Record Information
Version1.0
Creation date2011-09-21 00:09:43 UTC
Update date2019-11-26 03:21:01 UTC
Primary IDFDB022181
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameL-Kynurenine
DescriptionKynurenine is a metabolite of the amino acid tryptophan used in the production of niacin. L-kynurenine is a central compound of the pathway of tryptophan metabolism pathway since it can change to the neuroprotective agent kynurenic acid or to the neurotoxic agent quinolinic acid. The break-up of these endogenous compounds' balance can be observable in many disorders. It can occur in neurodegenerative disorders, such as Parkinson's disease, Huntington's and Alzheimer's disease, in stroke, in epilepsy, in multiple sclerosis, in amyotrophic lateral sclerosis, and in mental failures, such as schizophrenia and depression. [HMDB]
CAS Number2922-83-0
Structure
Thumb
Synonyms
SynonymSource
(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acidChEBI
3-Anthraniloyl-L-alanineChEBI
KYNURENINEChEBI
(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoateGenerator
(AlphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-benzenebutanoateHMDB
(AlphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-benzenebutanoic acidHMDB
(S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoateHMDB
(S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoic acidHMDB
3-(3-Hydroxyanthraniloyl)-L-alanineHMDB
3-Anthraniloyl-alanineHMDB
3-AnthraniloylalanineHMDB
3-Hydroxy-L-kynurenineHMDB
alpha,2-Diamino-gamma-oxo-benzenebutanoateHMDB
alpha,2-Diamino-gamma-oxo-benzenebutanoic acidHMDB
DL-KynurenineHMDB
DL-Kynureninefree baseHMDB
KynureninHMDB
QuinurenineHMDB
(2S)-2-amino-4-(2-Aminophenyl)-4-oxobutanoateGenerator
(2S)-2-amino-4-(2-Aminophenyl)-4-oxobutanoic acidChEBI
(alphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoatehmdb
(alphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoic acidhmdb
(S)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoatehmdb
(S)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoic acidhmdb
3-anthraniloyl-Alaninehmdb
3-anthraniloyl-L-alaninehmdb
alpha,2-diamino-gamma-oxo-Benzenebutanoatehmdb
alpha,2-diamino-gamma-oxo-Benzenebutanoic acidhmdb
dl-Kynureninehmdb
Predicted Properties
PropertyValueSource
Water Solubility1.67 g/LALOGPS
logP-1.9ALOGPS
logP-1.9ChemAxon
logS-2.1ALOGPS
pKa (Strongest Acidic)1.19ChemAxon
pKa (Strongest Basic)8.96ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area106.41 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity55.05 m³·mol⁻¹ChemAxon
Polarizability20.59 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC10H12N2O3
IUPAC name(2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
InChI IdentifierInChI=1S/C10H12N2O3/c11-7-4-2-1-3-6(7)9(13)5-8(12)10(14)15/h1-4,8H,5,11-12H2,(H,14,15)/t8-/m0/s1
InChI KeyYGPSJZOEDVAXAB-QMMMGPOBSA-N
Isomeric SMILESN[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O
Average Molecular Weight208.2139
Monoisotopic Molecular Weight208.08479226
Classification
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
  • Alpha-amino acid
  • Alpha-amino acid or derivatives
  • L-alpha-amino acid
  • Benzoyl
  • Gamma-keto acid
  • Aniline or substituted anilines
  • Aryl alkyl ketone
  • Monocyclic benzene moiety
  • Beta-aminoketone
  • Keto acid
  • Benzenoid
  • Vinylogous amide
  • Amino acid
  • Amino acid or derivatives
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Primary aliphatic amine
  • Amine
  • Hydrocarbon derivative
  • Organopnictogen compound
  • Organic oxide
  • Organic nitrogen compound
  • Organonitrogen compound
  • Primary amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Source:

Biological location:

Role

Industrial application:

Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateSolid
Physical DescriptionNot Available
Mass CompositionNot Available
Melting PointNot Available
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV DataNot Available
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
GC-MSL-Kynurenine, non-derivatized, GC-MS Spectrumsplash10-014l-0931000000-29fa7c323b035cb399d3Spectrum
GC-MSL-Kynurenine, non-derivatized, GC-MS Spectrumsplash10-014l-0931000000-29fa7c323b035cb399d3Spectrum
GC-MSL-Kynurenine, non-derivatized, GC-MS Spectrumsplash10-014l-0931000000-a43ae0acafac266101c4Spectrum
GC-MSL-Kynurenine, non-derivatized, GC-MS Spectrumsplash10-0006-1910000000-fdc25d09b4da4b1d7657Spectrum
Predicted GC-MSL-Kynurenine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00dl-9500000000-d7bf6a26c74e0dcabf40Spectrum
Predicted GC-MSL-Kynurenine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-4920000000-cb575b96b16b3ef9130fSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-2910000000-366ce08b5736d68dfad0Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01bd-5900000000-c18e10be7e029474cf03Spectrum
MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kf-9300000000-0f8238d38819f6f30d12Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4i-0790000000-3fa45266412288bf1c62Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0007-3900000000-a66f45aff81960af7575Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00xv-5900000000-15442ec5aaef005401aeSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00r7-7900000000-0833fe9d2739d329f197Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9400000000-d5d45364462a730de436Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0006-0900000000-13929f0bde71b6326d3fSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0f6w-2900000000-b2d4f361ffee9fd93bb7Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-004j-0900000000-96930a886f7bbcc44df3Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-2441a358973abdb063daSpectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0udi-0900000000-dc4fee4751d629575157Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0900000000-4ec06cc06a3eab2625d6Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0900000000-319acefac99779fa7552Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0890000000-4280b92b875a6f754a91Spectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0890000000-664e2c8904363418682eSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00dj-0139000000-aa6188977ba2f460f5bcSpectrum
MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00dj-0139000000-ee71a364df13bd095febSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06r7-0920000000-f2e6efdd3988d3010e33Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022a-3900000000-e1c06099462847ad5b97Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9700000000-a9df2d5ca325f97f69f1Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2490000000-9604ae0cc9d437acd878Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-9520000000-8f0ea7d174290496860dSpectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9400000000-9721076505654380d2deSpectrum
NMR
TypeDescriptionView
1D NMR1H NMR SpectrumSpectrum
1D NMR1H NMR SpectrumSpectrum
1D NMR13C NMR SpectrumSpectrum
2D NMR[1H,13C] 2D NMR SpectrumSpectrum
ChemSpider ID141580
ChEMBL IDCHEMBL498416
KEGG Compound IDC00328
Pubchem Compound ID161166
Pubchem Substance IDNot Available
ChEBI IDNot Available
Phenol-Explorer IDNot Available
DrugBank IDDB02070
HMDB IDHMDB00684
CRC / DFC (Dictionary of Food Compounds) IDNot Available
EAFUS IDNot Available
Dr. Duke IDNot Available
BIGG ID1445574
KNApSAcK IDNot Available
HET IDKYN
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDKynurenine
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / BioactivitiesNot Available
Enzymes
NameGene NameUniProt ID
Aspartate aminotransferase, mitochondrialGOT2P00505
Kynurenine--oxoglutarate transaminase 3CCBL2Q6YP21
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrialAADATQ8N5Z0
Kynurenine--oxoglutarate transaminase 1CCBL1Q16773
Pathways
NameSMPDB LinkKEGG Link
Tryptophan MetabolismSMP00063 map00380
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSshow
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference