Showing metabocard for 2-Amino-3-carboxymuconic acid semialdehyde (BMDB0001330)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (2) Show 2 proteinsXML
Record Information
Version1.0
Creation Date2016-09-30 22:44:15 UTC
Update Date2020-05-19 22:01:23 UTC
BMDB IDBMDB0001330
Secondary Accession Numbers
  • BMDB01330
Metabolite Identification
Common Name2-Amino-3-carboxymuconic acid semialdehyde
Description2-Amino-3-carboxymuconic acid semialdehyde, also known as 2-amino-3-carboxymuconic acid semialdehyde or ACS, 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-Amino-3-carboxymuconic acid semialdehyde is possibly soluble (in water) and a very strong basic compound (based on its pKa). 2-Amino-3-carboxymuconic acid semialdehyde exists in all living species, ranging from bacteria to humans. 2-Amino-3-carboxymuconic acid semialdehyde participates in a number of enzymatic reactions, within cattle. In particular, 2-Amino-3-carboxymuconic acid semialdehyde can be biosynthesized from 3-hydroxyanthranilic acid; which is mediated by the enzyme 3,4-dihydroxyphenylacetaldehyde. In addition, 2-Amino-3-carboxymuconic acid semialdehyde can be converted into 2-aminomuconic acid semialdehyde through the action of the enzyme 2-amino-3-carboxymuconic acid semialdehyde decarboxylase. In cattle, 2-amino-3-carboxymuconic acid semialdehyde is involved in the metabolic pathway called the tryptophan metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
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 acidGenerator
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 KeyKACPVQQHDVBVFC-OIFXTYEKSA-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
  • 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
  • 2-amino-3-(3-oxoprop-1-enyl)but-2-enedioic acid (CHEBI:995 )
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-0.05ALOGPS
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
Polarizability15.75 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, Positivesplash10-01ox-4900000000-62ebd57b1dadb165bc36View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0300-8793000000-3b592a4ef216b8fdf12eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00r6-0900000000-0a2ef2dbb21b597d6fc4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00dl-4900000000-53b3810106e9c56f7d0aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014l-9100000000-fa0ffd8141b90a020246View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ec-1900000000-590832d218cda44b13f8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0229-5900000000-74f5fb374736aa527071View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00dl-9300000000-84211b6b70277d6fb146View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-5900000000-210673f89c9ac4437575View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01oy-8900000000-1eabc10d32130d827b37View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-9200000000-3900709db9f9f0db1c3bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00kf-0900000000-1ac99f0053d2cc748f29View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03kc-2900000000-f5ecf269380d030c89a9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-066u-9100000000-df3d348bf5ff10948d70View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Brain
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BrainExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
KidneyExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
LiverExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal
  • Not Applicable
 details
Abnormal Concentrations
Not Available
HMDB IDHMDB0001330
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022559
KNApSAcK IDNot Available
Chemspider ID4444266
KEGG Compound IDC04409
BioCyc IDNot Available
BiGG ID1445617
Wikipedia LinkNot Available
METLIN ID6165
PubChem Compound5280673
PDB IDNot Available
ChEBI ID995
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
Enzyme Details
2. 3-hydroxyanthranilate 3,4-dioxygenase
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:
Q0VCA8
Molecular weight:
32493.0
Reactions
3-Hydroxyanthranilic acid + Oxygen → 2-Amino-3-carboxymuconic acid semialdehydedetails