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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:04 UTC
HMDB IDHMDB01241
Secondary Accession Numbers
  • HMDB02018
Metabolite Identification
Common Name2-Aminomuconic acid
Description2-Aminomuconic acid is a product of the Tryptophan metabolism degradation pathway (kinurenine pathway), in a reaction catabolized by the enzyme aminocarboxymuconate semialdehyde decarboxylase [EC:4.1.1.45]. The kynurenine pathway is the major route of L-tryptophan degradation in mammals. (BioCyc).
Structure
Thumb
Synonyms
ValueSource
2-Aminohexa-2,4-dienedioateHMDB
2-Aminohexa-2,4-dienedioic acidHMDB
2-AminomuconateHMDB
O-AminomuconateHMDB
Chemical FormulaC6H7NO4
Average Molecular Weight157.1241
Monoisotopic Molecular Weight157.037507717
IUPAC Name(2Z,4E)-5-aminohexa-2,4-dienedioic acid
Traditional Name2-aminomuconate semialdehyde
CAS Registry Number4548-99-6
SMILES
N\C(=C\C=C/C(O)=O)C(O)=O
InChI Identifier
InChI=1S/C6H7NO4/c7-4(6(10)11)2-1-3-5(8)9/h1-3H,7H2,(H,8,9)(H,10,11)/b3-1-,4-2+
InChI KeyInChIKey=ZRHONLCTYUYMIQ-HSFFGMMNSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as alpha amino acids. These are amino acids in which the amino group is attached to the carbon atom immediately adjacent to the carboxylate group (alpha carbon).
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassAmino acids, peptides, and analogues
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Enamine
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Protein synthesis, amino acid biosynthesis
ApplicationNot Available
Cellular locations
  • Cytoplasm
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility2.75 mg/mLALOGPS
logP-0.05ALOGPS
logP-3.1ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)2.58ChemAxon
pKa (Strongest Basic)8.37ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area100.62 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.55 m3·mol-1ChemAxon
Polarizability14.02 Å3ChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDFDB022507
KNApSAcK IDNot Available
Chemspider ID4444139
KEGG Compound IDC02220
BioCyc ID2-AMINO-MUCONATE
BiGG ID1445654
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01241
Metagene LinkHMDB01241
METLIN ID321
PubChem Compound5280499
PDB IDNot Available
ChEBI ID15745
References
Synthesis ReferenceHe, Z.; Spain, J. C. Preparation of 2-aminomuconate from 2-aminophenol by coupled enzymatic dioxygenation and dehydrogenation reactions. Journal of Industrial Microbiology & Biotechnology (1999), 23(2), 138-142.
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in catalytic activity
Specific function:
Converts alpha-amino-beta-carboxymuconate-epsilon-semialdehyde (ACMS) to alpha-aminomuconate semialdehyde (AMS). ACMS can be converted non-enzymatically to quinolate (QA), a key precursor of NAD, and a potent endogenous excitotoxin of neuronal cells which is implicated in the pathogenesis of various neurodegenerative disorders. In the presence of ACMSD, ACMS is converted to AMS, a benign catabolite. ACMSD ultimately controls the metabolic fate of tryptophan catabolism along the kynurenine pathway.
Gene Name:
ACMSD
Uniprot ID:
Q8TDX5
Molecular weight:
38035.045