1-(4-((cis)-3-(4-amino-5-(2-fluoro-5-(((S)-tetrahydrofuran-2-yl)methoxy)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-7-yl)cyclobutyl)piperazin-1-yl)ethanone

ID: ALA3785951

Chembl Id: CHEMBL3785951

PubChem CID: 68293638

Max Phase: Preclinical

Molecular Formula: C27H33FN6O3

Molecular Weight: 508.60

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CC(=O)N1CCN([C@H]2C[C@@H](n3cc(-c4cc(OC[C@@H]5CCCO5)ccc4F)c4c(N)ncnc43)C2)CC1

Standard InChI:  InChI=1S/C27H33FN6O3/c1-17(35)32-6-8-33(9-7-32)18-11-19(12-18)34-14-23(25-26(29)30-16-31-27(25)34)22-13-20(4-5-24(22)28)37-15-21-3-2-10-36-21/h4-5,13-14,16,18-19,21H,2-3,6-12,15H2,1H3,(H2,29,30,31)/t18-,19+,21-/m0/s1

Standard InChI Key:  YXLQJZQRBVGUCM-ZVDOUQERSA-N

Alternative Forms

1. Parent:

   

   ALA3785951

   1-{4-[cis-3-(4-Amino-5-{2-fluoro-5-[(S)-1-(tetrahydro-furan-2-yl)methoxy]-phenyl}-pyrrolo[2,3-d]pyrimidin-7-yl)-cyclobutyl]-piperazin-1-yl}-ethanone

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: 508.60

Molecular Weight (Monoisotopic): 508.2598

AlogP: 3.25

#Rotatable Bonds: 6

Polar Surface Area: 98.74

Molecular Species: NEUTRAL

HBA: 8

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 9

HBD (Lipinski): 2

#RO5 Violations (Lipinski): 1

CX Acidic pKa: ┄

CX Basic pKa: 7.76

CX LogP: 1.72

CX LogD: 1.18

Aromatic Rings: 3

Heavy Atoms: 37

QED Weighted: 0.55

Np Likeness Score: -0.70

References

1. Fairhurst RA, Marsilje TH, Stutz S, Boos A, Niklaus M, Chen B, Jiang S, Lu W, Furet P, McCarthy C, Stauffer F, Guagnano V, Vaupel A, Michellys PY, Schnell C, Jeay S..  (2016)  Optimisation of a 5-[3-phenyl-(2-cyclic-ether)-methyl-ether]-4-aminopyrrolopyrimidine series of IGF-1R inhibitors.,  26  (8): [PMID:26951753] [10.1016/j.bmcl.2016.02.075]

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