Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C7H10O5 |
| Molecular Weight | 174.1513 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O[C@@H]1CC(=C[C@@H](O)[C@H]1O)C(O)=O
InChI
InChIKey=JXOHGGNKMLTUBP-HSUXUTPPSA-N
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
Shikimic acid (SA), an active metabolite of polyphenol-rich food intake, originally extracted from Illicium verum Hook. fil. is an indispensable starting material for the synthesis of the antiviral drug oseltamivir and others useful compounds. In the biological studies, SA has been reported to have anti-inflammatory, analgesia, antioxidant, antithrombotic, and antibacterial activities. SA can play an important role in reducing platelet activation, aggregation related thrombus formation and biomarkers of thrombogenesis in sedentary individuals. In addition, was investigated antibacterial activity of SA against S. aureus, which could be caused by the interactions of SA with S. aureus membrane proteins and lipids, resulting in causing cell membrane dysfunction and bacterial damage or even death.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Thermotoga maritima 3-deoxy-D-arabino-heptulosonate 7-phosphate (DAHP) synthase: the ancestral eubacterial DAHP synthase? | 2003-07-25 |
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| Phosphoenolpyruvate availability and the biosynthesis of shikimic acid. | 2003-06-07 |
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| Experiences with the shikimate-pathway enzymes as targets for rational drug design. | 2003-06 |
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| Twists and turns: a tale of two shikimate-pathway enzymes. | 2003-06 |
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| Effects of salts on the function and conformational stability of shikimate kinase. | 2003-05-30 |
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| Regulation of biosynthesis and transport of aromatic amino acids in low-GC Gram-positive bacteria. | 2003-05-28 |
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| Structures of shikimate dehydrogenase AroE and its Paralog YdiB. A common structural framework for different activities. | 2003-05-23 |
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| The 2.3-A crystal structure of the shikimate 5-dehydrogenase orthologue YdiB from Escherichia coli suggests a novel catalytic environment for an NAD-dependent dehydrogenase. | 2003-05-23 |
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| Parallel synthesis of glycomimetic libraries: targeting a C-type lectin. | 2003-05-01 |
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| Quinic acid induces hypovirulence and expression of a hypovirulence-associated double-stranded RNA in Rhizoctonia solani. | 2003-05 |
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| Antioxidant activity of 3-dehydroshikimic acid in liposomes, emulsions, and bulk oil. | 2003-04-23 |
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| New quinoproteins in oxidative fermentation. | 2003-04-11 |
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| One-step purification of 5-enolpyruvylshikimate-3-phosphate synthase enzyme from Mycobacterium tuberculosis. | 2003-04 |
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| Laser-capture microdissection, a tool for the global analysis of gene expression in specific plant cell types: identification of genes expressed differentially in epidermal cells or vascular tissues of maize. | 2003-03 |
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| Crystallization and preliminary X-ray crystallographic studies of chorismate synthase from Helicobacter pylori. | 2003-03 |
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| A series of 2(Z)-2-benzylidene-6,7-dihydroxybenzofuran-3[2H]-ones as inhibitors of chorismate synthase. | 2003-02-10 |
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| Wavelength-dependent induction of a mycosporine-like amino acid in a rice-field cyanobacterium, Nostoc commune: role of inhibitors and salt stress. | 2003-02 |
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| New developments in oxidative fermentation. | 2003-02 |
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| The biosynthesis of shikimate metabolites. | 2003-02 |
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| Expression of a hypovirulence-causing double-stranded RNA is associated with up-regulation of quinic acid pathway and down-regulation of shikimic acid pathway in Rhizoctonia solani. | 2003-02 |
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| Shikimate accumulates in both glyphosate-sensitive and glyphosate-resistant horseweed (Conyza canadensis L. Cronq.). | 2003-01-29 |
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| Purification, cloning, and properties of an acyltransferase controlling shikimate and quinate ester intermediates in phenylpropanoid metabolism. | 2003-01-03 |
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| Isoflavone, glyphosate, and aminomethylphosphonic acid levels in seeds of glyphosate-treated, glyphosate-resistant soybean. | 2003-01-01 |
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| Modulation of phosphoenolpyruvate synthase expression increases shikimate pathway product yields in E. coli. | 2002-12-07 |
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| Hydrophilic carboxylic acids and iridoid glycosides in the juice of American and European cranberries (Vaccinium macrocarpon and V. oxycoccos), lingonberries (V. vitis-idaea), and blueberries (V. myrtillus). | 2002-11-06 |
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| How the mutation glycine96 to alanine confers glyphosate insensitivity to 5-enolpyruvyl shikimate-3-phosphate synthase from Escherichia coli. | 2002-11 |
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| Galactosyl-mimodye ligands for Pseudomonas fluorescens beta-galactose dehydrogenase. | 2002-11 |
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| [Change in biochemical composition of amaranth leaves as a result of selection for increased level of amaranthine pigment]. | 2002-10-24 |
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| Synthesis and mannose receptor-mediated uptake of clustered glycomimetics by human dendritic cells: effect of charge. | 2002-10-07 |
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| Pulse experiments as a prerequisite for the quantification of in vivo enzyme kinetics in aromatic amino acid pathway of Escherichia coli. | 2002-10-05 |
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| The common aromatic amino acid biosynthesis pathway is essential in Mycobacterium tuberculosis. | 2002-10 |
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| Cloning and expression of functional shikimate dehydrogenase (EC 1.1.1.25) from Mycobacterium tuberculosis H37Rv. | 2002-10 |
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| Characterization of the early stage aminoshikimate pathway in the formation of 3-amino-5-hydroxybenzoic acid: the RifN protein specifically converts kanosamine into kanosamine 6-phosphate. | 2002-09-11 |
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| Kanosamine biosynthesis: a likely source of the aminoshikimate pathway's nitrogen atom. | 2002-09-11 |
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| Defense chemistry of cyanogenic Eucalyptus cladocalyx seedlings is affected by water supply. | 2002-09 |
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| Fig volatile compounds--a first comparative study. | 2002-09 |
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| High level expression of chorismate pyruvate-lyase (UbiC) and HMG-CoA reductase in hairy root cultures of Lithospermum erythrorhizon. | 2002-08 |
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| Redox regulation of Arabidopsis 3-deoxy-D-arabino-heptulosonate 7-phosphate synthase. | 2002-08 |
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| Plant allelochemicals differentially regulate Helicoverpa zea cytochrome P450 genes. | 2002-08 |
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| Regioselective enzymatic acylation of methyl shikimate. Influence of acyl chain length and solvent polarity on enzyme specificity. | 2002-07-12 |
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| Molecular model of shikimate kinase from Mycobacterium tuberculosis. | 2002-07-05 |
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| Pneumocystis carinii f. sp. carinii synthesizes de novo four homologs of ubiquinone. | 2002-07-04 |
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| Crystal structure of shikimate kinase from Mycobacterium tuberculosis reveals the dynamic role of the LID domain in catalysis. | 2002-06-07 |
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| LC/MS/MS characterization of phenolic constituents in dried plums. | 2002-06-05 |
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| Deoxygenation of polyhydroxybenzenes: an alternative strategy for the benzene-free synthesis of aromatic chemicals. | 2002-05-29 |
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| [Experimental studies on the anti-thrombosis effect of 3,4-oxo-isopropylidene-shikimic acid]. | 2002-04 |
|
| [Chemical constituents of Hyperricum monogynum]. | 2002-02 |
|
| [Genetic control of the isocitrate dehydrogenase and shikimate dehydrogenase isoenzyme systems in Sesame (Sesamun indicum L.)]. | 2002 |
|
| Genetic variation in three species of Hordeum, and the selection of accessions for the Barley Core Collection. | 2002 |
|
| [Determination of shikimic acid in fruit of Illiciaceae plants by HPLC with diode-array detection]. | 2001-07 |
Patents
Sample Use Guides
in mice: shikimic acid at 50, 100, and 200mg/kg decreased formalin-induced nociceptive behavior (around 50%) and inhibited the inflammatory nociception induced by TNF-α and PGE2 (50 to 75% each).
Route of Administration:
Oral
It was evaluated neuroprotective actions of Shikimic acid (SA) against oxidative stress-induced toxicity on human neuronal-like cells (SH-SY5Y). In vitro antioxidant activity of SA without exerting cytotoxic effects on SH-SY5Y cells at tested concentrations of 10 nM, 10 μM, and 10 mM. In addition, SA protected the cells against H2O2-induced toxicity; effect that could be related, at least in part, with decreased intracellular RS production and its antioxidant potential. The present study shows evidence for neuroprotective actions of SA against oxidative stress-induced toxicity on SH-SY5Y.
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2038 (Number of products:1)
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SHIKIMIC ACID
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SUBSTANCE RECORD
