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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2005-11-20 22:13:23 UTC
Update Date2021-10-13 04:35:54 UTC
HMDB IDHMDB0001568
Secondary Accession Numbers
  • HMDB0010723
  • HMDB01568
  • HMDB10723
Metabolite Identification
Common Nametrans-2-Octenoic acid
Descriptiontrans-2-Octenoic acid or (2E)-oct-2-enoic acid is an olefinic fatty acid that is octanoic acid carrying a double bond at position 2 (the 2E-isomer). It has a role as an animal metabolite. It is a medium-chain fatty acid, a monounsaturated fatty acid, a straight-chain fatty acid and an olefinic fatty acid. It is a conjugate acid of a (2E)-oct-2-enoate.
Structure
Data?1582752210
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
Disposition

Biological location

Source

Route of exposure

Process

Naturally occurring process

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point5 - 6 °CNot Available
Boiling Point139.00 to 141.00 °C. @ 13.00 mm HgThe Good Scents Company Information System
Water Solubility0The Good Scents Company Information System
LogP2.9Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M-H]-MetCCS_train_neg141.13430932474
[M-H]-Not Available141.134http://allccs.zhulab.cn/database/detail?ID=AllCCS00000256
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.74 g/LALOGPS
logP10(3.01) g/LALOGPS
logP10(2.7) g/LChemAxon
logS10(-2.3) g/LALOGPS
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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+135.24231661259
DarkChem[M-H]-131.93231661259
AllCCS[M+H]+134.53732859911
AllCCS[M-H]-135.76232859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
trans-2-Octenoic acidCCCCC\C=C\C(O)=O2241.7Standard polar33892256
trans-2-Octenoic acidCCCCC\C=C\C(O)=O1195.5Standard non polar33892256
trans-2-Octenoic acidCCCCC\C=C\C(O)=O1217.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
trans-2-Octenoic acid,1TMS,isomer #1CCCCC/C=C/C(=O)O[Si](C)(C)C1310.5Semi standard non polar33892256
trans-2-Octenoic acid,1TBDMS,isomer #1CCCCC/C=C/C(=O)O[Si](C)(C)C(C)(C)C1528.7Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - trans-2-Octenoic acid EI-B (Non-derivatized)splash10-0096-9000000000-801c8e0537a0c78cb64f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - trans-2-Octenoic acid EI-B (Non-derivatized)splash10-0096-9000000000-801c8e0537a0c78cb64f2018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-2-Octenoic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-054x-9100000000-674e58e1403584c375102016-09-22Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-2-Octenoic acid GC-MS (1 TMS) - 70eV, Positivesplash10-05i3-9300000000-009fbcd018a04b967cd12017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-2-Octenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - trans-2-Octenoic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-2-Octenoic acid Quattro_QQQ 10V, Negative-QTOF (Annotated)splash10-0006-1900000000-b7bf23a0b3d2e169aaaf2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-2-Octenoic acid Quattro_QQQ 25V, Negative-QTOF (Annotated)splash10-0006-3900000000-8f50ffbb66fd8d8a40932012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-2-Octenoic acid Quattro_QQQ 40V, Negative-QTOF (Annotated)splash10-0006-4900000000-9d8bc0c8f59ac419fbfd2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - trans-2-Octenoic acid EI-B (HITACHI M-80B) , Positive-QTOFsplash10-0096-9000000000-41aeee8c78cb838799da2012-08-31HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2-Octenoic acid 10V, Positive-QTOFsplash10-002f-3900000000-eabda8115bfbf3fc6fca2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2-Octenoic acid 20V, Positive-QTOFsplash10-001m-9200000000-38d844ded2c3da09c7462016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2-Octenoic acid 40V, Positive-QTOFsplash10-0006-9000000000-b1716f6f88db0d93c4952016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2-Octenoic acid 10V, Negative-QTOFsplash10-0006-1900000000-5d702aa87f7d38dc20092016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2-Octenoic acid 20V, Negative-QTOFsplash10-0007-6900000000-ddfae845c01ce646730e2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2-Octenoic acid 40V, Negative-QTOFsplash10-0007-9100000000-f2b136da6cc734a29fab2016-09-14Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2-Octenoic acid 10V, Negative-QTOFsplash10-00dl-0900000000-e92c8d4ba859e2c18a1a2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2-Octenoic acid 20V, Negative-QTOFsplash10-0596-0900000000-15af8a5dc0356cd2f4b02021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2-Octenoic acid 40V, Negative-QTOFsplash10-00kf-9000000000-5f0acc9c148a535551fd2021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2-Octenoic acid 10V, Positive-QTOFsplash10-0a4i-9100000000-35fbf6036a26b499b0402021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2-Octenoic acid 20V, Positive-QTOFsplash10-0a4i-9000000000-a8d30352fd0b19afc3f02021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - trans-2-Octenoic acid 40V, Positive-QTOFsplash10-0a4i-9000000000-45f40a1dbaae13a04dae2021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, CD3OD, experimental)2012-12-05Wishart LabView Spectrum
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 IDNot Available
Good Scents IDrw1048161
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 ]