trans,trans-farnesyl diphosphate   Click here for help

GtoPdb Ligand ID: 3050

Synonyms: (E,E)-farnesyl diphosphate | all-trans-farnesyl pyrophosphate | farnesyl diphosphate | FPP | trans-farnesyl pyrophosphate
PDB Ligand
Compound class: Metabolite
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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 11
Topological polar surface area 132.91
Molecular weight 382.13
XLogP 1.89
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CC(=CCOP(=O)(OP(=O)(O)O)O)CCC=C(CCC=C(C)C)C
Isomeric SMILES C/C(=C\COP(=O)(OP(=O)(O)O)O)/CC/C=C(/CCC=C(C)C)\C
InChI InChI=1S/C15H28O7P2/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-21-24(19,20)22-23(16,17)18/h7,9,11H,5-6,8,10,12H2,1-4H3,(H,19,20)(H2,16,17,18)/b14-9+,15-11+
InChI Key VWFJDQUYCIWHTN-YFVJMOTDSA-N
Natural/Endogenous Targets
Target
mevalonate kinase
Enzymes Catalysing Reactions with this Compound as a Substrate or Product
Enzyme EC number Reaction Reference
geranylgeranyl diphosphate synthase 3-4
squalene synthase 5,7
farnesyl diphosphate synthase
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
mevalonate kinase Ligand is endogenous in the given species Hs Inhibitor Feedback inhibition 7.0 – 7.5 pKi - 1-2
pKi 7.5 (Ki 3.4x10-8 M) [1]
Description: recombinant wild type enzyme expressed in E coli, in vitro spectrophotometric assay
Conditions: 30°C, pH 7.5; 0.5-11µM (R,S)-mevalonic acid, 6mM ATP
pKi 7.0 (Ki 1.01x10-7 M) [2]
Description: recombinant enzyme expressed in E coli cells. Spectrophotometric assay
Conditions: pH 7.0, 25°C. Concentration of mevalonate fixed and saturating; ATP varied between 0.16-5mM
mevalonate kinase Ligand is endogenous in the given species Rn Inhibitor Feedback inhibition 5.6 – 6.5 pKi - 6,8
pKi 6.5 (Ki 3.48x10-7 M) [8]
Description: spectrophotometric in vitro assay
Conditions: Substrate concentrations: ATP concentration varied from 0.02-5mM, mevalonate concentration vaired from 0.02 to 0.6mM
pKi 5.6 (Ki 2.5x10-6 M) [6]
Description: in vitro, spectrophotometric assay
Conditions: pH 7.0, 25°C. Concentration of FPP varied (2µM and 6µM). MgATP2- concentration varied between 0.2-2mM.