5-Chloromethyl-3-[2-(4-methoxy-benzyloxy)-phenyl]-4,5-dihydro-isoxazole

ID: ALA81938

PubChem CID: 44318404

Max Phase: Preclinical

Molecular Formula: C18H18ClNO3

Molecular Weight: 331.80

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(COc2ccccc2C2=NOC(CCl)C2)cc1

Standard InChI:  InChI=1S/C18H18ClNO3/c1-21-14-8-6-13(7-9-14)12-22-18-5-3-2-4-16(18)17-10-15(11-19)23-20-17/h2-9,15H,10-12H2,1H3

Standard InChI Key:  VKCBXAWKAWNCPW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    2.6292    1.8833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917    1.0708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792    0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3417    2.2833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6167    0.9750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0792   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9500    1.7333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -0.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7917   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417   -2.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -1.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0667   -2.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -3.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417   -1.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3250    1.3083    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    1.3542    1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0833   -3.0792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7625    1.9208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3625   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7958   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417    0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6417   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  1  0
  4  1  1  0
  5  2  1  0
  6  3  1  0
  7  4  1  0
  8  6  1  0
  9  8  1  0
 10  9  1  0
 11 14  1  0
 12 10  2  0
 13 10  1  0
 14 13  2  0
 15 12  1  0
 16 19  1  0
 17  3  2  0
 18 11  1  0
 19  7  1  0
 20  6  2  0
 21 18  1  0
 22 17  1  0
 23 22  2  0
  7  5  1  0
 20 23  1  0
 11 15  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA81938

   5-Chloromethyl-3-[2-(4-methoxy-benzyloxy)-phenyl]-4,5-dihydro-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: 331.80

Molecular Weight (Monoisotopic): 331.0975

AlogP: 4.01

#Rotatable Bonds: 6

Polar Surface Area: 40.05

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.08

CX LogP: 3.99

CX LogD: 3.99

Aromatic Rings: 2

Heavy Atoms: 23

QED Weighted: 0.75

Np Likeness Score: -0.65

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