2-amino-N-(2-hydroxyphenyl)-6-((4-nitrophenyl)thio)benzamide

ID: ALA4440538

PubChem CID: 155514663

Max Phase: Preclinical

Molecular Formula: C19H15N3O4S

Molecular Weight: 381.41

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  Nc1cccc(Sc2ccc([N+](=O)[O-])cc2)c1C(=O)Nc1ccccc1O

Standard InChI:  InChI=1S/C19H15N3O4S/c20-14-4-3-7-17(27-13-10-8-12(9-11-13)22(25)26)18(14)19(24)21-15-5-1-2-6-16(15)23/h1-11,23H,20H2,(H,21,24)

Standard InChI Key:  RTGQQHAMWFDGOV-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   39.1866   -3.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.1855   -4.2286    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8935   -4.6376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6032   -4.2281    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6003   -3.4055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   39.8917   -3.0002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3065   -2.9942    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0158   -3.4001    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   41.3034   -2.1770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   42.7219   -2.9889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4296   -3.3982    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1353   -2.9876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   44.1326   -2.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   43.4184   -1.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.7157   -2.1767    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3115   -4.6356    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   41.3128   -5.4528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6044   -5.8609    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   40.6054   -6.6774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3143   -7.0857    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0237   -6.6716    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   42.0192   -5.8565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   41.3178   -7.9077    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   42.0266   -8.3143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   40.6112   -8.3184    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   39.8893   -2.1830    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   43.4306   -4.2154    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  5  7  1  0
  7  8  1  0
  7  9  2  0
  8 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 10  1  0
  4 16  1  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 17  1  0
 23 24  2  0
 23 25  1  0
 20 23  1  0
  6 26  1  0
 11 27  1  0
M  CHG  2  23   1  25  -1
M  END

Alternative Forms

1. Parent:

   

   ALA4440538

   ---

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: 381.41

Molecular Weight (Monoisotopic): 381.0783

AlogP: 4.29

#Rotatable Bonds: 5

Polar Surface Area: 118.49

Molecular Species: NEUTRAL

HBA: 6

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.76

CX Basic pKa: 1.78

CX LogP: 4.71

CX LogD: 4.69

Aromatic Rings: 3

Heavy Atoms: 27

QED Weighted: 0.26

Np Likeness Score: -1.36

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