5-bromo-2-(4-chlorophenylsulfonamido)benzoic acid

ID: ALA212522

Cas Number: 107143-69-1

PubChem CID: 1069140

Max Phase: Preclinical

Molecular Formula: C13H9BrClNO4S

Molecular Weight: 390.64

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(O)c1cc(Br)ccc1NS(=O)(=O)c1ccc(Cl)cc1

Standard InChI:  InChI=1S/C13H9BrClNO4S/c14-8-1-6-12(11(7-8)13(17)18)16-21(19,20)10-4-2-9(15)3-5-10/h1-7,16H,(H,17,18)

Standard InChI Key:  JDVLYAYDIMUAAC-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    1.2553    3.4399    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.2553    2.6149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9698    2.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9698    1.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2553    0.9649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5409    1.3774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5409    2.2024    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2553    0.1399    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    1.2553   -0.6851    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0803    0.1399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4303    0.1399    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    0.0178   -0.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4303   -1.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0178   -2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8072   -2.0036    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197   -1.2891    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8072   -0.5746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197   -2.7180    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -1.2197    0.1399    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0447    0.1399    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8072    0.8543    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  2  3  1  0
  2  7  2  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  5  8  1  0
  6  7  1  0
  9  8  2  0
 10  8  2  0
 11  8  1  0
 12 11  1  0
 12 13  1  0
 12 17  2  0
 13 14  2  0
 14 15  1  0
 15 16  2  0
 18 15  1  0
 16 17  1  0
 17 19  1  0
 19 20  1  0
 19 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA212522

   5-Bromo-2-{[(4-chlorophenyl)sulfonyl]amino}benzoic acid

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: 390.64

Molecular Weight (Monoisotopic): 388.9124

AlogP: 3.60

#Rotatable Bonds: 4

Polar Surface Area: 83.47

Molecular Species: ACID

HBA: 3

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 3.87

CX Basic pKa: ┄

CX LogP: 3.49

CX LogD: 0.18

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.84

Np Likeness Score: -1.70

References

1. Kawai M, BaMaung NY, Fidanze SD, Erickson SA, Tedrow JS, Sanders WJ, Vasudevan A, Park C, Hutchins C, Comess KM, Kalvin D, Wang J, Zhang Q, Lou P, Tucker-Garcia L, Bouska J, Bell RL, Lesniewski R, Henkin J, Sheppard GS..  (2006)  Development of sulfonamide compounds as potent methionine aminopeptidase type II inhibitors with antiproliferative properties.,  16  (13): [PMID:16632353] [10.1016/j.bmcl.2006.03.085]

2. Wangtrakuldee P, Byrd MS, Campos CG, Henderson MW, Zhang Z, Clare M, Masoudi A, Myler PJ, Horn JR, Cotter PA, Hagen TJ..  (2013)  Discovery of Inhibitors of Burkholderia pseudomallei Methionine Aminopeptidase with Antibacterial Activity.,  4  (8): [PMID:24376907] [10.1021/ml400034m]

Source

Source(1):

• Scientific Literature