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

ID: ALA113346

PubChem CID: 44340725

Max Phase: Preclinical

Molecular Formula: C15H13N3O3S

Molecular Weight: 315.35

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ccc(S(=O)(=O)Nc2cc(-c3ccccc3)no2)cc1

Standard InChI:  InChI=1S/C15H13N3O3S/c16-12-6-8-13(9-7-12)22(19,20)18-15-10-14(17-21-15)11-4-2-1-3-5-11/h1-10,18H,16H2

Standard InChI Key:  HLZIBNXMFTXXQS-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    5.4500   -7.5375    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    6.6875   -6.8167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2750   -7.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.4917   -6.7250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9500   -5.5042    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.6625   -5.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3375   -6.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6250   -7.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4500   -8.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.4500   -6.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.4167   -5.5875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2125   -6.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9792   -7.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1542   -7.5375    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.3875   -8.2500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3875   -6.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0792   -6.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5000   -4.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2500   -4.4375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8375   -5.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.9250   -4.9250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  3  1  0
  3  1  1  0
  4  2  2  0
  5  7  1  0
  6  4  1  0
  7  2  1  0
  8  1  1  0
  9  1  2  0
 10  1  2  0
 11  6  1  0
 12  8  1  0
 13  8  2  0
 14 17  2  0
 15 14  1  0
 16 12  2  0
 17 13  1  0
 18 11  2  0
 19 11  1  0
 20 19  2  0
 21 18  1  0
 22 20  1  0
 16 14  1  0
  6  5  2  0
 21 22  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA113346

   4-amino-N-(3-phenyl-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: 315.35

Molecular Weight (Monoisotopic): 315.0678

AlogP: 2.72

#Rotatable Bonds: 4

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: 5.71

CX Basic pKa: 2.08

CX LogP: 2.12

CX LogD: 1.24

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.72

Np Likeness Score: -1.54

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