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Record Information
Version3.6
Creation Date2006-08-13 10:31:08 UTC
Update Date2017-08-16 04:14:56 UTC
HMDB IDHMDB0004083
Secondary Accession Numbers
  • HMDB04083
Metabolite Identification
Common Name4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid
Description4-(2 Amino-3-hydroxyphenyl)-2,4-dioxobutanoate is found in the tryptophan metabolic pathway and is an intermediate in tryptophan degradation [Kegg: C05645]. More specifically it is an intermediate in the conversion of 3-hydroxy-L-kynurenine to xanthurenate. The conversion is catalyzed by kynurenine aminotransferase (EC 2.6.1.7).
Structure
Thumb
Synonyms
ValueSource
4-(2-amino-3-Hydroxyphenyl)-2,4-dioxobutanoateHMDB
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
DescriptionThis compound belongs to the class of chemical entities known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomChemical entities
Super ClassOrganic compounds
ClassOrganic oxygen compounds
Sub ClassOrganooxygen compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Butyrophenone
  • Gamma-keto acid
  • Benzoyl
  • Aryl alkyl ketone
  • Aniline or substituted anilines
  • Aminophenol
  • O-aminophenol
  • 1,3-diketone
  • 1-hydroxy-4-unsubstituted benzenoid
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • Keto acid
  • Alpha-keto acid
  • Benzenoid
  • 1,3-dicarbonyl compound
  • Primary aromatic amine
  • Monocyclic benzene moiety
  • Vinylogous amide
  • Alpha-hydroxy ketone
  • Amino acid
  • Amino acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid derivative
  • Carboxylic acid
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusDetected 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
Water Solubility0.71 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.83 m3·mol-1ChemAxon
Polarizability20.13 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular LocationsNot Available
Biofluid Locations
  • Feces
Tissue LocationNot Available
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063map00380
Normal Concentrations
Not Available
Abnormal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
FecesDetected but not Quantified Children (6 - 18 years old)Bothenthesitis-related arthritis details
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 IDFDB023305
KNApSAcK IDNot Available
Chemspider ID389612
KEGG Compound IDC05645
BioCyc IDNot Available
BiGG ID46189
Wikipedia LinkNot Available
NuGOwiki LinkHMDB0004083
METLIN IDNot Available
PubChem Compound440741
PDB IDNot Available
ChEBI IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in transferase activity, transferring nitrogenous groups
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).
Gene Name:
AADAT
Uniprot ID:
Q8N5Z0
Molecular weight:
47351.17
Reactions
L-3-Hydroxykynurenine + Oxoglutaric acid → 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid + L-Glutamic aciddetails
General function:
Involved in 1-aminocyclopropane-1-carboxylate synthase activity
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Metabolizes the cysteine conjugates of certain halogenated alkenes and alkanes to form reactive metabolites. Catalyzes the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond.
Gene Name:
CCBL1
Uniprot ID:
Q16773
Molecular weight:
47874.765
Reactions
L-3-Hydroxykynurenine + Oxoglutaric acid → 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid + L-Glutamic aciddetails
General function:
Transcription
Specific function:
Not Available
Gene Name:
AADAT
Uniprot ID:
Q4W5N8
Molecular weight:
47351.2
General function:
Involved in transferase activity, transferring nitrogenous groups
Specific function:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). May catalyze the beta-elimination of S-conjugates and Se-conjugates of L-(seleno)cysteine, resulting in the cleavage of the C-S or C-Se bond (By similarity). Has transaminase activity towards L-kynurenine, tryptophan, phenylalanine, serine, cysteine, methionine, histidine, glutamine and asparagine with glyoxylate as an amino group acceptor (in vitro). Has lower activity with 2-oxoglutarate as amino group acceptor (in vitro) (By similarity).
Gene Name:
CCBL2
Uniprot ID:
Q6YP21
Molecular weight:
51399.855
Reactions
L-3-Hydroxykynurenine + Oxoglutaric acid → 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid + L-Glutamic aciddetails