6-(1-tosylpiperidin-4-ylamino)nicotinonitrile

ID: ALA4245957

PubChem CID: 26042546

Max Phase: Preclinical

Molecular Formula: C18H20N4O2S

Molecular Weight: 356.45

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Cc1ccc(S(=O)(=O)N2CCC(Nc3ccc(C#N)cn3)CC2)cc1

Standard InChI:  InChI=1S/C18H20N4O2S/c1-14-2-5-17(6-3-14)25(23,24)22-10-8-16(9-11-22)21-18-7-4-15(12-19)13-20-18/h2-7,13,16H,8-11H2,1H3,(H,20,21)

Standard InChI Key:  IQFPTDKQZKIGSD-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 25 27  0  0  0  0  0  0  0  0999 V2000
    2.1324   -2.5093    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1312   -3.3289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8393   -3.7378    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.5489   -3.3284    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5461   -2.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375   -2.1005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2573   -3.7359    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.9643   -3.3262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6710   -3.7393    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3760   -3.3330    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3789   -2.5155    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.6707   -2.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9596   -2.5137    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0875   -2.1085    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    7.7943   -2.5186    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6737   -1.3950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.4909   -1.3950    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7876   -3.3359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4936   -3.7459    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2032   -3.3389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2024   -2.5174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4958   -2.1110    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4246   -2.1009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7140   -1.6922    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.9106   -3.7481    0.0000 C   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
  1 23  1  0
 23 24  3  0
 20 25  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4245957

   6-[[1-(4-Methylphenyl)sulfonylpiperidin-4-yl]amino]pyridine-3-carbonitrile

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: 356.45

Molecular Weight (Monoisotopic): 356.1307

AlogP: 2.53

#Rotatable Bonds: 4

Polar Surface Area: 86.09

Molecular Species: NEUTRAL

HBA: 5

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 2.70

CX LogP: 2.06

CX LogD: 2.06

Aromatic Rings: 2

Heavy Atoms: 25

QED Weighted: 0.91

Np Likeness Score: -2.31

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