اکوبین

Also known as (1S,4aR,5S,7aS)-5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl beta-D-glucopyranoside, Rhinanthin

Aucubin is an iridoid glycoside. Iridoids are commonly found in plants and function as defensive compounds. Iridoids decrease the growth rates of many generalist herbivores.

Chemical data

Formula: C15H22O9
Molecular weight: 346.33 g/mol
IUPAC name: (2S,3R,4S,5S,6R)-2-[[(1S,4aR,5S,7aS)-5-hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl]oxy]-6-(hydroxymethyl)oxane-3,4,5-triol
SMILES: C1=CO[C@H]([C@H]2[C@@H]1[C@@H](C=C2CO)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O
InChIKey: RJWJHRPNHPHBRN-FKVJWERZSA-N
XLogP: -3
Polar surface area: 149 Å²
H-bond donors: 6
H-bond acceptors: 9
Formal charge: 0

via PubChem

Drug data · ChEMBL

Molecule type: Small molecule

via ChEMBL · EBI

Wikidata facts

Mass: 346.126382

Show 4 more facts

Commons category: Aucubin
chemical formula: C₁₅H₂₂O₉
canonical SMILES: C1=COC(C2C1C(C=C2CO)O)OC3C(C(C(C(O3)CO)O)O)O
isomeric SMILES: C1=CO[C@H]([C@H]2[C@@H]1[C@@H](C=C2CO)O)O[C@H]3[C@@H]([C@H]([C@@H]([C@H](O3)CO)O)O)O

Sources (4)

via Wikidata · CC0