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Record Information
Version	2.0
Creation Date	2012-05-31 14:32:26 -0600
Update Date	2015-09-17 15:42:00 -0600
Secondary Accession Numbers	ECMDB20193
Identification
Name:	Shikimate 3-phosphate
Description	Shikimate 3-phosphate is a member of the chemical class known as Organophosphate Esters. These are organic compounds containing phosphoric acid ester functional group. Shikimate 3-phosphate is involved in the shikimate pathway. The shikimate pathway enzyme 5-enolpyruvyl shikimate-3-phosphate synthase (EPSP synthase) has received attention in the past because it is the target of the broad-spectrum herbicide glyphosate. (PMID 16225867) The enzyme 5-enolpyruvylshikimate-3-phosphate synthase (EPSPS) catalyzes the penultimate step of the shikimate pathway and is the target of the broad-spectrum herbicide glyphosate. (PMID 15736934)
Structure	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xb1906d78> Close
Synonyms:	3-Phosphoshikimate 3-Phosphoshikimic acid 5-Phosphoshikimate 5-Phosphoshikimic acid S3P Shikimate 5-phosphate Shikimate-3-P Shikimate-3-Phosphate Shikimate-5-P Shikimate-5-phosphate SHIKIMATE-5P Shikimic acid 3-phosphate Shikimic acid 3-phosphoric acid Shikimic acid 5-phosphate Shikimic acid 5-phosphoric acid Shikimic acid-3-P Shikimic acid-3-phosphoric acid Shikimic acid-5-P Shikimic acid-5-phosphoric acid SHIKIMic acid-5P
Chemical Formula:	C7H8O8P
Weight:	Average: 251.108 Monoisotopic: 250.997324955
InChI Key:	QYOJSKGCWNAKGW-PBXRRBTRSA-K
InChI:	InChI=1S/C7H11O8P/c8-4-1-3(7(10)11)2-5(6(4)9)15-16(12,13)14/h2,4-6,8-9H,1H2,(H,10,11)(H2,12,13,14)/p-3/t4-,5-,6+/m1/s1
CAS number:	Not Available
IUPAC Name:	(3R,4S,5R)-4,5-dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid
Traditional IUPAC Name:	3-phosphoshikimic acid
SMILES:	[H][C@@]1(O)CC(=C[C@@]([H])(OP([O-])([O-])=O)[C@@]1([H])O)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	Cyclitols and derivatives Secondary alcohols 1,2-diols Monocarboxylic acids and derivatives Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Monoalkyl phosphate Cyclitol or derivatives Secondary alcohol 1,2-diol Monocarboxylic acid or derivatives 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	phosphoshikimic acid (CHEBI:17052 )
Physical Properties
State:	Not Available
Charge:	-3
Melting point:	Not Available
Experimental Properties:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 21 g/L ALOGPS logP -2.1 ALOGPS logP -1.8 ChemAxon logS -1.1 ALOGPS pKa (Strongest Acidic) 1.32 ChemAxon pKa (Strongest Basic) -3.2 ChemAxon Physiological Charge -3 ChemAxon Hydrogen Acceptor Count 7 ChemAxon Hydrogen Donor Count 5 ChemAxon Polar Surface Area 144.52 Ų ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 49.83 m³·mol⁻¹ ChemAxon Polarizability 20.46 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:	Adenosine triphosphate + Shikimic acid <> ADP + Hydrogen ion + Shikimate 3-phosphate Phosphoenolpyruvic acid + Shikimate 3-phosphate <> 5-O-(1-Carboxyvinyl)-3-phosphoshikimate + Phosphate Adenosine triphosphate + Shikimic acid <> ADP + Shikimate 3-phosphate Shikimic acid + Adenosine triphosphate > Hydrogen ion + Shikimate 3-phosphate + ADP Phosphoenolpyruvic acid + Shikimate 3-phosphate > Inorganic phosphate + 5-O-(1-Carboxyvinyl)-3-phosphoshikimate Adenosine triphosphate + Shikimic acid > ADP + Shikimate 3-phosphate Shikimic acid + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + shikimate 3-phosphate + ADP + Shikimate 3-phosphate shikimate 3-phosphate + Phosphoenolpyruvic acid + Shikimate 3-phosphate > Phosphate + 5-enolpyruvyl-shikimate 3-phosphate Adenosine triphosphate + Shikimic acid <> ADP + Hydrogen ion + Shikimate 3-phosphate
SMPDB Pathways:	Chorismate biosynthesis PW000816
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 splash10-0002-9420000000-24bff48841e0db52f23d View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0a4r-2290000000-396028b52ce4cedbe2bb View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-05n0-0490000000-529105b5a87b738ed617 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0002-6900000000-1e7071aa820eeb1c46ba View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-0udi-3190000000-efb4ce7028884fa42743 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9320000000-de7c749cb1ef8f00a7c2 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-5ea8917f66ef1d382869 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004j-9010000000-3906ab4aee0305db4d4b View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-004i-9010000000-6a75ffa6c3d07241a675 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-004i-9000000000-9bbc041a48805948beff View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-052r-0490000000-6f7f3bbe06a56485d8f7 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-052r-1950000000-f9d939de49ab972591e9 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-0aps-9000000000-a548a26753cac7a078d4 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:	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 Priestman, M. A., Healy, M. L., Becker, A., Alberg, D. G., Bartlett, P. A., Lushington, G. H., Schonbrunn, E. (2005). "Interaction of phosphonate analogues of the tetrahedral reaction intermediate with 5-enolpyruvylshikimate-3-phosphate synthase in atomic detail." Biochemistry 44:3241-3248. Pubmed: 15736934 Priestman, M. A., Healy, M. L., Funke, T., Becker, A., Schonbrunn, E. (2005). "Molecular basis for the glyphosate-insensitivity of the reaction of 5-enolpyruvylshikimate 3-phosphate synthase with shikimate." FEBS Lett 579:5773-5780. Pubmed: 16225867 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. Pubmed: 17765195 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 17052 HMDB ID HMDB0301781 Pubchem Compound ID 1095 Kegg ID C03175 ChemSpider ID 108789 Wikipedia ID Not Available BioCyc ID SHIKIMATE-5P EcoCyc ID SHIKIMATE-5P Ligand Expo S3P

Enzymes