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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2019-07-23 05:44:04 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. 2-Octenedioic acid is a weakly acidic compound (based on its pKa).
Structure
Data?1563860644
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
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000e-9300000000-f1a09c8baab1ebacd19eJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00fr-9741000000-56f639d2fb2625d3cdbbJSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-000i-2900000000-9b5e8c7acbeffa7a7bffJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-001i-9000000000-aa84fcbe642b74aa9e12JSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-016u-9000000000-a9bca1da2edcacdb888aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0900000000-80506768aa9d594be0c6JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-2900000000-74cc16e06c099daad389JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-015i-9100000000-08861ade868bf4d03dfaJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-3b5890274a618a3778b5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0900000000-0fe0b507570004cbecf9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9300000000-45583d6735565af2116fJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
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
FoodDB IDFDB021965
KNApSAcK IDNot Available
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
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 ]