PREPHENIC 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=C[C@](CC(=O)C(O)=O)(C=C1)C(O)=O

InChI

InChIKey=FPWMCUPFBRFMLH-XGAOUMNUSA-N

InChI=1S/C10H10O6/c11-6-1-3-10(4-2-6,9(15)16)5-7(12)8(13)14/h1-4,6,11H,5H2,(H,13,14)(H,15,16)/t6-,10+

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
Prephenate decarboxylases: a new prephenate-utilizing enzyme family that performs nonaromatizing decarboxylation en route to diverse secondary metabolites.	2010-10-26	20863139
Investigation of anticapsin biosynthesis reveals a four-enzyme pathway to tetrahydrotyrosine in Bacillus subtilis.	2010-02-09	20052993
Role of Bacillus subtilis BacB in the synthesis of bacilysin.	2009-11-13	19776011
Mechanism and plasticity of isochorismate pyruvate lyase: a computational study.	2009-11-11	19835359
Genetic and biochemical identification of the chorismate mutase from Corynebacterium glutamicum.	2009-10	19589834
On-the-path random walk sampling for efficient optimization of minimum free-energy path.	2009-08	19462399
Phenylalanine biosynthesis in Arabidopsis thaliana. Identification and characterization of arogenate dehydratases.	2007-10-19	17726025
Vitamin K1 accumulation in tobacco plants overexpressing bacterial genes involved in the biosynthesis of salicylic acid.	2007-01-30	17084477
Computer-aided rational design of catalytic antibodies: The 1F7 case.	2007	17124715
Multiple-steering QM-MM calculation of the free energy profile in chorismate mutase.	2005-05-18	15884923
Investigation of ligand binding and protein dynamics in Bacillus subtilis chorismate mutase by transverse relaxation optimized spectroscopy-nuclear magnetic resonance.	2005-05-10	15865424
Differential transition-state stabilization in enzyme catalysis: quantum chemical analysis of interactions in the chorismate mutase reaction and prediction of the optimal catalytic field.	2004-12-15	15584751
Just a near attack conformer for catalysis (chorismate to prephenate rearrangements in water, antibody, enzymes, and their mutants).	2003-09-03	12940735
Investigation of solvent effects for the Claisen rearrangement of chorismate to prephenate: mechanistic interpretation via near attack conformations.	2003-06-04	12769575
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
Efficiency of lignin biosynthesis: a quantitative analysis.	2003-05	12714366
Understanding the role of active-site residues in chorismate mutase catalysis from molecular-dynamics simulations.	2003-04-04	12698486
Mapping of chorismate mutase and prephenate dehydrogenase domains in the Escherichia coli T-protein.	2003-02	12581215
The emerging periplasm-localized subclass of AroQ chorismate mutases, exemplified by those from Salmonella typhimurium and Pseudomonas aeruginosa.	2001	11532214

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 21:21:55 GMT 2025` Edited by `admin` on `Mon Mar 31 21:21:55 GMT 2025`
Record UNII	Z66B98Z97I
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CIS-1-CARBOXY-4-HYDROXY-.ALPHA.-OXO-2,5-CYCLOHEXADIENE-1-PROPANOIC ACID

Preferred Name

English

PREPHENIC ACID

Common Name

English

PREPHENIC ACID [MI]

Common Name

English

PREPHENIC ACID, CIS

Common Name

English

Code System Code Type Description

CHEBI

16666