3-(4-amino-7-((1s,3s)-3-(azetidin-1-ylmethyl)cyclobutyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)phenol

ID: ALA3787112

Chembl Id: CHEMBL3787112

PubChem CID: 67035086

Max Phase: Preclinical

Molecular Formula: C20H23N5O

Molecular Weight: 349.44

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  Nc1ncnc2c1c(-c1cccc(O)c1)cn2[C@H]1C[C@@H](CN2CCC2)C1

Standard InChI:  InChI=1S/C20H23N5O/c21-19-18-17(14-3-1-4-16(26)9-14)11-25(20(18)23-12-22-19)15-7-13(8-15)10-24-5-2-6-24/h1,3-4,9,11-13,15,26H,2,5-8,10H2,(H2,21,22,23)/t13-,15+

Standard InChI Key:  BETBNWGUKZUUAX-OTVXOJSOSA-N

Alternative Forms

1. Parent:

   

   ALA3787112

   cis-3-[4-amino-7-(3-azetidin-1-ylmethyl-cyclobutyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-phenol

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: 349.44

Molecular Weight (Monoisotopic): 349.1903

AlogP: 3.04

#Rotatable Bonds: 4

Polar Surface Area: 80.20

Molecular Species: BASE

HBA: 6

HBD: 2

#RO5 Violations: ┄

HBA (Lipinski): 6

HBD (Lipinski): 3

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: 9.89

CX Basic pKa: 9.18

CX LogP: 1.77

CX LogD: 0.36

Aromatic Rings: 3

Heavy Atoms: 26

QED Weighted: 0.76

Np Likeness Score: -0.31

References

1. Stauffer F, Cowan-Jacob SW, Scheufler C, Furet P..  (2016)  Identification of a 5-[3-phenyl-(2-cyclic-ether)-methylether]-4-aminopyrrolo[2,3-d]pyrimidine series of IGF-1R inhibitors.,  26  (8): [PMID:26951750] [10.1016/j.bmcl.2016.02.074]

2. 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]

3. Talele TT..  (2018)  Natural-Products-Inspired Use of the gem-Dimethyl Group in Medicinal Chemistry.,  61  (6): [PMID:28850227] [10.1021/acs.jmedchem.7b00315]

Source

Source(1):

• Scientific Literature