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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (111)transporters (1) Show 112 proteins XML

enzymes (111)transporters (1) Show 112 proteins

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2006-08-13 00:43:18 UTC

Update Date

2021-09-14 15:43:08 UTC

HMDB ID

HMDB0003571

Secondary Accession Numbers

HMDB03571

Metabolite Identification

Common Name

Lauroyl-CoA

Description

Lauroyl-CoA, also known as dodecanoyl-CoA or C12:0-CoA, belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. Thus, lauroyl-CoA is considered to be a fatty ester lipid molecule. A medium-chain fatty acyl-CoA that results from the formal condensation of the thiol group of coenzyme A with the carboxy group of lauric (dodecanoic) acid. Lauroyl-CoA is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Lauroyl-CoA exists in all living species, ranging from bacteria to humans. In humans, lauroyl-CoA is involved in the metabolic disorder called the mitochondrial beta-oxidation of long chain saturated fatty acids pathway. Outside of the human body, Lauroyl-CoA has been detected, but not quantified in, several different foods, such as oval-leaf huckleberries, guava, bamboo shoots, red bell peppers, and calabash. This could make lauroyl-CoA a potential biomarker for the consumption of these foods.

Structure

MOL SDF 3D SDF PDB 3D PDB SMILES InChI

ChEBI
  Mrv1652308111919252D          

 61 63  0  0  1  0            999 V2000
   15.7725  -19.0538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1051  -18.5689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5175  -19.8384    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4376  -19.0538    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6926  -19.8384    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0025  -20.5059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0268  -23.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7696  -23.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3123  -23.5073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5978  -23.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8834  -23.5073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3407  -21.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5978  -22.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3407  -21.0323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9118  -21.0323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6262  -20.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0551  -19.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9282  -18.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3407  -19.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7532  -18.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6262  -19.7947    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9117  -19.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7696  -19.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4196  -19.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0696  -19.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5946  -18.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5946  -20.2072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2446  -18.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2446  -20.2072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5946  -19.3822    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.2446  -19.3822    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.6530  -18.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2076  -20.5059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3826  -21.3309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0326  -21.3309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2076  -21.3309    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.2076  -22.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5570  -18.7989    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1703  -19.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8927  -18.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8847  -18.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1703  -20.1759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7132  -18.1314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5992  -19.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8847  -20.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5992  -20.1758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3136  -18.9383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4841  -23.0948    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.9130  -23.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6275  -23.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3420  -23.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0564  -23.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7709  -23.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4854  -23.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1998  -23.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9143  -23.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6287  -23.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3433  -23.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0577  -23.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1986  -23.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1986  -24.3323    0.0000 O   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
M  END

ChEBI
  Mrv1652308111919252D          

 61 63  0  0  1  0            999 V2000
   15.7725  -19.0538    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   15.1051  -18.5689    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.5175  -19.8384    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.4376  -19.0538    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   14.6926  -19.8384    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   16.0025  -20.5059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.0268  -23.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7696  -23.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3123  -23.5073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5978  -23.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8834  -23.5073    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3407  -21.8573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5978  -22.2698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3407  -21.0323    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.9118  -21.0323    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.6262  -20.6197    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0551  -19.7947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9282  -18.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3407  -19.3822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7532  -18.6678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6262  -19.7947    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    6.9117  -19.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.7696  -19.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4196  -19.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.0696  -19.3822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5946  -18.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5946  -20.2072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2446  -18.5572    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.2446  -20.2072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.5946  -19.3822    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   12.2446  -19.3822    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   13.6530  -18.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2076  -20.5059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   13.3826  -21.3309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.0326  -21.3309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.2076  -21.3309    0.0000 P   0  0  0  0  0  0  0  0  0  0  0  0
   14.2076  -22.1559    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.5570  -18.7989    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.1703  -19.3509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8927  -18.0452    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8847  -18.9384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1703  -20.1759    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7132  -18.1314    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.5992  -19.3508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8847  -20.5883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5992  -20.1758    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   19.3136  -18.9383    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.4841  -23.0948    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   11.9130  -23.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6275  -23.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3420  -23.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0564  -23.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7709  -23.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4854  -23.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.1998  -23.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9143  -23.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6287  -23.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3433  -23.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0577  -23.0948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1986  -23.5073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1986  -24.3323    0.0000 O   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
M  END
> <DATABASE_ID>
HMDB0003571

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCCCCCC(=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/C33H58N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-24(42)61-17-16-35-23(41)14-15-36-31(45)28(44)33(2,3)19-54-60(51,52)57-59(49,50)53-18-22-27(56-58(46,47)48)26(43)32(55-22)40-21-39-25-29(34)37-20-38-30(25)40/h20-22,26-28,32,43-44H,4-19H2,1-3H3,(H,35,41)(H,36,45)(H,49,50)(H,51,52)(H2,34,37,38)(H2,46,47,48)/t22-,26-,27-,28+,32-/m1/s1

> <INCHI_KEY>
YMCXGHLSVALICC-GMHMEAMDSA-N

> <FORMULA>
C33H58N7O17P3S

> <MOLECULAR_WEIGHT>
949.837

> <EXACT_MASS>
949.282273691

> <JCHEM_ACCEPTOR_COUNT>
17

> <JCHEM_ATOM_COUNT>
119

> <JCHEM_AVERAGE_POLARIZABILITY>
91.94081506274604

> <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)-2-({[({[(3R)-3-[(2-{[2-(dodecanoylsulfanyl)ethyl]carbamoyl}ethyl)carbamoyl]-3-hydroxy-2,2-dimethylpropoxy](hydroxy)phosphoryl}oxy)(hydroxy)phosphoryl]oxy}methyl)-4-hydroxyoxolan-3-yl]oxy}phosphonic acid

> <ALOGPS_LOGP>
1.35

> <JCHEM_LOGP>
-1.1799652811479617

> <ALOGPS_LOGS>
-2.56

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-4

> <JCHEM_PKA>
1.900120734776185

> <JCHEM_PKA_STRONGEST_ACIDIC>
0.8209787813398224

> <JCHEM_PKA_STRONGEST_BASIC>
4.006053268556904

> <JCHEM_POLAR_SURFACE_AREA>
363.6299999999999

> <JCHEM_REFRACTIVITY>
218.24390000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
30

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
lauroyl-coa

> <JCHEM_VEBER_RULE>
0

$$$$

https://cactus.nci.nih.gov/chemical/structure/CCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:118})
119121  0  0  0  0  0  0  0  0999 V2000
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M  END
$$$$

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      29.442 -35.567   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      28.196 -34.662   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      28.966 -37.032   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.950 -35.567   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      27.426 -37.032   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      29.871 -38.278   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      16.850 -43.110   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.237 -43.880   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0      15.516 -43.880   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0      14.183 -43.110   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      12.849 -43.880   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      15.569 -40.800   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      14.183 -41.570   0.000  0.00  0.00           C+0
HETATM   14  N   UNK     0      15.569 -39.260   0.000  0.00  0.00           N+0
HETATM   15  O   UNK     0      12.902 -39.260   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      14.236 -38.490   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      16.903 -36.950   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.799 -34.847   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      15.569 -36.180   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      16.339 -34.847   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      14.236 -36.950   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0      12.902 -36.180   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0      18.237 -36.180   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      21.317 -36.180   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      24.397 -36.180   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0      19.777 -34.640   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0      19.777 -37.720   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0      22.857 -34.640   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      22.857 -37.720   0.000  0.00  0.00           O+0
HETATM   30  P   UNK     0      19.777 -36.180   0.000  0.00  0.00           P+0
HETATM   31  P   UNK     0      22.857 -36.180   0.000  0.00  0.00           P+0
HETATM   32  C   UNK     0      25.486 -35.091   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      26.521 -38.278   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      24.981 -39.818   0.000  0.00  0.00           O+0
HETATM   35  O   UNK     0      28.061 -39.818   0.000  0.00  0.00           O+0
HETATM   36  P   UNK     0      26.521 -39.818   0.000  0.00  0.00           P+0
HETATM   37  O   UNK     0      26.521 -41.358   0.000  0.00  0.00           O+0
HETATM   38  N   UNK     0      30.906 -35.091   0.000  0.00  0.00           N+0
HETATM   39  C   UNK     0      32.051 -36.122   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      31.533 -33.684   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      33.385 -35.352   0.000  0.00  0.00           C+0
HETATM   42  N   UNK     0      32.051 -37.662   0.000  0.00  0.00           N+0
HETATM   43  N   UNK     0      33.065 -33.845   0.000  0.00  0.00           N+0
HETATM   44  C   UNK     0      34.719 -36.121   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0      33.385 -38.431   0.000  0.00  0.00           C+0
HETATM   46  N   UNK     0      34.719 -37.661   0.000  0.00  0.00           N+0
HETATM   47  N   UNK     0      36.052 -35.351   0.000  0.00  0.00           N+0
HETATM   48  S   UNK     0      19.570 -43.110   0.000  0.00  0.00           S+0
HETATM   49  C   UNK     0      22.238 -43.110   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      23.571 -43.880   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0      24.905 -43.110   0.000  0.00  0.00           C+0
HETATM   52  C   UNK     0      26.239 -43.880   0.000  0.00  0.00           C+0
HETATM   53  C   UNK     0      27.572 -43.110   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0      28.906 -43.880   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      30.240 -43.110   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      31.573 -43.880   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0      32.907 -43.110   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0      34.241 -43.880   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0      35.574 -43.110   0.000  0.00  0.00           C+0
HETATM   60  C   UNK     0      20.904 -43.880   0.000  0.00  0.00           C+0
HETATM   61  O   UNK     0      20.904 -45.420   0.000  0.00  0.00           O+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                                                            
CONECT   60   48   49   61                                                  
CONECT   61   60                                                            
MASTER        0    0    0    0    0    0    0    0   61    0  126    0
END

COMPND    https://cactus.nci.nih.gov/chemical/structure/CCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=... 
AUTHOR    GENERATED BY OPEN BABEL 3.1.0
HETATM    1  C   UNL     1      24.278  -4.840   1.489  1.00  0.00           C  
HETATM    2  C   UNL     1      22.961  -4.272   2.021  1.00  0.00           C  
HETATM    3  C   UNL     1      22.047  -3.916   0.847  1.00  0.00           C  
HETATM    4  C   UNL     1      20.730  -3.348   1.380  1.00  0.00           C  
HETATM    5  C   UNL     1      19.817  -2.991   0.205  1.00  0.00           C  
HETATM    6  C   UNL     1      18.500  -2.423   0.738  1.00  0.00           C  
HETATM    7  C   UNL     1      17.586  -2.066  -0.437  1.00  0.00           C  
HETATM    8  C   UNL     1      16.269  -1.498   0.096  1.00  0.00           C  
HETATM    9  C   UNL     1      15.356  -1.141  -1.078  1.00  0.00           C  
HETATM   10  C   UNL     1      14.039  -0.574  -0.546  1.00  0.00           C  
HETATM   11  C   UNL     1      13.125  -0.217  -1.720  1.00  0.00           C  
HETATM   12  C   UNL     1      11.828   0.343  -1.196  1.00  0.00           C  
HETATM   13  O   UNL     1      11.651   0.445   0.000  1.00  0.00           O  
HETATM   14  S   UNL     1      10.603   0.833  -2.287  1.00  0.00           S  
HETATM   15  C   UNL     1       9.343   1.392  -1.115  1.00  0.00           C  
HETATM   16  C   UNL     1       8.117   1.890  -1.883  1.00  0.00           C  
HETATM   17  N   UNL     1       7.096   2.342  -0.934  1.00  0.00           N  
HETATM   18  C   UNL     1       5.923   2.826  -1.387  1.00  0.00           C  
HETATM   19  O   UNL     1       5.711   2.887  -2.580  1.00  0.00           O  
HETATM   20  C   UNL     1       4.873   3.292  -0.411  1.00  0.00           C  
HETATM   21  C   UNL     1       3.647   3.790  -1.179  1.00  0.00           C  
HETATM   22  N   UNL     1       2.627   4.243  -0.230  1.00  0.00           N  
HETATM   23  C   UNL     1       1.453   4.726  -0.683  1.00  0.00           C  
HETATM   24  O   UNL     1       1.277   4.874  -1.874  1.00  0.00           O  
HETATM   25  C   UNL     1       0.360   5.084   0.291  1.00  0.00           C  
HETATM   26  H   UNL     1      -0.029   6.074   0.053  1.00  0.00           H  
HETATM   27  O   UNL     1       0.887   5.086   1.619  1.00  0.00           O  
HETATM   28  C   UNL     1      -0.768   4.054   0.191  1.00  0.00           C  
HETATM   29  C   UNL     1      -1.430   4.155  -1.184  1.00  0.00           C  
HETATM   30  C   UNL     1      -0.193   2.649   0.379  1.00  0.00           C  
HETATM   31  C   UNL     1      -1.807   4.330   1.280  1.00  0.00           C  
HETATM   32  O   UNL     1      -2.860   3.369   1.187  1.00  0.00           O  
HETATM   33  P   UNL     1      -4.128   3.358   2.180  1.00  0.00           P  
HETATM   34  O   UNL     1      -3.633   3.037   3.678  1.00  0.00           O  
HETATM   35  O   UNL     1      -4.788   4.683   2.151  1.00  0.00           O  
HETATM   36  O   UNL     1      -5.172   2.228   1.705  1.00  0.00           O  
HETATM   37  P   UNL     1      -6.739   1.971   1.970  1.00  0.00           P  
HETATM   38  O   UNL     1      -6.945   1.406   3.464  1.00  0.00           O  
HETATM   39  O   UNL     1      -7.480   3.243   1.818  1.00  0.00           O  
HETATM   40  O   UNL     1      -7.293   0.896   0.908  1.00  0.00           O  
HETATM   41  C   UNL     1      -8.672   0.533   0.816  1.00  0.00           C  
HETATM   42  C   UNL     1      -8.853  -0.508  -0.291  1.00  0.00           C  
HETATM   43  H   UNL     1      -8.433  -0.133  -1.224  1.00  0.00           H  
HETATM   44  O   UNL     1      -8.202  -1.734   0.080  1.00  0.00           O  
HETATM   45  C   UNL     1      -8.994  -2.813  -0.462  1.00  0.00           C  
HETATM   46  H   UNL     1      -8.800  -2.934  -1.528  1.00  0.00           H  
HETATM   47  C   UNL     1     -10.453  -2.345  -0.223  1.00  0.00           C  
HETATM   48  H   UNL     1     -10.764  -2.550   0.801  1.00  0.00           H  
HETATM   49  O   UNL     1     -11.344  -2.959  -1.156  1.00  0.00           O  
HETATM   50  C   UNL     1     -10.351  -0.819  -0.479  1.00  0.00           C  
HETATM   51  H   UNL     1     -10.948  -0.270   0.249  1.00  0.00           H  
HETATM   52  O   UNL     1     -10.771  -0.505  -1.808  1.00  0.00           O  
HETATM   53  P   UNL     1     -11.983   0.505  -2.129  1.00  0.00           P  
HETATM   54  O   UNL     1     -11.591   1.987  -1.638  1.00  0.00           O  
HETATM   55  O   UNL     1     -12.264   0.520  -3.714  1.00  0.00           O  
HETATM   56  O   UNL     1     -13.201   0.056  -1.417  1.00  0.00           O  
HETATM   57  N   UNL     1      -8.725  -4.061   0.255  1.00  0.00           N  
HETATM   58  C   UNL     1      -8.239  -4.174   1.524  1.00  0.00           C  
HETATM   59  N   UNL     1      -8.122  -5.430   1.845  1.00  0.00           N  
HETATM   60  C   UNL     1      -8.525  -6.200   0.806  1.00  0.00           C  
HETATM   61  C   UNL     1      -8.922  -5.332  -0.224  1.00  0.00           C  
HETATM   62  N   UNL     1      -9.366  -5.845  -1.367  1.00  0.00           N  
HETATM   63  C   UNL     1      -9.433  -7.149  -1.535  1.00  0.00           C  
HETATM   64  N   UNL     1      -9.072  -8.005  -0.596  1.00  0.00           N  
HETATM   65  C   UNL     1      -8.620  -7.585   0.581  1.00  0.00           C  
HETATM   66  N   UNL     1      -8.243  -8.489   1.558  1.00  0.00           N  
HETATM   67  H   UNL     1      24.076  -5.735   0.900  1.00  0.00           H  
HETATM   68  H   UNL     1      24.767  -4.095   0.861  1.00  0.00           H  
HETATM   69  H   UNL     1      24.929  -5.095   2.325  1.00  0.00           H  
HETATM   70  H   UNL     1      22.471  -5.017   2.649  1.00  0.00           H  
HETATM   71  H   UNL     1      23.163  -3.377   2.610  1.00  0.00           H  
HETATM   72  H   UNL     1      22.537  -3.171   0.219  1.00  0.00           H  
HETATM   73  H   UNL     1      21.846  -4.811   0.258  1.00  0.00           H  
HETATM   74  H   UNL     1      20.241  -4.093   2.007  1.00  0.00           H  
HETATM   75  H   UNL     1      20.932  -2.453   1.968  1.00  0.00           H  
HETATM   76  H   UNL     1      20.306  -2.246  -0.422  1.00  0.00           H  
HETATM   77  H   UNL     1      19.615  -3.886  -0.383  1.00  0.00           H  
HETATM   78  H   UNL     1      18.010  -3.168   1.365  1.00  0.00           H  
HETATM   79  H   UNL     1      18.701  -1.528   1.326  1.00  0.00           H  
HETATM   80  H   UNL     1      18.076  -1.321  -1.064  1.00  0.00           H  
HETATM   81  H   UNL     1      17.385  -2.961  -1.025  1.00  0.00           H  
HETATM   82  H   UNL     1      15.780  -2.243   0.724  1.00  0.00           H  
HETATM   83  H   UNL     1      16.471  -0.603   0.685  1.00  0.00           H  
HETATM   84  H   UNL     1      15.845  -0.397  -1.706  1.00  0.00           H  
HETATM   85  H   UNL     1      15.154  -2.036  -1.667  1.00  0.00           H  
HETATM   86  H   UNL     1      13.549  -1.319   0.082  1.00  0.00           H  
HETATM   87  H   UNL     1      14.240   0.321   0.043  1.00  0.00           H  
HETATM   88  H   UNL     1      13.614   0.528  -2.348  1.00  0.00           H  
HETATM   89  H   UNL     1      12.923  -1.112  -2.309  1.00  0.00           H  
HETATM   90  H   UNL     1       9.054   0.563  -0.469  1.00  0.00           H  
HETATM   91  H   UNL     1       9.745   2.203  -0.508  1.00  0.00           H  
HETATM   92  H   UNL     1       8.405   2.719  -2.529  1.00  0.00           H  
HETATM   93  H   UNL     1       7.714   1.079  -2.490  1.00  0.00           H  
HETATM   94  H   UNL     1       7.266   2.294   0.020  1.00  0.00           H  
HETATM   95  H   UNL     1       4.585   2.463   0.235  1.00  0.00           H  
HETATM   96  H   UNL     1       5.276   4.103   0.196  1.00  0.00           H  
HETATM   97  H   UNL     1       3.936   4.619  -1.825  1.00  0.00           H  
HETATM   98  H   UNL     1       3.245   2.979  -1.786  1.00  0.00           H  
HETATM   99  H   UNL     1       2.796   4.194   0.724  1.00  0.00           H  
HETATM  100  H   UNL     1       1.252   4.235   1.899  1.00  0.00           H  
HETATM  101  H   UNL     1      -0.710   3.883  -1.955  1.00  0.00           H  
HETATM  102  H   UNL     1      -2.283   3.477  -1.227  1.00  0.00           H  
HETATM  103  H   UNL     1      -1.770   5.177  -1.349  1.00  0.00           H  
HETATM  104  H   UNL     1       0.279   2.577   1.359  1.00  0.00           H  
HETATM  105  H   UNL     1      -0.997   1.916   0.308  1.00  0.00           H  
HETATM  106  H   UNL     1       0.547   2.452  -0.396  1.00  0.00           H  
HETATM  107  H   UNL     1      -1.335   4.258   2.260  1.00  0.00           H  
HETATM  108  H   UNL     1      -2.216   5.332   1.146  1.00  0.00           H  
HETATM  109  H   UNL     1      -3.191   2.183   3.771  1.00  0.00           H  
HETATM  110  H   UNL     1      -6.486   0.572   3.635  1.00  0.00           H  
HETATM  111  H   UNL     1      -9.002   0.113   1.766  1.00  0.00           H  
HETATM  112  H   UNL     1      -9.266   1.417   0.584  1.00  0.00           H  
HETATM  113  H   UNL     1     -11.373  -3.924  -1.096  1.00  0.00           H  
HETATM  114  H   UNL     1     -10.801   2.346  -2.064  1.00  0.00           H  
HETATM  115  H   UNL     1     -12.983   1.109  -3.980  1.00  0.00           H  
HETATM  116  H   UNL     1      -7.987  -3.344   2.167  1.00  0.00           H  
HETATM  117  H   UNL     1      -9.799  -7.533  -2.476  1.00  0.00           H  
HETATM  118  H   UNL     1      -8.307  -9.441   1.388  1.00  0.00           H  
HETATM  119  H   UNL     1      -7.915  -8.170   2.413  1.00  0.00           H  
CONECT    1    2   67   68   69                                       
CONECT    2    1    3   70   71                                       
CONECT    3    2    4   72   73                                       
CONECT    4    3    5   74   75                                       
CONECT    5    4    6   76   77                                       
CONECT    6    5    7   78   79                                       
CONECT    7    6    8   80   81                                       
CONECT    8    7    9   82   83                                       
CONECT    9    8   10   84   85                                       
CONECT   10    9   11   86   87                                       
CONECT   11   10   12   88   89                                       
CONECT   12   11   13   13   14                                       
CONECT   13   12   12                                                 
CONECT   14   12   15                                                 
CONECT   15   14   16   90   91                                       
CONECT   16   15   17   92   93                                       
CONECT   17   16   18   94                                            
CONECT   18   17   19   19   20                                       
CONECT   19   18   18                                                 
CONECT   20   18   21   95   96                                       
CONECT   21   20   22   97   98                                       
CONECT   22   21   23   99                                            
CONECT   23   22   24   24   25                                       
CONECT   24   23   23                                                 
CONECT   25   23   26   27   28                                       
CONECT   26   25                                                      
CONECT   27   25  100                                                 
CONECT   28   25   29   30   31                                       
CONECT   29   28  101  102  103                                       
CONECT   30   28  104  105  106                                       
CONECT   31   28   32  107  108                                       
CONECT   32   31   33                                                 
CONECT   33   32   34   35   35                                       
CONECT   33   36                                                      
CONECT   34   33  109                                                 
CONECT   35   33   33                                                 
CONECT   36   33   37                                                 
CONECT   37   36   38   39   39                                       
CONECT   37   40                                                      
CONECT   38   37  110                                                 
CONECT   39   37   37                                                 
CONECT   40   37   41                                                 
CONECT   41   40   42  111  112                                       
CONECT   42   41   43   44   50                                       
CONECT   43   42                                                      
CONECT   44   42   45                                                 
CONECT   45   44   46   47   57                                       
CONECT   46   45                                                      
CONECT   47   45   48   49   50                                       
CONECT   48   47                                                      
CONECT   49   47  113                                                 
CONECT   50   47   51   42   52                                       
CONECT   51   50                                                      
CONECT   52   50   53                                                 
CONECT   53   52   54   55   56                                       
CONECT   53   56                                                      
CONECT   54   53  114                                                 
CONECT   55   53  115                                                 
CONECT   56   53   53                                                 
CONECT   57   45   58   61                                            
CONECT   58   57   59   59  116                                       
CONECT   59   58   58   60                                            
CONECT   60   59   61   61   65                                       
CONECT   61   60   60   57   62                                       
CONECT   62   61   63   63                                            
CONECT   63   62   62   64  117                                       
CONECT   64   63   65   65                                            
CONECT   65   64   64   60   66                                       
CONECT   66   65  118  119                                            
CONECT   67    1                                                      
CONECT   68    1                                                      
CONECT   69    1                                                      
CONECT   70    2                                                      
CONECT   71    2                                                      
CONECT   72    3                                                      
CONECT   73    3                                                      
CONECT   74    4                                                      
CONECT   75    4                                                      
CONECT   76    5                                                      
CONECT   77    5                                                      
CONECT   78    6                                                      
CONECT   79    6                                                      
CONECT   80    7                                                      
CONECT   81    7                                                      
CONECT   82    8                                                      
CONECT   83    8                                                      
CONECT   84    9                                                      
CONECT   85    9                                                      
CONECT   86   10                                                      
CONECT   87   10                                                      
CONECT   88   11                                                      
CONECT   89   11                                                      
CONECT   90   15                                                      
CONECT   91   15                                                      
CONECT   92   16                                                      
CONECT   93   16                                                      
CONECT   94   17                                                      
CONECT   95   20                                                      
CONECT   96   20                                                      
CONECT   97   21                                                      
CONECT   98   21                                                      
CONECT   99   22                                                      
CONECT  100   27                                                      
CONECT  101   29                                                      
CONECT  102   29                                                      
CONECT  103   29                                                      
CONECT  104   30                                                      
CONECT  105   30                                                      
CONECT  106   30                                                      
CONECT  107   31                                                      
CONECT  108   31                                                      
CONECT  109   34                                                      
CONECT  110   38                                                      
CONECT  111   41                                                      
CONECT  112   41                                                      
CONECT  113   49                                                      
CONECT  114   54                                                      
CONECT  115   55                                                      
CONECT  116   58                                                      
CONECT  117   63                                                      
CONECT  118   66                                                      
CONECT  119   66                                                      
MASTER        0    0    0    0    0    0    0    0  119    0  119    0
END

https://cactus.nci.nih.gov/chemical/structure/CCCCCCCCCCCC(=O)SCCNC(=O)CCNC(=...
 OpenBabel09142113213D
Jmol version 14.31.45  2021-07-21 05:08 EXTRACT: ({0:118})
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M  END
$$$$

View in JSmol View Stereo Labels

Synonyms

Value	Source
C12:0-CoA	ChEBI
coenzyme A, S-Dodecanoate	ChEBI
Dodecanoyl-CoA	ChEBI
Dodecanoyl-coenzyme A	ChEBI
Lauroyl coenzyme A	ChEBI
Lauroyl-coenzyme A	ChEBI
coenzyme A, S-Dodecanoic acid	Generator

Chemical Formula

C₃₃H₅₈N₇O₁₇P₃S

Average Molecular Weight

949.837

Monoisotopic Molecular Weight

949.282273691

IUPAC Name

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

Traditional Name

lauroyl-coa

CAS Registry Number

6244-92-4

SMILES

CCCCCCCCCCCC(=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/C33H58N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-24(42)61-17-16-35-23(41)14-15-36-31(45)28(44)33(2,3)19-54-60(51,52)57-59(49,50)53-18-22-27(56-58(46,47)48)26(43)32(55-22)40-21-39-25-29(34)37-20-38-30(25)40/h20-22,26-28,32,43-44H,4-19H2,1-3H3,(H,35,41)(H,36,45)(H,49,50)(H,51,52)(H2,34,37,38)(H2,46,47,48)/t22-,26-,27-,28+,32-/m1/s1

InChI Key

YMCXGHLSVALICC-GMHMEAMDSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Hydroxy acids and derivatives

Sub Class

Beta hydroxy acids and derivatives

Direct Parent

Beta hydroxy acids and derivatives

Alternative Parents

Substituents

Beta-hydroxy acid
Monocyclic benzene moiety
Morpholine
Oxazinane
Piperidine
N-alkylpyrrolidine
Benzenoid
Pyrrolidine
Amino acid or derivatives
Carboxylic acid ester
Tertiary amine
Tertiary aliphatic amine
Oxacycle
Organoheterocyclic compound
Azacycle
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Primary alcohol
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Amine
Organic oxide
Carbonyl group
Organic oxygen compound
Organic nitrogen compound
Alcohol
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

tertiary amino compound (CHEBI:16794 )
epoxide (CHEBI:16794 )
propanoate ester (CHEBI:16794 )
tropane alkaloid (CHEBI:16794 )

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Biofluid and excreta:

Urine

Subcellular:

Cell and elements:

Extracellular

Cell:

Fibroblast

Process

Naturally occurring process:

Biological process:

Chemical reaction:

Lipid peroxidation

Cellular process:

Cell signaling

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physical Properties

State

Solid

Experimental Molecular 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 Molecular Properties

Property	Value	Source
Water Solubility	2.59 g/L	ALOGPS
logP	1.35	ALOGPS
logP	-1.2	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	30	ChemAxon
Refractivity	218.24 m³·mol⁻¹	ChemAxon
Polarizability	91.94 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

Predicted Spectral Properties

Collision Cross Sections

Name	Adduct	Type	Data Source	Value	Reference
DeepCCS	[M-H]-	Experimental	MetCCS_train_neg	283.179	30932474
DeepCCS	[M+H]+	Experimental	MetCCS_train_pos	284.021	30932474
AllCCS	[M-H]-	Experimental	Not Available	283.179	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000271
AllCCS	[M+H]+	Experimental	Not Available	285.153	http://allccs.zhulab.cn/database/detail?ID=AllCCS00000271

Retention Indices

Underivatized

Not Available

Derivatized

Not Available

Spectra

LC-MS/MS

Spectrum Type	Description	Splash Key	Deposition Date	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-1911101102-687968f22ae76ca547b2	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000i-0931300000-f614ebfa62da3b2be8e6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-000i-1910102000-031217cf76abed1b705f	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-003r-3922021304-259fa0e4c2115b5176b6	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-001i-2901100001-efdce198394adecd9a34	2015-09-15	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-057i-6900100000-7e1a4d11b2e1da20a826	2015-09-15	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane
Peroxisome

Biospecimen Locations

Not Available

Tissue Locations

Fibroblasts

Pathways

Name	SMPDB/Pathwhiz	KEGG
Beta Oxidation of Very Long Chain Fatty Acids
Fatty acid Metabolism
Fatty Acid Elongation In Mitochondria
Mitochondrial Beta-Oxidation of Long Chain Saturated Fatty Acids		Not Available
Mitochondrial Beta-Oxidation of Medium Chain Saturated Fatty Acids		Not Available

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB03264

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023198

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Wikipedia Link

Not Available

METLIN ID

6959

PubChem Compound

165436

PDB ID

Not Available

ChEBI ID

15521

Food Biomarker Ontology

Not Available

VMH ID

DDCACOA

MarkerDB ID

Not Available

References

Synthesis Reference

Eaton, Simon; Turnbull, Douglass M.; Bartlett, Kim. Redox control of b-oxidation in rat liver mitochondria. European Journal of Biochemistry (1994), 220(3), 671-81.

Material Safety Data Sheet (MSDS)

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. [PubMed:15638818 ]

Only showing the first 10 proteins. There are 112 proteins in total.

Show all enzymes and transporters

Enzymes

Enzyme Details

1. 3-ketoacyl-CoA thiolase, mitochondrial

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Abolishes BNIP3-mediated apoptosis and mitochondrial damage.
Gene Name:: ACAA2
Uniprot ID:: P42765
Molecular weight:: 41923.82

Reactions

Lauroyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxotetradecanoyl-CoA	details

Enzyme Details

2. 3-ketoacyl-CoA thiolase, peroxisomal

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Not Available
Gene Name:: ACAA1
Uniprot ID:: P09110
Molecular weight:: 34664.46

Reactions

Lauroyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxotetradecanoyl-CoA	details

Enzyme Details

3. Trifunctional enzyme subunit beta, mitochondrial

General function:: Involved in transferase activity, transferring acyl groups other than amino-acyl groups
Specific function:: Not Available
Gene Name:: HADHB
Uniprot ID:: P55084
Molecular weight:: 51293.955

Reactions

Lauroyl-CoA + Acetyl-CoA → Coenzyme A + 3-Oxotetradecanoyl-CoA	details

Enzyme Details

4. Methylmalonate-semialdehyde dehydrogenase [acylating], mitochondrial

General function:: Involved in oxidoreductase activity
Specific function:: Plays a role in valine and pyrimidine metabolism. Binds fatty acyl-CoA.
Gene Name:: ALDH6A1
Uniprot ID:: Q02252
Molecular weight:: 57839.31

Enzyme Details

5. Long-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: ACADL
Uniprot ID:: P28330
Molecular weight:: 47655.275

Reactions

Lauroyl-CoA + FAD → (2E)-Dodecenoyl-CoA + FADH	details

Enzyme Details

6. Short-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: ACADS
Uniprot ID:: P16219
Molecular weight:: 44296.705

Enzyme Details

7. Medium-chain specific acyl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: This enzyme is specific for acyl chain lengths of 4 to 16.
Gene Name:: ACADM
Uniprot ID:: P11310
Molecular weight:: 46587.98

Reactions

Lauroyl-CoA + FAD → (2E)-Dodecenoyl-CoA + FADH	details

Enzyme Details

8. Peroxisomal acyl-coenzyme A oxidase 1

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Catalyzes the desaturation of acyl-CoAs to 2-trans-enoyl-CoAs. Isoform 1 shows highest activity against medium-chain fatty acyl-CoAs and activity decreases with increasing chain length. Isoform 2 is active against a much broader range of substrates and shows activity towards very long-chain acyl-CoAs. Isoform 2 is twice as active as isoform 1 against 16-hydroxy-palmitoyl-CoA and is 25% more active against 1,16-hexadecanodioyl-CoA.
Gene Name:: ACOX1
Uniprot ID:: Q15067
Molecular weight:: 70135.205

Reactions

Lauroyl-CoA + FAD → (2E)-Dodecenoyl-CoA + FADH	details

Enzyme Details

9. Peroxisomal acyl-coenzyme A oxidase 2

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Oxidizes the CoA esters of the bile acid intermediates di- and tri-hydroxycholestanoic acids.
Gene Name:: ACOX2
Uniprot ID:: Q99424
Molecular weight:: 76826.14

Enzyme Details

10. Isovaleryl-CoA dehydrogenase, mitochondrial

General function:: Involved in acyl-CoA dehydrogenase activity
Specific function:: Not Available
Gene Name:: IVD
Uniprot ID:: P26440
Molecular weight:: 43055.325

Transporters

Enzyme Details

1. Long-chain fatty acid transport protein 1

General function:: Lipid transport and metabolism
Specific function:: Involved in translocation of long-chain fatty acids (LFCA) across the plasma membrane. The LFCA import appears to be hormone-regulated in a tissue-specific manner. In adipocytes, but not myocytes, insulin induces a rapid translocation of FATP1 from intracellular compartments to the plasma membrane, paralleled by increased LFCA uptake. May act directly as a bona fide transporter, or alternatively, in a cytoplasmic or membrane- associated multimeric protein complex to trap and draw fatty acids towards accumulation. Plays a pivotal role in regulating available LFCA substrates from exogenous sources in tissues undergoing high levels of beta-oxidation or triglyceride synthesis. May be involved in regulation of cholesterol metabolism. Has acyl-CoA ligase activity for long-chain and very-long-chain fatty acids
Gene Name:: SLC27A1
Uniprot ID:: Q6PCB7
Molecular weight:: 71107.5

Only showing the first 10 proteins. There are 112 proteins in total.

Show all enzymes and transporters

Showing metabocard for Lauroyl-CoA (HMDB0003571)

MOL for HMDB0003571 (Lauroyl-CoA)

3D MOL for HMDB0003571 (Lauroyl-CoA)

3D SDF for HMDB0003571 (Lauroyl-CoA)

3D-SDF for HMDB0003571 (Lauroyl-CoA)

PDB for HMDB0003571 (Lauroyl-CoA)

3D PDB for HMDB0003571 (Lauroyl-CoA)

SMILES for HMDB0003571 (Lauroyl-CoA)

INCHI for HMDB0003571 (Lauroyl-CoA)

Structure for HMDB0003571 (Lauroyl-CoA)

3D Structure for HMDB0003571 (Lauroyl-CoA)

Collision Cross Sections

Retention Indices

Underivatized

Derivatized

LC-MS/MS

Enzymes

Reactions

Reactions

Reactions

Reactions

Reactions

Reactions

Transporters