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Human Metabolome Database Version 3.5

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Showing metabocard for (3S)-3-Hydroxylinoleoyl-CoA (HMDB12477)

Record Information
Version 3.5
Creation Date 2009-07-24 18:01:19 -0600
Update Date 2013-04-05 15:50:14 -0600
HMDB ID HMDB12477
Secondary Accession Numbers None
Metabolite Identification
Common Name (3S)-3-Hydroxylinoleoyl-CoA
Description (3S)-3-hydroxylinoleoyl-CoA is an acyl-CoA with (3S)-3-hydroxylinoleoate moiety. Acyl-CoA (or formyl-CoA) is a coenzyme involved in the metabolism of fatty acids. It is a temporary compound formed when coenzyme A (CoA) attaches to the end of a long-chain fatty acid inside living cells. The compound undergoes beta oxidation, forming one or more molecules of acetyl-CoA. This, in turn, enters the citric acid cycle, eventually forming several molecules of ATP. (3S)-3-hydroxylinoleoyl-CoA is an intermediate in Di-unsaturated fatty acid beta-oxidation pathway. In the reaction, it acts as the precursor of producing (3S)-3-hydroxylinoleoyl-CoA[X].
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  1. (3S)-3-hydroxy-cis,cis-9,12-octadecadienoyl-CoA
  2. (3S)-3-hydroxy-cis,cis-9,12-octadecadienoyl-Coenzyme A
  3. 3(S)-Hydroxy-9Z,12Z-octadecadienoyl-CoA
  4. 3(S)-Hydroxy-9Z,12Z-octadecadienoyl-Coenzyme A
  5. 3(S)-Hydroxy-cis,cis-9,12-octadecadienoyl-Coenzime A
  6. 3(S)-Hydroxyoctadeca-cis,cis-9,12-dienoyl-CoA
  7. 3(S)-Hydroxyoctadeca-cis,cis-9,12-dienoyl-Coenzyme A
Chemical Formula C39H62N7O18P3S
Average Molecular Weight 1041.932
Monoisotopic Molecular Weight 1041.308488441
IUPAC Name 3-hydroxy-3-({2-[(2-{[(3S,9Z,12Z)-3-hydroxyoctadeca-9,12-dienoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropyl ({[(2R,3R,4S,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxy)phosphonate
Traditional IUPAC Name 3-hydroxy-3-({2-[(2-{[(3S,9Z,12Z)-3-hydroxyoctadeca-9,12-dienoyl]sulfanyl}ethyl)carbamoyl]ethyl}carbamoyl)-2,2-dimethylpropyl {[(2R,3R,4S,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-3-(phosphonatooxy)oxolan-2-yl]methyl phosphonato}oxyphosphonate
CAS Registry Number Not Available
SMILES CCCCC\C=C/C\C=C/CCCCC[C@H](O)CC(=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/C39H66N7O18P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-27(47)22-30(49)68-21-20-41-29(48)18-19-42-37(52)34(51)39(2,3)24-61-67(58,59)64-66(56,57)60-23-28-33(63-65(53,54)55)32(50)38(62-28)46-26-45-31-35(40)43-25-44-36(31)46/h8-9,11-12,25-28,32-34,38,47,50-51H,4-7,10,13-24H2,1-3H3,(H,41,48)(H,42,52)(H,56,57)(H,58,59)(H2,40,43,44)(H2,53,54,55)/p-4/b9-8-,12-11-/t27-,28+,32-,33-,34?,38+/m0/s1
InChI Key ICMPOMMDSLXBOC-VDDVCRISSA-J
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acid Esters
Sub Class Acyl CoAs
Other Descriptors
  • Aromatic Heteropolycyclic Compounds
Substituents
  • 1 Phosphoribosyl Imidazole
  • Carboxamide Group
  • Carboxylic Thioester
  • Coenzyme A
  • Glycosyl Compound
  • Imidazole
  • Imidazopyrimidine
  • Monosaccharide Phosphate
  • N Glycosyl Compound
  • Organic Hypophosphite
  • Organic Phosphite
  • Organic Pyrophosphate
  • Oxolane
  • Pentose Monosaccharide
  • Phosphoric Acid Ester
  • Purine
  • Purine Ribonucleoside Diphosphate
  • Pyrimidine
  • Saccharide
  • Secondary Alcohol
  • Secondary Carboxylic Acid Amide
  • Thiocarboxylic Acid Ester
Direct Parent Acyl CoAs
Ontology
Status Expected and Not Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
Physical Properties
State Solid
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
Water Solubility 1.69 g/L ALOGPS
LogP 3.00 ALOGPS
LogP -1.6 ChemAxon
LogS -2.82 ALOGPS
pKa (strongest acidic) 0.83 ChemAxon
pKa (strongest basic) 4.95 ChemAxon
Hydrogen Acceptor Count 18 ChemAxon
Hydrogen Donor Count 6 ChemAxon
Polar Surface Area 395.18 A2 ChemAxon
Rotatable Bond Count 34 ChemAxon
Refractivity 245.11 ChemAxon
Polarizability 101.89 ChemAxon
Formal Charge -4 ChemAxon
Physiological Charge -4 ChemAxon
Spectra
Not Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations Not Available
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease References None
Associated OMIM IDs None
DrugBank ID Not Available
DrugBank Metabolite ID Not Available
Phenol Explorer Compound ID Not Available
Phenol Explorer Metabolite ID Not Available
FoodDB ID FDB029087
KNApSAcK ID Not Available
Chemspider ID Not Available
KEGG Compound ID Not Available
BioCyc ID Not Available
BiGG ID Not Available
Wikipedia Link Not Available
NuGOwiki Link HMDB12477 Link_out
Metagene Link HMDB12477 Link_out
METLIN ID Not Available
PubChem Compound 53481430 Link_out
PDB ID Not Available
ChEBI ID Not Available
References
Synthesis Reference Not Available
Material Safety Data Sheet (MSDS) Not Available
General References Not Available