6-(1-(4-hydroxyphenylsulfonyl)pyrrolidin-3-ylamino)nicotinonitrile

ID: ALA4250825

PubChem CID: 145986287

Max Phase: Preclinical

Molecular Formula: C16H16N4O3S

Molecular Weight: 344.40

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#Cc1ccc(NC2CCN(S(=O)(=O)c3ccc(O)cc3)C2)nc1

Standard InChI:  InChI=1S/C16H16N4O3S/c17-9-12-1-6-16(18-10-12)19-13-7-8-20(11-13)24(22,23)15-4-2-14(21)3-5-15/h1-6,10,13,21H,7-8,11H2,(H,18,19)

Standard InChI Key:  GWEZTMRSBKWZRQ-UHFFFAOYSA-N

Molfile:  

     RDKit          2D

 24 26  0  0  0  0  0  0  0  0999 V2000
    3.2219   -6.5334    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2208   -7.3529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9288   -7.7619    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.6385   -7.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6357   -6.5298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9271   -6.1245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3469   -7.7599    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0544   -7.3498    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8383   -7.5831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3055   -6.9126    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.8121   -6.2611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0401   -6.5291    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1225   -6.8965    0.0000 S   0  0  0  0  0  0  0  0  0  0  0  0
    8.5170   -6.1808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3329   -6.1699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.7273   -5.4551    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3047   -4.7546    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4835   -4.7735    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0928   -5.4889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5269   -7.5982    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.9396   -6.8925    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5141   -6.1249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8036   -5.7162    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.6983   -4.0385    0.0000 O   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
 10 11  1  0
 11 12  1  0
 12  8  1  0
 10 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 14  1  0
 13 20  2  0
 13 21  2  0
  1 22  1  0
 22 23  3  0
 17 24  1  0
M  END

Alternative Forms

1. Parent:

   

   ALA4250825

   ---

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: 344.40

Molecular Weight (Monoisotopic): 344.0943

AlogP: 1.53

#Rotatable Bonds: 4

Polar Surface Area: 106.32

Molecular Species: NEUTRAL

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 8.29

CX Basic pKa: 2.69

CX LogP: 1.18

CX LogD: 1.13

Aromatic Rings: 2

Heavy Atoms: 24

QED Weighted: 0.87

Np Likeness Score: -2.11

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