N-(Biphenyl-4-ylmethyl)-5-bromo-1H-indole-2-sulfonamide

ID: ALA4476181

PubChem CID: 66547074

Max Phase: Preclinical

Molecular Formula: C21H17BrN2O2S

Molecular Weight: 441.35

Molecule Type: Unknown

Names and Identifiers

Canonical SMILES:  O=S(=O)(NCc1ccc(-c2ccccc2)cc1)c1cc2cc(Br)ccc2[nH]1

Standard InChI:  InChI=1S/C21H17BrN2O2S/c22-19-10-11-20-18(12-19)13-21(24-20)27(25,26)23-14-15-6-8-17(9-7-15)16-4-2-1-3-5-16/h1-13,23-24H,14H2

Standard InChI Key:  BTSRRDYCHLMCRE-UHFFFAOYSA-N

Molfile:  

 
     RDKit          2D

 27 30  0  0  0  0  0  0  0  0999 V2000
   34.2601   -6.2651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.2643   -7.0823    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   34.9699   -6.6702    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   30.7671   -6.6902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.7659   -7.5097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4740   -7.9187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4722   -6.2813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1808   -6.6866    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.1856   -7.5098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9700   -7.7596    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   33.4500   -7.0908    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.9622   -6.4277    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.6800   -7.7912    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   35.4971   -7.7864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9099   -8.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.5045   -9.2002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9166   -9.9050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7346   -9.9006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1389   -9.1855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7244   -8.4836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1491  -10.6029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7439  -11.3138    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1569  -12.0181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9750  -12.0126    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.3782  -11.2970    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.9629  -10.5956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0593   -6.2818    0.0000 Br  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  9  2  0
  8  7  2  0
  7  4  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  2  0
 12  8  1  0
 11  2  1  0
  2 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 21 22  2  0
 22 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 21  1  0
 18 21  1  0
  4 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4476181

   5-bromo-N-[(4-phenylphenyl)methyl]-1H-indole-2-sulfonamide

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: 441.35

Molecular Weight (Monoisotopic): 440.0194

AlogP: 5.08

#Rotatable Bonds: 5

Polar Surface Area: 61.96

Molecular Species: NEUTRAL

HBA: 2

HBD: 2

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 9.66

CX Basic pKa: ┄

CX LogP: 5.13

CX LogD: 5.13

Aromatic Rings: 4

Heavy Atoms: 27

QED Weighted: 0.45

Np Likeness Score: -0.97

References

1. Greig IR, Baillie GL, Abdelrahman M, Trembleau L, Ross RA..  (2016)  Development of indole sulfonamides as cannabinoid receptor negative allosteric modulators.,  26  (18): [PMID:27542310] [10.1016/j.bmcl.2016.08.018]

Source

Source(1):

• Scientific Literature