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Baicalein

Synopsis, Chemistry

ANALYTICAL SOLUTION(s)

4 Other Ref. Standards

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Also known as: 491-67-8, 5,6,7-trihydroxyflavone, Noroxylin, 5,6,7-trihydroxy-2-phenyl-4h-chromen-4-one, 5,6,7-trihydroxy-2-phenylchromen-4-one, Baikalein

Molecular Formula

C₁₅H₁₀O₅

Molecular Weight

270.24 g/mol

InChI Key

FXNFHKRTJBSTCS-UHFFFAOYSA-N

FDA UNII

49QAH60606

Sho-Saiko-To is a botanical formulation with potential chemopreventive activities. Sho-Saiko-to, an herbal mixture, contains seven herbal extracts whose mechanism of action if not fully understood. There is evidence of antiproliferative effects against hepatocellular carcinoma in vitro. Other effects of this agent described in animal models include the prevention of liver injury and hepatocyte-regenerating activity. Antitumor effects associated with this herbal product may include induction of apoptosis, cell cycle arrest at the G0/G1 phase, and activation of an immune response, characterized by the release of cytokines as well as activation of effector cells, such as macrophages and natural killer cells.

1 2D Structure

Baicalein

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

5,6,7-trihydroxy-2-phenylchromen-4-one

2.1.2 InChI

InChI=1S/C15H10O5/c16-9-6-11(8-4-2-1-3-5-8)20-12-7-10(17)14(18)15(19)13(9)12/h1-7,17-19H

2.1.3 InChI Key

FXNFHKRTJBSTCS-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C(C=C1)C2=CC(=O)C3=C(O2)C=C(C(=C3O)O)O

2.2 Other Identifiers

2.2.1 UNII

49QAH60606

2.3 Synonyms

2.3.1 Depositor-Supplied Synonyms

1. 491-67-8

2. 5,6,7-trihydroxyflavone

3. Noroxylin

4. 5,6,7-trihydroxy-2-phenyl-4h-chromen-4-one

5. 5,6,7-trihydroxy-2-phenylchromen-4-one

6. Baikalein

7. Baicelein

8. Mfcd00017459

9. 5,6,7-trihydroxy-2-phenyl-chromen-4-one

10. 4h-1-benzopyran-4-one, 5,6,7-trihydroxy-2-phenyl-

11. Nsc661431

12. Nsc-661431

13. Chembl8260

14. Chebi:2979

15. 5,6,7-trihydroxy-2-phenyl-4h-1-benzopyran-4-one

16. 49qah60606

17. 5,7-trihydroxyflavone

18. Biacalein

19. Sho-saiko-to

20. Smr000112462

21. Sr-01000597499

22. Nsc 661431

23. Unii-49qah60606

24. Baicalein, 8

25. Baicalein,(s)

26. 3wl

27. Baicalein, 14

28. Baicalein, 98%

29. Spectrum_000427

30. Tocris-1761

31. Specplus_000758

32. Baicalein [mi]

33. Baicalein [inci]

34. Spectrum2_000466

35. Spectrum3_001608

36. Spectrum4_000537

37. Spectrum5_001418

38. Baicalein [usp-rs]

39. Baicalein [who-dd]

40. Oprea1_765614

41. Bspbio_003215

42. Kbiogr_001173

43. Kbioss_000907

44. Mls002473007

45. Mls006011756

46. Bidd:er0121

47. Divk1c_006854

48. Schembl139617

49. Spectrum1504002

50. Spbio_000572

51. Gtpl5144

52. Dtxsid2022389

53. Kbio1_001798

54. Kbio2_000907

55. Kbio2_003475

56. Kbio2_006043

57. Kbio3_002435

58. Hms1922o22

59. Hms2267f15

60. Hms3268c22

61. Hms3412f14

62. Hms3649o19

63. Hms3655p18

64. Hms3676f14

65. Albb-028286

66. Bcp14393

67. Hy-n0196

68. Tnp00121

69. Zinc3871633

70. Bbl027840

71. Bdbm50009001

72. Ccg-38705

73. Lmpk12111095

74. Nsc729192

75. S2268

76. Stl146746

77. Akos005747014

78. Ac-7991

79. Cs-6159

80. Nsc-729192

81. Sdccgmls-0066744.p001

82. Baicalein, Analytical Reference Material

83. Smp1_000037

84. Ncgc00017236-01

85. Ncgc00017236-02

86. Ncgc00017236-03

87. Ncgc00017236-04

88. Ncgc00017236-05

89. Ncgc00017236-06

90. Ncgc00017236-07

91. Ncgc00017236-08

92. Ncgc00017236-10

93. Ncgc00017236-11

94. Ncgc00025282-01

95. Ncgc00025282-02

96. Ncgc00025282-03

97. Ncgc00025282-04

98. Ncgc00178204-01

99. As-57923

100. Sy057137

101. 5,6,7-trihydroxy-2-phenyl-chroman-4-one

102. Ft-0622548

103. N1858

104. Sw219229-1

105. T2721

106. S00113

107. 491b678

108. 5,7-trihydroxy-2-phenyl-4h-1-benzopyran-4-one

109. A827663

110. Q-100550

111. Q2879363

112. Sr-01000597499-1

113. Sr-01000597499-3

114. Sr-01000597499-4

115. Sr-01000597499-6

116. W-202870

117. 5,6,7-trihydroxy-2-phenyl-(4h)-1-benzopyran-4-one

118. Brd-k72327355-001-02-2

119. Brd-k72327355-001-06-3

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₅H₁₀O₅
Molecular Weight	270.24 g/mol
XLogP3	1.7
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	1
Exact Mass	270.05282342 g/mol
Monoisotopic Mass	270.05282342 g/mol
Topological Polar Surface Area	87 Å²
Heavy Atom Count	20
Formal Charge	0
Complexity	413
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	1

4 Pharmacology and Biochemistry

4.1 MeSH Pharmacological Classification

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.)

Enzyme Inhibitors

Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

Prostaglandin Antagonists

Compounds that inhibit the action of prostaglandins. (See all compounds classified as Prostaglandin Antagonists.)