2-(2-amino-6-((4-nitrophenyl)thio)benzamido)phenyl methanesulfonate

ID: ALA4443526

PubChem CID: 71811764

Max Phase: Preclinical

Molecular Formula: C20H17N3O6S2

Molecular Weight: 459.51

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  CS(=O)(=O)Oc1ccccc1NC(=O)c1c(N)cccc1Sc1ccc([N+](=O)[O-])cc1

Standard InChI:  InChI=1S/C20H17N3O6S2/c1-31(27,28)29-17-7-3-2-6-16(17)22-20(24)19-15(21)5-4-8-18(19)30-14-11-9-13(10-12-14)23(25)26/h2-12H,21H2,1H3,(H,22,24)

Standard InChI Key:  BHNJPVLTHBKUTD-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 31 33  0  0  0  0  0  0  0  0999 V2000
   26.6536   -3.7351    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0758   -4.3171    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.8687   -4.5265    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.1259   -3.1036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1247   -3.9232    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8328   -4.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5424   -3.9227    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5396   -3.1000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8310   -2.6948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2458   -2.6888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9550   -3.0947    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.2427   -1.8716    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.6612   -2.6834    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3688   -3.0928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0745   -2.6822    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.0719   -1.8641    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.3577   -1.4584    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.6549   -1.8713    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2508   -4.3302    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   23.2521   -5.1474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5437   -5.5555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5446   -6.3719    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2535   -6.7803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9629   -6.3662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9585   -5.5511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2570   -7.6023    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   23.9659   -8.0088    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   22.5505   -8.0129    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8285   -1.8776    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.3699   -3.9100    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   26.0791   -5.1348    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9  4  1  0
  8 10  1  0
 10 11  1  0
 10 12  2  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 13  1  0
  7 19  1  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 20  1  0
 26 27  2  0
 26 28  1  0
 23 26  1  0
  9 29  1  0
 14 30  1  0
 30  2  1  0
  2 31  1  0
M  CHG  2  26   1  28  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4443526

   [2-[[2-Amino-6-(4-nitrophenyl)sulfanyl-benzoyl]amino]phenyl] methanesulfonate

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Unknown

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 459.51

Molecular Weight (Monoisotopic): 459.0559

AlogP: 3.92

#Rotatable Bonds: 7

Polar Surface Area: 141.63

Molecular Species: NEUTRAL

HBA: 8

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.72

CX LogP: 4.77

CX LogD: 4.77

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.23

Np Likeness Score: -1.49

References

1. Zhang RH, Wang S, Luo RH, Zhou M, Zhang H, Xu GB, Zhao YL, Li YJ, Wang YL, Yan G, Liao SG, Zheng YT, Li R..  (2019)  Design, synthesis, and biological evaluation of 2-amino-N-(2-methoxyphenyl)-6-((4-nitrophenyl)sulfonyl)benzamide derivatives as potent HIV-1 Vif inhibitors.,  29  (24): [PMID:31685340] [10.1016/j.bmcl.2019.126638]

Source

Source(1):

• Scientific Literature