Skip Navigation
ChemIDplus Lite•Browse•Advanced

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
* denotes mobile formatted website

Links to Resources

NLM Resources (File Locators)

Regulatory Agencies (Superlist Locators)

Other Resources (Internet Locators)


Search for this InChIKey on the Web

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.