5-(4-((trans)-4-(5-(trifluoromethyl)pyridin-2-ylamino)cyclohexylsulfonyl)phenyl)picolinonitrile

ID: ALA4249063

PubChem CID: 145985807

Max Phase: Preclinical

Molecular Formula: C24H21F3N4O2S

Molecular Weight: 486.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(-c2ccc(S(=O)(=O)[C@H]3CC[C@H](Nc4ccc(C(F)(F)F)cn4)CC3)cc2)cn1

Standard InChI:  InChI=1S/C24H21F3N4O2S/c25-24(26,27)18-4-12-23(30-15-18)31-19-6-10-22(11-7-19)34(32,33)21-8-2-16(3-9-21)17-1-5-20(13-28)29-14-17/h1-5,8-9,12,14-15,19,22H,6-7,10-11H2,(H,30,31)/t19-,22-

Standard InChI Key:  FDAZEQODSOATPX-XYWHTSSQSA-N

Molfile:  

     RDKit          2D

 34 37  0  0  0  0  0  0  0  0999 V2000
   13.4533   -6.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4522   -6.8907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1602   -7.2996    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.8699   -6.8902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8671   -6.0675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1585   -5.6623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5783   -7.2977    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.2853   -6.8880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9920   -7.3011    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6970   -6.8948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6999   -6.0773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9917   -5.6676    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.2806   -6.0755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.4085   -5.6703    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.1153   -6.0804    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9947   -4.9568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.8119   -4.9568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1086   -6.8977    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8146   -7.3077    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5242   -6.9007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5234   -6.0792    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.8168   -5.6728    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2315   -7.3099    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2270   -8.1276    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9335   -8.5367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6426   -8.1287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.6406   -7.3073    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.9336   -6.9018    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7455   -5.6627    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0379   -6.0715    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   12.3322   -4.9527    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   13.1494   -4.9527    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
   23.3504   -8.5370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.0535   -8.9437    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  2  0
  6  1  1  0
  4  7  1  0
  8  7  1  6
  8  9  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
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 11 14  1  1
 14 15  1  0
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 14 17  2  0
 15 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 21 22  2  0
 22 15  1  0
 20 23  1  0
 23 24  2  0
 24 25  1  0
 25 26  2  0
 26 27  1  0
 27 28  2  0
 28 23  1  0
  1 29  1  0
 29 30  1  0
 29 31  1  0
 29 32  1  0
 26 33  1  0
 33 34  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4249063

   ---

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: 486.52

Molecular Weight (Monoisotopic): 486.1337

AlogP: 5.23

#Rotatable Bonds: 5

Polar Surface Area: 95.74

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 5.43

CX LogP: 4.42

CX LogD: 4.42

Aromatic Rings: 3

Heavy Atoms: 34

QED Weighted: 0.53

Np Likeness Score: -1.59

References

1. Tawaraishi T, Sakauchi N, Hidaka K, Yoshikawa K, Okui T, Kuno H, Chisaki I, Aso K..  (2018)  Identification of a novel series of potent and selective CCR6 inhibitors as biological probes.,  28  (18): [PMID:30098865] [10.1016/j.bmcl.2018.07.042]

2. Tawaraishi, Taisuke T and 7 more authors.  2018-10-01  Identification of a novel series of potent and selective CCR6 inhibitors as biological probes.  [PMID:30098865]

Source

Source(1):

• Scientific Literature