6-(1-(4-methoxyphenylsulfonyl)piperidin-4-ylamino)picolinonitrile

ID: ALA4246994

PubChem CID: 145984552

Max Phase: Preclinical

Molecular Formula: C18H20N4O3S

Molecular Weight: 372.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)N2CCC(Nc3cccc(C#N)n3)CC2)cc1

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

Standard InChI Key:  WQILLQJVWYIMHZ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 26 28  0  0  0  0  0  0  0  0999 V2000
    2.6895  -10.1612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6884  -10.9807    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3964  -11.3897    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.1061  -10.9803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1033  -10.1576    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3946   -9.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8144  -11.3877    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.5215  -10.9780    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2282  -11.3911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9332  -10.9849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9361  -10.1674    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.2279   -9.7577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5168  -10.1656    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6447   -9.7604    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.3515  -10.1705    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2309   -9.0469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.0481   -9.0469    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.3448  -10.9877    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0508  -11.3978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7604  -10.9907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7596  -10.1693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0530   -9.7629    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.4677  -11.4000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4670  -12.2171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9804  -11.3888    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2671  -11.7915    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
  2 25  1  0
 25 26  3  0
M  END

Alternative Forms

1. Parent:

   

   ALA4246994

   ---

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: 2.51

CX LogP: 1.77

CX LogD: 1.77

Aromatic Rings: 2

Heavy Atoms: 26

QED Weighted: 0.86

Np Likeness Score: -1.84

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