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


Isochorismate (M2MDB001009)

Record Information
Version2.0
Creation Date2012-05-31 14:30:47 -0600
Update Date2015-09-17 15:41:51 -0600
Secondary Accession Numbers
  • ECMDB20162
Identification
Name:Isochorismate
DescriptionIsochorismate is a member of the chemical class known as Beta Hydroxy Acids and Derivatives. These are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom. In Escherichia coli, isochorismate is a common precursor for the biosynthesis of the siderophore enterobactin and menaquinone (vitamin K2). Isochorismate is formed by the shikimate pathway from chorismate by the enzyme isochorismate synthase encoded by the entC gene. (PMID 8655506)
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms:
  • Iso-chorismate
  • Iso-chorismic acid
  • Isochorismic acid
Chemical Formula:C10H8O6
Weight:Average: 224.169
Monoisotopic: 224.033185137
InChI Key:NTGWPRCCOQCMGE-YUMQZZPRSA-L
InChI:InChI=1S/C10H10O6/c1-5(9(12)13)16-7-4-2-3-6(8(7)11)10(14)15/h2-4,7-8,11H,1H2,(H,12,13)(H,14,15)/p-2/t7-,8-/m0/s1
CAS number:22642-82-6
IUPAC Name:(5S,6S)-5-[(1-carboxyeth-1-en-1-yl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid
Traditional IUPAC Name:isochorismic acid
SMILES:[H][C@]1(O)C(=CC=C[C@]1([H])OC(=C)C([O-])=O)C([O-])=O
Chemical Taxonomy
Description belongs to the class of organic compounds known as beta hydroxy acids and derivatives. Beta hydroxy acids and derivatives are compounds containing a carboxylic acid substituted with a hydroxyl group on the C3 carbon atom.
KingdomOrganic compounds
Super ClassOrganic acids and derivatives
ClassHydroxy acids and derivatives
Sub ClassBeta hydroxy acids and derivatives
Direct ParentBeta hydroxy acids and derivatives
Alternative Parents
Substituents
  • Beta-hydroxy acid
  • Dicarboxylic acid or derivatives
  • Secondary alcohol
  • 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
  • 5-[(1-carboxyethenyl)oxy]-6-hydroxycyclohexa-1,3-diene-1-carboxylic acid (CHEBI:17582 )
Physical Properties
State:Not Available
Charge:-2
Melting point:Not Available
Experimental Properties:
PropertyValueSource
Predicted Properties
PropertyValueSource
Water Solubility10.4 g/LALOGPS
logP0.69ALOGPS
logP-0.13ChemAxon
logS-1.3ALOGPS
pKa (Strongest Acidic)3.39ChemAxon
pKa (Strongest Basic)-3.6ChemAxon
Physiological Charge-2ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area104.06 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity54.31 m³·mol⁻¹ChemAxon
Polarizability20.37 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Biological Properties
Cellular Locations:Cytoplasm
Reactions:
Chorismate <> Isochorismate
Water + Isochorismate <> (2S,3S)-2,3-Dihydro-2,3-dihydroxybenzoate + Pyruvic acid
alpha-Ketoglutarate + Hydrogen ion + Isochorismate <> 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide
Isochorismate + alpha-Ketoglutarate <> 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide
Hydrogen ion + Isochorismate + Oxoglutaric acid > 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide
Isochorismate + Water > 2,3-dihydroxy-2,3-dihydrobenzoate + Pyruvic acid
Chorismate > Isochorismate
Isochorismate + Oxoglutaric acid > 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate + Carbon dioxide
Chorismate > isochorismate + Isochorismate
Water + isochorismate + Isochorismate > Pyruvic acid + 2,3-dihydroxy-2,3-dihydrobenzoate
isochorismate + Oxoglutaric acid + Hydrogen ion + Isochorismate > Carbon dioxide + 2-Succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate
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
Enterobactin BiosynthesisPW002048 ThumbThumb?image type=greyscaleThumb?image type=simple
Menaquinol biosythesisPW001897 ThumbThumb?image type=greyscaleThumb?image type=simple
KEGG Pathways:
  • Biosynthesis of siderophore group nonribosomal peptides ec01053
  • Metabolic pathways eco01100
  • Ubiquinone and other terpenoid-quinone biosynthesis ec00130
EcoCyc Pathways:
  • 1,4-dihydroxy-2-naphthoate biosynthesis I PWY-5837
  • 2,3-dihydroxybenzoate biosynthesis PWY-5901
Concentrations
Not Available
Spectra
Spectra:
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0390000000-442c352acb8b551f3122View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4r-2930000000-ce3efa1e6faec0da376bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-059i-9800000000-340536fab24636b175d4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-004i-2790000000-f3ace46a88beae78abf7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a5i-2920000000-ab6fd49186f9e64db922View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-06rl-6900000000-d2314c10e3a03441539fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-00dr-0900000000-241fe41a6cb87fa3a745View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0079-0900000000-3ca3dca83527af19b555View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0536-9300000000-f0bcd9ed15657be962ecView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-053i-1900000000-6d5bafcfd1495f0951c1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-08g3-2900000000-24982517f03249357ae9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-01pc-4900000000-9d508a5a0ed2c89cc844View 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
  • Kwon, O., Hudspeth, M. E., Meganathan, R. (1996). "Anaerobic biosynthesis of enterobactin Escherichia coli: regulation of entC gene expression and evidence against its involvement in menaquinone (vitamin K2) biosynthesis." J Bacteriol 178:3252-3259. Pubmed: 8655506
  • 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 ID29780
HMDB IDHMDB0304395
Pubchem Compound ID189062
Kegg IDC00885
ChemSpider ID787
Wikipedia IDNot Available
BioCyc IDISOCHORISMATE
EcoCyc IDISOCHORISMATE
Ligand ExpoISC

Enzymes

Protein Details
1. Isochorismatase
General function:
Involved in isochorismatase activity
Specific function:
Required for production of 2,3-DHB. Also serves as an aryl carrier protein and plays a role in enterobactin assembly
Gene Name:
entB
Uniprot ID:
P0ADI4
Molecular weight:
32554
Reactions
Isochorismate + H(2)O = 2,3-dihydroxy-2,3-dihydrobenzoate + pyruvate.
Protein Details
2. Isochorismate synthase entC
General function:
Involved in biosynthetic process
Specific function:
Chorismate = isochorismate
Gene Name:
entC
Uniprot ID:
P0AEJ2
Molecular weight:
42931
Reactions
Chorismate = isochorismate.
Protein Details
3. 2-succinyl-5-enolpyruvyl-6-hydroxy-3-cyclohexene-1-carboxylate synthase
General function:
Involved in thiamine pyrophosphate binding
Specific function:
Catalyzes the thiamine diphosphate-dependent decarboxylation of 2-oxoglutarate and the subsequent addition of the resulting succinic semialdehyde-thiamine pyrophosphate anion to isochorismate to yield 2-succinyl-5-enolpyruvyl-6-hydroxy-3- cyclohexene-1-carboxylate (SEPHCHC)
Gene Name:
menD
Uniprot ID:
P17109
Molecular weight:
61367
Reactions
Isochorismate + 2-oxoglutarate = 5-enolpyruvoyl-6-hydroxy-2-succinyl-cyclohex-3-ene-1-carboxylate + CO(2).
Protein Details
4. Menaquinone-specific isochorismate synthase
General function:
Involved in biosynthetic process
Specific function:
Chorismate = isochorismate
Gene Name:
menF
Uniprot ID:
P38051
Molecular weight:
48764
Reactions
Chorismate = isochorismate.