Biological and Environmental Research Ontology

Last uploaded: December 23, 2022
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Preferred Name

icariin
Synonyms

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

ieariline
Definitions

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-alpha-L-mannopyranoside, methyl ether, and beta-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).
ID

http://purl.obolibrary.org/obo/CHEBI_78420
charge

0
database_cross_reference

PMID:23824956

PMID:24462390

PMID:18053336

PMID:17355822

PMID:24552978

PMID:17169663

LIPID_MAPS_instance:LMPK12112009

PMID:24265111

PMID:24435883

PMID:24295650

Reaxys:76280

PMID:17499557

PMID:24748177

PMID:17764702

PMID:16380159

PMID:17482445

PMID:24590261

PMID:17419678

PMID:22216122

LINCS:LSM-3462

PMID:23975599

PMID:17613817

PMID:24311544

PMID:18398927

PMID:18778098

PMID:17142971

Wikipedia:Icariin

PMID:17557750

PMID:16751992

PMID:24710854

PMID:18501540

PMID:17509675

PMID:24619236

KEGG:C17555

PMID:23772748

PMID:17120748

PMID:17600559

CAS:489-32-7
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-alpha-L-mannopyranoside, methyl ether, and beta-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).
formula

C33H40O15
has_exact_synonym

3-[(6-deoxy-alpha-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-chromen-7-yl beta-D-glucopyranoside
has_obo_namespace

chebi_ontology
has_related_synonym

ieariline
id

CHEBI:78420
in_subset

http://purl.obolibrary.org/obo/chebi#3_STAR
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
label

icariin
mass

676.66170
monoisotopicmass

676.23672
notation

CHEBI:78420
prefLabel

icariin
RO_0000087

http://purl.obolibrary.org/obo/CHEBI_50646

http://purl.obolibrary.org/obo/CHEBI_22586

http://purl.obolibrary.org/obo/CHEBI_71942

http://purl.obolibrary.org/obo/CHEBI_76989
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
subClassOf

http://purl.obolibrary.org/obo/CHEBI_50018

http://purl.obolibrary.org/obo/CHEBI_28802
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