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

ID: ALA35957

PubChem CID: 44282027

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-/m1/s1

Standard InChI Key:  KBJZPNMDKSNLIZ-MRVPVSSYSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  1  0  0  0  0  0999 V2000
    2.5625    0.6958    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.8667   -1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3542   -0.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8917   -0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5042   -1.2125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0417   -0.9292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7167   -0.1750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1792   -0.4542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0542    1.3583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7417    0.7833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.3292   -1.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1917   -1.7792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667    0.2083    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0167   -1.8792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4042   -0.7375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542   -1.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292   -1.4917    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  2  0
  7  4  1  0
  8  3  1  0
  9  1  1  0
 10  1  2  0
 11  5  2  0
 12  2  2  0
  8 13  1  1
 14  5  1  0
 15  4  2  0
 16 17  2  0
 17 15  1  0
  6 16  1  0
M  CHG  2   1   1   9  -1
M  END

Alternative Forms

1. Parent:

   

   ALA35957

   (R)-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. 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]

Source

Source(1):

• Scientific Literature