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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-02-23 10:36:27 UTC

Update Date

2023-02-21 17:15:52 UTC

HMDB ID

HMDB0001865

Secondary Accession Numbers

HMDB01865

Metabolite Identification

Common Name

2-Oxovaleric acid

Description

2-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

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

View in JSmol View NMR Assignments View Stereo Labels

Synonyms

Value	Source
2-Ketopentanoic acid	ChEBI
2-Oxovalerate	ChEBI
alpha-Ketovaleric acid	ChEBI
2-Oxopentanoate	Kegg
2-Ketopentanoate	Generator
a-Ketovalerate	Generator
a-Ketovaleric acid	Generator
alpha-Ketovalerate	Generator
Α-ketovalerate	Generator
Α-ketovaleric acid	Generator
2-Oxopentanoic acid	Generator
.alpha.-keto-N-valeric acid	HMDB
2-keto Valeric acid	HMDB
2-keto-N-Valeric acid	HMDB
2-Ketovaleric acid	HMDB
2-oxo-N-Valeric acid	HMDB
2-oxo-Pentanoate	HMDB
2-oxo-Pentanoic acid	HMDB
2-oxo-Valeric acid	HMDB
a-keto-Valeric acid	HMDB
a-oxo-N-Valeric acid	HMDB
a-Oxopentanoate	HMDB
a-Oxopentanoic acid	HMDB
a-Oxovaleric acid	HMDB
alpha-keto-Valeric acid	HMDB
alpha-oxo-N-Valeric acid	HMDB
alpha-Oxopentanoate	HMDB
alpha-Oxopentanoic acid	HMDB
alpha-Oxovaleric acid	HMDB
2-Ketopentanoic acid, sodium salt	MeSH, HMDB
2-Ketovalerate	MeSH, HMDB
2-Oxovaleric acid	ChEBI
2-Keto valerate	Generator, HMDB

Chemical Formula

C₅H₈O₃

Average Molecular Weight

116.1152

Monoisotopic Molecular Weight

116.047344122

IUPAC Name

2-oxopentanoic acid

Traditional Name

α-oxopentanoic acid

CAS Registry Number

1821-02-9

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 Key

KDVFRMMRZOCFLS-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.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Short-chain keto acids and derivatives

Direct Parent

Short-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 Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:33033 )
oxopentanoic acid (CHEBI:33033 )
Oxo fatty acids (C06255 )
Oxo fatty acids (LMFA01060004 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (HMDB: HMDB0001865)

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0001865)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0001865)

Source

Endogenous

Endogenous (HMDB: HMDB0001865)

Plant

Plant (HMDB: HMDB0001865)

Exogenous

Food

Food (HMDB: HMDB0001865)

Animal origin

Poultry

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Not Available

Role

Not Available

Physical Properties

State

Liquid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	6.5 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	0.35	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	32.7 g/L	ALOGPS
logP	0.48	ALOGPS
logP	1.21	ChemAxon
logS	-0.55	ALOGPS
pKa (Strongest Acidic)	3.38	ChemAxon
pKa (Strongest Basic)	-9.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	27.22 m³·mol⁻¹	ChemAxon
Polarizability	11.19 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	124.422	31661259
DarkChem	[M-H]-	119.699	31661259
AllCCS	[M+H]+	128.417	32859911
AllCCS	[M-H]-	125.217	32859911
DeepCCS	[M+H]+	126.629	30932474
DeepCCS	[M-H]-	123.827	30932474
DeepCCS	[M-2H]-	160.143	30932474
DeepCCS	[M+Na]+	134.783	30932474
AllCCS	[M+H]+	128.4	32859911
AllCCS	[M+H-H2O]+	124.1	32859911
AllCCS	[M+NH4]+	132.4	32859911
AllCCS	[M+Na]+	133.6	32859911
AllCCS	[M-H]-	125.2	32859911
AllCCS	[M+Na-2H]-	128.4	32859911
AllCCS	[M+HCOO]-	131.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Oxovaleric acid	CCCC(=O)C(O)=O	1780.4	Standard polar	33892256
2-Oxovaleric acid	CCCC(=O)C(O)=O	1339.7	Standard non polar	33892256
2-Oxovaleric acid	CCCC(=O)C(O)=O	945.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Oxovaleric acid,1TMS,isomer #1	CCCC(=O)C(=O)O[Si](C)(C)C	1093.9	Semi standard non polar	33892256
2-Oxovaleric acid,1TMS,isomer #2	CCC=C(O[Si](C)(C)C)C(=O)O	1195.9	Semi standard non polar	33892256
2-Oxovaleric acid,2TMS,isomer #1	CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1293.8	Semi standard non polar	33892256
2-Oxovaleric acid,2TMS,isomer #1	CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1209.9	Standard non polar	33892256
2-Oxovaleric acid,2TMS,isomer #1	CCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1253.8	Standard polar	33892256
2-Oxovaleric acid,1TBDMS,isomer #1	CCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C	1311.0	Semi standard non polar	33892256
2-Oxovaleric acid,1TBDMS,isomer #2	CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O	1433.2	Semi standard non polar	33892256
2-Oxovaleric acid,2TBDMS,isomer #1	CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1694.1	Semi standard non polar	33892256
2-Oxovaleric acid,2TBDMS,isomer #1	CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1609.4	Standard non polar	33892256
2-Oxovaleric acid,2TBDMS,isomer #1	CCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1589.0	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Oxovaleric acid GC-MS (1 MEOX; 1 TMS)	splash10-000i-9300000000-96a7ebfdbd404be36517	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Oxovaleric acid GC-MS (1 MEOX; 1 TMS)	splash10-000i-9810000000-cc08c7d71aba07e3e65d	2014-06-16	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Oxovaleric acid GC-MS (Non-derivatized)	splash10-000i-9300000000-96a7ebfdbd404be36517	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Oxovaleric acid GC-MS (Non-derivatized)	splash10-000i-9810000000-cc08c7d71aba07e3e65d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Oxovaleric acid GC-EI-TOF (Non-derivatized)	splash10-0f79-5920000000-f8deef57fbffab1b3d2b	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Oxovaleric acid GC-EI-TOF (Non-derivatized)	splash10-000i-9300000000-94bb5035832a9e9d4c6f	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Oxovaleric acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0096-9000000000-c76e9cdf847d8c82b9a1	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Oxovaleric acid GC-MS (1 TMS) - 70eV, Positive	splash10-00di-9200000000-d0413680f3a4b68185de	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Oxovaleric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Oxovaleric acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Oxovaleric acid LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negative-QTOF	splash10-014i-0900000000-7c7943d1e8d06f13ee5c	2012-08-31	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Oxovaleric acid LC-ESI-QTOF , negative-QTOF	splash10-014i-0900000000-7c7943d1e8d06f13ee5c	2017-09-14	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxovaleric acid 10V, Positive-QTOF	splash10-01ba-9400000000-4f8f69aa2a633140f460	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxovaleric acid 20V, Positive-QTOF	splash10-007p-9100000000-97de63a0bf69f3b4c92a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxovaleric acid 40V, Positive-QTOF	splash10-0006-9000000000-caa12f5aa38fccf4e80b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxovaleric acid 10V, Negative-QTOF	splash10-014i-6900000000-8e2f6f86655f562806de	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxovaleric acid 20V, Negative-QTOF	splash10-01ba-9200000000-87060e9d05b7a467cd68	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxovaleric acid 40V, Negative-QTOF	splash10-0006-9000000000-4f1165fe6fa8ada623a1	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxovaleric acid 10V, Positive-QTOF	splash10-006x-9000000000-5d9ee9dd00b39a9fbf08	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxovaleric acid 20V, Positive-QTOF	splash10-0006-9000000000-6616ded1418d6de0a7d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxovaleric acid 40V, Positive-QTOF	splash10-0006-9000000000-dd6f23591b3e1df18117	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxovaleric acid 10V, Negative-QTOF	splash10-014i-1900000000-c7997cbb01c80cfa3e43	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxovaleric acid 20V, Negative-QTOF	splash10-014i-9000000000-36ceafbef1e054585185	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Oxovaleric acid 40V, Negative-QTOF	splash10-0006-9000000000-02c6d2915b5749846b62	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-16	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-03	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-03	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	12.9 +/- 2.0 uM	Adult (>18 years old)	Both	Normal	Geigy Scientific ... West Cadwell, N.J... Basel, Switzerlan...	details
Urine	Detected and Quantified	0-300 umol/mmol creatinine	Newborn (0-30 days old)	Both	Normal	31506554	details
Urine	Detected and Quantified	0.45 +/- 0.02 umol/mmol creatinine	Adult (>18 years old)	Not Specified	Normal	9869358	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

74563

PDB ID

Not Available

ChEBI ID

33033

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Lieberman, 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

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 ]
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 ]
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 ]

Showing metabocard for 2-Oxovaleric acid (HMDB0001865)

MOL for HMDB0001865 (2-Oxovaleric acid)

3D MOL for HMDB0001865 (2-Oxovaleric acid)

3D SDF for HMDB0001865 (2-Oxovaleric acid)

3D-SDF for HMDB0001865 (2-Oxovaleric acid)

PDB for HMDB0001865 (2-Oxovaleric acid)

3D PDB for HMDB0001865 (2-Oxovaleric acid)

SMILES for HMDB0001865 (2-Oxovaleric acid)

INCHI for HMDB0001865 (2-Oxovaleric acid)

Structure for HMDB0001865 (2-Oxovaleric acid)

3D Structure for HMDB0001865 (2-Oxovaleric acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra