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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2006-02-23 10:36:27 UTC
Update Date2020-02-27 20:30:07 UTC
HMDB IDHMDB0001865
Secondary Accession Numbers
  • HMDB01865
Metabolite Identification
Common Name2-Oxovaleric acid
Description2-Oxovaleric acid, also known as 2-oxovalerate or a-ketovalerate, 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. 2-Oxovaleric acid has been detected, but not quantified in, several different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), domestic pigs (Sus scrofa domestica), and herbs and spices. This could make 2-oxovaleric acid a potential biomarker for the consumption of these foods. 2-Oxovaleric acid is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on 2-Oxovaleric acid.
Structure
Data?1582752213
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 saltMeSH, HMDB
2-KetovalerateMeSH, HMDB
2-Oxovaleric acidChEBI
2-Keto valerateGenerator, HMDB
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

Biological location

Physical Properties
StateLiquid
Experimental Molecular Properties
PropertyValueReference
Melting Point6.5 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.35Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular 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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+124.42231661259
DarkChem[M-H]-119.69931661259
AllCCS[M+H]+128.41732859911
AllCCS[M-H]-125.21732859911
DeepCCS[M+H]+126.62930932474
DeepCCS[M-H]-123.82730932474
DeepCCS[M-2H]-160.14330932474
DeepCCS[M+Na]+134.78330932474
AllCCS[M+H]+128.432859911
AllCCS[M+H-H2O]+124.132859911
AllCCS[M+NH4]+132.432859911
AllCCS[M+Na]+133.632859911
AllCCS[M-H]-125.232859911
AllCCS[M+Na-2H]-128.432859911
AllCCS[M+HCOO]-131.932859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
2-Oxovaleric acidCCCC(=O)C(O)=O1780.4Standard polar33892256
2-Oxovaleric acidCCCC(=O)C(O)=O1339.7Standard non polar33892256
2-Oxovaleric acidCCCC(=O)C(O)=O945.3Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
2-Oxovaleric acid,1TMS,isomer #1CCCC(=O)C(=O)O[Si](C)(C)C1093.9Semi standard non polar33892256
2-Oxovaleric acid,1TMS,isomer #2CCC=C(O[Si](C)(C)C)C(=O)O1195.9Semi standard non polar33892256
2-Oxovaleric acid,2TMS,isomer #1CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1293.8Semi standard non polar33892256
2-Oxovaleric acid,2TMS,isomer #1CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1209.9Standard non polar33892256
2-Oxovaleric acid,2TMS,isomer #1CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C1253.8Standard polar33892256
2-Oxovaleric acid,1TBDMS,isomer #1CCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C1311.0Semi standard non polar33892256
2-Oxovaleric acid,1TBDMS,isomer #2CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O1433.2Semi standard non polar33892256
2-Oxovaleric acid,2TBDMS,isomer #1CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1694.1Semi standard non polar33892256
2-Oxovaleric acid,2TBDMS,isomer #1CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1609.4Standard non polar33892256
2-Oxovaleric acid,2TBDMS,isomer #1CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C1589.0Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - 2-Oxovaleric acid GC-MS (1 MEOX; 1 TMS)splash10-000i-9300000000-96a7ebfdbd404be365172014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Oxovaleric acid GC-MS (1 MEOX; 1 TMS)splash10-000i-9810000000-cc08c7d71aba07e3e65d2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Oxovaleric acid GC-MS (Non-derivatized)splash10-000i-9300000000-96a7ebfdbd404be365172017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Oxovaleric acid GC-MS (Non-derivatized)splash10-000i-9810000000-cc08c7d71aba07e3e65d2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Oxovaleric acid GC-EI-TOF (Non-derivatized)splash10-0f79-5920000000-f8deef57fbffab1b3d2b2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - 2-Oxovaleric acid GC-EI-TOF (Non-derivatized)splash10-000i-9300000000-94bb5035832a9e9d4c6f2017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Oxovaleric acid GC-MS (Non-derivatized) - 70eV, Positivesplash10-0096-9000000000-c76e9cdf847d8c82b9a12017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Oxovaleric acid GC-MS (1 TMS) - 70eV, Positivesplash10-00di-9200000000-d0413680f3a4b68185de2017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Oxovaleric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - 2-Oxovaleric acid GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxovaleric acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOFsplash10-014i-0900000000-7c7943d1e8d06f13ee5c2012-08-31HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - 2-Oxovaleric acid LC-ESI-QTOF , negative-QTOFsplash10-014i-0900000000-7c7943d1e8d06f13ee5c2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxovaleric acid 10V, Positive-QTOFsplash10-01ba-9400000000-4f8f69aa2a633140f4602017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxovaleric acid 20V, Positive-QTOFsplash10-007p-9100000000-97de63a0bf69f3b4c92a2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxovaleric acid 40V, Positive-QTOFsplash10-0006-9000000000-caa12f5aa38fccf4e80b2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxovaleric acid 10V, Negative-QTOFsplash10-014i-6900000000-8e2f6f86655f562806de2017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxovaleric acid 20V, Negative-QTOFsplash10-01ba-9200000000-87060e9d05b7a467cd682017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxovaleric acid 40V, Negative-QTOFsplash10-0006-9000000000-4f1165fe6fa8ada623a12017-09-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxovaleric acid 10V, Positive-QTOFsplash10-006x-9000000000-5d9ee9dd00b39a9fbf082021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxovaleric acid 20V, Positive-QTOFsplash10-0006-9000000000-6616ded1418d6de0a7d62021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxovaleric acid 40V, Positive-QTOFsplash10-0006-9000000000-dd6f23591b3e1df181172021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxovaleric acid 10V, Negative-QTOFsplash10-014i-1900000000-c7997cbb01c80cfa3e432021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxovaleric acid 20V, Negative-QTOFsplash10-014i-9000000000-36ceafbef1e0545851852021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 2-Oxovaleric acid 40V, Negative-QTOFsplash10-0006-9000000000-02c6d2915b5749846b622021-09-24Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16Wishart LabView Spectrum
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 Quantified0-300 umol/mmol creatinineNewborn (0-30 days old)Both
Normal
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
FooDB IDFDB003366
KNApSAcK IDC00055637
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
MarkerDB IDNot Available
Good Scents 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. 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 ]