3-[5-Bromo-2-(4-methoxy-benzyloxy)-phenyl]-4,5-dihydro-isoxazole-5-carboxylic acid methyl ester

ID: ALA313739

PubChem CID: 44318327

Max Phase: Preclinical

Molecular Formula: C19H18BrNO5

Molecular Weight: 420.26

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1CC(c2cc(Br)ccc2OCc2ccc(OC)cc2)=NO1

Standard InChI:  InChI=1S/C19H18BrNO5/c1-23-14-6-3-12(4-7-14)11-25-17-8-5-13(20)9-15(17)16-10-18(26-21-16)19(22)24-2/h3-9,18H,10-11H2,1-2H3

Standard InChI Key:  WDYUQOUGGLQNRI-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    2.5667    1.8833    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7292    1.0708    0.0000 C   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    0.6500    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
    3.5542    0.9750    0.0000 C   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
    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
    4.9542    2.6958    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
    5.2500    1.2958    0.0000 O   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
    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
   -0.1333   -3.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0417    1.5083    0.0000 C   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  5  1  0
  4  2  1  0
  5  1  1  0
  6  2  1  0
  7  3  1  0
  8  4  1  0
  9  4  2  0
 10  8  1  0
 11  7  2  0
 12  8  2  0
 13  9  1  0
 14 10  1  0
 15  7  1  0
 16 14  1  0
 17 22  1  0
 18 13  2  0
 19 13  1  0
 20 16  2  0
 21 16  1  0
 22 21  2  0
 23 20  1  0
 24 17  1  0
 25 15  1  0
 26 24  1  0
  3  6  1  0
 12 18  1  0
 17 23  2  0
M  END

Alternative Forms

1. Parent:

   

   ALA313739

   3-[5-Bromo-2-(4-methoxy-benzyloxy)-phenyl]-4,5-dihydro-isoxazole-5-carboxylic acid methyl 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: 420.26

Molecular Weight (Monoisotopic): 419.0368

AlogP: 3.70

#Rotatable Bonds: 6

Polar Surface Area: 66.35

Molecular Species: NEUTRAL

HBA: 6

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 1.62

CX LogP: 3.87

CX LogD: 3.87

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.67

Np Likeness Score: -0.72

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