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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2007-05-23 14:04:43 UTC
Update Date2022-03-07 02:49:32 UTC
HMDB IDHMDB0006521
Secondary Accession Numbers
  • HMDB06521
Metabolite Identification
Common Namecis-Vaccenoyl CoA
DescriptionVaccenoyl CoA is a coenzyme A derivative of vaccenic acid. There are both cis (or R) and trans (or S) forms of Vaccenoyl CoA. Vaccenoyl CoA derivatives were found to be active substrates in vitro in the acylation of glycerol 3-phosphate. It is involved in the biosynthesis and oxidation of fatty acids as well as in ceramide formation.
Structure
Data?1582752389
Synonyms
ValueSource
11-Octadecenoyl CoAHMDB
11-Octadecenoyl coenzyme AHMDB
cis-Vaccenoyl coenzyme AHMDB
cis-Vaccenoyl-CoAHMDB
cis-Vaccenoyl-coenzymeHMDB
cis-Vaccenoyl-coenzyme AHMDB
R-11-OctadecenoateHMDB
R-11-Octadecenoate CoAHMDB
R-11-Octadecenoate coenzyme AHMDB
R-11-Octadecenoic acidHMDB
R-11-Octadecenoyl CoAHMDB
R-11-Octadecenoyl coenzyme AHMDB
Vaccenoyl CoAHMDB
Vaccenoyl coenzyme AHMDB
Vaccenoyl-CoAHMDB
Vaccenoyl-coenzymeHMDB
Vaccenoyl-coenzyme AHMDB
Vaccenyl coenzyme AHMDB
Chemical FormulaC39H68N7O17P3S
Average Molecular Weight1031.98
Monoisotopic Molecular Weight1031.360524011
IUPAC Name{[(2R,3R,5R)-5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-({[hydroxy({hydroxy[(3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(11E)-octadec-11-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy]phosphoryl}oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxy}phosphonic acid
Traditional Name[(2R,3R,5R)-5-(6-aminopurin-9-yl)-4-hydroxy-2-({[hydroxy([hydroxy((3R)-3-hydroxy-2,2-dimethyl-3-{[2-({2-[(11E)-octadec-11-enoylsulfanyl]ethyl}carbamoyl)ethyl]carbamoyl}propoxy)phosphoryl]oxy)phosphoryl]oxy}methyl)oxolan-3-yl]oxyphosphonic acid
CAS Registry Number13673-88-6
SMILES
CCCCCC\C=C\CCCCCCCCCC(=O)SCCNC(=O)CCNC(=O)[C@@](O)([H])C(C)(C)COP(=O)(O)OP(=O)(O)OC[C@H]1O[C@H](C(O)[C@H]1OP(=O)(O)O)N1C=NC2=C1N=CN=C2N
InChI Identifier
InChI=1S/C39H68N7O17P3S/c1-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-30(48)67-23-22-41-29(47)20-21-42-37(51)34(50)39(2,3)25-60-66(57,58)63-65(55,56)59-24-28-33(62-64(52,53)54)32(49)38(61-28)46-27-45-31-35(40)43-26-44-36(31)46/h9-10,26-28,32-34,38,49-50H,4-8,11-25H2,1-3H3,(H,41,47)(H,42,51)(H,55,56)(H,57,58)(H2,40,43,44)(H2,52,53,54)/b10-9+/t28-,32?,33+,34+,38-/m1/s1
InChI KeyHEJOXXLSCAQQGQ-HHFSZNSTSA-N
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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acyl thioesters
Direct ParentLong-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 FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Biological location

Source

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
logP2.83ALOGPS
logP1.13ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)0.82ChemAxon
pKa (Strongest Basic)4.01ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count17ChemAxon
Hydrogen Donor Count9ChemAxon
Polar Surface Area363.63 ŲChemAxon
Rotatable Bond Count35ChemAxon
Refractivity246.97 m³·mol⁻¹ChemAxon
Polarizability102.64 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]+288.71730932474
DeepCCS[M-H]-286.99330932474
DeepCCS[M-2H]-321.67530932474
DeepCCS[M+Na]+295.48330932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenoyl CoA 10V, Positive-QTOFsplash10-000i-3902020200-f86b94725c29a58610e02017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenoyl CoA 20V, Positive-QTOFsplash10-000i-1913140000-1d32cb163a97fc2fa14e2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenoyl CoA 40V, Positive-QTOFsplash10-000i-1900010000-11cca0d7c51cc0c9c4252017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenoyl CoA 10V, Negative-QTOFsplash10-01q9-9761431500-77d50d2b249f1a52db7f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenoyl CoA 20V, Negative-QTOFsplash10-01q9-4920210000-ec067874cf289e9db03f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenoyl CoA 40V, Negative-QTOFsplash10-057i-5900100000-2725f27342a0d1efd2b42017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenoyl CoA 10V, Negative-QTOFsplash10-001i-9000000000-0afd0bffa1bd09c6b53c2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenoyl CoA 20V, Negative-QTOFsplash10-003r-9010201300-a1772727e86615fcc7e22021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenoyl CoA 40V, Negative-QTOFsplash10-056r-9103401306-842fc3a3620a91f3e7342021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenoyl CoA 10V, Positive-QTOFsplash10-001i-9000000000-2e5dca73630e0cdc5de02021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenoyl CoA 20V, Positive-QTOFsplash10-01p9-5700100329-343447eb97db430763192021-09-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - cis-Vaccenoyl CoA 40V, Positive-QTOFsplash10-004i-0200790000-281446c2821ac1413e3c2021-09-25Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
  • Mitochondria
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 IDFDB023956
KNApSAcK IDNot Available
Chemspider ID59651610
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG ID2218408
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound53477847
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available