Structural search and advanced query search is temporarily unavailable. We are working to fix this issue. Thank you for your support and patience.

Record Information
Version	2.0
Creation Date	2012-05-31 14:21:02 -0600
Update Date	2015-06-03 17:19:03 -0600
Secondary Accession Numbers	ECMDB12199
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	MOLSDFPDBSMILESInChI × Structure for #<Compound:0xacda2670> Close
Synonyms:	Chorismic acid
Chemical Formula:	C10H10O6
Weight:	Average: 226.1828 Monoisotopic: 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
Description	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 Class	Organic acids and derivatives
Class	Carboxylic acids and derivatives
Sub Class	Dicarboxylic acids and derivatives
Direct Parent	Dicarboxylic acids and derivatives
Alternative Parents	Secondary alcohols Carboxylic acids Organic oxides Hydrocarbon derivatives Carbonyl compounds
Substituents	Dicarboxylic acid or derivatives Secondary alcohol Carboxylic acid Organic oxygen compound Organic oxide 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:	Property Value Source
Predicted Properties	Property Value Source Water Solubility 8.8 g/L ALOGPS logP 0.52 ALOGPS logP -0.13 ChemAxon logS -1.4 ALOGPS pKa (Strongest Acidic) 3.39 ChemAxon pKa (Strongest Basic) -3.4 ChemAxon Physiological Charge -2 ChemAxon Hydrogen Acceptor Count 6 ChemAxon Hydrogen Donor Count 3 ChemAxon Polar Surface Area 104.06 Ų ChemAxon Rotatable Bond Count 4 ChemAxon Refractivity 54.31 m³·mol⁻¹ ChemAxon Polarizability 20.49 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:	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 4-Hydroxybenzoic acid + Pyruvic acid <> Chorismate Chorismate + L-Glutamine > Hydrogen ion + 2-Aminobenzoic acid + Pyruvic acid + L-Glutamate 5-O-(1-Carboxyvinyl)-3-phosphoshikimate > Phosphate + Chorismate Chorismate > Prephenate Chorismate > 4-Hydroxybenzoic acid + Pyruvic acid 5-O-(1-Carboxyvinyl)-3-phosphoshikimate > Chorismate + Inorganic phosphate Chorismate > Isochorismate Chorismate + L-Glutamine > 4-Amino-4-deoxychorismate + L-Glutamate Chorismate + L-Glutamine > 2-Aminobenzoic acid + Pyruvic acid + L-Glutamate 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 Chorismate + L-Glutamine <>2 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acid Chorismate + Ammonia <>2 2-Aminobenzoic acid + Pyruvic acid + Water Chorismate + L-Glutamine <>4 4-Amino-4-deoxychorismate + L-Glutamate 5 5-O-(1-Carboxyvinyl)-3-phosphoshikimate <> Chorismate + Phosphate Chorismate <> Prephenate Chorismate + L-Glutamine <>2 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acid Chorismate + L-Glutamine <>2 2-Aminobenzoic acid + L-Glutamate + Hydrogen ion + Pyruvic acid Chorismate + L-Glutamine <>4 4-Amino-4-deoxychorismate + L-Glutamate Chorismate <> Prephenate More...
SMPDB Pathways:	2,3-dihydroxybenzoate biosynthesis PW000751 Biosynthesis of siderophore group nonribosomal peptides PW000760 Chorismate biosynthesis PW000816 Enterobactin Biosynthesis PW002048 Folate biosynthesis PW000908 Menaquinol biosythesis PW001897 Phenylalanine metabolism PW000921 Secondary Metabolites: Ubiquinol biosynthesis PW000981 Secondary Metabolites: Ubiquinol biosynthesis 2 PW002036 Tryptophan metabolism PW000815 phenylalanine biosynthesis PW000807 tryptophan metabolism II PW001916 tyrosine biosynthesis PW000806
KEGG Pathways:	Biosynthesis of siderophore group nonribosomal peptides ec01053 Folate biosynthesis ec00790 Metabolic pathways eco01100 Phenylalanine metabolism ec00360 Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 Tryptophan metabolism ec00380 Ubiquinone and other terpenoid-quinone biosynthesis ec00130
EcoCyc Pathways:	1,4-dihydroxy-2-naphthoate biosynthesis I PWY-5837 2,3-dihydroxybenzoate biosynthesis PWY-5901 4-hydroxybenzoate biosynthesis II (bacteria and fungi) PWY-5755 p-aminobenzoate biosynthesis PWY-6543 chorismate biosynthesis from 3-dehydroquinate PWY-6163 phenylalanine biosynthesis I PHESYN tryptophan biosynthesis TRPSYN-PWY tyrosine biosynthesis I TYRSYN
Concentrations
	Not Available
Spectra
Spectra:	Spectrum Type Description Splash Key Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive splash10-000i-8920000000-c9c1de401e53d5259b37 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positive splash10-004i-7439400000-61898d5da9dfc83487d0 View in MoNA Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer Predicted GC-MS Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive Not Available View in JSpectraViewer LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF 10V, positive splash10-0006-0900000000-b2b9deccbc523c6d0eab View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF 20V, positive splash10-0006-0900000000-c777d18079ce5f3f7cce View in MoNA LC-MS/MS LC-MS/MS Spectrum - LC-ESI-QTOF 40V, positive splash10-000f-9100000000-ce6e11131e810ac225a4 View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 3V, negative splash10-002r-0910000000-f6fbf6f220b47bb44d07 View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 4V, negative splash10-000i-0900000000-73859439e65b3b81c419 View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 5V, negative splash10-000i-0900000000-a7d9ad79c08c938f641d View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 7V, negative splash10-000i-0900000000-3b8ca1c03a2b18dcb3ee View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 10V, negative splash10-000i-1900000000-7cb1f442b1b4017f231c View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 15V, negative splash10-000i-5900000000-ab5c560af44c3e113890 View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 17V, negative splash10-000l-8900000000-188280d32d1c753f7e22 View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 20V, negative splash10-000l-9600000000-d42db1d206b7d8fe2555 View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 23V, negative splash10-000f-9200000000-e80c9b91e42c7ce5f07c View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 25V, negative splash10-0006-9200000000-88dbca436a340239632c View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 27V, negative splash10-0006-9100000000-9202017d9ac4e164e0df View in MoNA LC-MS/MS LC-MS/MS Spectrum - QTOF 30V, negative splash10-0006-9000000000-50c145d43aba50ec736f View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 1V, negative splash10-0570-0940000000-573c1187a2d4556bd2c1 View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 1V, negative splash10-0570-0930000000-fb6a26ac0db1fa8e3a5f View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 2V, negative splash10-004r-0920000000-5085342dabe01fc8bcab View in MoNA LC-MS/MS LC-MS/MS Spectrum - Orbitrap 2V, negative splash10-004r-0910000000-1ba87cb3a1e14ed46c1a View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Positive splash10-0a4i-1490000000-0c0be827ab9167718ec0 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Positive splash10-0a4r-2920000000-70cd182f84cfcb7bcc5c View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Positive splash10-052r-6900000000-4c4eaa55fb7ee94f5725 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 10V, Negative splash10-004i-1590000000-38a825366167edaea080 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 20V, Negative splash10-0a4r-2920000000-e4d23a3d35bdaecc1db4 View in MoNA Predicted LC-MS/MS Predicted LC-MS/MS Spectrum - 40V, Negative splash10-06rl-6900000000-c88f4ed01c10938fc50a 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 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 17333 HMDB ID HMDB12199 Pubchem Compound ID 12039 Kegg ID C00251 ChemSpider ID 11542 Wikipedia ID Chorismic_acid BioCyc ID CHORISMATE EcoCyc ID CHORISMATE Ligand Expo ISJ

Enzymes