2-(3-Chloro-4-fluoro-phenoxy)-N-[5-(thiazol-2-ylsulfamoyl)-quinolin-8-yl]-acetamide

ID: ALA3934711

PubChem CID: 16051137

Max Phase: Preclinical

Molecular Formula: C20H14ClFN4O4S2

Molecular Weight: 492.94

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  O=C(COc1ccc(F)c(Cl)c1)Nc1ccc(S(=O)(=O)Nc2nccs2)c2cccnc12

Standard InChI:  InChI=1S/C20H14ClFN4O4S2/c21-14-10-12(3-4-15(14)22)30-11-18(27)25-16-5-6-17(13-2-1-7-23-19(13)16)32(28,29)26-20-24-8-9-31-20/h1-10H,11H2,(H,24,26)(H,25,27)

Standard InChI Key:  SMKHGQCSIXVCGB-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 32 35  0  0  0  0  0  0  0  0999 V2000
   25.1846   -4.6696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1846   -5.4846    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8924   -5.8921    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   25.8924   -6.7071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5948   -7.1190    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.5948   -7.9305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8909   -8.3381    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1803   -7.9355    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1803   -7.1171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.8909   -9.1531    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   26.5945   -9.5606    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   26.5945  -10.3756    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.3185  -10.7931    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   27.1318  -11.6269    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   26.3189  -11.7072    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.9852  -10.9381    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   25.0737   -9.1531    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   25.4823   -9.8602    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   27.3035   -8.3393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0045   -7.9288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   28.0045   -7.1191    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   27.2984   -6.7125    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   24.4769   -5.8921    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4769   -4.2621    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   24.4769   -3.4472    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7703   -3.0393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.7703   -2.2237    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4783   -1.8161    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1848   -2.2229    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.1848   -3.0371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.4783   -1.0011    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.0666   -1.8163    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
  5  4  2  0
  6  5  1  0
  7  6  2  0
  8  7  1  0
  9  8  2  0
  4  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  0
 13 12  2  0
 13 14  1  0
 14 15  2  0
 16 15  1  0
 12 16  1  0
 10 17  2  0
 10 18  2  0
  6 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
  5 22  1  0
  2 23  2  0
  1 24  1  0
 24 25  1  0
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 27 26  1  0
 28 27  2  0
 29 28  1  0
 30 29  2  0
 25 30  1  0
 28 31  1  0
 27 32  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA3934711

   2-(3-chloro-4-fluorophenoxy)-N-[5-(1,3-thiazol-2-ylsulfamoyl)quinolin-8-yl]acetamide

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: 492.94

Molecular Weight (Monoisotopic): 492.0129

AlogP: 4.30

#Rotatable Bonds: 7

Polar Surface Area: 110.28

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 8

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 6.68

CX Basic pKa: 1.02

CX LogP: 3.46

CX LogD: 2.87

Aromatic Rings: 4

Heavy Atoms: 32

QED Weighted: 0.40

Np Likeness Score: -2.50

References

1.  (2012)  Bicyclic derivatives as modulators of voltage gated ion channels, 

Source

Source(1):

• Patent Bioactivity Data