Icariin

Synopsis, Chemistry

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Also known as: 489-32-7, Ieariline, 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, Chebi:78420, Mfcd00210516, Vnm47r2qsq

Molecular Formula

C₃₃H₄₀O₁₅

Molecular Weight

676.7 g/mol

InChI Key

TZJALUIVHRYQQB-XLRXWWTNSA-N

FDA UNII

VNM47R2QSQ

icariin is a natural product found in Epimedium pubescens, Epimedium grandiflorum, and other organisms with data available.

1 2D Structure

Icariin

2 Identification

2.1 Computed Descriptors

2.1.1 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

2.1.2 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

2.1.3 InChI Key

TZJALUIVHRYQQB-XLRXWWTNSA-N

2.1.4 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

2.1.5 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

2.2 Other Identifiers

2.2.1 UNII

VNM47R2QSQ

2.3 Synonyms

2.3.1 MeSH Synonyms

1. 3-((6-deoxymannopyranosyl)oxy)-7-(glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-4h-1-benzopyran-4-one

2.3.2 Depositor-Supplied Synonyms

1. 489-32-7

2. Ieariline

3. 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

4. Chebi:78420

5. Mfcd00210516

6. Vnm47r2qsq

7. Icariine

8. 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

9. 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

10. Smr000466309

11. Unii-vnm47r2qsq

12. Horny Goat Weed

13. Epimedium Extract

14. 3-((6-deoxymannopyranosyl)oxy)-7-(glucopyranosyloxy)-5-hydroxy-2-(4-methoxyphenyl)-8-(3-methyl-2-butenyl)-4h-1-benzopyran-4-one

15. Epimedii Herba Icariin

16. Spectrum2_001695

17. Spectrum3_001130

18. Spectrum4_001975

19. Spectrum5_000933

20. Icariin, Analytical Standard

21. Bspbio_002599

22. Kbiogr_002475

23. Mls000759413

24. Mls001424083

25. Mls006011789

26. Schembl312615

27. Spectrum1505257

28. Spbio_001650

29. Ambz0238

30. Chembl553204

31. Icariin, >=94% (hplc)

32. Kbio3_002099

33. Dtxsid00964133

34. Hms2051j13

35. Hms2235i20

36. Bcp18807

37. Epimedii Herba Icariin [mi]

38. Ex-a6783

39. Hy-n0014

40. Zinc3960893

41. Bbl010487

42. Bdbm50027363

43. Ccg-38780

44. Stk801622

45. Akos005614005

46. Am85785

47. Ccg-100955

48. Cs-3675

49. Db12052

50. Nc00205

51. Sdccgmls-0066754.p001

52. Ncgc00178583-01

53. 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)-

54. Vs-02526

55. N1705

56. C17555

57. Ab00639912-06

58. 489i327

59. A827628

60. Sr-01000759346

61. Q-100549

62. Q5985057

63. Sr-01000759346-4

64. Brd-k65639003-001-02-5

65. Brd-k65639003-001-05-8

66. Brd-k65639003-001-09-0

67. 3,5-dihydroxy-4\'-methoxy-6\'\',6\'\'-dimethyl-4\'\',5\'\'-dihydropyrano[2\'\',3\'\':7,8]-flavone

68. 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

69. 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)-

70. 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-7-(((2s,4s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)-3-(((3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)-4h-chromen-4-one

71. 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

72. 5-hydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-enyl)-7-((2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yloxy)-3-((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)-4h-chromen-4-one

2.4 Create Date

2005-08-08

3 Chemical and Physical Properties

Molecular Formula	C₃₃H₄₀O₁₅
Molecular Weight	676.7 g/mol
XLogP3	1.7
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	9
Exact Mass	676.23672056 g/mol
Monoisotopic Mass	676.23672056 g/mol
Topological Polar Surface Area	234 Å²
Heavy Atom Count	48
Formal Charge	0
Complexity	1170
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1