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
Version3.6
Creation Date2005-11-20 22:13:23 UTC
Update Date2016-02-11 01:04:56 UTC
HMDB IDHMDB01568
Secondary Accession Numbers
  • HMDB10723
Metabolite Identification
Common Nametrans-2-Octenoic acid
DescriptionAs to unsaturated acids, those with eight carbon atoms, 2-octenoic acid (trans-8: 1[2]) and 2-octynoic acid (8:::1[2]), increase the susceptibility to infection and fluidity while low concentrations of monounsaturated acids with 14 and 18 carbon atoms, myristoleic acid (cis-14:1[9]) and oleic acid (cis-18:1[9]), reduce both the susceptibility to infection and the fluidity of the membrane. [Pubmed 1963884].
Structure
Thumb
Synonyms
ValueSource
(e)-2-OctenoateHMDB
(e)-2-Octenoic acidHMDB
(e)-Oct-2-enoateHMDB
trans-2-OctenoateHMDB
Chemical FormulaC8H14O2
Average Molecular Weight142.1956
Monoisotopic Molecular Weight142.099379692
IUPAC Name(2E)-oct-2-enoic acid
Traditional Nametrans-2-octenoic acid
CAS Registry Number1871-67-6
SMILES
CCCCC\C=C\C(O)=O
InChI Identifier
InChI=1S/C8H14O2/c1-2-3-4-5-6-7-8(9)10/h6-7H,2-5H2,1H3,(H,9,10)/b7-6+
InChI KeyInChIKey=CWMPPVPFLSZGCY-VOTSOKGWSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassFatty Acyls
Sub ClassFatty acids and conjugates
Direct ParentMedium-chain fatty acids
Alternative Parents
Substituents
  • Medium-chain fatty acid
  • Unsaturated fatty acid
  • Straight chain fatty acid
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but 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
StateSolid
Experimental Properties
PropertyValueReference
Melting Point5 - 6 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP2.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.74 mg/mLALOGPS
logP3.01ALOGPS
logP2.7ChemAxon
logS-2.3ALOGPS
pKa (Strongest Acidic)5.25ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.37 m3·mol-1ChemAxon
Polarizability16.45 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0006-1900000000-b7bf23a0b3d2e169aaafView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-3900000000-8f50ffbb66fd8d8a4093View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-4900000000-9d8bc0c8f59ac419fbfdView in MoNA
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0096-9000000000-41aeee8c78cb838799daView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
1D NMR1H NMR SpectrumNot Available
2D NMR[1H,13C] 2D NMR SpectrumNot Available
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Fatty Acid BiosynthesisSMP00456Not Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB001088
KNApSAcK IDNot Available
Chemspider ID4445841
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01568
Metagene LinkHMDB01568
METLIN ID6328
PubChem Compound5282714
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceKameda, Kenji; Chikaki, Mariko; Morimoto, Chie; Jiang, Ming; Okuda, Hiromichi. Insulin-like actions of trans-10-hydroxy-2-decanoic acid and its related substances. Wakan Iyakugaku Zasshi (1996), 13(4), 456-457.
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available