4-(2,5-difluorophenyl)-5-(3-fluoro-4-(methylsulfonyl)phenyl)-2,2-dimethylfuran-3(2H)-one

ID: ALA3979155

PubChem CID: 18386097

Max Phase: Preclinical

Molecular Formula: C19H15F3O4S

Molecular Weight: 396.39

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)OC(c2ccc(S(C)(=O)=O)c(F)c2)=C(c2cc(F)ccc2F)C1=O

Standard InChI:  InChI=1S/C19H15F3O4S/c1-19(2)18(23)16(12-9-11(20)5-6-13(12)21)17(26-19)10-4-7-15(14(22)8-10)27(3,24)25/h4-9H,1-3H3

Standard InChI Key:  LKKHZCDZQZQBFX-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   37.1203  -20.9828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.7158  -20.2771    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3069  -20.9802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.4056  -15.5733    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   34.3674  -16.3934    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   35.0967  -16.0164    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   36.0552  -19.8015    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   37.3786  -19.7952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.1211  -19.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.3048  -19.0246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.1565  -20.0456    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   35.8216  -18.3675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   36.1510  -17.6184    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.6672  -16.9607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.8541  -17.0509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   34.5272  -17.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.0129  -18.4590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.5936  -18.3551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.4078  -18.4360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.8831  -17.7722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   38.5453  -17.0271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.7275  -16.9499    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   37.2559  -17.6147    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   33.5567  -16.4851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   35.9953  -16.2123    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   38.7449  -19.1804    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   37.3870  -16.2070    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3  2  1  0
  5  4  2  0
  6  5  2  0
  7  2  1  0
  2  8  1  0
  8  9  1  0
  9 10  2  0
 10  7  1  0
  8 11  2  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 12  1  0
 10 12  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 18  1  0
  9 18  1  0
 15  5  1  0
  5 24  1  0
 14 25  1  0
 19 26  1  0
 22 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3979155

   4-(2,5-Difluorophenyl)-5-(3-fluoro-4-methylsulfonylphenyl)-2,2-dimethylfuran-3-one

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: 396.39

Molecular Weight (Monoisotopic): 396.0643

AlogP: 3.75

#Rotatable Bonds: 3

Polar Surface Area: 60.44

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 3.46

CX LogD: 3.46

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.79

Np Likeness Score: -0.57

References

1.  (2002)  4,5-diaryl-3(2H)-furanone derivatives as cyclooxygenase-2 inhibitors, 

Source

Source(1):

• Patent Bioactivity Data