3-(7-fluoro-4-(3-fluorophenyl)quinolin-3-ylsulfonyl)benzonitrile

ID: ALA4097400

PubChem CID: 25168931

Max Phase: Preclinical

Molecular Formula: C22H12F2N2O2S

Molecular Weight: 406.41

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cccc(S(=O)(=O)c2cnc3cc(F)ccc3c2-c2cccc(F)c2)c1

Standard InChI:  InChI=1S/C22H12F2N2O2S/c23-16-5-2-4-15(10-16)22-19-8-7-17(24)11-20(19)26-13-21(22)29(27,28)18-6-1-3-14(9-18)12-25/h1-11,13H

Standard InChI Key:  ZBYWVLGWPNTBNO-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

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   16.3204   -6.5639    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   16.7336   -5.8462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   14.8903   -8.2203    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.1794   -7.8073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1808   -6.9878    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4699   -6.5727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7533   -6.9855    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7540   -7.8052    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4713   -8.2203    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8889   -6.5749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8882   -5.7489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1773   -5.3338    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1765   -4.5080    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8868   -4.0950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6019   -4.5101    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6025   -5.3360    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6061   -6.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0453   -6.9746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0445   -7.7969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7590   -8.2131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4805   -7.7946    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4687   -6.9660    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7523   -6.5622    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.6047   -7.8095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4640   -4.0985    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   19.1753   -6.5464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8818   -6.1267    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   12.0394   -8.2176    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  1  0
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  6  7  2  0
  7  8  1  0
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  2 19  1  0
 19 20  2  0
 21 20  1  0
 22 21  2  0
 23 22  1  0
 24 23  2  0
 19 24  1  0
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  4 25  2  0
 14 26  1  0
 23 27  1  0
 27 28  3  0
  9 29  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4097400

   3-[7-Fluoro-4-(3-fluorophenyl)quinolin-3-yl]sulfonylbenzonitrile

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: 406.41

Molecular Weight (Monoisotopic): 406.0588

AlogP: 4.88

#Rotatable Bonds: 3

Polar Surface Area: 70.82

Molecular Species: NEUTRAL

HBA: 4

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 4

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 0.23

CX LogP: 4.87

CX LogD: 4.87

Aromatic Rings: 4

Heavy Atoms: 29

QED Weighted: 0.49

Np Likeness Score: -1.61

References

1. Galambos J, Bielik A, Krasavin M, Orgován Z, Domány G, Nógrádi K, Wágner G, Balogh GT, Béni Z, Kóti J, Szakács Z, Bobok A, Kolok S, Mikó-Bakk ML, Vastag M, Sághy K, Laszy J, Halász AS, Balázs O, Gál K, Greiner I, Szombathelyi Z, Keserű GM..  (2017)  Discovery and Preclinical Characterization of 3-((4-(4-Chlorophenyl)-7-fluoroquinoline-3-yl)sulfonyl)benzonitrile, a Novel Non-acetylenic Metabotropic Glutamate Receptor 5 (mGluR5) Negative Allosteric Modulator for Psychiatric Indications.,  60  (6): [PMID:28212015] [10.1021/acs.jmedchem.6b01858]

Source

Source(1):

• Scientific Literature