Compound Selection

Formula: C33H40O15

MW: 676.67

CAS: 489-32-7

Smiles: c12c(c(c(cc1O)O[C@@H]1O[C@@H](C([C@@H](C1O)O)O)CO)C\C=C(\C)C)oc(c(c2=O)OC1[C@@H]([C@@H]([C@H]([C@@H](O1)C)O)O)O)c1ccc(cc1)OC

THERAPEUTIC CATEGORY: antioxidant,[8][9] antidepressant[10][11][12] and nootropic[13][14]

REFERENCE: 1. Liu JJ, Li SP, Wang YT. Optimization for quantitative determination of four flavonoids in Epimedium by capillary zone electrophoresis coupled with diode array detection using central composite design. Journal of Chromatography A. 2006 Jan 27;1103(2):344-9. PMID 16337210 2. ^ Makarova MN, Pozharitskaya ON, Shikov AN, Tesakova SV, Makarov VG, Tikhonov VP. Effect of lipid-based suspension of Epimedium koreanum Nakai extract on sexual behavior in rats. Journal of Ethnopharmacology. 2007 Dec 3;114(3):412-6. PMID 17890032 3.^ 53: Related Articles, LinksJiang Z, Hu B, Wang J, Tang Q, Tan Y, Xiang J, Liu J. Effect of icariin on cyclic GMP levels and on the mRNA expression of cGMP-binding cGMP-specific phosphodiesterase (PDE5) in penile cavernosum. Journal of the Huazhong University of Science and Technology. 2006;26(4):460-2. PMID 17120748 4.^ Ning H, Xin ZC, Lin G, Banie L, Lue TF, Lin CS. Effects of icariin on phosphodiesterase-5 activity in vitro and cyclic guanosine monophosphate level in cavernous smooth muscle cells. Urology. 2006 Dec;68(6):1350-4. PMID 17169663 5. ^ Dell'agli M, Galli GV, Dal Cero E, Belluti F, Matera R, Zironi E, Pagliuca G, Bosisio E. Potent Inhibition of Human Phosphodiesterase-5 by Icariin Derivatives. Journal of Natural Products. 2008 Sep 9. PMID 18778098 6. ^ Xu HB, Huang ZQ. Icariin enhances endothelial nitric-oxide synthase expression on human endothelial cells in vitro. Vascular Pharmacology. 2007 Jul;47(1):18-24. PMID 17499557 7. ^ Zhang ZB, Yang QT. The testosterone mimetic properties of icariin. Asian Journal of Andrology. 2006 Sep;8(5):601-5. PMID 16751992 8. ^ Xie J, Sun W, Duan K, Zhang Y. Chemical constituents of roots of Epimedium wushanense and evaluation of their biological activities. Natural Product Research. 2007 Jun;21(7):600-5. PMID 17613817 9. ^ Zhao F, Tang YZ, Liu ZQ. Protective effect of icariin on DNA against radical-induced oxidative damage. Journal of Pharmacy and Pharmacology. 2007 Dec;59(12):1729-32. PMID 18053336 10.^ Pan Y, Kong L, Xia X, Zhang W, Xia Z, Jiang F. Antidepressant-like effect of icariin and its possible mechanism in mice. Pharmacology, Biochemistry and Behaviour. 2005 Dec;82(4):686-94. PMID 16380159 11.^ Pan Y, Zhang WY, Xia X, Kong LD. Effects of icariin on hypothalamic-pituitary-adrenal axis action and cytokine levels in stressed Sprague-Dawley rats. Biological and Pharmaceutical Bulletin. 2006 Dec;29(12):2399-403. PMID 17142971 12. ^ Pan Y, Kong LD, Li YC, Xia X, Kung HF, Jiang FX. Icariin from Epimedium brevicornum attenuates chronic mild stress-induced behavioral and neuroendocrinological alterations in male Wistar rats. Pharmacology, Biochemistry and Behaviour. 2007 May;87(1):130-40. PMID 17509675 13. ^ Luo Y, Nie J, Gong QH, Lu YF, Wu Q, Shi JS. Protective effects of icariin against learning and memory deficits induced by aluminium in rats. Clinical and Experimental Pharmacology and Physiology. 2007 Aug;34(8):792-5. PMID 17600559 14. ^ Zheng M, Qu L, Lou Y. Effects of icariin combined with Panax notoginseng saponins on ischemia reperfusion-induced cognitive impairments related with oxidative stress and CA1 of hippocampal neurons in rat. Phytotherapy Research. 2008 May;22(5):597-604. PMID 18398927 15.^ Yin XX, Chen ZQ, Liu ZJ, Ma QJ, Dang GT. Icariine stimulates proliferation and differentiation of human osteoblasts by increasing production of bone morphogenetic protein 2. Chinese Medical Journal (English). 2007 Feb 5;120(3):204-10. PMID 17355822 16.^ Zhang G, Qin L, Shi Y. Epimedium-derived phytoestrogen flavonoids exert beneficial effect on preventing bone loss in late postmenopausal women: a 24-month randomized, double-blind and placebo-controlled trial. Journal of Bone and Mineral Research. 2007 Jul;22(7):1072-9. PMID 17419678 17.^ Chen KM, Ge BF, Liu XY, Ma PH, Lu MB, Bai MH, Wang Y. Icariin inhibits the osteoclast formation induced by RANKL and macrophage-colony stimulating factor in mouse bone marrow culture. Pharmazie. 2007 May;62(5):388-91. PMID 17557750 18. ^ Huang J, Yuan L, Wang X, Zhang TL, Wang K. Icaritin and its glycosides enhance osteoblastic, but suppress osteoclastic, differentiation and activity in vitro. Life Sciences. 2007 Aug 16;81(10):832-40. PMID 17764702 19.^ Zhang DW, Cheng Y, Wang NL, Zhang JC, Yang MS, Yao XS. Effects of total flavonoids and flavonol glycosides from Epimedium koreanum Nakai on the proliferation and differentiation of primary osteoblasts. Phytomedicine. 2008 Jan;15(1-2):55-61. PMID 17482445 20.^ Qin L, Han T, Zhang Q, Cao D, Nian H, Rahman K, Zheng H. Antiosteoporotic chemical constituents from Er-Xian Decoction, a traditional Chinese herbal formula. Journal of Ethnopharmacology. 2008 Jul 23;118(2):271-9. PMID 18501540

SOURCE: Icariin is a flavonoid glycoside compound derived from several species of plants in the Epimedium family, which are commonly known as Horny Goat Weed or Yin Yang Huo.[1]

ACCEPTORS: 15

DONORS: 8

ROTATION BONDS: 6

N+O: 15

Chiral Centers: 10

LogP: -2.13

LogS: -3.79

LIPINSKI: 1

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