Methylmalonic acid semialdehyde

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Methylmalonic acid semialdehyde
Names

Preferred IUPAC name 2-Methyl-3-oxopropanoic acid
Other names Methylmalonate semialdehyde
Identifiers
CAS Number	6236-08-4
3D model (JSmol)	Interactive image Interactive image
ChEBI	CHEBI:16256
ChemSpider	290
KEGG	C00349
PubChem CID	296
UNII	036CTC7X1V
CompTox Dashboard (EPA)	DTXSID60274265
InChI InChI=1S/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7)Key: VOKUMXABRRXHAR-UHFFFAOYSA-N InChI=1/C4H6O3/c1-3(2-5)4(6)7/h2-3H,1H3,(H,6,7)Key: VOKUMXABRRXHAR-UHFFFAOYAB
SMILES CC(C=O)C(=O)O O=CC(C(=O)O)C
Properties
Chemical formula	C₄H₆O₃
Molar mass	102.09 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). N verify (what is ?) Infobox references

Chemical compound

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

References

Voet, Donald (2011). Biochemistry. Judith G. Voet (4th ed.). Hoboken, NJ: John Wiley & Sons. ISBN 978-0-470-57095-1. OCLC 690489261.

lysine→	Saccharopine Allysine α-Aminoadipic acid 2-Oxoadipic acid Glutaryl-CoA Glutaconyl-CoA Crotonyl-CoA β-Hydroxybutyryl-CoA
leucine→	β-Hydroxy β-methylbutyric acid β-Hydroxy β-methylbutyryl-CoA Isovaleryl-CoA α-Ketoisocaproic acid β-Ketoisocaproic acid β-Ketoisocaproyl-CoA β-Leucine β-Methylcrotonyl-CoA β-Methylglutaconyl-CoA β-Hydroxy β-methylglutaryl-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

histidine→	Urocanic acid Imidazol-4-one-5-propionic acid Formiminoglutamic acid Glutamate-1-semialdehyde
proline→	1-Pyrroline-5-carboxylic acid
arginine→	Agmatine Ornithine Citrulline Cadaverine Putrescine
other	cysteine+glutamate→glutathione: γ-Glutamylcysteine

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 α-Ketobutyric acid + Cysteine
threonine→	α-Ketobutyric acid
propionyl-CoA→	Methylmalonyl-CoA

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

Other

Cysteine metabolism	Cysteine sulfinic acid

anabolism

R5P→IMP:	Ribose 5-phosphate (R5P) Phosphoribosyl pyrophosphate (PRPP) Phosphoribosylamine (PRA) Glycineamide ribonucleotide (GAR) Phosphoribosyl-N-formylglycineamide (FGAR) 5′-Phosphoribosylformylglycinamidine (FGAM) 5-Aminoimidazole ribotide (AIR) 5′-Phosphoribosyl-4-carboxy-5-aminoimidazole (CAIR) Phosphoribosylaminoimidazolesuccinocarboxamide (SAICAR) AICA ribonucleotide (AICAR) 5-Formamidoimidazole-4-carboxamide ribotide (FAICAR)
IMP→AMP:	Adenylosuccinate
IMP→GMP:	Xanthosine monophosphate

catabolism

anabolism

catabolism

uracil:	β-Alanine Dihydrouracil 3-Ureidopropionic acid
thymine:	3-Aminoisobutyric acid Dihydrothymine β-Ureidoisobutyric acid

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