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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2015-03-09 23:54:09 UTC
HMDB IDHMDB00620
Secondary Accession Numbers
  • 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
  1. (E)-2-Pentenedioate
  2. (E)-2-Pentenedioic acid
  3. (E)-Glutaconate
  4. (E)-Glutaconic acid
  5. 1,3-Propenedicarboxylate
  6. 1,3-Propenedicarboxylic acid
  7. 1-Propene-1,3-dicarboxylate
  8. 1-Propene-1,3-dicarboxylic acid
  9. Glutaconic acid
  10. Pentenedioate
  11. Pentenedioic acid
  12. trans-Glutaconate
  13. trans-Glutaconic acid
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
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
  • Food
Biofunction
  • Cell signaling
  • Fuel and energy storage
  • Fuel or energy source
  • Membrane integrity/stability
Application
  • Nutrients
  • Stabilizers
  • Surfactants and Emulsifiers
Cellular locations
  • Extracellular
  • Membrane
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity29.23 m3·mol-1ChemAxon
Polarizability11.36 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraMS/MS1D NMR2D NMR
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
UrineDetected and Quantified3.1 (1.2-3.1) umol/mmol creatinineAdult (>18 years old)Both
Normal
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
  1. MetaGene [Link]
  2. MetaGene [Link]
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
NuGOwiki LinkHMDB00620
Metagene LinkHMDB00620
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. [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. [8214331 ]