3-[2-(4-Bromo-benzyloxy)-phenyl]-isoxazole-4,5-dicarboxylic acid dimethyl ester

ID: ALA84000

PubChem CID: 44318271

Max Phase: Preclinical

Molecular Formula: C20H16BrNO6

Molecular Weight: 446.25

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)c1onc(-c2ccccc2OCc2ccc(Br)cc2)c1C(=O)OC

Standard InChI:  InChI=1S/C20H16BrNO6/c1-25-19(23)16-17(22-28-18(16)20(24)26-2)14-5-3-4-6-15(14)27-11-12-7-9-13(21)10-8-12/h3-10H,11H2,1-2H3

Standard InChI Key:  JHBIURTXBQDWRY-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 28 30  0  0  0  0  0  0  0  0999 V2000
    1.9375    1.3708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2667    2.1333    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125    1.4625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9500    2.2833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.6667    2.6833    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000    1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3500    0.6583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0792    2.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4000    0.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125   -0.1917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1750    0.6583    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3292    3.1083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9292   -0.0542    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.6417    1.7083    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1125   -1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0375   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3917   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7583   -2.6875    0.0000 Br  0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208    1.4583    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -2.6792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0375   -1.4417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3917   -2.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -1.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3208   -0.1917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4500    1.8958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3417   -0.7667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0333    1.0458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0333    0.2208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  1  1  0
  4  3  2  0
  5  2  1  0
  6  3  1  0
  7  1  1  0
  8  2  1  0
  9  6  1  0
 10  9  1  0
 11  7  2  0
 12  8  2  0
 13  7  1  0
 14  8  1  0
 15 10  1  0
 16 21  2  0
 17 15  1  0
 18 16  1  0
 19  6  2  0
 20 22  2  0
 21 23  1  0
 22 17  1  0
 23 17  2  0
 24  9  2  0
 25 14  1  0
 26 13  1  0
 27 19  1  0
 28 27  2  0
  4  5  1  0
 24 28  1  0
 20 16  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA84000

   3-[2-(4-Bromo-benzyloxy)-phenyl]-isoxazole-4,5-dicarboxylic acid dimethyl ester

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: 446.25

Molecular Weight (Monoisotopic): 445.0161

AlogP: 4.26

#Rotatable Bonds: 6

Polar Surface Area: 87.86

Molecular Species: NEUTRAL

HBA: 7

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 4.63

CX LogD: 4.63

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.52

Np Likeness Score: -0.75

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