icariin (CHEBI:78420)

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CHEBI:78420 - icariin

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ChEBI ID	CHEBI:78420
ChEBI Name	icariin
Stars
Definition	A member of the class of flavonols that is kaempferol which is substituted at position 8 by a 3-methylbut-2-en-1-yl group and in which the hydroxy groups at positions 3, 4', and 7 have been converted to the corresponding 6-deoxy-α-L-mannopyranoside, methyl ether, and β-D-glucopyranoside, respectively. A phoshphodiesterase-5 inhibitor, it is obtained from several species of plants in the genus Epimedium and is thought to be the main active ingredient of the Chinese herbal medicine Herba Epimedii (yinyanghuo).
Last Modified	25 February 2016
Submitter	Gareth Owen
Downloads	Molfile

Formula	C33H40O15
Net Charge	0
Average Mass	676.668
Monoisotopic Mass	676.23672
SMILES	COc1ccc(-c2oc3c(CC=C(C)C)c(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)cc(O)c3c(=O)c2O[C@@H]2O[C@@H](C)[C@H](O)[C@@H](O)[C@H]2O)cc1
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
InChIKey	TZJALUIVHRYQQB-XLRXWWTNSA-N

Wikipedia

Roles Classification

Chemical Role:	antioxidant A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Roles:	phytoestrogen Any compound produced by a plant that happens to have estrogenic activity. EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor An EC 3.1.4.* (phosphoric diester hydrolase) inhibitor that blocks the action of 3',5'-cyclic-GMP phosphodiesterase (EC 3.1.4.35).
Application:	bone density conservation agent An agent that inhibits bone resorption and/or favor bone mineralization and bone regeneration. Used to heal bone fractures and to treat bone diseases such as osteopenia and osteoporosis.

ChEBI Ontology

Outgoing Relation(s)
	icariin (CHEBI:78420) has role antioxidant (CHEBI:22586)
	icariin (CHEBI:78420) has role bone density conservation agent (CHEBI:50646)
	icariin (CHEBI:78420) has role EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor (CHEBI:71942)
	icariin (CHEBI:78420) has role phytoestrogen (CHEBI:76989)
	icariin (CHEBI:78420) is a flavonols (CHEBI:28802)
	icariin (CHEBI:78420) is a glycosyloxyflavone (CHEBI:50018)

IUPAC Name
3-[(6-deoxy-α-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-7-yl β-D-glucopyranoside

Synonym	Source
ieariline	ChemIDplus

Manual Xrefs	Databases
Icariin	Wikipedia
C17555	KEGG COMPOUND
LMPK12112009	LIPID MAPS
LSM-3462	LINCS

Registry Numbers	Sources
Reaxys:76280	Reaxys
CAS:489-32-7	ChemIDplus
CAS:489-32-7	KEGG COMPOUND

Citations