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    Technical details about Prestwick3_000427, learn more about the structure, uses, toxicity, action, side effects and more

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    Prestwick3_000427

    APIs // Active Pharmaceutical Ingredients

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    Phyton is a World Leader in Plant Cell Fermentation Technology and Commercial Manufacturing.

    Athena Pharmaceutiques is a Partner of Choice for Drug Delivery & Life Cycle Management.

    2D Structure
    Also known as: 327-97-9, 3-o-caffeoylquinic acid, Heriguard, 3-(3,4-dihydroxycinnamoyl)quinic acid, 3-caffeoylquinic acid, Chlorogenate
    Molecular Formula
    C16H18O9
    Molecular Weight
    354.31  g/mol
    InChI Key
    CWVRJTMFETXNAD-JUHZACGLSA-N
    FDA UNII
    318ADP12RI
    A naturally occurring phenolic acid which is a carcinogenic inhibitor. It has also been shown to prevent paraquat-induced oxidative stress in rats. (From J Chromatogr A 1996;741(2):223-31; Biosci Biotechnol Biochem 1996;60(5):765-68).
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (1S,3R,4R,5R)-3-[(E)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic acid
    2.1.2 InChI
    InChI=1S/C16H18O9/c17-9-3-1-8(5-10(9)18)2-4-13(20)25-12-7-16(24,15(22)23)6-11(19)14(12)21/h1-5,11-12,14,17-19,21,24H,6-7H2,(H,22,23)/b4-2+/t11-,12-,14-,16+/m1/s1
    2.1.3 InChI Key
    CWVRJTMFETXNAD-JUHZACGLSA-N
    2.1.4 Canonical SMILES
    C1C(C(C(CC1(C(=O)O)O)OC(=O)C=CC2=CC(=C(C=C2)O)O)O)O
    2.1.5 Isomeric SMILES
    C1[C@H]([C@H]([C@@H](C[C@@]1(C(=O)O)O)OC(=O)/C=C/C2=CC(=C(C=C2)O)O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    318ADP12RI
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 3 Caffeoylquinic Acid

    2. 3-caffeoylquinic Acid

    3. Acid, 3-caffeoylquinic

    4. Acid, Chlorogenic

    2.3.2 Depositor-Supplied Synonyms

    1. 327-97-9

    2. 3-o-caffeoylquinic Acid

    3. Heriguard

    4. 3-(3,4-dihydroxycinnamoyl)quinic Acid

    5. 3-caffeoylquinic Acid

    6. Chlorogenate

    7. Hlorogenic Acid

    8. Cp Chlorogenic Acid

    9. Nsc-407296

    10. Caffeoyl Quinic Acid

    11. 5-cqa

    12. (+)-chlorogenic Acid

    13. Chlorogenic Acid [mi]

    14. 5-o-(3,4-dihydroxycinnamoyl)-l-quinic Acid

    15. Trans-chlorogenic Acid

    16. Caffetannic Acid

    17. Trans-caffeic Acid 5-o-d-quinate

    18. Chlorogenic Acid [who-dd]

    19. Cis-chlorogenic Acid

    20. Nsc 70861

    21. Nsc-70861

    22. (1s,3r,4r,5r)-3-[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxycyclohexane-1-carboxylic Acid

    23. Nsc 407296

    24. Trans-5-o-caffeoylquinic Acid

    25. 318adp12ri

    26. Chembl284616

    27. 202650-88-2

    28. Chebi:16112

    29. Cyclohexanecarboxylic Acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1s-(1-alpha,3-beta,4-alpha,5-alpha))-

    30. Chlorogenic Acid (constituent Of St. John's Wort) [dsc]

    31. Mfcd00003862

    32. 3-o-(3,4-dihydroxycinnamoyl)-d-quinic Acid

    33. (1s,3r,4r,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic Acid

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

    35. Cyclohexanecarboxylic Acid, 3-(((2e)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propen-1-yl)oxy)-1,4,5-trihydroxy-, (1s,3r,4r,5r)-

    36. Cyclohexanecarboxylic Acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1s,3r,4r,5r)-

    37. Cyclohexanecarboxylic Acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, (1s,3r,4r,5r)-

    38. Chlorogenicacid

    39. Caffeoylquinic Acid

    40. 1,3,4,5-tetrahydroxycyclohexanecarboxylic Acid 3-(3,4-dihydroxycinnamate)

    41. 3-o-caffeoyl-d-quinic Acid

    42. 1,3,4,5-tetrahydroxycyclohexanecarboxylic Acid 3-(3,4-dihydroxycinnamate

    43. 3-caffeoylquinate

    44. 5-caffeoylquinic Acid

    45. 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy] 1,4,5-trihydroxycyclohexanecarboxylic Acid

    46. 5-caffeoyl Quinic Acid

    47. (1s,3r,4r,5r)-3-(((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylic Acid

    48. [1s-(1alpha,3beta,4alpha,5alpha)]-3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic Acid

    49. [1s-(1alpha,3beta,4alpha,5alpha)]3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxycyclohexanecarboxylic Acid

    50. Cyclohexanecarboxylic Acid, 3-[[(2e)-3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, (1s,3r,4r,5r)-

    51. Cyclohexanecarboxylic Acid, 3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-, [1s-(1alpha,3beta,4alpha,5alpha)]-

    52. Ccris 1400

    53. Einecs 206-325-6

    54. 3-trans-caffeoylquinic Acid

    55. Unii-318adp12ri

    56. Hlorogenate

    57. Helianthic Acid

    58. Igasuric Acid

    59. Nsc70861

    60. Chlorogenic-acid

    61. Nsc407296

    62. Caffeylquinic Acid

    63. 3-(3,4-dihydroxycinnamoyl)quinate

    64. Prestwick_112

    65. (e)-chlorogenic Acid

    66. Hoodia Chinese Extract

    67. Chlorogenic Acid, Chiral

    68. Chlorogenic Acid (8ci)

    69. Prestwick2_000427

    70. Prestwick3_000427

    71. Spectrum5_000733

    72. Bmse000387

    73. Quinic Acid, 5-caffeoyl-

    74. Schembl19466

    75. Bspbio_000414

    76. Bspbio_003353

    77. Spectrum210800

    78. Mls002153805

    79. Bidd:er0453

    80. Bpbio1_000456

    81. Quinic Acid, 3-caffeoyl-, E-

    82. Acon1_000581

    83. Chebi:95271

    84. Chlorogenic Acid [usp-rs]

    85. Bdbm513080

    86. Dtxsid101318952

    87. Hms1569e16

    88. Hms1923c11

    89. Hms2096e16

    90. Hms2235f03

    91. Hms3649e06

    92. Act03375

    93. Albb-030169

    94. Cga

    95. Hy-n0055

    96. Zinc2138728

    97. Bdbm50327036

    98. Ccg-38471

    99. S2280

    100. Akos015955866

    101. Ac-6032

    102. Chlorogenic Acid, >=95% (titration)

    103. Cs-3766

    104. Db12029

    105. Sdccgmls-0066467.p001

    106. Ncgc00168941-01

    107. Ncgc00168941-02

    108. Ncgc00168941-03

    109. (1s,3r,4r,5r)-3-(((e)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexane-1-carboxylic Acid

    110. (1s,3r,4r,5r)-3-[(e)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic Acid

    111. As-12284

    112. Smr000857273

    113. Chlorogenic Acid 100 Microg/ml In Methanol

    114. Chlorogenic Acid 1000 Microg/ml In Acetone

    115. Chlorogenic Acid 10 Microg/ml In Acetonitrile

    116. C00852

    117. F16266

    118. 327c979

    119. Q421964

    120. Sr-01000841185

    121. Sr-01000946600

    122. D54cae3d-cdda-455d-a28e-77fc9efe4a43

    123. Sr-01000841185-4

    124. Sr-01000946600-1

    125. Brd-k47114202-001-06-2

    126. 32cf6d13-8f08-485f-b79e-f8a6ac318e07

    127. Chlorogenic Acid, Primary Pharmaceutical Reference Standard

    128. Chlorogenic Acid, European Pharmacopoeia (ep) Reference Standard

    129. Chlorogenic Acid, United States Pharmacopeia (usp) Reference Standard

    130. 3-[(e)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic Acid

    131. 3-[3-(3,4-dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic Acid

    132. (1r,3s,4s,5s)-3-[(e)-3-(3,4-dihydroxy-phenyl)-acryloyloxy]-1,4,5-trihydroxy-cyclohexanecarboxylic Acid

    133. (1s,3r,4r,5r)-3-(((3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylicacid

    134. (1s,3r,4r,5r)-3-(((e)-3-(3,4-dihydroxyphenyl)acryloyl)oxy)-1,4,5-trihydroxycyclohexanecarboxylic Acid

    135. (1s,3r,4r,5r)-3-((e)-3-(3,4-dihydroxyphenyl)acryloyloxy)-1,4,5-trihydroxycyclohexanecarboxylic Acid

    136. (1s,3r,4r,5r)-3-[(e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy-1,4,5-trihydroxy-cyclohexanecarboxylic Acid

    137. (1s,3r,4r,5r)-3-[3-(3,4-dihydroxyphenyl)prop-2-enoyloxy]-1,4,5-trihydroxycyclohexanecarboxylic Acid

    138. (1s,3r,4r,5r,e)-3-(3-(3,4-dihydroxyphenyl)acryloyloxy)-1,4,5-trihydroxycyclohexanecarboxylic Acid

    139. Cyclohexanecarboxylic Acid, 3-((3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl)oxy)-1,4,5-trihydroxy-, (1s-(1-.alpha.,3-.beta.,4-.alpha.,5-.alpha.))-

    140. Cyclohexanecarboxylic Acid,3-[[3-(3,4-dihydroxyphenyl)-1-oxo-2-propenyl]oxy]-1,4,5-trihydroxy-,(1s,3r,4r,5r)-

    141. Edit(1s,3r,4r,5r)-3-{[(2e)-3-(3,4-dihydroxyphenyl)prop-2-enoyl]oxy}-1,4,5-trihydroxycyclohexane-1-carboxylic Acid

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 354.31 g/mol
    Molecular Formula C16H18O9
    XLogP3-0.4
    Hydrogen Bond Donor Count6
    Hydrogen Bond Acceptor Count9
    Rotatable Bond Count5
    Exact Mass354.09508215 g/mol
    Monoisotopic Mass354.09508215 g/mol
    Topological Polar Surface Area165 Ų
    Heavy Atom Count25
    Formal Charge0
    Complexity534
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count1
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
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