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ID: ALA3621972
Max Phase: Preclinical
Molecular Formula: C21H27N
Molecular Weight: 293.45
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: C[C@H](CCN1CCCCC1)c1ccc(-c2ccccc2)cc1
Standard InChI: InChI=1S/C21H27N/c1-18(14-17-22-15-6-3-7-16-22)19-10-12-21(13-11-19)20-8-4-2-5-9-20/h2,4-5,8-13,18H,3,6-7,14-17H2,1H3/t18-/m1/s1
Standard InChI Key: BJQAKTZCQPXMQT-GOSISDBHSA-N
Associated Targets(Human)
SH-SY5Y (11521 Activities)
Associated Targets(non-human)
SIGMAR1 Sigma-1 receptor (3326 Activities)
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Tmem97 Sigma intracellular receptor 2 (922 Activities)
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ache Acetylcholinesterase (12221 Activities)
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PC-12 (7051 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: 293.45 | Molecular Weight (Monoisotopic): 293.2143 | AlogP: 5.33 | #Rotatable Bonds: 5 |
| Polar Surface Area: 3.24 | Molecular Species: BASE | HBA: 1 | HBD: 0 |
| #RO5 Violations: 1 | HBA (Lipinski): 1 | HBD (Lipinski): 0 | #RO5 Violations (Lipinski): 1 |
| CX Acidic pKa: | CX Basic pKa: 9.87 | CX LogP: 5.43 | CX LogD: 3.00 |
| Aromatic Rings: 2 | Heavy Atoms: 22 | QED Weighted: 0.72 | Np Likeness Score: -0.70 |
References
| 1. Rossi D, Marra A, Rui M, Laurini E, Fermeglia M, Pricl S, Schepmann D, Wuensch B, Peviani M, Curti D, Collina S. (2015) A step forward in the sigma enigma: a role for chirality in the sigma1 receptorligand interaction?, 6 (1): [10.1039/C4MD00349G] |
| 2. Rui M, Rossino G, Coniglio S, Monteleone S, Scuteri A, Malacrida A, Rossi D, Catenacci L, Sorrenti M, Paolillo M, Curti D, Venturini L, Schepmann D, Wünsch B, Liedl KR, Cavaletti G, Pace V, Urban E, Collina S.. (2018) Identification of dual Sigma1 receptor modulators/acetylcholinesterase inhibitors with antioxidant and neurotrophic properties, as neuroprotective agents., 158 [PMID:30223122] [10.1016/j.ejmech.2018.09.010] |
| 3. Rossino G, Rui M, Linciano P, Rossi D, Boiocchi M, Peviani M, Poggio E, Curti D, Schepmann D, Wünsch B, González-Avendaño M, Vergara-Jaque A, Caballero J, Collina S.. (2021) Bitopic Sigma 1 Receptor Modulators to Shed Light on Molecular Mechanisms Underpinning Ligand Binding and Receptor Oligomerization., 64 (20.0): [PMID:34624193] [10.1021/acs.jmedchem.1c00886] |
Source
Source(1):