(3R,3'R)-3-((3-chloro-5-fluorophenyl)amino)-1'-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)-[1,3'-bipiperidin]-2-one

ID: ALA5169765

Chembl Id: CHEMBL5169765

PubChem CID: 67971632

Max Phase: Preclinical

Molecular Formula: C22H24ClFN6O

Molecular Weight: 442.93

Names and Identifiers

Canonical SMILES:  O=C1[C@H](Nc2cc(F)cc(Cl)c2)CCCN1[C@@H]1CCCN(c2ncnc3[nH]ccc23)C1

Standard InChI:  InChI=1S/C22H24ClFN6O/c23-14-9-15(24)11-16(10-14)28-19-4-2-8-30(22(19)31)17-3-1-7-29(12-17)21-18-5-6-25-20(18)26-13-27-21/h5-6,9-11,13,17,19,28H,1-4,7-8,12H2,(H,25,26,27)/t17-,19-/m1/s1

Standard InChI Key:  OVBRVYHGBQUXHR-IEBWSBKVSA-N

Alternative Forms

1. Parent:

   

   ALA5169765

   (3R)-3-(3-chloro-5-fluoroanilino)-1-[(3R)-1-(7H-pyrrolo[2,3-d]pyrimidin-4-yl)piperidin-3-yl]piperidin-2-one

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type:

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 442.93

Molecular Weight (Monoisotopic): 442.1684

AlogP: 3.82

#Rotatable Bonds: 4

Polar Surface Area: 77.15

Molecular Species: NEUTRAL

HBA: 5

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 7

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 13.56

CX Basic pKa: 6.44

CX LogP: 3.44

CX LogD: 3.40

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.64

Np Likeness Score: -1.26

References

1. Hopkins BT, Bame E, Bell N, Bohnert T, Bowden-Verhoek JK, Bui M, Cancilla MT, Conlon P, Cullen P, Erlanson DA, Fan J, Fuchs-Knotts T, Hansen S, Heumann S, Jenkins TJ, Gua C, Liu Y, Liu Y, Lulla M, Marcotte D, Marx I, McDowell B, Mertsching E, Negrou E, Romanowski MJ, Scott D, Silvian L, Yang W, Zhong M..  (2021)  Utilizing structure based drug design and metabolic soft spot identification to optimize the in vitro potency and in vivo pharmacokinetic properties leading to the discovery of novel reversible Bruton's tyrosine kinase inhibitors.,  44  [PMID:34314938] [10.1016/j.bmc.2021.116275]

Source

Source(1):

• Scientific Literature