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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2006-08-13 10:31:08 UTC
Update Date2020-02-26 21:24:57 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-dioxobutanoic acid, also known as 2-amino-3-hydroxy-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. In humans, 4-(2-amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid is involved in the tryptophan metabolism pathway. 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid has been detected, but not quantified in, a few different foods, such as anatidaes (Anatidae), chickens (Gallus gallus), and domestic pigs (Sus scrofa domestica). This could make 4-(2-amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid a potential biomarker for the consumption of these foods. 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on 4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid.
Structure
Data?1582752297
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 Number857760-67-9
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
Disposition

Biological location:

Source:

Process

Naturally occurring process:

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogP0.273Not Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.71 g/LALOGPS
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 RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DarkChem[M+H]+PredictedNot Available151.24331661259
DarkChem[M-H]-PredictedNot Available148.38631661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,1TMS,#12246.9548https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,1TMS,#22210.7275https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,1TMS,#32388.326https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,1TMS,#42238.035https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,2TMS,#12240.375https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,2TMS,#22397.0808https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,2TMS,#32363.8557https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,2TMS,#42370.2217https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,2TMS,#52246.4827https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,2TMS,#62386.5957https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,2TMS,#72276.3901https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,1TBDMS,#12527.079https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,1TBDMS,#22477.7627https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,1TBDMS,#32656.3584https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,1TBDMS,#42522.238https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,2TBDMS,#12743.8882https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,2TBDMS,#22918.2341https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,2TBDMS,#32844.1416https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,2TBDMS,#42851.9526https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,2TBDMS,#52738.7642https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,2TBDMS,#62880.2053https://arxiv.org/abs/1905.12712
4-(2-Amino-3-hydroxyphenyl)-2,4-dioxobutanoic acid,2TBDMS,#72732.417https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0553-7910000000-894d2b28fa25786b8cf42017-09-01View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-00dl-9384000000-d85d64127c1a306053b02017-10-06View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0abi-0690000000-607a25e04b41184c2e112017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-000i-0910000000-f6e7ca1f649c7d85f1c82017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052u-9800000000-9abd1533cae37b5a1e312017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-2290000000-db5113faa78a8f8688172017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fi0-2940000000-5c30994df2e0c448d78f2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-4900000000-5c2c2b7f0e47291f345d2017-09-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-056r-0900000000-98462e5bccca7cad48a32021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-fd75faf4a2b73326af8e2021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4l-4900000000-564c7472238de91e0b052021-09-08View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0930000000-b4c5ebc1b694910581582021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06ri-2900000000-6b672118eb0609fb3d7e2021-09-09View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-053r-9300000000-ee7e4c997d23d017bcb62021-09-09View Spectrum
Biological Properties
Cellular LocationsNot Available
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 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
Food Biomarker OntologyNot Available
VMH ID42A3HP24DB
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:
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