Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB110204
Identification
Name: aminocarboxymuconate semialdehyde
Description:The cis,cis-isomer of 2-amino-3-(3-oxoprop-1-enyl)but-2-enedioate.
Structure
Thumb
Synonyms:
  • 2-amino-3-carboxymuconate-6-semialdehyde
  • 2-amino-3-carboxymuconate semialdehyde
  • 2-amino-3-(3-oxoprop-1-en-1-yl)-but-2-enedioate
  • cis,cis-2-amino-3-(3-oxoprop-1-enyl)but-2-enedioate
Chemical Formula: C7H5NO5
Average Molecular Weight: 183.12
Monoisotopic Molecular Weight: 185.0324223404
InChI Key: KACPVQQHDVBVFC-OIFXTYEKSA-L
InChI: 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)/p-2/b2-1-,5-4-
CAS number: 16597-58-3
IUPAC Name:(2Z)-2-amino-3-[(1Z)-3-oxoprop-1-en-1-yl]but-2-enedioate
Traditional IUPAC Name: (2Z)-2-amino-3-[(1Z)-3-oxoprop-1-en-1-yl]but-2-enedioic acid
SMILES:C(=O)([O-])C(=C(C([O-])=O)N)C=CC=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of chemical entities 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).
Kingdom Chemical entities
Super ClassOrganic compounds
Class Organic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct Parent Alpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Branched fatty acid
  • Dicarboxylic acid or derivatives
  • Unsaturated fatty acid
  • Fatty acid
  • Fatty acyl
  • Vinylogous amide
  • Alpha,beta-unsaturated aldehyde
  • Enal
  • Amino acid
  • Carboxylic acid
  • Enamine
  • Organic oxide
  • Primary aliphatic amine
  • Organonitrogen compound
  • Organooxygen compound
  • Aldehyde
  • Primary amine
  • Carbonyl group
  • Organopnictogen compound
  • Organic oxygen compound
  • Amine
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aliphatic acyclic compound
Molecular Framework Aliphatic acyclic compounds
External Descriptors
  • 2-amino-3-(3-oxoprop-1-enyl)but-2-enedioic acid (CHEBI:995 )
Physical Properties
State: Solid
Charge:-2
Melting point: Not Available
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
Biological Properties
Cellular Locations: Not Available
Reactions:
Pathways:
Spectra
Spectra: Not Available
References
References:
  • 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 ]
  • 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 ]
  • 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 ]
  • Colabroy KL, Begley TP: Tryptophan catabolism: identification and characterization of a new degradative pathway. J Bacteriol. 2005 Nov;187(22):7866-9. [16267312 ]
Synthesis Reference: Not Available
Material Safety Data Sheet (MSDS) Not Available
External Links:
ResourceLink
ChEBI994
ChemSpider7822292
HMDBHMDB01330
KEGGC04409
MetaboLightsMTBLC994
PubChem9543319