Showing Metabocard for 4-maleylacetoacetate (BASm0000845)

Common Name4-maleylacetoacetate
DescriptionMaleylacetoacetic acid, also known as 4-maleylacetoacetate, is an intermediate in the metabolism of tyrosine. Homogentisate 1,2-dioxygenase (HGD) is the enzyme which catalyzes the conversion of homogentisate into 4-maleylacetoacetate. HGD is involved in the catabolism of aromatic rings, more specifically in the breakdown of the amino acids tyrosine and phenylalanine.
Structure
Molecular FormulaC8H8O6
Average Mass200.14550
Monoisotopic Mass200.03209
IUPAC Name(2Z)-4,6-dioxooct-2-enedioic acid
Traditional NameMaleylacetoacetic acid
CAS Registry Number5698-52-2
SMILESO=C([O-])/C=C\C(=O)CC(=O)CC(=O)[O-]
InChI IdentifierInChI=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-
InChI KeyGACSIVHAIFQKTC-UPHRSURJSA-N
CHEBI IDCHEBI:17105
HMDB IDHMDB0002052
Pathways
NameSMPDB/PathBank
Tyrosine metabolism
Phenylalanine and Tyrosine Metabolism
Alkaptonuria
Hawkinsinuria
Phenylketonuria
Tyrosinemia Type I
Tyrosinemia Type 2 (or Richner-Hanhart syndrome)
Tyrosinemia Type 3 (TYRO3)
Disulfiram Action Pathway
Tyrosinemia, transient, of the newborn
Dopamine beta-hydroxylase deficiency
Monoamine oxidase-a deficiency (MAO-A)
StateSolid
Water Solubility1.65e+00 g/l
logP-0.19
logS-2.08
pKa (Strongest Acidic)2.72
pKa (Strongest Basic)-7.06
Hydrogen Acceptor Count6
Hydrogen Donor Count2
Polar Surface Area108.74 Ų
Rotatable Bond Count6
Physiological Charge-2
Formal Charge0
Refractivity44.40 m³·mol⁻¹
Polarizability16.75

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