L-kynurenine

Details

• Internal ID: 91c7c504-256c-4c22-933e-7744f994c567
• Taxonomy: Organic oxygen compounds > Organooxygen compounds > Carbonyl compounds > Phenylketones > Alkyl-phenylketones
• IUPAC Name: (2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
• SMILES (Canonical): C1=CC=C(C(=C1)C(=O)CC(C(=O)O)N)N
• SMILES (Isomeric): C1=CC=C(C(=C1)C(=O)C[C@@H](C(=O)O)N)N
• InChI: 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
• Popularity: 866 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₂N₂O₃
• Molecular Weight: 208.21 g/mol
• Exact Mass: 208.08479225 g/mol
• Topological Polar Surface Area (TPSA): 106.00 Ų
• XlogP: -2.20
• Atomic LogP (AlogP): 0.25
• H-Bond Acceptor: 4
• H-Bond Donor: 3
• Rotatable Bonds: 4

Synonyms

• 2922-83-0
• (S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid
• Kynurenine, L-
• 3-Anthraniloyl-L-alanine
• (2S)-2-amino-4-(2-aminophenyl)-4-oxobutanoic acid
• CHEBI:16946
• Kynurenin
• 02JW4J5R44
• Benzenebutanoic acid, .alpha.,2-diamino-.gamma.-oxo-, (S)-
• Benzenebutanoic acid, alpha,2-diamino-gamma-oxo-, (alphaS)-
• Quinurenine
• CCRIS 4425
• UNII-02JW4J5R44
• (2S)-4-(2-aminophenyl)-2-azaniumyl-4-oxobutanoate
• (S)-Kynurenine
• Kynurenine (L)
• KYN
• 3-anthraniloyl-alanine
• DL-Kynureninefree base
• 2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid #
• L-Kynurenine, free base
• bmse000172
• KYNURENINE, (+)-
• SCHEMBL20875
• (S)-2-Amino-4-(2-aminophenyl)-4-oxobutanoicacid
• 3-(2-aminobenzoyl)-L-alanine
• CHEMBL498416
• DTXSID101031182
• KUC106759N
• L-Kynurenine, >=98% (HPLC)
• BCP20697
• L-3-(O-AMINOBENZOYL)ALANINE
• BDBM50506041
• MFCD00069912
• s5839
• AKOS016843487
• DB02070
• NCGC00163345-01
• CS-13161
• KSC-11-228-1
• alpha,2-diamino-gamma-oxo-Benzenebutanoate
• HY-104026
• TRYPTOPHAN IMPURITY C [EP IMPURITY]
• CS-0022016
• K0016
• alpha,2-diamino-gamma-oxo-Benzenebutanoic acid
• C00328
• EN300-244590
• K-9020
• A819827
• L-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid
• Q415768
• N-ACETYLTRYPTOPHAN IMPURITY C [EP IMPURITY]
• (S)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoate
• (alphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoate
• (S)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoic acid
• (2S)-2-amino-4-(2-aminophenyl)-4-oxo-butanoic acid;L-Kynurenine
• (alphaS)-alpha,2-diamino-3-hydroxy-gamma-oxo-Benzenebutanoic acid
• BENZENEBUTANOIC ACID, .ALPHA.,2-DIAMINO-.GAMMA.-OXO-, (.ALPHA.S)-
• beta-Anthraniloyl-L-alanine, L-2-Amino-4-(2-aminophenyl)-4-oxobutanoic acid
• L-2-AMINO-3-(2-AMINOBENZOYL)PROPIONIC ACID L-2-AMINO-4-[2-AMINOPHENYL]-4-OXOBUTANOIC ACID L-KYNURENINE L-kynurenine free base

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.8620	86.20%
Caco-2	-	0.8553	85.53%
Blood Brain Barrier	+	0.5750	57.50%
Human oral bioavailability	+	0.7429	74.29%
Subcellular localzation	Mitochondria	0.7073	70.73%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9552	95.52%
OATP1B3 inhibitior	+	0.9502	95.02%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.9250	92.50%
BSEP inhibitior	-	0.9058	90.58%
P-glycoprotein inhibitior	-	0.9893	98.93%
P-glycoprotein substrate	-	0.9535	95.35%
CYP3A4 substrate	-	0.7644	76.44%
CYP2C9 substrate	-	0.5905	59.05%
CYP2D6 substrate	-	0.8184	81.84%
CYP3A4 inhibition	-	0.9600	96.00%
CYP2C9 inhibition	-	0.9500	95.00%
CYP2C19 inhibition	-	0.9540	95.40%
CYP2D6 inhibition	-	0.9540	95.40%
CYP1A2 inhibition	-	0.9409	94.09%
CYP2C8 inhibition	-	0.9176	91.76%
CYP inhibitory promiscuity	-	0.9772	97.72%
UGT catelyzed	-	0.0000	0.00%
Carcinogenicity (binary)	-	0.7711	77.11%
Carcinogenicity (trinary)	Non-required	0.7805	78.05%
Eye corrosion	-	0.9932	99.32%
Eye irritation	-	0.8276	82.76%
Skin irritation	-	0.8394	83.94%
Skin corrosion	-	0.9506	95.06%
Ames mutagenesis	-	0.9000	90.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.8733	87.33%
Micronuclear	+	0.8000	80.00%
Hepatotoxicity	-	0.5000	50.00%
skin sensitisation	-	0.8229	82.29%
Respiratory toxicity	-	0.6444	64.44%
Reproductive toxicity	+	0.6444	64.44%
Mitochondrial toxicity	+	0.7750	77.50%
Nephrotoxicity	+	0.5000	50.00%
Acute Oral Toxicity (c)	III	0.6429	64.29%
Estrogen receptor binding	-	0.9025	90.25%
Androgen receptor binding	-	0.6059	60.59%
Thyroid receptor binding	-	0.8467	84.67%
Glucocorticoid receptor binding	+	0.5459	54.59%
Aromatase binding	-	0.7952	79.52%
PPAR gamma	+	0.5608	56.08%
Honey bee toxicity	-	0.9227	92.27%
Biodegradation	-	0.6000	60.00%
Crustacea aquatic toxicity	-	0.7900	79.00%
Fish aquatic toxicity	-	0.3843	38.43%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	96.51%	90.17%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	95.01%	96.09%
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	91.62%	91.11%
CHEMBL3091268	Q92753	Nuclear receptor ROR-beta	90.18%	95.50%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.67%	95.56%
CHEMBL2581	P07339	Cathepsin D	86.68%	98.95%
CHEMBL1255126	O15151	Protein Mdm4	83.34%	90.20%
CHEMBL1293249	Q13887	Kruppel-like factor 5	82.39%	86.33%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.28%	94.62%
CHEMBL4040	P28482	MAP kinase ERK2	80.21%	83.82%

Plants that contains it

There are no matching plants.

Cross-Links

• PubChem: 161166
• LOTUS: LTS0100823
• wikiData: Q415768