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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:54:37 UTC
HMDB IDHMDB0004982
Secondary Accession Numbers
  • HMDB04982
Metabolite Identification
Common Namecis-4-Octenedioic acid
Description4-Octenedioic acid have been found slightly elevated in the urine of persons with abnormal fatty acid metabolism (PMID 2094705 ). cis-4-Octenedioic acid is found to be associated with medium chain acyl-CoA dehydrogenase deficiency, which is an inborn error of metabolism.
Structure
Thumb
Synonyms
ValueSource
(Z)-4-Octene-1,8-dioateHMDB
(Z)-4-Octene-1,8-dioic acidHMDB
cis-4-Octene-1,8-dioateHMDB
cis-4-Octene-1,8-dioic acidHMDB
cis-4-OctenedioateHMDB
Chemical FormulaC8H12O4
Average Molecular Weight172.1785
Monoisotopic Molecular Weight172.073558872
IUPAC Name(4Z)-oct-4-enedioic acid
Traditional Namecis-4-octenedioic acid
CAS Registry Number38561-68-1
SMILES
OC(=O)CC\C=C/CCC(O)=O
InChI Identifier
InChI=1S/C8H12O4/c9-7(10)5-3-1-2-4-6-8(11)12/h1-2H,3-6H2,(H,9,10)(H,11,12)/b2-1-
InChI KeyLQVYKEXVMZXOAH-UPHRSURJSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as medium-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 4 and 12 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassLipids and lipid-like molecules
Sub ClassFatty Acyls
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 Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

  Biological:

    Animal:

Route of exposure:

  Enteral:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

    Chemical reaction:

    Biochemical process:

    Biochemical pathway:

Role

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point96 - 98 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility3.16 g/LALOGPS
logP0.96ALOGPS
logP1.02ChemAxon
logS-1.7ALOGPS
pKa (Strongest Acidic)4.08ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity43.06 m³·mol⁻¹ChemAxon
Polarizability17.2 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-002b-9700000000-05fd068ced2272cfd647View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-009i-9520000000-59e3c21041662007d302View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, N/A (Annotated)splash10-052r-0900000000-dcb0faa12f86c5e6d354View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, N/A (Annotated)splash10-001i-9100000000-2fb14d29c61748d9bc25View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, N/A (Annotated)splash10-00ou-9000000000-ad3de6e6bc5dc675f293View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0900000000-80506768aa9d594be0c6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-4900000000-e9ac05a7cafb49b272acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9100000000-b4faa4cd8c9b56b4113dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-0900000000-3b5890274a618a3778b5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fk9-0900000000-86dcd0e893c03155a7b0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-9200000000-0f20f53f84cb306f481eView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    details
    UrineDetected and Quantified0.65 +/- 0.65 umol/mmol creatinineChildren (1-13 years old)BothNormal details
    UrineDetected and Quantified0.657 +/- 0.657 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
    details
    UrineDetected and Quantified0.657 +/- 0.657 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
    details
    UrineDetected and Quantified1.970 +/- 3.283 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
    details
    UrineDetected and Quantified11.163 +/- 7.880 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
    details
    UrineDetected and Quantified4.597 +/- 3.283 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
    details
    UrineDetected and Quantified5.253 +/- 1.970 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Normal
    details
    Abnormal Concentrations
    BiofluidStatusValueAgeSexConditionReferenceDetails
    UrineDetected and Quantified4.597 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Medium Chain Acyl-CoA Dehydrogenase Deficiency
    details
    UrineDetected and Quantified5.253 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Medium Chain Acyl-CoA Dehydrogenase Deficiency
    details
    UrineDetected and Quantified13.133 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Medium Chain Acyl-CoA Dehydrogenase Deficiency
    details
    UrineDetected and Quantified37.429 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Medium Chain Acyl-CoA Dehydrogenase Deficiency
    details
    UrineDetected and Quantified127.389 umol/mmol creatinineChildren (1 - 13 years old)Not Specified
    Medium Chain Acyl-CoA Dehydrogenase Deficiency
    details
    UrineDetected and Quantified45.902-261.960 umol/mmol creatinineChildren (1-13 years old)Not SpecifiedMedium Chain Acyl-CoA Dehydrogenase Deficiency details
    Associated Disorders and Diseases
    Disease References
    Medium Chain Acyl-CoA Dehydrogenase Deficiency
    1. Tserng KY, Jin SJ, Kerr DS, Hoppel CL: Abnormal urinary excretion of unsaturated dicarboxylic acids in patients with medium-chain acyl-CoA dehydrogenase deficiency. J Lipid Res. 1990 May;31(5):763-71. [PubMed:2380628 ]
    2. Duran M, De Klerk JB, Wadman SK, Bruinvis L, Ketting D: The differential diagnosis of dicarboxylic aciduria. J Inherit Metab Dis. 1984;7 Suppl 1:48-51. [PubMed:6434845 ]
    Associated OMIM IDs
    • 201450 (Medium Chain Acyl-CoA Dehydrogenase Deficiency)
    DrugBank IDNot Available
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound IDNot Available
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB023569
    KNApSAcK IDNot Available
    Chemspider ID9979870
    KEGG Compound IDNot Available
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkNot Available
    METLIN ID7235
    PubChem Compound11805205
    PDB IDNot Available
    ChEBI IDNot Available
    References
    Synthesis ReferenceBarco, A.; Benetti, S.; Pollini, G. P.; Taddia, R. Synthesis of cis-4-octene-1,8-dioic acid and its esters. Organic Preparations and Procedures International (1974), 6(5), 217-20.
    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 ]