2-(phenylsulfonamido)-5-propylbenzoic acid

ID: ALA209071

Cas Number: 677290-38-9

PubChem CID: 10018850

Max Phase: Preclinical

Molecular Formula: C16H17NO4S

Molecular Weight: 319.38

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCc1ccc(NS(=O)(=O)c2ccccc2)c(C(=O)O)c1

Standard InChI:  InChI=1S/C16H17NO4S/c1-2-6-12-9-10-15(14(11-12)16(18)19)17-22(20,21)13-7-4-3-5-8-13/h3-5,7-11,17H,2,6H2,1H3,(H,18,19)

Standard InChI Key:  LZDCSXYOKAIIJO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 23  0  0  0  0  0  0  0  0999 V2000
   -5.2353   -7.7050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2364   -8.5322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5221   -8.9450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8063   -8.5318    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8090   -7.7016    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5237   -7.2922    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0959   -7.2867    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3801   -7.6968    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5177   -6.7010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6813   -6.7010    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6670   -7.2819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9538   -7.6966    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2412   -7.2824    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2436   -6.4565    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9645   -6.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6741   -6.4633    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9535   -8.5250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6679   -8.9375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2390   -8.9376    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4689   -6.0407    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1853   -6.4498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1892   -7.2748    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  8 11  1  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
M  END

Alternative Forms

1. Parent:

   

   ALA209071

   2-Benzenesulfonamido-5-propylbenzoic 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: 319.38

Molecular Weight (Monoisotopic): 319.0878

AlogP: 3.14

#Rotatable Bonds: 6

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: 3.52

CX LogD: 0.31

Aromatic Rings: 2

Heavy Atoms: 22

QED Weighted: 0.86

Np Likeness Score: -1.21

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