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ID: ALA2007996
Max Phase: Preclinical
Molecular Formula: C17H17ClN2
Molecular Weight: 284.79
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CC1=C[C@@H]2Cc3nc4cc(Cl)ccc4c(N)c3[C@H](C1)C2
Standard InChI: InChI=1S/C17H17ClN2/c1-9-4-10-6-11(5-9)16-15(7-10)20-14-8-12(18)2-3-13(14)17(16)19/h2-4,8,10-11H,5-7H2,1H3,(H2,19,20)/t10-,11+/m0/s1
Standard InChI Key: UKCBMHDZLYYTMI-WDEREUQCSA-N
Associated Targets(Human)
ACHE Tclin Acetylcholinesterase (18204 Activities)
BCHE Tclin Butyrylcholinesterase (7174 Activities)
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BACE1 Tchem Beta-secretase 1 (15641 Activities)
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APP Tclin Amyloid-beta A4 protein (8510 Activities)
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EPHX2 Tchem Epoxide hydratase (3844 Activities)
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Associated Targets(non-human)
ACHE Acetylcholinesterase (1035 Activities)
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Ephx2 Epoxide hydratase (467 Activities)
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Ache Acetylcholinesterase (1323 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: 284.79 | Molecular Weight (Monoisotopic): 284.1080 | AlogP: 4.47 | #Rotatable Bonds: 0 |
| Polar Surface Area: 38.91 | Molecular Species: NEUTRAL | HBA: 2 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 2 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: 8.07 | CX LogP: 3.67 | CX LogD: 2.95 |
| Aromatic Rings: 2 | Heavy Atoms: 20 | QED Weighted: 0.73 | Np Likeness Score: 0.03 |
References
| 1. Camps P, Gómez E, Muñoz-Torrero D, Badia A, Clos MV, Curutchet C, Muñoz-Muriedas J, Luque FJ.. (2006) Binding of 13-amidohuprines to acetylcholinesterase: exploring the ligand-induced conformational change of the gly117-gly118 peptide bond in the oxyanion hole., 49 (23): [PMID:17154513] [10.1021/jm060945c] |
| 2. Viayna E, Sola I, Bartolini M, De Simone A, Tapia-Rojas C, Serrano FG, Sabaté R, Juárez-Jiménez J, Pérez B, Luque FJ, Andrisano V, Clos MV, Inestrosa NC, Muñoz-Torrero D.. (2014) Synthesis and multitarget biological profiling of a novel family of rhein derivatives as disease-modifying anti-Alzheimer agents., 57 (6): [PMID:24568372] [10.1021/jm401824w] |
| 3. Codony S, Pont C, Griñán-Ferré C, Di Pede-Mattatelli A, Calvó-Tusell C, Feixas F, Osuna S, Jarné-Ferrer J, Naldi M, Bartolini M, Loza MI, Brea J, Pérez B, Bartra C, Sanfeliu C, Juárez-Jiménez J, Morisseau C, Hammock BD, Pallàs M, Vázquez S, Muñoz-Torrero D.. (2022) Discovery and In Vivo Proof of Concept of a Highly Potent Dual Inhibitor of Soluble Epoxide Hydrolase and Acetylcholinesterase for the Treatment of Alzheimer's Disease., 65 (6.0): [PMID:35271276] [10.1021/acs.jmedchem.1c02150] |
Source
Source(1):