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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2006-02-23 10:36:27 UTC
Update Date2017-12-07 01:46:15 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
Thumb
Synonyms
ValueSource
2-Ketopentanoic acidChEBI
2-OxovalerateChEBI
alpha-Ketovaleric acidChEBI
2-KetopentanoateGenerator
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
2-OxopentanoateHMDB
2-Oxopentanoic 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 saltMeSH
2-KetovalerateMeSH
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
DescriptionThis compound belongs to the class of chemical entities known as short-chain keto acids and derivatives. These are keto acids with an alkyl chain the contains less than 6 carbon atoms.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassKeto 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

Biological Location:

  Biofluid and excreta:

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
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
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9300000000-96a7ebfdbd404be36517View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-000i-9810000000-cc08c7d71aba07e3e65dView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0f79-5920000000-f8deef57fbffab1b3d2bView in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-000i-9300000000-94bb5035832a9e9d4c6fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0096-9000000000-c76e9cdf847d8c82b9a1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9200000000-d0413680f3a4b68185deView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-014i-0900000000-7c7943d1e8d06f13ee5cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-014i-0900000000-7c7943d1e8d06f13ee5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-01ba-9400000000-4f8f69aa2a633140f460View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-007p-9100000000-97de63a0bf69f3b4c92aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-caa12f5aa38fccf4e80bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-014i-6900000000-8e2f6f86655f562806deView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01ba-9200000000-87060e9d05b7a467cd68View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-4f1165fe6fa8ada623a1View in MoNA
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
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. [PubMed: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. [PubMed: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. [PubMed:3235498 ]