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ID: ALA74448
Max Phase: Preclinical
Molecular Formula: C16H12N4O4
Molecular Weight: 324.30
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: O=C(NNc1ccc([N+](=O)[O-])cc1)C(=O)c1c[nH]c2ccccc12
Standard InChI: InChI=1S/C16H12N4O4/c21-15(13-9-17-14-4-2-1-3-12(13)14)16(22)19-18-10-5-7-11(8-6-10)20(23)24/h1-9,17-18H,(H,19,22)
Standard InChI Key: PBWCWICQJUAIEY-UHFFFAOYSA-N
Associated Targets(non-human)
GABA-A receptor; anion channel 910 Activities
Mus musculus 284745 Activities
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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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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: 324.30 | Molecular Weight (Monoisotopic): 324.0859 | AlogP: 2.40 | #Rotatable Bonds: 5 |
| Polar Surface Area: 117.13 | Molecular Species: NEUTRAL | HBA: 5 | HBD: 3 |
| #RO5 Violations: 0 | HBA (Lipinski): 8 | HBD (Lipinski): 3 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 11.12 | CX Basic pKa: | CX LogP: 2.82 | CX LogD: 2.82 |
| Aromatic Rings: 3 | Heavy Atoms: 24 | QED Weighted: 0.29 | Np Likeness Score: -1.26 |
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. Da Settimo A, Primofiore G, Da Settimo F, Marini AM, Novellino E, Greco G, Gesi M, Martini C, Giannaccini G, Lucacchini A.. (1998) N'-Phenylindol-3-ylglyoxylohydrazide derivatives: synthesis, structure-activity relationships, molecular modeling studies, and pharmacological action on brain benzodiazepine receptors., 41 (20): [PMID:9748357] [10.1021/jm9800301] |
Source
Source(1):