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

ID: ALA82279

PubChem CID: 44318382

Max Phase: Preclinical

Molecular Formula: C19H19NO5

Molecular Weight: 341.36

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COC(=O)C1CC(c2ccccc2OCc2ccc(OC)cc2)=NO1

Standard InChI:  InChI=1S/C19H19NO5/c1-22-14-9-7-13(8-10-14)12-24-17-6-4-3-5-15(17)16-11-18(25-20-16)19(21)23-2/h3-10,18H,11-12H2,1-2H3

Standard InChI Key:  NFEWQGCEMFKXSW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  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
    3.9500    1.7333    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    0.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7542    1.9083    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
    2.7917   -0.5917    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0125    2.6958    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
    5.3042    1.2958    0.0000 O   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
    2.0667   -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
    0.6417   -1.8375    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
    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
    1.3625   -0.5917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1167    1.4625    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  4  1  0
  4  1  1  0
  5  2  1  0
  6  2  1  0
  7  3  1  0
  8  6  1  0
  9  8  1  0
 10  7  2  0
 11  9  1  0
 12  7  1  0
 13 11  1  0
 14 17  2  0
 15 13  1  0
 16 13  2  0
 17 16  1  0
 18 15  2  0
 19  6  2  0
 20 14  1  0
 21  8  2  0
 22 12  1  0
 23 20  1  0
 24 19  1  0
 25 24  2  0
  3  5  1  0
 21 25  1  0
 18 14  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA82279

   3-[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: 341.36

Molecular Weight (Monoisotopic): 341.1263

AlogP: 2.94

#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: 2.13

CX LogP: 3.10

CX LogD: 3.10

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.76

Np Likeness Score: -0.66

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