FComEx: Shikimic acid (PC000590)

Record Information

Version

1.0

Creation date

2015-10-09 22:31:25 UTC

Update date

2017-01-19 02:36:29 UTC

FoodComEx ID

PC000590

FoodDB Record

FDB003991

Chemical Information

Name

Shikimic acid

Description

Shikimic acid, also known as shikimate or acid, shikimic, belongs to the class of organic compounds known as shikimic acids and derivatves. These are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5. A cyclohexenecarboxylic acid that is cyclohex-1-ene-1-carboxylic acid substituted by hydroxy groups at positions 3, 4 and 5 (the 3R,4S,5R stereoisomer). Shikimic acid is an extremely weak basic (essentially neutral) compound (based on its pKa). Shikimic acid exists in all living species, ranging from bacteria to humans. Outside of the human body, Shikimic acid has been detected, but not quantified in, several different foods, such as barley, macadamia nuts, nutmegs, winter squash, and borages. This could make shikimic acid a potential biomarker for the consumption of these foods.

CAS Number

138-59-0

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Synonym	Source
(-)-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid	biospider
(-)-Shikimate	biospider
(-)-Shikimic acid	biospider
(3R,4S,5R)-3,4,5-Trihydroxycyclohex-1-ene carboxylic acid	biospider
[3R-(3a,4a,5b)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylate	Generator
[3R-(3a,4a,5b)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid	Generator
[3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylate	Generator
[3R-(3alpha,4alpha,5beta)]-3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid	ChEBI
[3R-(3α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylate	Generator
[3R-(3α,4α,5β)]-3,4,5-trihydroxy-1-cyclohexene-1-carboxylic acid	Generator
3,4,5-Trihydroxy-1-cyclohexene-1-carboxylic acid	biospider
3,4,5-Trihydroxy-1-cyclohexenecarboxylate	Generator
3,4,5-Trihydroxy-1-cyclohexenecarboxylic acid	biospider
3a,4a,5b-Trihydroxy-1-cyclohexene-1-carboxylate	Generator
3a,4a,5b-Trihydroxy-1-cyclohexene-1-carboxylic acid	Generator
3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylate	Generator
3alpha,4alpha,5beta-Trihydroxy-1-cyclohexene-1-carboxylic acid	ChEBI
3α,4α,5β-trihydroxy-1-cyclohexene-1-carboxylate	Generator
3α,4α,5β-trihydroxy-1-cyclohexene-1-carboxylic acid	Generator
L-Shikimate	biospider
L-Shikimic acid	biospider
Shikimate	biospider
Shikimic acid	biospider
Skikimate	HMDB
Skikimic acid	HMDB

Chemical Formula

C7H10O5

IUPAC name

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

InChI Identifier

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

InChI Key

JXOHGGNKMLTUBP-HSUXUTPPSA-N

Isomeric SMILES

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

Average Molecular Weight

174.1513

Monoisotopic Molecular Weight

174.05282343

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as shikimic acids and derivatves. These are cyclitols containing a cyclohexanecarboxylic acid substituted with three hydroxyl groups at positions 3, 4, and 5.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Shikimic acids and derivatves

Alternative Parents