(5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid

• ChemBase ID: 72981
• Molecular Formular: C7H10O5
• Molecular Mass: 174.1513
• Monoisotopic Mass: 174.05282342
• SMILES: C1=C(C[C@H](C(C1O)O)O)C(=O)O
• Canonical SMILES: O[C@@H]1CC(=CC(C1O)O)C(=O)O
• 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-INWUZDNDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
• IUPAC Traditional name: (5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
• Synonyms: Shikimate; Bracken fern toxic component; L-Shikimic acid; Shikimic acid

Database IDs

• CAS Number: 138-59-0
• PubChem SID: 162037901
• PubChem CID: 49867941

CALCULATED PROPERTIES

• Acid pKa: 4.103319
• H Acceptors: 5
• H Donor: 4
• LogD (pH = 5.5): -3.0506496
• LogD (pH = 7.4): -4.7369246
• Log P: -1.6400741
• Molar Refractivity: 38.9603 cm^3
• Polarizability: 15.229941 Å^3
• Polar Surface Area: 97.99 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Salt Data: Free Base

DETAILS

Selleck Chemicals - S2356

Research Area: Metabolic Disease
Biological Activity:
Shikimic acid(Shikimate), more commonly known as its anionic form shikimate, is an important biochemical intermediate in plants and microorganisms. Shikimic acid is a precursor for: the aromatic amino acids phenylalanine and tyrosine；indole, indole derivatives and aromatic amino acid tryptophan；many alkaloids and other aromatic metabolites；tannins, flavonoids, and lignin. [1]

REFERENCES

• http://en.wikipedia.org/wiki/Shikimic_acid