6-(1-(4-methoxyphenylsulfonyl)azepan-4-ylamino)nicotinonitrile

ID: ALA4251289

PubChem CID: 145984602

Max Phase: Preclinical

Molecular Formula: C19H22N4O3S

Molecular Weight: 386.48

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  COc1ccc(S(=O)(=O)N2CCCC(Nc3ccc(C#N)cn3)CC2)cc1

Standard InChI:  InChI=1S/C19H22N4O3S/c1-26-17-5-7-18(8-6-17)27(24,25)23-11-2-3-16(10-12-23)22-19-9-4-15(13-20)14-21-19/h4-9,14,16H,2-3,10-12H2,1H3,(H,21,22)

Standard InChI Key:  NWRQZKFLYJKOLM-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 27 29  0  0  0  0  0  0  0  0999 V2000
   13.3130   -6.7810    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3119   -7.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0199   -8.0095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   14.7296   -7.6001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.7268   -6.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0181   -6.3721    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.4379   -8.0075    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   16.1450   -7.5978    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0825   -6.7872    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.6809   -6.2278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.8217   -8.0578    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4886   -6.3433    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6029   -7.8135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8968   -7.0500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.1928   -5.9267    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
   18.9048   -6.3278    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7801   -5.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.5973   -5.2168    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.9086   -7.1453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6198   -7.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3241   -7.1301    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3128   -6.3088    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6011   -5.9115    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0367   -7.5302    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.6052   -6.3726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.8947   -5.9638    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   21.7394   -7.1132    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
  9 10  1  0
  8 11  1  0
 10 12  1  0
 11 13  1  0
 12 14  1  0
 13 14  1  0
 12 15  1  0
 15 16  1  0
 15 17  2  0
 15 18  2  0
 16 19  2  0
 19 20  1  0
 20 21  2  0
 21 22  1  0
 22 23  2  0
 23 16  1  0
 21 24  1  0
  1 25  1  0
 25 26  3  0
 24 27  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4251289

   ---

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: 386.48

Molecular Weight (Monoisotopic): 386.1413

AlogP: 2.62

#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: 2.70

CX LogP: 1.90

CX LogD: 1.90

Aromatic Rings: 2

Heavy Atoms: 27

QED Weighted: 0.85

Np Likeness Score: -2.21

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