Showing metabocard for L-Kynurenine (BMDB0000684)

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Record Information
Version1.0
Creation Date2016-09-30 22:34:52 UTC
Update Date2020-06-04 20:08:18 UTC
BMDB IDBMDB0000684
Secondary Accession Numbers
  • BMDB00684
Metabolite Identification
Common NameL-Kynurenine
DescriptionL-Kynurenine, also known as quinurenine, 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-Kynurenine exists as a solid, possibly soluble (in water), and a very strong basic compound (based on its pKa) molecule. L-Kynurenine exists in all eukaryotes, ranging from yeast to humans. L-Kynurenine participates in a number of enzymatic reactions, within cattle. In particular, L-Kynurenine and formic acid can be biosynthesized from n'-formylkynurenine; which is mediated by the enzyme kynurenine formamidase. In addition, L-Kynurenine can be converted into 2-aminobenzoic acid and L-alanine through the action of the enzyme kynureninase. In cattle, L-kynurenine is involved in the metabolic pathway called the tryptophan metabolism pathway.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acidChEBI
3-Anthraniloyl-L-alanineChEBI
KYNURENINEChEBI
(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoateGenerator
(S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoateHMDB
(S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoic acidHMDB
3-Anthraniloyl-alanineHMDB
3-AnthraniloylalanineHMDB
alpha,2-Diamino-gamma-oxo-benzenebutanoateHMDB
alpha,2-Diamino-gamma-oxo-benzenebutanoic acidHMDB
DL-KynurenineHMDB
KynureninHMDB
QuinurenineHMDB
L-KynurenineHMDB
3-(2-aminobenzoyl)-L-alanineHMDB
KYNAHMDB
Chemical FormulaC10H12N2O3
Average Molecular Weight208.2139
Monoisotopic Molecular Weight208.08479226
IUPAC Name(2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
Traditional NameL-kynurenine
CAS Registry Number2922-83-0
SMILES
N[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O
InChI Identifier
InChI=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
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
  • 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
StatusDetected and Quantified
Origin
  • Endogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cytoplasm
  • Mitochondria
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point191 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-EI-TOF (Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies) (Non-derivatized)splash10-014l-0931000000-29fa7c323b035cb399d3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014l-0931000000-29fa7c323b035cb399d3View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-014l-0931000000-a43ae0acafac266101c4View in MoNA
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-0006-1910000000-fdc25d09b4da4b1d7657View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00dl-9500000000-d7bf6a26c74e0dcabf40View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-4920000000-cb575b96b16b3ef9130fView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_2) - 70eV, PositiveNot AvailableView in JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_3) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0006-2910000000-366ce08b5736d68dfad0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-01bd-5900000000-c18e10be7e029474cf03View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-00kf-9300000000-0f8238d38819f6f30d12View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positivesplash10-0a4i-0790000000-3fa45266412288bf1c62View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positivesplash10-0007-3900000000-a66f45aff81960af7575View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positivesplash10-00xv-5900000000-15442ec5aaef005401aeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positivesplash10-00r7-7900000000-0833fe9d2739d329f197View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positivesplash10-0006-9400000000-d5d45364462a730de436View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0006-0900000000-13929f0bde71b6326d3fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0f6w-2900000000-b2d4f361ffee9fd93bb7View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-004j-0900000000-96930a886f7bbcc44df3View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-000i-0900000000-2441a358973abdb063daView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positivesplash10-0udi-0900000000-dc4fee4751d629575157View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0900000000-4ec06cc06a3eab2625d6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0006-0900000000-319acefac99779fa7552View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0890000000-4280b92b875a6f754a91View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-0059-0890000000-664e2c8904363418682eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00dj-0139000000-aa6188977ba2f460f5bcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-00dj-0139000000-ee71a364df13bd095febView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-06r7-0920000000-f2e6efdd3988d3010e33View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-022a-3900000000-e1c06099462847ad5b97View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00di-9700000000-a9df2d5ca325f97f69f1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-2490000000-9604ae0cc9d437acd878View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00dl-9520000000-8f0ea7d174290496860dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-006x-9400000000-9721076505654380d2deView in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, D2O, experimental)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 100 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, 200 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, 300 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, 400 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, 500 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, 600 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, 700 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, 800 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR13C NMR Spectrum (1D, 900 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, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, H2O, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cytoplasm
  • Mitochondria
Biospecimen Locations
  • Blood
  • Brain
  • Epidermis
  • Fibroblasts
  • Intestine
  • Liver
  • Longissimus Thoracis Muscle
  • Milk
  • Neuron
  • Placenta
  • Ruminal Fluid
  • Semimembranosus Muscle
  • Spleen
  • Testis
Pathways
Normal Concentrations
Abnormal Concentrations
Not Available
HMDB IDHMDB0000684
DrugBank IDDB02070
Phenol Explorer Compound IDNot Available
FooDB IDFDB022181
KNApSAcK IDC00007604
Chemspider ID141580
KEGG Compound IDC00328
BioCyc IDCPD-14736
BiGG ID1445574
Wikipedia LinkKynurenine
METLIN ID72
PubChem Compound161166
PDB IDNot Available
ChEBI ID16946
References
Synthesis ReferenceHayaishi, Osamu. L-Kynurenine sulfate monohydrate. Biochemical Preparations (1953), 3 108-11.
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Melzer N, Wittenburg D, Hartwig S, Jakubowski S, Kesting U, Willmitzer L, Lisec J, Reinsch N, Repsilber D: Investigating associations between milk metabolite profiles and milk traits of Holstein cows. J Dairy Sci. 2013 Mar;96(3):1521-34. doi: 10.3168/jds.2012-5743. [PubMed:23438684 ]
  2. Mung D, Li L: Development of Chemical Isotope Labeling LC-MS for Milk Metabolomics: Comprehensive and Quantitative Profiling of the Amine/Phenol Submetabolome. Anal Chem. 2017 Apr 18;89(8):4435-4443. doi: 10.1021/acs.analchem.6b03737. Epub 2017 Mar 28. [PubMed:28306241 ]
  3. Mung D, Li L: Applying quantitative metabolomics based on chemical isotope labeling LC-MS for detecting potential milk adulterant in human milk. Anal Chim Acta. 2018 Feb 25;1001:78-85. doi: 10.1016/j.aca.2017.11.019. Epub 2017 Nov 14. [PubMed:29291809 ]

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-Kynurenine + Oxoglutaric acid → 4-(2-Aminophenyl)-2,4-dioxobutanoic acid + L-Glutamic aciddetails
Enzyme Details
2. Kynurenine--oxoglutarate transaminase 3
General function:
Amino acid transport and metabolism
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:
KYAT3
Uniprot ID:
Q0P5G4
Molecular weight:
51472.0
Enzyme Details
3. 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-Kynurenine + Water → 2-Aminobenzoic acid + L-Alaninedetails
Enzyme Details
4. Kynurenine formamidase
General function:
Not Available
Specific function:
Catalyzes the hydrolysis of N-formyl-L-kynurenine to L-kynurenine, the second step in the kynurenine pathway of tryptophan degradation. Kynurenine may be further oxidized to nicotinic acid, NAD(H) and NADP(H). Required for elimination of toxic metabolites.
Gene Name:
AFMID
Uniprot ID:
E1BLL5
Molecular weight:
35460.0
Reactions
N'-Formylkynurenine + Water → L-Kynurenine + Formic aciddetails
Enzyme Details
5. 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