CHORISMIC ACID

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H10O6
Molecular Weight	226.1828
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O[C@@H]1C=CC(=C[C@H]1OC(=C)C(O)=O)C(O)=O

InChI

InChIKey=WTFXTQVDAKGDEY-HTQZYQBOSA-N

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

HIDE SMILES / InChI

Molecular Formula	C10H10O6
Molecular Weight	226.1828
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
Identification of 4-amino-4-deoxychorismate synthase as the molecular target for the antimicrobial action of (6s)-6-fluoroshikimate.	2004-08-18	15303852
A homotropic two-state model and auto-antagonism.	2004-07-16	15257759
Para-position derivatives of fungal anthelmintic cyclodepsipeptides engineered with Streptomyces venezuelae antibiotic biosynthetic genes.	2004-07	15184904
Conformational effects in enzyme catalysis: QM/MM free energy calculation of the 'NAC' contribution in chorismate mutase.	2004-05-21	15136856
Deciphering enzymes. Genetic selection as a probe of structure and mechanism.	2004-05	15096202
Transition state stabilization and substrate strain in enzyme catalysis: ab initio QM/MM modelling of the chorismate mutase reaction.	2004-04-07	15034619
Abyssomicins, inhibitors of the para-aminobenzoic acid pathway produced by the marine Verrucosispora strain AB-18-032.	2004-04	15217192
Nuclear import of yeast Gcn4p requires karyopherins Srp1p and Kap95p.	2004-04	14648200
Mechanism of chorismate synthase. Role of the two invariant histidine residues in the active site.	2004-03-05	14668332
Conservation of mechanism in three chorismate-utilizing enzymes.	2004-03-03	14982443
Chorismate mutase of Thermus thermophilus is a monofunctional AroH class enzyme inhibited by tyrosine.	2004-03	14727008
Crystal structure of chorismate synthase: a novel FMN-binding protein fold and functional insights.	2004-02-27	15095868
Theoretical insights in enzyme catalysis.	2004-02-20	14767505
Network analysis of metabolic enzyme evolution in Escherichia coli.	2004-02-18	15113413
Structure of the OmpA-like domain of RmpM from Neisseria meningitidis.	2004-02	14763978
A comparative study of claisen and cope rearrangements catalyzed by chorismate mutase. An insight into enzymatic efficiency: transition state stabilization or substrate preorganization?	2004-01-14	14709097
Crystal structure of the bifunctional chorismate synthase from Saccharomyces cerevisiae.	2004-01-02	14573601
In vitro reconstitution of rice anthranilate synthase: distinct functional properties of the alpha subunits OASA1 and OASA2.	2004-01	15159631
The purification, crystallization and preliminary structural characterization of PhzF, a key enzyme in the phenazine-biosynthesis pathway from Pseudomonas fluorescens 2-79.	2004-01	14684924
New enzymes from combinatorial library modules.	2004	15289064
In silico identification and experimental validation of PmrAB targets in Salmonella typhimurium by regulatory motif detection.	2004	14759259
Quantitative evaluation of noncovalent chorismate mutase-inhibitor binding by ESI-MS.	2003-12	14652193
Steady-state kinetics and molecular evolution of Escherichia coli MenD [(1R,6R)-2-succinyl-6-hydroxy-2,4-cyclohexadiene-1-carboxylate synthase], an anomalous thiamin diphosphate-dependent decarboxylase-carboligase.	2003-11-25	14621995
(De)regulation of key enzyme steps in the shikimate pathway and phenylalanine-specific pathway of the actinomycete Amycolatopsis methanolica.	2003-11	14600244
Crystal structure of Mycobacterium tuberculosis MenB, a key enzyme in vitamin K2 biosynthesis.	2003-10-24	12909628
(S,S)-2,3-Dihydroxy-2,3-dihydrobenzoic acid: microbial access with engineered cells of Escherichia coli and application as starting material in natural-product synthesis.	2003-09-05	12953204
Just a near attack conformer for catalysis (chorismate to prephenate rearrangements in water, antibody, enzymes, and their mutants).	2003-09-03	12940735
Apparent NAC effect in chorismate mutase reflects electrostatic transition state stabilization.	2003-08-27	12926945
Easy access to (R,R)-3,4-dihydroxy-3,4-dihydrobenzoic acid with engineered strains of Escherichia coli.	2003-08-04	12898630
The salicylic acid loop in plant defense.	2003-08	12873532
An engineered chorismate mutase with allosteric regulation.	2003-07-17	12818673
Contributions of conformational compression and preferential transition state stabilization to the rate enhancement by chorismate mutase.	2003-06-11	12783541
Investigation of solvent effects for the Claisen rearrangement of chorismate to prephenate: mechanistic interpretation via near attack conformations.	2003-06-04	12769575
Regulation of anthraquinone biosynthesis in cell cultures of Morinda citrifolia.	2003-06	12872482
A novel strategy for the assignment of side-chain resonances in completely deuterated large proteins using 13C spectroscopy.	2003-06	12766412
Structure and mechanism of Pseudomonas aeruginosa PhzD, an isochorismatase from the phenazine biosynthetic pathway.	2003-05-20	12741825
HutC/FarR-like bacterial transcription factors of the GntR family contain a small molecule-binding domain of the chorismate lyase fold.	2003-05-16	12757941
Comparison of formation of reactive conformers (NACs) for the Claisen rearrangement of chorismate to prephenate in water and in the E. coli mutase: the efficiency of the enzyme catalysis.	2003-05-14	12733937
Charge optimization increases the potency and selectivity of a chorismate mutase inhibitor.	2003-05-14	12733875
Isochorismate synthase (PchA), the first and rate-limiting enzyme in salicylate biosynthesis of Pseudomonas aeruginosa.	2003-05-09	12624097
A chorismate mutase from the soybean cyst nematode Heterodera glycines shows polymorphisms that correlate with virulence.	2003-05	12744515
Genetic organization of an Acinetobacter baumannii chromosomal region harbouring genes related to siderophore biosynthesis and transport.	2003-05	12724384
Quinic acid induces hypovirulence and expression of a hypovirulence-associated double-stranded RNA in Rhizoctonia solani.	2003-05	12695850
Understanding the role of active-site residues in chorismate mutase catalysis from molecular-dynamics simulations.	2003-04-04	12698486
On the generation of catalytic antibodies by transition state analogues.	2003-04-04	12672107
Selective stabilization of the chorismate mutase transition state by a positively charged hydrogen bond donor.	2003-03-19	12630863
Construction and complementation of the first auxotrophic mutant in the spirochaete Leptospira meyeri.	2003-03	12634337
QM/MM calculations of kinetic isotope effects in the chorismate mutase active site.	2003-02-07	12926249
A new strategy for backbone resonance assignment in large proteins using a MQ-HACACO experiment.	2003-02	12652123
Horizontally transferred genes in plant-parasitic nematodes: a high-throughput genomic approach.	2003	12801413

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:13:31 GMT 2025` Edited by `admin` on `Mon Mar 31 19:13:31 GMT 2025`
Record UNII	GI1BLY82Y1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CHORISMIC ACID [MI]

Preferred Name

English

CHORISMIC ACID

Common Name

English

(3R,4R)-3-((1-CARBOXYETHENYL)OXY)-4-HYDROXY-1,5-CYCLOHEXADIENE-1-CARBOXYLIC ACID

Systematic Name

English

Code System Code Type Description

WIKIPEDIA

CHORISMIC ACID