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Technical details about Cynarin, learn more about the structure, uses, toxicity, action, side effects and more

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2D Structure
Also known as: Cynarin, 30964-13-7, Cinarine, 1,5-dicaffeoylquinic acid, 1,3-dicaffeoylquinic acid, Cynarine [inn]
Molecular Formula
C25H24O12
Molecular Weight
516.4  g/mol
InChI Key
YDDUMTOHNYZQPO-RVXRWRFUSA-N
FDA UNII
85D81U9JAV

cynarine is a natural product found in Saussurea involucrata, Helichrysum italicum, and other organisms with data available.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(1R,3R,4S,5R)-1,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic acid
2.1.2 InChI
InChI=1S/C25H24O12/c26-15-5-1-13(9-17(15)28)3-7-21(31)36-20-12-25(24(34)35,11-19(30)23(20)33)37-22(32)8-4-14-2-6-16(27)18(29)10-14/h1-10,19-20,23,26-30,33H,11-12H2,(H,34,35)/b7-3+,8-4+/t19-,20-,23+,25-/m1/s1
2.1.3 InChI Key
YDDUMTOHNYZQPO-RVXRWRFUSA-N
2.1.4 Canonical SMILES
C1C(C(C(CC1(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)OC(=O)C=CC3=CC(=C(C=C3)O)O)O)O
2.1.5 Isomeric SMILES
C1[C@H]([C@@H]([C@@H](C[C@]1(C(=O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)OC(=O)/C=C/C3=CC(=C(C=C3)O)O)O)O
2.2 Other Identifiers
2.2.1 UNII
85D81U9JAV
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1,5-dicaffeoylquinic Acid

2. 1-carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate)

3. Cinarin

4. Cinarina

5. Cinarine

6. Cynarex

7. Cynarin

8. Cynarin, (1alpha,3alpha,4alpha,5beta)-isomer

9. Cynarix

10. Listricol

11. Listrocol

12. Nivellipid

13. Phemocil

2.3.2 Depositor-Supplied Synonyms

1. Cynarin

2. 30964-13-7

3. Cinarine

4. 1,5-dicaffeoylquinic Acid

5. 1,3-dicaffeoylquinic Acid

6. Cynarine [inn]

7. Cynarine [mi]

8. Plemocil

9. (1r,3r,4s,5r)-1,3-bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexanecarboxylic Acid

10. Cynarine [mart.]

11. 212891-05-9

12. Cynarine [who-dd]

13. 1,3-dicqa

14. Chebi:520

15. 85d81u9jav

16. Cinarin

17. 1884-23-7

18. Caffeic Acid 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene Ester

19. 1-carboxy-4,5-dihydroxy-1,3-cyclohexylenebis-(3,4-dihydroxycinnamate)

20. (1r,3r,4s,5r)-1,3-bis[[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]-4,5-dihydroxycyclohexane-1-carboxylic Acid

21. 1,5-di-o-caffeoylquinic Acid

22. Phemocil

23. 3,4-dihydroxycinnamic Acid 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene Ester

24. 3,4-dihydroxycinnamic Acid, 1-carboxy-4,5-dihydroxy-1,3-cyclohexylene Ester

25. (1r,3r,4s,5r)-1,3-bis(((e)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexane-1-carboxylic Acid

26. (1r,3r,4s,5r)-1,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-4,5-dihydroxycyclohexanecarboxylic Acid

27. (1r,3r,4s,5r)-1,3-bis({[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy})-4,5-dihydroxycyclohexane-1-carboxylic Acid

28. 1,3-dicaffeoylquinic Acid (constituent Of Echinacea Angustifolia Root, Echinacea Pallida Root, Echinacea Purpurea Root And Echinacea Purpurea Aerial Parts) [dsc]

29. Cyclohexanecarboxylic Acid, 1,3-bis(((2e)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-4,5-dihydroxy-, (1r,3r,4s,5r)-

30. 1,5-dicaffeoylqunic Acid

31. Unii-85d81u9jav

32. Cynaricine

33. Quinic Acid 1,5-dicaffeic Ester

34. Cynarin, Analytical Standard

35. Schembl42528

36. 1_5_dihydrocaffeoylquinic_acid

37. Chembl487258

38. Dtxsid301309674

39. Bcp29379

40. Hy-n0359

41. Zinc4098728

42. Bdbm50369484

43. S3301

44. Akos015912727

45. Ac-6022

46. Cs-6280

47. As-74959

48. N2812

49. 1,3-dicaffeoylquinic Acid, >=98% (hplc)

50. A820670

51. J-003723

52. Q-100389

53. Q1763092

54. Cynarine;1,3-dicaffeoylquinic Acid;1,5-dqa;1,5-dicaffeoylquinic Acid

55. (1r,3r,4s,5r)-1,3-bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-4,5-dihydroxycyclohexanecarboxylicacid

56. (1r,3r,4s,5r)-1,3-bis{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-4,5-dihydroxycyclohexane-1-carboxylic Acid

57. (1r-(1.alpha.,3.alpha.,4.alpha.,5.beta.))-1,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-4,5-dihydroxycyclohexanecarboxylic Acid

58. (1r-(1alpha,3alpha,4alpha,5beta))-1,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-4,5-dihydroxycyclohexanecarboxylic Acid

59. 1,3beta-bis[(e)-3-(3,4-dihydroxyphenyl)acryloyloxy]-4beta,5alpha-dihydroxycyclohexane-1alpha-carboxylic Acid

60. Cyclohexanecarboxylic Acid, 1,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-4,5-dihydroxy-

61. Cyclohexanecarboxylic Acid,1,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-4,5-dihydroxy-,(1r,3r,4s,5r)-

2.4 Create Date
2005-06-24
3 Chemical and Physical Properties
Molecular Weight 516.4 g/mol
Molecular Formula C25H24O12
XLogP31.5
Hydrogen Bond Donor Count7
Hydrogen Bond Acceptor Count12
Rotatable Bond Count9
Exact Mass516.12677620 g/mol
Monoisotopic Mass516.12677620 g/mol
Topological Polar Surface Area211 Ų
Heavy Atom Count37
Formal Charge0
Complexity887
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count2
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Pharmacology and Biochemistry
4.1 MeSH Pharmacological Classification

Cholagogues and Choleretics

Gastrointestinal agents that stimulate the flow of bile into the duodenum (cholagogues) or stimulate the production of bile by the liver (choleretic). (See all compounds classified as Cholagogues and Choleretics.)


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