CHEBI:78420 - icariin

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ChEBI Name icariin
ChEBI ID CHEBI:78420
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).
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C33H40O15
Net Charge 0
Average Mass 676.66170
Monoisotopic Mass 676.237
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
SMILES COc1ccc(cc1)-c1oc2c(CC=C(C)C)c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)cc(O)c2c(=O)c1O[C@@H]1O[C@@H](C)[C@H](O)[C@@H](O)[C@H]1O
Roles Classification
Chemical Role(s): antioxidant
A substance that opposes oxidation or inhibits reactions brought about by dioxygen or peroxides.
Biological Role(s): 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(s): 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.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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
Database Links Databases
C17555 KEGG COMPOUND
Icariin Wikipedia
LMPK12112009 LIPID MAPS
LSM-3462 LINCS
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Registry Numbers Types Sources
489-32-7 CAS Registry Number KEGG COMPOUND
489-32-7 CAS Registry Number ChemIDplus
76280 Reaxys Registry Number Reaxys
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Last Modified
25 February 2016