4-Maleylacetoacetic acid

4-Maleylacetoacetic acid
Names

IUPAC name (Z)-4,6-Dioxooct-2-enedioic acid
Other names 4-Maleylacetoacetate
Identifiers
CAS Registry Number	5698-52-2^N
ChEBI	CHEBI:47904^Y
ChEMBL	ChEMBL1743220^N
ChemSpider	4444078^Y
InChI InChI=1S/C8H8O6/c9-5(1-2-7(11)12)3-6(10)4-8(13)14/h1-2H,3-4H2,(H,11,12)(H,13,14)/b2-1-^Y Key: GACSIVHAIFQKTC-UPHRSURJSA-N^Y InChI=1/C8H8O6/c9-5(1-2-7(11)12)3-6(10)4-8(13)14/h1-2H,3-4H2,(H,11,12)(H,13,14)/b2-1- Key: GACSIVHAIFQKTC-UPHRSURJBV
Jmol-3D images	Image
KEGG	C01036^Y
PubChem	5280393
SMILES O=C(/C=C\C(=O)O)CC(=O)CC(=O)O
Properties
Molecular formula	C₈H₈O₆
Molar mass	200.15 g·mol⁻¹
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
Infobox references

4-Maleylacetoacetate (4-maleylacetoacetate) is an intermediate in the metabolism of tyrosine.

lysine→	Saccharopine Allysine α-Aminoadipic acid α-Ketoadipate 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→	Agmatine Ornithine 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 alpha-Ketobutyric acid+Cysteine

threonine→	α-Ketobutyric acid

propionyl-CoA→	Methylmalonyl-CoA

G→fumarate

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

G→oxaloacetate

Other

Cysteine metabolism	Cysteine sulfinic acid

Index of inborn errors of metabolism

Description	Metabolism Enzymes and pathways: citric acid cycle enzymes pentose phosphate intermediates glycoproteins enzymes glycosaminoglycans proteoglycan enzymes phospholipid metabolism cholesterol and steroid intermediates sphingolipids enzymes eicosanoids enzymes amino acid intermediates urea cycle enzymes nucleotide intermediates

Disorders	Citric acid cycle and electron transport chain Glycoprotein Proteoglycan Fatty-acid Phospholipid Cholesterol and steroid Eicosanoid Amino acid Purine-pyrimidine Heme metabolism Symptoms and signs

Treatment	Drugs other

Index of biochemical families

Carbohydrates	Alcohols Glycoproteins Glycosides

Lipids	Eicosanoids Fatty acids intermediates Glycerides Phospholipids Sphingolipids Steroids

Nucleic acids	Constituents intermediates

Proteins	Amino acids intermediates

Other	Tetrapyrroles intermediates

See also