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    Shikimic Acid API

    ACTIVE PHARMA INGREDIENTS

    PharmaCompass
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    2D Structure
    Also known as: 138-59-0, Shikimate, L-shikimic acid, (-)-shikimic acid, (3r,4s,5r)-3,4,5-trihydroxycyclohex-1-enecarboxylic acid, (3r,4s,5r)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
    Molecular Formula
    C7H10O5
    Molecular Weight
    174.15  g/mol
    InChI Key
    JXOHGGNKMLTUBP-HSUXUTPPSA-N
    FDA UNII
    29MS2WI2NU
    A tri-hydroxy cyclohexene carboxylic acid important in biosynthesis of so many compounds that the shikimate pathway is named after it.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    (3R,4S,5R)-3,4,5-trihydroxycyclohexene-1-carboxylic acid
    2.1.2 InChI
    InChI=1S/C7H10O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,4-6,8-10H,2H2,(H,11,12)/t4-,5-,6-/m1/s1
    2.1.3 InChI Key
    JXOHGGNKMLTUBP-HSUXUTPPSA-N
    2.1.4 Canonical SMILES
    C1C(C(C(C=C1C(=O)O)O)O)O
    2.1.5 Isomeric SMILES
    C1[C@H]([C@@H]([C@@H](C=C1C(=O)O)O)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    29MS2WI2NU
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Acid, Shikimic

    2.3.2 Depositor-Supplied Synonyms

    1. 138-59-0

    2. Shikimate

    3. L-shikimic Acid

    4. (-)-shikimic Acid

    5. (3r,4s,5r)-3,4,5-trihydroxycyclohex-1-enecarboxylic Acid

    6. (3r,4s,5r)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic Acid

    7. (3r,4s,5r)-3,4,5-trihydroxycyclohexene-1-carboxylic Acid

    8. Ccris 7681

    9. 1-cyclohexene-1-carboxylic Acid, 3,4,5-trihydroxy-, (3r,4s,5r)-

    10. Hsdb 3537

    11. 3alpha,4alpha,5beta-trihydroxy-1-cyclohexene-1-carboxylic Acid

    12. Bracken Fern Toxic Component

    13. 29ms2wi2nu

    14. 1-cyclohexene-1-carboxylic Acid, 3,4,5-trihydroxy-, (3r-(3alpha,4alpha,5beta))-

    15. Chembl290345

    16. 106210-02-0

    17. Hydrotris(3-phenylpyrazol-1-yl)borate Thallium Salt

    18. Chebi:16119

    19. 3,4,5-trihydroxy-1-cyclohexenecarboxylic Acid

    20. (3r,4s,5r)-(-)-3,4,5-trihydroxy-1-cyclohexenecarboxylic Acid

    21. [3r-(3alpha,4alpha,5beta)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic Acid

    22. Mfcd00066278

    23. Smr001306700

    24. (-)-shikimate

    25. Sr-01000632403

    26. Einecs 205-334-2

    27. Nsc 59257

    28. Unii-29ms2wi2nu

    29. Skikimate

    30. Shicimic Acid

    31. L-shikimate

    32. Nsc-59257

    33. 2aay

    34. 4guj

    35. Verochic

    36. Spectrum_001232

    37. 1we2

    38. 2aa9

    39. Specplus_000488

    40. Spectrum2_001508

    41. Spectrum3_001541

    42. Spectrum4_001853

    43. Spectrum5_000386

    44. 1-cyclohexene-1-carboxylic Acid, 3,4,5-trihydroxy-

    45. Shikimic Acid, >=99%

    46. Bmse000114

    47. Ec 205-334-2

    48. Shikimic Acid [mi]

    49. Schembl43377

    50. Bspbio_002982

    51. Kbiogr_002287

    52. Kbioss_001712

    53. Shikimic Acid [hsdb]

    54. Shikimic Acid [iarc]

    55. Shikimic Acid [inci]

    56. Mls002207031

    57. Mls004256600

    58. Divk1c_006584

    59. Spectrum1502256

    60. L-(-)-shikimic Acid

    61. Spbio_001555

    62. Megxp0_001939

    63. Dtxsid4032039

    64. Kbio1_001528

    65. Kbio2_001712

    66. Kbio2_004280

    67. Kbio2_006848

    68. Kbio3_002482

    69. (4s,3r,5r)-3,4,5-trihydroxycyclohex-1-enecarboxylic Acid

    70. Shikimic Acid, Analytical Standard

    71. Hy-n0130

    72. Zinc3860720

    73. Bdbm50281998

    74. Ccg-38884

    75. Akos004119897

    76. Ac-8010

    77. Sdccgmls-0066740.p001

    78. Smp1_000326

    79. Ncgc00142601-01

    80. Ncgc00142601-02

    81. As-13905

    82. Cs-0007856

    83. N1829

    84. C00493

    85. 138s590

    86. Q410830

    87. Q-100148

    88. Sr-01000632403-1

    89. Sr-01000632403-4

    90. Sr-01000632403-5

    91. (-)-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic Acid

    92. B1a53f8a-8664-405d-8370-a9785add2d0b

    93. (3r,4s,5r)-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic Acid

    94. (3r,4s,5r)-(-)-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic Acid

    95. 1-cyclohexene-1-carboxylic Acid, 3,4,5-trihydroxy-, (3r,4s,5r)- (9ci)

    96. Shikimic Acid (constituent Of Cranberry Liquid Preparation) [dsc]

    97. [3r-(3 Alpha,4 Alpha,5 Beta)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic Acid

    98. 1-cyclohexene-1-carboxylic Acid, 3,4,5-trihydroxy-, (3r-(3alpha,4alpha,5beta))

    99. 1-cyclohexene-1-carboxylic Acid, 3,4,5-trihydroxy-, (3r-(3alpha,4alpha,5beta))- (9ci)

    100. Shikimic Acid [3r-(3alpha,4alpha,5beta)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic Acid

    2.4 Create Date
    2004-09-16
    3 Chemical and Physical Properties
    Molecular Weight 174.15 g/mol
    Molecular Formula C7H10O5
    XLogP3-1.7
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count5
    Rotatable Bond Count1
    Exact Mass174.05282342 g/mol
    Monoisotopic Mass174.05282342 g/mol
    Topological Polar Surface Area98 Ų
    Heavy Atom Count12
    Formal Charge0
    Complexity222
    Isotope Atom Count0
    Defined Atom Stereocenter Count3
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Pharmacology and Biochemistry
    4.1 Metabolism/Metabolites

    SHIKIMIC ACID IS METABOLIZED INTO CYCLOHEXANECARBOXYLIC ACID BY THE INTESTINAL MICROFLORA, BUT THE AROMATIZATION OF CYCLOHEXANECARBOXYLIC ACID OCCURS IN MAMMALIAN TISSUES. IN RATS, THIS ACID IS METABOLIZED AND EXCRETED IN THE URINE MAINLY AS HIPPURIC ACID, TOGETHER WITH 3,4,5,6-TETRAHYDROHIPPURIC ACID & HEXAHYDROHIPPURIC ACID AND SMALL AMT OF BENZOYL & CYCLOHEXYLCARBONYL GLUCURONIDES.

    The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 5: A Review of the Literature Published during 1976 and 1977. London: The Chemical Society, 1979., p. 154

    RATS METABOLIZED (14)C-LABELED SHIKIMIC ACID TO HIPPURIC ACID & CATECHOL IN VIVO; RAT CECAL CONTENTS CONVERTED IT TO CYCLOHEXANECARBOXYLIC ACID IN VITRO, THIS CONVERSION BEING ALMOST TOTALLY INHIBITED BY ANTIBIOTICS.

    PMID:1001716 BREWSTER D ET AL; BIOCHEM SOC TRANS 4 (3): 518 (1976)