Structure via PubChem · Public domain (PubChem)
arctiin
Sign in to saveArctiin is a lignan found in many plants of the family Asteraceae, particularly the greater burdock (Arctium lappa) and Centaurea imperialis, and in Trachelospermum asiaticum, Saussurea heteromalla, and Forsythia viridissima. It is the glucoside of arctigenin.
Chemical data
- Formula
- C27H34O11
- Molecular weight
- 534.6 g/mol
- IUPAC name
- (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-[[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl]oxolan-2-one
- SMILES
- COC1=C(C=C(C=C1)C[C@H]2COC(=O)[C@@H]2CC3=CC(=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC)OC
- InChIKey
- XOJVHLIYNSOZOO-SWOBOCGESA-N
- XLogP
- 1.8
- Polar surface area
- 153 Ų
- H-bond donors
- 4
- H-bond acceptors
- 11
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 534.21
Show 4 more facts
- found in taxon
- Centaurea melitensis
- chemical formula
- C₂₇H₃₄O₁₁
- isomeric SMILES
- COC1=C(C=C(C=C1)C[C@H]2COC(=O)[C@@H]2CC3=CC(=C(C=C3)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OC)OC
- canonical SMILES
- COC1=C(C=C(C=C1)CC2COC(=O)C2CC3=CC(=C(C=C3)OC4C(C(C(C(O4)CO)O)O)O)OC)OC
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
2 sectionsContents
- References
- External links
{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 457138982 | ImageFile = Arctiin.svg | ImageClass = skin-invert-image | ImageSize = 250 | IUPACName = (3R,4R)-4-[(3,4-dimethoxyphenyl)methyl]-3-{[3-methoxy-4-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxyphenyl]methyl}oxolan-2-one | OtherNames = |Section1= |Section2= |Section3= }} Arctiin is a lignan found in many plants of the family Asteraceae, particularly the greater burdock (Arctium lappa) and Centaurea imperialis, and in Trachelospermum asiaticum, Saussurea heteromalla, and Forsythia viridissima. It is the glucoside of arctigenin.
Arctiin and arctigenin have shown anticancer effects in animal research. They have been found to act as agonists of the adiponectin receptor 1.
Excerpted from Wikipedia’s “arctiin” article, available under the CC BY-SA 4.0 licence.