5-(3-(3-chlorophenyl)-5-(4-methoxyphenyl)-4,5-dihydroisoxazole-4-carbonyl)-2-hydroxybenzoic acid

ID: ALA3780779

PubChem CID: 127031678

Max Phase: Preclinical

Molecular Formula: C24H18ClNO6

Molecular Weight: 451.86

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(C2ON=C(c3cccc(Cl)c3)C2C(=O)c2ccc(O)c(C(=O)O)c2)cc1

Standard InChI:  InChI=1S/C24H18ClNO6/c1-31-17-8-5-13(6-9-17)23-20(21(26-32-23)14-3-2-4-16(25)11-14)22(28)15-7-10-19(27)18(12-15)24(29)30/h2-12,20,23,27H,1H3,(H,29,30)

Standard InChI Key:  IMMCHYZAOOQSBW-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
    4.2010   -3.2956    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7343   -2.9815    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5987   -1.5004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9511   -0.8815    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9531   -1.9978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990    0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2990   -0.7500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.5000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2567    0.5852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3615    1.3842    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6819    1.0557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9901    2.5237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4154    2.9910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5328    1.9902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2247    0.5221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7994    0.0549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7206    4.4604    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8256    5.2598    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.8602    4.8362    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.6731    2.3640    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4458   -1.8433    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1563   -0.5278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6557   -0.4861    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4415   -1.7638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7280   -3.0832    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2285   -3.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6003    1.4977    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6387    0.8962    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3566   -4.1053    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  1  2  0
  3  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11  6  1  0
  4 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 16 20  1  0
 20 21  2  0
 20 22  1  0
 17 23  1  0
  5 24  1  0
 24 25  2  0
 25 26  1  0
 26 27  2  0
 27 28  1  0
 28 29  2  0
 29 24  1  0
  9 30  1  0
 30 31  1  0
 28 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3780779

   ---

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: 451.86

Molecular Weight (Monoisotopic): 451.0823

AlogP: 4.73

#Rotatable Bonds: 6

Polar Surface Area: 105.42

Molecular Species: ACID

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 2.68

CX Basic pKa: 1.78

CX LogP: 5.25

CX LogD: 2.07

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.52

Np Likeness Score: -0.22

References

1. Puttaswamy N, Pavan Kumar GS, Al-Ghorbani M, Vigneshwaran V, Prabhakar BT, Khanum SA..  (2016)  Synthesis and biological evaluation of salicylic acid conjugated isoxazoline analogues on immune cell proliferation and angiogenesis.,  114  [PMID:26974382] [10.1016/j.ejmech.2016.02.052]

Source

Source(1):

• Scientific Literature