3-Phosphoshikimic acid (YMDB00332)

Identification
YMDB IDYMDB00332
Name3-Phosphoshikimic acid
SpeciesSaccharomyces cerevisiae
StrainBaker's yeast
Description3-Phosphoshikimic acid is an intermediate in the chorismate biosynthesis pathway also called shikimate pathway. This pathway occurs in plants and microorganisms. Chorismate is an important intermediate that leads to the biosynthesis of several essential metabolites, including the aromatic amino acids L-phenylalanine, L-tyrosine and L-tryptophan, vitamins E and K, ubiquinone and certain siderophore. [Biocyc ARO-PWY]
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
  • Shikimate 3-phosphate
  • Shikimate 5-phosphate
  • Shikimic acid 3-phosphoric acid
  • Shikimic acid 5-phosphoric acid
  • Shikimic acid-3-phosphoric acid
  • 3-Phosphoshikimate
  • Shikimic acid-3-phosphate
CAS number63959-45-5
WeightAverage: 254.1312
Monoisotopic: 254.01915384
InChI KeyQYOJSKGCWNAKGW-PBXRRBTRSA-N
InChIInChI=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)/t4-,5-,6+/m1/s1
IUPAC Name(3R,4S,5R)-4,5-dihydroxy-3-(phosphonooxy)cyclohex-1-ene-1-carboxylic acid
Traditional IUPAC Name3-phosphoshikimic acid
Chemical FormulaC7H11O8P
SMILESO[C@@H]1CC(=C[C@@H](OP(O)(O)=O)[C@H]1O)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
StateNot Available
Charge0
Melting pointNot Available
Experimental Properties
PropertyValueReference
Water SolubilityNot AvailablePhysProp
LogPNot AvailablePhysProp
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
Organoleptic PropertiesNot Available
SMPDB PathwaysNot Available
KEGG Pathways
Phenylalanine, tyrosine and tryptophan biosynthesisec00400 Map00400
SMPDB ReactionsNot Available
KEGG Reactions
Phosphoenolpyruvic acid + 3-Phosphoshikimic acid → phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimic acid
Adenosine triphosphate + Shikimic acid → 3-Phosphoshikimic acid + hydron + ADP
Concentrations
Intracellular ConcentrationsNot Available
Extracellular ConcentrationsNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0002-9420000000-24bff48841e0db52f23dJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4r-2290000000-396028b52ce4cedbe2bbJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-05n0-0490000000-529105b5a87b738ed617JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0002-6900000000-1e7071aa820eeb1c46baJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-3190000000-efb4ce7028884fa42743JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9320000000-de7c749cb1ef8f00a7c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-5ea8917f66ef1d382869JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004j-9010000000-3906ab4aee0305db4d4bJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-004i-9010000000-6a75ffa6c3d07241a675JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9000000000-9bbc041a48805948beffJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0490000000-6f7f3bbe06a56485d8f7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-1950000000-f9d939de49ab972591e9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0aps-9000000000-a548a26753cac7a078d4JSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
1D NMR13C NMR SpectrumNot AvailableJSpectraViewer
1D NMR1H NMR SpectrumNot AvailableJSpectraViewer
References
References:
  • UniProt Consortium (2011). "Ongoing and future developments at the Universal Protein Resource." Nucleic Acids Res 39:D214-D219.21051339
  • Scheer, M., Grote, A., Chang, A., Schomburg, I., Munaretto, C., Rother, M., Sohngen, C., Stelzer, M., Thiele, J., Schomburg, D. (2011). "BRENDA, the enzyme information system in 2011." Nucleic Acids Res 39:D670-D676.21062828
  • Herrgard, M. J., Swainston, N., Dobson, P., Dunn, W. B., Arga, K. Y., Arvas, M., Bluthgen, N., Borger, S., Costenoble, R., Heinemann, M., Hucka, M., Le Novere, N., Li, P., Liebermeister, W., Mo, M. L., Oliveira, A. P., Petranovic, D., Pettifer, S., Simeonidis, E., Smallbone, K., Spasic, I., Weichart, D., Brent, R., Broomhead, D. S., Westerhoff, H. V., Kirdar, B., Penttila, M., Klipp, E., Palsson, B. O., Sauer, U., Oliver, S. G., Mendes, P., Nielsen, J., Kell, D. B. (2008). "A consensus yeast metabolic network reconstruction obtained from a community approach to systems biology." Nat Biotechnol 26:1155-1160.18846089
  • Larimer, F. W., Morse, C. C., Beck, A. K., Cole, K. W., Gaertner, F. H. (1983). "Isolation of the ARO1 cluster gene of Saccharomyces cerevisiae." Mol Cell Biol 3:1609-1614.6355828
Synthesis Reference:Not Available
External Links:
ResourceLink
CHEBI ID17052
HMDB IDHMDB0301781
Pubchem Compound ID121947
Kegg IDC03175
ChemSpider ID23096204
FOODB IDFDB001398
Wikipedia IDNot Available
BioCyc IDNot Available

Enzymes

Protein Details
1. Pentafunctional AROM polypeptide
General function:
Involved in 3-dehydroquinate dehydratase activity
Specific function:
The AROM polypeptide catalyzes 5 consecutive enzymatic reactions in prechorismate polyaromatic amino acid biosynthesis
Gene Name:
ARO1
Uniprot ID:
P08566
Molecular weight:
174754.0
Reactions
3-deoxy-D-arabino-hept-2-ulosonate 7-phosphate → 3-dehydroquinate + phosphate.
3-dehydroquinate → 3-dehydroshikimate + H(2)O.
Shikimate + NADP(+) → 3-dehydroshikimate + NADPH.
ATP + shikimate → ADP + shikimate 3-phosphate.
Phosphoenolpyruvate + 3-phosphoshikimate → phosphate + 5-O-(1-carboxyvinyl)-3-phosphoshikimate.