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

ID: ALA431213

PubChem CID: 44462337

Max Phase: Preclinical

Molecular Formula: C18H15BrClNO3

Molecular Weight: 408.68

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(COc2ccc(Br)cc2-c2cc(CCl)on2)cc1

Standard InChI:  InChI=1S/C18H15BrClNO3/c1-22-14-5-2-12(3-6-14)11-23-18-7-4-13(19)8-16(18)17-9-15(10-20)24-21-17/h2-9H,10-11H2,1H3

Standard InChI Key:  BLQJSTICERNURY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    2.7292    1.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5667    1.8833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167    0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5542    0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2792    2.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8875    1.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0167   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917    1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292   -0.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3000   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792    0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792   -2.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333    1.0583    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
    4.6917    1.9083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -1.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0042   -2.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2917   -3.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5792   -1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2500    1.2958    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -3.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1333   -3.9000    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  4  2  0
  7  3  1  0
  8  3  2  0
  9  7  1  0
 10  7  2  0
 11  8  1  0
 12  9  1  0
 13 12  1  0
 14 20  1  0
 15 11  2  0
 16 11  1  0
 17  6  1  0
 18 13  2  0
 19 13  1  0
 20 19  2  0
 21 18  1  0
 22 17  1  0
 23 14  1  0
 24 23  1  0
  5  6  1  0
 10 15  1  0
 14 21  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA431213

   3-[5-Bromo-2-(4-methoxy-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: 408.68

Molecular Weight (Monoisotopic): 406.9924

AlogP: 5.43

#Rotatable Bonds: 6

Polar Surface Area: 44.49

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: 1

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.06

CX LogD: 5.06

Aromatic Rings: 3

Heavy Atoms: 24

QED Weighted: 0.51

Np Likeness Score: -1.07

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