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Human Metabolome Database Version 3.5

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Showing metabocard for Glutaconic acid (HMDB00620)

Record Information
Version 3.5
Creation Date 2005-11-16 08:48:42 -0700
Update Date 2013-02-08 17:08:57 -0700
HMDB ID HMDB00620
Secondary Accession Numbers
  • HMDB01657
Metabolite Identification
Common Name Glutaconic acid
Description Glutaconic 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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
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 Formula C5H6O4
Average Molecular Weight 130.0987
Monoisotopic Molecular Weight 130.02660868
IUPAC Name (2E)-pent-2-enedioic acid
Traditional IUPAC Name glutaconic acid
CAS Registry Number 1724-02-3
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 Key XVOUMQNXTGKGMA-OWOJBTEDSA-N
Chemical Taxonomy
Kingdom Organic Compounds
Super Class Lipids
Class Fatty Acids and Conjugates
Sub Class Unsaturated Fatty Acids
Other Descriptors
  • Aliphatic Acyclic Compounds
  • Dicarboxylic Acids and Derivatives
  • Organic Compounds
  • pentenedioic acid(ChEBI)
Substituents
  • Acyclic Alkene
  • Allyl Alcohol
  • Carboxylic Acid
  • Enone
Direct Parent Unsaturated Fatty Acids
Ontology
Status Detected 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
State Solid
Experimental Properties
Property Value Reference
Melting Point 133 - 135 °C Not Available
Boiling Point Not Available Not Available
Water Solubility Not Available Not Available
LogP Not Available Not Available
Predicted Properties
Property Value Source
Water Solubility 17.6 g/L ALOGPS
LogP 0.05 ALOGPS
LogP 0.044 ChemAxon
LogS -0.87 ALOGPS
pKa (strongest acidic) 3.69 ChemAxon
Hydrogen Acceptor Count 4 ChemAxon
Hydrogen Donor Count 2 ChemAxon
Polar Surface Area 74.6 A2 ChemAxon
Rotatable Bond Count 3 ChemAxon
Refractivity 29.23 ChemAxon
Polarizability 11.36 ChemAxon
Formal Charge 0 ChemAxon
Physiological Charge -2 ChemAxon
Spectra
Gas-MS Spectrum
1H NMR Spectrum
MS/MS Spectrum Quattro_QQQ 10
MS/MS Spectrum Quattro_QQQ 25
MS/MS Spectrum Quattro_QQQ 40
[1H,13C] 2D NMR Spectrum
Biological Properties
Cellular Locations
  • Extracellular
  • Membrane
Biofluid Locations
  • Urine
Tissue Location Not Available
Pathways Not Available
Normal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected and Quantified
3.1 (1.2-3.1) umol/mmol creatinine Adult (>18 years old) Both Comment Normal
  • Bouatra, S. ...
Urine Detected and Quantified
1.0 (0.0-2.0) umol/mmol creatinine Adult (>18 years old) Both Normal
Abnormal Concentrations
Biofluid Status Value Age Sex Condition Reference
Urine Detected and Quantified 180.0 (0.00-360.0) umol/mmol creatinine Adult (>18 years old) Both Glutaric aciduria I
Associated Disorders and Diseases
Disease References
Glutaric aciduria type 1
      Associated OMIM IDs
      • 231670 Link_out (Glutaric aciduria type 1)
      DrugBank ID Not Available
      DrugBank Metabolite ID Not Available
      Phenol Explorer Compound ID Not Available
      Phenol Explorer Metabolite ID Not Available
      FoodDB ID FDB022146
      KNApSAcK ID Not Available
      Chemspider ID 4444138 Link_out
      KEGG Compound ID C02214 Link_out
      BioCyc ID GLUTACONATE Link_out
      BiGG ID Not Available
      Wikipedia Link Glutaconic acid Link_out
      NuGOwiki Link HMDB00620 Link_out
      Metagene Link HMDB00620 Link_out
      METLIN ID 5593 Link_out
      PubChem Compound 5280498 Link_out
      PDB ID Not Available
      ChEBI ID 15670 Link_out
      References
      Synthesis Reference Schwarz, 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 Link_out
      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 Link_out