Hmdb loader
Survey
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 12:20:13 UTC
Update Date2022-03-07 02:49:32 UTC
HMDB IDHMDB0006498
Secondary Accession Numbers
  • HMDB06498
Metabolite Identification
Common Name3-Oxooctadecanoyl-CoA
Description3-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. (PMID: 6404652 ).
Structure
Data?1582752387
Synonyms
ValueSource
3-Ketostearoyl-CoAHMDB
3-Ketostearoyl-coenzyme AHMDB
3-Oxostearoyl-CoAHMDB
3-Oxostearoyl-coenzyme AHMDB
beta-Ketostearoyl-CoAHMDB
beta-Ketostearoyl-coenzyme AHMDB
Chemical FormulaC39H68N7O18P3S
Average Molecular Weight1047.99
Monoisotopic Molecular Weight1047.355440546
IUPAC Name{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({[hydroxy(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 Name[5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy(3-hydroxy-2,2-dimethyl-3-{[2-({2-[(3-oxooctadecanoyl)sulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid
CAS Registry Number86370-20-9
SMILES
CCCCCCCCCCCCCCCC(=O)CC(=O)SCCNC(=O)CCNC(=O)C(O)C(C)(C)COP(O)(=O)OP(O)(=O)OCC1OC(C(O)C1OP(O)(O)=O)N1C=NC2=C1N=CN=C2N
InChI Identifier
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)
InChI KeyLGOGWHDPDVAUNY-UHFFFAOYSA-N
Chemical Taxonomy
Description 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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-chain 3-oxoacyl 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
  • Glycosyl compound
  • N-glycosyl compound
  • 6-aminopurine
  • Monosaccharide phosphate
  • Organic pyrophosphate
  • Pentose monosaccharide
  • Imidazopyrimidine
  • Purine
  • Aminopyrimidine
  • Monoalkyl phosphate
  • 1,3-dicarbonyl compound
  • Pyrimidine
  • Alkyl phosphate
  • Monosaccharide
  • N-substituted imidazole
  • Organic phosphoric acid derivative
  • Phosphoric acid ester
  • Imidolactam
  • Azole
  • Imidazole
  • Heteroaromatic compound
  • Oxolane
  • Thiocarboxylic acid ester
  • Amino acid or derivatives
  • Secondary alcohol
  • Ketone
  • Carbothioic s-ester
  • Azacycle
  • Organoheterocyclic compound
  • Organic 1,3-dipolar compound
  • Propargyl-type 1,3-dipolar organic compound
  • Oxacycle
  • Sulfenyl compound
  • Thiocarboxylic acid or derivatives
  • Carboximidic acid
  • Carboximidic acid derivative
  • Carboxylic acid derivative
  • Primary amine
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Amine
  • Carbonyl group
  • Alcohol
  • Organonitrogen compound
  • Organooxygen compound
  • Organosulfur compound
  • Organic nitrogen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.9 g/LALOGPS
logP2.43ALOGPS
logP0.82ChemAxon
logS-2.8ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count18ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area380.7 ŲChemAxon
Rotatable Bond Count36ChemAxon
Refractivity246.54 m³·mol⁻¹ChemAxon
Polarizability105.04 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+253.60130932474
DeepCCS[M-H]-251.86130932474
DeepCCS[M-2H]-285.89530932474
DeepCCS[M+Na]+259.67130932474
AllCCS[M+H]+299.532859911
AllCCS[M+H-H2O]+300.132859911
AllCCS[M+NH4]+298.932859911
AllCCS[M+Na]+298.732859911
AllCCS[M-H]-300.832859911
AllCCS[M+Na-2H]-306.632859911
AllCCS[M+HCOO]-312.932859911

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxooctadecanoyl-CoA 10V, Positive-QTOFsplash10-000i-4901120200-957cfb9a3dcf4dbe570e2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxooctadecanoyl-CoA 20V, Positive-QTOFsplash10-000i-1912140000-f77738636d793e56c3c52019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxooctadecanoyl-CoA 40V, Positive-QTOFsplash10-000i-1900010000-1ff9c07493324beba76b2019-02-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxooctadecanoyl-CoA 10V, Negative-QTOFsplash10-0059-9661331400-e950466d6890a7ebe1972019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxooctadecanoyl-CoA 20V, Negative-QTOFsplash10-003r-5930210000-2c6beeecd575220cff982019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxooctadecanoyl-CoA 40V, Negative-QTOFsplash10-057i-5900100000-10b6c4bd4be88024fa802019-02-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxooctadecanoyl-CoA 10V, Positive-QTOFsplash10-000t-9000000000-2fb0137671e19fe511672021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxooctadecanoyl-CoA 20V, Positive-QTOFsplash10-01q0-9701100146-18227cc83159065548ba2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxooctadecanoyl-CoA 40V, Positive-QTOFsplash10-0006-0000490000-9e83b8c4c36c5dc46d4b2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxooctadecanoyl-CoA 10V, Negative-QTOFsplash10-0002-9000000000-9b6313eea7e9cedf18012021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxooctadecanoyl-CoA 20V, Negative-QTOFsplash10-004j-9100201220-e270c9bea2bd7337f5822021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 3-Oxooctadecanoyl-CoA 40V, Negative-QTOFsplash10-00or-9102402403-3ee6b039ebbcf85627aa2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
  • Peroxisome
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023942
KNApSAcK IDNot Available
Chemspider ID17216373
KEGG Compound IDC16216
BioCyc IDNot Available
BiGG ID1452160
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74000474
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH ID3OHODCOA
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Nagao M, Ishibashi T, Okayasu T, Imai Y: 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. 1983 May 2;155(1):11-4. [PubMed:6404652 ]

Enzymes

General function:
Involved in oxidoreductase activity
Specific function:
Catalyzes the transformation of estrone (E1) into estradiol (E2), suggesting a central role in estrogen formation. Its strong expression in ovary and mammary gland suggest that it may constitute the major enzyme responsible for the conversion of E1 to E2 in women. Also has 3-ketoacyl-CoA reductase activity, reducing both long chain 3-ketoacyl-CoAs and long chain fatty acyl-CoAs, suggesting a role in long fatty acid elongation.
Gene Name:
HSD17B12
Uniprot ID:
Q53GQ0
Molecular weight:
34323.875
Reactions
3-Oxooctadecanoyl-CoA + NADPH + Hydrogen Ion → 3-hydroxyoctadecanoyl-CoA + NADPdetails
General function:
Not Available
Specific function:
Condensing enzyme that catalyzes the synthesis of saturated and monounsaturated fatty acids. Highest activity toward C16:0 acyl-CoAs.
Gene Name:
ELOVL6
Uniprot ID:
Q9H5J4
Molecular weight:
31375.81
Reactions
Malonyl-CoA + Palmityl-CoA → 3-Oxooctadecanoyl-CoA + Coenzyme A + Carbon dioxidedetails