4-((3-amino-2-((2-methoxyphenyl)carbamoyl)phenyl)thio)benzoic acid

ID: ALA4582323

PubChem CID: 71811804

Max Phase: Preclinical

Molecular Formula: C21H18N2O4S

Molecular Weight: 394.45

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  COc1ccccc1NC(=O)c1c(N)cccc1Sc1ccc(C(=O)O)cc1

Standard InChI:  InChI=1S/C21H18N2O4S/c1-27-17-7-3-2-6-16(17)23-20(24)19-15(22)5-4-8-18(19)28-14-11-9-13(10-12-14)21(25)26/h2-12H,22H2,1H3,(H,23,24)(H,25,26)

Standard InChI Key:  HHNXXHUHODEFII-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

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   11.3402  -24.0906    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.3391  -24.9101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0471  -25.3191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7568  -24.9097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7539  -24.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0453  -23.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4601  -23.6757    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1693  -24.0817    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.4570  -22.8586    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8755  -23.6704    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5832  -24.0797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2889  -23.6692    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2862  -22.8511    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5720  -22.4453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8692  -22.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4651  -25.3171    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   13.4664  -26.1343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7580  -26.5425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7590  -27.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4678  -27.7672    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1773  -27.3531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1728  -26.5380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0429  -22.8645    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.5842  -24.8969    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8770  -25.3064    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4702  -28.5844    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7637  -28.9950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.1791  -28.9909    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
  6 23  1  0
 11 24  1  0
 24 25  1  0
 20 26  1  0
 26 27  1  0
 26 28  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA4582323

   4-[3-Amino-2-[(2-methoxyphenyl)carbamoyl]phenyl]sulfanylbenzoic acid

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: 394.45

Molecular Weight (Monoisotopic): 394.0987

AlogP: 4.38

#Rotatable Bonds: 6

Polar Surface Area: 101.65

Molecular Species: ACID

HBA: 5

HBD: 3

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 4

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 4.04

CX Basic pKa: 1.84

CX LogP: 4.57

CX LogD: 1.44

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.54

Np Likeness Score: -1.08

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