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Synopsis

ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: Verbascoside, Kusaginin, 61276-17-3, Tjc 160, Acetoside, Verbacoside

Molecular Formula

C₂₉H₃₆O₁₅

Molecular Weight

624.6 g/mol

InChI Key

FBSKJMQYURKNSU-ZLSOWSIRSA-N

FDA UNII

3TGX09BD5B

verbascoside is a natural product found in Orobanche amethystea, Barleria lupulina, and other organisms with data available.

1 2D Structure

Acteoside

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R,3R,4R,5R,6R)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2S,3R,4R,5R,6S)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxyoxan-3-yl] (E)-3-(3,4-dihydroxyphenyl)prop-2-enoate

2.1.2 InChI

InChI=1S/C29H36O15/c1-13-22(36)23(37)24(38)29(41-13)44-27-25(39)28(40-9-8-15-3-6-17(32)19(34)11-15)42-20(12-30)26(27)43-21(35)7-4-14-2-5-16(31)18(33)10-14/h2-7,10-11,13,20,22-34,36-39H,8-9,12H2,1H3/b7-4+/t13-,20+,22-,23+,24+,25+,26+,27+,28+,29-/m0/s1

2.1.3 InChI Key

FBSKJMQYURKNSU-ZLSOWSIRSA-N

2.1.4 Canonical SMILES

CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O

2.1.5 Isomeric SMILES

C[C@H]1[C@@H]([C@H]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@H]2OC(=O)/C=C/C3=CC(=C(C=C3)O)O)CO)OCCC4=CC(=C(C=C4)O)O)O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

3TGX09BD5B

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-o-(6-deoxy-alpha-l-mannopyranosyl)-, 4-(3-(3,4-dihydroxyphenyl)-2-propenoate), (e)-beta-d-

2. Kusaginin

3. Tjc 160

4. Tjc-160

5. Verbascoside

2.3.2 Depositor-Supplied Synonyms

1. Verbascoside

2. Kusaginin

3. 61276-17-3

4. Tjc 160

5. Acetoside

6. Verbacoside

7. Nsc 603831

8. 3tgx09bd5b

9. Mfcd00221751

10. [(2r,3r,4r,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyl-tetrahydropyran-2-yl]oxy-tetrahydropyran-3-yl] (e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

11. 22323-52-0

12. Tjc-160

13. Unii-3tgx09bd5b

14. Nsc-603831

15. .beta.-d-glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-o-(6-deoxy-.alpha.-l-mannopyranosyl)-, 4-((2e)-3-(3,4-dihydroxyphenyl)-2-propenoate)

16. .beta.-d-glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-o-(6-deoxy-.alpha.-l-mannopyranosyl)-, 4-[(2e)-3-(3,4-dihydroxyphenyl)-2-propenoate]

17. Russetinol

18. Stereospermin

19. Acteoside; Verbascoside

20. Verbascoside [inci]

21. Glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-o-(6-deoxy-alpha-l-mannopyranosyl)-, 4-(3-(3,4-dihydroxyphenyl)-2-propenoate), (e)-beta-d-

22. Mls002473233

23. Schembl657970

24. Verbascoside [usp-rs]

25. Chebi:9953

26. Chembl231853

27. Chembl444478

28. Tjc160

29. Cid_5281800

30. Verbascoside, >=99% (hplc)

31. Chebi:132853

32. Cid_24978601

33. Dtxsid701021953

34. Hms2205k11

35. Hy-n0021

36. Zinc8234351

37. Bdbm50241867

38. S5458

39. Akos015897165

40. Ccg-270269

41. Db12996

42. Ncgc00378687-03

43. As-75167

44. Smr001397320

45. N1341

46. 276a173

47. B864379

48. Q411426

49. Q-100706

50. Verbascoside, Primary Pharmaceutical Reference Standard

51. Verbascoside, United States Pharmacopeia (usp) Reference Standard

52. ((2r,3r,4r,5r,6r)-6-(3,4-dihydroxyphenethoxy)-5-hydroxy-2-(hydroxymethyl)-4-((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)tetrahydro-2h-pyran-3-yl) 3-(3,4-dihydroxyphenyl)acrylate

53. ((2r,3r,4r,5r,6r)-6-(3,4-dihydroxyphenethoxy)-5-hydroxy-2-(hydroxymethyl)-4-((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yloxy)tetrahydro-2h-pyran-3-yl)3-(3,4-dihydroxyphenyl)acrylate

54. (2r,3r,4r,5r,6r)-6-(3,4-dihydroxyphenethoxy)-5-hydroxy-2-(hydroxymethyl)-4-(((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)tetrahydro-2h-pyran-3-yl (e)-3-(3,4-dihydroxyphenyl)acrylate

55. (2r,3r,4r,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-(hydroxymethyl)-4-{[(2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyloxan-2-yl]oxy}oxan-3-yl (2e)-3-(3,4-dihydroxyphenyl)prop-2-enoate

56. (3,4-dihydroxyphenyl)ethyl O-.alpha.-rhamnopyranosyl(1->3)-4-o-caffeoyl-.beta.-d Glucopyranoside

57. .beta.-d-glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl3-o-(6-deoxy-.alpha.-l-mannopyranosyl)-, 4-[(2e)-3-(3,4-dihydroxyphenyl)-2-propenoate]

58. 2-(3,4-dihydroxyphenyl)ethyl 3-o-(6-deoxy-alpha-l-mannopyranosyl)-4-o-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-beta-d-glucopyranoside

59. 2-(3,4-dihydroxyphenyl)ethyl 3-o-(alpha-l-rhamnopyranosyl)-4-o-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-beta-d-glucopyranoside

60. 3,4-dihydroxyphenethyl 3-o-alpha-l-rhamnopyranosyl-4-o-[3-(3,4-dihydroxyphenyl)acryloyl]-beta-d-glucopyranoside

61. Beta-d-glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl 3-o-(6-deoxy-alpha-l-mannopyranosyl)-, 4-[(2e)-3-(3,4-dihydroxyphenyl)-2-propenoate]

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₉H₃₆O₁₅
Molecular Weight	624.6 g/mol
XLogP3	-0.5
Hydrogen Bond Donor Count	9
Hydrogen Bond Acceptor Count	15
Rotatable Bond Count	11
Exact Mass	624.20542044 g/mol
Monoisotopic Mass	624.20542044 g/mol
Topological Polar Surface Area	245 Å²
Heavy Atom Count	44
Formal Charge	0
Complexity	936
Isotope Atom Count	0
Defined Atom Stereocenter Count	10
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	1
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

Immunosuppressive Agents

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)

Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)

Chelating Agents

Chemicals that bind to and remove ions from solutions. Many chelating agents function through the formation of COORDINATION COMPLEXES with METALS. (See all compounds classified as Chelating Agents.)

Anti-Infective Agents

Substances that prevent infectious agents or organisms from spreading or kill infectious agents in order to prevent the spread of infection. (See all compounds classified as Anti-Infective Agents.)

Antioxidants

Naturally occurring or synthetic substances that inhibit or retard oxidation reactions. They counteract the damaging effects of oxidation in animal tissues. (See all compounds classified as Antioxidants.)

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