Detailed information for compound 81581

Basic information

Technical information
  • TDR Targets ID: 81581
  • Name: [1-hydroxy-3-[methyl(4-phenylbutyl)amino]-1-p hosphonopropyl]phosphonic acid
  • MW: 381.298 | Formula: C14H25NO7P2
  • H donors: 5 H acceptors: 7 LogP: -3.25 Rotable bonds: 10
    Rule of 5 violations (Lipinski): 1
  • SMILES: CN(CCC(P(=O)(O)O)(P(=O)(O)O)O)CCCCc1ccccc1
  • InChi: 1S/C14H25NO7P2/c1-15(11-6-5-9-13-7-3-2-4-8-13)12-10-14(16,23(17,18)19)24(20,21)22/h2-4,7-8,16H,5-6,9-12H2,1H3,(H2,17,18,19)(H2,20,21,22)
  • InChiKey: VFLFYDXGZMGUAF-UHFFFAOYSA-N  


Substructure search Similarity search

Network

Hover on a compound node to display the structore

Synonyms

  • [1-hydroxy-3-[methyl(4-phenylbutyl)amino]-1-phosphono-propyl]phosphonic acid
  • [1-hydroxy-3-(methyl-(4-phenylbutyl)amino)-1-phosphonopropyl]phosphonic acid
  • [1-hydroxy-3-(methyl-(4-phenylbutyl)amino)-1-phosphono-propyl]phosphonic acid
  • 129951-00-4
  • N-[methyl(4-phenylbutyl)]-3-aminopropyl-1-hydroxy-1,1-bispho sphonate (disodium, hydrate)
  • NSC724490

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens farnesyl diphosphate synthase Starlite/ChEMBL References
Escherichia coli geranyltranstransferase Starlite/ChEMBL References
Homo sapiens geranylgeranyl diphosphate synthase 1 Starlite/ChEMBL References
Leishmania donovani farnesyl pyrophosphate synthase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Chlamydia trachomatis geranylgeranyl pyrophosphate synthase Get druggable targets OG5_130660 All targets in OG5_130660
Leishmania donovani polyprenyl synthase, putative Get druggable targets OG5_129071 All targets in OG5_129071
Leishmania braziliensis farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Mycobacterium tuberculosis Probable multifunctional geranylgeranyl pyrophosphate synthetase IdsA1 (GGPP synthetase) (ggppsase) (geranylgeranyl diphosphate Get druggable targets OG5_130660 All targets in OG5_130660
Brugia malayi geranylgeranyl pyrophosphate synthetase Get druggable targets OG5_129071 All targets in OG5_129071
Trypanosoma brucei farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Echinococcus multilocularis farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Echinococcus granulosus geranylgeranyl pyrophosphate synthase Get druggable targets OG5_129071 All targets in OG5_129071
Leishmania infantum farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Leishmania donovani farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Candida albicans similar to S. cerevisiae ERG20 (YJL167W) farnesyl diphosphate synthetase (FPP synthetase) Get druggable targets OG5_127590 All targets in OG5_127590
Loa Loa (eye worm) polyprenyl synthetase Get druggable targets OG5_127590 All targets in OG5_127590
Toxoplasma gondii polyprenyl synthetase superfamily protein Get druggable targets OG5_127590 All targets in OG5_127590
Trichomonas vaginalis geranylgeranyl diphosphate synthase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Schistosoma japonicum ko:K00787 dimethylallyltranstransferase [EC2.5.1.1], putative Get druggable targets OG5_129071 All targets in OG5_129071
Cryptosporidium hominis farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Mycobacterium tuberculosis Probable geranylgeranyl pyrophosphate synthetase IdsA2 (ggppsase) (GGPP synthetase) (geranylgeranyl diphosphate synthase) Get druggable targets OG5_127590 All targets in OG5_127590
Trypanosoma congolense farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Schistosoma japonicum ko:K00787 dimethylallyltranstransferase [EC2.5.1.1], putative Get druggable targets OG5_127590 All targets in OG5_127590
Schistosoma mansoni geranylgeranyl pyrophosphate synthase Get druggable targets OG5_129071 All targets in OG5_129071
Leishmania infantum polyprenyl synthase, putative Get druggable targets OG5_129071 All targets in OG5_129071
Plasmodium berghei geranylgeranyl pyrophosphate synthase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Trypanosoma congolense Hydroxyneurosporene synthase (CrtC)/Polyprenyl synthetase, putative Get druggable targets OG5_129071 All targets in OG5_129071
Theileria parva farnesyl pyrophosphate synthetase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Brugia malayi Polyprenyl synthetase family protein Get druggable targets OG5_127590 All targets in OG5_127590
Mycobacterium tuberculosis Possible polyprenyl synthetase IdsB (polyprenyl transferase) (polyprenyl diphosphate synthase) Get druggable targets OG5_130660 All targets in OG5_130660
Treponema pallidum octaprenyl-diphosphate synthase Get druggable targets OG5_129071 All targets in OG5_129071
Mycobacterium ulcerans polyprenyl synthetase IdsB Get druggable targets OG5_130660 All targets in OG5_130660
Loa Loa (eye worm) geranylgeranyl pyrophosphate synthetase Get druggable targets OG5_129071 All targets in OG5_129071
Plasmodium falciparum geranylgeranyl pyrophosphate synthase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Giardia lamblia Farnesyl diphosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Candida albicans similar to S. cerevisiae ERG20 (YJL167W) farnesyl diphosphate synthetase (FPP synthetase) Get druggable targets OG5_127590 All targets in OG5_127590
Trichomonas vaginalis geranylgeranyl pyrophosphate synthase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Babesia bovis farnesyl pyrophosphate synthetase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Schistosoma japonicum Geranylgeranyl pyrophosphate synthetase, putative Get druggable targets OG5_129071 All targets in OG5_129071
Leishmania major farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Leishmania mexicana farnesyl pyrophosphate synthase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Trypanosoma cruzi polyprenyl synthase, putative Get druggable targets OG5_129071 All targets in OG5_129071
Cryptosporidium parvum putative farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Leishmania mexicana polyprenyl synthase, putative Get druggable targets OG5_129071 All targets in OG5_129071
Plasmodium knowlesi geranylgeranyl pyrophosphate synthase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Mycobacterium ulcerans geranylgeranyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Plasmodium vivax geranylgeranyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Schistosoma mansoni farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Trypanosoma cruzi farnesyl pyrophosphate synthase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Candida albicans geranylgeranyl diphosphate synthase Get druggable targets OG5_129071 All targets in OG5_129071
Echinococcus granulosus farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Trypanosoma brucei gambiense farnesyl pyrophosphate synthase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Leishmania braziliensis polyprenyl synthase, putative Get druggable targets OG5_129071 All targets in OG5_129071
Trichomonas vaginalis geranylgeranyl pyrophosphate synthase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Trypanosoma cruzi polyprenyl synthase, putative Get druggable targets OG5_129071 All targets in OG5_129071
Trypanosoma cruzi farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Leishmania major polyprenyl synthase, putative Get druggable targets OG5_129071 All targets in OG5_129071
Mycobacterium ulcerans geranylgeranyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Echinococcus multilocularis geranylgeranyl pyrophosphate synthase Get druggable targets OG5_129071 All targets in OG5_129071
Neospora caninum hypothetical protein Get druggable targets OG5_127590 All targets in OG5_127590
Plasmodium yoelii farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Wolbachia endosymbiont of Brugia malayi geranylgeranyl pyrophosphate synthase Get druggable targets OG5_130660 All targets in OG5_130660
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Plasmodium falciparum geranylgeranyl pyrophosphate synthase, putative geranylgeranyl diphosphate synthase 1 300 aa 317 aa 21.4 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Mycobacterium ulcerans geranylgeranyl pyrophosphate synthase 0.0310185 1 1
Mycobacterium tuberculosis Probable geranylgeranyl pyrophosphate synthetase IdsA2 (ggppsase) (GGPP synthetase) (geranylgeranyl diphosphate synthase) 0.0310185 1 1
Trichomonas vaginalis geranylgeranyl diphosphate synthase, putative 0.0310185 1 0.5
Chlamydia trachomatis geranylgeranyl pyrophosphate synthase 0.0257063 0.0641265 0.5
Schistosoma mansoni farnesyl pyrophosphate synthase 0.0310185 1 1
Wolbachia endosymbiont of Brugia malayi geranylgeranyl pyrophosphate synthase 0.0257063 0.0641265 0.5
Trypanosoma brucei farnesyl pyrophosphate synthase 0.0310185 1 0.5
Trichomonas vaginalis geranylgeranyl pyrophosphate synthase, putative 0.0310185 1 0.5
Toxoplasma gondii polyprenyl synthetase superfamily protein 0.0310185 1 0.5
Brugia malayi Polyprenyl synthetase family protein 0.0310185 1 1
Leishmania major farnesyl pyrophosphate synthase 0.0310185 1 1
Giardia lamblia Farnesyl diphosphate synthase 0.0310185 1 0.5
Mycobacterium ulcerans geranylgeranyl pyrophosphate synthase 0.0310185 1 1
Loa Loa (eye worm) polyprenyl synthetase 0.0310185 1 1
Trypanosoma cruzi farnesyl pyrophosphate synthase, putative 0.0310185 1 1
Echinococcus multilocularis farnesyl pyrophosphate synthase 0.0310185 1 1
Trypanosoma cruzi farnesyl pyrophosphate synthase 0.0310185 1 1
Treponema pallidum octaprenyl-diphosphate synthase 0.0253423 0 0.5
Plasmodium vivax geranylgeranyl pyrophosphate synthase 0.0310185 1 0.5
Echinococcus granulosus farnesyl pyrophosphate synthase 0.0310185 1 1
Trichomonas vaginalis geranylgeranyl pyrophosphate synthase, putative 0.0310185 1 0.5
Plasmodium falciparum geranylgeranyl pyrophosphate synthase, putative 0.0310185 1 0.5

Activities

Activity type Activity value Assay description Source Reference
Decrease (functional) = 26 % Percent decrease of normal liver weight (mg) in Entameoba histolyctica infected hamsters (treated at 10 mg/kg ip once a day for 5 days) ChEMBL. 14695831
Decrease (functional) = 89 % Percent decrease of amebic liver abscess (mg) formation in Entameoba histolyctica infected hamsters (treated at 10 mg/kg ip once a day for 5 days) ChEMBL. 14695831
ED50 (functional) = 0.4 ug kg-1 Effective dose in inhibiting osteoclastic bone resorption ChEMBL. 12825934
ED50 (functional) = 0.4 ug kg-1 Effective dose after subcutaneous administration to TPTX rats for 50% reduction of hypercalcemia ChEMBL. 12166945
ED50 (functional) = 0.4 ug kg-1 Effective dose in inhibiting osteoclastic bone resorption ChEMBL. 12825934
IC50 (functional) = -8.98 Negative logarithm of inhibitory concentration against bone resorption ChEMBL. 12825934
IC50 (binding) = -6.31 Inhibitory activity against farnesyl Pyrophosphate Synthase expressed as #NAME? (M) ChEMBL. 14613320
IC50 (binding) = 5.4 Inhibition of human recombinant geranylgeranyl diphosphate synthase ChEMBL. 18800762
IC50 (functional) = 5.5 Growth inhibition of Plasmodium falciparum ChEMBL. 19053772
IC50 (binding) = 0.49 uM Inhibitory activity against Leishmania major Farnesyl diphosphate synthase ChEMBL. 14695831
IC50 (binding) = 0.49 uM Inhibitory activity against farnesyl Pyrophosphate Synthase was determined ChEMBL. 14613320
IC50 (binding) = 0.49 uM Inhibitory activity against Leishmania major Farnesyl diphosphate synthase ChEMBL. 14695831
IC50 (binding) = 0.49 uM Inhibitory activity against farnesyl Pyrophosphate Synthase was determined ChEMBL. 14613320
IC50 (binding) = 1.3 uM Inhibition of Escherichia coli FPPS ChEMBL. 17149863
IC50 (binding) = 1.3 uM Inhibition of Escherichia coli FPPS ChEMBL. 17149863
IC50 (functional) = 2.9 uM In vitro growth inhibition against Plasmodium falciparum ChEMBL. 14695831
IC50 (functional) = 2.9 uM In vitro growth inhibition against Plasmodium falciparum ChEMBL. 14695831
IC50 (functional) = 2.9 uM Growth inhibition of Plasmodium falciparum ChEMBL. 19053772
IC50 (binding) = 4.17 uM Inhibition of human recombinant geranylgeranyl diphosphate synthase ChEMBL. 18800762
IC50 (functional) = 22.9 uM Antiproliferative activity against human NCI-H460 cell line by MTT assay ChEMBL. 16970405
IC50 (functional) = 22.9 uM Antiproliferative activity against human NCI-H460 cell line by MTT assay ChEMBL. 16970405
IC50 (functional) = 23.4 uM In vitro growth inhibition against Entamoeba histolytica ChEMBL. 14695831
IC50 (functional) = 23.4 uM In vitro growth inhibition against Entamoeba histolytica ChEMBL. 14695831
IC50 (functional) = 33 uM Antibacterial activity against Escherichia coli K12 by broth microdilution method ChEMBL. 17149863
IC50 (functional) = 33 uM Antibacterial activity against Escherichia coli K12 by broth microdilution method ChEMBL. 17149863
IC50 (functional) = 49.2 uM Antiproliferative activity against human SF-268 cell line by MTT assay ChEMBL. 16970405
IC50 (functional) = 49.2 uM Antiproliferative activity against human SF-268 cell line by MTT assay ChEMBL. 16970405
IC50 (functional) = 82.5 uM Antiproliferative activity against human MCF7 cell line by MTT assay ChEMBL. 16970405
IC50 (functional) = 82.5 uM Antiproliferative activity against human MCF7 cell line by MTT assay ChEMBL. 16970405
IC50 (binding) = 245 uM Inhibition of E. coli DXR ChEMBL. 17149863
IC50 (binding) = 245 uM Inhibition of E. coli DXR ChEMBL. 17149863
IC50 (binding) = 444 uM Inhibition of T. brucei FPPSexpressed in E. coli ChEMBL. 17149863
IZ (functional) = 17 mm Antibacterial activity against Escherichia coli pTMV19 in presence of mevalonate ChEMBL. 17149863
IZ (functional) = 17 mm Antibacterial activity against Escherichia coli pTMV19 in presence of mevalonate ChEMBL. 17149863
IZ (functional) = 18 mm Antibacterial activity against Escherichia coli pTMV19 ChEMBL. 17149863
IZ (functional) = 18 mm Antibacterial activity against Escherichia coli pTMV19 ChEMBL. 17149863
IZ (functional) = 19 mm Antibacterial activity against Escherichia coli W3110 ChEMBL. 17149863
IZ (functional) = 19 mm Antibacterial activity against Escherichia coli W3110 ChEMBL. 17149863
Ki (binding) = 0.046 uM Binding affinity towards farnesyl Pyrophosphate Synthase using [14C]- isopentenyl pyrophosphate as radioligand ChEMBL. 14613320
Ki (binding) = 0.046 uM Binding affinity towards farnesyl Pyrophosphate Synthase using [14C]- isopentenyl pyrophosphate as radioligand ChEMBL. 14613320
LD50 (ADMET) > 690 uM Toxicity evaluated against human nasopharyngeal carcinoma KB cell line ChEMBL. 14695831
LD50 (ADMET) > 690 uM Toxicity evaluated against human nasopharyngeal carcinoma KB cell line ChEMBL. 14695831
Log IC50 (binding) = 6.31 Inhibitory activity against farnesyl Pyrophosphate Synthase expressed as #NAME? (M) ChEMBL. 14613320
Log IC50 (functional) = 8.97900000000001 Negative logarithm of inhibitory concentration against bone resorption ChEMBL. 12825934
MBC (functional) = 625 uM Antibacterial activity against Escherichia coli K12 in presence of fosmidomycin ChEMBL. 17149863
MBC (functional) = 625 uM Antibacterial activity against Escherichia coli K12 in presence of fosmidomycin ChEMBL. 17149863
MBC (functional) = 1250 uM Antibacterial activity against Escherichia coli K12 ChEMBL. 17149863
MBC (functional) = 1250 uM Antibacterial activity against Escherichia coli K12 ChEMBL. 17149863
Mean effect (functional) = 94 mg Mean effect on amebic liver abscess (mg) formation in Entameoba histolyctica infected hamsters (treated at 10 mg/kg ip once a day for 5 days) ChEMBL. 14695831
Mean effect (functional) = 1756 mg Mean effect on normal liver weight (mg) in Entameoba histolyctica infected hamsters (treated at 10 mg/kg ip once a day for 5 days) ChEMBL. 14695831
MIC (functional) = 156 uM Antibacterial activity against Escherichia coli K12 ChEMBL. 17149863
MIC (functional) = 156 uM Antibacterial activity against Escherichia coli K12 ChEMBL. 17149863
MIC (functional) = 312 uM Antibacterial activity against Escherichia coli K12 in presence of fosmidomycin ChEMBL. 17149863
MIC (functional) = 312 uM Antibacterial activity against Escherichia coli K12 in presence of fosmidomycin ChEMBL. 17149863
Ratio (functional) = 0.13 Ratio, MIC/MBC for Escherichia coli K12 ChEMBL. 17149863
Ratio (functional) = 0.5 Ratio, MIC/MBC for Escherichia coli K12 in presence of fosmidomycin ChEMBL. 17149863
TI (ADMET) > 29.5 Therapeutic index was expressed as ratio of LD50 for KB cell line to IC50 against Entamoeba histolytica ChEMBL. 14695831
TI (ADMET) > 238 Therapeutic index was expressed as ratio of LD50 for KB cell line to IC50 against Plasmodium falciparum ChEMBL. 14695831

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Plasmodium falciparum ChEMBL23 14695831

Many chemical entities in TDR Targets come from high-throughput screenings with whole cells or tissue samples, and not all assayed compounds have been tested against a single a single target protein, probably because they get ruled out during screening process. Even if these compounds may have not been of interest in the original screening, they may come as interesting leads for other screening assays. Furthermore, we may be able to propose drug-target associations using chemical similarities and network patterns.

Annotated phenotypes:

We have no manually annotated phenotypes for this drug. What does this mean? / Care to help?
In TDR Targets, information about phenotypes that are caused by drugs, or by genetic manipulation of cells (e.g. gene knockouts or knockdowns) is manually curated from the literature. These descriptions help to describe the potential of the target for drug development. If no information is available for this gene or if the information is incomplete, this may mean that i) the papers containing this information either appeared after the curation effort for this organism was carried out or they were inadvertently missed by curators; or that ii) the curation effort for this organism has not yet started.
 
In any case, if you have information about papers containing relevant validation data for this target, please log in using your TDR Targets username and password and send them to us using the corresponding form in this page (only visible to registered users) or contact us.

External resources for this compound

Bibliographic References

7 literature references were collected for this gene.

If you have references for this compound, please enter them in a user comment (below) or Contact us.