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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2008-10-15 12:12:16 UTC

Update Date

2023-02-21 17:17:25 UTC

HMDB ID

HMDB0010717

Secondary Accession Numbers

HMDB10717

Metabolite Identification

Common Name

3-Oxohexanoic acid

Description

3-Oxohexanoic acid, also known as 3-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. 3-Oxohexanoic acid exists in all eukaryotes, ranging from yeast to plants to humans. In humans, 3-oxohexanoic acid is involved in the fatty acid biosynthesis pathway. 3-Oxohexanoic 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 3-oxohexanoic acid a potential biomarker for the consumption of these foods. 3-Oxohexanoic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on 3-Oxohexanoic 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
3-Oxohexanoate	ChEBI

Chemical Formula

C₆H₁₀O₃

Average Molecular Weight

130.1418

Monoisotopic Molecular Weight

130.062994186

IUPAC Name

3-oxohexanoic acid

Traditional Name

3-oxohexanoic acid

CAS Registry Number

4380-91-0

SMILES

CCCC(=O)CC(O)=O

InChI Identifier

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

InChI Key

BDCLDNALSPBWPQ-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
Beta-keto acid
1,3-dicarbonyl compound
Beta-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

3-oxo monocarboxylic acid (CHEBI:28422 )
Oxo fatty acids (C02122 )
Oxo fatty acids (LMFA01060008 )

Ontology

Not Available

Endogenous (HMDB: HMDB0010717)

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)
Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

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)

Equine

Horse (FooDB: FOOD00378)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Biosynthesis (PathBank: SMP0002360)
Fatty Acid Biosynthesis (PathBank: SMP0087409)
Fatty Acid Biosynthesis (HMDB: HMDB0010717)

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	33.9 g/L	ALOGPS
logP	0.43	ALOGPS
logP	1.14	ChemAxon
logS	-0.58	ALOGPS
pKa (Strongest Acidic)	4.37	ChemAxon
pKa (Strongest Basic)	-7.5	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	31.77 m³·mol⁻¹	ChemAxon
Polarizability	13.11 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]+	128.685	31661259
DarkChem	[M-H]-	124.766	31661259
DeepCCS	[M+H]+	130.603	30932474
DeepCCS	[M-H]-	127.749	30932474
DeepCCS	[M-2H]-	164.118	30932474
DeepCCS	[M+Na]+	139.187	30932474
AllCCS	[M+H]+	131.1	32859911
AllCCS	[M+H-H2O]+	126.9	32859911
AllCCS	[M+NH4]+	135.0	32859911
AllCCS	[M+Na]+	136.1	32859911
AllCCS	[M-H]-	128.7	32859911
AllCCS	[M+Na-2H]-	131.4	32859911
AllCCS	[M+HCOO]-	134.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.46 minutes	32390414
Predicted by Siyang on May 30, 2022	10.2167 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.11 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	48.6 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1410.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	341.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	114.5 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	219.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	110.1 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	357.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	404.3 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	93.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	791.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	312.8 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	999.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	230.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	303.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	472.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	236.5 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	123.5 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Oxohexanoic acid	CCCC(=O)CC(O)=O	2168.5	Standard polar	33892256
3-Oxohexanoic acid	CCCC(=O)CC(O)=O	1047.7	Standard non polar	33892256
3-Oxohexanoic acid	CCCC(=O)CC(O)=O	1129.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Oxohexanoic acid,1TMS,isomer #1	CCCC(=O)CC(=O)O[Si](C)(C)C	1179.0	Semi standard non polar	33892256
3-Oxohexanoic acid,1TMS,isomer #2	CCCC(=CC(=O)O)O[Si](C)(C)C	1330.8	Semi standard non polar	33892256
3-Oxohexanoic acid,1TMS,isomer #3	CCC=C(CC(=O)O)O[Si](C)(C)C	1300.5	Semi standard non polar	33892256
3-Oxohexanoic acid,2TMS,isomer #1	CCCC(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1366.0	Semi standard non polar	33892256
3-Oxohexanoic acid,2TMS,isomer #1	CCCC(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1340.2	Standard non polar	33892256
3-Oxohexanoic acid,2TMS,isomer #1	CCCC(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1361.0	Standard polar	33892256
3-Oxohexanoic acid,2TMS,isomer #2	CCC=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1354.6	Semi standard non polar	33892256
3-Oxohexanoic acid,2TMS,isomer #2	CCC=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1382.2	Standard non polar	33892256
3-Oxohexanoic acid,2TMS,isomer #2	CCC=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1402.8	Standard polar	33892256
3-Oxohexanoic acid,1TBDMS,isomer #1	CCCC(=O)CC(=O)O[Si](C)(C)C(C)(C)C	1400.2	Semi standard non polar	33892256
3-Oxohexanoic acid,1TBDMS,isomer #2	CCCC(=CC(=O)O)O[Si](C)(C)C(C)(C)C	1560.1	Semi standard non polar	33892256
3-Oxohexanoic acid,1TBDMS,isomer #3	CCC=C(CC(=O)O)O[Si](C)(C)C(C)(C)C	1534.7	Semi standard non polar	33892256
3-Oxohexanoic acid,2TBDMS,isomer #1	CCCC(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1791.8	Semi standard non polar	33892256
3-Oxohexanoic acid,2TBDMS,isomer #1	CCCC(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1758.4	Standard non polar	33892256
3-Oxohexanoic acid,2TBDMS,isomer #1	CCCC(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1687.6	Standard polar	33892256
3-Oxohexanoic acid,2TBDMS,isomer #2	CCC=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1786.6	Semi standard non polar	33892256
3-Oxohexanoic acid,2TBDMS,isomer #2	CCC=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1797.5	Standard non polar	33892256
3-Oxohexanoic acid,2TBDMS,isomer #2	CCC=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1715.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxohexanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000f-9000000000-f5697d85c64e8eaf34c0	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxohexanoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-0076-9600000000-ac738256ec79f62f0b76	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxohexanoic 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
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxohexanoic acid 10V, Positive-QTOF	splash10-01q9-4900000000-fcbf011b9090ad4d5985	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxohexanoic acid 20V, Positive-QTOF	splash10-00kr-9200000000-821582fe0542054a015a	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxohexanoic acid 40V, Positive-QTOF	splash10-00kf-9000000000-4b8514304d3d2971161c	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxohexanoic acid 10V, Negative-QTOF	splash10-004r-9800000000-41ec193bfcd6e2a5200f	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxohexanoic acid 20V, Negative-QTOF	splash10-052r-9100000000-7538825b0b82467b8c18	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxohexanoic acid 40V, Negative-QTOF	splash10-0a4l-9000000000-9c86489ccca13107be89	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxohexanoic acid 10V, Negative-QTOF	splash10-08i3-7900000000-ba35a052e714093bbc7f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxohexanoic acid 20V, Negative-QTOF	splash10-0a4l-9100000000-6c151f93bece48183d41	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxohexanoic acid 40V, Negative-QTOF	splash10-00kf-9000000000-66ea81befa7d2e196237	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxohexanoic acid 10V, Positive-QTOF	splash10-006x-9000000000-fabe1fc9c9dd4a561c98	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxohexanoic acid 20V, Positive-QTOF	splash10-00kf-9000000000-54990d1f19aea0f0638c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxohexanoic acid 40V, Positive-QTOF	splash10-0006-9000000000-1b199c855cf5738765a6	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	2021-09-25	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

Not Available

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Fatty Acid Biosynthesis		Not Available

Normal Concentrations

Not Available

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

FDB027867

KNApSAcK ID

Not Available

Chemspider ID

388729

KEGG Compound ID

C02122

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

439658

PDB ID

Not Available

ChEBI ID

28422

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for 3-Oxohexanoic acid (HMDB0010717)

MOL for HMDB0010717 (3-Oxohexanoic acid)

3D MOL for HMDB0010717 (3-Oxohexanoic acid)

3D SDF for HMDB0010717 (3-Oxohexanoic acid)

3D-SDF for HMDB0010717 (3-Oxohexanoic acid)

PDB for HMDB0010717 (3-Oxohexanoic acid)

3D PDB for HMDB0010717 (3-Oxohexanoic acid)

SMILES for HMDB0010717 (3-Oxohexanoic acid)

INCHI for HMDB0010717 (3-Oxohexanoic acid)

Structure for HMDB0010717 (3-Oxohexanoic acid)

3D Structure for HMDB0010717 (3-Oxohexanoic acid)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra