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Chemistry

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Also known as: Cichoric acid, L-chicoric acid, 70831-56-0, 6537-80-0, (-)-chicoric acid, Dicaffeoyltartaric acid
Molecular Formula
C22H18O12
Molecular Weight
474.4  g/mol
InChI Key
YDDGKXBLOXEEMN-IABMMNSOSA-N
FDA UNII
S4YY3V8YHD

Cichoric Acid
cichoric acid is a natural product found in Cichorium intybus, Hydrastis canadensis, and other organisms with data available.
1 2D Structure

Cichoric Acid

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2R,3R)-2,3-bis[[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic acid
2.1.2 InChI
InChI=1S/C22H18O12/c23-13-5-1-11(9-15(13)25)3-7-17(27)33-19(21(29)30)20(22(31)32)34-18(28)8-4-12-2-6-14(24)16(26)10-12/h1-10,19-20,23-26H,(H,29,30)(H,31,32)/b7-3+,8-4+/t19-,20-/m1/s1
2.1.3 InChI Key
YDDGKXBLOXEEMN-IABMMNSOSA-N
2.1.4 Canonical SMILES
C1=CC(=C(C=C1C=CC(=O)OC(C(C(=O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)C(=O)O)O)O
2.1.5 Isomeric SMILES
C1=CC(=C(C=C1/C=C/C(=O)O[C@@H](C(=O)O)[C@@H](OC(=O)/C=C/C2=CC(=C(C=C2)O)O)C(=O)O)O)O
2.2 Other Identifiers
2.2.1 UNII
S4YY3V8YHD
2.3 Synonyms
2.3.1 MeSH Synonyms

1. (-)-chicoric Acid

2. (-)-l-chicoric Acid

3. (2r,3r)-2,3-bis(((2e)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-butanedioic Acid

4. Cichoric Acid

5. Dicaffeoyltartaric Acid

6. L-chicoric Acid

2.3.2 Depositor-Supplied Synonyms

1. Cichoric Acid

2. L-chicoric Acid

3. 70831-56-0

4. 6537-80-0

5. (-)-chicoric Acid

6. Dicaffeoyltartaric Acid

7. L-cichoric Acid

8. (2r,3r)-2,3-bis[[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic Acid

9. (-)-l-chicoric Acid

10. Nsc 699173

11. L-dcta

12. Chicoric Acid, (-)-

13. Nsc699173

14. S4yy3v8yhd

15. Dicaffeoyl-l-tartaric Acid

16. Trans-caffeoyltartaric Acid

17. Chebi:3594

18. Chembl282731

19. 2,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)butanedioic Acid

20. (r-(r*,r*-(e,e)))-2,3-bis((3-(3,4-dihydroxphenyl)-1-oxo-2-propenyl)oxy)butanedioic Acid

21. Nsc-699173

22. (2r,3r)-2,3-bis(((e)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)succinic Acid

23. (2r,3r)-2,3-bis[[(e)-3-(3,4-dihydroxyphenyl)acryloyl]oxy]succinic Acid

24. Chicoricacid

25. (2r,3r)-2,3-bis{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic Acid

26. Butanedioic Acid, 2,3-bis[[(2e)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (2r,3r)-

27. Unii-s4yy3v8yhd

28. L-chicoricacid

29. 1-chicoricacid

30. Cichoric-acid

31. L-chicoric-acid

32. Gkp

33. ( ?)-chicoric Acid

34. Ech Purpurea Pe

35. Echinacea Purpurea Powder

36. L-ca

37. Ech Angustifolia Pe

38. Dsstox_cid_13332

39. Dsstox_rid_79064

40. Dsstox_gsid_33332

41. Echinacea Purpurea Root Extract

42. Chicoric Acid [usp-rs]

43. Dtxsid0033332

44. Schembl15532218

45. Chicoric Acid, >=95% (hplc)

46. Hy-n0457

47. Zinc4098726

48. Tox21_201055

49. Bdbm50076273

50. Mfcd00189418

51. S9133

52. Akos000278435

53. Ccg-269487

54. Cs-4262

55. Butanedioic Acid, 2,3-bis(((2e)-3-(3,4-dihydroxphenyl)-1-oxo-2-propenyl)oxy)-, (2r,3r)-

56. ( -)-chicoric Acid, Analytical Standard

57. Ncgc00091914-01

58. Ncgc00091914-02

59. Ncgc00091914-04

60. Ncgc00258608-01

61. Ac-34315

62. Ac-36990

63. As-56447

64. Butanedioic Acid, 2,3-bis((3-(3,4-dihydroxphenyl)-1-oxo-2-propenyl)oxy)-, (r-(r*,r*-(e,e)))-

65. Cas-70831-56-0

66. C3450

67. 831c560

68. A914269

69. Q5119402

70. Tartaric Acid, Bis(3,4-dihydroxycinnamate)

71. 2,3-bis[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]butanedioic Acid

72. Chicoric Acid, United States Pharmacopeia (usp) Reference Standard

73. (2r,3r)-2,3-bis((3-(3,4-dihydroxyphenyl)acryloyl)oxy)succinic Acid

74. (2r,3r)-2,3-bis((e)-3-(3,4-dihydroxyphenyl)acryloyloxy)succinic Acid

75. (2r,3r)-2,3-bis-[(e)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-succinic Acid

76. (2r,3r)-2,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]butanedioic Acid

77. (2r,3r)-2,3-bis{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}succinic Acid

78. (2r,3r)-2,3-bis{[3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}butanedioic Acid

79. [s-(r*,r*)]-2,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]butanedioic Acid

80. Butanedioic Acid, 2,3-bis(((2e)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-, (2r,3r)-

81. Butanedioic Acid, 2,3-bis((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-, (r-(r*,r*))-

82. Butanedioic Acid, 2,3-bis[[(2e)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, (2r,3r)- (9ci)

83. Butanedioic Acid, 2,3-bis[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-, [r-[r*,r*-(e,e)]]-

84. Chicoric Acid (constituent Of Echinacea Angustifolia Root, Echinacea Pallida Root, Echinacea Purpurea Root And Echinacea Purpurea Aerial Parts) [dsc]

85. Ncgc00091914-04!(2r,3r)-2,3-bis[[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy]butanedioic Acid

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 474.4 g/mol
Molecular Formula C22H18O12
XLogP32
Hydrogen Bond Donor Count6
Hydrogen Bond Acceptor Count12
Rotatable Bond Count11
Exact Mass474.07982601 g/mol
Monoisotopic Mass474.07982601 g/mol
Topological Polar Surface Area208 Ų
Heavy Atom Count34
Formal Charge0
Complexity740
Isotope Atom Count0
Defined Atom Stereocenter Count2
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

HIV Integrase Inhibitors

Inhibitors of HIV INTEGRASE, an enzyme required for integration of viral DNA into cellular DNA. (See all compounds classified as HIV Integrase Inhibitors.)


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