MiMeDB: Showing metabocard for Docosanoyl-CoA (MMDBc0047837)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 15:45:11 UTC

Update Date

2022-12-15 22:52:17 UTC

Metabolite ID

MMDBc0047837

Metabolite Identification

Common Name

Docosanoyl-CoA

Description

Docosanoyl-CoA belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives. The second step, transfer of the acyl group to CoA (the same molecule that carries acetyl groups as acetyl-CoA), conserves free energy in the formation of a thioester bond. Docosanoyl-CoA is a strong basic compound (based on its pKa). Within humans, docosanoyl-CoA participates in a number of enzymatic reactions. In particular, docosanoyl-CoA and glycerol 3-phosphate can be converted into lpa(22:0/0:0); which is catalyzed by the enzyme glycerol-3-phosphate acyltransferase. In addition, lpa(22:0/0:0) and docosanoyl-CoA can be converted into PA(22:0/22:0); which is mediated by the enzyme 1-acyl-sn-glycerol-3-phosphate acyltransferase. In humans, docosanoyl-CoA is involved in the metabolic disorder called de novo triacylglycerol biosynthesis pathway. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. has a free energy change near zero. To be oxidatively degraded, a fatty acid must first be activated in a two-step reaction catalyzed by acyl-CoA synthetase. Fatty acids are activated in the cytosol, but oxidation occurs in the mitochondria. The CoA is then removed from the chain, carrying two carbons from the chain with it, forming acetyl-CoA. Docosanoyl-CoA is a acyl-CoA with the C-22 fatty acid Acyl chain moiety.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02251208112D          

 71 73  0  0  1  0            999 V2000
    6.6757   -9.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3402  -10.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8251  -10.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4896  -11.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9745  -12.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6390  -12.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1239  -13.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7883  -14.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2732  -14.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9376  -15.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4225  -16.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0870  -17.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5719  -17.8392    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2364  -18.5929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7213  -19.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3858  -20.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5351  -21.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.6845  -22.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1694  -23.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8338  -24.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.3188  -24.9447    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.1392  -24.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6241  -25.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4446  -25.4396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9295  -26.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5940  -26.8607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7500  -26.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2349  -26.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0554  -26.6021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5403  -27.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.6963  -26.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9427  -26.0940    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4500  -26.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0319  -25.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.8825  -24.2548    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.1288  -23.9192    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
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   15.2180  -23.5011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.7331  -22.8337    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.0657  -23.3186    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   15.4006  -22.3488    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2482  -22.1663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4277  -22.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9428  -21.5851    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1179  -21.5851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8629  -20.8005    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   12.5304  -19.4906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1978  -20.8005    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9824  -20.5456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5955  -21.0976    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
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   11.0783  -20.5456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4109  -21.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7435  -20.5456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9984  -19.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5859  -19.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7609  -19.0465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9984  -18.3320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8234  -18.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2359  -19.0465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8234  -19.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
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 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
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 18 19  1  0  0  0  0
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 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
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 25 26  1  0  0  0  0
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 31 32  1  0  0  0  0
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 35 36  1  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  1  0  0  0  0
 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
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 46 49  1  0  0  0  0
 49 50  1  0  0  0  0
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 51 52  1  0  0  0  0
 51 56  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 62  1  1  0  0  0
 54 55  1  1  0  0  0
 54 56  1  0  0  0  0
 56 57  1  1  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 60  1  0  0  0  0
 58 61  2  0  0  0  0
 62 63  1  0  0  0  0
 62 71  1  0  0  0  0
 63 64  2  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 65 71  2  0  0  0  0
 66 67  1  0  0  0  0
 66 68  2  0  0  0  0
 68 69  1  0  0  0  0
 69 70  2  0  0  0  0
 70 71  1  0  0  0  0
M  CHG  4  43  -1  47  -1  59  -1  60  -1
M  END


  Mrv0541 02251208112D          

 71 73  0  0  1  0            999 V2000
    6.6757   -9.3127    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3402  -10.0663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8251  -10.7337    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4896  -11.4874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9745  -12.1548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6390  -12.9085    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1239  -13.5759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7883  -14.3296    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2732  -14.9970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9376  -15.7507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4225  -16.4182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0870  -17.1718    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.7213  -19.2603    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3858  -20.0140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.5351  -21.4350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0200  -22.1025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6845  -22.8561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1694  -23.5236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8338  -24.2773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0134  -24.3635    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3188  -24.9447    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.1392  -24.8585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6241  -25.5259    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4446  -25.4396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.9295  -26.1071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5940  -26.8607    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.7500  -26.0208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2349  -26.6883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0554  -26.6021    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.5403  -27.2695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2047  -28.0231    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   14.8457  -27.8506    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.6963  -26.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   15.4500  -26.7651    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0319  -25.6759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5470  -25.0085    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   14.1288  -23.9192    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
   15.6362  -24.5904    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.2180  -23.5011    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   14.2482  -22.1663    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.4277  -22.2525    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9428  -21.5851    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.1179  -21.5851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.8629  -20.8005    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   12.5304  -20.3156    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   12.5304  -19.4906    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.1978  -20.8005    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   13.9824  -20.5456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.5955  -21.0976    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.0435  -21.7107    0.0000 O   0  5  0  0  0  0  0  0  0  0  0  0
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   15.2085  -21.6496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.0783  -20.5456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4109  -21.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7435  -20.5456    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9984  -19.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    9.9984  -18.3320    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8234  -18.3320    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2359  -19.0465    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.8234  -19.7609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
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  8  9  1  0  0  0  0
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 10 11  1  0  0  0  0
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 40 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 42 44  2  0  0  0  0
 42 45  1  0  0  0  0
 45 46  1  0  0  0  0
 46 47  1  0  0  0  0
 46 48  2  0  0  0  0
 46 49  1  0  0  0  0
 49 50  1  0  0  0  0
 51 50  1  1  0  0  0
 51 52  1  0  0  0  0
 51 56  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 53 62  1  1  0  0  0
 54 55  1  1  0  0  0
 54 56  1  0  0  0  0
 56 57  1  1  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 58 60  1  0  0  0  0
 58 61  2  0  0  0  0
 62 63  1  0  0  0  0
 62 71  1  0  0  0  0
 63 64  2  0  0  0  0
 64 65  1  0  0  0  0
 65 66  1  0  0  0  0
 65 71  2  0  0  0  0
 66 67  1  0  0  0  0
 66 68  2  0  0  0  0
 68 69  1  0  0  0  0
 69 70  2  0  0  0  0
 70 71  1  0  0  0  0
M  CHG  4  43  -1  47  -1  59  -1  60  -1
M  END
> <DATABASE_ID>
MMDBc0047837

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@@H](O)[C@H]1OP([O-])([O-])=O)N1C=NC2=C1N=CN=C2N

> <INCHI_IDENTIFIER>
InChI=1S/C43H78N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-34(52)71-27-26-45-33(51)24-25-46-41(55)38(54)43(2,3)29-64-70(61,62)67-69(59,60)63-28-32-37(66-68(56,57)58)36(53)42(65-32)50-31-49-35-39(44)47-30-48-40(35)50/h30-32,36-38,42,53-54H,4-29H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58)/p-4/t32-,36+,37+,38?,42-/m1/s1

> <INCHI_KEY>
NDDZLVOCGALPLR-JEAMVCTESA-J

> <FORMULA>
C43H74N7O17P3S

> <MOLECULAR_WEIGHT>
1086.071

> <EXACT_MASS>
1085.407474203

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
112.63551030379752

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
-4

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3-[(2-{[2-(docosanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl ({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate

> <ALOGPS_LOGP>
4.55

> <JCHEM_LOGP>
2.1721296120336486

> <ALOGPS_LOGS>
-4.44

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.8334045176178524

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8252479627216065

> <JCHEM_PKA_STRONGEST_BASIC>
4.946047024039826

> <JCHEM_POLAR_SURFACE_AREA>
374.9499999999999

> <JCHEM_REFRACTIVITY>
259.76710000000014

> <JCHEM_ROTATABLE_BOND_COUNT>
40

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.18e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2-{[2-(docosanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl {[(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxyphosphonate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-FEB-12         0                                  
HETATM    1  C   UNK     0      12.461 -17.384   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.835 -18.790   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.740 -20.036   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.114 -21.443   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.019 -22.689   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      12.393 -24.096   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.298 -25.342   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      12.671 -26.749   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      13.577 -27.994   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      12.950 -29.401   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      13.855 -30.647   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      13.229 -32.054   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.134 -33.300   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      13.508 -34.707   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      14.413 -35.953   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.787 -37.359   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      14.692 -38.605   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.066 -40.012   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      14.971 -41.258   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      14.344 -42.665   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      15.250 -43.911   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      14.623 -45.318   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      13.092 -45.479   0.000  0.00  0.00           O+0
HETATM   24  S   UNK     0      15.528 -46.563   0.000  0.00  0.00           S+0
HETATM   25  C   UNK     0      17.060 -46.403   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      17.965 -47.648   0.000  0.00  0.00           C+0
HETATM   27  N   UNK     0      19.497 -47.487   0.000  0.00  0.00           N+0
HETATM   28  C   UNK     0      20.402 -48.733   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      19.775 -50.140   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      21.933 -48.572   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      22.838 -49.818   0.000  0.00  0.00           C+0
HETATM   32  N   UNK     0      24.370 -49.657   0.000  0.00  0.00           N+0
HETATM   33  C   UNK     0      25.275 -50.903   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      24.649 -52.310   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      26.807 -50.742   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      27.712 -51.988   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0      27.433 -49.335   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      26.026 -48.709   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      28.840 -49.962   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      28.060 -47.928   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      27.154 -46.683   0.000  0.00  0.00           O+0
HETATM   42  P   UNK     0      27.781 -45.276   0.000  0.00  0.00           P+0
HETATM   43  O   UNK     0      26.374 -44.649   0.000  0.00  0.00           O-1
HETATM   44  O   UNK     0      29.188 -45.902   0.000  0.00  0.00           O+0
HETATM   45  O   UNK     0      28.407 -43.869   0.000  0.00  0.00           O+0
HETATM   46  P   UNK     0      27.502 -42.623   0.000  0.00  0.00           P+0
HETATM   47  O   UNK     0      26.256 -43.528   0.000  0.00  0.00           O-1
HETATM   48  O   UNK     0      28.748 -41.718   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0      26.597 -41.377   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0      25.065 -41.538   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      24.160 -40.292   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      22.620 -40.292   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0      22.144 -38.828   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      23.390 -37.922   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      23.390 -36.382   0.000  0.00  0.00           O+0
HETATM   56  C   UNK     0      24.636 -38.828   0.000  0.00  0.00           C+0
HETATM   57  O   UNK     0      26.100 -38.352   0.000  0.00  0.00           O+0
HETATM   58  P   UNK     0      27.245 -39.382   0.000  0.00  0.00           P+0
HETATM   59  O   UNK     0      26.215 -40.527   0.000  0.00  0.00           O-1
HETATM   60  O   UNK     0      28.275 -38.238   0.000  0.00  0.00           O-1
HETATM   61  O   UNK     0      28.389 -40.413   0.000  0.00  0.00           O+0
HETATM   62  N   UNK     0      20.679 -38.352   0.000  0.00  0.00           N+0
HETATM   63  C   UNK     0      19.434 -39.257   0.000  0.00  0.00           C+0
HETATM   64  N   UNK     0      18.188 -38.352   0.000  0.00  0.00           N+0
HETATM   65  C   UNK     0      18.664 -36.887   0.000  0.00  0.00           C+0
HETATM   66  C   UNK     0      17.894 -35.553   0.000  0.00  0.00           C+0
HETATM   67  N   UNK     0      16.354 -35.553   0.000  0.00  0.00           N+0
HETATM   68  N   UNK     0      18.664 -34.220   0.000  0.00  0.00           N+0
HETATM   69  C   UNK     0      20.204 -34.220   0.000  0.00  0.00           C+0
HETATM   70  N   UNK     0      20.974 -35.553   0.000  0.00  0.00           N+0
HETATM   71  C   UNK     0      20.204 -36.887   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    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   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38   39   40                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
CONECT   40   37   41                                                       
CONECT   41   40   42                                                       
CONECT   42   41   43   44   45                                             
CONECT   43   42                                                            
CONECT   44   42                                                            
CONECT   45   42   46                                                       
CONECT   46   45   47   48   49                                             
CONECT   47   46                                                            
CONECT   48   46                                                            
CONECT   49   46   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52   56                                                  
CONECT   52   51   53                                                       
CONECT   53   52   54   62                                                  
CONECT   54   53   55   56                                                  
CONECT   55   54                                                            
CONECT   56   51   54   57                                                  
CONECT   57   56   58                                                       
CONECT   58   57   59   60   61                                             
CONECT   59   58                                                            
CONECT   60   58                                                            
CONECT   61   58                                                            
CONECT   62   53   63   71                                                  
CONECT   63   62   64                                                       
CONECT   64   63   65                                                       
CONECT   65   64   66   71                                                  
CONECT   66   65   67   68                                                  
CONECT   67   66                                                            
CONECT   68   66   69                                                       
CONECT   69   68   70                                                       
CONECT   70   69   71                                                       
CONECT   71   62   65   70                                                  
MASTER        0    0    0    0    0    0    0    0   71    0  146    0
END

Synonyms

Value	Source
Behenoyl-CoA	HMDB
Behenoyl-coenzyme A	HMDB

Molecular Formula

C₄₃H₇₄N₇O₁₇P₃S

Average Mass

1086.071

Monoisotopic Mass

1085.407474203

IUPAC Name

3-[(2-{[2-(docosanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl ({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate

Traditional Name

3-[(2-{[2-(docosanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropyl {[(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxyphosphonate

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP([O-])(=O)OP([O-])(=O)OC[C@H]1O[C@H]([C@@H](O)[C@H]1OP([O-])([O-])=O)N1C=NC2=C1N=CN=C2N

InChI Identifier

InChI=1S/C43H78N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-22-23-34(52)71-27-26-45-33(51)24-25-46-41(55)38(54)43(2,3)29-64-70(61,62)67-69(59,60)63-28-32-37(66-68(56,57)58)36(53)42(65-32)50-31-49-35-39(44)47-30-48-40(35)50/h30-32,36-38,42,53-54H,4-29H2,1-3H3,(H,45,51)(H,46,55)(H,59,60)(H,61,62)(H2,44,47,48)(H2,56,57,58)/p-4/t32-,36+,37+,38?,42-/m1/s1

InChI Key

NDDZLVOCGALPLR-JEAMVCTESA-J

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tetrahydroisoquinolines. These are tetrahydrogenated isoquinoline derivatives.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Tetrahydroisoquinolines

Sub Class

Not Available

Direct Parent

Tetrahydroisoquinolines

Alternative Parents

Substituents

Alpha-amino acid
Alpha-amino acid or derivatives
Tetrahydroisoquinoline
1-hydroxy-2-unsubstituted benzenoid
Aralkylamine
Benzenoid
Amino acid or derivatives
Carboxylic acid salt
Amino acid
Carboxylic acid derivative
Carboxylic acid
Secondary aliphatic amine
Monocarboxylic acid or derivatives
Secondary amine
Azacycle
Organonitrogen compound
Organopnictogen compound
Amine
Organic oxygen compound
Organic oxide
Organic nitrogen compound
Organooxygen compound
Hydrocarbon derivative
Organic zwitterion
Carbonyl group
Organic salt
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	0.042 g/L	ALOGPS
logP	4.55	ALOGPS
logP	2.17	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	0.83	ChemAxon
pKa (Strongest Basic)	4.95	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	374.95 Å²	ChemAxon
Rotatable Bond Count	40	ChemAxon
Refractivity	259.77 m³·mol⁻¹	ChemAxon
Polarizability	112.64 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000l-9000000100-a158e5606a5d90017289	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9003010000-75491be5874083bd5ad9	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0005-9736700400-9b2f9daf6b95d3bdc5cd	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-001i-9002000000-8065dc007f3cdb6266ad	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000x-9034000000-bb3372fa3ac153bb5b14	2016-09-14	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-01rt-9401000000-067c7985ba9bd36cae3e	2016-09-14	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

Reactions

Reaction ID	Precursor	Product	Enzyme	Data Source	Reference
MMDBr0003850	trans-docos-2-enoyl-CoA	Docosanoyl-CoA	cyclin-dependent kinase 2 interacting protein	VMH	10479480
MMDBr0003851	Docosanoyl-CoA	3-oxotetracosanoyl-CoA	HIRA interacting protein 3	VMH	10479480
MMDBr0003858	Docosanoyl-CoA	Behenic acid	acyl-CoA thioesterase 1	VMH	10092594 10578051 16103133 16940157 9153233
MMDBr0003859	Docosanoyl-CoA	Behenic acid	acyl-CoA thioesterase 2	VMH	10092594 10578051 16103133 16940157 9153233
MMDBr0003860	Docosanoyl-CoA	Behenic acid	acyl-CoA thioesterase 4	VMH	10092594 10578051 16103133 16940157 9153233
MMDBr0005134	Behenic acid	Docosanoyl-CoA	acyl-CoA synthetase bubblegum family member 1	VMH	16868315 17762044
MMDBr0005283	Docosanoyl-CoA	Eicosanoyl-CoA	acetyl-CoA acyltransferase 1	VMH	11124748
MMDBr0005287	Tetracosanoyl-CoA	Docosanoyl-CoA	acetyl-CoA acyltransferase 1	VMH	2117919
MMDBr0009335	Docosanoyl-CoA	1-Docosanoyl-Glycero-3-Phosphate	1-acylglycerol-3-phosphate O-acyltransferase 6	VMH	30371894
MMDBr0009670	trans-docos-2-enoyl-CoA	Docosanoyl-CoA	trans-2,3-enoyl-CoA reductase	VMH	30371894
MMDBr0009671	Docosanoyl-CoA	3-oxotetracosanoyl-CoA	ELOVL fatty acid elongase 1	VMH	30371894
MMDBr0009816	Docosanoylcarnitine	L-Carnitine	carnitine palmitoyltransferase 1A (liver)	VMH	30371894
MMDBr0009984	Behenic acid	Docosanoyl-CoA	Not Available	VMH	30371894
MMDBr0010018	3-oxotetracosanoyl-CoA	Docosanoyl-CoA	acetyl-CoA acyltransferase 1	VMH	30371894
MMDBr0010019	Docosanoyl-CoA	trans-docos-2-enoyl-CoA	acyl-CoA oxidase 1, palmitoyl	VMH	30371894
MMDBr0010040	Docosanoyl-CoA	trans-docos-2-enoyl-CoA	acyl-CoA dehydrogenase family, member 9	VMH	30371894
MMDBr0010230	Cholesterol	Cholest-5-En-3Beta-Yl Docosanoate	sterol O-acyltransferase 1	VMH; KEGG	30371894

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
Eukaryota/Fungi	Ascomycota	2	Human feces; Human saliva	Unknown

Exposure Sources

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

FDB029210

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

53481548

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

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 ]
Cater NB, Denke MA: Behenic acid is a cholesterol-raising saturated fatty acid in humans. Am J Clin Nutr. 2001 Jan;73(1):41-4. doi: 10.1093/ajcn/73.1.41. [PubMed:11124748 ]
Fourcade S, Ruiz M, Camps C, Schluter A, Houten SM, Mooyer PA, Pampols T, Dacremont G, Wanders RJ, Giros M, Pujol A: A key role for the peroxisomal ABCD2 transporter in fatty acid homeostasis. Am J Physiol Endocrinol Metab. 2009 Jan;296(1):E211-21. doi: 10.1152/ajpendo.90736.2008. Epub 2008 Oct 14. [PubMed:18854420 ]
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 Docosanoyl-CoA (MMDBc0047837)

MOL for #<Metabolite:0x00007fdb50a8a970>

3D MOL for #<Metabolite:0x00007fdb50a8a970>

3D SDF for #<Metabolite:0x00007fdb50a8a970>

3D-SDF for #<Metabolite:0x00007fdb50a8a970>

PDB for #<Metabolite:0x00007fdb50a8a970>

3D PDB for #<Metabolite:0x00007fdb50a8a970>

SMILES for #<Metabolite:0x00007fdb50a8a970>

INCHI for #<Metabolite:0x00007fdb50a8a970>

Structure for #<Metabolite:0x00007fdb50a8a970>

3D Structure for #<Metabolite:0x00007fdb50a8a970>