N-(4-Amino-2-chloro-benzoyl)-4-chloro-benzenesulfonamide; Compound with Trifluoroacetic salt

ID: ALA1161726

PubChem CID: 46905535

Max Phase: Preclinical

Molecular Formula: C15H11Cl2F3N2O5S

Molecular Weight: 345.21

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(C(=O)NS(=O)(=O)c2ccc(Cl)cc2)c(Cl)c1.O=C(O)C(F)(F)F

Standard InChI:  InChI=1S/C13H10Cl2N2O3S.C2HF3O2/c14-8-1-4-10(5-2-8)21(19,20)17-13(18)11-6-3-9(16)7-12(11)15;3-2(4,5)1(6)7/h1-7H,16H2,(H,17,18);(H,6,7)

Standard InChI Key:  GXSNJRJFQMCFOY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 28  0  0  0  0  0  0  0  0999 V2000
    5.2792   -0.7625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792    0.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5667    0.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9917    0.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4542   -0.7625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.1042   -0.7625    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    5.2792   -1.5875    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5458    0.0833    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8250   -0.3250    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1125    0.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -0.3417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167    0.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1250    0.8000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9625   -0.6375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3958   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0375   -0.3375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1083    0.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2625    1.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9833    0.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0375   -1.1667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3167    0.9000    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.3167   -1.5792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6958    1.3333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7542   -1.5792    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6958    0.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9750    1.7458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4208    1.7500    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  2  2  0
  5  1  1  0
  6  1  1  0
  7  1  1  0
  9  8  1  0
 10  9  1  0
 11 10  1  0
 12 11  1  0
 13  8  1  0
 14  8  2  0
 15  8  2  0
 16 11  2  0
 17 12  2  0
 18 10  2  0
 19 13  2  0
 20 13  1  0
 21 17  1  0
 22 12  1  0
 23 16  1  0
 24 27  2  0
 25 21  1  0
 26 20  2  0
 27 19  1  0
 28 24  1  0
 26 24  1  0
 23 21  2  0
M  END

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: 345.21

Molecular Weight (Monoisotopic): 343.9789

AlogP: 2.69

#Rotatable Bonds: 3

Polar Surface Area: 89.26

Molecular Species: ACID

HBA: 4

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.29

CX Basic pKa: 2.19

CX LogP: 2.60

CX LogD: 1.86

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.84

Np Likeness Score: -1.50

References

1. Lobb KL, Hipskind PA, Aikins JA, Alvarez E, Cheung YY, Considine EL, De Dios A, Durst GL, Ferritto R, Grossman CS, Giera DD, Hollister BA, Huang Z, Iversen PW, Law KL, Li T, Lin HS, Lopez B, Lopez JE, Cabrejas LM, McCann DJ, Molero V, Reilly JE, Richett ME, Shih C, Teicher B, Wikel JH, White WT, Mader MM..  (2004)  Acyl sulfonamide anti-proliferatives: benzene substituent structure-activity relationships for a novel class of antitumor agents.,  47  (22): [PMID:15481975] [10.1021/jm030594r]

Source

Source(1):

• Scientific Literature