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ID: ALA87381
Max Phase: Preclinical
Molecular Formula: C21H26N2O
Molecular Weight: 322.45
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: Nc1cccc2c1C[C@@H](N1CCC(c3ccccc3)CC1)[C@H](O)C2
Standard InChI: InChI=1S/C21H26N2O/c22-19-8-4-7-17-13-21(24)20(14-18(17)19)23-11-9-16(10-12-23)15-5-2-1-3-6-15/h1-8,16,20-21,24H,9-14,22H2/t20-,21-/m1/s1
Standard InChI Key: CELYMPNBUOGKMD-NHCUHLMSSA-N
Associated Targets(non-human)
Vesicular acetylcholine transporter 105 Activities
Vesicular acetylcholine transporter 102 Activities
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Sigma opioid receptor 1607 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: 322.45 | Molecular Weight (Monoisotopic): 322.2045 | AlogP: 2.98 | #Rotatable Bonds: 2 |
| Polar Surface Area: 49.49 | Molecular Species: BASE | HBA: 3 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 3 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: 9.75 | CX LogP: 3.11 | CX LogD: 0.79 |
| Aromatic Rings: 2 | Heavy Atoms: 24 | QED Weighted: 0.84 | Np Likeness Score: 0.40 |
References
| 1. Efange SM, Khare AB, Foulon C, Akella SK, Parsons SM.. (1994) Spirovesamicols: conformationally restricted analogs of 2-(4-phenylpiperidino)cyclohexanol (vesamicol, AH5183) as potential modulators of presynaptic cholinergic function., 37 (16): [PMID:8057300] [10.1021/jm00042a010] |
| 2. Barthel C, Sorger D, Deuther-Conrad W, Scheunemann M, Schweiger S, Jäckel P, Roghani A, Steinbach J, Schüürmann G, Sabri O, Brust P, Wenzel B.. (2015) New systematically modified vesamicol analogs and their affinity and selectivity for the vesicular acetylcholine transporter - A critical examination of the lead structure., 100 [PMID:26071858] [10.1016/j.ejmech.2015.05.033] |
Source
Source(1):