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ID: ALA3787112
Max Phase: Preclinical
Molecular Formula: C20H23N5O
Molecular Weight: 349.44
Molecule Type: Small molecule
Associated Items:
Representations
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
Associated Targets(Human)
PIK3CD Tclin PI3-kinase p110-delta subunit (6699 Activities)
PI4KB Tchem PI4-kinase beta subunit (1593 Activities)
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PKN2 Tchem Protein kinase N2 (1991 Activities)
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PKN1 Tchem Protein kinase N1 (787 Activities)
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PRKACA Tchem cAMP-dependent protein kinase alpha-catalytic subunit (3475 Activities)
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PRKCA Tchem Protein kinase C alpha (5923 Activities)
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PRKCQ Tchem Protein kinase C theta (3319 Activities)
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RET Tclin Tyrosine-protein kinase receptor RET (6732 Activities)
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ROCK2 Tclin Rho-associated protein kinase 2 (6206 Activities)
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SYK Tclin Tyrosine-protein kinase SYK (7372 Activities)
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TYK2 Tclin Tyrosine-protein kinase TYK2 (5029 Activities)
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PIK3C3 Tchem Phosphatidylinositol 3-kinase catalytic subunit type 3 (535 Activities)
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IGF1R Tclin Insulin-like growth factor I receptor (8605 Activities)
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INSR Tclin Insulin receptor (5558 Activities)
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EPHB4 Tchem Ephrin type-B receptor 4 (3198 Activities)
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JAK1 Tclin Tyrosine-protein kinase JAK1 (8569 Activities)
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KDR Tclin Vascular endothelial growth factor receptor 2 (20924 Activities)
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LCK Tclin Tyrosine-protein kinase LCK (9212 Activities)
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EGFR Tclin Epidermal growth factor receptor erbB1 (33727 Activities)
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PIK3CB Tchem PI3-kinase p110-beta subunit (4044 Activities)
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PIK3CA Tclin PI3-kinase p110-alpha subunit (12269 Activities)
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KCNH2 Tclin HERG (29587 Activities)
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Liver microsome (8277 Activities)
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ALK Tclin ALK tyrosine kinase receptor (7132 Activities)
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ABL1 Tclin Tyrosine-protein kinase ABL (18331 Activities)
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AKT1 Tchem Serine/threonine-protein kinase AKT (9192 Activities)
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AURKA Tchem Serine/threonine-protein kinase Aurora-A (10240 Activities)
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BTK Tclin Tyrosine-protein kinase BTK (8973 Activities)
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CDK2 Tchem Cyclin-dependent kinase 2 (9050 Activities)
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CDK4 Tclin Cyclin-dependent kinase 4/cyclin D1 (2340 Activities)
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EPHA4 Tchem Ephrin type-A receptor 4 (2022 Activities)
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FGFR3 Tclin Fibroblast growth factor receptor 3 (7811 Activities)
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FGFR4 Tclin Fibroblast growth factor receptor 4 (3668 Activities)
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GSK3B Tclin Glycogen synthase kinase-3 beta (11785 Activities)
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JAK2 Tclin Tyrosine-protein kinase JAK2 (12915 Activities)
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JAK3 Tclin Tyrosine-protein kinase JAK3 (8349 Activities)
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KIT Tclin Stem cell growth factor receptor (10667 Activities)
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MAP3K8 Tchem Mitogen-activated protein kinase kinase kinase 8 (459 Activities)
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MAPK14 Tchem MAP kinase p38 alpha (12866 Activities)
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MAPK1 Tchem MAP kinase ERK2 (25055 Activities)
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MAPKAPK2 Tchem MAP kinase-activated protein kinase 2 (4814 Activities)
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MAPKAPK5 Tchem MAP kinase-activated protein kinase 5 (2831 Activities)
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MET Tclin Hepatocyte growth factor receptor (10718 Activities)
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MKNK2 Tchem MAP kinase signal-integrating kinase 2 (3518 Activities)
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PDGFRA Tclin Platelet-derived growth factor receptor alpha (5682 Activities)
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PDPK1 Tchem 3-phosphoinositide dependent protein kinase-1 (3758 Activities)
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PIK3CG Tclin PI3-kinase p110-gamma subunit (5411 Activities)
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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 |
Drug Indications
| MESH ID | MESH Heading | EFO IDs | EFO Terms | Max Phase for Indication | References |
|---|
Mechanisms of Action
| Mechanism of Action | Action Type | target ID | Target Name | Target Type | Target Organism | Binding Site Name | References |
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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: 0 | HBA (Lipinski): 6 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): 0 |
| 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):