3-({7-chloro-4-[4-(hydroxymethyl)piperidin-1-yl]quinolin-3-yl}sulfonyl)-5-fluorobenzonitrile

ID: ALA4072908

PubChem CID: 137638572

Max Phase: Preclinical

Molecular Formula: C22H19ClFN3O3S

Molecular Weight: 459.93

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1cc(F)cc(S(=O)(=O)c2cnc3cc(Cl)ccc3c2N2CCC(CO)CC2)c1

Standard InChI:  InChI=1S/C22H19ClFN3O3S/c23-16-1-2-19-20(9-16)26-12-21(22(19)27-5-3-14(13-28)4-6-27)31(29,30)18-8-15(11-25)7-17(24)10-18/h1-2,7-10,12,14,28H,3-6,13H2

Standard InChI Key:  HKZHVRDHFXEJHG-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 31 34  0  0  0  0  0  0  0  0999 V2000
    9.0840   -7.3588    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.4968   -8.0687    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    9.9052   -7.3564    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0763   -9.6928    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.7793   -9.2883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7888   -8.4711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0871   -8.0585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3758   -8.4629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6699   -8.0461    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9586   -8.4505    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9532   -9.2677    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6591   -9.6804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3704   -9.2801    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0925   -7.2413    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   10.2033   -8.4872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1908   -9.3038    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8931   -9.7200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6063   -9.3192    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.6127   -8.4978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9097   -8.0852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8042   -6.8428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8115   -6.0292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1084   -5.6122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3962   -6.0148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3872   -6.8346    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2431   -9.6720    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
    8.1169   -4.7950    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4135   -4.3791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.8838  -10.5371    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.3234   -8.0944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0341   -7.6911    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  2  0
  3  2  2  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
  4 13  1  0
  8 13  1  0
  6  2  1  0
  7 14  1  0
  2 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
 14 21  1  0
 14 25  1  0
 21 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 11 26  1  0
 23 27  1  0
 27 28  1  0
 17 29  1  0
 19 30  1  0
 30 31  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4072908

   ---

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: 459.93

Molecular Weight (Monoisotopic): 459.0820

AlogP: 3.94

#Rotatable Bonds: 4

Polar Surface Area: 94.29

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 3.15

CX LogP: 3.58

CX LogD: 3.58

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.63

Np Likeness Score: -1.64

References

1. Galambos J, Bielik A, Wágner G, Domány G, Kóti J, Béni Z, Szigetvári Á, Sánta Z, Orgován Z, Bobok A, Kiss B, Mikó-Bakk ML, Vastag M, Sághy K, Krasavin M, Gál K, Greiner I, Szombathelyi Z, Keserű GM..  (2017)  Discovery of 4-amino-3-arylsulfoquinolines, a novel non-acetylenic chemotype of metabotropic glutamate 5 (mGlu5) receptor negative allosteric modulators.,  133  [PMID:28390229] [10.1016/j.ejmech.2017.03.071]

Source

Source(1):

• Scientific Literature