4-Maleylacetoacetate

4-Maleylacetoacetate: 4-Maleylacetoacetate

IUPAC name

(Z)-4,6-dioxooct-2-enedioic acid

Identifiers

CAS number 5698-52-2

PubChem 5280393

ChemSpider 4444078^Y

KEGG C01036^Y

ChEBI CHEBI:47904^Y

Jmol-3D images Image 1

SMILES

O=C(/C=C\C(=O)O)CC(=O)CC(=O)O

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

Properties

Molecular formula C₈H₈O₆

Molar mass 200.146 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

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

See also

Homogentisate 1,2-dioxygenase

v · Amino acid metabolism metabolic intermediates

K→acetyl-CoA

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

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)

biochemical families: prot · nucl · carb (glpr, alco, glys) · lipd (fata/i, phld, strd, gllp, eico) · amac/i · ncbs/i · ttpy/i

Categories:
Carboxylic acids
Ketones
Biochemistry stubs

4-Maleylacetoacetate

IUPAC name (Z)-4,6-dioxooct-2-enedioic acid
Identifiers
CAS number	5698-52-2
PubChem	5280393
ChemSpider	4444078^Y
KEGG	C01036^Y
ChEBI	CHEBI:47904^Y
Jmol-3D images	Image 1
SMILES O=C(/C=C\C(=O)O)CC(=O)CC(=O)O
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
Properties
Molecular formula	C₈H₈O₆
Molar mass	200.146 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

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Maleylacetoacetate isomerase — Identifiers EC number 5.2.1.2 CAS number 9023 75 0 … Wikipedia
maleylacetoacetate isomerase — ma·le·yl·ace·to·ac·e·tate isom·er·ase (ma″le əl ə se″to asґə tāt i somґər ās) [EC 5.2.1.2] an enzyme of the isomerase class that catalyzes the interconversion of the isomers 4 maleylacetoacetate and 4… … Medical dictionary
maleylacetoacetate — noun An intermediate in the metabolism of tyrosine … Wiktionary
maleylacetoacetate — An intermediate in l phenylalanine and l tyrosine catabolism; accumulates in certain inherited disorders of tyrosine metabolism. m. cis,trans isomerase an enzyme that catalyzes the reversible conversion of m. to 4 fumarylacetoacetate; an enzyme… … Medical dictionary
4-maleylacetoacetate — 4 ma·le·yl·ace·to·ac·e·tate (ma″le əl ə se″to asґə tāt) an isomer of fumarylacetoacetate, formed by oxidation of homogentisate in the degradation of tyrosine and phenylalanine … Medical dictionary
GSTZ1 — Glutathione transferase zeta 1 (maleylacetoacetate isomerase), also known as GSTZ1, is a human gene.cite web | title = Entrez Gene: GSTZ1 glutathione transferase zeta 1 (maleylacetoacetate isomerase)| url =… … Wikipedia
Homogentisate 1,2-dioxygenase — protein Name=homogentisate 1,2 dioxygenase (homogentisate oxidase) caption= 3D rendering of Homogentisate Dioxygenase with active site amino acid residues and Iron atom colored. Histidine is the tan color, Glutamate the red color, and Iron is the … Wikipedia
Tyrosine — NatOrganicBox name=( S ) 2 Amino 3 (4 hydroxyphenyl) propanoic acid PubChem = 1153 CAS = 60 18 4 SMILES = N [C@@H] (Cc1ccc(O)cc1)C(O)=O C=9 | H=11 | N=1 | O=3 mass=181.19 g/molTyrosine (abbreviated as Tyr or Y) [cite web | author=IUPAC IUBMB… … Wikipedia
Glycine — For the plant, see Glycine (plant). Glycine[1] … Wikipedia
Phenylalanine — Phe redirects here. For other uses, see Phe (disambiguation). Phenylalanine … Wikipedia

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4-Maleylacetoacetate

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4-Maleylacetoacetate

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