aucubin

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

~5 min read

Encyclopedic overview

5 sections

Contents

Natural occurrences
Health effects
Chemistry
Biosynthesis
References

{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 460426427 | ImageFile= Aucubin skeletal.svg | ImageSize= 260px | ImageFile2= Aucubin 3D BS.png | ImageSize2= 260px | IUPACName = (1S,4aR,5S,7aS)-5-Hydroxy-7-(hydroxymethyl)-1,4a,5,7a-tetrahydrocyclopenta[c]pyran-1-yl β-D-glucopyranoside | SystematicName = (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 | OtherNames = Aucubin |Section1= |Section2= |Section3= }}

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.

Excerpted from Wikipedia’s “aucubin” article, available under the CC BY-SA 4.0 licence.