Chorismate (PAMDB000828)

IdentificationTaxonomyPhysical PropertiesBiological PropertiesSpectraConcentrationsLinksReferencesEnzymes Transporters
Proteins (3280)
Record Information
Version 1.0
Update Date 1/22/2018 11:54:54 AM
Metabolite IDPAMDB000828
Identification
Name: Chorismate
Description:Chorismic acid, more commonly known as its anionic form chorismate, is an important biochemical intermediate in plants and microorganisms. It is a precursor for the aromatic amino acids phenylalanine and tyrosine,indole, indole derivatives and tryptophan,2,3-dihydroxybenzoic acid (DHB) used for enterobactin biosynthesis,the plant hormone salicylic acid and many alkaloids and other aromatic metabolites. -- Wikipedia
Structure
Thumb
🔍MOLSDFPDBSMILESInChIView Structure
Synonyms:
  • Chorismic acid
Chemical Formula: C10H10O6
Average Molecular Weight: 226.1828
Monoisotopic Molecular Weight: 226.047738052
InChI Key: WTFXTQVDAKGDEY-HTQZYQBOSA-N
InChI:InChI=1S/C10H10O6/c1-5(9(12)13)16-8-4-6(10(14)15)2-3-7(8)11/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/t7-,8-/m1/s1
CAS number: 55508-12-8
IUPAC Name:(3R,4R)-3-[(1-carboxyeth-1-en-1-yl)oxy]-4-hydroxycyclohexa-1,5-diene-1-carboxylic acid
Traditional IUPAC Name: chorismic acid
SMILES:O[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=O
Chemical Taxonomy
Taxonomy DescriptionThis compound belongs to the class of organic compounds known as dicarboxylic acids and derivatives. These are organic compounds containing exactly two carboxylic acid groups.
Kingdom Organic compounds
Super ClassOrganic acids and derivatives
Class Carboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct Parent Dicarboxylic acids and derivatives
Alternative Parents
Substituents
  • Dicarboxylic acid or derivatives
  • Cyclic alcohol
  • Secondary alcohol
  • Carboxylic acid
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homomonocyclic compound
Molecular Framework Aliphatic homomonocyclic compounds
External Descriptors
  • 5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid (CHEBI:17333 )
Physical Properties
State: Solid
Charge:-2
Melting point: 140 ?C
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility8.8 mg/mLALOGPS
logP0.52ALOGPS
logP-0.13ChemAxon
logS-1.4ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-3.4ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.31 m3·mol-1ChemAxon
Polarizability20.49 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations: Cytoplasm
Reactions:
Chorismate + L-Glutamine <> 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acid
Chorismate <> Prephenate
Chorismate + L-Glutamine <> 4-Amino-4-deoxychorismate + L-Glutamate
Chorismate <> Isochorismate
5-O-(1-Carboxyvinyl)-3-phosphoshikimate <> Chorismate + Phosphate
Chorismate <> 4-Hydroxybenzoic acid + Pyruvic acid
Chorismate + Ammonia <> 2-Aminobenzoic acid + Pyruvic acid + Water
Chorismate + L-Glutamine <> 2-Aminobenzoic acid + Pyruvic acid + L-Glutamate
5-O-(1-Carboxyvinyl)-3-phosphoshikimate > Chorismate + Inorganic phosphate
Chorismate > isochorismate + Isochorismate
Chorismate + L-Glutamine > L-Glutamic acid + Pyruvic acid + Hydrogen ion + 2-Aminobenzoic acid + L-Glutamate
5-enolpyruvyl-shikimate 3-phosphate > Phosphate + Chorismate
Chorismate + L-Glutamine > L-Glutamic acid + 4-amino-4-deoxychorismate + L-Glutamate + 4-Amino-4-deoxychorismate
More...

Pathways:
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MSNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-1490000000-0c0be827ab9167718ec0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-2920000000-70cd182f84cfcb7bcc5cView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-052r-6900000000-4c4eaa55fb7ee94f5725View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-1590000000-38a825366167edaea080View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4r-2920000000-e4d23a3d35bdaecc1db4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rl-6900000000-c88f4ed01c10938fc50aView 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
  • 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 ID17333
HMDB IDHMDB12199
Pubchem Compound ID12039
Kegg IDC00251
ChemSpider ID11542
Wikipedia IDChorismic acid
BioCyc IDCHORISMATE
EcoCyc IDCHORISMATE
Ligand ExpoISJ