Showing metabocard for 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid (BMDB0004083)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:07:47 UTC
Update Date2020-05-21 16:28:50 UTC
BMDB IDBMDB0004083
Secondary Accession Numbers
  • BMDB04083
Metabolite Identification
Common Name4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid
Description4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group. 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid is possibly soluble (in water) and a strong basic compound (based on its pKa). 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid and L-glutamic acid can be biosynthesized from L-3-hydroxykynurenine and oxoglutaric acid through its interaction with the enzyme kynurenine/alpha-aminoadipate aminotransferase, mitochondrial. In cattle, 4-(2-amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid is involved in the metabolic pathway called the tryptophan metabolism pathway.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-Amino-3-hydroxy-alpha,gamma-dioxobenzenebutanoic acidChEBI
2-Amino-3-hydroxy-a,g-dioxobenzenebutanoateGenerator
2-Amino-3-hydroxy-a,g-dioxobenzenebutanoic acidGenerator
2-Amino-3-hydroxy-alpha,gamma-dioxobenzenebutanoateGenerator
2-Amino-3-hydroxy-α,γ-dioxobenzenebutanoateGenerator
2-Amino-3-hydroxy-α,γ-dioxobenzenebutanoic acidGenerator
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoateGenerator
Chemical FormulaC10H9NO5
Average Molecular Weight223.1822
Monoisotopic Molecular Weight223.048072403
IUPAC Name4-(2-amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid
Traditional Name4-(2-amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid
CAS Registry NumberNot Available
SMILES
NC1=C(C=CC=C1O)C(=O)CC(=O)C(O)=O
InChI Identifier
InChI=1S/C10H9NO5/c11-9-5(2-1-3-6(9)12)7(13)4-8(14)10(15)16/h1-3,12H,4,11H2,(H,15,16)
InChI KeyYCJNYHCCOXVYAF-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Butyrophenone
  • Gamma-keto acid
  • O-aminophenol
  • Aryl alkyl ketone
  • Aniline or substituted anilines
  • Aminophenol
  • Benzoyl
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1,3-diketone
  • Keto acid
  • Benzenoid
  • 1,3-dicarbonyl compound
  • Alpha-keto acid
  • Monocyclic benzene moiety
  • Vinylogous amide
  • Alpha-hydroxy ketone
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Primary amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Amine
  • Organonitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locationsNot Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.273Not Available
Predicted Properties
PropertyValueSource
logP0.91ALOGPS
logP0.44ChemAxon
logS-2.5ALOGPS
pKa (Strongest Acidic)1.9ChemAxon
pKa (Strongest Basic)3.34ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area117.69 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.83 m³·mol⁻¹ChemAxon
Polarizability20.13 ųChemAxon
Number of Rings1ChemAxon
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, Positivesplash10-0553-7910000000-894d2b28fa25786b8cf4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9384000000-d85d64127c1a306053b0View 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, Positivesplash10-0abi-0690000000-607a25e04b41184c2e11View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0910000000-f6e7ca1f649c7d85f1c8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052u-9800000000-9abd1533cae37b5a1e31View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2290000000-db5113faa78a8f868817View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fi0-2940000000-5c30994df2e0c448d78fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-4900000000-5c2c2b7f0e47291f345dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056r-0900000000-98462e5bccca7cad48a3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-fd75faf4a2b73326af8eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-4900000000-564c7472238de91e0b05View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0930000000-b4c5ebc1b69491058158View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ri-2900000000-6b672118eb0609fb3d7eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-9300000000-ee7e4c997d23d017bcb6View in MoNA
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0004083
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB023305
KNApSAcK IDNot Available
Chemspider ID389612
KEGG Compound IDC05645
BioCyc IDNot Available
BiGG ID46189
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound440741
PDB IDNot Available
ChEBI ID27593
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial
General function:
Transcription
Specific function:
Transaminase with broad substrate specificity. Has transaminase activity towards aminoadipate, kynurenine, methionine and glutamate. Shows activity also towards tryptophan, aspartate and hydroxykynurenine. Accepts a variety of oxo-acids as amino-group acceptors, with a preference for 2-oxoglutarate, 2-oxocaproic acid, phenylpyruvate and alpha-oxo-gamma-methiol butyric acid. Can also use glyoxylate as amino-group acceptor (in vitro) (By similarity).
Gene Name:
AADAT
Uniprot ID:
Q5E9N4
Molecular weight:
47901.0
Reactions
L-3-Hydroxykynurenine + Oxoglutaric acid → 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid + L-Glutamic aciddetails