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ID: ALA4074659
Max Phase: Preclinical
Molecular Formula: C20H25Cl2N3
Molecular Weight: 305.43
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: CNCc1cccc(CCc2ccc3c(C)cc(N)nc3c2)c1.Cl.Cl
Standard InChI: InChI=1S/C20H23N3.2ClH/c1-14-10-20(21)23-19-12-16(8-9-18(14)19)7-6-15-4-3-5-17(11-15)13-22-2;;/h3-5,8-12,22H,6-7,13H2,1-2H3,(H2,21,23);2*1H
Standard InChI Key: OZIBQKYYCZDPRI-UHFFFAOYSA-N
Associated Targets(Human)
NOS1 Tchem Nitric-oxide synthase, brain (1786 Activities)
NOS3 Tchem Nitric-oxide synthase, endothelial (1452 Activities)
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A-375 (9258 Activities)
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HEK293 (82097 Activities)
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HepG2 (196354 Activities)
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Associated Targets(non-human)
Nos1 Nitric-oxide synthase, brain (2987 Activities)
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Nos2 Nitric oxide synthase, inducible (3573 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: 305.43 | Molecular Weight (Monoisotopic): 305.1892 | AlogP: 3.63 | #Rotatable Bonds: 5 |
| Polar Surface Area: 50.94 | 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: 9.43 | CX LogP: 4.50 | CX LogD: 2.27 |
| Aromatic Rings: 3 | Heavy Atoms: 23 | QED Weighted: 0.76 | Np Likeness Score: -0.15 |
References
| 1. Cinelli MA, Li H, Chreifi G, Poulos TL, Silverman RB.. (2017) Nitrile in the Hole: Discovery of a Small Auxiliary Pocket in Neuronal Nitric Oxide Synthase Leading to the Development of Potent and Selective 2-Aminoquinoline Inhibitors., 60 (9): [PMID:28422508] [10.1021/acs.jmedchem.7b00259] |
| 2. Vasu D, Reidl CT, Wang E, Yang S, Silverman RB.. (2023) Improved synthesis and anticancer activity of a potent neuronal nitric oxide synthase inhibitor., 90 [PMID:37196870] [10.1016/j.bmcl.2023.129329] |
Source
Source(1):