Structure via PubChem · Public domain (PubChem)
fagopyrin
Sign in to saveFagopyrin is a phototoxic substance found in the flowers of buckwheat (Fagopyrum esculentum). Their chemical structure contains a naphthodianthrone skeleton similar to that of hypericin. After exposure, fagopyrin can cause sensitivity to light, also called fagopyrism, an itchy skin rash.
Chemical data
- Formula
- C40H34N2O8
- Molecular weight
- 670.7 g/mol
- IUPAC name
- 5,7,11,18,22,24-hexahydroxy-13,16-dimethyl-6,23-di(piperidin-2-yl)octacyclo[13.11.1.12,10.03,8.04,25.019,27.021,26.014,28]octacosa-1(27),2(28),3,5,7,10,12,14,16,18,21,23,25-tridecaene-9,20-dione
- SMILES
- CC1=CC(=C2C3=C4C5=C6C(=C13)C(=CC(=C6C(=O)C7=C(C(=C(C(=C57)C8=C4C(=C(C(=C8O)C9CCCCN9)O)C2=O)O)C1CCCCN1)O)O)C)O
- InChIKey
- ROFJUMITFMRBRF-UHFFFAOYSA-N
- XLogP
- 7.4
- Polar surface area
- 180 Ų
- H-bond donors
- 8
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 670.231516
Show 3 more facts
- chemical formula
- C₄₀H₃₄N₂O₈
- canonical SMILES
- CC1=CC(=C2C3=C1C4=C5C(=C(C=C4C)O)C(=O)C6=C(C(=C(C7=C6C5=C3C8=C7C(=C(C(=C8C2=O)O)C9CCCCN9)O)O)C1CCCCN1)O)O
- Commons category
- Fagopyrin
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
5 sectionsContents
- History and occurrence
- Structure
- Biosynthesis and properties
- References
- External links
Fagopyrin is a phototoxic substance found in the flowers of buckwheat (Fagopyrum esculentum). Their chemical structure contains a naphthodianthrone skeleton similar to that of hypericin. After exposure, fagopyrin can cause sensitivity to light, also called fagopyrism, an itchy skin rash.
== History and occurrence == The substance was isolated from flowers of the red-flowering genotype of buckwheat in 1941, and its chemical structure, which is derived from hypericin, was first described in 1979. Within the edible parts of the plant, it is found exclusively in the brown fruit husk of buckwheat grains.
Excerpted from Wikipedia’s “fagopyrin” article, available under the CC BY-SA 4.0 licence.
Available in 7 languages
via Wikidata sitelinks · CC0