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BioAssay: AID 151017

Binding affinity against ornithine transcarbamoylase (OTC) produced by Streptococcus faecalis The buffer taken for this study is 50 mM Tris.HCl, 0.5 mM EDTA at pH 8.0.

Diverse alpha-methyl-substituted phosphonylphosphinates (P-C-P-C-X) are accessible from a protected, pentafluorophenylsulfonated phosphonylphosphinate via nucleophilic displacement. The utility of this route is demonstrated with several nitrogen nucleophiles. The resulting amine and amino acid phosphonylphosphinate derivatives were evaluated as inhibitors of Streptococcus faecalis ornithine more ..
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 Tested Compounds
 Tested Compounds
All(8)
 
 
Active(1)
 
 
Unspecified(7)
 
 
 Tested Substances
 Tested Substances
All(8)
 
 
Active(1)
 
 
Unspecified(7)
 
 
 Related BioAssays
 Related BioAssays
AID: 151017
Data Source: ChEMBL (148264)
Depositor Category: Literature, Extracted
BioAssay Version:
Deposit Date: 2010-05-24
Modify Date: 2013-11-14

Data Table ( Complete ):           Active    All
BioActive Compound: 1
Description:
Title: alpha-Functionalized phosphonylphosphinates: synthesis and evaluation as transcarbamoylase inhibitors.

Abstract: Diverse alpha-methyl-substituted phosphonylphosphinates (P-C-P-C-X) are accessible from a protected, pentafluorophenylsulfonated phosphonylphosphinate via nucleophilic displacement. The utility of this route is demonstrated with several nitrogen nucleophiles. The resulting amine and amino acid phosphonylphosphinate derivatives were evaluated as inhibitors of Streptococcus faecalis ornithine transcarbamoylase (OTC). Compared with the structurally related phosphonoacetyl-L-ornithine (L-PALO), a known inhibitor of OTCs from various sources, the phosphonylphosphinates are surprisingly poor inhibitors, binding several orders of magnitude less tightly to the enzyme. These results suggest that the tetrahedral intermediate formed in the normal transcarbamoylase reaction is poorly mimicked by a tetrahedral and anionic phosphonate, either because of directly unfavorable interactions with a hydrogen-bond acceptor within the active site or because transition-state analogues are unable to induce the protein conformation changes that normally accompany reaction.
(PMID: 10411483)
Comment
Compounds with activity <= 50uM or explicitly reported as active by ChEMBL are flagged as active in this PubChem assay presentation.

Putative Target:

ChEMBL Target ID: 11547
Target Type: SINGLE PROTEIN
Pref Name: Ornithine carbamoyltransferase
Synonyms: Ornithine carbamoyltransferase; mitochondrial;Ornithine transcarbamylase;OTCase;
Gene Name: OTC;
Protein Accession: P00480;
Protein GI: 84028235;
Organism: Homo sapiens
Tax ID: 9606
Target Classification: enzyme
Confidence: Homologous single protein target assigned
Relationship Type: Homologous protein target assigned
Categorized Comment
ChEMBL Assay Type: Binding

ChEMBL Assay Data Source: Scientific Literature

Result Definitions
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TIDNameDescriptionHistogramTypeUnit
OutcomeThe BioAssay activity outcomeOutcome
1Ki*Ki PubChem standard valueFloatμM
2BEIBinding Efficiency Index(nM)Float
3SEISurface Efficiency Index(nM)Float
4LELigand EfficiencyFloat
5LLELipophilic Ligand EfficiencyFloat
6Ki activity commentKi activity commentString
7Ki standard flagKi standard flagInteger
8Ki qualifierKi qualifierString
9Ki published valueKi published valueFloatμM
10Ki standard valueKi standard valueFloatnM
11Ki data validityKi data validityString

* Activity Concentration.

Data Table (Concise)
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