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Record Information
Version	2.0
Creation Date	2012-05-31 14:27:48 -0600
Update Date	2015-06-03 17:19:19 -0600
Secondary Accession Numbers	ECMDB20106
Identification
Name:	5-O-(1-Carboxyvinyl)-3-phosphoshikimate
Description	5-o-(1-carboxyvinyl)-3-phosphoshikimate 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	MOLSDF3D-SDFPDBSMILESInChI View 3D Structure × Structure for #<Compound:0xb0aaa284> Close
Synonyms:	3-Enolpyruvyl-shikimate-5-P 3-Enolpyruvyl-shikimate-5-phosphate 3-Enolpyruvyl-shikimic acid-5-P 3-Enolpyruvyl-shikimic acid-5-phosphoric acid 5-ENOLPYRUVYLSHIKIMATE-3-PHOSPHATE 5-ENOLPYRUVYLSHIKIMic acid-3-phosphoric acid 5-O-(1-Carboxyvinyl)-3-phosphoshikimate 5-O-(1-Carboxyvinyl)-3-phosphoshikimic acid 5EPS3P EPS EPSP O5-(1-carboxyvinyl)-3-phosphate shikimate O5-(1-Carboxyvinyl)-3-phosphoric acid shikimic acid O5-(1-carboxyvinyl)-3-phosphoshikimate O5-(1-carboxyvinyl)-3-phosphoshikimic acid
Chemical Formula:	C10H13O10P
Weight:	Average: 324.178 Monoisotopic: 324.024633148
InChI Key:	QUTYKIXIUDQOLK-PRJMDXOYSA-N
InChI:	InChI=1S/C10H13O10P/c1-4(9(12)13)19-6-2-5(10(14)15)3-7(8(6)11)20-21(16,17)18/h3,6-8,11H,1-2H2,(H,12,13)(H,14,15)(H2,16,17,18)/t6-,7-,8+/m1/s1
CAS number:	89771-75-5
IUPAC Name:	(3R,4S,5R)-5-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid
Traditional IUPAC Name:	(3R,4S,5R)-5-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid
SMILES:	O[C@H]1[C@@H](CC(=C[C@H]1OP(O)(O)=O)C(O)=O)OC(=C)C(O)=O
Chemical Taxonomy
Description	belongs to the class of organic compounds known as monoalkyl phosphates. These are organic compounds containing a phosphate group that is linked to exactly one alkyl chain.
Kingdom	Organic compounds
Super Class	Organic acids and derivatives
Class	Organic phosphoric acids and derivatives
Sub Class	Phosphate esters
Direct Parent	Monoalkyl phosphates
Alternative Parents	Dicarboxylic acids and derivatives Cyclitols and derivatives Secondary alcohols Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Monoalkyl phosphate Dicarboxylic acid or derivatives Cyclitol or derivatives Secondary alcohol Carboxylic acid Carboxylic acid derivative Organic oxygen compound Organic oxide Hydrocarbon derivative Organooxygen compound Carbonyl group Alcohol Aliphatic homomonocyclic compound
Molecular Framework	Aliphatic homomonocyclic compounds
External Descriptors	dicarboxylic acid (CHEBI:16257 ) phosphoshikimic acid (CHEBI:16257 )
Physical Properties
State:	Not Available
Charge:	-4
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 5.63 g/L ALOGPS logP -0.83 ALOGPS logP -1.1 ChemAxon logS -1.8 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 5 ChemAxon Polar Surface Area 170.82 Ų ChemAxon Rotatable Bond Count 6 ChemAxon Refractivity 65.58 m³·mol⁻¹ ChemAxon Polarizability 26.13 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:	Phosphoenolpyruvic acid + Shikimate 3-phosphate <> 5-O-(1-Carboxyvinyl)-3-phosphoshikimate + Phosphate 5-O-(1-Carboxyvinyl)-3-phosphoshikimate <> Chorismate + Phosphate 5-O-(1-Carboxyvinyl)-3-phosphoshikimate > Phosphate + Chorismate Phosphoenolpyruvic acid + Shikimate 3-phosphate > Inorganic phosphate + 5-O-(1-Carboxyvinyl)-3-phosphoshikimate 5-O-(1-Carboxyvinyl)-3-phosphoshikimate > Chorismate + Inorganic phosphate 5 5-O-(1-Carboxyvinyl)-3-phosphoshikimate <> Chorismate + Phosphate
SMPDB Pathways:	Not Available
KEGG Pathways:	Metabolic pathways eco01100 Phenylalanine, tyrosine and tryptophan biosynthesis ec00400
EcoCyc Pathways:	chorismate biosynthesis from 3-dehydroquinate PWY-6163
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-0002-9231000000-67ac19174e5a550b1481 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0a6r-3079000000-4fc890f00ff2a2c1037e View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0a4r-2092000000-1d9cc5b2cadb3db98046 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0ac1-8930000000-4ff9712d95c3009d70c3 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-00fr-6059000000-24817ec47586471218ad View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9051000000-6520d5fbd79bb20ba04a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-07abacf74b9ddf9a73c8 View in MoNA 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer 1D NMR 13C NMR Spectrum Not Available View in JSpectraViewer 1D NMR 1H NMR Spectrum Not Available View in JSpectraViewer
References
References:	Funke, T., Yang, Y., Han, H., Healy-Fried, M., Olesen, S., Becker, A., Schonbrunn, E. (2009). "Structural basis of glyphosate resistance resulting from the double mutation Thr97 -> Ile and Pro101 -> Ser in 5-enolpyruvylshikimate-3-phosphate synthase from Escherichia coli." J Biol Chem 284:9854-9860. Pubmed: 19211556 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. Pubmed: 22080510 Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. Pubmed: 21097882 Sun, Y. C., Li, Y., Zhang, H., Yan, H. Q., Dowling, D. N., Wang, Y. P. (2006). "Reconstitution of the enzyme AroA and its glyphosate tolerance by fragment complementation." FEBS Lett 580:1521-1527. Pubmed: 16469313 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. Pubmed: 18331064
Synthesis Reference:	Not Available
Material Safety Data Sheet (MSDS)	Not Available
Links
External Links:	Resource Link CHEBI ID 16257 HMDB ID Not Available Pubchem Compound ID 439463 Kegg ID C01269 ChemSpider ID 388567 Wikipedia ID Not Available BioCyc ID 3-ENOLPYRUVYL-SHIKIMATE-5P EcoCyc ID 3-ENOLPYRUVYL-SHIKIMATE-5P Ligand Expo EPS

Enzymes