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ID: ALA495592
Max Phase: Preclinical
Molecular Formula: C19H16N2O2
Molecular Weight: 304.35
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: O=C(N[C@@H]1CCc2ccccc21)C(=O)c1c[nH]c2ccccc12
Standard InChI: InChI=1S/C19H16N2O2/c22-18(15-11-20-16-8-4-3-7-14(15)16)19(23)21-17-10-9-12-5-1-2-6-13(12)17/h1-8,11,17,20H,9-10H2,(H,21,23)/t17-/m1/s1
Standard InChI Key: HPOOEGNMALNZJV-QGZVFWFLSA-N
Associated Targets(non-human)
GABA-A receptor; anion channel 910 Activities
GABA-A receptor; alpha-1/beta-2/gamma-2 554 Activities
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GABA A receptor alpha-3/beta-2/gamma-2 43 Activities
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GABA A receptor alpha-5/beta-3/gamma-2 149 Activities
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GABA receptor alpha-2 subunit 87 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: 304.35 | Molecular Weight (Monoisotopic): 304.1212 | AlogP: 3.15 | #Rotatable Bonds: 3 |
| Polar Surface Area: 61.96 | Molecular Species: NEUTRAL | HBA: 2 | HBD: 2 |
| #RO5 Violations: 0 | HBA (Lipinski): 4 | HBD (Lipinski): 2 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 12.02 | CX Basic pKa: | CX LogP: 3.27 | CX LogD: 3.27 |
| Aromatic Rings: 3 | Heavy Atoms: 23 | QED Weighted: 0.58 | Np Likeness Score: -0.48 |
References
| 1. Primofiore G, Settimo FD, Taliani S, Marini AM, Novellino E, Greco G, Lavecchia A, Besnard F, Trincavelli L, Costa B, Martini C.. (2001) Novel N-(arylalkyl)indol-3-ylglyoxylylamides targeted as ligands of the benzodiazepine receptor: synthesis, biological evaluation, and molecular modeling analysis of the structure-activity relationships., 44 (14): [PMID:11428922] [10.1021/jm010827j] |
| 2. Taliani S, Cosimelli B, Da Settimo F, Marini AM, La Motta C, Simorini F, Salerno S, Novellino E, Greco G, Cosconati S, Marinelli L, Salvetti F, L'Abbate G, Trasciatti S, Montali M, Costa B, Martini C.. (2009) Identification of anxiolytic/nonsedative agents among indol-3-ylglyoxylamides acting as functionally selective agonists at the gamma-aminobutyric acid-A (GABAA) alpha2 benzodiazepine receptor., 52 (12): [PMID:19469479] [10.1021/jm9001154] |
Source
Source(1):