Bovine Metabolome Database: Showing metabocard for 3-Methyl-2-oxovaleric acid (BMDB0000491)

Identification Taxonomy Physical properties Pathways Spectra Concentrations Links References enzymes (3) Show 3 proteins XML

Record Information

Version

1.0

Creation Date

2016-09-30 22:31:31 UTC

Update Date

2020-05-21 16:28:45 UTC

BMDB ID

BMDB0000491

Secondary Accession Numbers

BMDB00491

Metabolite Identification

Common Name

3-Methyl-2-oxovaleric acid

Description

3-Methyl-2-oxovaleric acid, also known as 3-methyl-2-oxopentanoate or α-keto-β-methyl-N-valeric acid, 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. 3-Methyl-2-oxovaleric acid is an extremely weak basic (essentially neutral) compound (based on its pKa). 3-Methyl-2-oxovaleric acid exists in all living organisms, ranging from bacteria to humans. 3-Methyl-2-oxovaleric acid is a potentially toxic compound.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
2-oxo-3-Methyl-N-valeric acid	ChEBI
2-oxo-3-Methylpentanoic acid	ChEBI
2-oxo-3-Methylvalerate	ChEBI
2-oxo-3-Methylvaleric acid	ChEBI
2-Oxoisoleucine	ChEBI
2-Oxokolavenic acid	ChEBI
3-Ethyl-3-methylpyruvic acid	ChEBI
3-Methyl-2-oxopentanoic acid	ChEBI
alpha-Keto-beta-methyl-N-valeric acid	ChEBI
alpha-Keto-beta-methylvaleric acid	ChEBI
alpha-oxo-beta-Methyl-N-valeric acid	ChEBI
alpha-oxo-beta-Methylvaleric acid	ChEBI
Ketoisoleucine	ChEBI
2-oxo-3-Methyl-N-valerate	Generator
2-oxo-3-Methylpentanoate	Generator
2-Oxokolavenate	Generator
3-Ethyl-3-methylpyruvate	Generator
3-Methyl-2-oxopentanoate	Generator
a-Keto-b-methyl-N-valerate	Generator
a-Keto-b-methyl-N-valeric acid	Generator
alpha-Keto-beta-methyl-N-valerate	Generator
Α-keto-β-methyl-N-valerate	Generator
Α-keto-β-methyl-N-valeric acid	Generator
a-Keto-b-methylvalerate	Generator
a-Keto-b-methylvaleric acid	Generator
alpha-Keto-beta-methylvalerate	Generator
Α-keto-β-methylvalerate	Generator
Α-keto-β-methylvaleric acid	Generator
a-oxo-b-Methyl-N-valerate	Generator
a-oxo-b-Methyl-N-valeric acid	Generator
alpha-oxo-beta-Methyl-N-valerate	Generator
Α-oxo-β-methyl-N-valerate	Generator
Α-oxo-β-methyl-N-valeric acid	Generator
a-oxo-b-Methylvalerate	Generator
a-oxo-b-Methylvaleric acid	Generator
alpha-oxo-beta-Methylvalerate	Generator
Α-oxo-β-methylvalerate	Generator
Α-oxo-β-methylvaleric acid	Generator
3-Methyl-2-oxovalerate	Generator
(3R)-3-Methyl-2-oxopentanoate	HMDB
(3R)-3-Methyl-2-oxopentanoic acid	HMDB
(R)-3-Methyl-2-oxopentanoate	HMDB
(R)-3-Methyl-2-oxopentanoic acid	HMDB
(S)-3-Methyl-2-oxopentanoate	HMDB
(S)-3-Methyl-2-oxopentanoic acid	HMDB
2-Keto-3-methylvalerate	HMDB
2-Keto-3-methylvaleric acid	HMDB
3-Methyl-2-oxo-pentanoate	HMDB
3-Methyl-2-oxo-pentanoic acid	HMDB
3-Methyl-2-oxo-valerate	HMDB
3-Methyl-2-oxo-valeric acid	HMDB
3-Methyl-2-oxovaleric	HMDB
2-Keto methylvalerate	HMDB
KMVA	HMDB
alpha-Keto-beta-methylvaleric acid, calcium salt, (S)-isomer	HMDB
alpha-Keto-beta-methylvaleric acid, monosodium salt, (S)-isomer	HMDB
alpha-Keto-beta-methylvaleric acid, (S)-isomer	HMDB
alpha-Keto-beta-methylvaleric acid, calcium salt	HMDB
alpha-Keto-beta-methylvaleric acid, sodium salt, (+-)-isomer	HMDB
alpha-Keto-beta-methylvaleric acid, (+-)-isomer	HMDB
alpha-Keto-beta-methylvaleric acid, sodium salt	HMDB

Chemical Formula

C₆H₁₀O₃

Average Molecular Weight

130.1418

Monoisotopic Molecular Weight

130.062994186

IUPAC Name

3-methyl-2-oxopentanoic acid

Traditional Name

3-methyl-2-oxopentanoic acid

CAS Registry Number

1460-34-0

SMILES

CCC(C)C(=O)C(O)=O

InChI Identifier

InChI=1S/C6H10O3/c1-3-4(2)5(7)6(8)9/h4H,3H2,1-2H3,(H,8,9)

InChI Key

JVQYSWDUAOAHFM-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:35932 )

Ontology

Status

Expected but not Quantified

Origin

Endogenous

Exogenous

Biofunction

Not Available

Application

Not Available

Cellular locations

Cell membrane
Cytoplasm
Membrane

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	915.5 mg/mL	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1	ALOGPS
logP	1.75	ChemAxon
logS	-1.1	ALOGPS
pKa (Strongest Acidic)	3.52	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	31.79 m³·mol⁻¹	ChemAxon
Polarizability	13.09 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
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-000i-9610000000-d2ffd4c2796688c555ee	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (3 TMS)	splash10-000i-9720000000-9cbc934e100bedd87f17	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000i-9720000000-5acbdc73aee24c023763	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)	splash10-000i-6930000000-8c2cf1d8df538010611b	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-000i-6930000000-7bef6751c4c607393e5e	View in MoNA
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0hg9-4950000000-3e1c700a6f553bf63afb	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9610000000-d2ffd4c2796688c555ee	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9720000000-9cbc934e100bedd87f17	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-9720000000-5acbdc73aee24c023763	View in MoNA
GC-MS	GC-MS Spectrum - GC-EI-TOF (Non-derivatized)	splash10-000i-6930000000-8c2cf1d8df538010611b	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-056r-9000000000-d08073312b337cdae9e6	View in MoNA
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-05bo-9400000000-9937bff65302162dc3b9	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-000w-9300000000-0a6ff60455403c38be39	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-0002-9000000000-7ee6d2fb63c6ea4cccfa	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-002b-9000000000-47d18dff23b741029581	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , negative	splash10-004i-0900000000-ae9da2a9acfa56fc6091	View in MoNA
LC-MS/MS	LC-MS/MS Spectrum - LC-ESI-IT , negative	splash10-004r-5900000000-a3f740a5c859439255be	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06sr-7900000000-4920c1aefcca814ec1f6	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4r-9100000000-16995fa8eb603d828a2f	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4i-9000000000-a6ccc899039a438533ae	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-004r-5900000000-50107933abbe9c175553	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-01ri-9700000000-23998218af9ee2898594	View in MoNA
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9000000000-a30461e2df45eeb8f795	View in MoNA
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	Not Available	View in JSpectraViewer
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Not Available	View in JSpectraViewer

Biological Properties

Cellular Locations

Cell membrane
Cytoplasm
Membrane

Biospecimen Locations

Placenta
Prostate Tissue

Pathways

Name	SMPDB/Pathwhiz	KEGG
Valine, Leucine, and Isoleucine Degradation		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Placenta	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details
Prostate Tissue	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Normal	Not Applicable	details

Abnormal Concentrations

Not Available

External Links

HMDB ID

HMDB0000491

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021447

KNApSAcK ID

Not Available

Chemspider ID

KEGG Compound ID

C03465

BioCyc ID

Not Available

BiGG ID

35662

Wikipedia Link

Not Available

METLIN ID

5478

PubChem Compound

PDB ID

Not Available

ChEBI ID

35932

References

Synthesis Reference

Kondo, Shigeo; Sudo, Tetsuji; Ogiwara, Mitsuo; Takeuchi, Hiroshi. a-Oxo-b-methyl-n-valeric acid and its salts. Jpn. Kokai Tokkyo Koho (1979), 3 pp.

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Enzymes

Enzyme Details

1. Branched-chain-amino-acid aminotransferase, mitochondrial

General function:: Amino acid transport and metabolism
Specific function:: Catalyzes the first reaction in the catabolism of the essential branched chain amino acids leucine, isoleucine, and valine. May also function as a transporter of branched chain alpha-keto acids (By similarity).
Gene Name:: BCAT2
Uniprot ID:: Q5EA40
Molecular weight:: 44648.0

Reactions

L-Isoleucine + Oxoglutaric acid → 3-Methyl-2-oxovaleric acid + L-Glutamic acid	details

Enzyme Details

2. 2-oxoisovalerate dehydrogenase subunit alpha, mitochondrial

General function:: Energy production and conversion
Specific function:: The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:: BCKDHA
Uniprot ID:: P11178
Molecular weight:: 51678.0

Reactions

3-Methyl-2-oxovaleric acid + Thiamine pyrophosphate → 2-Methyl-1-hydroxypropyl-ThPP + Carbon dioxide	details

Enzyme Details

3. 2-oxoisovalerate dehydrogenase subunit beta, mitochondrial

General function:: Energy production and conversion
Specific function:: The branched-chain alpha-keto dehydrogenase complex catalyzes the overall conversion of alpha-keto acids to acyl-CoA and CO(2). It contains multiple copies of three enzymatic components: branched-chain alpha-keto acid decarboxylase (E1), lipoamide acyltransferase (E2) and lipoamide dehydrogenase (E3).
Gene Name:: BCKDHB
Uniprot ID:: P21839
Molecular weight:: 42935.0

Reactions

3-Methyl-2-oxovaleric acid + Thiamine pyrophosphate → 2-Methyl-1-hydroxypropyl-ThPP + Carbon dioxide	details

Showing metabocard for 3-Methyl-2-oxovaleric acid (BMDB0000491)

Structure for BMDB0000491 (3-Methyl-2-oxovaleric acid)

Enzymes

Reactions

Reactions

Reactions