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Record Information
Version3.6
Creation Date2006-02-23 10:36:27 UTC
Update Date2016-02-11 01:05:02 UTC
HMDB IDHMDB01865
Secondary Accession NumbersNone
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
Thumb
Synonyms
ValueSource
2-Ketopentanoic acidChEBI
2-OxovalerateChEBI
2-Oxovaleric acidChEBI
alpha-Ketovaleric acidChEBI
2-KetopentanoateGenerator
2-OxopentanoateGenerator
a-KetovalerateGenerator
a-Ketovaleric acidGenerator
alpha-KetovalerateGenerator
α-ketovalerateGenerator
α-ketovaleric 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
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 KeyInChIKey=KDVFRMMRZOCFLS-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
  • Methyl-branched fatty acid
  • Short-chain keto acid
  • Branched fatty acid
  • Fatty acyl
  • Alpha-keto acid
  • Alpha-hydroxy ketone
  • Ketone
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
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 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity27.22 m3·mol-1ChemAxon
Polarizability11.19 Å3ChemAxon
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-MS (1 MEOX; 1 TMS)splash10-000i-9300000000-96a7ebfdbd404be36517View in MoNA
GC-MSGC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)splash10-000i-9810000000-cc08c7d71aba07e3e65dView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0900000000-7c7943d1e8d06f13ee5cView in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
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
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB003366
KNApSAcK IDNot Available
Chemspider ID67142
KEGG Compound IDC06255
BioCyc IDCPD-3618
BiGG IDNot Available
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01865
Metagene LinkHMDB01865
METLIN IDNot Available
PubChem Compound74563
PDB IDNot Available
ChEBI ID33033
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. 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. [9869358 ]
  2. 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. [11482739 ]
  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. [3235498 ]