4-Amino-N-(3-pentyl-isoxazol-5-yl)-benzenesulfonamide

ID: ALA326740

PubChem CID: 14973486

Max Phase: Preclinical

Molecular Formula: C14H19N3O3S

Molecular Weight: 309.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCc1cc(NS(=O)(=O)c2ccc(N)cc2)on1

Standard InChI:  InChI=1S/C14H19N3O3S/c1-2-3-4-5-12-10-14(20-16-12)17-21(18,19)13-8-6-11(15)7-9-13/h6-10,17H,2-5,15H2,1H3

Standard InChI Key:  UTXRMBWNFAVFAU-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 21 22  0  0  0  0  0  0  0  0999 V2000
    4.5542   -4.0667    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    5.3792   -4.0667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.7917   -3.3542    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6000   -3.2625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0542   -2.0417    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.4417   -2.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7292   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7667   -2.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -4.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5542   -3.2500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -3.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3167   -4.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0875   -4.0667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2625   -4.0667    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917   -3.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4917   -4.7875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5250   -2.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1917   -2.6125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6125   -2.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9417   -2.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3667   -2.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  4  3  2  0
  5  6  1  0
  6  3  1  0
  7  1  1  0
  8  4  1  0
  9  1  2  0
 10  1  2  0
 11  7  2  0
 12  7  1  0
 13 16  1  0
 14 13  1  0
 15 11  1  0
 16 12  2  0
 17  8  1  0
 18 17  1  0
 19 20  1  0
 20 18  1  0
 21 19  1  0
 15 13  2  0
  8  5  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA326740

   4-amino-N-(3-pentyl-1,2-oxazol-5-yl)benzenesulfonamide

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: 309.39

Molecular Weight (Monoisotopic): 309.1147

AlogP: 2.79

#Rotatable Bonds: 7

Polar Surface Area: 98.22

Molecular Species: ACID

HBA: 5

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 5.73

CX Basic pKa: 2.07

CX LogP: 2.25

CX LogD: 1.37

Aromatic Rings: 2

Heavy Atoms: 21

QED Weighted: 0.61

Np Likeness Score: -1.23

References

1. Stein PD, Hunt JT, Floyd DM, Moreland S, Dickinson KE, Mitchell C, Liu EC, Webb ML, Murugesan N, Dickey J..  (1994)  The discovery of sulfonamide endothelin antagonists and the development of the orally active ETA antagonist 5-(dimethylamino)-N-(3,4-dimethyl-5-isoxazolyl)-1-naphthalenesulf onamide.,  37  (3): [PMID:8308857] [10.1021/jm00029a001]

Source

Source(1):

• Scientific Literature