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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2022-03-07 02:49:00 UTC
HMDB IDHMDB0000341
Secondary Accession Numbers
  • HMDB00341
Metabolite Identification
Common Name2-Octenedioic acid
Description2-Octenedioic acid, also known as 2-octenedioate, 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. Based on a literature review a small amount of articles have been published on 2-Octenedioic acid.
Structure
Data?1582752125
Synonyms
ValueSource
2-OctenedioateGenerator
1-Hexene-1,6-dicarboxylateHMDB
1-Hexene-1,6-dicarboxylic acidHMDB
(2E)-Oct-2-enedioateHMDB
Chemical FormulaC8H12O4
Average Molecular Weight172.1785
Monoisotopic Molecular Weight172.073558872
IUPAC Name(2E)-oct-2-enedioic acid
Traditional Name(E)-oct-2-enedioic acid
CAS Registry Number5698-50-0
SMILES
OC(=O)CCCC\C=C\C(O)=O
InChI Identifier
InChI=1S/C8H12O4/c9-7(10)5-3-1-2-4-6-8(11)12/h3,5H,1-2,4,6H2,(H,9,10)(H,11,12)/b5-3+
InChI KeyBNTPVRGYUHJFHN-HWKANZROSA-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
  • Dicarboxylic 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 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 Solubility2.06 g/LALOGPS
logP1.14ALOGPS
logP1.38ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)4.15ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity43.03 m³·mol⁻¹ChemAxon
Polarizability17.61 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+139.89231661259
DarkChem[M-H]-137.6231661259
AllCCS[M+H]+138.31532859911
AllCCS[M-H]-138.05632859911
DeepCCS[M+H]+135.85730932474
DeepCCS[M-H]-132.03930932474
DeepCCS[M-2H]-169.20330932474
DeepCCS[M+Na]+144.65230932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Octenedioic acidOC(=O)CCCC\C=C\C(O)=O2713.8Standard polar33892256
2-Octenedioic acidOC(=O)CCCC\C=C\C(O)=O1357.7Standard non polar33892256
2-Octenedioic acidOC(=O)CCCC\C=C\C(O)=O1593.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Octenedioic acid,1TMS,isomer #1C[Si](C)(C)OC(=O)CCCC/C=C/C(=O)O1662.8Semi standard non polar33892256
2-Octenedioic acid,1TMS,isomer #2C[Si](C)(C)OC(=O)/C=C/CCCCC(=O)O1661.8Semi standard non polar33892256
2-Octenedioic acid,2TMS,isomer #1C[Si](C)(C)OC(=O)/C=C/CCCCC(=O)O[Si](C)(C)C1733.6Semi standard non polar33892256
2-Octenedioic acid,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)CCCC/C=C/C(=O)O1911.4Semi standard non polar33892256
2-Octenedioic acid,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)OC(=O)/C=C/CCCCC(=O)O1903.1Semi standard non polar33892256
2-Octenedioic acid,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)OC(=O)/C=C/CCCCC(=O)O[Si](C)(C)C(C)(C)C2176.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octenedioic acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-000e-9300000000-f1a09c8baab1ebacd19e2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octenedioic acid GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-9741000000-56f639d2fb2625d3cdbb2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octenedioic acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octenedioic acid GC-MS (TMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octenedioic acid GC-MS (TMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octenedioic acid GC-MS (TBDMS_1_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octenedioic acid GC-MS (TBDMS_1_2) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Octenedioic acid GC-MS (TBDMS_2_1) - 70eV, PositiveNot Available2021-11-05Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Octenedioic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)splash10-000i-2900000000-9b5e8c7acbeffa7a7bff2012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Octenedioic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)splash10-001i-9000000000-aa84fcbe642b74aa9e122012-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Octenedioic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)splash10-016u-9000000000-a9bca1da2edcacdb888a2012-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octenedioic acid 10V, Positive-QTOFsplash10-0ab9-0900000000-80506768aa9d594be0c62017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octenedioic acid 20V, Positive-QTOFsplash10-0a6r-2900000000-74cc16e06c099daad3892017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octenedioic acid 40V, Positive-QTOFsplash10-015i-9100000000-08861ade868bf4d03dfa2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octenedioic acid 10V, Negative-QTOFsplash10-00di-0900000000-3b5890274a618a3778b52017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octenedioic acid 20V, Negative-QTOFsplash10-0fk9-0900000000-0fe0b507570004cbecf92017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octenedioic acid 40V, Negative-QTOFsplash10-0a4l-9300000000-45583d6735565af2116f2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octenedioic acid 10V, Negative-QTOFsplash10-00di-0900000000-babb20dbeb5c909004f22021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octenedioic acid 20V, Negative-QTOFsplash10-0a6r-1900000000-5b13ae6b7c8afdc726c12021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octenedioic acid 40V, Negative-QTOFsplash10-0pc3-9100000000-e4e183c717cd0420d5802021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octenedioic acid 10V, Positive-QTOFsplash10-0bt9-2900000000-364a4d0b62fbc3892c432021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octenedioic acid 20V, Positive-QTOFsplash10-015a-9200000000-bf9c4f003c6d7f93b5fc2021-09-22Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Octenedioic acid 40V, Positive-QTOFsplash10-0gbc-9000000000-337718fabcf3039c5d042021-09-22Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Experimental 1D NMR1H NMR Spectrum (1D, 500 MHz, H2O, experimental)2012-12-04Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-29Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biospecimen Locations
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified7.00 umol/mmol creatinineAdult (>18 years old)BothMedium Chain Acyl-CoA Dehydrogenase Deficiency
    • MetaGene: Metabol...
details
UrineDetected and Quantified125.00 (0.00-250.00) umol/mmol creatinineChildren (1-13 years old)BothMedium chain acyl-CoA dehydrogenase deficiency (MCAD)
    • MetaGene: Metabol...
details
UrineDetected and Quantified0-2.8 umol/mmol creatinineChildren (1-13 years old)BothMedium Chain Acyl-CoA Dehydrogenase Deficiency
    • Physician's Guide...
details
UrineDetected and Quantified0-1 umol/mmol creatinineNewborn (0-30 days old)BothMedium Chain Acyl-CoA Dehydrogenase Deficiency
    • Physician's Guide...
details
Associated Disorders and Diseases
Disease References
Medium Chain Acyl-CoA Dehydrogenase Deficiency
  1. G.Frauendienst-Egger, Friedrich K. Trefz (2017). MetaGene: Metabolic & Genetic Information Center (MIC: http://www.metagene.de). METAGENE consortium.
  2. Blau N, Duran M, Blaskovics ME, Gibson KM (2003). Physician's Guide to the Laboratory Diagnosis of Metabolic Diseases. 2nd ed. Berlin, Germany, Springer, 2003. Springer.
Associated OMIM IDs
  • 201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB021965
KNApSAcK IDC00007508
Chemspider ID4800646
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN ID5330
PubChem Compound6079438
PDB IDNot Available
ChEBI ID89192
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceTakada, Kenichi; Ouchi, Shiro; Mineshita, Tetsuo; Hirose, Katsumi. Diuretic action of aliphatic unsaturated dicarboxylic acids. Ann. Repts. Shionogi Research Lab. (1955), No. 5 17-24.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Pitt JJ: Gas chromatographic-mass spectrometric characterisation of unsaturated dicarboxylic acids in urine. J Chromatogr. 1990 Dec 14;534:182-9. [PubMed:2094705 ]
  2. Jin SJ, Tserng KY: Identification of isomeric unsaturated medium-chain dicarboxylic acids in human urine. J Lipid Res. 1989 Oct;30(10):1611-9. [PubMed:2614263 ]