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

ID: ALA86294

PubChem CID: 44318134

Max Phase: Preclinical

Molecular Formula: C18H16ClNO3

Molecular Weight: 329.78

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(COc2ccc(-c3cc(CCl)on3)cc2)cc1

Standard InChI:  InChI=1S/C18H16ClNO3/c1-21-15-6-2-13(3-7-15)12-22-16-8-4-14(5-9-16)18-10-17(11-19)23-20-18/h2-10H,11-12H2,1H3

Standard InChI Key:  WRIIVVKXILQBIG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 23 25  0  0  0  0  0  0  0  0999 V2000
    2.2542    3.1333    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.1292    2.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8792    1.9458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0667    3.2708    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4542    2.5458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250    1.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042    2.3083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4250    1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7208    0.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083    1.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4458   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8708   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7208   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0083    1.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7042    0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2792    2.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1583   -0.1792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4458   -1.4167    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1583   -1.8292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8708   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6042    1.6958    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   -3.5958   -1.8417    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3125   -1.4292    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  4  1  0
  6  2  1  0
  7  6  2  0
  8  6  1  0
  9 10  1  0
 10 15  1  0
 11 13  1  0
 12 19  1  0
 13  9  1  0
 14  7  1  0
 15  8  2  0
 16  5  1  0
 17 11  2  0
 18 11  1  0
 19 18  2  0
 20 17  1  0
 21 16  1  0
 22 12  1  0
 23 22  1  0
  5  3  2  0
 10 14  2  0
 12 20  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA86294

   5-(Chloromethyl)-3-[4-[(4-methoxyphenyl)methoxy]phenyl]-1,2-oxazole

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: 329.78

Molecular Weight (Monoisotopic): 329.0819

AlogP: 4.67

#Rotatable Bonds: 6

Polar Surface Area: 44.49

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.29

CX LogD: 4.29

Aromatic Rings: 3

Heavy Atoms: 23

QED Weighted: 0.62

Np Likeness Score: -1.05

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