(S)-(+)-2-Amino-4-(3-nitro-phenyl)-4-oxo-butyric acid[(S)-(+)-m-nicotinylbenzoylalanine]

ID: ALA22740

PubChem CID: 10376895

Max Phase: Preclinical

Molecular Formula: C10H10N2O5

Molecular Weight: 238.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N[C@@H](CC(=O)c1cccc([N+](=O)[O-])c1)C(=O)O

Standard InChI:  InChI=1S/C10H10N2O5/c11-8(10(14)15)5-9(13)6-2-1-3-7(4-6)12(16)17/h1-4,8H,5,11H2,(H,14,15)/t8-/m0/s1

Standard InChI Key:  KBJZPNMDKSNLIZ-QMMMGPOBSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  1  0  0  0  0  0999 V2000
    3.8167   -3.9250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -2.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -2.4042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -3.3167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -2.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -2.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -4.2250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3417   -4.2250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9375   -2.1000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8542   -1.5125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8917   -1.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.4167   -3.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -3.0167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8167   -2.1125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3042   -2.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  6  1  0
  3  2  1  0
  4  1  1  0
  5  8  1  0
  6  7  1  0
  7  4  2  0
  8  3  1  0
  9  1  1  0
 10  1  2  0
 11  5  2  0
 12  2  2  0
  8 13  1  6
 14  5  1  0
 15  4  1  0
 16 17  1  0
 17 15  2  0
  6 16  2  0
M  CHG  2   1   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA22740

   (S)-2-Amino-4-(3-nitro-phenyl)-4-oxo-butyric acid

Molecule Features

Natural Product: No

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: 238.20

Molecular Weight (Monoisotopic): 238.0590

AlogP: 0.58

#Rotatable Bonds: 5

Polar Surface Area: 123.53

Molecular Species: ZWITTERION

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 1.05

CX Basic pKa: 8.96

CX LogP: -1.79

CX LogD: -1.80

Aromatic Rings: 1

Heavy Atoms: 17

QED Weighted: 0.44

Np Likeness Score: -0.49

References

1. Drysdale MJ, Hind SL, Jansen M, Reinhard JF..  (2000)  Synthesis and SAR of 4-aryl-2-hydroxy-4-oxobut-2-enoic acids and esters and 2-amino-4-aryl-4-oxobut-2-enoic acids and esters: potent inhibitors of kynurenine-3-hydroxylase as potential neuroprotective agents.,  43  (1): [PMID:10633043] [10.1021/jm990396t]

2. Natalini B, Mattoli L, Pellicciari R, Carpenedo R, Chiarugi A, Moroni F.  (1995)  Synthesis and activity of enantiopure (S) (m-nitrobenzoyl) alanine, potent kynurenine-3-hydroxylase inhibitor,  5  (14): [10.1016/0960-894X(95)00255-R]

3. Liddle J, Beaufils B, Binnie M, Bouillot A, Denis AA, Hann MM, Haslam CP, Holmes DS, Hutchinson JP, Kranz M, McBride A, Mirguet O, Mole DJ, Mowat CG, Pal S, Rowland P, Trottet L, Uings IJ, Walker AL, Webster SP..  (2017)  The discovery of potent and selective kynurenine 3-monooxygenase inhibitors for the treatment of acute pancreatitis.,  27  (9): [PMID:28336141] [10.1016/j.bmcl.2017.02.078]

Source

Source(1):

• Scientific Literature