Record Information
Version2.0
Creation Date2012-05-31 14:21:02 -0600
Update Date2015-06-03 17:19:03 -0600
Secondary Accession Numbers
  • ECMDB12199
Identification
Name:Chorismate
DescriptionChorismic 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
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.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassCarboxylic acids and derivatives
Sub ClassDicarboxylic acids and derivatives
Direct ParentDicarboxylic acids and derivatives
Alternative Parents
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 FrameworkAliphatic 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 g/LALOGPS
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 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.31 m³·mol⁻¹ChemAxon
Polarizability20.49 ųChemAxon
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
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

SMPDB Pathways:
2,3-dihydroxybenzoate biosynthesisPW000751 ThumbThumb?image type=greyscaleThumb?image type=simple
Biosynthesis of siderophore group nonribosomal peptidesPW000760 ThumbThumb?image type=greyscaleThumb?image type=simple
Chorismate biosynthesisPW000816 ThumbThumb?image type=greyscaleThumb?image type=simple
Enterobactin BiosynthesisPW002048 ThumbThumb?image type=greyscaleThumb?image type=simple
Folate biosynthesisPW000908 ThumbThumb?image type=greyscaleThumb?image type=simple
Menaquinol biosythesisPW001897 ThumbThumb?image type=greyscaleThumb?image type=simple
Phenylalanine metabolismPW000921 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: Ubiquinol biosynthesisPW000981 ThumbThumb?image type=greyscaleThumb?image type=simple
Secondary Metabolites: Ubiquinol biosynthesis 2PW002036 ThumbThumb?image type=greyscaleThumb?image type=simple
Tryptophan metabolismPW000815 ThumbThumb?image type=greyscaleThumb?image type=simple
phenylalanine biosynthesisPW000807 ThumbThumb?image type=greyscaleThumb?image type=simple
tryptophan metabolism IIPW001916 ThumbThumb?image type=greyscaleThumb?image type=simple
tyrosine biosynthesisPW000806 ThumbThumb?image type=greyscaleThumb?image type=simple
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 TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-000i-8920000000-c9c1de401e53d5259b37View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (3 TMS) - 70eV, Positivesplash10-004i-7439400000-61898d5da9dfc83487d0View in MoNA
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

Enzymes

General function:
Involved in biosynthetic process
Specific function:
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:
trpE
Uniprot ID:
P00895
Molecular weight:
57494
Reactions
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate.
General function:
Involved in metabolic process
Specific function:
Catalyzes the biosynthesis of 4-amino-4-deoxychorismate (ADC) from chorismate and glutamine
Gene Name:
pabA
Uniprot ID:
P00903
Molecular weight:
20772
Reactions
Chorismate + L-glutamine = 4-amino-4-deoxychorismate + L-glutamate.
General function:
Involved in anthranilate phosphoribosyltransferase activity
Specific function:
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate
Gene Name:
trpD
Uniprot ID:
P00904
Molecular weight:
56869
Reactions
Chorismate + L-glutamine = anthranilate + pyruvate + L-glutamate.
N-(5-phospho-D-ribosyl)-anthranilate + diphosphate = anthranilate + 5-phospho-alpha-D-ribose 1-diphosphate.
General function:
Involved in biosynthetic process
Specific function:
Catalyzes the biosynthesis of 4-amino-4-deoxychorismate (ADC) from chorismate and glutamine
Gene Name:
pabB
Uniprot ID:
P05041
Molecular weight:
50969
Reactions
Chorismate + L-glutamine = 4-amino-4-deoxychorismate + L-glutamate.
General function:
Involved in oxidation-reduction process
Specific function:
Chorismate = prephenate
Gene Name:
tyrA
Uniprot ID:
P07023
Molecular weight:
42042
Reactions
Chorismate = prephenate.
Prephenate + NAD(+) = 4-hydroxyphenylpyruvate + CO(2) + NADH.
General function:
Involved in chorismate mutase activity
Specific function:
Chorismate = prephenate
Gene Name:
pheA
Uniprot ID:
P0A9J8
Molecular weight:
43111
Reactions
Chorismate = prephenate.
Prephenate = phenylpyruvate + H(2)O + CO(2).
General function:
Involved in biosynthetic process
Specific function:
Chorismate = isochorismate
Gene Name:
entC
Uniprot ID:
P0AEJ2
Molecular weight:
42931
Reactions
Chorismate = isochorismate.
General function:
Involved in chorismate synthase activity
Specific function:
5-O-(1-carboxyvinyl)-3-phosphoshikimate = chorismate + phosphate
Gene Name:
aroC
Uniprot ID:
P12008
Molecular weight:
39137
Reactions
5-O-(1-carboxyvinyl)-3-phosphoshikimate = chorismate + phosphate.
General function:
Involved in chorismate lyase activity
Specific function:
Removes the pyruvyl group from chorismate, with concomitant aromatization of the ring, to provide 4- hydroxybenzoate (4HB) for the ubiquinone pathway
Gene Name:
ubiC
Uniprot ID:
P26602
Molecular weight:
18777
Reactions
Chorismate = 4-hydroxybenzoate + pyruvate.
General function:
Involved in biosynthetic process
Specific function:
Chorismate = isochorismate
Gene Name:
menF
Uniprot ID:
P38051
Molecular weight:
48764
Reactions
Chorismate = isochorismate.