N-((3R,4R)-4-Fluoro-1-(9-isopropyl-6-((3-ethyl-1-methyl-1H-pyrazol-4-yl)amino)-9H-purin-2-yl)pyrrolidin-3-yl)acrylamide

ID: ALA4218154

Chembl Id: CHEMBL4218154

PubChem CID: 118073642

Max Phase: Preclinical

Molecular Formula: C21H28FN9O

Molecular Weight: 441.52

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  C=CC(=O)N[C@@H]1CN(c2nc(Nc3cn(C)nc3CC)c3ncn(C(C)C)c3n2)C[C@H]1F

Standard InChI:  InChI=1S/C21H28FN9O/c1-6-14-16(9-29(5)28-14)25-19-18-20(31(11-23-18)12(3)4)27-21(26-19)30-8-13(22)15(10-30)24-17(32)7-2/h7,9,11-13,15H,2,6,8,10H2,1,3-5H3,(H,24,32)(H,25,26,27)/t13-,15-/m1/s1

Standard InChI Key:  ODFSNABUETZLTN-UKRRQHHQSA-N

Alternative Forms

1. Parent:

   

   ALA4218154

   N-[(3R,4R)-1-[6-[(3-ethyl-1-methylpyrazol-4-yl)amino]-9-propan-2-ylpurin-2-yl]-4-fluoropyrrolidin-3-yl]prop-2-enamide

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: 441.52

Molecular Weight (Monoisotopic): 441.2401

AlogP: 2.28

#Rotatable Bonds: 7

Polar Surface Area: 105.79

Molecular Species: NEUTRAL

HBA: 9

HBD: 2

#RO5 Violations: 0

HBA (Lipinski): 10

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 0

CX Acidic pKa: 11.30

CX Basic pKa: 3.23

CX LogP: 2.71

CX LogD: 2.71

Aromatic Rings: 3

Heavy Atoms: 32

QED Weighted: 0.54

Np Likeness Score: -1.08

References

1. Planken S, Behenna DC, Nair SK, Johnson TO, Nagata A, Almaden C, Bailey S, Ballard TE, Bernier L, Cheng H, Cho-Schultz S, Dalvie D, Deal JG, Dinh DM, Edwards MP, Ferre RA, Gajiwala KS, Hemkens M, Kania RS, Kath JC, Matthews J, Murray BW, Niessen S, Orr ST, Pairish M, Sach NW, Shen H, Shi M, Solowiej J, Tran K, Tseng E, Vicini P, Wang Y, Weinrich SL, Zhou R, Zientek M, Liu L, Luo Y, Xin S, Zhang C, Lafontaine J..  (2017)  Discovery of N-((3R,4R)-4-Fluoro-1-(6-((3-methoxy-1-methyl-1H-pyrazol-4-yl)amino)-9-methyl-9H-purin-2-yl)pyrrolidine-3-yl)acrylamide (PF-06747775) through Structure-Based Drug Design: A High Affinity Irreversible Inhibitor Targeting Oncogenic EGFR Mutants with Selectivity over Wild-Type EGFR.,  60  (7): [PMID:28287730] [10.1021/acs.jmedchem.6b01894]

Source

Source(1):

• Scientific Literature