2-(1-(4-methoxyphenylsulfonyl)piperidin-4-ylamino)isonicotinonitrile

ID: ALA4250223

PubChem CID: 145982885

Max Phase: Preclinical

Molecular Formula: C18H20N4O3S

Molecular Weight: 372.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)N2CCC(Nc3cc(C#N)ccn3)CC2)cc1

Standard InChI:  InChI=1S/C18H20N4O3S/c1-25-16-2-4-17(5-3-16)26(23,24)22-10-7-15(8-11-22)21-18-12-14(13-19)6-9-20-18/h2-6,9,12,15H,7-8,10-11H2,1H3,(H,20,21)

Standard InChI Key:  SLQVVLQNUARGFA-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
   13.8042  -11.4283    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.8030  -12.2478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5111  -12.6568    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   15.2207  -12.2473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2179  -11.4247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5093  -11.0194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9291  -12.6548    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.6361  -12.2451    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3428  -12.6582    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0478  -12.2520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0507  -11.4344    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.3425  -11.0248    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6314  -11.4327    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7593  -11.0274    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   19.4661  -11.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3455  -10.3139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.1627  -10.3139    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.4595  -12.2548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1654  -12.6649    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8750  -12.2578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8742  -11.4364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1676  -11.0300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.5824  -12.6670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5816  -13.4842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.5068  -10.2022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4990   -9.3812    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
  7  8  1  0
  8  9  1  0
  8 13  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 11 14  1  0
 14 15  1  0
 14 16  2  0
 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  1  0
  6 25  1  0
 25 26  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4250223

   ---

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: 372.45

Molecular Weight (Monoisotopic): 372.1256

AlogP: 2.23

#Rotatable Bonds: 5

Polar Surface Area: 95.32

Molecular Species: NEUTRAL

HBA: 6

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.32

CX LogP: 1.38

CX LogD: 1.38

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.86

Np Likeness Score: -1.88

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