Livestock Metabolome Database: Showing metabocard for Alpha-ketoisovaleric acid (LMDB00006)

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

Record Information

Version

1.0

Creation Date

2016-07-13 19:22:12 UTC

Update Date

2016-08-02 20:40:49 UTC

Lmdb

LMDB00006

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Alpha-ketoisovaleric acid

Description

alpha-Ketoisovaleric acid, also known as a-keto-isovalerate or 3-methyl-2-oxobutanoate, 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. alpha-Ketoisovaleric acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. alpha-Ketoisovaleric acid exists in all living species, ranging from bacteria to humans. alpha-Ketoisovaleric acid is a fruity tasting compound. Outside of the human body, alpha-Ketoisovaleric acid has been detected, but not quantified in, several different foods, such as root vegetables, jerusalem artichokes, rapinis, chia, and cowpea. This could make alpha-ketoisovaleric acid a potential biomarker for the consumption of these foods. alpha-Ketoisovaleric acid is a potentially toxic compound. alpha-Ketoisovaleric acid, with regard to humans, has been found to be associated with the diseases such as colorectal cancer; alpha-ketoisovaleric acid has also been linked to the inborn metabolic disorder maple syrup urine disease. A 2-oxo monocarboxylic acid that is the 2-oxo derivative of isovaleric acid.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-Keto-3-methylbutyric acid	ChEBI
2-Ketoisovaleric acid	ChEBI
2-Ketovaline	ChEBI
2-oxo-3-Methylbutanoic acid	ChEBI
2-oxo-3-Methylbutyric acid	ChEBI
2-Oxoisovaleric acid	ChEBI
3-Methyl-2-oxobutanoate	ChEBI
3-Methyl-2-oxobutyric acid	ChEBI
alpha-Keto-isovaleric acid	ChEBI
alpha-Ketovaline	ChEBI
alpha-oxo-beta-Methylbutyricacid	ChEBI
alpha-Oxoisovaleric acid	ChEBI
Dimethylpyruvic acid	ChEBI
Isopropylglyoxylic acid	ChEBI
2-oxo-3-Methylbutanoate	Kegg
2-Oxoisovalerate	Kegg
2-Oxoisopentanoate	Kegg
2-Keto-3-methylbutyrate	Generator
2-Ketoisovalerate	Generator
2-oxo-3-Methylbutyrate	Generator
3-Methyl-2-oxobutanoic acid	Generator
3-Methyl-2-oxobutyrate	Generator
a-Keto-isovalerate	Generator
a-Keto-isovaleric acid	Generator
alpha-Keto-isovalerate	Generator
Α-keto-isovalerate	Generator
Α-keto-isovaleric acid	Generator
a-Ketovaline	Generator
Α-ketovaline	Generator
a-oxo-b-Methylbutyricacid	Generator
Α-oxo-β-methylbutyricacid	Generator
a-Oxoisovalerate	Generator
a-Oxoisovaleric acid	Generator
alpha-Oxoisovalerate	Generator
Α-oxoisovalerate	Generator
Α-oxoisovaleric acid	Generator
Dimethylpyruvate	Generator
Isopropylglyoxylate	Generator
2-Oxoisopentanoic acid	Generator
a-Ketoisovalerate	Generator
a-Ketoisovaleric acid	Generator
alpha-Ketoisovalerate	Generator
Α-ketoisovalerate	Generator
Α-ketoisovaleric acid	Generator
2-Ketoisvaleric acid	HMDB
2-oxo-3-Methyl-butyrate	HMDB
3-Methyl-2-oxo-butanoate	HMDB
3-Methyl-2-oxo-butanoic acid	HMDB
3-Methyl-2-oxo-butyrate	HMDB
3-Methyl-2-oxo-butyric acid	HMDB
3-Methyl-2-oxobutinoate	HMDB
3-Methyl-2-oxobutinoic acid	HMDB
a-Keto-b-methylbutyrate	HMDB
a-Keto-b-methylbutyric acid	HMDB
a-oxo-b-Methylbutyrate	HMDB
a-oxo-b-Methylbutyric acid	HMDB
alpha-Keto-beta-methylbutyrate	HMDB
alpha-Keto-beta-methylbutyric acid	HMDB
alpha-oxo-beta-Methylbutyrate	HMDB
alpha-oxo-beta-Methylbutyric acid	HMDB
Ketovaline	HMDB
alpha-Ketoisopentanoic acid	HMDB
alpha-Ketoisovaleric acid	Generator, MeSH

Chemical Formula

C₅H₈O₃

Average Molecular Weight

116.1152

Monoisotopic Molecular Weight

116.047344122

IUPAC Name

3-methyl-2-oxobutanoic acid

Traditional Name

α-ketoisovalerate

CAS Registry Number

759-05-7

SMILES

CC(C)C(=O)C(O)=O

InChI Identifier

InChI=1S/C5H8O3/c1-3(2)4(6)5(7)8/h3H,1-2H3,(H,7,8)

InChI Key

QHKABHOOEWYVLI-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:16530 )
Branched fatty acids (C00141 )
Branched fatty acids (LMFA01020274 )

Ontology

Status

Detected and Quantified

Origin

Not Available

Biofunction

Not Available

Application

Not Available

Cellular locations

Not Available

Physical Properties

State

Not Available

Experimental 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

Predicted Properties

Property	Value	Source
logP	0.49	ALOGPS
logP	1.31	ChemAxon
logS	-0.59	ALOGPS
pKa (Strongest Acidic)	3.37	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	2	ChemAxon
Refractivity	27.19 m³·mol⁻¹	ChemAxon
Polarizability	11.04 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	Yes	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000i-9500000000-ff936b879a69b5d118f8	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000i-8920000000-e37b37d64d43dcf763f0	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-000i-9400000000-e3995acc4818a98d0f48	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (1 MEOX; 1 TMS)	splash10-0f79-9720000000-5d89487273e44ea61a68	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-9700000000-209c737dcac7df2b198c	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0f79-5920000000-759a2f01b4f52767ade2	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9500000000-ff936b879a69b5d118f8	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-8920000000-e37b37d64d43dcf763f0	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-000i-9400000000-e3995acc4818a98d0f48	Spectrum
GC-MS	GC-MS Spectrum - GC-MS (Non-derivatized)	splash10-0f79-9720000000-5d89487273e44ea61a68	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-7900000000-7e325567183fb56996d5	Spectrum
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-0ufr-0930000000-be90b06add7135b4a539	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-00dl-9000000000-52f9d8fc8386e4c512fe	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-006x-9600000000-52aefdc997dac92c8459	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, Positive	Not Available	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000i-9000000000-10ab58a33e9ca7dbace0	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-000i-9000000000-ad51ff01c94b6046ad64	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Negative	splash10-014i-0900000000-9993174a7b1801b90ddb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Negative	splash10-00xr-9500000000-293818b81e0879b6feb2	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Negative	splash10-00di-9000000000-75058f27a2178b9cf121	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Negative	splash10-0006-9000000000-4c20af39e8ee009d5278	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-014i-0900000000-9993174a7b1801b90ddb	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00xr-9500000000-1a58c6a6b4f5477dabdd	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-00di-9000000000-75058f27a2178b9cf121	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ , negative	splash10-0006-9000000000-cc4465a47e663be66df5	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-00di-9100000000-19511890852fce513a02	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 20V, Positive	splash10-00kf-9300000000-30d3bdfb6d38dbb8e101	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 40V, Positive	splash10-000l-9000000000-879b6502ff380673b776	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 10V, Positive	splash10-0159-9800000000-0cf4d3a0e7b3356995c6	Spectrum
LC-MS/MS	LC-MS/MS Spectrum - 35V, Positive	splash10-014o-9900000000-f35430a2eaea0d81df32	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00r2-9400000000-21f8c3fae79161c82099	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00dl-9000000000-5f25e41413738bb6b5d7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0006-9000000000-801af00dea93fcfd637d	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-8900000000-5185c7dfc72c25069904	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00xs-9200000000-7e2a275a65197f96f5d7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0600-9000000000-0013e0ff06f9896a1337	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-01b9-6900000000-7f00871b074cbd9a42e6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-06di-9400000000-6d56778068e11e4f8e85	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-b445e7fc67a8ff2bd3ba	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-006x-9000000000-733fb7227d2d053b112f	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
1D NMR	13C NMR Spectrum	Not Available	Spectrum
1D NMR	1H NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,13C] 2D NMR Spectrum	Not Available	Spectrum
2D NMR	[1H,1H] 2D NMR Spectrum	Not Available	Spectrum

Biological Properties

Cellular Locations

Not Available

Biofluid Locations and Tissue Locations

Meat
Serum

Concentrations

Biofluid	Status	Value	Condition	Species	Reference	Details
Meat	Detected and Quantified	0.26 +/- 0.10 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	0.29 +/- 0.10 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	0.38 +/- 0.09 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Meat	Detected and Quantified	0.45 +/- 0.09 umol/g	Not Available	Bovine	S. F. Graham, T. ...	details
Serum	Detected but not Quantified	Not Applicable	Not Available	Bovine	25599412	details