Berberine Hydrochloride

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Also known as: Berberine hydrochloride, 633-65-8, Natural yellow 18, Berberinium chloride, Benzodioxide, Berberine hcl

Molecular Formula

C₂₀H₁₈ClNO₄

Molecular Weight

371.8 g/mol

InChI Key

VKJGBAJNNALVAV-UHFFFAOYSA-M

FDA UNII

UOT4O1BYV8

Berberine Chloride is the orally bioavailable, hydrochloride salt form of berberine, a quaternary ammonium salt of an isoquinoline alkaloid and active component of various Chinese herbs, with potential antineoplastic, radiosensitizing, anti-inflammatory, anti-lipidemic and antidiabetic activities. Although the mechanisms of action through which berberine exerts its effects are not yet fully elucidated, upon administration this agent appears to suppress the activation of various proteins and/or modulate the expression of a variety of genes involved in tumorigenesis and inflammation, including, but not limited to transcription factor nuclear factor-kappa B (NF-kB), myeloid cell leukemia 1 (Mcl-1), B-cell lymphoma 2 (Bcl-2), B-cell lymphoma-extra large (Bcl-xl), cyclooxygenase (COX)-2, tumor necrosis factor (TNF), interleukin (IL)-6, IL-12, inducible nitric oxide synthase (iNOS), intercellular adhesion molecule-1 (ICAM-1), E-selectin, monocyte chemoattractant protein-1 (MCP-1), C-X-C motif chemokine 2 (CXCL2), cyclin D1, activator protein (AP-1), hypoxia-inducible factor 1 (HIF-1), signal transducer and activator of transcription 3 (STAT3), peroxisome proliferator-activated receptor (PPAR), arylamine N-acetyltransferase (NAT), and DNA topoisomerase I and II. The modulation of gene expression may induce cell cycle arrest and apoptosis, and inhibit cancer cell proliferation. In addition, berberine modulates lipid and glucose metabolism.

1 2D Structure

2D Structure

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene;chloride

2.1.2 InChI

InChI=1S/C20H18NO4.ClH/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2;/h3-4,7-10H,5-6,11H2,1-2H3;1H/q+1;/p-1

2.1.3 InChI Key

VKJGBAJNNALVAV-UHFFFAOYSA-M

2.1.4 Canonical SMILES

COC1=C(C2=C[N+]3=C(C=C2C=C1)C4=CC5=C(C=C4CC3)OCO5)OC.[Cl-]

2.2 Other Identifiers

2.2.1 UNII

UOT4O1BYV8

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Barberry Root

2. Barberry Root Extract

3. Berberidis Radix

4. Berberidis Radix Extract

5. Berberis Wilsoniae Root

6. Berberis Wilsoniae Root Extract

7. Sankezhen

2.3.2 Depositor-Supplied Synonyms

1. Berberine Hydrochloride

2. 633-65-8

3. Natural Yellow 18

4. Berberinium Chloride

5. Benzodioxide

6. Berberine Hcl

7. Berberine (chloride)

8. Berberinum

9. Nsc-163088

10. Berberin Hydrochloride

11. 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-ium Chloride

12. Mfcd00011939

13. Uot4o1byv8

14. Nsc-646666

15. Mls002702530

16. Natural Yellow 18 (chloride)

17. Chebi:31271

18. Nsc163088

19. 633-65-8 (chloride)

20. Dsstox_cid_4602

21. Berbinium, 7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)-, Chloride

22. 5,6-dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium Chloride

23. Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-, Chloride

24. Dsstox_rid_77465

25. Dsstox_gsid_24602

26. Berberinium Chloride Hydrate

27. Chembl12089

28. Berberine Chloride [jan]

29. Gnf-pf-4545

30. 16,17-dimethoxy-5,7-dioxa-13$l^{5}-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(13),2,4(8),9,14,16,18,20-octaen-13-ylium Chloride

31. Smr001233240

32. Nsc646666

33. Berberine Chloride Form

34. Sr-01000711827

35. Ncgc00016526-02

36. Ncgc00016526-07

37. Cas-633-65-8

38. Einecs 211-195-9

39. Unii-uot4o1byv8

40. Nsc 163088

41. Berberine Chloride, Primary Pharmaceutical Reference Standard

42. Ai3-61834

43. Ccris 8656

44. 5,6-dihydro-9,10-dimethoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium Chloride

45. Prestwick_91

46. Barberry Root Extract

47. Nsc 646666

48. Dimethoxy[?] Chloride

49. Berberine Chloride (tn)

50. Berberinum [hpus]

51. Berberine Hydrochloride,(s)

52. Mls002153890

53. Schembl153906

54. Spectrum1500811

55. Dtxsid8024602

56. Hms500n07

57. Chebi: 16118

58. Hms1569f14

59. Hms1921i18

60. Hms2096f14

61. Hms2210a06

62. Hms2235h16

63. Hms3336c05

64. Hms3373l14

65. Hms3655f20

66. Pharmakon1600-01500811

67. Berberine Chloride [usp-rs]

68. Tox21_110474

69. Tox21_200348

70. Ac-118

71. Ccg-39622

72. Nsc757795

73. S2271

74. Akos007930622

75. Tox21_110474_1

76. Cs-3214

77. Ks-5294

78. Nsc-757795

79. 5,6-dihydro-9,10-dimethoxybenzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium Chloride Hydrate

80. Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium,5,6-dihydro-9,10-dimethoxy-, Chloride

81. Berberine Hydrochloride [who-dd]

82. Ncgc00091896-01

83. Ncgc00094858-01

84. Ncgc00094858-02

85. Ncgc00257902-01

86. 16,17-dimethoxy-5,7-dioxa-13-azoniapentacyclo[11.8.0.02,10.04,8.015,20]henicosa-1(13),2,4(8),9,14,16,18,20-octaene;chloride

87. Hy-18258

88. Sy076593

89. Cas: 638-65-8

90. B0450

91. Ft-0622874

92. N1699

93. Sw196403-2

94. A834344

95. Berberine Chloride Hydrate, Technical, >=90% (at)

96. Q-100261

97. Q-100731

98. Sr-01000711827-4

99. Sr-01000711827-6

100. Z2768724441

101. Berberine Chloride, British Pharmacopoeia (bp) Reference Standard

102. Berberine Chloride, European Pharmacopoeia (ep) Reference Standard

103. Benzo[g]-1,6-a]quinolizinium, 5,6-dihydro-9,10-dimethoxy-, Chloride

104. Berberine Chloride, United States Pharmacopeia (usp) Reference Standard

105. 5,6-dihydro-9,10-dimethoxy-1,3-benzodioxolo[5,6-a]benzo[g]quinolizinium Chloride (1:1)

106. Berberine Chloride, Pharmaceutical Secondary Standard; Certified Reference Material

107. Berbinium,8,13,13a-tetradehydro-9.10-dimethoxy-2,3-(methylene Dioxy)-, Chloride

108. 16,17-dimethoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2(10),3,8,13,15(20),16,18-octaen-13-ylium Chloride

109. 9,10-dimethoxy-5,6-dihydro-[1,3]dioxolo[4,5-g]isoquinolino[3,2-a]isoquinolin-7-iumchloride

110. Benzo(g)-1,3-benzodioxolo(5,6-a)quinolizinium, 5,6-dihydro-9,10-dimethoxy-, Chloride (1:1)

2.4 Create Date

2005-03-26

3 Chemical and Physical Properties

Molecular Formula	C₂₀H₁₈ClNO₄
Molecular Weight	371.8 g/mol
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	2
Exact Mass	371.0924357 g/mol
Monoisotopic Mass	371.0924357 g/mol
Topological Polar Surface Area	40.8 Å²
Heavy Atom Count	26
Formal Charge	0
Complexity	488
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	2

Berberine Hydrochloride

Berberine Hydrochloride

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