3-Oxooctadecanoyl-CoA (PAMDB001579)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB001579
Identification
Name: 3-Oxooctadecanoyl-CoA
Description:3-Oxooctadecanoyl-CoA is a metabolite intermediate in the microsomal fatty acid chain elongation system. Microsomal electron-transport components NADPH-cytochrome P450 reductase (EC 1.6.2.4) and cytochrome b5 (EC 1.6.2.2) participate in the conversion from 3-Oxooctadecanoyl-CoA to beta-hydroxystearoyl-CoA, the first reductive step of the microsomal chain elongating system initiated by NADPH.
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxooctadecanoyl)sulfanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphate}
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxooctadecanoyl)sulfanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphoric acid}
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxooctadecanoyl)sulphanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphate}
  • 3'-Phosphoadenosine 5'-{3-[(3R)-3-hydroxy-2,2-dimethyl-4-oxo-4-{[3-oxo-3-({2-[(3-oxooctadecanoyl)sulphanyl]ethyl}amino)propyl]amino}butyl] dihydrogen diphosphoric acid}
  • 3-Ketostearoyl-coa
  • 3-Ketostearoyl-coenzyme A
  • 3-Oxooctadecanoyl-CoA
  • 3-Oxooctadecanoyl-coenzyme A
  • 3-Oxostearoyl-CoA
  • 3-Oxostearoyl-Coenzyme A
  • b-Ketostearoyl-CoA
  • b-Ketostearoyl-coenzyme A
  • Beta-Ketostearoyl-CoA
  • Beta-Ketostearoyl-Coenzyme A
  • β-Ketostearoyl-CoA
  • β-Ketostearoyl-coenzyme A
Chemical Formula: C39H66N7O18P3S
Average Molecular Weight: 1045.964
Monoisotopic Molecular Weight: 1045.339788569
InChI Key: LGOGWHDPDVAUNY-LFZQUHGESA-L
InChI:InChI=1S/C39H68N7O18P3S/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/h25-26,28,32-34,38,50-51H,4-24H2,1-3H3,(H,41,48)(H,42,52)(H,56,57)(H,58,59)(H2,40,43,44)(H2,53,54,55)/p-2/t28-,32-,33-,34+,38-/m1/s1
CAS number: 86370-20-9
IUPAC Name:{[(2R,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxooctadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional IUPAC Name: 3-oxooctadecanoyl-coa
SMILES:CCCCCCCCCCCCCCCC(=O)CC(=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
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as long-chain 3-oxoacyl coas. These are organic compounds containing a coenzyme A derivative, which is 3-oxo acylated long aliphatic chain of 13 to 21 carbon atoms.
Kingdom Organic compounds
Super ClassLipids and lipid-like molecules
Class Fatty Acyls
Sub ClassFatty acyl thioesters
Direct Parent Long-chain 3-oxoacyl CoAs
Alternative Parents
Substituents
  • Coenzyme a or derivatives
  • Purine ribonucleoside diphosphate
  • Purine ribonucleoside 3',5'-bisphosphate
  • N-glycosyl compound
  • Glycosyl compound
  • Organic pyrophosphate
  • Monosaccharide phosphate
  • 6-aminopurine
  • Purine
  • Imidazopyrimidine
  • Monoalkyl phosphate
  • Aminopyrimidine
  • Imidolactam
  • Alkyl phosphate
  • 1,3-dicarbonyl compound
  • Pyrimidine
  • Primary aromatic amine
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Organic phosphate
  • N-substituted imidazole
  • Monosaccharide
  • Heteroaromatic compound
  • Oxolane
  • Imidazole
  • Azole
  • Thiocarboxylic acid ester
  • Secondary alcohol
  • Ketone
  • Oxacycle
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Sulfenyl compound
  • Thioether
  • Thiocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Hydrocarbon derivative
  • Primary amine
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular Framework Aromatic heteropolycyclic compounds
External Descriptors
Physical Properties
State: Solid
Charge:-4
Melting point: Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility1.61 mg/mLALOGPS
logP2.43ALOGPS
logP-0.27ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)0.83ChemAxon
pKa (Strongest Basic)4.95ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area380.7 Å2ChemAxon
Rotatable Bond Count36ChemAxon
Refractivity246.54 m3·mol-1ChemAxon
Polarizability104.91 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
3-Oxooctadecanoyl-CoA + Coenzyme A <> Acetyl-CoA + Palmityl-CoA
3-Oxooctadecanoyl-CoA + Hydrogen ion + NADH <> (S)-3-Hydroxyoctadecanoyl-CoA + NAD
3-Oxooctadecanoyl-CoA + NADPH + Hydrogen ion <> 3-Hydroxyoctadecanoyl-CoA + NADP
(S)-3-Hydroxyoctadecanoyl-CoA + NAD > NADH + Hydrogen ion + 3-Oxooctadecanoyl-CoA + 3-Oxooctadecanoyl-CoA
3-Oxooctadecanoyl-CoA + Coenzyme A + 3-Oxooctadecanoyl-CoA > Acetyl-CoA + Stearoyl-CoA + Stearoyl-CoA
Pathways: Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-4901020100-42e12c9443811aa9b23aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0922130000-507f0cf5c97de000bbd3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000i-1900000100-92fc72df57fb89aa8c96View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0059-9661331400-f14ff1dd26fae045a551View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-003r-4920200000-f6293880f1450083d4cbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-057i-7900000000-23f4e90322bfc73a51a5View in MoNA
References
References:
  • Nagao, M., Ishibashi, T., Okayasu, T., Imai, Y. (1983). "Possible involvement of NADPH-cytochrome P450 reductase and cytochrome b5 on beta-ketostearoyl-CoA reduction in microsomal fatty acid chain elongation supported by NADPH." FEBS Lett 155:11-14. Pubmed: 6404652
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
CHEBI ID50571
HMDB IDHMDB06498
Pubchem Compound ID23724660
Kegg IDC16216
ChemSpider ID21865760
Wikipedia IDNot Available
BioCyc IDCPD-10260
EcoCyc IDCPD-10260