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Substance Name: Shikimic acid
RN: 138-59-0
UNII: 29MS2WI2NU
InChIKey: JXOHGGNKMLTUBP-HSUXUTPPSA-N

Note

  • A tri-hydroxy cyclohexene carboxylic acid important in biosynthesis of so many compounds that the shikimate pathway is named after it.

Molecular Formula

  • C7-H10-O5

Molecular Weight

  • 174.151
 

Classification Codes

Classification Codes

  • Mutation Data
  • Natural Product
  • Tumor Data

Superlist Classification Code

  • Overall Carcinogenic Evaluation: Group 3
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Names and Synonyms

Name of Substance

  • Shikimic acid

MeSH Heading

  • Shikimic acid

Synonyms

  • 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R-(3alpha,4alpha,5beta))-
  • 3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid
  • 3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylic acid
  • Bracken fern toxic component
  • CCRIS 7681
  • EC 205-334-2
  • EINECS 205-334-2
  • HSDB 3537
  • NSC 59257
  • Shikimate
  • Shikimic acid
  • UNII-29MS2WI2NU

Systematic Names

  • (3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-enecarboxylic acid
  • 1-Cyclohexene-1-carboxylic acid, 3,4,5-trihydroxy-, (3R-(3alpha,4alpha,5beta))- (9CI)
  • Shikimic acid

Superlist Name

  • Shikimic acid

Registry Numbers

CAS Registry Number

  • 138-59-0

FDA UNII

  • 29MS2WI2NU

System Generated Number

  • 0000138590

Structure Descriptors

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

InChIKey

JXOHGGNKMLTUBP-HSUXUTPPSA-N

Smiles

O[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(=O)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 1gm/kg (1000mg/kg)   Nature. Vol. 250, Pg. 348, 1974.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 186 deg C   EXP
log P (octanol-water) -1.340 (none)   EST
Water Solubility 1.50E+05 mg/L 21 EXP
Vapor Pressure 5.00E-09 mm Hg 25 EST
Henry's Law Constant 2.69E-14 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 6.14E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.