Showing metabocard for L-3-Hydroxykynurenine (BMDB0011631)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (3) Show 3 proteinsXML
Record Information
Version1.0
Creation Date2016-10-03 18:22:00 UTC
Update Date2020-05-21 16:28:50 UTC
BMDB IDBMDB0011631
Secondary Accession Numbers
  • BMDB11631
Metabolite Identification
Common NameL-3-Hydroxykynurenine
DescriptionL-3-Hydroxykynurenine, also known as L-3-hydroxykynurenine, 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. L-3-Hydroxykynurenine is possibly soluble (in water) and a very strong basic compound (based on its pKa). L-3-Hydroxykynurenine exists in all living species, ranging from bacteria to humans. L-3-Hydroxykynurenine participates in a number of enzymatic reactions, within cattle. In particular, L-3-Hydroxykynurenine can be biosynthesized from L-kynurenine; which is catalyzed by the enzyme kynurenine 3-monooxygenase. In addition, L-3-Hydroxykynurenine can be converted into 3-hydroxyanthranilic acid and L-alanine through its interaction with the enzyme kynureninase. In cattle, L-3-hydroxykynurenine is involved in the metabolic pathway called the tryptophan metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acidChEBI
3-(3-Hydroxyanthraniloyl)-L-alanineChEBI
(2S)-2-Amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoateGenerator
3-(2-Amino-3-hydroxybenzoyl)-L-alanineHMDB
3-Hydroxy-L-kynurenineHMDB
L-3-HKHMDB
Chemical FormulaC10H12N2O4
Average Molecular Weight224.2133
Monoisotopic Molecular Weight224.079706882
IUPAC Name(2S)-2-amino-4-(2-amino-3-hydroxyphenyl)-4-oxobutanoic acid
Traditional Name3-hydroxy-L-kynurenine
CAS Registry Number606-14-4
SMILES
N[C@@H](CC(=O)C1=CC=CC(O)=C1N)C(O)=O
InChI Identifier
InChI=1S/C10H12N2O4/c11-6(10(15)16)4-8(14)5-2-1-3-7(13)9(5)12/h1-3,6,13H,4,11-12H2,(H,15,16)/t6-/m0/s1
InChI KeyVCKPUUFAIGNJHC-LURJTMIESA-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
  • L-alpha-amino acid
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • O-aminophenol
  • Gamma-keto acid
  • Aminophenol
  • Aniline or substituted anilines
  • Aryl alkyl ketone
  • Benzoyl
  • Phenol
  • 1-hydroxy-2-unsubstituted benzenoid
  • 1-hydroxy-4-unsubstituted benzenoid
  • Keto acid
  • Beta-aminoketone
  • Benzenoid
  • Monocyclic benzene moiety
  • Vinylogous amide
  • Amino acid or derivatives
  • Amino acid
  • Carboxylic acid
  • Carboxylic acid derivative
  • Monocarboxylic acid or derivatives
  • Organic nitrogen compound
  • Primary aliphatic amine
  • Organonitrogen compound
  • Primary amine
  • Hydrocarbon derivative
  • Organic oxide
  • Amine
  • Organopnictogen 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
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-2.1ALOGPS
logP-2.2ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)0.99ChemAxon
pKa (Strongest Basic)8.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area126.64 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity57.03 m³·mol⁻¹ChemAxon
Polarizability21.67 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, Positivesplash10-057u-7910000000-88ad37433d9fe2009b5eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (2 TMS) - 70eV, Positivesplash10-0596-8379000000-0b0a9595aae2502a55acView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-004i-0960000000-c33d63911a63b0e55059View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0209-2900000000-733debea97f59a15a620View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-000l-6900000000-908957a56bc62255065aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00di-1290000000-49db02e2f97330c6041fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00di-9650000000-45bd0384724255104d6cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0ab9-7900000000-e62c0de8b7c63b9e4066View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-056r-0890000000-24d8093dfa7cd7471959View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-070i-1900000000-3159845d0fd09fc5476cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-9700000000-c823da7e7ec85255fba0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ab9-0690000000-e55cff3d90188bbe1b4fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-1910000000-15ef15dcef2ce9fdfef5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a4i-6900000000-2b99b24490fd7fc7a3f9View in MoNA
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0011631
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB028330
KNApSAcK IDC00007443
Chemspider ID11318
KEGG Compound IDC03227
BioCyc ID3-HYDROXY-L-KYNURENINE
BiGG IDNot Available
Wikipedia Link3-Hydroxykynurenine
METLIN IDNot Available
PubChem Compound11811
PDB ID3DJ
ChEBI ID17380
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
Enzyme Details
2. Kynureninase
General function:
Not Available
Specific function:
Catalyzes the cleavage of L-kynurenine (L-Kyn) and L-3-hydroxykynurenine (L-3OHKyn) into anthranilic acid (AA) and 3-hydroxyanthranilic acid (3-OHAA), respectively. Has a preference for the L-3-hydroxy form. Also has cysteine-conjugate-beta-lyase activity.
Gene Name:
KYNU
Uniprot ID:
F1MCH2
Molecular weight:
52186.0
Reactions
L-3-Hydroxykynurenine + Water → 3-Hydroxyanthranilic acid + L-Alaninedetails
Enzyme Details
3. Kynurenine 3-monooxygenase
General function:
Not Available
Specific function:
Not Available
Gene Name:
KMO
Uniprot ID:
E1BN59
Molecular weight:
51032.0
Reactions
L-Kynurenine + NADPH + Oxygen → L-3-Hydroxykynurenine + NADP + Waterdetails