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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:10 UTC
HMDB IDHMDB01280
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Aminomuconic acid semialdehyde
Description2-aminomuconic semialdehyde is an intermediate in the oxidative metabolism of tryptophan in mammals, and takes place via the kynurenine pathway, which is also used for NAD biosynthesis in all eukaryotic organisms. 2-Aminomuconic semialdehyde is reported to be unstable and spontaneously converted to picolinic acid (regarded as metabolically inert and is excreted in the urine as a glycine conjugate), and enzymatically converted to 2-aminomuconic acid through the action of 2-aminomuconic semialdehyde dehydrogenase. (PMID: 10510494 , 16267312 , 14275129 ).
Structure
Thumb
Synonyms
ValueSource
2-Aminomuconate 6-semialdehydeChEBI
2-Aminomuconate semialdehydeChEBI
2-Aminomuconic semialdehydeChEBI
2-Aminomuconic acid 6-semialdehydeGenerator
(2E,4Z)-2-amino-6-Oxohexa-2,4-dienoateGenerator
2-Aminomuconic acid semialdehydeGenerator
Chemical FormulaC6H7NO3
Average Molecular Weight141.1247
Monoisotopic Molecular Weight141.042593095
IUPAC Name(2E,4Z)-2-amino-6-oxohexa-2,4-dienoic acid
Traditional Name2-aminomuconic semialdehyde
CAS Registry Number245128-91-0
SMILES
N\C(=C\C=C/C=O)C(O)=O
InChI Identifier
InChI=1S/C6H7NO3/c7-5(6(9)10)3-1-2-4-8/h1-4H,7H2,(H,9,10)/b2-1-,5-3+
InChI KeyInChIKey=QCGTZPZKJPTAEP-REDYYMJGSA-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
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Monocarboxylic acid or derivatives
  • Enamine
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
Biofunction
  • Component of Tryptophan metabolism
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 Solubility5.9 mg/mLALOGPS
logP-0.14ALOGPS
logP-3.1ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)2.76ChemAxon
pKa (Strongest Basic)7.72ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area80.39 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity37.63 m3·mol-1ChemAxon
Polarizability12.96 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
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063map00380
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 IDFDB022532
KNApSAcK IDNot Available
Chemspider ID4444230
KEGG Compound IDC03824
BioCyc ID2-AMINOMUCONATE_SEMIALDEHYDE
BiGG ID1445635
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01280
Metagene LinkHMDB01280
METLIN ID6133
PubChem Compound5280625
PDB IDNot Available
ChEBI ID15745
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. He Z, Spain J: Preparation of 2-aminomuconate from 2-aminophenol by coupled enzymatic dioxygenation and dehydrogenation reactions. J Ind Microbiol Biotechnol. 1999 Aug;23(2):138-142. [10510494 ]
  2. NISHIZUKA Y, ICHIYAMA A, GHOLSON RK, HAYAISHI O: STUDIES ON THE METABOLISM OF THE BENZENE RING OF TRYPTOPHAN IN MAMMALIAN TISSUES. I. ENZYMIC FORMATION OF GLUTARIC ACID FROM 3-HYDROXYANTHRANILIC ACID. J Biol Chem. 1965 Feb;240:733-9. [14275129 ]
  3. Colabroy KL, Begley TP: Tryptophan catabolism: identification and characterization of a new degradative pathway. J Bacteriol. 2005 Nov;187(22):7866-9. [16267312 ]

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
Reactions
2-Amino-3-carboxymuconic acid semialdehyde → 2-Aminomuconic acid semialdehyde + CO(2)details
2-Amino-3-carboxymuconic acid semialdehyde → 2-Aminomuconic acid semialdehyde + Carbon dioxidedetails