5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one

• ChemBase ID: 72952
• Molecular Formular: C33H40O15
• Molecular Mass: 676.6617
• Monoisotopic Mass: 676.23672058
• SMILES: [C@H]1([C@H]([C@@H]([C@H](C(O1)Oc1cc(c2c(c1CC=C(C)C)oc(c(c2=O)OC1O[C@H]([C@@H]([C@H]([C@H]1O)O)O)C)c1ccc(cc1)OC)O)O)O)O)CO
• Canonical SMILES: COc1ccc(cc1)c1oc2c(CC=C(C)C)c(OC3O[C@H](CO)[C@H]([C@@H]([C@H]3O)O)O)cc(c2c(=O)c1OC1O[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-XGYHSCOOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}-4H-chromen-4-one
• IUPAC Traditional name: 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-{[(3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3-{[(3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}chromen-4-one
• Synonyms: Icariin

Database IDs

• CAS Number: 489-32-7
• PubChem SID: 162037872
• PubChem CID: 45358132

CALCULATED PROPERTIES

• Acid pKa: 8.268453
• H Acceptors: 15
• H Donor: 8
• LogD (pH = 5.5): 0.8112997
• LogD (pH = 7.4): 0.75738716
• 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

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2312

Research Area: Metabolic Disease , Neurological Disease
Biological Activity:
Icariin is a flavonol and PDE5 inhibitor with IC50 of 1.0, 0.75, and 1.1 μM for PDE5A1, A2, and A3, respectively. It enhances the production of bioactive nitric oxide, as well as mimicking the effects of testosterone. It also shows antioxidant, antidepressant and nootropic effects in animal studies, as well as stimulating osteoblast activity in bone tissue which has been linked to a possible therapeutic role in the treatment of osteoporosis. [1][2]References on Icariin[1] http://en.wikipedia.org/wiki/Icariin, , [2] Urology., 2006 Dec, 68(6):1350-4.

REFERENCES

• Ning H et al. Urology. 2006 Dec;68(6):1350-4.