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Record Information
Version3.6
Creation Date2005-11-16 15:48:42 UTC
Update Date2016-02-11 01:04:17 UTC
HMDB IDHMDB01330
Secondary Accession NumbersNone
Metabolite Identification
Common Name2-Amino-3-carboxymuconic acid semialdehyde
Description2-amino-3-carboxymuconic acid semialdehyde is an intermediate metabolite of the tryptophan-niacin catabolic pathway. Current interest in the degradation of tryptophan is mostly due to the role of quinolinate and other metabolites in several neuropathological conditions. Quinolinate is a neurotoxin formed nonenzymatically from 2-amino-3-carboxymuconic semialdehyde in mammalian tissues. 2-Amino-3-carboxymuconic semialdehyde is enzymatically converted to 2-aminomuconate via 2-aminomuconic semialdehyde. (PMID: 10510494 , 16267312 , 14275129 ).
Structure
Thumb
Synonyms
ValueSource
2-amino-3-(3-Oxoprop-1-en-1-yl)but-2-enedioateChEBI
2-amino-3-(3-Oxoprop-1-enyl)-but-2-enedioateChEBI
2-amino-3-Carboxymuconate semialdehydeChEBI
2-amino-3-(3-Oxoprop-1-en-1-yl)but-2-enedioic acidGenerator
2-amino-3-(3-Oxoprop-1-enyl)-but-2-enedioic acidHMDB
2-amino-3-Carboxymuconate-6-semialdehydeHMDB
ACSHMDB
amino-3-(3-Oxoprop-1-en-1-yl)but-2-enedioateHMDB
amino-3-(3-Oxoprop-1-en-1-yl)but-2-enedioic acidHMDB
Chemical FormulaC7H7NO5
Average Molecular Weight185.1342
Monoisotopic Molecular Weight185.032422339
IUPAC Name(2Z)-2-amino-3-[(1Z)-3-oxoprop-1-en-1-yl]but-2-enedioic acid
Traditional Name(2Z)-2-amino-3-[(1Z)-3-oxoprop-1-en-1-yl]but-2-enedioic acid
CAS Registry Number16597-58-3
SMILES
N\C(C(O)=O)=C(\C=C/C=O)/C(O)=O
InChI Identifier
InChI=1S/C7H7NO5/c8-5(7(12)13)4(6(10)11)2-1-3-9/h1-3H,8H2,(H,10,11)(H,12,13)/b2-1-,5-4-
InChI KeyInChIKey=KACPVQQHDVBVFC-OIFXTYEKSA-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
  • Branched fatty acid
  • Amino fatty acid
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Dicarboxylic acid or derivatives
  • Vinylogous amide
  • Enal
  • Alpha,beta-unsaturated aldehyde
  • Enamine
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aldehyde
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
  • 2-amino-3-(3-oxoprop-1-enyl)but-2-enedioic acid (CHEBI:995 )
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 Solubility1.64 mg/mLALOGPS
logP-0.05ALOGPS
logP-3.7ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)2.38ChemAxon
pKa (Strongest Basic)6.72ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.69 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity43.62 m3·mol-1ChemAxon
Polarizability15.72 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 Location
  • Brain
  • Kidney
  • Liver
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 IDFDB022559
KNApSAcK IDNot Available
Chemspider ID4444266
KEGG Compound IDC04409
BioCyc ID2-AMINO-3-CARBOXYMUCONATE_SEMIAL
BiGG ID1445617
Wikipedia LinkNot Available
NuGOwiki LinkHMDB01330
Metagene LinkHMDB01330
METLIN ID6165
PubChem Compound5280673
PDB IDNot Available
ChEBI ID995
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Ftukijwatari T, Murakami M, Ohta M, Kimura N, Jin-No Y, Sasaki R, Shibata K: Changes in the urinary excretion of the metabolites of the tryptophan-niacin pathway during pregnancy in Japanese women and rats. J Nutr Sci Vitaminol (Tokyo). 2004 Dec;50(6):392-8. [15895513 ]
  2. 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 ]
  3. 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 ]
  4. 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
General function:
Involved in 3-hydroxyanthranilate 3,4-dioxygenase activity
Specific function:
Catalyzes the oxidative ring opening of 3-hydroxyanthranilate to 2-amino-3-carboxymuconate semialdehyde, which spontaneously cyclizes to quinolinate.
Gene Name:
HAAO
Uniprot ID:
P46952
Molecular weight:
32555.935
Reactions
3-Hydroxyanthranilic acid + Oxygen → 2-Amino-3-carboxymuconic acid semialdehydedetails