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ID: ALA47043
Max Phase: Preclinical
Molecular Formula: C21H22ClNO4
Molecular Weight: 352.41
Molecule Type: Small molecule
Associated Items:
Representations
Canonical SMILES: COc1cc2c(cc1OC)-c1cc3cc(OC)c(OC)cc3c[n+]1CC2.[Cl-]
Standard InChI: InChI=1S/C21H22NO4.ClH/c1-23-18-8-13-5-6-22-12-15-10-20(25-3)19(24-2)9-14(15)7-17(22)16(13)11-21(18)26-4;/h7-12H,5-6H2,1-4H3;1H/q+1;/p-1
Standard InChI Key: LNFUSMKUTAMOQF-UHFFFAOYSA-M
Associated Targets(Human)
HepG2 196354 Activities
KM12C 20 Activities
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Associated Targets(non-human)
Plasmodium falciparum 966862 Activities
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Mus musculus 284745 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: 352.41 | Molecular Weight (Monoisotopic): 352.1543 | AlogP: 3.38 | #Rotatable Bonds: 4 |
| Polar Surface Area: 40.80 | Molecular Species: NEUTRAL | HBA: 4 | HBD: 0 |
| #RO5 Violations: 0 | HBA (Lipinski): 5 | HBD (Lipinski): 0 | #RO5 Violations (Lipinski): 0 |
| CX Acidic pKa: | CX Basic pKa: | CX LogP: -1.22 | CX LogD: -1.22 |
| Aromatic Rings: 3 | Heavy Atoms: 26 | QED Weighted: 0.68 | Np Likeness Score: 1.11 |
References
| 1. McCall DL, Alexander J, Barber J, Jaouhari RG, Satoskar A, Waigh RD. (1994) The first protoberberine alkaloid analogue with in vivo antimalarial activity, 4 (14): [10.1016/S0960-894X(00)80357-1] |
| 2. Wang YX, Wang YP, Zhang H, Kong WJ, Li YH, Liu F, Gao RM, Liu T, Jiang JD, Song DQ.. (2009) Synthesis and biological evaluation of berberine analogues as novel up-regulators for both low-density-lipoprotein receptor and insulin receptor., 19 (21): [PMID:19800225] [10.1016/j.bmcl.2009.09.059] |
| 3. Xu B, Jiang X, Xiong J, Lan J, Tian Y, Zhong L, Wang X, Xu N, Cao H, Zhang W, Zhang H, Hong X, Zhan YY, Zhang Y, Hu T.. (2020) Structure-Activity Relationship Study Enables the Discovery of a Novel Berberine Analogue as the RXRα Activator to Inhibit Colon Cancer., 63 (11): [PMID:32391701] [10.1021/acs.jmedchem.0c00088] |
Source
Source(1):