Icariin

Icariin

Names
IUPAC name 5-Hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7- [(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3- [(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxychromen-4-one
Identifiers
CAS Number	489-32-7
3D model (Jmol)	Interactive image
ChEBI	CHEBI:78420 N
ChEMBL	ChEMBL553204 Y
ChemSpider	4477421 Y
ECHA InfoCard	100.107.649
PubChem	5318997
InChI InChI=1S/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1 Y Key: TZJALUIVHRYQQB-XLRXWWTNSA-N Y InChI=1/C33H40O15/c1-13(2)5-10-17-19(45-33-28(42)26(40)23(37)20(12-34)46-33)11-18(35)21-24(38)31(48-32-27(41)25(39)22(36)14(3)44-32)29(47-30(17)21)15-6-8-16(43-4)9-7-15/h5-9,11,14,20,22-23,25-28,32-37,39-42H,10,12H2,1-4H3/t14-,20+,22-,23+,25+,26-,27+,28+,32-,33+/m0/s1 Key: TZJALUIVHRYQQB-XLRXWWTNBA
SMILES O=C3C(\O[C@@H]1O[C@H]([C@H](O)[C@@H](O)[C@H]1O)C)=C(/Oc4c(c(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)cc(O)c34)C\C=C(/C)C)c5ccc(OC)cc5
Properties
Chemical formula	C33H40O15
Molar mass	676.67 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-

Icariin is a chemical compound classified as a flavonol glycoside, a type of flavonoid. It is the 8-prenyl derivative of kaempferol 3,7-O-diglucoside. The compound has been isolated from several species of plants belonging to the genus Epimedium which are commonly known as Horny Goat Weed or Yin Yang Huo. Extracts from these plants are reputed to produce aphrodisiac effects, and are used in traditional Chinese medicine to enhance erectile function.

It is thought that icariin is an active component of Epimedium extracts, as it has been shown to share several mechanisms of action with compounds used in Western medicine to treat impotence. In particular, icariin is a weak PDE5 inhibitor in vitro and enhances the production of nitric oxide, as well as mimicking the effects of testosterone in rats. It is a weak antioxidant and has antidepressant-like effects in mice. It also has neuroprotective effects in rats.