Showing metabocard for trans-2-Octenoic acid (BMDB0001568)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:47:47 UTC
Update Date2020-05-21 16:27:14 UTC
BMDB IDBMDB0001568
Secondary Accession Numbers
  • BMDB01568
Metabolite Identification
Common Nametrans-2-Octenoic acid
Descriptiontrans-2-Octenoic acid, also known as trans-2-octenoic acid, 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. trans-2-Octenoic acid exists as a liquid, very hydrophobic, practically insoluble (in water), and relatively neutral molecule. trans-2-Octenoic acid exists in all eukaryotes, ranging from yeast to humans. trans-2-Octenoic acid participates in a number of enzymatic reactions, within cattle. In particular, trans-2-Octenoic acid can be biosynthesized from (R)-3-hydroxyoctanoic acid; which is mediated by the enzyme fatty acid synthase. dyhydrase domain. In addition, trans-2-Octenoic acid can be converted into caprylic acid through its interaction with the enzyme fatty acid synthase. enoyl reductase domain. In cattle, trans-2-octenoic acid is involved in the metabolic pathway called fatty acid biosynthesis pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(e)-2-Octenoic acidChEBI
2-Octenoic acidChEBI
trans-alpha-Octenoic acidChEBI
(e)-2-OctenoateGenerator
2-OctenoateGenerator
trans-a-OctenoateGenerator
trans-a-Octenoic acidGenerator
trans-alpha-OctenoateGenerator
trans-Α-octenoateGenerator
trans-Α-octenoic acidGenerator
trans-2-OctenoateGenerator
(2E)-2-Octenoic acidHMDB
(2E)-Oct-2-enoic acidHMDB
trans-2-Octenoic acidHMDB, ChEBI
(e)-Oct-2-enoateHMDB
(e)-Oct-2-enoic 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
Description 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
StatusExpected but not Quantified
Origin
  • Endogenous
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
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
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0096-9000000000-801c8e0537a0c78cb64fView in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0096-9000000000-801c8e0537a0c78cb64fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-054x-9100000000-674e58e1403584c37510View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-05i3-9300000000-009fbcd018a04b967cd1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
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, Positivesplash10-002f-3900000000-eabda8115bfbf3fc6fcaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-001m-9200000000-38d844ded2c3da09c746View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-b1716f6f88db0d93c495View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-5d702aa87f7d38dc2009View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0007-6900000000-ddfae845c01ce646730eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0007-9100000000-f2b136da6cc734a29fabView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00dl-0900000000-e92c8d4ba859e2c18a1aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0596-0900000000-15af8a5dc0356cd2f4b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kf-9000000000-5f0acc9c148a535551fdView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-9100000000-35fbf6036a26b499b040View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-9000000000-a8d30352fd0b19afc3f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a4i-9000000000-45f40a1dbaae13a04daeView in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Adiposome
  • Cell membrane
  • Cytoplasm
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001568
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
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)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Fatty acid synthase
General function:
Secondary metabolites biosynthesis, transport and catabolism
Specific function:
Fatty acid synthetase catalyzes the formation of long-chain fatty acids from acetyl-CoA, malonyl-CoA and NADPH. This multifunctional protein has 7 catalytic activities as an acyl carrier protein.
Gene Name:
FASN
Uniprot ID:
Q71SP7
Molecular weight:
274554.0
Reactions
(R)-3-Hydroxyoctanoic acid → trans-2-Octenoic aciddetails
trans-2-Octenoic acid → Caprylic aciddetails