	3-Oxooctadecanoyl-CoA	Cathepsin a	RE0580L	VMH	10479480
MMDBr0003865	Hydrogen Ion	3-Oxooctadecanoyl-CoA	Elovl fatty acid elongase 1	RE0580R	VMH	10479480
MMDBr0003866	3-Oxooctadecanoyl-CoA	3-hydroxyoctadecanoyl-CoA	Not Available	RE0581C	VMH	30371894
MMDBr0003867	3-Oxooctadecanoyl-CoA	3-hydroxyoctadecanoyl-CoA	Elovl fatty acid elongase 1	RE0581R	VMH	10479480
MMDBr0009668	Hydrogen Ion	3-Oxooctadecanoyl-CoA	Elovl fatty acid elongase 1	Very-Long-Chain 3-Oxoacyl Coenzyme A Synthase	VMH	30371894
MMDBr0010029	3-hydroxyoctadecanoyl-CoA	3-Oxooctadecanoyl-CoA	Enoyl-coa, hydratase/3-hydroxyacyl coa dehydrogenase	3-Hydroxyacyl Coenzyme A Dehydrogenase	VMH	30371894
MMDBr0010050	3-hydroxyoctadecanoyl-CoA	3-Oxooctadecanoyl-CoA	Hydroxyacyl-coa dehydrogenase	3-Hydroxyacyl Coenzyme A Dehydrogenase	VMH	30371894
MMDBr0010051	3-Oxooctadecanoyl-CoA	Acetyl-CoA	Acetyl-coa acyltransferase 2	Acetyl Coenzyme A C-Acyltransferase	VMH	30371894
MMDBr0015398	Hydrogen Ion	3-Oxooctadecanoyl-CoA	Elongation of fatty acids protein 2	Fatty acid elongation	RHEA	34755880
MMDBr0015399	Hydrogen Ion	3-Oxooctadecanoyl-CoA	Elongation of fatty acids protein 2	Fatty acid elongation	RHEA	34755880
MMDBr0015663	3-Oxooctadecanoyl-CoA	(3R)-hydroxyoctadecanoyl-CoA	Very-long-chain 3-oxoacyl-CoA reductase	Reduction	RHEA	34755880
MMDBr0015664	3-Oxooctadecanoyl-CoA	(3R)-hydroxyoctadecanoyl-CoA	Very-long-chain 3-oxoacyl-CoA reductase	Reduction	RHEA	34755880
MMDBr0019513	Hydrogen Ion	Carbon dioxide	Elongation of fatty acids protein 1	Fatty acid elongation	PathBank	31602464
MMDBr0019515	Hydrogen Ion	NADP	3-oxoacyl-[acyl-carrier-protein] reductase	Reduction	PathBank	31602464
MMDBr0023318	NAD	Hydrogen Ion	2,3-dehydroadipyl-CoA hydratase	Hydration/dehydration of C-O bond	PathBank	31602464
MMDBr0023319	Coenzyme A	Acetyl-CoA	3-ketoacyl-CoA thiolase FadA	Carbon‚Äìcarbon-bond formation	PathBank	31602464
MMDBr0038771	3-Oxooctadecanoyl-CoA	3-oxooctadecanoic acid	Thioesterase TesA	Hydrolysis	RHEA	34755880

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Proteobacteria	1	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool	Unknown
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown

Exposure Sources

Source Type	Source Sub-type	Species	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Min	Max	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified									HMDB

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023942

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

22833663

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Bout A, Franse MM, Collins J, Blonden L, Tager JM, Benne R: Characterization of the gene encoding human peroxisomal 3-oxoacyl-CoA thiolase (ACAA). No large DNA rearrangement in a thiolase-deficient patient. Biochim Biophys Acta. 1991 Aug 27;1090(1):43-51. doi: 10.1016/0167-4781(91)90035-k. [PubMed:1679347 ]
Steinberg SJ, Wang SJ, McGuinness MC, Watkins PA: Human liver-specific very-long-chain acyl-coenzyme A synthetase: cDNA cloning and characterization of a second enzymatically active protein. Mol Genet Metab. 1999 Sep;68(1):32-42. doi: 10.1006/mgme.1999.2883. [PubMed:10479480 ]
Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]
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 3-Oxooctadecanoyl-CoA (MMDBc0030306)

MOL for #<Metabolite:0x000055d24ae86df0>

3D MOL for #<Metabolite:0x000055d24ae86df0>

3D SDF for #<Metabolite:0x000055d24ae86df0>

3D-SDF for #<Metabolite:0x000055d24ae86df0>

PDB for #<Metabolite:0x000055d24ae86df0>

3D PDB for #<Metabolite:0x000055d24ae86df0>

SMILES for #<Metabolite:0x000055d24ae86df0>

INCHI for #<Metabolite:0x000055d24ae86df0>

Structure for #<Metabolite:0x000055d24ae86df0>

3D Structure for #<Metabolite:0x000055d24ae86df0>