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ID: ALA3973588
Max Phase: Preclinical
Molecular Formula: C19H19N5O3
Molecular Weight: 365.39
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CC(C)Oc1cc(NC(=O)N2CCCc3ccc(C=O)nc32)ncc1C#N
Standard InChI: InChI=1S/C19H19N5O3/c1-12(2)27-16-8-17(21-10-14(16)9-20)23-19(26)24-7-3-4-13-5-6-15(11-25)22-18(13)24/h5-6,8,10-12H,3-4,7H2,1-2H3,(H,21,23,26)
Standard InChI Key: KYVKVDHCJPYHLM-UHFFFAOYSA-N
Associated Targets(Human)
FGFR4 Tclin Fibroblast growth factor receptor 4 (3668 Activities)
FGFR1 Tclin Fibroblast growth factor receptor 1 (9149 Activities)
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FGFR2 Tclin Fibroblast growth factor receptor 2 (3405 Activities)
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FGFR3 Tclin Fibroblast growth factor receptor 3 (7811 Activities)
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Associated Targets(non-human)
Fgfr4 Fibroblast growth factor receptor 4 (138 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 |
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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: 365.39 | Molecular Weight (Monoisotopic): 365.1488 | AlogP: 2.93 | #Rotatable Bonds: 4 |
| Polar Surface Area: 108.21 | Molecular Species: NEUTRAL | HBA: 6 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 8 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 10.87 | CX Basic pKa: 2.36 | CX LogP: 3.08 | CX LogD: 3.08 |
| Aromatic Rings: 2 | Heavy Atoms: 27 | QED Weighted: 0.83 | Np Likeness Score: -1.33 |
References
| 1. (2016) Ring-fused bicyclic pyridyl derivatives as FGFR4 inhibitors, |
| 2. Knoepfel T, Furet P, Mah R, Buschmann N, Leblanc C, Ripoche S, Graus-Porta D, Wartmann M, Galuba I, Fairhurst RA.. (2018) 2-Formylpyridyl Ureas as Highly Selective Reversible-Covalent Inhibitors of Fibroblast Growth Factor Receptor 4., 9 (3): [PMID:29541363] [10.1021/acsmedchemlett.7b00485] |
| 3. Fairhurst RA,Knoepfel T,Buschmann N,Leblanc C,Mah R,Todorov M,Nimsgern P,Ripoche S,Niklaus M,Warin N,Luu VH,Madoerin M,Wirth J,Graus-Porta D,Weiss A,Kiffe M,Wartmann M,Kinyamu-Akunda J,Sterker D,Stamm C,Adler F,Buhles A,Schadt H,Couttet P,Blank J,Galuba I,Trappe J,Voshol J,Ostermann N,Zou C,Berghausen J,Del Rio Espinola A,Jahnke W,Furet P. (2020) Discovery of Roblitinib (FGF401) as a Reversible-Covalent Inhibitor of the Kinase Activity of Fibroblast Growth Factor Receptor 4., 63 (21.0): [PMID:32930584] [10.1021/acs.jmedchem.0c01019] |
| 4. Zhang Z, Wang Y, Chen X, Song X, Tu Z, Chen Y, Zhang Z, Ding K.. (2021) Characterization of an aromatic trifluoromethyl ketone as a new warhead for covalently reversible kinase inhibitor design., 50 [PMID:34670167] [10.1016/j.bmc.2021.116457] |
Source
Source(2):