4-(5-fluoro-2-methylphenyl)-2,2-dimethyl-5-(4-(methylsulfonyl)phenyl)furan-3(2H)-one

ID: ALA3980214

PubChem CID: 18386107

Max Phase: Preclinical

Molecular Formula: C20H19FO4S

Molecular Weight: 374.43

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(F)cc1C1=C(c2ccc(S(C)(=O)=O)cc2)OC(C)(C)C1=O

Standard InChI:  InChI=1S/C20H19FO4S/c1-12-5-8-14(21)11-16(12)17-18(25-20(2,3)19(17)22)13-6-9-15(10-7-13)26(4,23)24/h5-11H,1-4H3

Standard InChI Key:  HGFHITLLCCLRII-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   19.0590   -8.8956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8463   -9.6963    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.6461   -9.4802    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.6072  -14.3464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.1984  -13.6332    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7851  -14.3438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5335  -13.1489    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.8709  -13.1497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.6149  -12.3619    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.7901  -12.3652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6556  -13.4069    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.3060  -11.7025    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.6429  -10.9474    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1576  -10.2802    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3356  -10.3669    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.0011  -11.1265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4884  -11.7905    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0956  -11.6938    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9181  -11.7799    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4019  -11.1118    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.0646  -10.3571    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2387  -10.2746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.7584  -10.9437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0277   -9.7881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.2546  -12.5340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8987   -9.5221    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  5  4  1  0
  6  5  1  0
  7  5  1  0
  5  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  2  1  0
  2 24  1  0
 19 25  1  0
 22 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3980214

   4-(5-Fluoro-2-methylphenyl)-2,2-dimethyl-5-(4-methylsulfonylphenyl)furan-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: 374.43

Molecular Weight (Monoisotopic): 374.0988

AlogP: 3.78

#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: 3.69

CX LogD: 3.69

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.82

Np Likeness Score: -0.44

References

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

Source

Source(1):

• Patent Bioactivity Data