bacopaside II   Click here for help

GtoPdb Ligand ID: 13096

Compound class: Synthetic organic
Comment: Bacopaside II is a bioactive phytochemical isolated from the medicinal plant Bacopa monnieri.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 18
Hydrogen bond donors 10
Rotatable bonds 10
Topological polar surface area 276.14
Molecular weight 929.1
XLogP 2.94
No. Lipinski's rules broken 3
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CC(=C[C@@H]1CO[C@]23C[C@]4(CO2)[C@H](CC[C@@H]5[C@@]6(C)CC[C@@H](C(C)(C)[C@@H]6CC[C@]54C)O[C@H]7[C@@H]([C@H]([C@@H]([C@@H](CO)O7)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@@H](CO)O8)O)O)O)O[C@H]9[C@@H]([C@H]([C@H](CO)O9)O)O)[C@H]3[C@@]1(C)O)C
Isomeric SMILES CC(=C[C@@H]1CO[C@]23C[C@]4(CO2)[C@@H]([C@H]3[C@@]1(C)O)CC[C@H]5[C@]4(CC[C@@H]6[C@@]5(CC[C@@H](C6(C)C)O[C@H]7[C@@H]([C@H]([C@@H]([C@H](O7)CO)O)O[C@H]8[C@@H]([C@H]([C@@H]([C@H](O8)CO)O)O)O)O[C@H]9[C@@H]([C@H]([C@@H](O9)CO)O)O)C)C)C
InChI InChI=1S/C47H76O18/c1-21(2)14-22-18-58-47-19-46(20-59-47)23(38(47)45(22,7)57)8-9-28-43(5)12-11-29(42(3,4)27(43)10-13-44(28,46)6)63-41-37(65-39-34(55)31(52)25(16-49)61-39)36(32(53)26(17-50)62-41)64-40-35(56)33(54)30(51)24(15-48)60-40/h14,22-41,48-57H,8-13,15-20H2,1-7H3/t22-,23-,24-,25+,26-,27+,28-,29+,30-,31+,32-,33+,34-,35-,36+,37-,38+,39+,40+,41+,43+,44-,45+,46+,47-/m1/s1
InChI Key WZWPYJOPCULCLQ-UOXCDNDQSA-N
References
1. Palethorpe HM, Smith E, Tomita Y, Nakhjavani M, Yool AJ, Price TJ, Young JP, Townsend AR, Hardingham JE. (2019)
Bacopasides I and II Act in Synergy to Inhibit the Growth, Migration and Invasion of Breast Cancer Cell Lines.
Molecules, 24 (19). [PMID:31574930]
2. Pei JV, Kourghi M, De Ieso ML, Campbell EM, Dorward HS, Hardingham JE, Yool AJ. (2016)
Differential Inhibition of Water and Ion Channel Activities of Mammalian Aquaporin-1 by Two Structurally Related Bacopaside Compounds Derived from the Medicinal Plant Bacopa monnieri.
Mol Pharmacol, 90 (4): 496-507. [PMID:27474162]