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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2017-12-07 01:23:29 UTC
HMDB IDHMDB0001241
Secondary Accession Numbers
  • HMDB01241
  • 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 KeyZRHONLCTYUYMIQ-HSFFGMMNSA-N
Chemical 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).
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic acids and derivatives
Sub ClassCarboxylic acids and derivatives
Direct ParentAlpha amino acids
Alternative Parents
Substituents
  • Alpha-amino acid
  • Medium-chain fatty acid
  • Amino fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Amino acid
  • Carboxylic acid
  • Enamine
  • Organic nitrogen compound
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Carbonyl group
  • Organic oxygen compound
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

Source:

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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity38.55 m³·mol⁻¹ChemAxon
Polarizability14.02 ųChemAxon
Number of Rings0ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03di-9700000000-a02dd1685716821aa4f1View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-059x-7090000000-6963e3c60b61bb49a7a6View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-1900000000-9c0b51071c5840183531View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03xu-9500000000-afa722c2f915ae073b5fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9000000000-d0dcb39fc65e9f5986a1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-75f020ed8baa43f11f5bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-06ri-2900000000-a31ac1979cd158a8444cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9300000000-69085f63816d86fa5f1cView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biofluid LocationsNot Available
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
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
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