4-methyl-2-oxopentanoic acid (CHEBI:48430)

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CHEBI:48430 - 4-methyl-2-oxopentanoic acid

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ChEBI Name	4-methyl-2-oxopentanoic acid

ChEBI ID	CHEBI:48430

Definition	A 2-oxo monocarboxylic acid that is pentanoic acid (valeric acid) substituted with a keto group at C-2 and a methyl group at C-4. A metabolite that has been found to accumulate in maple syrup urine disease.

Stars	This entity has been manually annotated by the ChEBI Team.

Secondary ChEBI IDs	CHEBI:41619, CHEBI:1891

Supplier Information	ChemicalBook:CB5157543, eMolecules:529078, ZINC000001532578

Download	Molfile XML SDF

more structures >>

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19 18 0 0 0 0 999 V2000

1.2541 2.2114 0.0940 C 0 0 0 0 0 0 0 0 0 0 0 0

0.4249 2.8098 -0.5574 O 0 0 0 0 0 0 0 0 0 0 0 0

2.5140 2.6757 0.1677 O 0 0 0 0 0 0 0 0 0 0 0 0

0.8763 0.9600 0.8096 C 0 0 0 0 0 0 0 0 0 0 0 0

1.7023 0.3629 1.4588 O 0 0 0 0 0 0 0 0 0 0 0 0

-0.5341 0.4398 0.7255 C 0 0 0 0 0 0 0 0 0 0 0 0

-0.6546 -0.8468 1.5446 C 0 0 1 0 0 0 0 0 0 0 0 0

-2.0862 -1.3753 1.4600 C 0 0 0 0 0 0 0 0 0 0 0 0

0.3102 -1.8958 0.9899 C 0 0 0 0 0 0 0 0 0 0 0 0

2.7588 3.4877 -0.2967 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.7835 0.2326 -0.3138 H 0 0 0 0 0 0 0 0 0 0 0 0

-1.2214 1.1869 1.1215 H 0 0 0 0 0 0 0 0 0 0 0 0

-0.4046 -0.6392 2.5861 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.1707 -2.2921 2.0433 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.7735 -0.6282 1.8561 H 0 0 0 0 0 0 0 0 0 0 0 0

-2.3355 -1.5830 0.4198 H 0 0 0 0 0 0 0 0 0 0 0 0

0.0609 -2.1035 -0.0503 H 0 0 0 0 0 0 0 0 0 0 0 0

1.3320 -1.5189 1.0512 H 0 0 0 0 0 0 0 0 0 0 0 0

0.2256 -2.8122 1.5741 H 0 0 0 0 0 0 0 0 0 0 0 0

1 2 2 0 0 0 0

1 3 1 0 0 0 0

1 4 1 0 0 0 0

3 10 1 0 0 0 0

4 5 2 0 0 0 0

4 6 1 0 0 0 0

6 7 1 0 0 0 0

6 11 1 0 0 0 0

6 12 1 0 0 0 0

7 8 1 0 0 0 0

7 9 1 0 0 0 0

7 13 1 0 0 0 0

8 14 1 0 0 0 0

8 15 1 0 0 0 0

8 16 1 0 0 0 0

9 17 1 0 0 0 0

9 18 1 0 0 0 0

9 19 1 0 0 0 0

M END): 18 ms

reading 19 atoms

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Formula

C6H10O3

Net Charge

Average Mass

130.14180

Monoisotopic Mass

130.06299

InChI

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

InChIKey

BKAJNAXTPSGJCU-UHFFFAOYSA-N

SMILES

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

Metabolite of Species	Details
Chlamydomonas reinhardtii (NCBI:txid3055)	See: PubMed
Homo sapiens (NCBI:txid9606)	See: PubMed

Roles Classification
Chemical Role(s):	Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	algal metabolite Any eukaryotic metabolite produced during a metabolic reaction in algae including unicellular organisms like chlorella and diatoms to multicellular organisms like giant kelps and brown algae. human metabolite Any mammalian metabolite produced during a metabolic reaction in humans (Homo sapiens).

View more via ChEBI Ontology

ChEBI Ontology
Outgoing	4-methyl-2-oxopentanoic acid (CHEBI:48430) has functional parent valeric acid (CHEBI:17418) 4-methyl-2-oxopentanoic acid (CHEBI:48430) has role algal metabolite (CHEBI:84735) 4-methyl-2-oxopentanoic acid (CHEBI:48430) has role human metabolite (CHEBI:77746) 4-methyl-2-oxopentanoic acid (CHEBI:48430) is a 2-oxo monocarboxylic acid (CHEBI:35910) 4-methyl-2-oxopentanoic acid (CHEBI:48430) is a branched-chain keto acid (CHEBI:191197) 4-methyl-2-oxopentanoic acid (CHEBI:48430) is conjugate acid of 4-methyl-2-oxopentanoate (CHEBI:17865)

Incoming	4-methyl-2-oxopentanoate (CHEBI:17865) is conjugate base of 4-methyl-2-oxopentanoic acid (CHEBI:48430)

IUPAC Name

4-methyl-2-oxopentanoic acid

Synonyms	Sources
2-OXO-4-METHYLPENTANOIC ACID	PDBeChem
2-Oxoisocaproate	KEGG COMPOUND
4-Methyl-2-oxopentanoate	KEGG COMPOUND
4-methyl-2-oxovaleric acid	ChemIDplus
α-ketoisocaproic acid	ChemIDplus
Ketoleucine	HMDB

Manual Xrefs	Databases
2K-4CH3-PENTANOATE	MetaCyc
C00019677	KNApSAcK
C00233	KEGG COMPOUND
COI	PDBeChem
DB03229	DrugBank
HMDB0000695	HMDB
View more database links

Registry Numbers	Types	Sources
1701823	Reaxys Registry Number	Reaxys
816-66-0	CAS Registry Number	KEGG COMPOUND
816-66-0	CAS Registry Number	ChemIDplus

Citations

Roux A, Xu Y, Heilier JF, Olivier MF, Ezan E, Tabet JC, Junot C (2012)
Annotation of the human adult urinary metabolome and metabolite identification using ultra high performance liquid chromatography coupled to a linear quadrupole ion trap-Orbitrap mass spectrometer.
Analytical chemistry 84, 6429-6437 [PubMed:22770225]
[show Abstract]

Sgaravatti AM, Rosa RB, Schuck PF, Ribeiro CA, Wannmacher CM, Wyse AT, Dutra-Filho CS, Wajner M (2003)
Inhibition of brain energy metabolism by the alpha-keto acids accumulating in maple syrup urine disease.
Biochimica et biophysica acta 1639, 232-238 [PubMed:14636955]
[show Abstract]

Last Modified

21 April 2022

CHEBI:48430 - 4-methyl-2-oxopentanoic acid

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