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Record Information
Version	2.0
Creation Date	2015-09-08 17:50:03 -0600
Update Date	2016-09-13 16:35:44 -0600
Secondary Accession Numbers	ECMDB24203
Identification
Name:	5-enolpyruvyl-shikimate 3-phosphate
Description	5-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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0x8a5fb77c> Close
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.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Dicarboxylic acids and derivatives
Direct Parent	Dicarboxylic acids and derivatives
Alternative Parents	Cyclitols and derivatives Alkyl phosphates Secondary alcohols Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds Organic anions
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 Framework	Aliphatic homomonocyclic compounds
External Descriptors	organophosphate oxoanion (CHEBI:57701 )
Physical Properties
State:	Not Available
Charge:	-4
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 23.8 g/L ALOGPS logP -0.11 ALOGPS logP -1.1 ChemAxon logS -1.2 ALOGPS pKa (Strongest Acidic) 1.31 ChemAxon pKa (Strongest Basic) -3.6 ChemAxon Physiological Charge -4 ChemAxon Hydrogen Acceptor Count 9 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 182.14 Ų ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 85.01 m³·mol⁻¹ ChemAxon Polarizability 24.94 ų ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule Yes ChemAxon
Biological Properties
Cellular Locations:	Cytoplasm
Reactions:	shikimate 3-phosphate + Phosphoenolpyruvic acid + Shikimate 3-phosphate > Phosphate + 5-enolpyruvyl-shikimate 3-phosphate 5-enolpyruvyl-shikimate 3-phosphate > Phosphate + Chorismate
SMPDB Pathways:	Chorismate biosynthesis PW000816
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
Links
External Links:	Resource Link CHEBI ID 57701 HMDB ID Not Available Pubchem Compound ID 14506801 Kegg ID Not Available ChemSpider ID Not Available Wikipedia ID Not Available BioCyc ID Not Available

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