Record Information
Version1.0
Creation date2011-09-21 00:15:52 UTC
Update date2015-07-21 06:57:15 UTC
Primary IDFDB022559
Secondary Accession NumbersNot Available
Chemical Information
FooDB 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) [HMDB]
CAS Number16597-58-3
Structure
Thumb
Synonyms
SynonymSource
2-Amino-3-carboxymuconate semialdehydeGenerator
2-amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioatehmdb
2-amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioic acidhmdb
2-Amino-3-(3-oxoprop-1-enyl)-but-2-enedioatehmdb
2-Amino-3-(3-oxoprop-1-enyl)-but-2-enedioic acidhmdb
2-amino-3-carboxymuconate semialdehydehmdb
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
Predicted Properties
PropertyValueSource
Water Solubility1.64 g/LALOGPS
logP-0.05ALOGPS
logP-3.7ChemAxon
logS-2ALOGPS
pKa (Strongest Acidic)2.38ChemAxon
pKa (Strongest Basic)6.72ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity43.62 m³·mol⁻¹ChemAxon
Polarizability16.01 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Chemical FormulaC7H7NO5
IUPAC name2-amino-3-(3-oxoprop-1-en-1-yl)but-2-enedioic acid
InChI IdentifierInChI=1S/C7H7NO5/c8-5(7(12)13)4(6(10)11)2-1-3-9/h1-3H,8H2,(H,10,11)(H,12,13)
InChI KeyKACPVQQHDVBVFC-UHFFFAOYSA-N
Isomeric SMILESNC(C(O)=O)=C(C=CC=O)C(O)=O
Average Molecular Weight185.1342
Monoisotopic Molecular Weight185.032422339
Classification
Description 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
  • 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 FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-5900000000-5678760d98b1c1aef0ddJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0076-1900000000-ac5d927ca2365b6ae1f5JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-5900000000-996af9cc34d138cdb97dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00kf-9200000000-ce06d4a9da9f0e145089JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-007o-2900000000-e08a15f38a790c0a8a8eJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-8900000000-f7aba3f0258e753f5128JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9200000000-70dfc7f87c3079551557JSpectraViewer
ChemSpider ID4444266
ChEMBL IDNot Available
KEGG Compound IDC04409
Pubchem Compound ID5280673
Pubchem Substance IDNot Available
ChEBI ID29044
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDHMDB01330
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID1445617
KNApSAcK IDNot Available
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
3-hydroxyanthranilate 3,4-dioxygenaseHAAOP46952
2-amino-3-carboxymuconate-6-semialdehyde decarboxylaseACMSDQ8TDX5
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063 map00380
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference