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Record Information
Version4.0
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-09-27 07:46:20 UTC
HMDB IDHMDB0000620
Secondary Accession Numbers
  • HMDB00620
  • HMDB01657
Metabolite Identification
Common NameGlutaconic acid
DescriptionGlutaconic acid is an organic compound with general formula C5H6O4. The compound is a dicarboxylic acid and related with the fully saturated glutaric acid.
Structure
Thumb
Synonyms
ValueSource
(e)-GlutaconateChEBI
trans-GlutaconateChEBI
trans-Glutaconic acidChEBI
(e)-Glutaconic acidGenerator
GlutaconateGenerator
(e)-2-PentenedioateHMDB
(e)-2-Pentenedioic acidHMDB
1,3-PropenedicarboxylateHMDB
1,3-Propenedicarboxylic acidHMDB
1-Propene-1,3-dicarboxylateHMDB
1-Propene-1,3-dicarboxylic acidHMDB
PentenedioateHMDB
Pentenedioic acidHMDB
Glutaconic acid, ion(2-)MeSH
Glutaconic acid, copper saltMeSH
Glutaconic acid, (e)-isomerMeSH
Chemical FormulaC5H6O4
Average Molecular Weight130.0987
Monoisotopic Molecular Weight130.02660868
IUPAC Name(2E)-pent-2-enedioic acid
Traditional Nameglutaconic acid
CAS Registry Number1724-02-3
SMILES
OC(=O)C\C=C\C(O)=O
InChI Identifier
InChI=1S/C5H6O4/c6-4(7)2-1-3-5(8)9/h1-2H,3H2,(H,6,7)(H,8,9)/b2-1+
InChI KeyXVOUMQNXTGKGMA-OWOJBTEDSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Carboxylic acid
  • 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:

Source:

Process

Naturally occurring process:

  Biological process:

    Cellular process:

Role

Indirect biological role:

Industrial application:

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point133 - 135 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility17.6 g/LALOGPS
logP0.05ALOGPS
logP0.044ChemAxon
logS-0.87ALOGPS
pKa (Strongest Acidic)3.69ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area74.6 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity29.23 m³·mol⁻¹ChemAxon
Polarizability11.36 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-3930000000-d1b6e04bed9f3de84afaView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0002-3910000000-02c8fdec1f78bd5117e2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-001r-9100000000-42f59aea4f8e6bb8ab57View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-05g0-8920000000-733f5a9f839df29bff69View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Negative (Annotated)splash10-000i-9000000000-6fb6cc9ab31410b273f1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Negative (Annotated)splash10-000f-9000000000-b9c27f4002ce9f12f916View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Negative (Annotated)splash10-000f-9100000000-d627e3ddfe858b1b331dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03e9-3900000000-f982ee0bd6ebcaf33bbeView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-01q0-9500000000-90dd8c522781e5da5ebbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00n0-9000000000-e56400244a361d348a1fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1900000000-ad86855e24f296413178View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-4900000000-30e4a1adead132f7de92View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-052f-9000000000-47a3aa8cf8913cc4d70eView in MoNA
1D NMR1H NMR SpectrumNot AvailableView in JSpectraViewer
2D NMR[1H,13C] 2D NMR SpectrumNot AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified3.1 (1.2-3.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
details
UrineDetected and Quantified0.0 umol/mmol creatinineChildren (1 - 18 years old)Both
Normal
    • BC Children's Hos...
details
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified1.0 (0.0-2.0) umol/mmol creatinineAdult (>18 years old)BothGlutaric aciduria type 1 details
UrineDetected and Quantified180.0 (0.00-360.0) umol/mmol creatinineChildren (1-13 years old)BothGlutaric aciduria I details
Associated Disorders and Diseases
Disease References
Glutaric aciduria type 1
    MetaGeneMetaGene
Associated OMIM IDs
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022146
KNApSAcK IDNot Available
Chemspider ID4444138
KEGG Compound IDC02214
BioCyc IDGLUTACONATE
BiGG IDNot Available
Wikipedia LinkGlutaconic acid
METLIN ID5593
PubChem Compound5280498
PDB IDNot Available
ChEBI ID15670
References
Synthesis ReferenceSchwarz, Siegfried; Bohn, Helmut; Schmidt, Dieter; Kulpa, Manfred; Spakowski, Horst; Becker, Manfred. Glutaconic acid. Ger. (East) (1967), 2 pp.
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. Podebrad F, Heil M, Beck T, Mosandl A, Sewell AC, Bohles H: Stereodifferentiation of 3-hydroxyisobutyric- and 3-aminoisobutyric acid in human urine by enantioselective multidimensional capillary gas chromatography-mass spectrometry. Clin Chim Acta. 2000 Feb 25;292(1-2):93-105. [PubMed:10686279 ]
  2. Osaka H, Kimura S, Nezu A, Yamazaki S, Saitoh K, Yamaguchi S: Chronic subdural hematoma, as an initial manifestation of glutaric aciduria type-1. Brain Dev. 1993 Mar-Apr;15(2):125-7. [PubMed:8214331 ]