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ID: ALA2314732
Max Phase: Preclinical
Molecular Formula: C19H19NO4
Molecular Weight: 325.36
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COc1ccc2c(c1O)CN1CCc3cc4c(cc3[C@@H]1C2)OCO4
Standard InChI: InChI=1S/C19H19NO4/c1-22-16-3-2-11-6-15-13-8-18-17(23-10-24-18)7-12(13)4-5-20(15)9-14(11)19(16)21/h2-3,7-8,15,21H,4-6,9-10H2,1H3/t15-/m0/s1
Standard InChI Key: PQECCKIOFCWGRJ-HNNXBMFYSA-N
Associated Targets(Human)
Coagulation factor III 225 Activities
Serotonin 1a (5-HT1a) receptor 14969 Activities
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Dopamine D2 receptor 23596 Activities
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Dopamine D1 receptor 9720 Activities
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Serotonin 2a (5-HT2a) receptor 14758 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: 325.36 | Molecular Weight (Monoisotopic): 325.1314 | AlogP: 2.79 | #Rotatable Bonds: 1 |
| 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: 6.24 | CX LogP: 2.94 | CX LogD: 2.90 |
| Aromatic Rings: 2 | Heavy Atoms: 24 | QED Weighted: 0.87 | Np Likeness Score: 1.16 |
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. Sun H, Zhu L, Yang H, Qian W, Guo L, Zhou S, Gao B, Li Z, Zhou Y, Jiang H, Chen K, Zhen X, Liu H.. (2013) Asymmetric total synthesis and identification of tetrahydroprotoberberine derivatives as new antipsychotic agents possessing a dopamine D(1), D(2) and serotonin 5-HT(1A) multi-action profile., 21 (4): [PMID:23332346] [10.1016/j.bmc.2012.12.016] |
Source
Source(1):