(R)-1-(3-(4-Amino-3-(3-chloro-4-(pyridin-2-ylmethoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one

ID: ALA4068839

Chembl Id: CHEMBL4068839

PubChem CID: 127264586

Max Phase: Preclinical

Molecular Formula: C25H24ClN7O2

Molecular Weight: 489.97

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)N1CCC[C@@H](n2nc(-c3ccc(OCc4ccccn4)c(Cl)c3)c3c(N)ncnc32)C1

Standard InChI:  InChI=1S/C25H24ClN7O2/c1-2-21(34)32-11-5-7-18(13-32)33-25-22(24(27)29-15-30-25)23(31-33)16-8-9-20(19(26)12-16)35-14-17-6-3-4-10-28-17/h2-4,6,8-10,12,15,18H,1,5,7,11,13-14H2,(H2,27,29,30)/t18-/m1/s1

Standard InChI Key:  RVCKMZIQUFKZFD-GOSISDBHSA-N

Alternative Forms

1. Parent:

   

   ALA4068839

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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: 489.97

Molecular Weight (Monoisotopic): 489.1680

AlogP: 4.05

#Rotatable Bonds: 6

Polar Surface Area: 112.05

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: 4.24

CX LogP: 3.16

CX LogD: 3.16

Aromatic Rings: 4

Heavy Atoms: 35

QED Weighted: 0.41

Np Likeness Score: -1.35

References

1. Wang A, Li X, Wu H, Zou F, Yan XE, Chen C, Hu C, Yu K, Wang W, Zhao P, Wu J, Qi Z, Wang W, Wang B, Wang L, Ren T, Zhang S, Yun CH, Liu J, Liu Q..  (2017)  Discovery of (R)-1-(3-(4-Amino-3-(3-chloro-4-(pyridin-2-ylmethoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)piperidin-1-yl)prop-2-en-1-one (CHMFL-EGFR-202) as a Novel Irreversible EGFR Mutant Kinase Inhibitor with a Distinct Binding Mode.,  60  (7): [PMID:28282122] [10.1021/acs.jmedchem.6b01907]

2. Chen X, Huang Y, Xu W, Cai Y, Yang Y..  (2022)  4-Aminopyrazolopyrimidine scaffold and its deformation in the design of tyrosine and serine/threonine kinase inhibitors in medicinal chemistry.,  13  (9.0): [PMID:36324498] [10.1039/d2md00139j]

Source

Source(1):

• Scientific Literature