4-(3-(3-chlorophenyl)-5,5-dimethyl-4-oxo-4,5-dihydrofuran-2-yl)-2-fluorobenzenesulfonamide

ID: ALA3985744

PubChem CID: 18385685

Max Phase: Preclinical

Molecular Formula: C18H15ClFNO4S

Molecular Weight: 395.84

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC1(C)OC(c2ccc(S(N)(=O)=O)c(F)c2)=C(c2cccc(Cl)c2)C1=O

Standard InChI:  InChI=1S/C18H15ClFNO4S/c1-18(2)17(22)15(10-4-3-5-12(19)8-10)16(25-18)11-6-7-14(13(20)9-11)26(21,23)24/h3-9H,1-2H3,(H2,21,23,24)

Standard InChI Key:  GNYXNVTTYSKYQM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   30.9955   -6.2321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.5910   -5.5264    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1820   -6.2295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.2808   -0.8225    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   28.2426   -1.6426    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   28.9719   -1.2657    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.9304   -5.0508    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   31.2538   -5.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.9963   -4.2663    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.1800   -4.2739    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.0317   -5.2949    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   29.6968   -3.6168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   30.0262   -2.8677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   29.5424   -2.2100    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.7293   -2.3002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.4024   -3.0538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.8881   -3.7083    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.4687   -3.6044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.2830   -3.6853    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.7583   -3.0215    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   32.4205   -2.2764    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.6027   -2.1992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   31.1310   -2.8640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.4319   -1.7344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   29.8705   -1.4616    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   33.5716   -3.1013    0.0000 Cl  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
 20 26  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3985744

   4-[3-(3-Chlorophenyl)-5,5-dimethyl-4-oxofuran-2-yl]-2-fluorobenzenesulfonamide

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: 395.84

Molecular Weight (Monoisotopic): 395.0394

AlogP: 3.37

#Rotatable Bonds: 3

Polar Surface Area: 86.46

Molecular Species: NEUTRAL

HBA: 4

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 5

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.63

CX Basic pKa: ┄

CX LogP: 3.55

CX LogD: 3.53

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.86

Np Likeness Score: -0.60

References

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

Source

Source(1):

• Patent Bioactivity Data