digeranyl bisphosphonate   Click here for help

GtoPdb Ligand ID: 3187

PDB Ligand
Compound class: Synthetic organic
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 12
Topological polar surface area 134.68
Molecular weight 448.21
XLogP 3.43
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CC(=CCC(P(=O)(O)O)(P(=O)(O)O)CC=C(CCC=C(C)C)C)CCC=C(C)C
Isomeric SMILES C/C(=C\CC(P(=O)(O)O)(P(=O)(O)O)C/C=C(/CCC=C(C)C)\C)/CCC=C(C)C
InChI InChI=1S/C21H38O6P2/c1-17(2)9-7-11-19(5)13-15-21(28(22,23)24,29(25,26)27)16-14-20(6)12-8-10-18(3)4/h9-10,13-14H,7-8,11-12,15-16H2,1-6H3,(H2,22,23,24)(H2,25,26,27)/b19-13+,20-14+
InChI Key SQERRIVHBWCION-IWGRKNQJSA-N
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
geranylgeranyl diphosphate synthase Hs Inhibitor Inhibition 6.0 – 6.7 pIC50 - 1-2
pIC50 6.7 (IC50 2x10-7 M) [2]
Description: recombinant human protein expressed in BL21 gold bacteria, purified, in vitro assay
Conditions: pH 7.5, 37°C. Substrate concentrations: 20µM FPP, 40µM IPP and 207micro;M GPP.
pIC50 6.0 [1]
Description: Inhibition of human recombinant geranylgeranyl diphosphate synthase
Conditions: pH 7.0, 37°C. Concentration of substrate: 25µM FPP or GPP