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Chemistry

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Also known as: Egcg, 989-51-5, Epigallocatechin gallate, Epigallocatechin 3-gallate, Tea catechin, Epigallocatechin-3-gallate

Molecular Formula

C₂₂H₁₈O₁₁

Molecular Weight

458.4 g/mol

InChI Key

WMBWREPUVVBILR-WIYYLYMNSA-N

FDA UNII

BQM438CTEL

Epigallocatechin Gallate is a phenolic antioxidant found in a number of plants such as green and black tea. It inhibits cellular oxidation and prevents free radical damage to cells. It is under study as a potential cancer chemopreventive agent. (NCI)

1 2D Structure

Green Tea Extract

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(2R,3R)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate

2.1.2 InChI

InChI=1S/C22H18O11/c23-10-5-12(24)11-7-18(33-22(31)9-3-15(27)20(30)16(28)4-9)21(32-17(11)6-10)8-1-13(25)19(29)14(26)2-8/h1-6,18,21,23-30H,7H2/t18-,21-/m1/s1

2.1.3 InChI Key

WMBWREPUVVBILR-WIYYLYMNSA-N

2.1.4 Canonical SMILES

C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O

2.1.5 Isomeric SMILES

C1[C@H]([C@H](OC2=CC(=CC(=C21)O)O)C3=CC(=C(C(=C3)O)O)O)OC(=O)C4=CC(=C(C(=C4)O)O)O

2.2 Other Identifiers

2.2.1 UNII

BQM438CTEL

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Egcg Cpd

2. Epigallo-catechin Gallate

3. Epigallocatechin Gallate

4. Epigallocatechin-3-gallate

5. Epigallocatechin-3-o-gallate

2.3.2 Depositor-Supplied Synonyms

1. Egcg

2. 989-51-5

3. Epigallocatechin Gallate

4. Epigallocatechin 3-gallate

5. Tea Catechin

6. Epigallocatechin-3-gallate

7. (-)-epigallocatechin-3-o-gallate

8. Teavigo

9. Epigallocatechin-3-monogallate

10. (-)-epigallocatechin 3-gallate

11. (-)-epigallocatechol Gallate

12. Catechin Deriv.

13. Pf-egcg 90

14. Green Tea Extract

15. (2r,3r)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl 3,4,5-trihydroxybenzoate

16. Nvp-xaa 723

17. Bqm438ctel

18. (2r,3r)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-chromen-3-yl 3,4,5-trihydroxybenzoate

19. [(2r,3r)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-chromen-3-yl] 3,4,5-trihydroxybenzoate

20. Chebi:4806

21. Chembl297453

22. [(2r,3r)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl] 3,4,5-trihydroxybenzoate

23. Dsstox_cid_567

24. Dsstox_rid_78830

25. Dsstox_gsid_29889

26. (2r,3r)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

27. Benzoic Acid, 3,4,5-trihydroxy-, (2r,3r)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2h-1-benzopyran-3-yl Ester

28. Cas-989-51-5

29. Smr000449288

30. Ccris 3729

31. Sr-01000759328

32. Unii-bqm438ctel

33. L-epigallocatechin Gallate

34. Epigallocate

35. Epigalocatechin Gallate

36. (-)-egcg

37. Epigallocic Acid

38. Teatannin Ii

39. 2kdh

40. 3oob

41. 4awm

42. (-)-cis-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-1(2h)-benzopyran-3,5,7-triol 3-gallate

43. (-)-epigallocatechin 3-o-gallate

44. Kdh

45. Epigallocatechol, 3-gallate, (-)-

46. (-)-epigallocatechin Gallate (egcg)

47. Epigallocatcchin Gallate

48. Epigallocatechin-gallate

49. Epigallocatechol Gallate

50. Spectrum_000316

51. Specplus_000277

52. Spectrum2_000168

53. Spectrum3_000244

54. Spectrum4_001541

55. Spectrum5_000102

56. Galloyl-l-epigallocatechol

57. Egcg [who-dd]

58. Egcg [mi]

59. 3-o-galloylepigallocatechin

60. (-)-epigallocatechin Gallat

61. (-)-epigallocatehin Gallate

62. Schembl35258

63. Bspbio_001628

64. Epigallocatechin-gallate-(-)

65. Kbiogr_002002

66. Kbioss_000796

67. Spectrum210239

68. Cid_65064

69. Mls000758300

70. Mls001424000

71. Divk1c_006373

72. Spbio_000035

73. Epigallocatechin Monogallate, B

74. Gtpl7002

75. Megxp0_001166

76. Dtxsid1029889

77. Acon1_001054

78. Kbio1_001317

79. Kbio2_000796

80. Kbio2_003364

81. Kbio2_005932

82. Kbio3_001128

83. (-)-cis-3,3',4',5,5',7-hexahydroxy-flavane-3-gallate

84. Hms2051k21

85. Hms3649e08

86. 3-o-galloyl-(-)-epigallocatechin

87. Zinc3870412

88. Epigallocatechin 3-o-gallate

89. Tox21_201468

90. Tox21_303457

91. Bdbm50070942

92. Ccg-38378

93. Fr-109

94. Lmpk12030005

95. S2250

96. Akos015918182

97. Cs-1258

98. Db12116

99. Ds-9030

100. Epigallocatechin Gallate [inci]

101. Nc00078

102. Sdccgmls-0066550.p001

103. (-)-epigallocatechin Gallate, >=95%

104. (-)-epigallocatechin-3-gallate; Egcg

105. Ncgc00164319-01

106. Ncgc00164319-02

107. Ncgc00164319-03

108. Ncgc00164319-04

109. Ncgc00164319-06

110. Ncgc00257243-01

111. Ncgc00259019-01

112. (-)-epigallocatechin Gallate (85% (-)-epigallocatechin Gallate, 10% (-)-epigallocatechin, 5% (-)- Epicatechin Gallate)

113. Ac-34075

114. Bp-30205

115. Hy-13653

116. E0694

117. N1874

118. Sw197458-3

119. C09731

120. M01719

121. (-)-epigallocatechin Gallate, >=97.0% (hplc)

122. (-)-epigallocatechin Gallate, Analytical Standard

123. 989e515

124. A845931

125. Gallic Acid, 3-ester With Epigallocatechol, (-)-

126. Q393339

127. Sr-01000946601

128. (-)-epigallocatechin-3-o-gallate [usp-rs]

129. Q-100914

130. Sr-01000759328-5

131. Sr-01000759328-6

132. Sr-01000946601-1

133. Epigallocatechin-3-gallate 1000 Microg/ml In Acetonitrile

134. (-)-epigallocatechin Gallate, >=80% (hplc), From Green Tea

135. Epigallocatechin Gallate, Primary Pharmaceutical Reference Standard

136. (-)-epigallocatechin-3-o-gallate, United States Pharmacopeia (usp) Reference Standard

137. (2r,3r)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl3,4,5-trihydroxybenzoate

138. [5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)chroman-3-yl] 2,3,4-trihydroxybenzoate

139. Epigallocatechin Gallate, Pharmaceutical Secondary Standard; Certified Reference Material

140. (-)-cis-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-1(2h)-benzopyran-3-yl Gallate

141. (-)-epigallocatechin Gallate (85% (-)-epigallocatechin Gallate, 10% (-)-epigallocatechin, 5% (-)-epicatechin Gallate)

142. (-)-epigallocatechin-3-o-gallate (egcg) (constituent Of Powdered Decaffeinated Green Tea Extract) [dsc]

143. (2r,3r)-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2h-chromen-3-yl-3,4,5-trihydroxybenzoate

144. 3,4,5-trihydroxybenzoic Acid (2r,3r)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2h-1-benzopyran-3-yl Ester

145. 3,4-dihydro-5,7-dihydroxy-2r-(3,4,5-trihydroxyphenyl)-2h-1-benzopyran-3r-yl-3,4,5-trihydroxybenzoate

146. Benzoic Acid, 3,4,5-trihydroxy-, 3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2h-1-benzopyran-3-yl Ester, (2r-cis)-

147. Benzoic Acid, 3,4,5-trihydroxy-,(2r,3r)-3,4-dihydro-5,7-dihydroxy-2-(3,4,5-trihydroxyphenyl)-2h-1-benzopyran-3-yl Ester

2.4 Create Date

2005-06-24

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₁₈O₁₁
Molecular Weight	458.4 g/mol
XLogP3	1.2
Hydrogen Bond Donor Count	8
Hydrogen Bond Acceptor Count	11
Rotatable Bond Count	4
Exact Mass	458.08491139 g/mol
Monoisotopic Mass	458.08491139 g/mol
Topological Polar Surface Area	197 Å²
Heavy Atom Count	33
Formal Charge	0
Complexity	667
Isotope Atom Count	0
Defined Atom Stereocenter Count	2
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

Anticarcinogenic Agents

Agents that reduce the frequency or rate of spontaneous or induced tumors independently of the mechanism involved. (See all compounds classified as Anticarcinogenic Agents.)

Neuroprotective Agents

Drugs intended to prevent damage to the brain or spinal cord from ischemia, stroke, convulsions, or trauma. Some must be administered before the event, but others may be effective for some time after. They act by a variety of mechanisms, but often directly or indirectly minimize the damage produced by endogenous excitatory amino acids. (See all compounds classified as Neuroprotective Agents.)

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.)

Antimutagenic Agents

Agents that reduce the frequency or rate of spontaneous or induced mutations independently of the mechanism involved. (See all compounds classified as Antimutagenic Agents.)

4.2 Metabolism/Metabolites

(-)-Epigallocatechin gallate has known human metabolites that include (-)-Epigallocatechin gallate, 3p-hydroxy-glucuronide and (-)-Epigallocatechin gallate, 4p-hydroxy-glucuronide.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

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