NP-MRD: Showing NP-Card for myristoyl-CoA (NP0334692)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-10 19:32:57 UTC

Updated at

2024-09-10 19:32:57 UTC

NP-MRD ID

NP0334692

Secondary Accession Numbers

None

Natural Product Identification

Common Name

myristoyl-CoA

Description

Tetradecanoyl-CoA, also known as myristoyl-CoA or N-C14:0CoA, 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. The first pass through the beta-oxidation process starts with the saturated fatty acid palmitoyl-CoA and produces myristoyl-CoA. Tetradecanoyl-CoA is a strong basic compound (based on its pKa). Tetradecanoyl-CoA exists in all living species, ranging from bacteria to humans. In humans, tetradecanoyl-CoA is involved in the metabolic disorder called de novo triacylglycerol biosynthesis pathway. Tetradecanoyl-CoA (or myristoyl-CoA) is an intermediate in fatty acid biosynthesis, fatty acid elongation and the beta oxidation of fatty acids. Outside of the human body, Tetradecanoyl-CoA has been detected, but not quantified in, several different foods, such as jew's ears, hickory nuts, cucumbers, saffrons, and swiss chards. This could make tetradecanoyl-CoA a potential biomarker for the consumption of these foods. Myristoylation also occurs post-translationally, for example when previously internal glycine residues become exposed by caspase cleavage during apoptosis. It is also used in the myristoylation of proteins. Myristoylation is an irreversible, co-translational (during translation) protein modification found in animals, plants, fungi and viruses. It is more common on glycine residues but also occurs on other amino acids. 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. myristoyl-CoA was first documented in 2005 (PMID: 15638818). 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


  Mrv0541 02231219112D          

 63 65  0  0  1  0            999 V2000
   -0.4529    3.4426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7925    2.0085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8912    3.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4488    4.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441    1.2370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4761    2.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8912    4.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6166    3.0192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1700    4.6965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8828    1.2370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5577    0.5704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469    2.0212    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6166    4.6881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3294    3.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3064    0.6457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9185    2.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3294    4.2771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6166    5.5141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1826    0.6499    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0465    1.7317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1197    1.4341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9878    0.6289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1910   -0.1761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3590    1.7150    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3590   -0.0293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3547    2.5496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1894    1.7317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3547   -1.7066    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4994   -1.6900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3715   -2.6837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1851   -1.6941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7866   -1.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0736   -1.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9666   -1.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0569   -2.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0569   -0.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2496   -1.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9666   -0.4068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5368   -1.2286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2496   -2.4657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1761   -1.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889   -1.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6061   -1.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3189   -1.2286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6061   -2.4657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0317   -1.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7446   -1.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4617   -1.6396    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1746   -1.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8874   -1.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1746   -0.4025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6002   -1.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3131   -1.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0259   -1.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7387   -1.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7387   -2.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0259   -2.8725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3088   -2.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5834   -2.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8831   -2.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1578   -2.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4574   -2.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7278   -2.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  6  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8 14  2  0  0  0  0
 10 15  1  6  0  0  0
 12 16  1  1  0  0  0
 13 17  2  0  0  0  0
 13 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  2  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 34 37  1  0  0  0  0
 34 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  2  0  0  0  0
 50 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
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
  7  9  1  0  0  0  0
 10 12  1  0  0  0  0
 14 17  1  0  0  0  0
M  END


  Mrv0541 02231219112D          

 63 65  0  0  1  0            999 V2000
   -0.4529    3.4426    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7925    2.0085    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8912    3.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4488    4.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0441    1.2370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.4761    2.5034    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8912    4.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6166    3.0192    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1700    4.6965    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8828    1.2370    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.5577    0.5704    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1469    2.0212    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6166    4.6881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3294    3.4426    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3064    0.6457    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9185    2.2644    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3294    4.2771    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6166    5.5141    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1826    0.6499    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0465    1.7317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1197    1.4341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9878    0.6289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1910   -0.1761    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3590    1.7150    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3590   -0.0293    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3547    2.5496    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1894    1.7317    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3547   -1.7066    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4994   -1.6900    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3715   -2.6837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1851   -1.6941    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7866   -1.2789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0736   -1.6941    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9666   -1.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0569   -2.4866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0569   -0.8680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2496   -1.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9666   -0.4068    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5368   -1.2286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2496   -2.4657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1761   -1.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8889   -1.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6061   -1.6438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3189   -1.2286    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6061   -2.4657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0317   -1.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7446   -1.2328    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4617   -1.6396    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.1746   -1.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8874   -1.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1746   -0.4025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6002   -1.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3131   -1.6396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0259   -1.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7387   -1.6354    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7387   -2.4573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0259   -2.8725    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3088   -2.4614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5834   -2.8514    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8831   -2.4153    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1578   -2.8053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4574   -2.3692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7278   -2.7592    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  1  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  2  6  1  0  0  0  0
  3  7  2  0  0  0  0
  3  8  1  0  0  0  0
  4  9  2  0  0  0  0
  5 10  1  0  0  0  0
  5 11  1  6  0  0  0
  6 12  1  0  0  0  0
  7 13  1  0  0  0  0
  8 14  2  0  0  0  0
 10 15  1  6  0  0  0
 12 16  1  1  0  0  0
 13 17  2  0  0  0  0
 13 18  1  0  0  0  0
 15 19  1  0  0  0  0
 16 20  1  0  0  0  0
 19 21  1  0  0  0  0
 19 22  1  0  0  0  0
 19 23  2  0  0  0  0
 20 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 24 27  2  0  0  0  0
 25 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 28 31  2  0  0  0  0
 29 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
 34 37  1  0  0  0  0
 34 38  1  0  0  0  0
 37 39  1  0  0  0  0
 37 40  2  0  0  0  0
 39 41  1  0  0  0  0
 41 42  1  0  0  0  0
 42 43  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 44 46  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  1  0  0  0  0
 48 49  1  0  0  0  0
 49 50  1  0  0  0  0
 49 51  2  0  0  0  0
 50 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
 59 60  1  0  0  0  0
 60 61  1  0  0  0  0
 61 62  1  0  0  0  0
 62 63  1  0  0  0  0
  7  9  1  0  0  0  0
 10 12  1  0  0  0  0
 14 17  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0334692

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCCCCCCCCCC(=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/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-XVDJLSDJSA-N

> <FORMULA>
C35H62N7O17P3S

> <MOLECULAR_WEIGHT>
977.89

> <EXACT_MASS>
977.313573819

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_AVERAGE_POLARIZABILITY>
96.43111318115857

> <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({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>
-1.384419707966352

> <ALOGPS_LOGS>
-2.65

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.8334045176178444

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8252479627216065

> <JCHEM_PKA_STRONGEST_BASIC>
4.946047024039826

> <JCHEM_POLAR_SURFACE_AREA>
363.6299999999999

> <JCHEM_REFRACTIVITY>
227.44590000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
32

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.21e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-[({hydroxy[hydroxy(3-hydroxy-2,2-dimethyl-3-[(2-{[2-(tetradecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]propoxy)phosphoryl]oxyphosphoryl}oxy)methyl]oxolan-3-yl]oxyphosphonic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  N   UNK     0      -0.845   6.426   0.000  0.00  0.00           N+0
HETATM    2  C   UNK     0      -1.479   3.749   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.530   6.426   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.838   7.984   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.949   2.309   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -2.755   4.673   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -3.530   7.984   0.000  0.00  0.00           C+0
HETATM    8  N   UNK     0      -4.884   5.636   0.000  0.00  0.00           N+0
HETATM    9  N   UNK     0      -2.184   8.767   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      -3.515   2.309   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.041   1.065   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.008   3.773   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -4.884   8.751   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -6.215   6.426   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.305   1.205   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.448   4.227   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      -6.215   7.984   0.000  0.00  0.00           N+0
HETATM   18  N   UNK     0      -4.884  10.293   0.000  0.00  0.00           N+0
HETATM   19  P   UNK     0      -5.941   1.213   0.000  0.00  0.00           P+0
HETATM   20  O   UNK     0      -7.554   3.233   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -5.823   2.677   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      -7.444   1.174   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      -5.957  -0.329   0.000  0.00  0.00           O+0
HETATM   24  P   UNK     0     -10.004   3.201   0.000  0.00  0.00           P+0
HETATM   25  O   UNK     0     -10.004  -0.055   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      -9.996   4.759   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0     -11.553   3.233   0.000  0.00  0.00           O+0
HETATM   28  P   UNK     0      -9.996  -3.186   0.000  0.00  0.00           P+0
HETATM   29  O   UNK     0      -8.399  -3.155   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0     -10.027  -5.010   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0     -11.545  -3.162   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -7.068  -2.387   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.737  -3.162   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -3.671  -2.293   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -5.706  -4.642   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -5.706  -1.620   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -2.333  -3.068   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.671  -0.759   0.000  0.00  0.00           O+0
HETATM   39  N   UNK     0      -1.002  -2.293   0.000  0.00  0.00           N+0
HETATM   40  O   UNK     0      -2.333  -4.603   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       0.329  -3.068   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.659  -2.293   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       2.998  -3.068   0.000  0.00  0.00           C+0
HETATM   44  N   UNK     0       4.329  -2.293   0.000  0.00  0.00           N+0
HETATM   45  O   UNK     0       2.998  -4.603   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       5.659  -3.061   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       6.990  -2.301   0.000  0.00  0.00           C+0
HETATM   48  S   UNK     0       8.329  -3.061   0.000  0.00  0.00           S+0
HETATM   49  C   UNK     0       9.659  -2.293   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      10.990  -3.061   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       9.659  -0.751   0.000  0.00  0.00           O+0
HETATM   52  C   UNK     0      12.320  -2.293   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      13.651  -3.061   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      14.982  -2.293   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      16.312  -3.053   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      16.312  -4.587   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      14.982  -5.362   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      13.643  -4.595   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      12.289  -5.323   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      10.982  -4.509   0.000  0.00  0.00           C+0
HETATM   61  C   UNK     0       9.628  -5.236   0.000  0.00  0.00           C+0
HETATM   62  C   UNK     0       8.321  -4.422   0.000  0.00  0.00           C+0
HETATM   63  C   UNK     0       6.959  -5.150   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1    9                                                       
CONECT    5    2   10   11                                                  
CONECT    6    2   12                                                       
CONECT    7    3   13    9                                                  
CONECT    8    3   14                                                       
CONECT    9    4    7                                                       
CONECT   10    5   15   12                                                  
CONECT   11    5                                                            
CONECT   12    6   16   10                                                  
CONECT   13    7   17   18                                                  
CONECT   14    8   17                                                       
CONECT   15   10   19                                                       
CONECT   16   12   20                                                       
CONECT   17   13   14                                                       
CONECT   18   13                                                            
CONECT   19   15   21   22   23                                             
CONECT   20   16   24                                                       
CONECT   21   19                                                            
CONECT   22   19                                                            
CONECT   23   19                                                            
CONECT   24   20   25   26   27                                             
CONECT   25   24   28                                                       
CONECT   26   24                                                            
CONECT   27   24                                                            
CONECT   28   25   29   30   31                                             
CONECT   29   28   32                                                       
CONECT   30   28                                                            
CONECT   31   28                                                            
CONECT   32   29   33                                                       
CONECT   33   32   34   35   36                                             
CONECT   34   33   37   38                                                  
CONECT   35   33                                                            
CONECT   36   33                                                            
CONECT   37   34   39   40                                                  
CONECT   38   34                                                            
CONECT   39   37   41                                                       
CONECT   40   37                                                            
CONECT   41   39   42                                                       
CONECT   42   41   43                                                       
CONECT   43   42   44   45                                                  
CONECT   44   43   46                                                       
CONECT   45   43                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48                                                       
CONECT   48   47   49                                                       
CONECT   49   48   50   51                                                  
CONECT   50   49   52                                                       
CONECT   51   49                                                            
CONECT   52   50   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   60                                                       
CONECT   60   59   61                                                       
CONECT   61   60   62                                                       
CONECT   62   61   63                                                       
CONECT   63   62                                                            
MASTER        0    0    0    0    0    0    0    0   63    0  130    0
END

View in JSmol

Synonyms

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

Chemical Formula

C₃₅H₆₂N₇O₁₇P₃S

Average Mass

977.8900 Da

Monoisotopic Mass

977.31357 Da

IUPAC Name

{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy({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

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

CAS Registry Number

Not Available

SMILES

CCCCCCCCCCCCCC(=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/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-XVDJLSDJSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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

Fatty acyl CoAs (C02593 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.84	ALOGPS
logP	-1.4	ChemAxon
logS	-2.6	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	9	ChemAxon
Polar Surface Area	363.63 Å²	ChemAxon
Rotatable Bond Count	32	ChemAxon
Refractivity	227.45 m³·mol⁻¹	ChemAxon
Polarizability	96.43 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

External Links

HMDB ID

HMDB0001521

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB031010

KNApSAcK ID

Not Available

Chemspider ID

58623

KEGG Compound ID

C02593

BioCyc ID

Not Available

BiGG ID

40154

Wikipedia Link

Not Available

METLIN ID

3707

PubChem Compound

65113

PDB ID

Not Available

ChEBI ID

15532

Good Scents ID

Not Available

References

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 NP-Card for myristoyl-CoA (NP0334692)

MOL for NP0334692 (myristoyl-CoA)

3D MOL for NP0334692 (myristoyl-CoA)

3D SDF for NP0334692 (myristoyl-CoA)

3D-SDF for NP0334692 (myristoyl-CoA)

PDB for NP0334692 (myristoyl-CoA)

3D PDB for NP0334692 (myristoyl-CoA)

SMILES for NP0334692 (myristoyl-CoA)

INCHI for NP0334692 (myristoyl-CoA)

Structure for NP0334692 (myristoyl-CoA)

3D Structure for NP0334692 (myristoyl-CoA)