Structure via PubChem · Public domain (PubChem)
icariin
Sign in to saveAlso known as ieariline
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. == References ==
Chemical data
- Formula
- C33H40O15
- Molecular weight
- 676.7 g/mol
- 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
- SMILES
- C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C5=CC=C(C=C5)OC)O)O)O
- InChIKey
- TZJALUIVHRYQQB-XLRXWWTNSA-N
- XLogP
- 1.7
- Polar surface area
- 234 Ų
- H-bond donors
- 8
- H-bond acceptors
- 15
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
1,751 papers- Icariin modulates carrageenan-induced acute inflammation through HO-1/Nrf2 and NF-kB signaling pathways.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2019
- Pharmacological effects of icariin.Advances in pharmacology (San Diego, Calif.) · 2020
- Icariin alleviates ferroptosis-related atherosclerosis by promoting autophagy in xo-LDL-induced vascular endothelial cell injury and atherosclerotic mice.Phytotherapy research : PTR · 2023
- Icariin and its metabolites regulate lipid metabolism: From effects to molecular mechanisms.Biomedicine & pharmacotherapy = Biomedecine & pharmacotherapie · 2020
- Icariin as a therapeutic agent in breast cancer: modulating apoptosis and suppressing proliferation.Journal of complementary & integrative medicine · 2025
via PubMed
Wikidata facts
- Mass
- 676.237
Show 5 more facts
- found in taxon
- Epimedium
- chemical formula
- C₃₃H₄₀O₁₅
- canonical SMILES
- CC1C(C(C(C(O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)OC4C(C(C(C(O4)CO)O)O)O)O)C5=CC=C(C=C5)OC)O)O)O
- isomeric SMILES
- C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)OC2=C(OC3=C(C2=O)C(=CC(=C3CC=C(C)C)O[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)C5=CC=C(C=C5)OC)O)O)O
- different from
- icaridin
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
{{Chembox | Verifiedfields = changed | verifiedrevid = 461936642
| ImageFile = Icariin.svg | ImageClass = skin-invert-image | ImageSize = 200px | ImageAlt =
Excerpted from Wikipedia’s “icariin” article, available under the CC BY-SA 4.0 licence.