Record Information
Version2.0
Creation Date2015-09-08 17:50:03 -0600
Update Date2016-09-13 16:35:44 -0600
Secondary Accession Numbers
  • ECMDB24203
Identification
Name:5-enolpyruvyl-shikimate 3-phosphate
Description5-Enolpyruvyl-shikimate 3-phosphate is a member of the chemical class known as Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group. The shikimate pathway enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS) is the target of the broad spectrum herbicide glyphosate. (PMID 19211556) 5-Enolpyruvylshikimate-3-phosphate (EPSP) synthase (AroA) is a key enzyme in the aromatic amino acid biosynthetic pathway in microorganisms and plants, and is the target of the herbicide glyphosate. (PMID 16469313)
Structure
Thumb
Synonyms:
  • 5-Enolpyruvyl-shikimic acid 3-phosphoric acid
Chemical Formula:
Weight:Average: Not Available
Monoisotopic: Not Available
InChI Key:Not Available
InChI:Not Available
CAS number:Not Available
IUPAC Name:(3R,4S,5R)-5-[(1-carboxylatoeth-1-en-1-yl)oxy]-4-hydroxy-3-(phosphonatooxy)cyclohex-1-ene-1-carboxylate
Traditional IUPAC Name:(3R,4S,5R)-5-[(1-carboxylatoeth-1-en-1-yl)oxy]-4-hydroxy-3-(phosphonatooxy)cyclohex-1-ene-1-carboxylate
SMILES:Not Available
Chemical Taxonomy
Description belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Alkyl phosphate
  • Phosphoric acid ester
  • Organic phosphoric acid derivative
  • Dicarboxylic acid or derivatives
  • Cyclitol or derivatives
  • Secondary alcohol
  • Carboxylic acid
  • Organic oxygen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Organic anion
  • Aliphatic homomonocyclic compound
Molecular FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility23.8 g/LALOGPS
logP-0.11ALOGPS
logP-1.1ChemAxon
logS-1.2ALOGPS
pKa (Strongest Acidic)1.31ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area182.14 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity85.01 m³·mol⁻¹ChemAxon
Polarizability24.94 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
SMPDB Pathways:
Chorismate biosynthesisPW000816 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:Not Available
EcoCyc Pathways:Not Available
Concentrations
Not Available
Spectra
Spectra:Not Available
References
References:Not Available
Synthesis Reference:Not Available
Material Safety Data Sheet (MSDS)Not Available
External Links:
ResourceLink
CHEBI ID57701
HMDB IDNot Available
Pubchem Compound ID14506801
Kegg IDNot Available
ChemSpider IDNot Available
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

General function:
Involved in transferase activity, transferring alkyl or aryl (other than methyl) groups
Specific function:
Phosphoenolpyruvate + 3-phosphoshikimate = phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate
Gene Name:
aroA
Uniprot ID:
P0A6D3
Molecular weight:
46095
Reactions
Phosphoenolpyruvate + 3-phosphoshikimate = phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate.
General function:
Involved in chorismate synthase activity
Specific function:
5-O-(1-carboxyvinyl)-3-phosphoshikimate = chorismate + phosphate
Gene Name:
aroC
Uniprot ID:
P12008
Molecular weight:
39137
Reactions
5-O-(1-carboxyvinyl)-3-phosphoshikimate = chorismate + phosphate.