malvidin-3-glucoside   Click here for help

GtoPdb Ligand ID: 12427

Synonyms: Enin | Malvidin 3-O-beta-D-glucoside | Malvidin 3-O-glucoside | Oenin
Compound class: Natural product
Comment: Malvidin-3-glucoside is a bitter tasting compound that is found in plants including Visnea mocanera and Hibiscus syriacus, and is also produced by Saccharomyces cerevisiae.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 11
Hydrogen bond donors 7
Rotatable bonds 6
Topological polar surface area 178.53
Molecular weight 493.44
XLogP 0.52
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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Canonical SMILES COC1=CC(=CC(=C1O)OC)C2=[O+]C3=C(C=C2O[C@H]4[C@@H]([C@H]([C@@H]([C@@H](CO)O4)O)O)O)C(=CC(=C3)O)O
Isomeric SMILES COC1=CC(=CC(=C1O)OC)C2=[O+]C3=CC(=CC(=C3C=C2O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
InChI InChI=1S/C23H24O12/c1-31-14-3-9(4-15(32-2)18(14)27)22-16(7-11-12(26)5-10(25)6-13(11)33-22)34-23-21(30)20(29)19(28)17(8-24)35-23/h3-7,17,19-21,23-24,28-30H,8H2,1-2H3,(H2-,25,26,27)/p+1/t17-,19-,20+,21-,23-/m1/s1
InChI Key PXUQTDZNOHRWLI-OXUVVOBNSA-O
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
TAS2R7 Hs Agonist Agonist 4.9 pEC50 - 1
pEC50 4.9 (EC50 1.26x10-5 M) [1]