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Chemistry

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Also known as: 28608-75-5, Lutexin, Luteolin 8-c-glucoside, Orientine, Luteolin-8-glucoside, 4h-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-8-beta-d-glucopyranosyl-5,7-dihydroxy-
Molecular Formula
C21H20O11
Molecular Weight
448.4  g/mol
InChI Key
PLAPMLGJVGLZOV-VPRICQMDSA-N
FDA UNII
IAX93XCW6C

Orientin
orientin is a natural product found in Pseudarrhenatherum longifolium, Itea omeiensis, and other organisms with data available.
1 2D Structure

Orientin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one
2.1.2 InChI
InChI=1S/C21H20O11/c22-6-14-17(28)18(29)19(30)21(32-14)16-11(26)4-10(25)15-12(27)5-13(31-20(15)16)7-1-2-8(23)9(24)3-7/h1-5,14,17-19,21-26,28-30H,6H2/t14-,17-,18+,19-,21+/m1/s1
2.1.3 InChI Key
PLAPMLGJVGLZOV-VPRICQMDSA-N
2.1.4 Canonical SMILES
C1=CC(=C(C=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)C4C(C(C(C(O4)CO)O)O)O)O)O
2.1.5 Isomeric SMILES
C1=CC(=C(C=C1C2=CC(=O)C3=C(O2)C(=C(C=C3O)O)[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)O)O
2.2 Other Identifiers
2.2.1 UNII
IAX93XCW6C
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 8-c-beta-glucopyranosyl-3',4',5,7-tetrahydroxyflav-2-en-3-one

2. Luteolin 8-c-beta-d-glucopyranoside

3. Luteolin-8-c-glucoside

4. Orientine

2.3.2 Depositor-Supplied Synonyms

1. 28608-75-5

2. Lutexin

3. Luteolin 8-c-glucoside

4. Orientine

5. Luteolin-8-glucoside

6. 4h-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-8-beta-d-glucopyranosyl-5,7-dihydroxy-

7. 8-beta-d-glucosylluteolin

8. Iax93xcw6c

9. Luteolin 8-glucoside

10. Chebi:7781

11. 2-(3,4-dihydroxyphenyl)-8-beta-d-glucopyranosyl-5,7-dihydroxy-4h-1-benzopyran-4-one

12. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-((2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)-4h-chromen-4-one

13. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

14. C10114

15. Orientin (flavone)

16. 8-glucosylluteolin

17. Luteolin-8-c-glucoside

18. 2-(3,4-dihydroxyphenyl)-8-beta-d-glucopyranosyl-5,7-dihydroxy-4h-chromen-4-one

19. 4h-1-benzopyran-4-one, 2-(3,4-dihydroxyphenyl)-8-.beta.-d-glucopyranosyl-5,7-dihydroxy-

20. Unii-iax93xcw6c

21. Nsc-133101

22. Use

23. Mfcd00017432

24. 8-.beta.-d-glucopyranosyl-3',4',5,7-tetrahydroxyflavone

25. Schembl25942

26. Orientin, Analytical Standard

27. Massbank Pr020063

28. Chembl520866

29. Orientin, >=97% (hplc)

30. Bdbm84982

31. Dtxsid60182790

32. Luteolin 8-c-b-d-glucopyranoside

33. Niaid Aids# 026706

34. Hms3886j16

35. Hy-n0405

36. Zinc4098560

37. 8-.beta.-d-glucosylluteolin

38. S9099

39. Akos015896746

40. Ccg-269214

41. Ncgc00482848-01

42. Ac-34280

43. As-73888

44. J17.734b

45. Luteolin 8-c-.beta.-glucopyranoside

46. Cs-0008937

47. O0503

48. Luteolin 8-c-.beta.-d-glucopyranoside

49. 608o755

50. A819507

51. Orientin, Primary Pharmaceutical Reference Standard

52. Q421676

53. 8-b-d-glucopyranosyl-3',4',7'-tetrahydroxyflavone

54. Q-100362

55. 2-(3,4-dihydroxyphenyl)-8-.beta.-d-glucopyranosyl-5,7-dihydroxy-4h-chromen-4-one

56. (1s)-1,5-anhydro-1-(2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4h-chromen-8-yl)-d-glucitol

57. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-(.beta.-d-glucopyranosyl)-4h-1-benzopyran-4-one

58. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]-4h-chromen-4-one

59. 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]chromen-4-one

60. 2-(3,4-dihydroxyphenyl)-8-.beta.-d-glucopyranosyl-5,7-dihydroxy-4h-1-benzopyran-4-one

61. 2-[3,4-bis(oxidanyl)phenyl]-8-[(2~{s},3~{r},4~{r},5~{s},6~{r})-6-(hydroxymethyl)-3,4,5-tris(oxidanyl)oxan-2-yl]-5,7-bis(oxidanyl)chromen-4-one; 5281675; 2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-8-[(2s,3r,4r,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]chromen-4-one

62. 8-(.beta.-d-glucopyranosyl)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4h-1-benzopyran-4-one

63. D-glucitol, 1,5-anhydro-1-c-(2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-4-oxo-4h-1-benzopyran-8-yl)-, (1s)-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 448.4 g/mol
Molecular Formula C21H20O11
XLogP3-0.2
Hydrogen Bond Donor Count8
Hydrogen Bond Acceptor Count11
Rotatable Bond Count3
Exact Mass448.10056145 g/mol
Monoisotopic Mass448.10056145 g/mol
Topological Polar Surface Area197 Ų
Heavy Atom Count32
Formal Charge0
Complexity729
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1

REF. STANDARDS & IMPURITIES

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