2-ammonio-4-(2-ammoniophenyl)-4-oxo-(2S)-butanoate

ID: ALA498416

Cas Number: 2922-83-0

PubChem CID: 161166

Product Number: S138616, Order Now?

Max Phase: Phase

Molecular Formula: C10H12N2O3

Molecular Weight: 208.22

Molecule Type: Small molecule

Names and Identifiers

Synonyms: L-kynurenine | L-kynurenine|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-Show More⌵

Canonical SMILES:  Nc1ccccc1C(=O)C[C@H](N)C(=O)O

Standard 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

Standard InChI Key:  YGPSJZOEDVAXAB-QMMMGPOBSA-N

Molfile:  

     RDKit          2D

 15 15  0  0  1  0  0  0  0  0999 V2000
    5.0898   -1.1275    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.9477   -0.3025    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2333    0.9350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6609   -1.1275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.5188   -1.1275    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754    0.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0898   -0.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6609   -0.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8043    0.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5188   -0.3025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3754    0.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9464    0.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2333    0.1100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6609    1.3475    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9464    0.9350    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  7  2  0
  2 13  2  0
  3 13  1  0
  4  8  1  0
 10  5  1  1
  6  7  1  0
  6  8  1  0
  6 11  2  0
  7  9  1  0
  8 12  2  0
  9 10  1  0
 10 13  1  0
 11 14  1  0
 12 15  1  0
 14 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA498416

   L-Kynurenine Hydrate

2. Alternative Forms:

   

   ALA498416

   L-Kynurenine sulfate salt

Molecule Features

Natural Product: Yes

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 208.22

Molecular Weight (Monoisotopic): 208.0848

AlogP: 0.25

#Rotatable Bonds: 4

Polar Surface Area: 106.41

Molecular Species: ZWITTERION

HBA: 4

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 5

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.19

CX Basic pKa: 8.96

CX LogP: -1.91

CX LogD: -1.92

Aromatic Rings: 1

Heavy Atoms: 15

QED Weighted: 0.49

Np Likeness Score: 0.67

References

1. Ross FC, Botting NP, Leeson PD.  (1996)  Synthesis of phosphinic acid transition state analogues for the reaction catalysed by kynureninase,  6  (22): [10.1016/S0960-894X(96)00483-0]

2. Lima S, Kumar S, Gawandi V, Momany C, Phillips RS..  (2009)  Crystal structure of the Homo sapiens kynureninase-3-hydroxyhippuric acid inhibitor complex: insights into the molecular basis of kynureninase substrate specificity.,  52  (2): [PMID:19143568] [10.1021/jm8010806]

3. Blount KF, Wang JX, Lim J, Sudarsan N, Breaker RR..  (2007)  Antibacterial lysine analogs that target lysine riboswitches.,  3  (1): [PMID:17143270] [10.1038/nchembio842]

4. PubChem BioAssay data set, 

5. Henrottin J, Zervosen A, Lemaire C, Sapunaric F, Laurent S, Van den Eynde B, Goldman S, Plenevaux A, Luxen A..  (2015)  N (1)-Fluoroalkyltryptophan Analogues: Synthesis and in vitro Study as Potential Substrates for Indoleamine 2,3-Dioxygenase.,  6  (3): [PMID:25815143] [10.1021/ml500385d]

6.  (2014)  D-serine transporter inhibitors as pharmaceutical compositions for the treatment of central nervous system disorders, 

7. Phillips RS, Anderson AD, Gentry HG, Güner OF, Bowen JP..  (2017)  Substrate and inhibitor specificity of kynurenine monooxygenase from Cytophaga hutchinsonii.,  27  (8): [PMID:28302400] [10.1016/j.bmcl.2017.02.080]

8. Unpublished dataset, 

9. Dolciami D, Ballarotto M, Gargaro M, López-Cara LC, Fallarino F, Macchiarulo A..  (2020)  Targeting Aryl hydrocarbon receptor for next-generation immunotherapies: Selective modulators (SAhRMs) versus rapidly metabolized ligands (RMAhRLs).,  185  [PMID:31727470] [10.1016/j.ejmech.2019.111842]

Source

Source(4):

• Scientific Literature
• PubChem BioAssays
• Clinical Candidates
• Patent Bioactivity Data