(S)-2-(3-(3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)pyridin-2-ylamino)piperidin-1-ylsulfonyl)acetonitrile

ID: ALA3335691

Chembl Id: CHEMBL3335691

PubChem CID: 58177456

Max Phase: Preclinical

Molecular Formula: C18H19N7O2S

Molecular Weight: 397.46

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  N#CCS(=O)(=O)N1CCC[C@H](Nc2ncccc2-c2cnc3[nH]ccc3n2)C1

Standard InChI:  InChI=1S/C18H19N7O2S/c19-6-10-28(26,27)25-9-2-3-13(12-25)23-17-14(4-1-7-20-17)16-11-22-18-15(24-16)5-8-21-18/h1,4-5,7-8,11,13H,2-3,9-10,12H2,(H,20,23)(H,21,22)/t13-/m0/s1

Standard InChI Key:  PLRGDPPEBDGPBL-ZDUSSCGKSA-N

Alternative Forms

1. Parent:

   

   ALA3335691

   2-[(3S)-3-[[3-(5H-pyrrolo[2,3-b]pyrazin-2-yl)pyridin-2-yl]amino]piperidin-1-yl]sulfonylacetonitrile

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: 397.46

Molecular Weight (Monoisotopic): 397.1321

AlogP: 1.75

#Rotatable Bonds: 5

Polar Surface Area: 127.66

Molecular Species: NEUTRAL

HBA: 7

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 9.29

CX Basic pKa: 5.83

CX LogP: 0.47

CX LogD: 0.45

Aromatic Rings: 3

Heavy Atoms: 28

QED Weighted: 0.67

Np Likeness Score: -1.49

References

1. de Vicente J, Lemoine R, Bartlett M, Hermann JC, Hekmat-Nejad M, Henningsen R, Jin S, Kuglstatter A, Li H, Lovey AJ, Menke J, Niu L, Patel V, Petersen A, Setti L, Shao A, Tivitmahaisoon P, Vu MD, Soth M..  (2014)  Scaffold hopping towards potent and selective JAK3 inhibitors: discovery of novel C-5 substituted pyrrolopyrazines.,  24  (21): [PMID:25262541] [10.1016/j.bmcl.2014.09.031]

2.  (2013)  Inhibitors of JAK, 

Source

Source(2):

• Scientific Literature
• BindingDB Database