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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2005-11-16 15:48:42 UTC
Update Date2020-02-26 21:22:48 UTC
HMDB IDHMDB0000978
Secondary Accession Numbers
  • HMDB00978
Metabolite Identification
Common Name4-(2-Aminophenyl)-2,4-dioxobutanoic acid
Description4-(2-Aminophenyl)-2,4-dioxobutanoic acid, also known as 2-amino-alpha,gamma-dioxobenzenebutanoic 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-Aminophenyl)-2,4-dioxobutanoic acid is a strong basic compound (based on its pKa). 4-(2-Aminophenyl)-2,4-dioxobutanoic acid is a substrate for Kynurenine/alpha-aminoadipate aminotransferase mitochondrial. 4-(2-Aminophenyl)-2,4-dioxobutanoic acid exists in all living species, ranging from bacteria to humans. 4-(2-aminophenyl)-2,4-dioxobutanoic acid and L-glutamic acid can be biosynthesized from L-kynurenine and oxoglutaric acid through the action of the enzyme kynurenine/alpha-aminoadipate aminotransferase, mitochondrial. In humans, 4-(2-aminophenyl)-2,4-dioxobutanoic acid is involved in tryptophan metabolism.
Structure
Data?1582752168
Synonyms
ValueSource
4-(2-Aminophenyl)-2,4-dioxobutanoateChEBI
4-(2-Aminophenyl)-2,4-dioxo-butanoateHMDB
4-(2-Aminophenyl)-2,4-dioxo-butanoic acidHMDB
2-Amino-alpha,gamma-dioxobenzenebutanoic acidHMDB
2-Amino-α,γ-dioxobenzenebutanoic acidHMDB
4-(2-Aminophenyl)-2,4-dioxobutanoic acidHMDB
Chemical FormulaC10H9NO4
Average Molecular Weight207.1828
Monoisotopic Molecular Weight207.053157781
IUPAC Name4-(2-aminophenyl)-2,4-dioxobutanoic acid
Traditional Name4-(2-aminophenyl)-2,4-dioxobutanoic acid
CAS Registry Number90924-76-8
SMILES
NC1=C(C=CC=C1)C(=O)CC(=O)C(O)=O
InChI Identifier
InChI=1S/C10H9NO4/c11-7-4-2-1-3-6(7)8(12)5-9(13)10(14)15/h1-4H,5,11H2,(H,14,15)
InChI KeyCAOVWYZQMPNAFJ-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
  • Benzoyl
  • Gamma-keto acid
  • Aryl alkyl ketone
  • Aniline or substituted anilines
  • 1,3-diketone
  • Monocyclic benzene moiety
  • Alpha-keto acid
  • Keto acid
  • 1,3-dicarbonyl compound
  • Benzenoid
  • Alpha-hydroxy ketone
  • Vinylogous amide
  • Amino acid
  • Amino acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Primary amine
  • Organonitrogen compound
  • Organic nitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Source:

Biological location:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.56 g/LALOGPS
logP0.91ALOGPS
logP1ChemAxon
logS-2.6ALOGPS
pKa (Strongest Acidic)1.96ChemAxon
pKa (Strongest Basic)3.34ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area97.46 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity52.85 m³·mol⁻¹ChemAxon
Polarizability19.32 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available146.84531661259
DarkChem[M-H]-PredictedNot Available144.47731661259
AllCCS[M+H]+PredictedNot Available144.88732859911
AllCCS[M-H]-PredictedNot Available142.76232859911

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,1TMS,#11986.2935https://arxiv.org/abs/1905.12712
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,1TMS,#22158.7383https://arxiv.org/abs/1905.12712
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,1TMS,#32094.551https://arxiv.org/abs/1905.12712
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,1TBDMS,#12242.1084https://arxiv.org/abs/1905.12712
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,1TBDMS,#22417.7834https://arxiv.org/abs/1905.12712
4-(2-Aminophenyl)-2,4-dioxobutanoic acid,1TBDMS,#32361.4265https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02ml-9600000000-9ee4bc222cfbefcf71672016-09-22View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-6940000000-0a58537f3d042b452b9a2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-02ml-9600000000-3990142e51ce8e1ed9aa2021-09-05View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-1490000000-82e91d56bdce0e09cb732015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08fr-4930000000-4e754ee43c0a1b2177382015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9400000000-ff4da0a8b66f352cf30d2015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0002-3920000000-ed3ee349719d218822192021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-9200000000-5a28b87fef7bde9d37c82021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0006-9000000000-5761d11f372a2a30748f2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0ab9-0950000000-f6e0367966abff1dc8732015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-0900000000-a2c601ca3bb3e2f03be22015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9500000000-7dd33609488e645968362015-09-15View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-08mi-2930000000-680696b189e40364b3e12021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-00di-2900000000-e522d34ea0481d109d3e2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9000000000-ee62e52b5df8d4bab6ff2021-09-08View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedChildren (1-13 years old)BothEnthesitis-related arthritis details
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB022348
KNApSAcK IDNot Available
Chemspider ID459
KEGG Compound IDC01252
BioCyc IDNot Available
BiGG ID37199
Wikipedia LinkNot Available
METLIN ID5916
PubChem Compound472
PDB IDNot Available
ChEBI ID17442
Food Biomarker OntologyNot Available
VMH ID4APHDOB
MarkerDB 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:
Catalyzes the irreversible transamination of the L-tryptophan metabolite L-kynurenine to form kynurenic acid (KA). Plays a key role in amino acid metabolism. Important for metabolite exchange between mitochondria and cytosol. Facilitates cellular uptake of long-chain free fatty acids.
Gene Name:
GOT2
Uniprot ID:
P00505
Molecular weight:
47517.285
Reactions
L-Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + L-Glutamic aciddetails
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-Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-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-Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-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-Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + L-Glutamic aciddetails
L-Kynurenine + Glyoxylic acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + Glycinedetails