ID: ALA3608432

Max Phase: Preclinical

Molecular Formula: C20H26FN9O

Molecular Weight: 427.49

Molecule Type: Small molecule

Representations

Canonical SMILES:  C=CC(=O)N[C@@H]1CN(c2nc(Nc3cn(C)nc3C)c3ncn(C(C)C)c3n2)C[C@H]1F

Standard InChI:  InChI=1S/C20H26FN9O/c1-6-16(31)23-15-9-29(7-13(15)21)20-25-18(24-14-8-28(5)27-12(14)4)17-19(26-20)30(10-22-17)11(2)3/h6,8,10-11,13,15H,1,7,9H2,2-5H3,(H,23,31)(H,24,25,26)/t13-,15-/m1/s1

Standard InChI Key:  HLSFKKBVOPHVAO-UKRRQHHQSA-N

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

Properties

Molecular Weight: 427.49

Molecular Weight (Monoisotopic): 427.2244

AlogP: 2.02

#Rotatable Bonds: 6

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: 11.34

CX Basic pKa: 3.26

CX LogP: 2.01

CX LogD: 2.01

Aromatic Rings: 3

Heavy Atoms: 31

QED Weighted: 0.58

Np Likeness Score: -1.15

References

1. Abdel-Magid AF..  (2015)  Inhibitors of the Epidermal Growth Factor Receptor (EGFR) May Provide Effective Treatment for Lung Adenocarcinoma.,  6  (7): [PMID:26191356] [10.1021/acsmedchemlett.5b00231]

2. 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