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ID: ALA2397256
Max Phase: Preclinical
Molecular Formula: C25H24ClNO4
Molecular Weight: 437.92
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COc1ccc(OCC2c3ccc(OC)cc3CCN2C(=O)c2cccc(Cl)c2)cc1
Standard InChI: InChI=1S/C25H24ClNO4/c1-29-20-6-8-21(9-7-20)31-16-24-23-11-10-22(30-2)15-17(23)12-13-27(24)25(28)18-4-3-5-19(26)14-18/h3-11,14-15,24H,12-13,16H2,1-2H3
Standard InChI Key: WXYIEYRLRWZLSM-UHFFFAOYSA-N
Associated Targets(non-human)
Glutamate receptor ionotropic, AMPA 1 398 Activities
Ionotropic glutamate receptor NMDA 1/2D 870 Activities
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Glutamate NMDA receptor; Grin1/Grin2c 1127 Activities
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Glutamate NMDA receptor; Grin1/Grin2b 1028 Activities
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Glutamate NMDA receptor; Grin1/Grin2a 798 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: 437.92 | Molecular Weight (Monoisotopic): 437.1394 | AlogP: 5.18 | #Rotatable Bonds: 6 |
| Polar Surface Area: 48.00 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 0 |
| #RO5 Violations: 1 | HBA (Lipinski): 5 | HBD (Lipinski): 0 | #RO5 Violations (Lipinski): 1 |
| CX Acidic pKa: | CX Basic pKa: | CX LogP: 5.03 | CX LogD: 5.03 |
| Aromatic Rings: 3 | Heavy Atoms: 31 | QED Weighted: 0.53 | Np Likeness Score: -0.79 |
References
| 1. Santangelo Freel RM, Ogden KK, Strong KL, Khatri A, Chepiga KM, Jensen HS, Traynelis SF, Liotta DC.. (2013) Synthesis and structure activity relationship of tetrahydroisoquinoline-based potentiators of GluN2C and GluN2D containing N-methyl-D-aspartate receptors., 56 (13): [PMID:23627311] [10.1021/jm400177t] |
| 2. Strong KL, Epplin MP, Bacsa J, Butch CJ, Burger PB, Menaldino DS, Traynelis SF, Liotta DC.. (2017) The Structure-Activity Relationship of a Tetrahydroisoquinoline Class of N-Methyl-d-Aspartate Receptor Modulators that Potentiates GluN2B-Containing N-Methyl-d-Aspartate Receptors., 60 (13): [PMID:28586221] [10.1021/acs.jmedchem.7b00239] |
| 3. Epplin MP, Mohan A, Harris LD, Zhu Z, Strong KL, Bacsa J, Le P, Menaldino DS, Traynelis SF, Liotta DC.. (2020) Discovery of Dihydropyrrolo[1,2-a]pyrazin-3(4H)-one-Based Second-Generation GluN2C- and GluN2D-Selective Positive Allosteric Modulators (PAMs) of the N-Methyl-d-Aspartate (NMDA) Receptor., 63 (14): [PMID:32538088] [10.1021/acs.jmedchem.9b01733] |
Source
Source(1):