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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-02-23 10:36:27 UTC
Update Date2019-07-23 05:45:08 UTC
HMDB IDHMDB0001865
Secondary Accession Numbers
  • HMDB01865
Metabolite Identification
Common Name2-Oxovaleric acid
Description2-Oxovaleric acid is an alpha-ketoacid is a metabolite usually found in human biofluids. Ketoacids have been known to play an important part in the metabolism of valine, leucine, isoleucine. 2-Oxovaleric acid presence has been determined in human blood serum and urine in numerous scientific documents, although its origin remains unclear. (PMID: 11482739 , 9869358 , 3235498 ).
Structure
Data?1563860708
Synonyms
ValueSource
2-Ketopentanoic acidChEBI
2-OxovalerateChEBI
alpha-Ketovaleric acidChEBI
2-OxopentanoateKegg
2-KetopentanoateGenerator
a-KetovalerateGenerator
a-Ketovaleric acidGenerator
alpha-KetovalerateGenerator
Α-ketovalerateGenerator
Α-ketovaleric acidGenerator
2-Oxopentanoic acidGenerator
.alpha.-keto-N-valeric acidHMDB
2-Keto valeric acidHMDB
2-Keto-N-valeric acidHMDB
2-Ketovaleric acidHMDB
2-oxo-N-Valeric acidHMDB
2-oxo-PentanoateHMDB
2-oxo-Pentanoic acidHMDB
2-oxo-Valeric acidHMDB
a-Keto-valeric acidHMDB
a-oxo-N-Valeric acidHMDB
a-OxopentanoateHMDB
a-Oxopentanoic acidHMDB
a-Oxovaleric acidHMDB
alpha-Keto-valeric acidHMDB
alpha-oxo-N-Valeric acidHMDB
alpha-OxopentanoateHMDB
alpha-Oxopentanoic acidHMDB
alpha-Oxovaleric acidHMDB
2-Ketopentanoic acid, sodium saltHMDB
2-KetovalerateHMDB
2-Oxovaleric acidChEBI
2-Keto valerateGenerator
Chemical FormulaC5H8O3
Average Molecular Weight116.1152
Monoisotopic Molecular Weight116.047344122
IUPAC Name2-oxopentanoic acid
Traditional Nameα-oxopentanoic acid
CAS Registry Number1821-02-9
SMILES
CCCC(=O)C(O)=O
InChI Identifier
InChI=1S/C5H8O3/c1-2-3-4(6)5(7)8/h2-3H2,1H3,(H,7,8)
InChI KeyKDVFRMMRZOCFLS-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassKeto acids and derivatives
Sub ClassShort-chain keto acids and derivatives
Direct ParentShort-chain keto acids and derivatives
Alternative Parents
Substituents
  • Branched fatty acid
  • Methyl-branched fatty acid
  • Short-chain keto acid
  • Alpha-keto acid
  • Fatty acyl
  • Alpha-hydroxy ketone
  • Ketone
  • Carboxylic acid derivative
  • Carboxylic acid
  • Monocarboxylic acid or derivatives
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Organooxygen compound
  • Organic oxide
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Biological location:

Source:

Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting Point6.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.35Not Available
Predicted Properties
PropertyValueSource
Water Solubility32.7 g/LALOGPS
logP0.48ALOGPS
logP1.21ChemAxon
logS-0.55ALOGPS
pKa (Strongest Acidic)3.38ChemAxon
pKa (Strongest Basic)-9.7ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area54.37 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.22 m³·mol⁻¹ChemAxon
Polarizability11.19 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9300000000-96a7ebfdbd404be36517JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9810000000-cc08c7d71aba07e3e65dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9300000000-96a7ebfdbd404be36517JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9810000000-cc08c7d71aba07e3e65dJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-5920000000-f8deef57fbffab1b3d2bJSpectraViewer | MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9300000000-94bb5035832a9e9d4c6fJSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0096-9000000000-c76e9cdf847d8c82b9a1JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9200000000-d0413680f3a4b68185deJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0900000000-7c7943d1e8d06f13ee5cJSpectraViewer | MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-7c7943d1e8d06f13ee5cJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ba-9400000000-4f8f69aa2a633140f460JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007p-9100000000-97de63a0bf69f3b4c92aJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-caa12f5aa38fccf4e80bJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-6900000000-8e2f6f86655f562806deJSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-9200000000-87060e9d05b7a467cd68JSpectraViewer | MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-4f1165fe6fa8ada623a1JSpectraViewer | MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodDetected and Quantified12.9 +/- 2.0 uMAdult (>18 years old)BothNormal
    • Geigy Scientific ...
    • West Cadwell, N.J...
    • Basel, Switzerlan...
details
UrineDetected and Quantified0.45 +/- 0.02 umol/mmol creatinineAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003366
KNApSAcK IDNot Available
Chemspider ID67142
KEGG Compound IDC06255
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound74563
PDB IDNot Available
ChEBI ID33033
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceLieberman, Irving; Barker, H. A. b-Keto acid formation and decomposition by preparations of Clostridium kluyveri. Journal of Bacteriology (1954), 68 329-33.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Fu X, Kimura M, Iga M, Yamaguchi S: Gas chromatographic-mass spectrometric screening for organic acidemias using dried urine filter paper: determination of alpha-ketoacids. J Chromatogr B Biomed Sci Appl. 2001 Jul 5;758(1):87-94. [PubMed:11482739 ]
  2. Lee SH, Kim SO, Chung BC: Gas chromatographic-mass spectrometric determination of urinary oxoacids using O-(2,3,4,5,6-pentafluorobenzyl)oxime-trimethylsilyl ester derivatization and cation-exchange chromatography. J Chromatogr B Biomed Sci Appl. 1998 Nov 20;719(1-2):1-7. [PubMed:9869358 ]
  3. Wang ZJ, Zaitsu K, Ohkura Y: High-performance liquid chromatographic determination of alpha-keto acids in human serum and urine using 1,2-diamino-4,5-methylenedioxybenzene as a precolumn fluorescence derivatization reagent. J Chromatogr. 1988 Sep 9;430(2):223-31. [PubMed:3235498 ]