Common NameShikimate
DescriptionShikimic acid, more commonly known as its anionic form shikimate, is a cyclohexene, a cyclitol and a cyclohexanecarboxylic acid. It is an important biochemical intermediate in plants and microorganisms. Its name comes from the Japanese flower shikimi (the Japanese star anise, Illicium anisatum), from which it was first isolated. Shikimic acid is a precursor for: the aromatic amino acids phenylalanine and tyrosine; indole, indole derivatives and tryptophan; many alkaloids and other aromatic metabolites; tannins; and lignin. In pharmaceutical industry, shikimic acid from chinese star anise is used as a base material for production of Tamiflu (oseltamivir). Although shikimic acid is present in most autotrophic organisms, it is a biosynthetic intermediate and generally found in very low concentrations.
Structure
Molecular FormulaC7H10O5
Average Mass174.15130
Monoisotopic Mass174.05282
IUPAC Name(3R,4S,5R)-3,4,5-trihydroxycyclohex-1-ene-1-carboxylic acid
Traditional NameShikimic acid
CAS Registry Number138-59-0
SMILESO=C([O-])C1=C[C@@H](O)[C@@H](O)[C@H](O)C1
InChI IdentifierInChI=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
InChI KeyJXOHGGNKMLTUBP-HSUXUTPPSA-N
CHEBI IDCHEBI:36208
HMDB IDHMDB0003070
StateSolid
Water Solubility2.06e+02 g/l
logP-1.70
logS0.07
pKa (Strongest Acidic)4.10
pKa (Strongest Basic)-3.22
Hydrogen Acceptor Count5
Hydrogen Donor Count4
Polar Surface Area97.99 Ų
Rotatable Bond Count1
Physiological Charge-1
Formal Charge0
Refractivity38.96 m³·mol⁻¹
Polarizability15.75

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