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    epicatechin gallate

    DIGITAL CONTENT

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    2D Structure
    Also known as: 1257-08-5, Epicatechin gallate, (-)-epicatechin-3-o-gallate, (-)-epicatechingallate, (-)-epicatechin-3-gallate, L-epicatechin gallate
    Molecular Formula
    C22H18O10
    Molecular Weight
    442.4  g/mol
    InChI Key
    LSHVYAFMTMFKBA-TZIWHRDSSA-N
    FDA UNII
    92587OVD8Z
    epicatechin gallate is a natural product found in Scurrula atropurpurea, Acacia omalophylla, and other organisms with data available.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(2R,3R)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-chromen-3-yl] 3,4,5-trihydroxybenzoate
    2.1.2 InChI
    InChI=1S/C22H18O10/c23-11-6-14(25)12-8-19(32-22(30)10-4-16(27)20(29)17(28)5-10)21(31-18(12)7-11)9-1-2-13(24)15(26)3-9/h1-7,19,21,23-29H,8H2/t19-,21-/m1/s1
    2.1.3 InChI Key
    LSHVYAFMTMFKBA-TZIWHRDSSA-N
    2.1.4 Canonical SMILES
    C1C(C(OC2=CC(=CC(=C21)O)O)C3=CC(=C(C=C3)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)OC(=O)C4=CC(=C(C(=C4)O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    92587OVD8Z
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Epicatechin Gallate

    2. Epicatechin Gallate, (2r-cis)-isomer

    3. Epicatechin-3-gallate

    4. Epicatechin-3-galloyl Ester

    5. Epicatechin-3-o-gallate

    2.3.2 Depositor-Supplied Synonyms

    1. 1257-08-5

    2. Epicatechin Gallate

    3. (-)-epicatechin-3-o-gallate

    4. (-)-epicatechingallate

    5. (-)-epicatechin-3-gallate

    6. L-epicatechin Gallate

    7. Epicatechin Monogallate

    8. Teatannin

    9. (-)-epicatechin 3-o-gallate

    10. Ecg

    11. Epicatechol, Gallate

    12. 3-o-galloylepicatechin

    13. (-)-cis-3,3',4',5,7-pentahydroxyflavane 3-gallate

    14. [(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-chromen-3-yl] 3,4,5-trihydroxybenzoate

    15. 3-gallate(-)-epicatechol

    16. (-)-epicatechin 3-gallate

    17. Chembl36327

    18. Epicatechin-3-o-gallate

    19. Chebi:70255

    20. 92587ovd8z

    21. Epicatechin-3-galloyl Ester

    22. (2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl 3,4,5-trihydroxybenzoate

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

    24. Epicatechin 3-gallate

    25. Epi-catechin 3-o-gallate

    26. Epicatechin Gallate, (2r-cis)-isomer

    27. Nsc 636594

    28. Unii-92587ovd8z

    29. Nsc636594

    30. (2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-chromen-3-yl 3,4,5-trihydroxybenzoate

    31. Epicatechol, 3-gallate, (-)-

    32. Nsc-636594

    33. Mfcd00075936

    34. (-)epicatechingallate

    35. Spectrum_000314

    36. L-ecg

    37. Specplus_000275

    38. (-) Epicatechin Gallate

    39. Epicatechin-gallate-(-)

    40. Spectrum2_000165

    41. Spectrum3_000246

    42. Spectrum4_001540

    43. Spectrum5_000080

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

    45. (?)-epicatechin 3-gallate

    46. Schembl39047

    47. Bspbio_001632

    48. Epicatechol 3-gallate

    49. Kbiogr_001980

    50. Kbioss_000794

    51. Spectrum210238

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

    53. Divk1c_006371

    54. Epicatechingallate, L-

    55. Spbio_000029

    56. (-)epicatechin Gallate

    57. Megxp0_000810

    58. Epicatechin 3-o-gallate

    59. Kbio1_001315

    60. Kbio2_000794

    61. Kbio2_003362

    62. Kbio2_005930

    63. Kbio3_001132

    64. Dtxsid70925231

    65. 3,4,5-trihydroxy-benzoic Acid 2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-chroman-3-yl Ester

    66. Hy-n0002

    67. Zinc3978503

    68. Bdbm50153015

    69. Ccg-38376

    70. Lmpk12020090

    71. S3925

    72. Akos015965216

    73. Ac-6037

    74. Am84365

    75. Cs-3761

    76. Sdccgmls-0066549.p001

    77. (-)-epi Catechin-3-o-gallate

    78. [(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-chroman-3-yl] 3,4,5-trihydroxybenzoate

    79. Ncgc00179135-01

    80. As-15722

    81. E0890

    82. 257e085

    83. Sr-05000002675

    84. Q-200002

    85. Q5382492

    86. Sr-05000002675-1

    87. Brd-k50660797-001-01-0

    88. Brd-k50660797-001-03-6

    89. (-)-epicatechin Gallate, >=98% (hplc), From Green Tea

    90. Epicatechin Gallate, Primary Pharmaceutical Reference Standard

    91. [(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl] 3,4,5-trihydroxybenzoate

    92. Rel-(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxychroman-3-yl 3,4,5-trihydroxybenzoate

    93. (-)-epicatechin-3-o-gallate (constituent Of Grape Seeds Oligomeric Proanthocyanidins) [dsc]

    94. (-)-epicatechin-3-o-gallate(egc) (constituent Of Powdered Decaffeinated Green Tea Extract) [dsc]

    95. (2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

    96. 3,4,5-trihydroxy-benzoic Acid (2r,3r)-2-(3,4-dihydroxy-phenyl)-5,7-dihydroxy-chroman-3-yl Ester

    97. Benzoic Acid, 3,4,5-trihydroxy-, 2-(3,4-dihydroxyphenyl)-3,4-dihydro-5,7- Dihydroxy-2h-1-benzopyran-3-yl Ester, (-)-cis-

    98. Ncgc00179135-03![(2r,3r)-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2h-chromen-3-yl] 3,4,5-trihydroxybenzoate

    2.4 Create Date
    2005-08-01
    3 Chemical and Physical Properties
    Molecular Weight 442.4 g/mol
    Molecular Formula C22H18O10
    XLogP31.5
    Hydrogen Bond Donor Count7
    Hydrogen Bond Acceptor Count10
    Rotatable Bond Count4
    Exact Mass442.08999677 g/mol
    Monoisotopic Mass442.08999677 g/mol
    Topological Polar Surface Area177 Ų
    Heavy Atom Count32
    Formal Charge0
    Complexity649
    Isotope Atom Count0
    Defined Atom Stereocenter Count2
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    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.)

    Protease Inhibitors

    Compounds which inhibit or antagonize biosynthesis or actions of proteases (ENDOPEPTIDASES). (See all compounds classified as Protease Inhibitors.)

    Antineoplastic Agents, Phytogenic

    Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)