GGsTop   Click here for help

GtoPdb Ligand ID: 10265

Compound class: Synthetic organic
Comment: GGsTop is a nontoxic, and irreversible inhibitor of γ-glutamyltransferase (γ-glutamyl transpeptidase) [1] (it is phosphonate diester 5a in this reference). The compound has two stereogenic centers and therefore has the potential to exist in 4 stereoisomeric forms [2]. We show the structure without specified stereochemistry to represent the racemic mixture.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 7
Hydrogen bond donors 3
Rotatable bonds 9
Topological polar surface area 145.96
Molecular weight 331.08
XLogP -2.03
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES COP(=O)(Oc1cccc(c1)CC(=O)O)CCC(C(=O)O)N
Isomeric SMILES COP(=O)(Oc1cccc(c1)CC(=O)O)CCC(C(=O)O)N
InChI InChI=1S/C13H18NO7P/c1-20-22(19,6-5-11(14)13(17)18)21-10-4-2-3-9(7-10)8-12(15)16/h2-4,7,11H,5-6,8,14H2,1H3,(H,15,16)(H,17,18)
InChI Key NTFPDEDRMYYPAC-UHFFFAOYSA-N
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
γ-Glutamyltransferase Hs Inhibitor Inhibition 3.8 pKi - 1
pKi 3.8 (Ki 1.7x10-4 M) [1]
Description: pKa= 9.71