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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

HMDB0010721

Secondary Accession Numbers

HMDB10721

Metabolite Identification

Common Name

3-Oxooctanoic acid

Description

3-Oxooctanoic acid, also known as beta-oxocaprylic acid or 3-keto-N-caprylate, 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-Oxooctanoic acid exists in all eukaryotes, ranging from yeast to plants to humans. 3-Oxooctanoic 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-oxooctanoic acid a potential biomarker for the consumption of these foods. 3-Oxooctanoic 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-Oxooctanoic 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-Keto-N-caprylic acid	ChEBI
3-Ketooctanoic acid	ChEBI
beta-Ketocaprylic acid	ChEBI
beta-Ketooctanoic acid	ChEBI
beta-Oxocaprylic acid	ChEBI
beta-Oxooctanoic acid	ChEBI
3-Keto-N-caprylate	Generator
3-Ketooctanoate	Generator
b-Ketocaprylate	Generator
b-Ketocaprylic acid	Generator
beta-Ketocaprylate	Generator
Β-ketocaprylate	Generator
Β-ketocaprylic acid	Generator
b-Ketooctanoate	Generator
b-Ketooctanoic acid	Generator
beta-Ketooctanoate	Generator
Β-ketooctanoate	Generator
Β-ketooctanoic acid	Generator
b-Oxocaprylate	Generator
b-Oxocaprylic acid	Generator
beta-Oxocaprylate	Generator
Β-oxocaprylate	Generator
Β-oxocaprylic acid	Generator
b-Oxooctanoate	Generator
b-Oxooctanoic acid	Generator
beta-Oxooctanoate	Generator
Β-oxooctanoate	Generator
Β-oxooctanoic acid	Generator
3-Oxooctanoate	Generator
3-oxo-Octanoate	HMDB
3-oxo-Octanoic acid	HMDB

Chemical Formula

C₈H₁₄O₃

Average Molecular Weight

158.195

Monoisotopic Molecular Weight

158.094294314

IUPAC Name

3-oxooctanoic acid

Traditional Name

3-oxooctanoic acid

CAS Registry Number

Not Available

SMILES

CCCCCC(=O)CC(O)=O

InChI Identifier

InChI=1S/C8H14O3/c1-2-3-4-5-7(9)6-8(10)11/h2-6H2,1H3,(H,10,11)

InChI Key

FWNRRWJFOZIGQZ-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:44680 )
oxo fatty acid (CHEBI:44680 )
Oxo fatty acids (LMFA01060017 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0010721)
Cell membrane (HMDB: HMDB0010721)

Source

Endogenous

Endogenous (HMDB: HMDB0010721)

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

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Fatty Acid Biosynthesis (HMDB: HMDB0010721)
Fatty Acid Biosynthesis (PathBank: SMP0002360)
Fatty Acid Biosynthesis (HMDB: HMDB0010721)

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	3.56 g/L	ALOGPS
logP	1.4	ALOGPS
logP	2.03	ChemAxon
logS	-1.6	ALOGPS
pKa (Strongest Acidic)	4.58	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	6	ChemAxon
Refractivity	40.97 m³·mol⁻¹	ChemAxon
Polarizability	17.02 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]+	137.663	31661259
DarkChem	[M-H]-	135.973	31661259
DeepCCS	[M+H]+	138.063	30932474
DeepCCS	[M-H]-	134.79	30932474
DeepCCS	[M-2H]-	171.617	30932474
DeepCCS	[M+Na]+	146.87	30932474
AllCCS	[M+H]+	138.0	32859911
AllCCS	[M+H-H2O]+	134.0	32859911
AllCCS	[M+NH4]+	141.7	32859911
AllCCS	[M+Na]+	142.8	32859911
AllCCS	[M-H]-	137.0	32859911
AllCCS	[M+Na-2H]-	138.9	32859911
AllCCS	[M+HCOO]-	141.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Oxooctanoic acid	CCCCCC(=O)CC(O)=O	2375.9	Standard polar	33892256
3-Oxooctanoic acid	CCCCCC(=O)CC(O)=O	1225.1	Standard non polar	33892256
3-Oxooctanoic acid	CCCCCC(=O)CC(O)=O	1315.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Oxooctanoic acid,1TMS,isomer #1	CCCCCC(=O)CC(=O)O[Si](C)(C)C	1355.7	Semi standard non polar	33892256
3-Oxooctanoic acid,1TMS,isomer #2	CCCCCC(=CC(=O)O)O[Si](C)(C)C	1501.2	Semi standard non polar	33892256
3-Oxooctanoic acid,1TMS,isomer #3	CCCCC=C(CC(=O)O)O[Si](C)(C)C	1460.4	Semi standard non polar	33892256
3-Oxooctanoic acid,2TMS,isomer #1	CCCCCC(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1524.5	Semi standard non polar	33892256
3-Oxooctanoic acid,2TMS,isomer #1	CCCCCC(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1528.6	Standard non polar	33892256
3-Oxooctanoic acid,2TMS,isomer #1	CCCCCC(=CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1545.8	Standard polar	33892256
3-Oxooctanoic acid,2TMS,isomer #2	CCCCC=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1519.0	Semi standard non polar	33892256
3-Oxooctanoic acid,2TMS,isomer #2	CCCCC=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1537.4	Standard non polar	33892256
3-Oxooctanoic acid,2TMS,isomer #2	CCCCC=C(CC(=O)O[Si](C)(C)C)O[Si](C)(C)C	1563.6	Standard polar	33892256
3-Oxooctanoic acid,1TBDMS,isomer #1	CCCCCC(=O)CC(=O)O[Si](C)(C)C(C)(C)C	1572.9	Semi standard non polar	33892256
3-Oxooctanoic acid,1TBDMS,isomer #2	CCCCCC(=CC(=O)O)O[Si](C)(C)C(C)(C)C	1730.8	Semi standard non polar	33892256
3-Oxooctanoic acid,1TBDMS,isomer #3	CCCCC=C(CC(=O)O)O[Si](C)(C)C(C)(C)C	1696.3	Semi standard non polar	33892256
3-Oxooctanoic acid,2TBDMS,isomer #1	CCCCCC(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1968.8	Semi standard non polar	33892256
3-Oxooctanoic acid,2TBDMS,isomer #1	CCCCCC(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1934.3	Standard non polar	33892256
3-Oxooctanoic acid,2TBDMS,isomer #1	CCCCCC(=CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1853.5	Standard polar	33892256
3-Oxooctanoic acid,2TBDMS,isomer #2	CCCCC=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1964.6	Semi standard non polar	33892256
3-Oxooctanoic acid,2TBDMS,isomer #2	CCCCC=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1935.8	Standard non polar	33892256
3-Oxooctanoic acid,2TBDMS,isomer #2	CCCCC=C(CC(=O)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	1864.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxooctanoic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-9000000000-9b3ca2d13b28a5c5edc3	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxooctanoic acid GC-MS (1 TMS) - 70eV, Positive	splash10-010c-9300000000-7e5566ef916a9047e3fe	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxooctanoic 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-Oxooctanoic acid 10V, Positive-QTOF	splash10-0a4l-1900000000-cf21d374433a2daae845	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxooctanoic acid 20V, Positive-QTOF	splash10-06xw-9500000000-b82cae96c50d2357b799	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxooctanoic acid 40V, Positive-QTOF	splash10-052f-9000000000-2f425485d3253a53a6e7	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxooctanoic acid 10V, Negative-QTOF	splash10-0bt9-1900000000-8f3bd0cfff780a809513	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxooctanoic acid 20V, Negative-QTOF	splash10-08fr-7900000000-9112cbb85161de5302b1	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxooctanoic acid 40V, Negative-QTOF	splash10-0a4i-9100000000-68d647898bcdda00130e	2016-09-14	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxooctanoic acid 10V, Negative-QTOF	splash10-0a4i-2900000000-a2caa0b8429fb156ed96	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxooctanoic acid 20V, Negative-QTOF	splash10-0btc-9700000000-335d0c46b9d801f56f5a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxooctanoic acid 40V, Negative-QTOF	splash10-052f-9000000000-92713f9972c24d2ca36c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxooctanoic acid 10V, Positive-QTOF	splash10-000t-9200000000-2ec333a17165f0916338	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxooctanoic acid 20V, Positive-QTOF	splash10-00dm-9000000000-942561cb773f0f1eb232	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxooctanoic acid 40V, Positive-QTOF	splash10-00kf-9000000000-56bed0f44b01b7711e9f	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)	2021-09-25	Wishart Lab	View Spectrum
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, 1000 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 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, 900 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

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

Membrane (predicted from logP)

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

FDB027870

KNApSAcK ID

Not Available

Chemspider ID

114191

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

128859

PDB ID

OOA

ChEBI ID

44680

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-Oxooctanoic acid (HMDB0010721)

MOL for HMDB0010721 (3-Oxooctanoic acid)

3D MOL for HMDB0010721 (3-Oxooctanoic acid)

3D SDF for HMDB0010721 (3-Oxooctanoic acid)

3D-SDF for HMDB0010721 (3-Oxooctanoic acid)

PDB for HMDB0010721 (3-Oxooctanoic acid)

3D PDB for HMDB0010721 (3-Oxooctanoic acid)

SMILES for HMDB0010721 (3-Oxooctanoic acid)

INCHI for HMDB0010721 (3-Oxooctanoic acid)

Structure for HMDB0010721 (3-Oxooctanoic acid)

3D Structure for HMDB0010721 (3-Oxooctanoic acid)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra