2-Methyl-3-oxopropanoic acid

2-Methyl-3-oxopropanoic acid

IUPAC name 2-Methyl-3-oxopropanoic acid
Other names Methylmalonate semialdehyde
Identifiers
CAS number	6236-08-4
PubChem	296
ChemSpider	290^Y
KEGG	C00349 ^Y
ChEBI	CHEBI:16256 ^Y
Jmol-3D images	Image 2
SMILES CC(C=O)C(=O)O O=CC(C(=O)O)C
InChI InChI=1S/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7) ^Y Key: VOKUMXABRRXHAR-UHFFFAOYSA-N ^Y InChI=1/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7) Key: VOKUMXABRRXHAR-UHFFFAOYAB
Properties
Molecular formula	C₄H₆O₃
Molar mass	102.09 g/mol
Y (verify) (what is: Y/N?) Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

2-Methyl-3-oxopropanoic acid (or methylmalonate semialdehyde) is an intermediate in the metabolism of valine.

lysine→	Saccharopine Allysine α-Aminoadipic acid α-Aminoadipate Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA

leucine→	α-Ketoisocaproic acid Isovaleryl-CoA 3-Methylcrotonyl-CoA 3-Methylglutaconyl-CoA HMG-CoA

tryptophan→alanine→	N'-Formylkynurenine Kynurenine Anthranilic acid 3-Hydroxykynurenine 3-Hydroxyanthranilic acid 2-Amino-3-carboxymuconic semialdehyde 2-Aminomuconic semialdehyde 2-Aminomuconic acid Glutaryl-CoA

G→pyruvate→citrate

glycine→serine→	3-Phosphoglyceric acid glycine→creatine: Glycocyamine Phosphocreatine Creatinine

G→glutamate→
α-ketoglutarate

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde

proline→	1-Pyrroline-5-carboxylic acid

arginine→	Ornithine Putrescine Agmatine

other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

G→propionyl-CoA→
succinyl-CoA

valine→	α-Ketoisovaleric acid Isobutyryl-CoA Methacrylyl-CoA 3-Hydroxyisobutyryl-CoA 3-Hydroxyisobutyric acid 2-Methyl-3-oxopropanoic acid

isoleucine→	2,3-Dihydroxy-3-methylpentanoic acid 2-Methylbutyryl-CoA Tiglyl-CoA 2-Methylacetoacetyl-CoA

methionine→	generation of homocysteine: S-Adenosyl methionine S-Adenosyl-L-homocysteine Homocysteine conversion to cysteine: Cystathionine alpha-Ketobutyric acid+Cysteine

threonine→	α-Ketobutyric acid

propionyl-CoA→	Methylmalonyl-CoA

G→fumarate

phenylalanine→tyrosine→	4-Hydroxyphenylpyruvic acid Homogentisic acid 4-Maleylacetoacetate

G→oxaloacetate

see urea cycle

Other

Cysteine metabolism	Cysteine sulfinic acid

M: MET

mt, k, c/g/r/p/y/i, f/h/s/l/o/e, a/u, n, m

k, cgrp/y/i, f/h/s/l/o/e, au, n, m, epon

m (A16/C10), i (k, c/g/r/p/y/i, f/h/s/o/e, a/u, n, m)

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2-Methyl-3-oxopropanoic acid

2-Methyl-3-oxopropanoic acid

See also