Showing metabocard for 2-Aminomuconic acid semialdehyde (BMDB0001280)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 22:43:34 UTC
Update Date2020-05-19 22:01:23 UTC
BMDB IDBMDB0001280
Secondary Accession Numbers
  • BMDB01280
Metabolite Identification
Common Name2-Aminomuconic acid semialdehyde
Description2-Aminomuconic acid semialdehyde 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). 2-Aminomuconic acid semialdehyde is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. 2-Aminomuconic acid semialdehyde exists in all living organisms, ranging from bacteria to humans. 2-Aminomuconic acid semialdehyde can be biosynthesized from 2-amino-3-carboxymuconic acid semialdehyde; which is catalyzed by the enzyme 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase. In cattle, 2-aminomuconic acid semialdehyde is involved in the metabolic pathway called the tryptophan metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
2-Aminomuconate 6-semialdehydeChEBI
2-Aminomuconate semialdehydeChEBI
2-Aminomuconic semialdehydeChEBI
2-Aminomuconic acid 6-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 KeyQCGTZPZKJPTAEP-REDYYMJGSA-N
Chemical Taxonomy
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
  • Fatty acyl
  • Fatty acid
  • Unsaturated fatty acid
  • Alpha,beta-unsaturated aldehyde
  • Enal
  • Amino acid
  • Carboxylic acid
  • Enamine
  • Monocarboxylic acid or derivatives
  • Aldehyde
  • Organonitrogen compound
  • Organooxygen compound
  • Primary aliphatic amine
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Organopnictogen compound
  • Amine
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
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
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 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity37.63 m³·mol⁻¹ChemAxon
Polarizability12.96 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
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, Positivesplash10-014m-9200000000-6fd74f95ac9e06d815d8View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0002-9200000000-c20041baa79945f5d800View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0095-7900000000-d57e751610237d25aaf4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-002b-9100000000-82f13963addf5ffc0e16View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gb9-9000000000-9c9844252423065acedaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-1900000000-49ad8b8a0c9588a39938View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-006x-6900000000-77aa0f01bf2a2c535794View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9100000000-9bd7a5539e729542e8f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0002-9100000000-7831b7cf7af8efc10bc2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-017j-9000000000-1067cced8ab6220283a7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014i-9000000000-3febc896ed7c770666d0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0007-9500000000-770609a188bfdc543692View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-014i-9100000000-8ede36ee93f2e80508d3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014l-9000000000-224bae95c47132912d4dView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0001280
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022532
KNApSAcK IDC00007492
Chemspider ID4444230
KEGG Compound IDC03824
BioCyc IDNot Available
BiGG ID1445635
Wikipedia LinkNot Available
METLIN ID6133
PubChem Compound5280625
PDB IDNot Available
ChEBI ID15745
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. 2-amino-3-carboxymuconate-6-semialdehyde decarboxylase
General function:
Involved in aminocarboxymuconate-semialdehyde decarboxy
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 (By similarity).
Gene Name:
ACMSD
Uniprot ID:
Q0II68
Molecular weight:
37923.0
Reactions
2-Amino-3-carboxymuconic acid semialdehyde → 2-Aminomuconic acid semialdehyde + Carbon dioxidedetails