Showing Compound L-Kynurenine (FDB022181)

Record Information

Version

1.0

Creation date

2011-09-21 00:09:43 UTC

Update date

2024-11-29 22:27:54 UTC

Primary ID

FDB022181

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

L-Kynurenine

Description

Kynurenine 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 Number

2922-83-0

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Synonym	Source
(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoate	Generator
(2S)-2-amino-4-(2-Aminophenyl)-4-oxobutanoate	Generator
(2S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid	ChEBI
(2S)-2-amino-4-(2-Aminophenyl)-4-oxobutanoic acid	ChEBI
(alphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoate	hmdb
(alphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoic acid	hmdb
(S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoate	HMDB
(S)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoate	hmdb
(S)-alpha,2-Diamino-3-hydroxy-gamma-oxo-benzenebutanoic acid	HMDB
(S)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoic acid	hmdb

Showing 1 to 10 of 30 entries

Predicted Properties

Property	Value	Source
Water Solubility	1.67 g/L	ALOGPS
logP	-1.9	ALOGPS
logP	-1.9	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	1.19	ChemAxon
pKa (Strongest Basic)	8.96	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	106.41 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	55.05 m³·mol⁻¹	ChemAxon
Polarizability	20.59 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C10H12N2O3

IUPAC name

(2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid

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 Key

YGPSJZOEDVAXAB-QMMMGPOBSA-N

Isomeric SMILES

N[C@@H](CC(=O)C1=CC=CC=C1N)C(O)=O

Average Molecular Weight

208.2139

Monoisotopic Molecular Weight

208.08479226

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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-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 Framework

Aromatic homomonocyclic compounds

External Descriptors

non-proteinogenic L-alpha-amino acid (CHEBI:16946 )
kynurenine (CHEBI:16946 )

Ontology

Physiological effect

Health effect:

Health condition:

Nervous system disorders:

Hydrocephalus

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Biological location:

Role

Industrial application:

Pharmaceutical industry:

Pharmaceutical

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
GC-MS	L-Kynurenine, non-derivatized, GC-MS Spectrum	splash10-014l-0931000000-29fa7c323b035cb399d3	Spectrum
GC-MS	L-Kynurenine, non-derivatized, GC-MS Spectrum	splash10-014l-0931000000-29fa7c323b035cb399d3	Spectrum
GC-MS	L-Kynurenine, non-derivatized, GC-MS Spectrum	splash10-014l-0931000000-a43ae0acafac266101c4	Spectrum
GC-MS	L-Kynurenine, non-derivatized, GC-MS Spectrum	splash10-0006-1910000000-fdc25d09b4da4b1d7657	Spectrum
Predicted GC-MS	L-Kynurenine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00dl-9500000000-d7bf6a26c74e0dcabf40	Spectrum
Predicted GC-MS	L-Kynurenine, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-4920000000-cb575b96b16b3ef9130f	Spectrum
Predicted GC-MS	L-Kynurenine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Kynurenine, TMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Kynurenine, TMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Kynurenine, TBDMS_1_1, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Kynurenine, TBDMS_1_2, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	L-Kynurenine, TBDMS_1_3, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)	splash10-0006-2910000000-366ce08b5736d68dfad0	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)	splash10-01bd-5900000000-c18e10be7e029474cf03	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)	splash10-00kf-9300000000-0f8238d38819f6f30d12	2012-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 10V, Positive	splash10-0a4i-0790000000-3fa45266412288bf1c62	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 20V, Positive	splash10-0007-3900000000-a66f45aff81960af7575	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 30V, Positive	splash10-00xv-5900000000-15442ec5aaef005401ae	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 40V, Positive	splash10-00r7-7900000000-0833fe9d2739d329f197	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QQ (API3000, Applied Biosystems) 50V, Positive	splash10-0006-9400000000-d5d45364462a730de436	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0006-0900000000-13929f0bde71b6326d3f	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0f6w-2900000000-b2d4f361ffee9fd93bb7	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-004j-0900000000-96930a886f7bbcc44df3	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-000i-0900000000-2441a358973abdb063da	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT (LC/MSD Trap XCT, Agilent Technologies) , Positive	splash10-0udi-0900000000-dc4fee4751d629575157	2012-08-31	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0006-0900000000-4ec06cc06a3eab2625d6	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0006-0900000000-319acefac99779fa7552	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0059-0890000000-4280b92b875a6f754a91	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-0059-0890000000-664e2c8904363418682e	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00dj-0139000000-aa6188977ba2f460f5bc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-00dj-0139000000-ee71a364df13bd095feb	2017-09-14	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-06r7-0920000000-f2e6efdd3988d3010e33	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-022a-3900000000-e1c06099462847ad5b97	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00di-9700000000-a9df2d5ca325f97f69f1	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-2490000000-9604ae0cc9d437acd878	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00dl-9520000000-8f0ea7d174290496860d	2016-09-12	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-006x-9400000000-9721076505654380d2de	2016-09-12	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, D₂O, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, H₂O, experimental)	Spectrum

External Links

ChemSpider ID

ChEMBL ID

KEGG Compound ID

Pubchem Compound ID

Pubchem Substance ID

Not Available

ChEBI ID

Not Available

Phenol-Explorer ID

Not Available

DrugBank ID

DB02070

HMDB ID

HMDB00684

CRC / DFC (Dictionary of Food Compounds) ID

Not Available

EAFUS ID

Not Available

Dr. Duke ID

Not Available

BIGG ID

1445574

KNApSAcK ID

Not Available

HET ID

KYN

Food Biomarker Ontology

Not Available

VMH ID

Not Available

Flavornet ID

Not Available

GoodScent ID

Not Available

SuperScent ID

Not Available

Wikipedia ID

Kynurenine

Phenol-Explorer Metabolite ID

Not Available

Duplicate IDS

Not Available

Old DFC IDS

Not Available

Associated Foods

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Food	Content Range	Average	Reference

Processing...

Biological Effects and Interactions

Health Effects / Bioactivities

Not Available

Enzymes

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Name	Gene Name	UniProt ID
Aspartate aminotransferase, mitochondrial	GOT2	P00505
Kynurenine--oxoglutarate transaminase 1	CCBL1	Q16773
Kynurenine--oxoglutarate transaminase 3	CCBL2	Q6YP21
Kynurenine/alpha-aminoadipate aminotransferase, mitochondrial	AADAT	Q8N5Z0

Showing 1 to 4 of 4 entries

Pathways

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Name	SMPDB Link	KEGG Link
Metabolism and Physiological Effects of 2-Aminobenzoic acid	SMP0126869	Not Available
Metabolism and Physiological Effects of Kynurenic Acid	SMP0123300	Not Available
Metabolism and Physiological Effects of Kynurenine	SMP0125524	Not Available
Metabolism and Physiological Effects of Quinolinic Acid	SMP0123249	Not Available
Tryptophan Metabolism	SMP00063	map00380