Survey with prize
You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on Human Metabolome Database.

Showing metabocard for trans-2-Octenoic acid (HMDB0001568)

Jump To Section:
IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesXML
Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-20 22:13:23 UTC
Update Date2020-02-26 21:23:30 UTC
HMDB IDHMDB0001568
Secondary Accession Numbers
  • HMDB0010723
  • HMDB01568
  • 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 (PMID: 1963884 ).
Structure
Data?1582752210
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
(e)-2-Octenoic acidChEBI
trans-alpha-Octenoic acidChEBI
(e)-2-OctenoateGenerator
trans-2-OctenoateGenerator
trans-a-OctenoateGenerator
trans-a-Octenoic acidGenerator
trans-alpha-OctenoateGenerator
trans-α-octenoateGenerator
trans-α-octenoic acidGenerator
(e)-Oct-2-enoateHMDB
(e)-Oct-2-enoic acidHMDB
(2E)-2-Octenoic acidHMDB
(2E)-Oct-2-enoic acidHMDB
trans-2-Octenoic acidHMDB
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 KeyCWMPPVPFLSZGCY-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
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateLiquid
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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity41.37 m³·mol⁻¹ChemAxon
Polarizability16.45 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0096-9000000000-801c8e0537a0c78cb64fSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0096-9000000000-801c8e0537a0c78cb64fSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054x-9100000000-674e58e1403584c37510Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05i3-9300000000-009fbcd018a04b967cd1Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-0006-1900000000-b7bf23a0b3d2e169aaafSpectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-0006-3900000000-8f50ffbb66fd8d8a4093Spectrum
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-0006-4900000000-9d8bc0c8f59ac419fbfdSpectrum
LC-MS/MSLC-MS/MS Spectrum - EI-B (HITACHI M-80B) , Positivesplash10-0096-9000000000-41aeee8c78cb838799daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-002f-3900000000-eabda8115bfbf3fc6fcaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001m-9200000000-38d844ded2c3da09c746Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-b1716f6f88db0d93c495Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-5d702aa87f7d38dc2009Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-6900000000-ddfae845c01ce646730eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9100000000-f2b136da6cc734a29fabSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR1H NMR SpectrumNot AvailableSpectrum
1D NMR13C NMR SpectrumNot AvailableSpectrum
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableSpectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
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 IDFDB001088
KNApSAcK IDNot Available
Chemspider ID4445841
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID6328
PubChem Compound5282714
PDB IDNot Available
ChEBI ID86544
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
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 References
  1. Guha L, Seenivasagan T, Iqbal ST, Agrawal OP, Parashar BD: Behavioral and electrophysiological responses of Aedes albopictus to certain acids and alcohols present in human skin emanations. Parasitol Res. 2014 Oct;113(10):3781-7. doi: 10.1007/s00436-014-4044-0. Epub 2014 Jul 23. [PubMed:25049052 ]
  2. Galdiero F, Folgore A, Galdiero M, Tufano MA: Effect of modification of HEp 2 cell membrane lipidic phase on susceptibility to infection from herpes simplex virus. Infection. 1990 Nov-Dec;18(6):372-5. [PubMed:1963884 ]