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MolPort-001-742-524

MolPort-001-742-524

Synopsis, Chemistry

ANALYTICAL SOLUTION(s)

1 USP Standards, 3 Other Ref. Standards

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Also known as: 82854-37-3, Dsstox_cid_13469, Chebi:4745, I04o1dt48t, [(2r,3r,4r,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-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, Ac1nqz1q

Molecular Formula

C₃₅H₄₆O₂₀

Molecular Weight

786.7 g/mol

InChI Key

FSBUXLDOLNLABB-ISAKITKMSA-N

FDA UNII

I04O1DT48T

echinacoside is a natural product found in Jasminum mesnyi, Pedicularis plicata, and other organisms with data available.

1 2D Structure

MolPort-001-742-524

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-[[(2R,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-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/C35H46O20/c1-14-24(42)26(44)29(47)35(51-14)55-32-30(48)34(49-9-8-16-3-6-18(38)20(40)11-16)53-22(13-50-33-28(46)27(45)25(43)21(12-36)52-33)31(32)54-23(41)7-4-15-2-5-17(37)19(39)10-15/h2-7,10-11,14,21-22,24-40,42-48H,8-9,12-13H2,1H3/b7-4+/t14-,21+,22+,24-,25+,26+,27-,28+,29+,30+,31+,32+,33+,34+,35-/m0/s1

2.1.3 InChI Key

FSBUXLDOLNLABB-ISAKITKMSA-N

2.1.4 Canonical SMILES

CC1C(C(C(C(O1)OC2C(C(OC(C2OC(=O)C=CC3=CC(=C(C=C3)O)O)COC4C(C(C(C(O4)CO)O)O)O)OCCC5=CC(=C(C=C5)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[C@H]4[C@@H]([C@H]([C@@H]([C@H](O4)CO)O)O)O)OCCC5=CC(=C(C=C5)O)O)O)O)O)O

2.2 Other Identifiers

2.2.1 UNII

I04O1DT48T

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 82854-37-3

2. Dsstox_cid_13469

3. Chebi:4745

4. I04o1dt48t

5. [(2r,3r,4r,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-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

6. Ac1nqz1q

7. Unii-i04o1dt48t

8. Echinacoside,(s)

9. Mfcd00075695

10. Surecn525502

11. Dsstox_rid_79077

12. Dsstox_gsid_33469

13. Echinacoside [usp-rs]

14. Echinacoside, 98% (hplc)

15. Schembl525502

16. Chembl510539

17. Megxp0_001773

18. Dtxsid0033469

19. Echinacoside, Analytical Standard

20. Hms3885k04

21. Hy-n0020

22. Tox21_200945

23. S3783

24. Zinc85504689

25. Akos015897141

26. Ccg-270479

27. Cs-3400

28. Db15488

29. Ncgc00091915-01

30. Ncgc00091915-02

31. Ncgc00258498-01

32. Ac-34699

33. As-56376

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

35. Cas-82854-37-3

36. A12039

37. 854e373

38. Q475631

39. Echinacoside, Primary Pharmaceutical Reference Standard

40. Echinacoside, United States Pharmacopeia (usp) Reference Standard

41. (2r,3r,4r,5r,6r)-6-(3,4-dihydroxyphenethoxy)-5-hydroxy-2-((((2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2h-pyran-2-yl)oxy)methyl)-4-(((2s,3r,4r,5r,6s)-3,4,5-trihydroxy-6-methyltetrahydro-2h-pyran-2-yl)oxy)tetrahydro-2h-pyran-3-yl 3-(3,4-dihydroxyphenyl)acrylate

42. .beta.-d-glucopyranoside, 2-(3,4-dihydroxyphenyl)ethyl O-6-deoxy-.alpha.-l-mannopyranosyl-(1->3)-o-(.beta.-d-glucopyranosyl-(1->6))-, 4-(3-(3,4-dihydroxyphenyl)-2-propenoate)

43. [(2r,3r,4r,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydropyran-2-yl]oxymethyl]-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

44. 2-(3,4-dihydroxyphenyl)ethyl 6-deoxy-alpha-l-mannopyranosyl-(1-3)-[beta-d-glucopyranosyl-(1-6)]-4-o-[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]-beta-d-glucopyranoside

45. 3,4-dihydroxyphenethyl 3-o-(alpha-l-rhamnopyranosyl)-4-o-(3,4-dihydroxycinnamoyl)-6-o-(beta-d-glucopyranosyl)-beta-d-glucopyranoside

46. 737806-07-4

47. Echinacoside (ang, Pal) (constituent Of Echinacea Angustifolia Root, Echinacea Pallida Root, Echinacea Purpurea Root And Echinacea Purpurea Aerial Parts) [dsc]

48. Ncgc00091915-03![(2r,3r,4r,5r,6r)-6-[2-(3,4-dihydroxyphenyl)ethoxy]-5-hydroxy-2-[[(2r,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxymethyl]-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

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₃₅H₄₆O₂₀
Molecular Weight	786.7 g/mol
XLogP3	-2.1
Hydrogen Bond Donor Count	12
Hydrogen Bond Acceptor Count	20
Rotatable Bond Count	14
Exact Mass	786.25824385 g/mol
Monoisotopic Mass	786.25824385 g/mol
Topological Polar Surface Area	324 Å²
Heavy Atom Count	55
Formal Charge	0
Complexity	1230
Isotope Atom Count	0
Defined Atom Stereocenter Count	15
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 Absorption, Distribution and Excretion

Absorption

Animal studies suggest an oral bioavailability of 0.83%.

4.2 Metabolism/Metabolites

The metabolism of echinacoside has been investigated in rats and is thought to involve catechol O-methyltransferase as well as unspecified UDP-gluc- uronosyltransferases and sulfotransferases. A study of echinacoside's metabolism by human intestinal flora identified 13 metabolites which are produced independantly of human metabolism.

4.3 Mechanism of Action

The neuroprotective effects are thought to be mediated via effects on mitogen-activated protein kinase, nuclear factor kappa-B, caspases 3 and 8, as well as CHOP pathways.