Compound

(S)-3-methyl-2-oxopentanoate

The conjugate base of (S)-3-methyl-2-oxopentanoic acid.

Definition from ChEBI (CHEBI:35146), read 2026-09-23. CC BY 4.0.

CHEBI:35146ChEBI

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Structure

2D depiction · 3D model shown

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A generated conformer of (S)-3-methyl-2-oxopentanoate — one low-energy arrangement PubChem computed, not a measured structure. Hydrogens are not drawn; the formula counts them.

Class: Organic compound, anion
Formula: C6H9O3
Mass: 129.135 g/mol
Charge: -1
InChIKey: JVQYSWDUAOAHFM-BYPYZUCNSA-M
SMILES: CC[C@H](C)C(=O)C(=O)[O-]
Look it up: ChEBI PubChem By InChIKey

Identity from ChEBI, geometry from PubChem. Not evidence.

What it touches on the way

Mechanistic reach

3 entities

3 entities reached.

0 reported hops3 assembled from the scaffold

BCKDHAProteinUNIPROT:P12694substrate ofInferred only19 paths19 endpoints
BCKDHBProteinUNIPROT:P21953substrate ofInferred only16 paths16 endpoints
L-isoleucineCompoundCHEBI:17191converted toInferred only10 paths5 endpoints

What the reference databases state

Chemical structure

(S)-3-methyl-2-oxopentanoate has the functional parent pentanoateCompoundChEBI CHEBI:35146Inferred only

Statements

7 statements

7 statements · 1 reference database · Subject: (S)-3-methyl-2-oxopentanoate · Sources: Rhea

Order

(S)-3-methyl-2-oxopentanoate is converted to L-isoleucineCompoundRhea RHEA:61232Inferred only
L-isoleucine is converted to (S)-3-methyl-2-oxopentanoateCompoundRhea RHEA:24801Inferred only
L-isoleucine is converted to (S)-3-methyl-2-oxopentanoateCompoundRhea RHEA:32959Inferred only
L-isoleucine is converted to (S)-3-methyl-2-oxopentanoateCompoundRhea RHEA:61232Inferred only
(S)-3-methyl-2-oxopentanoate is converted to L-isoleucineCompoundRhea RHEA:32959Inferred only
(S)-3-methyl-2-oxopentanoate is a substrate of BCKDHAProteinRhea RHEA:84643Inferred only
(S)-3-methyl-2-oxopentanoate is a substrate of BCKDHBProteinRhea RHEA:84643Inferred only

Reactions

10 reactions

(S)-3-methyl-2-oxopentanoate+L-valine3-methyl-2-oxobutanoate+L-isoleucine
Reaction pageDirection not assertedBalanced
Rhea RHEA:11468CC BY 4.0Reference data
(S)-3-methyl-2-oxopentanoate+hydronCHEBI:16182+carbon dioxide
Reaction pageDirection not assertedBalanced
Rhea RHEA:21108CC BY 4.0Reference data
L-isoleucine+2-oxoglutarate(2-)(S)-3-methyl-2-oxopentanoate+L-glutamate(1-)
Catalysed by BCAT2 or BCAT1
Reaction pageLeft to rightBalanced
Rhea RHEA:24801CC BY 4.0Reference data
CHEBI:49258(S)-3-methyl-2-oxopentanoate+water
Reaction pageDirection not assertedBalanced
Rhea RHEA:27694CC BY 4.0Reference data
(S)-3-methyl-2-oxopentanoate+NAD(1-)+coenzyme A(4-)CHEBI:88166+carbon dioxide+NADH(2-)
Reaction pageDirection not assertedBalanced
Rhea RHEA:30907CC BY 4.0Reference data
L-isoleucine+NAD(1-)+water(S)-3-methyl-2-oxopentanoate+ammonium+NADH(2-)+hydron
Reaction pageDirection not assertedBalanced
Rhea RHEA:32959CC BY 4.0Reference data
L-isoleucine+dioxygen+water(S)-3-methyl-2-oxopentanoate+hydrogen peroxide+ammonium
Reaction pageDirection not assertedBalanced
Rhea RHEA:61232CC BY 4.0Reference data
CHEBI:85306+dioxygen+water(S)-3-methyl-2-oxopentanoate+hydrogen peroxide+ammonium
Reaction pageDirection not assertedBalanced
Rhea RHEA:78223CC BY 4.0Reference data
L-isoleucine+glyoxylate(S)-3-methyl-2-oxopentanoate+glycine
Reaction pageDirection not assertedBalanced
Rhea RHEA:81615CC BY 4.0Reference data
N(6)-[(R)-lipoyl]-L-lysyl-[protein]+(S)-3-methyl-2-oxopentanoate+hydronN(6)-{(R)-S(8)-[(2S)-2-methylbutanoyl]dihydrolipoyl}-L-lysyl-[protein]+carbon dioxide
Catalysed by BCKDHA or BCKDHB
Reaction pageLeft to rightBalance undeterminable
Rhea RHEA:84643CC BY 4.0Reference data

Other names

2 names

Resolves to: (S)-3-methyl-2-oxopentanoate

Also called: (S)-3-methyl-2-oxovalerate
Systematic name: (3S)-3-methyl-2-oxopentanoate