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ID: ALA69064
Max Phase: Preclinical
Molecular Formula: C22H23NO2
Molecular Weight: 333.43
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: O=C(O)[C@@H]1CCCN(CCC=C2c3ccccc3-c3ccccc32)C1
Standard InChI: InChI=1S/C22H23NO2/c24-22(25)16-7-5-13-23(15-16)14-6-12-21-19-10-3-1-8-17(19)18-9-2-4-11-20(18)21/h1-4,8-12,16H,5-7,13-15H2,(H,24,25)/t16-/m1/s1
Standard InChI Key: SJJUKGVRGZOKFH-MRXNPFEDSA-N
Associated Targets(non-human)
GABA transporter 97 Activities
GABA transporter 1 233 Activities
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GABA transporter 1 1980 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: 333.43 | Molecular Weight (Monoisotopic): 333.1729 | AlogP: 4.29 | #Rotatable Bonds: 4 |
| Polar Surface Area: 40.54 | Molecular Species: ZWITTERION | HBA: 2 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 3 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 3.65 | CX Basic pKa: 9.95 | CX LogP: 1.42 | CX LogD: 1.42 |
| Aromatic Rings: 2 | Heavy Atoms: 25 | QED Weighted: 0.77 | Np Likeness Score: -0.36 |
References
| 1. Andersen KE, Sørensen JL, Lau J, Lundt BF, Petersen H, Huusfeldt PO, Suzdak PD, Swedberg MD.. (2001) Synthesis of novel gamma-aminobutyric acid (GABA) uptake inhibitors. 5.(1) Preparation and structure-activity studies of tricyclic analogues of known GABA uptake inhibitors., 44 (13): [PMID:11405652] [10.1021/jm990513k] |
| 2. Jurik A, Zdrazil B, Holy M, Stockner T, Sitte HH, Ecker GF.. (2015) A binding mode hypothesis of tiagabine confirms liothyronine effect on γ-aminobutyric acid transporter 1 (GAT1)., 58 (5): [PMID:25679268] [10.1021/jm5015428] |
| 3. Zaręba P, Sałat K, Höfner GC, Łątka K, Bajda M, Latacz G, Kotniewicz K, Rapacz A, Podkowa A, Maj M, Jóźwiak K, Filipek B, Wanner KT, Malawska B, Kulig K.. (2021) Development of tricyclic N-benzyl-4-hydroxybutanamide derivatives as inhibitors of GABA transporters mGAT1-4 with anticonvulsant, antinociceptive, and antidepressant activity., 221 [PMID:34015586] [10.1016/j.ejmech.2021.113512] |
Source
Source(1):