6-(2,4-Difluorophenyl)-3-(2,5-difluorophenyl)-2H-benzo[e][1,3]oxazine-2,4(3H)-dione

ID: ALA3596952

Max Phase: Preclinical

Molecular Formula: C20H9F4NO3

Molecular Weight: 387.29

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=c1oc2ccc(-c3ccc(F)cc3F)cc2c(=O)n1-c1cc(F)ccc1F

Standard InChI:  InChI=1S/C20H9F4NO3/c21-11-2-4-13(16(24)8-11)10-1-6-18-14(7-10)19(26)25(20(27)28-18)17-9-12(22)3-5-15(17)23/h1-9H

Standard InChI Key:  NGYJGOKTIPSUCV-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   -2.6111    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6111   -0.7486    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964    1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929    0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5929   -0.7486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2964   -1.4973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6486    1.3517    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2928   -2.6973    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8926   -1.4990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8951   -2.9990    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1953   -3.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4931   -2.9949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4907   -1.4949    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1905   -0.7469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5333   -3.5932    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.8568   -3.6007    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9086   -1.5029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2071   -0.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5067   -1.5010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5078   -3.0010    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2092   -3.7519    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9097   -3.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8709   -3.6035    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5455   -0.9002    0.0000 F   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  6  1  0
  1  6  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
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  6  7  2  0
  2 11  2  0
  4 12  2  0
 13 14  1  0
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 16 19  1  0
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  9 13  1  0
 21 22  1  0
 22 23  2  0
 23 24  1  0
 24 25  2  0
 25 26  1  0
 21 26  2  0
  3 21  1  0
 26 27  1  0
 23 28  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3596952

   ---

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: 387.29

Molecular Weight (Monoisotopic): 387.0519

AlogP: 4.17

#Rotatable Bonds: 2

Polar Surface Area: 52.21

Molecular Species: ┄

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 5.03

CX LogD: 5.03

Aromatic Rings: 4

Heavy Atoms: 28

QED Weighted: 0.49

Np Likeness Score: -0.90

References

1. Lee CC, Liu FL, Chen CL, Chen TC, Liu FC, Ahmed Ali AA, Chang DM, Huang HS..  (2015)  Novel inhibitors of RANKL-induced osteoclastogenesis: Design, synthesis, and biological evaluation of 6-(2,4-difluorophenyl)-3-phenyl-2H-benzo[e][1,3]oxazine-2,4(3H)-diones.,  23  (15): [PMID:26081760] [10.1016/j.bmc.2015.06.007]

Source

Source(1):

• Scientific Literature