Compound: Icariin
SMILES: O=c1c(O[C@@H]2O[C@H]([C@H](O)[C@H]([C@H]2O)O)C)c(oc3c1c(O)cc(c3CC=C(C)C)O[C@@H]4O[C@@H]([C@@H](O)[C@@H]([C@H]4O)O)CO)-c5ccc(OC)cc5
InChIKey: TZJALUIVHRYQQB-XLRXWWTNSA-N
Synonyms: Icariin, 489-32-7, Ieariline, VNM47R2QSQ, Epimedii herba icariin, CHEBI:78420, DTXSID00964133, 3-((6-Deoxymannopyranosyl)oxy)-7-(glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-4H-1-benzopyran-4-one, 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, 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, RefChem:147596, DTXCID301391843, 610-440-0, 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)-4H-chromen-4-one, Icariine, MFCD00210516, Icarrin, 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-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]oxy}-4H-chromen-4-one, C33H40O15, 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, SMR000466309, UNII-VNM47R2QSQ, -Anhydroicaritin, 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-(((2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-3-(((2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H, Icariin (Standard), Horny goat weed extract, Spectrum2_001695, Spectrum3_001130, Spectrum4_001975, Spectrum5_000933, Icariin, analytical standard, BSPBio_002599, KBioGR_002475, MLS000759413, MLS001424083, MLS006011789, SCHEMBL312615, SPECTRUM1505257, SPBio_001650, CHEMBL553204, orb1304925, orb3140895, Icariin, >=94% (HPLC), SCHEMBL30140586, GTPL13728, HY-N0014R, KBio3_002099, Anhydroicaritin Impurity 6;Icariin, HMS2051J13, HMS2235I20, 3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-buten-1-yl)-4H-1-benzopyran-4-one, EPIMEDII HERBA ICARIIN [MI], EX-A6783, HY-N0014, MSK40107, BBL010487, BDBM50027363, CCG-38780, EBC-11084, STK801622, AKOS005614005, CCG-100955, CS-3675, DB12052, MI08119, NC00205, SDCCGMLS-0066754.P001, NCGC00178583-01, 4H-1-Benzopyran-4-one, 3-((6-deoxy-alpha-L-mannopyranosyl)oxy)-7-(beta-D-glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-, 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxy-3-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-chromen-4-one, VS-02526, NS00014970, C17555, 4'-Me ether, 3-O-alpha- L -rhamnopyranoside;, AB00639912-06, SR-01000759346, Q5985057, SR-01000759346-4, BRD-K65639003-001-02-5, BRD-K65639003-001-05-8, BRD-K65639003-001-09-0, 3-[(6-Deoxy-?-L-mannopyranosyl)oxy]-7-?-D-glucopyranosyloxy-5-hydroxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one, 3-[(6-Deoxy-alpha-L-mannopyranosyl)oxy]-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4-oxo-4H-1-benzopyran-7-yl beta-D-glucopyranoside, 4H-1-BENZOPYRAN-4-ONE, 3-((6-DEOXY-.ALPHA.-L-MANNOPYRANOSYL)OXY)-7-(.BETA.-D-GLUCOPYRANOSYLOXY)-5-HYDROXY-2-(4-METHOXYPHENYL)-8-(3-METHYL-2-BUTEN-1-YL)-, 5-HYDROXY-2-(4-METHOXYPHENYL)-8-(3-METHYLBUT-2-EN-1-YL)-7-{[3,4,5-TRIHYDROXY-6-(HYDROXYMETHYL)OXAN-2-YL]OXY}-3-[(3,4,5-TRIHYDROXY-6-METHYLOXAN-2-YL)OXY]-4H-CHROMEN-4-ONE
Theoretical properties:
molecular_formula: C33H40O15
molecular_weight: 676.7 g/mol
exact_mass: 676.23672056 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 8
hydrogen_bond_acceptor_count: 15
rotatable_bond_count: 9
heavy_atom_count: 48
topological_polar_surface_area: 234 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Icariin is 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). It has a role as an antioxidant, a bone density conservation agent, an EC 3.1.4.35 (3',5'-cyclic-GMP phosphodiesterase) inhibitor and a phytoestrogen. It is a member of flavonols and a glycosyloxyflavone.
chebi: 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-<small>L</small>-mannopyranoside, methyl ether, and β-D-glucopyranoside, respectively. A phoshphodiesterase-5 inhibitor, it is obtained from several species of plants in the genus <em>Epimedium</em> and is thought to be the main active ingredient of the Chinese herbal medicine Herba Epimedii (yinyanghuo).
chembl: ICARIIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Icariin is a chemical compound classified as a prenylated 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 plant belonging to the genus Epimedium which are commonly known as horny goat weed, Yin Yang Huo, and Herba epimedii. Extracts from these plants produce aphrodisiac effects, and are used in traditional Chinese medicine to enhance erectile function.