2-((2-Amino-2-oxoethyl)amino)-N-(2-methoxyphenyl)-6-((4-nitrophenyl)thio)benzamide

ID: ALA4100082

PubChem CID: 71811853

Max Phase: Preclinical

Molecular Formula: C22H20N4O5S

Molecular Weight: 452.49

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccccc1NC(=O)c1c(NCC(N)=O)cccc1Sc1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C22H20N4O5S/c1-31-18-7-3-2-5-16(18)25-22(28)21-17(24-13-20(23)27)6-4-8-19(21)32-15-11-9-14(10-12-15)26(29)30/h2-12,24H,13H2,1H3,(H2,23,27)(H,25,28)

Standard InChI Key:  NLAZZXQUCCPXJQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 34  0  0  0  0  0  0  0  0999 V2000
    9.6701   -8.0564    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.6732   -6.4065    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9581   -6.8212    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9585   -7.6383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2517   -8.0447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5445   -7.6381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5442   -6.8209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2510   -6.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3803   -6.8172    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6728   -5.5852    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6619   -8.8827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3731   -9.2934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3735  -10.1146    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6626  -10.5211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9595  -10.1144    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9592   -9.2932    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6629  -11.3382    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.3742  -11.7489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9561  -11.7487    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.3796   -5.1788    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3793   -4.3576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0820   -3.9470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7932   -4.3578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7936   -5.1790    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0827   -5.5854    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6639   -3.9345    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9454   -4.3390    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2510   -5.5932    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5433   -5.1846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5433   -4.3674    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8356   -3.9588    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.2578   -3.9549    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  3  8  2  0
  2  9  2  0
  2 10  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 11 16  2  0
 17 18  2  0
 17 19  1  0
 14 17  1  0
  1 11  1  0
  4  1  1  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 20 25  2  0
 26 27  1  0
 21 26  1  0
 10 20  1  0
  8 28  1  0
 28 29  1  0
 29 30  1  0
 30 31  1  0
 30 32  2  0
M  CHG  2  17   1  19  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4100082

   2-[(2-amino-2-oxo-ethyl)amino]-N-(2-methoxyphenyl)-6-(4-nitrophenyl)sulfanyl-benzamide

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: 452.49

Molecular Weight (Monoisotopic): 452.1154

AlogP: 3.90

#Rotatable Bonds: 9

Polar Surface Area: 136.59

Molecular Species: NEUTRAL

HBA: 7

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 13.39

CX Basic pKa: ┄

CX LogP: 3.83

CX LogD: 3.83

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.33

Np Likeness Score: -1.57

References

1. Zhou M, Luo RH, Hou XY, Wang RR, Yan GY, Chen H, Zhang RH, Shi JY, Zheng YT, Li R, Wei YQ..  (2017)  Synthesis, biological evaluation and molecular docking study of N-(2-methoxyphenyl)-6-((4-nitrophenyl)sulfonyl)benzamide derivatives as potent HIV-1 Vif antagonists.,  129  [PMID:28235704] [10.1016/j.ejmech.2017.01.010]

Source

Source(1):

• Scientific Literature