Record Information
Version2.0
Creation Date2012-05-31 14:32:26 -0600
Update Date2015-09-17 15:42:00 -0600
Secondary Accession Numbers
  • ECMDB20193
Identification
Name:Shikimate 3-phosphate
DescriptionShikimate 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
Thumb
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassOrganic phosphoric acids and derivatives
Sub ClassPhosphate esters
Direct ParentMonoalkyl phosphates
Alternative Parents
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 FrameworkAliphatic homomonocyclic compounds
External Descriptors
Physical Properties
State:Not Available
Charge:-3
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility21 g/LALOGPS
logP-2.1ALOGPS
logP-1.8ChemAxon
logS-1.1ALOGPS
pKa (Strongest Acidic)1.32ChemAxon
pKa (Strongest Basic)-3.2ChemAxon
Physiological Charge-3ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area144.52 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity49.83 m³·mol⁻¹ChemAxon
Polarizability20.46 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:
  • 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, Positivesplash10-0002-9420000000-24bff48841e0db52f23dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-2290000000-396028b52ce4cedbe2bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-0490000000-529105b5a87b738ed617View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-6900000000-1e7071aa820eeb1c46baView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3190000000-efb4ce7028884fa42743View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9320000000-de7c749cb1ef8f00a7c2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5ea8917f66ef1d382869View in MoNA
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
External Links:
ResourceLink
CHEBI ID17052
HMDB IDNot Available
Pubchem Compound ID1095
Kegg IDC03175
ChemSpider ID108789
Wikipedia IDNot Available
BioCyc IDSHIKIMATE-5P
EcoCyc IDSHIKIMATE-5P
Ligand ExpoS3P

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 shikimate kinase activity
Specific function:
Catalyzes the specific phosphorylation of the 3-hydroxyl group of shikimic acid using ATP as a cosubstrate
Gene Name:
aroK
Uniprot ID:
P0A6D7
Molecular weight:
19538
Reactions
ATP + shikimate = ADP + shikimate 3-phosphate.
General function:
Involved in shikimate kinase activity
Specific function:
Catalyzes the specific phosphorylation of the 3-hydroxyl group of shikimic acid using ATP as a cosubstrate
Gene Name:
aroL
Uniprot ID:
P0A6E1
Molecular weight:
19151
Reactions
ATP + shikimate = ADP + shikimate 3-phosphate.