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Shikimic Acid API

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Chemistry

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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

Shikimic Acid API

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 Formula	C₇H₁₀O₅
Molecular Weight	174.15 g/mol
XLogP3	-1.7
Hydrogen Bond Donor Count	4
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	1
Exact Mass	174.05282342 g/mol
Monoisotopic Mass	174.05282342 g/mol
Topological Polar Surface Area	98 Å²
Heavy Atom Count	12
Formal Charge	0
Complexity	222
Isotope Atom Count	0
Defined Atom Stereocenter Count	3
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 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)

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