5-butyl-2-(phenylsulfonamido)benzoic acid

ID: ALA425776

PubChem CID: 10246233

Max Phase: Preclinical

Molecular Formula: C17H19NO4S

Molecular Weight: 333.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCc1ccc(NS(=O)(=O)c2ccccc2)c(C(=O)O)c1

Standard InChI:  InChI=1S/C17H19NO4S/c1-2-3-7-13-10-11-16(15(12-13)17(19)20)18-23(21,22)14-8-5-4-6-9-14/h4-6,8-12,18H,2-3,7H2,1H3,(H,19,20)

Standard InChI Key:  GUFYXBDBRAROGG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 24  0  0  0  0  0  0  0  0999 V2000
    1.7031   -7.8023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7020   -8.6294    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4163   -9.0423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1322   -8.6291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1295   -7.7989    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4146   -7.3895    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8425   -7.3839    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    4.5584   -7.7940    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.4206   -6.7984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.2571   -6.7984    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.2715   -7.3792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9846   -7.7939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6971   -7.3797    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6948   -6.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9740   -6.1439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2644   -6.5605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9850   -8.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2704   -9.0348    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6994   -9.0349    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4073   -6.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1237   -6.5471    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1276   -7.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8440   -7.7812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  5  6  2  0
 11 12  2  0
  6  1  1  0
 12 13  1  0
  1  2  2  0
 13 14  2  0
  5  7  1  0
 14 15  1  0
  3  4  2  0
 15 16  2  0
 16 11  1  0
  7  8  1  0
  7  9  2  0
 17 18  1  0
 17 19  2  0
 12 17  1  0
  4  5  1  0
 14 20  1  0
  7 10  2  0
 20 21  1  0
  2  3  1  0
 21 22  1  0
  8 11  1  0
 22 23  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA425776

   2-Benzenesulfonamido-5-butylbenzoic 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: 333.41

Molecular Weight (Monoisotopic): 333.1035

AlogP: 3.53

#Rotatable Bonds: 7

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: 4.02

CX Basic pKa: ┄

CX LogP: 3.97

CX LogD: 0.76

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.81

Np Likeness Score: -1.11

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]

Source

Source(1):

• Scientific Literature