(para-nitrobenzoyl)alanine

ID: ALA157866

Cas Number: 153212-72-7

PubChem CID: 10331747

Max Phase: Preclinical

Molecular Formula: C10H10N2O5

Molecular Weight: 238.20

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  NC(CC(=O)c1ccc([N+](=O)[O-])cc1)C(=O)O

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

Standard InChI Key:  WSJGJJOHRFJSOD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 17 17  0  0  0  0  0  0  0  0999 V2000
    4.1833   -5.9875    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.7750   -5.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4500   -4.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2583   -4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2958   -4.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7000   -5.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6625   -5.6792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1833   -6.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7375   -5.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8208   -5.0667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.0250   -4.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.0208   -3.7667    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.2500   -4.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7000   -5.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2208   -5.9875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2208   -4.7792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7375   -5.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  4  1  0
  3  5  1  0
  4  9  1  0
  5  2  1  0
  6  1  1  0
  7  1  1  0
  8  1  2  0
  9 17  1  0
 10  5  1  0
 11  3  1  0
 12  3  2  0
 13  4  2  0
 14  6  2  0
 15  6  1  0
 16 14  1  0
 17 15  2  0
 16  9  2  0
M  CHG  2   1   1   7  -1
M  END

Alternative Forms

1. Parent:

   

   ALA157866

   DL-2-Amino-4-(4-nitrophenyl)-4-oxobutanoic 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: -0.31

References

1. Pellicciari R, Natalini B, Costantino G, Mahmoud MR, Mattoli L, Sadeghpour BM, Moroni F, Chiarugi A, Carpenedo R..  (1994)  Modulation of the kynurenine pathway in search for new neuroprotective agents. Synthesis and preliminary evaluation of (m-nitrobenzoyl)alanine, a potent inhibitor of kynurenine-3-hydroxylase.,  37  (5): [PMID:8126705] [10.1021/jm00031a015]

Source

Source(1):

• Scientific Literature