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ID: ALA2314745
Max Phase: Preclinical
Molecular Formula: C20H23NO4
Molecular Weight: 341.41
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COc1cc2c(cc1OC)C1Cc3ccc(OC)c(O)c3CN1CC2
Standard InChI: InChI=1S/C20H23NO4/c1-23-17-5-4-12-8-16-14-10-19(25-3)18(24-2)9-13(14)6-7-21(16)11-15(12)20(17)22/h4-5,9-10,16,22H,6-8,11H2,1-3H3
Standard InChI Key: DKBYSDUFSXFXMP-UHFFFAOYSA-N
Associated Targets(Human)
Coagulation factor III 225 Activities
Dopamine D1 receptor 9720 Activities
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Dopamine D2 receptor 23596 Activities
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ECa-109 cell line 1254 Activities
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Molecule Features
| Natural Product: Yes | 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: 341.41 | Molecular Weight (Monoisotopic): 341.1627 | AlogP: 3.07 | #Rotatable Bonds: 3 |
| Polar Surface Area: 51.16 | Molecular Species: NEUTRAL | HBA: 5 | HBD: 1 |
| #RO5 Violations: 0 | HBA (Lipinski): 5 | HBD (Lipinski): 1 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: 9.23 | CX Basic pKa: 6.28 | CX LogP: 3.00 | CX LogD: 2.96 |
| Aromatic Rings: 2 | Heavy Atoms: 25 | QED Weighted: 0.93 | Np Likeness Score: 0.99 |
References
| 1. Ge HX, Zhang J, Chen L, Kou JP, Yu BY.. (2013) Chemical and microbial semi-synthesis of tetrahydroprotoberberines as inhibitors on tissue factor procoagulant activity., 21 (1): [PMID:23199480] [10.1016/j.bmc.2012.11.002] |
| 2. Ge H, Zhang Y, Yang Z, Qiang K, Chen C, Sun L, Chen M, Zhang J.. (2019) Chemical synthesis, microbial transformation and biological evaluation of tetrahydroprotoberberines as dopamine D1/D2 receptor ligands., 27 (10): [PMID:30981605] [10.1016/j.bmc.2019.04.014] |
| 3. Zeng R, Yang XM, Li HW, Li X, Guan Y, Yu T, Yan P, Yuan W, Niu SL, Gu J, Chen YC, Ouyang Q.. (2023) Simplified Derivatives of Tetrandrine as Potent and Specific P-gp Inhibitors to Reverse Multidrug Resistance in Cancer Chemotherapy., 66 (6): [PMID:36892076] [10.1021/acs.jmedchem.2c02061] |
Source
Source(1):