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

• ChemBase ID: 119441
• Molecular Formular: C33H40O15
• Molecular Mass: 676.6617
• Monoisotopic Mass: 676.23672058
• SMILES: c1(c(=O)c2c(oc1c1ccc(cc1)OC)c(c(O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)cc2O)CC=C(C)C)O[C@H]1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O
• Canonical SMILES: COc1ccc(cc1)c1oc2c(CC=C(C)C)c(O[C@@H]3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)cc(c2c(=O)c1O[C@@H]1O[C@@H](C)[C@@H]([C@H]([C@H]1O)O)O)O
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: 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
• IUPAC Traditional name: icariin; 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
• Synonyms: 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; Icariin; 4'-Me ether, 3-O-alpha- L -rhamnopyranoside; 7-O-beta-D-glucopyranoside; Icariin

Database IDs

• CAS Number: 489-32-7
• PubChem SID: 162102870
• PubChem CID: 5318997
• CHEMBL: 553204
• Chemspider ID: 4477421
• Wikipedia Title: Icariin

CALCULATED PROPERTIES

• Acid pKa: 7.068547
• H Acceptors: 15
• H Donor: 8
• LogD (pH = 5.5): 0.8005592
• LogD (pH = 7.4): 0.32218364
• Log P: 0.81203294
• Molar Refractivity: 166.6204 cm^3
• Polarizability: 65.346016 Å^3
• Polar Surface Area: 234.29 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Apperance: Yellow powder

Pharmacology Properties

• Admin Routes: Oral
• Legal Status: Legal
• Mechanism of Action: Calcium regulator; Neuronal injury inhibitor

Product Information

• Purity: 96.0
• Biological Source: Isol. from Epimedium spp.
• Application(s): Antineoplastic agent; Immunostimulant

REFERENCES

• Jain, A.C. et al., Aust. J. Chem., 1975, 28, 607, (synth)
• Miyaichi, Y. et al., Yakugaku Zasshi, 1994, 114, 186
• He, W. et al., Arzneim.-Forsch., 1995, 45, 910-913, (Icariin, pharmacol)
• Anam, E.A., Indian J. Heterocycl. Chem., 1997, 7, 59-62
• Jiyun, L. et al., Drugs of the Future, 1998, 23, 142-145, (Icariin, rev, pharmacol)