MiMeDB: Showing metabocard for myristoyl-CoA (MMDBc0033017)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2021-11-19 04:31:16 UTC

Update Date

2024-04-20 06:15:31 UTC

Metabolite ID

MMDBc0033017

Metabolite Identification

Common Name

myristoyl-CoA

Description

Tetradecanoyl-CoA (or myristoyl-CoA) is an intermediate in fatty acid biosynthesis, fatty acid elongation and the beta oxidation of fatty acids. It is also used in the myristoylation of proteins. The first pass through the beta-oxidation process starts with the saturated fatty acid palmitoyl-CoA and produces myristoyl-CoA. A total of four enzymatic steps are required, starting with VLCAD CoA dehydrogenase (Very Long Chain) activity, followed by three enzymatic steps catalyzed by enoyl-CoA hydratase, 3-hydroxyacyl-CoA dehydrogenase, and ketoacyl-CoA thiolase, all present in the mitochondria. Myristoylation of proteins is also catalyzed by the presence of myristoyl-CoA along with Myristoyl-CoA:protein N-myristoyltransferase (NMT). Myristoylation is an irreversible, co-translational (during translation) protein modification found in animals, plants, fungi and viruses. In this protein modification a myristoyl group (derived from myristioyl CoA) is covalently attached via an amide bond to the alpha-amino group of an N-terminal amino acid of a nascent polypeptide. It is more common on glycine residues but also occurs on other amino acids. Myristoylation also occurs post-translationally, for example when previously internal glycine residues become exposed by caspase cleavage during apoptosis. Myristoylation plays a vital role in membrane targeting and signal transduction in plant responses to environmental stress. Compared to other species that possess a single functional myristoyl-CoA: protein N-myristoyltransferase (NMT) gene copy, human, mouse and cow possess 2 NMT genes, and more than 2 protein isoforms.

Structure

MOL SDF PDB SMILES InChI

      ChEBI
  Mrv1652308111921362D          

 63 65  0  0  1  0            999 V2000
   15.7708  -19.0508    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1034  -18.5659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5157  -19.8354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4358  -19.0508    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6908  -19.8354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0007  -20.5029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0249  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7677  -23.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3104  -23.5044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5959  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8815  -23.5044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3388  -21.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5959  -22.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3388  -21.0294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9099  -21.0294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6243  -20.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0532  -19.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9262  -18.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3388  -19.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7513  -18.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6243  -19.7917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9098  -19.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7677  -19.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4178  -19.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0677  -19.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5928  -18.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5928  -20.2043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2427  -18.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2427  -20.2043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5928  -19.3793    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.2427  -19.3793    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.6512  -18.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2058  -20.5029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3808  -21.3280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0308  -21.3280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2058  -21.3280    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.2058  -22.1530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5553  -18.7960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1686  -19.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8909  -18.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8830  -18.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1686  -20.1730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7115  -18.1284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5975  -19.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8830  -20.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5975  -20.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3119  -18.9353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4822  -23.0919    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.9112  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6257  -23.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3402  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0546  -23.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7691  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4836  -23.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1980  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9125  -23.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6270  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3416  -23.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0560  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1968  -23.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1968  -24.3294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7704  -23.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4847  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 38  1  1  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  6  0  0  0
  4 32  1  1  0  0  0
  5  4  1  0  0  0  0
  5 33  1  6  0  0  0
  9  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 48  1  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 14  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
 19 18  1  0  0  0  0
 21 19  1  0  0  0  0
 19 20  1  0  0  0  0
 21 22  1  6  0  0  0
 23 30  1  0  0  0  0
 30 24  1  0  0  0  0
 24 31  1  0  0  0  0
 31 25  1  0  0  0  0
 32 25  1  0  0  0  0
 30 26  2  0  0  0  0
 30 27  1  0  0  0  0
 31 28  2  0  0  0  0
 31 29  1  0  0  0  0
 33 36  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
 40 38  1  0  0  0  0
 41 39  2  0  0  0  0
 42 39  1  0  0  0  0
 43 40  2  0  0  0  0
 44 41  1  0  0  0  0
 43 41  1  0  0  0  0
 45 42  2  0  0  0  0
 46 44  2  0  0  0  0
 47 44  1  0  0  0  0
 46 45  1  0  0  0  0
 48 60  1  0  0  0  0
 60 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 60 61  2  0  0  0  0
 59 62  1  0  0  0  0
 62 63  1  0  0  0  0
M  END

      ChEBI
  Mrv1652308111921362D          

 63 65  0  0  1  0            999 V2000
   15.7708  -19.0508    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1034  -18.5659    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5157  -19.8354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4358  -19.0508    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6908  -19.8354    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0007  -20.5029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0249  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7677  -23.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3104  -23.5044    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5959  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8815  -23.5044    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3388  -21.8544    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5959  -22.2669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3388  -21.0294    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9099  -21.0294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6243  -20.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0532  -19.7917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9262  -18.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3388  -19.3793    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7513  -18.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6243  -19.7917    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9098  -19.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7677  -19.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4178  -19.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0677  -19.3793    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5928  -18.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5928  -20.2043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2427  -18.5542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2427  -20.2043    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5928  -19.3793    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.2427  -19.3793    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.6512  -18.7960    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2058  -20.5029    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3808  -21.3280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0308  -21.3280    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2058  -21.3280    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.2058  -22.1530    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5553  -18.7960    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1686  -19.3480    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8909  -18.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8830  -18.9354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1686  -20.1730    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7115  -18.1284    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5975  -19.3479    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8830  -20.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5975  -20.1729    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3119  -18.9353    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4822  -23.0919    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.9112  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6257  -23.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3402  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0546  -23.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7691  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4836  -23.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1980  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9125  -23.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6270  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3416  -23.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0560  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1968  -23.5044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1968  -24.3294    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.7704  -23.5043    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.4847  -23.0919    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 38  1  1  0  0  0
  2  1  1  0  0  0  0
  3  1  1  0  0  0  0
  4  2  1  0  0  0  0
  5  3  1  0  0  0  0
  3  6  1  6  0  0  0
  4 32  1  1  0  0  0
  5  4  1  0  0  0  0
  5 33  1  6  0  0  0
  9  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8 48  1  0  0  0  0
 10  9  1  0  0  0  0
 13 10  1  0  0  0  0
 10 11  2  0  0  0  0
 12 14  1  0  0  0  0
 13 12  1  0  0  0  0
 16 14  1  0  0  0  0
 16 15  2  0  0  0  0
 16 21  1  0  0  0  0
 19 17  1  0  0  0  0
 17 23  1  0  0  0  0
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 30 24  1  0  0  0  0
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 31 25  1  0  0  0  0
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 31 28  2  0  0  0  0
 31 29  1  0  0  0  0
 33 36  1  0  0  0  0
 36 34  1  0  0  0  0
 36 35  1  0  0  0  0
 36 37  2  0  0  0  0
 39 38  1  0  0  0  0
 40 38  1  0  0  0  0
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 42 39  1  0  0  0  0
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 44 41  1  0  0  0  0
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 47 44  1  0  0  0  0
 46 45  1  0  0  0  0
 48 60  1  0  0  0  0
 60 49  1  0  0  0  0
 49 50  1  0  0  0  0
 50 51  1  0  0  0  0
 51 52  1  0  0  0  0
 52 53  1  0  0  0  0
 53 54  1  0  0  0  0
 54 55  1  0  0  0  0
 55 56  1  0  0  0  0
 56 57  1  0  0  0  0
 57 58  1  0  0  0  0
 58 59  1  0  0  0  0
 60 61  2  0  0  0  0
 59 62  1  0  0  0  0
 62 63  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0033017

> <DATABASE_NAME>
MIME

> <SMILES>
CCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](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/C35H62N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-26(44)63-19-18-37-25(43)16-17-38-33(47)30(46)35(2,3)21-56-62(53,54)59-61(51,52)55-20-24-29(58-60(48,49)50)28(45)34(57-24)42-23-41-27-31(36)39-22-40-32(27)42/h22-24,28-30,34,45-46H,4-21H2,1-3H3,(H,37,43)(H,38,47)(H,51,52)(H,53,54)(H2,36,39,40)(H2,48,49,50)/t24-,28-,29-,30+,34-/m1/s1

> <INCHI_KEY>
DUAFKXOFBZQTQE-QSGBVPJFSA-N

> <FORMULA>
C35H62N7O17P3S

> <MOLECULAR_WEIGHT>
977.89

> <EXACT_MASS>
977.313573819

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
125

> <JCHEM_AVERAGE_POLARIZABILITY>
97.96843974914619

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-[(2-{[2-(tetradecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
1.84

> <JCHEM_LOGP>
-0.29082795114795984

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.9001207347761846

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787813398228

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
363.6299999999999

> <JCHEM_REFRACTIVITY>
227.4459

> <JCHEM_ROTATABLE_BOND_COUNT>
32

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
S-tetradecanoyl-coenzyme A

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-AUG-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:       ChEBI                                       
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-AUG-19         0                                  
HETATM    1  C   UNK     0      29.439 -35.562   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      28.193 -34.656   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      28.963 -37.026   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.947 -35.562   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.423 -37.026   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      29.868 -38.272   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      16.846 -43.105   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.233 -43.875   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      15.513 -43.875   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      14.179 -43.105   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.845 -43.875   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      15.566 -40.795   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.179 -41.565   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      15.566 -39.255   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      12.898 -39.255   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.232 -38.485   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.899 -36.945   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.796 -34.841   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.566 -36.175   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.336 -34.841   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.232 -36.945   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.898 -36.175   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      18.233 -36.175   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      21.313 -36.175   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      24.393 -36.175   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      19.773 -34.634   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      19.773 -37.715   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      22.853 -34.634   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      22.853 -37.715   0.000  0.00  0.00           O+0
HETATM   30  P   UNK     0      19.773 -36.175   0.000  0.00  0.00           P+0
HETATM   31  P   UNK     0      22.853 -36.175   0.000  0.00  0.00           P+0
HETATM   32  C   UNK     0      25.482 -35.086   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      26.517 -38.272   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      24.977 -39.812   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      28.057 -39.812   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      26.517 -39.812   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      26.517 -41.352   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0      30.903 -35.086   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      32.048 -36.116   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      31.530 -33.679   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      33.382 -35.346   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      32.048 -37.656   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      33.061 -33.840   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      34.715 -36.116   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      33.382 -38.426   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      34.715 -37.656   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      36.049 -35.346   0.000  0.00  0.00           N+0
HETATM   48  S   UNK     0      19.567 -43.105   0.000  0.00  0.00           S+0
HETATM   49  C   UNK     0      22.234 -43.105   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      23.568 -43.875   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      24.902 -43.105   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      26.235 -43.875   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      27.569 -43.105   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      28.903 -43.875   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      30.236 -43.105   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      31.570 -43.875   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      32.904 -43.105   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      34.238 -43.875   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      35.571 -43.105   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      20.901 -43.875   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      20.901 -45.415   0.000  0.00  0.00           O+0
HETATM   62  C   UNK     0      36.905 -43.875   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0      38.238 -43.105   0.000  0.00  0.00           C+0
CONECT    1   38    2    3                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5    6                                                  
CONECT    4    2   32    5                                                  
CONECT    5    3    4   33                                                  
CONECT    6    3                                                            
CONECT    7    9    8                                                       
CONECT    8    7   48                                                       
CONECT    9    7   10                                                       
CONECT   10    9   13   11                                                  
CONECT   11   10                                                            
CONECT   12   14   13                                                       
CONECT   13   10   12                                                       
CONECT   14   12   16                                                       
CONECT   15   16                                                            
CONECT   16   14   15   21                                                  
CONECT   17   19   23                                                       
CONECT   18   19                                                            
CONECT   19   17   18   21   20                                             
CONECT   20   19                                                            
CONECT   21   16   19   22                                                  
CONECT   22   21                                                            
CONECT   23   17   30                                                       
CONECT   24   30   31                                                       
CONECT   25   31   32                                                       
CONECT   26   30                                                            
CONECT   27   30                                                            
CONECT   28   31                                                            
CONECT   29   31                                                            
CONECT   30   23   24   26   27                                             
CONECT   31   24   25   28   29                                             
CONECT   32    4   25                                                       
CONECT   33    5   36                                                       
CONECT   34   36                                                            
CONECT   35   36                                                            
CONECT   36   33   34   35   37                                             
CONECT   37   36                                                            
CONECT   38    1   39   40                                                  
CONECT   39   38   41   42                                                  
CONECT   40   38   43                                                       
CONECT   41   39   44   43                                                  
CONECT   42   39   45                                                       
CONECT   43   40   41                                                       
CONECT   44   41   46   47                                                  
CONECT   45   42   46                                                       
CONECT   46   44   45                                                       
CONECT   47   44                                                            
CONECT   48    8   60                                                       
CONECT   49   60   50                                                       
CONECT   50   49   51                                                       
CONECT   51   50   52                                                       
CONECT   52   51   53                                                       
CONECT   53   52   54                                                       
CONECT   54   53   55                                                       
CONECT   55   54   56                                                       
CONECT   56   55   57                                                       
CONECT   57   56   58                                                       
CONECT   58   57   59                                                       
CONECT   59   58   62                                                       
CONECT   60   48   49   61                                                  
CONECT   61   60                                                            
CONECT   62   59   63                                                       
CONECT   63   62                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  130    0
END

Synonyms

Value	Source
N-C14:0-CoA	ChEBI
N-C14:0-coenzyme A	ChEBI
S-Tetradecanoyl-coenzyme A	ChEBI
Tetradecanoyl-CoA	ChEBI
Myristoyl-coenzyme A	MeSH

Molecular Formula

C₃₅H₆₂N₇O₁₇P₃S

Average Mass

977.89

Monoisotopic Mass

977.313573819

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-[(2-{[2-(tetradecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid

Traditional Name

S-tetradecanoyl-coenzyme A

CAS Registry Number

3130-72-1

SMILES

CCCCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@H](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/C35H62N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-26(44)63-19-18-37-25(43)16-17-38-33(47)30(46)35(2,3)21-56-62(53,54)59-61(51,52)55-20-24-29(58-60(48,49)50)28(45)34(57-24)42-23-41-27-31(36)39-22-40-32(27)42/h22-24,28-30,34,45-46H,4-21H2,1-3H3,(H,37,43)(H,38,47)(H,51,52)(H,53,54)(H2,36,39,40)(H2,48,49,50)/t24-,28-,29-,30+,34-/m1/s1

InChI Key

DUAFKXOFBZQTQE-QSGBVPJFSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acyl coas. These are acyl CoAs where the group acylated to the coenzyme A moiety is a 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 fatty acyl 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
Imidolactam
N-acyl-amine
N-substituted imidazole
Organic phosphoric acid derivative
Monosaccharide
Pyrimidine
Alkyl phosphate
Fatty amide
Phosphoric acid ester
Tetrahydrofuran
Imidazole
Azole
Heteroaromatic compound
Carbothioic s-ester
Secondary alcohol
Thiocarboxylic acid ester
Carboxamide group
Secondary carboxylic acid amide
Amino acid or derivatives
Sulfenyl compound
Thiocarboxylic acid or derivatives
Organoheterocyclic compound
Azacycle
Oxacycle
Carboxylic acid derivative
Organosulfur compound
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic nitrogen compound
Primary amine
Organopnictogen compound
Organic oxide
Organooxygen compound
Organonitrogen compound
Alcohol
Amine
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

long-chain fatty acyl-CoA (CHEBI:15532 )
11,12-saturated fatty acyl-CoA (CHEBI:15532 )

Functional Ontology

Not Available

Physical Properties

State

Solid

Predicted Properties

Property	Value	Source
Water Solubility	2.21 g/L	ALOGPS
logP	1.84	ALOGPS
logP	-0.29	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	0.82	ChemAxon
pKa (Strongest Basic)	4.01	ChemAxon
Physiological Charge	-4	ChemAxon
Hydrogen Acceptor Count	17	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	32	ChemAxon
Refractivity	227.45 m³·mol⁻¹	ChemAxon
Polarizability	97.97 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	splash10-000i-1955000202-492920eecd7306497c0f	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-1973200000-1cbb294df62724605b18	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-2931000000-c0fe3c1a0997b03e03c5	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-057i-4951233406-cf208cd5fd7a420f18a6	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0560-2910201001-2f881d14a81696fceb34	2016-09-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-056r-7900100000-e664035807d8a9423b0e	2016-09-12	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-22	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Fibroblasts

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
De Novo Triacylglycerol Biosynthesis TG(a-21:0/i-24:0/14:0)
De Novo Triacylglycerol Biosynthesis TG(a-25:0/10:0/14:0)
De Novo Triacylglycerol Biosynthesis TG(a-25:0/12:0/14:0)
De Novo Triacylglycerol Biosynthesis TG(a-25:0/13:0/14:0)
De Novo Triacylglycerol Biosynthesis TG(a-25:0/14:0/10:0)

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

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

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Eukaryota/Fungi	Ascomycota	1	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 Fibroblasts	Detected but not Quantified						Not Specified	Not Specified	Normal	HMDB	34986597

External Links

HMDB ID

Not Available

DrugBank ID

DB02180

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

C02593

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11966124

PDB ID

Not Available

ChEBI ID

15532

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Hunt MC, Ruiter J, Mooyer P, van Roermond CW, Ofman R, Ijlst L, Wanders RJ: Identification of fatty acid oxidation disorder patients with lowered acyl-CoA thioesterase activity in human skin fibroblasts. Eur J Clin Invest. 2005 Jan;35(1):38-46. doi: 10.1111/j.1365-2362.2005.01447.x. [PubMed:15638818 ]

Showing metabocard for myristoyl-CoA (MMDBc0033017)

MOL for #<Metabolite:0x00007fecd8e93398>

3D MOL for #<Metabolite:0x00007fecd8e93398>

3D SDF for #<Metabolite:0x00007fecd8e93398>

3D-SDF for #<Metabolite:0x00007fecd8e93398>

PDB for #<Metabolite:0x00007fecd8e93398>

3D PDB for #<Metabolite:0x00007fecd8e93398>

SMILES for #<Metabolite:0x00007fecd8e93398>

INCHI for #<Metabolite:0x00007fecd8e93398>

Structure for #<Metabolite:0x00007fecd8e93398>

3D Structure for #<Metabolite:0x00007fecd8e93398>