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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2006-02-23 10:34:24 UTC

Update Date

2023-02-21 17:15:52 UTC

HMDB ID

HMDB0001864

Secondary Accession Numbers

HMDB01864

Metabolite Identification

Common Name

2-Ketohexanoic acid

Description

2-Ketohexanoic acid, also known as alpha-ketocaproic acid or 2-oxohexanoate, belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain. 2-Ketohexanoic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 2-ketohexanoic acid a potential biomarker for the consumption of these foods. 2-Ketohexanoic 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 small amount of articles have been published on 2-Ketohexanoic 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-Keto-N-caproic acid	ChEBI
2-oxo 6:0	ChEBI
2-oxo C6:0	ChEBI
2-Oxohexanoate	ChEBI
alpha-Ketocaproic acid	ChEBI
alpha-Ketohexanoic acid	ChEBI
2-Keto-N-caproate	Generator
2-Oxohexanoic acid	Generator
a-Ketocaproate	Generator
a-Ketocaproic acid	Generator
alpha-Ketocaproate	Generator
Α-ketocaproate	Generator
Α-ketocaproic acid	Generator
a-Ketohexanoate	Generator
a-Ketohexanoic acid	Generator
alpha-Ketohexanoate	Generator
Α-ketohexanoate	Generator
Α-ketohexanoic acid	Generator
2-Ketohexanoate	Generator
2-Ketocaproate	MeSH
alpha-Ketocaproic acid, sodium salt	MeSH
2-Ketocaproic acid	HMDB
2-oxo-Hexanoate	HMDB
2-oxo-Hexanoic acid	HMDB
2-Ketohexanoic acid	ChEBI

Chemical Formula

C₆H₁₀O₃

Average Molecular Weight

130.1418

Monoisotopic Molecular Weight

130.062994186

IUPAC Name

2-oxohexanoic acid

Traditional Name

2-oxohexanoic acid

CAS Registry Number

2492-75-3

SMILES

CCCCC(=O)C(O)=O

InChI Identifier

InChI=1S/C6H10O3/c1-2-3-4-5(7)6(8)9/h2-4H2,1H3,(H,8,9)

InChI Key

XNIHZNNZJHYHLC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as medium-chain keto acids and derivatives. These are keto acids with a 6 to 12 carbon atoms long side chain.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Keto acids and derivatives

Sub Class

Medium-chain keto acids and derivatives

Direct Parent

Medium-chain keto acids and derivatives

Alternative Parents

Substituents

Medium-chain keto acid
Alpha-keto acid
Alpha-hydroxy ketone
Ketone
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

2-oxo monocarboxylic acid (CHEBI:17308 )
medium-chain fatty acid (CHEBI:17308 )
straight-chain fatty acid (CHEBI:17308 )
oxo fatty acid (CHEBI:17308 )
Oxo fatty acids (C00902 )
Oxo fatty acids (LMFA01060007 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Saliva (HMDB: HMDB0001864)

Source

Endogenous

Endogenous (HMDB: HMDB0001864)

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)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	198.70 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	145000 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	0.350 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	8.02 g/L	ALOGPS
logP	0.94	ALOGPS
logP	1.66	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	3.53	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	4	ChemAxon
Refractivity	31.82 m³·mol⁻¹	ChemAxon
Polarizability	13.19 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]+	129.07	31661259
DarkChem	[M-H]-	125.347	31661259
AllCCS	[M+H]+	131.264	32859911
AllCCS	[M-H]-	128.436	32859911
DeepCCS	[M+H]+	132.045	30932474
DeepCCS	[M-H]-	129.28	30932474
DeepCCS	[M-2H]-	165.743	30932474
DeepCCS	[M+Na]+	140.531	30932474
AllCCS	[M+H]+	131.3	32859911
AllCCS	[M+H-H2O]+	127.1	32859911
AllCCS	[M+NH4]+	135.2	32859911
AllCCS	[M+Na]+	136.3	32859911
AllCCS	[M-H]-	128.4	32859911
AllCCS	[M+Na-2H]-	131.1	32859911
AllCCS	[M+HCOO]-	134.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
2-Ketohexanoic acid	CCCCC(=O)C(O)=O	1894.2	Standard polar	33892256
2-Ketohexanoic acid	CCCCC(=O)C(O)=O	1382.6	Standard non polar	33892256
2-Ketohexanoic acid	CCCCC(=O)C(O)=O	1046.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
2-Ketohexanoic acid,1TMS,isomer #1	CCCCC(=O)C(=O)O[Si](C)(C)C	1169.3	Semi standard non polar	33892256
2-Ketohexanoic acid,1TMS,isomer #2	CCCC=C(O[Si](C)(C)C)C(=O)O	1273.3	Semi standard non polar	33892256
2-Ketohexanoic acid,2TMS,isomer #1	CCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1331.0	Semi standard non polar	33892256
2-Ketohexanoic acid,2TMS,isomer #1	CCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1277.7	Standard non polar	33892256
2-Ketohexanoic acid,2TMS,isomer #1	CCCC=C(O[Si](C)(C)C)C(=O)O[Si](C)(C)C	1337.9	Standard polar	33892256
2-Ketohexanoic acid,1TBDMS,isomer #1	CCCCC(=O)C(=O)O[Si](C)(C)C(C)(C)C	1392.6	Semi standard non polar	33892256
2-Ketohexanoic acid,1TBDMS,isomer #2	CCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O	1513.1	Semi standard non polar	33892256
2-Ketohexanoic acid,2TBDMS,isomer #1	CCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1773.3	Semi standard non polar	33892256
2-Ketohexanoic acid,2TBDMS,isomer #1	CCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1663.6	Standard non polar	33892256
2-Ketohexanoic acid,2TBDMS,isomer #1	CCCC=C(O[Si](C)(C)C(C)(C)C)C(=O)O[Si](C)(C)C(C)(C)C	1668.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - 2-Ketohexanoic acid GC-EI-TOF (Non-derivatized)	splash10-000j-8920000000-9e106a172aeaca6001ea	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - 2-Ketohexanoic acid GC-EI-TOF (Non-derivatized)	splash10-000j-8920000000-9e106a172aeaca6001ea	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ketohexanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-002f-9000000000-e0cebba0b69620390c09	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ketohexanoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-007a-9300000000-87b7d0f0e16ba9e212cb	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 2-Ketohexanoic 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-Ketohexanoic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-01p9-9500000000-5145cab306a85b6e9d7f	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Ketohexanoic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-014i-9000000000-4cd8f41133a4d23b1d4c	2012-07-24	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - 2-Ketohexanoic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-01qj-9100000000-caf6abf28104b7765cef	2012-07-24	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 10V, Positive-QTOF	splash10-01qi-4900000000-702612249f0615c78f6b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 20V, Positive-QTOF	splash10-0btm-9300000000-d02ff05157ccb2f8d416	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 40V, Positive-QTOF	splash10-0a4l-9000000000-dfcf44ed2c628b6b914a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 10V, Negative-QTOF	splash10-004i-3900000000-d751dca8c7b118a0dea9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 20V, Negative-QTOF	splash10-01s9-9500000000-c04f00087e8e89956b26	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 40V, Negative-QTOF	splash10-0006-9000000000-4a26ce3589a801c4bcef	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 10V, Positive-QTOF	splash10-052u-9000000000-a1430045d6ae5d2e494c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 20V, Positive-QTOF	splash10-0a4l-9000000000-d6e0a51fd3a4a90d9ceb	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 40V, Positive-QTOF	splash10-0a4l-9000000000-ed2b82d47ad4721d3a01	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 10V, Negative-QTOF	splash10-004i-0900000000-8be0a8820bd022f7267b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 20V, Negative-QTOF	splash10-001i-9000000000-761b5c64b393cb442dcc	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 2-Ketohexanoic acid 40V, Negative-QTOF	splash10-066u-9000000000-1763f75b095d5d429e5b	2021-09-23	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Experimental 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	2012-12-04	Wishart Lab	View Spectrum
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
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	2012-12-05	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

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	Zerihun T. Dame, ...	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

FDB022718

KNApSAcK ID

Not Available

Chemspider ID

140384

KEGG Compound ID

C00902

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

4144

PubChem Compound

159664

PDB ID

Not Available

ChEBI ID

17308

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1620931

References

Synthesis Reference

Igarashi, Minoru; Midorikawa, Hiroshi. Synthesis of a-oxo acids from diethyl alkylidenemalonates. Journal of Organic Chemistry (1964), 29(7), 2080-2.

Material Safety Data Sheet (MSDS)

Download (PDF)

General References

Nakahara T, Ishida J, Yamaguchi M, Nakamura M: Determination of alpha-keto acids including phenylpyruvic acid in human plasma by high-performance liquid chromatography with chemiluminescence detection. Anal Biochem. 1990 Nov 1;190(2):309-13. [PubMed:2291475 ]
Shroads AL, Henderson GN, Cheung J, James MO, Stacpoole PW: Unified gas chromatographic-mass spectrometric method for quantitating tyrosine metabolites in urine and plasma. J Chromatogr B Analyt Technol Biomed Life Sci. 2004 Sep 5;808(2):153-61. [PubMed:15261808 ]
Lenzen S, Formanek H, Panten U: Signal function of metabolism of neutral amino acids and 2-keto acids for initiation of insulin secretion. J Biol Chem. 1982 Jun 25;257(12):6631-3. [PubMed:7045091 ]
Heissig H, Urban KA, Hastedt K, Zunkler BJ, Panten U: Mechanism of the insulin-releasing action of alpha-ketoisocaproate and related alpha-keto acid anions. Mol Pharmacol. 2005 Oct;68(4):1097-105. Epub 2005 Jul 13. [PubMed:16014804 ]

Showing metabocard for 2-Ketohexanoic acid (HMDB0001864)

MOL for HMDB0001864 (2-Ketohexanoic acid)

3D MOL for HMDB0001864 (2-Ketohexanoic acid)

3D SDF for HMDB0001864 (2-Ketohexanoic acid)

3D-SDF for HMDB0001864 (2-Ketohexanoic acid)

PDB for HMDB0001864 (2-Ketohexanoic acid)

3D PDB for HMDB0001864 (2-Ketohexanoic acid)

SMILES for HMDB0001864 (2-Ketohexanoic acid)

INCHI for HMDB0001864 (2-Ketohexanoic acid)

Structure for HMDB0001864 (2-Ketohexanoic acid)

3D Structure for HMDB0001864 (2-Ketohexanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra