3-[2-(4-Bromo-benzyloxy)-phenyl]-5-chloromethyl-isoxazole

ID: ALA83758

PubChem CID: 44318656

Max Phase: Preclinical

Molecular Formula: C17H13BrClNO2

Molecular Weight: 378.65

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  ClCc1cc(-c2ccccc2OCc2ccc(Br)cc2)no1

Standard InChI:  InChI=1S/C17H13BrClNO2/c18-13-7-5-12(6-8-13)11-21-17-4-2-1-3-15(17)16-9-14(10-19)22-20-16/h1-9H,10-11H2

Standard InChI Key:  WWPOLSXCEBBWCP-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 22 24  0  0  0  0  0  0  0  0999 V2000
    1.8542    1.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9792    2.4458    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.6042    1.2583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417    1.2083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917    2.5833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1750    1.8583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1417    0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542   -0.0292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8542   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2958   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375   -1.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0125   -2.5292    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.0000    1.7583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250   -2.5167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2958   -1.2792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1375   -2.1042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4250   -0.8667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3292    1.0083    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    0.4250    1.6208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -0.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2875    1.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2875    0.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  1  1  0
  5  2  1  0
  6  3  2  0
  7  4  1  0
  8  7  1  0
  9  8  1  0
 10 15  2  0
 11  9  1  0
 12 10  1  0
 13  6  1  0
 14 16  2  0
 15 17  1  0
 16 11  1  0
 17 11  2  0
 18 13  1  0
 19  4  2  0
 20  7  2  0
 21 19  1  0
 22 21  2  0
  5  6  1  0
 20 22  1  0
 10 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA83758

   3-[2-(4-Bromo-benzyloxy)-phenyl]-5-chloromethyl-isoxazole

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: 378.65

Molecular Weight (Monoisotopic): 376.9818

AlogP: 5.42

#Rotatable Bonds: 5

Polar Surface Area: 35.26

Molecular Species: NEUTRAL

HBA: 3

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 3

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.21

CX LogD: 5.21

Aromatic Rings: 3

Heavy Atoms: 22

QED Weighted: 0.56

Np Likeness Score: -1.19

References

1. Sammelson RE, Ma T, Galietta LJ, Verkman AS, Kurth MJ..  (2003)  3-(2-Benzyloxyphenyl)isoxazoles and isoxazolines: synthesis and evaluation as CFTR activators.,  13  (15): [PMID:12852954] [10.1016/s0960-894x(03)00482-7]

Source

Source(1):

• Scientific Literature