U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of PREPHENIC ACID

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

Approval Year

PubMed

PubMed

TitleDatePubMed
Mapping of chorismate mutase and prephenate dehydrogenase domains in the Escherichia coli T-protein.
2003 Feb
Investigation of solvent effects for the Claisen rearrangement of chorismate to prephenate: mechanistic interpretation via near attack conformations.
2003 Jun 4
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 May 14
Just a near attack conformer for catalysis (chorismate to prephenate rearrangements in water, antibody, enzymes, and their mutants).
2003 Sep 3
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 Dec 15
Investigation of ligand binding and protein dynamics in Bacillus subtilis chorismate mutase by transverse relaxation optimized spectroscopy-nuclear magnetic resonance.
2005 May 10
Multiple-steering QM-MM calculation of the free energy profile in chorismate mutase.
2005 May 18
Vitamin K1 accumulation in tobacco plants overexpressing bacterial genes involved in the biosynthesis of salicylic acid.
2007 Jan 30
Mechanism and plasticity of isochorismate pyruvate lyase: a computational study.
2009 Nov 11
Investigation of anticapsin biosynthesis reveals a four-enzyme pathway to tetrahydrotyrosine in Bacillus subtilis.
2010 Feb 9
Patents
Name Type Language
PREPHENIC ACID
MI  
Common Name English
CIS-1-CARBOXY-4-HYDROXY-.ALPHA.-OXO-2,5-CYCLOHEXADIENE-1-PROPANOIC ACID
Common Name English
PREPHENIC ACID [MI]
Common Name English
PREPHENIC ACID, CIS
Common Name English
Code System Code Type Description
CHEBI
16666
Created by admin on Sat Dec 16 04:19:12 GMT 2023 , Edited by admin on Sat Dec 16 04:19:12 GMT 2023
PRIMARY
FDA UNII
Z66B98Z97I
Created by admin on Sat Dec 16 04:19:12 GMT 2023 , Edited by admin on Sat Dec 16 04:19:12 GMT 2023
PRIMARY
CAS
126-49-8
Created by admin on Sat Dec 16 04:19:12 GMT 2023 , Edited by admin on Sat Dec 16 04:19:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID60894109
Created by admin on Sat Dec 16 04:19:12 GMT 2023 , Edited by admin on Sat Dec 16 04:19:12 GMT 2023
PRIMARY
CAS
87664-40-2
Created by admin on Sat Dec 16 04:19:12 GMT 2023 , Edited by admin on Sat Dec 16 04:19:12 GMT 2023
ALTERNATIVE
DRUG BANK
DB08427
Created by admin on Sat Dec 16 04:19:12 GMT 2023 , Edited by admin on Sat Dec 16 04:19:12 GMT 2023
PRIMARY
MERCK INDEX
m9126
Created by admin on Sat Dec 16 04:19:12 GMT 2023 , Edited by admin on Sat Dec 16 04:19:12 GMT 2023
PRIMARY Merck Index
WIKIPEDIA
PREPHENIC ACID
Created by admin on Sat Dec 16 04:19:12 GMT 2023 , Edited by admin on Sat Dec 16 04:19:12 GMT 2023
PRIMARY
CHEBI
84387
Created by admin on Sat Dec 16 04:19:12 GMT 2023 , Edited by admin on Sat Dec 16 04:19:12 GMT 2023
PRIMARY
PUBCHEM
1028
Created by admin on Sat Dec 16 04:19:12 GMT 2023 , Edited by admin on Sat Dec 16 04:19:12 GMT 2023
PRIMARY