Record Information
Version2.0
Creation Date2012-05-31 14:27:48 -0600
Update Date2015-06-03 17:19:19 -0600
Secondary Accession Numbers
  • ECMDB20106
Identification
Name:5-O-(1-Carboxyvinyl)-3-phosphoshikimate
Description5-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
Thumb
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentMonoalkyl phosphates
Alternative Parents
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 FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-4
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility5.63 g/LALOGPS
logP-0.83ALOGPS
logP-1.1ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)1.31ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-4ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area170.82 ŲChemAxon
Rotatable Bond Count6ChemAxon
Refractivity65.58 m³·mol⁻¹ChemAxon
Polarizability26.13 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
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 TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9231000000-67ac19174e5a550b1481View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a6r-3079000000-4fc890f00ff2a2c1037eView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-2092000000-1d9cc5b2cadb3db98046View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0ac1-8930000000-4ff9712d95c3009d70c3View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00fr-6059000000-24817ec47586471218adView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9051000000-6520d5fbd79bb20ba04aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-07abacf74b9ddf9a73c8View in MoNA
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
External Links:
ResourceLink
CHEBI ID16257
HMDB IDNot Available
Pubchem Compound ID439463
Kegg IDC01269
ChemSpider ID388567
Wikipedia IDNot Available
BioCyc ID3-ENOLPYRUVYL-SHIKIMATE-5P
EcoCyc ID3-ENOLPYRUVYL-SHIKIMATE-5P
Ligand ExpoEPS

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.