Detailed information for compound 77937

Basic information

Technical information
  • TDR Targets ID: 77937
  • Name: (1-hydroxy-1-phosphonohexyl)phosphonic acid
  • MW: 262.135 | Formula: C6H16O7P2
  • H donors: 5 H acceptors: 7 LogP: -1.7 Rotable bonds: 6
    Rule of 5 violations (Lipinski): 1
  • SMILES: CCCCCC(P(=O)(O)O)(P(=O)(O)O)O
  • InChi: 1S/C6H16O7P2/c1-2-3-4-5-6(7,14(8,9)10)15(11,12)13/h7H,2-5H2,1H3,(H2,8,9,10)(H2,11,12,13)
  • InChiKey: LBPHBRVNBKGYTP-UHFFFAOYSA-N  


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Synonyms

  • (1-hydroxy-1-phosphono-hexyl)phosphonic acid

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Trypanosoma brucei gambiense vacuolar-type proton translocating pyrophosphatase 1, putative References
Trypanosoma brucei Pyrophosphate-energized vacuolar membrane proton pump 1 Starlite/ChEMBL References
Leishmania donovani farnesyl pyrophosphate synthase Starlite/ChEMBL References
Homo sapiens farnesyl diphosphate synthase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Trypanosoma brucei Pyrophosphate-energized vacuolar membrane proton pump 2, putative Get druggable targets OG5_128905 All targets in OG5_128905
Plasmodium knowlesi vacuolar-type H+-translocating inorganic pyrophosphatase, putative Get druggable targets OG5_128905 All targets in OG5_128905
Trypanosoma brucei gambiense farnesyl pyrophosphate synthase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Trypanosoma brucei farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Leishmania braziliensis farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Cryptosporidium parvum putative farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Toxoplasma gondii V-type H(+)-translocating pyrophosphatase VP1 Get druggable targets OG5_128905 All targets in OG5_128905
Candida albicans similar to S. cerevisiae ERG20 (YJL167W) farnesyl diphosphate synthetase (FPP synthetase) Get druggable targets OG5_127590 All targets in OG5_127590
Leishmania infantum vacuolar-type proton translocating pyrophosphatase 1, putative Get druggable targets OG5_128905 All targets in OG5_128905
Trypanosoma cruzi vacuolar-type proton translocating pyrophosphatase 1 Get druggable targets OG5_128905 All targets in OG5_128905
Brugia malayi Polyprenyl synthetase family protein Get druggable targets OG5_127590 All targets in OG5_127590
Plasmodium berghei geranylgeranyl pyrophosphate synthase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Theileria parva farnesyl pyrophosphate synthetase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Plasmodium berghei inorganic pyrophosphatase, putative Get druggable targets OG5_128905 All targets in OG5_128905
Leishmania braziliensis vacuolar-type proton translocating pyrophosphatase 1, putative Get druggable targets OG5_128905 All targets in OG5_128905
Mycobacterium tuberculosis Probable geranylgeranyl pyrophosphate synthetase IdsA2 (ggppsase) (GGPP synthetase) (geranylgeranyl diphosphate synthase) Get druggable targets OG5_127590 All targets in OG5_127590
Echinococcus granulosus farnesyl pyrophosphate synthase 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
Neospora caninum hypothetical protein Get druggable targets OG5_128905 All targets in OG5_128905
Trypanosoma congolense farnesyl pyrophosphate synthase 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 knowlesi V-type H(+)-translocating pyrophosphatase, putative Get druggable targets OG5_128905 All targets in OG5_128905
Leishmania major farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Trypanosoma brucei Pyrophosphate-energized vacuolar membrane proton pump 1 Get druggable targets OG5_128905 All targets in OG5_128905
Leishmania infantum farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Plasmodium falciparum V-type K+-independent H+-translocating inorganic pyrophosphatase Get druggable targets OG5_128905 All targets in OG5_128905
Trichomonas vaginalis geranylgeranyl pyrophosphate synthase, putative 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
Plasmodium falciparum V-type H(+)-translocating pyrophosphatase, putative Get druggable targets OG5_128905 All targets in OG5_128905
Trichomonas vaginalis geranylgeranyl diphosphate synthase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Trypanosoma cruzi Vacuolar proton pyrophosphatase 1, putative Get druggable targets OG5_128905 All targets in OG5_128905
Trypanosoma brucei gambiense vacuolar-type proton translocating pyrophosphatase 1 Get druggable targets OG5_128905 All targets in OG5_128905
Neospora caninum hypothetical protein 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
Plasmodium berghei V-type H(+)-translocating pyrophosphatase, putative Get druggable targets OG5_128905 All targets in OG5_128905
Plasmodium falciparum geranylgeranyl pyrophosphate synthase, putative 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
Plasmodium vivax vacuolar-type H+ pumping pyrophosphatase, putative Get druggable targets OG5_128905 All targets in OG5_128905
Leishmania mexicana vacuolar-type proton translocating pyrophosphatase 1, putative Get druggable targets OG5_128905 All targets in OG5_128905
Cryptosporidium hominis farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Plasmodium knowlesi geranylgeranyl pyrophosphate synthase, putative 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
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
Plasmodium vivax geranylgeranyl pyrophosphate synthase 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
Leishmania mexicana farnesyl pyrophosphate synthase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Trypanosoma brucei gambiense vacuolar-type proton translocating pyrophosphatase 1, putative Get druggable targets OG5_128905 All targets in OG5_128905
Trypanosoma congolense vacuolar-type proton translocating pyrophosphatase 1 Get druggable targets OG5_128905 All targets in OG5_128905
Plasmodium yoelii vacuolar-type H+ pumping pyrophosphatase-related Get druggable targets OG5_128905 All targets in OG5_128905
Babesia bovis farnesyl pyrophosphate synthetase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Trypanosoma cruzi farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Leishmania major vacuolar-type proton translocating pyrophosphatase 1, putative Get druggable targets OG5_128905 All targets in OG5_128905
Plasmodium vivax V-type H(+)-translocating pyrophosphatase, putative Get druggable targets OG5_128905 All targets in OG5_128905
Leishmania donovani Pyrophosphate-energized vacuolar membrane proton pump 1, putative Get druggable targets OG5_128905 All targets in OG5_128905
Schistosoma japonicum ko:K00787 dimethylallyltranstransferase [EC2.5.1.1], 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
Trichomonas vaginalis geranylgeranyl pyrophosphate synthase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Plasmodium yoelii V-type H(+)-translocating pyrophosphatase Get druggable targets OG5_128905 All targets in OG5_128905
By sequence similarity to non orthologous known druggable targets
No druggable targets predicted by sequence similarity
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Brugia malayi Polyprenyl synthetase family protein 0.0247685 0 0.5
Leishmania major vacuolar-type proton translocating pyrophosphatase 1, putative 0.0542081 1 1
Schistosoma mansoni farnesyl pyrophosphate synthase 0.0247685 0 0.5
Loa Loa (eye worm) polyprenyl synthetase 0.0247685 0 0.5
Giardia lamblia Farnesyl diphosphate synthase 0.0247685 0 0.5
Trypanosoma cruzi Vacuolar proton pyrophosphatase 1, putative 0.0542081 1 1
Mycobacterium ulcerans geranylgeranyl pyrophosphate synthase 0.0247685 0 0.5
Trypanosoma cruzi vacuolar-type proton translocating pyrophosphatase 1 0.0542081 1 1
Plasmodium falciparum V-type K+-independent H+-translocating inorganic pyrophosphatase 0.0542081 1 1
Toxoplasma gondii V-type H(+)-translocating pyrophosphatase VP1 0.0542081 1 1
Echinococcus multilocularis farnesyl pyrophosphate synthase 0.0247685 0 0.5
Plasmodium vivax vacuolar-type H+ pumping pyrophosphatase, putative 0.0542081 1 1
Trichomonas vaginalis geranylgeranyl diphosphate synthase, putative 0.0247685 0 0.5
Mycobacterium ulcerans geranylgeranyl pyrophosphate synthase 0.0247685 0 0.5
Trichomonas vaginalis geranylgeranyl pyrophosphate synthase, putative 0.0247685 0 0.5
Mycobacterium tuberculosis Probable geranylgeranyl pyrophosphate synthetase IdsA2 (ggppsase) (GGPP synthetase) (geranylgeranyl diphosphate synthase) 0.0247685 0 0.5
Trypanosoma brucei Pyrophosphate-energized vacuolar membrane proton pump 2, putative 0.0542081 1 1
Echinococcus granulosus farnesyl pyrophosphate synthase 0.0247685 0 0.5
Plasmodium vivax V-type H(+)-translocating pyrophosphatase, putative 0.0542081 1 1
Trypanosoma brucei Pyrophosphate-energized vacuolar membrane proton pump 1 0.0542081 1 1
Plasmodium falciparum V-type H(+)-translocating pyrophosphatase, putative 0.0542081 1 1
Trichomonas vaginalis geranylgeranyl pyrophosphate synthase, putative 0.0247685 0 0.5

Activities

Activity type Activity value Assay description Source Reference
ED50 (functional) = 107 uM Dose of the compound to inhibit the growth of human KB carcinoma cell line ChEMBL. 16162013
ED50 (functional) = 107 uM Dose of the compound to inhibit the growth of human KB carcinoma cell line ChEMBL. 16162013
IC50 (functional) = -4.2 Predicted pIC50 against Tryomastigotes Brucei rhodesiense. ChEMBL. 12086478
IC50 (binding) = 1.94 uM Inhibition of Trypanosoma cruzi farnesyl pyrophosphate synthase ChEMBL. 12951099
IC50 (binding) = 1.94 uM Inhibition of Trypanosoma cruzi farnesyl pyrophosphate synthase ChEMBL. 12951099
IC50 (binding) = 3.12 uM Inhibitory concentration of the compound against Trypanosoma brucei farnesyl pyrophosphate synthase activity ChEMBL. 12951099
IC50 (binding) = 3.12 uM Inhibitory concentration of the compound against Trypanosoma brucei farnesyl pyrophosphate synthase activity ChEMBL. 12951099
IC50 (functional) = 5.1 uM Inhibition of P. falciparum (intraerythrocytic stages) strain 3D7 ChEMBL. 11300872
IC50 (functional) = 5.1 uM Inhibition of P. falciparum (intraerythrocytic stages) strain 3D7 ChEMBL. 11300872
IC50 (functional) = 5.53 uM In vitro growth inhibition against Plasmodium falciparum ChEMBL. 14695831
IC50 (functional) = 5.53 uM In vitro growth inhibition against Plasmodium falciparum ChEMBL. 14695831
IC50 (functional) = 6 uM Antimicrobial activity against Plasmodium falciparum ChEMBL. 20185316
IC50 (binding) = 9.6 uM Inhibitory activity against Leishmania major Farnesyl diphosphate synthase ChEMBL. 14695831
IC50 (binding) = 9.6 uM Inhibitory activity against Leishmania major Farnesyl diphosphate synthase ChEMBL. 14695831
IC50 (binding) = 10.3 uM Inhibition of recombinant trypanosoma brucei soluble vacuolar pyrophosphatase expressed in escherichia coli ChEMBL. 16162013
IC50 (binding) = 10.3 uM Inhibition of recombinant trypanosoma brucei soluble vacuolar pyrophosphatase expressed in escherichia coli ChEMBL. 16162013
IC50 (binding) = 53 uM Inhibitory activity against the human recombinant geranylgeranyl diphosphate synthase (GGPPSase). ChEMBL. 12014956
IC50 (binding) = 53 uM Inhibitory activity against the human recombinant geranylgeranyl diphosphate synthase (GGPPSase). ChEMBL. 12014956
IC50 (functional) = 62.4 uM In vitro growth inhibition of blood-stream-form Trypanosoma brucei rhodesiense Trypomastigotes ChEMBL. 12086478
IC50 (functional) = 62.4 uM Inhibition of T. rhodesiense (strain STIB900) was determined using blood stream from trypomastigotes ChEMBL. 11300872
IC50 (functional) = 62.4 uM Inhibition of T. rhodesiense (strain STIB900) was determined using blood stream from trypomastigotes ChEMBL. 11300872
IC50 (functional) = 62.4 uM In vitro growth inhibition of blood-stream-form Trypanosoma brucei rhodesiense Trypomastigotes ChEMBL. 12086478
IC50 (functional) > 70 uM Inhibitory concentration against Trypanosoma cruzi (epimastigotes) ChEMBL. 12951099
IC50 (functional) > 70 uM Inhibitory concentration against Trypanosoma cruzi (amastigotes) ChEMBL. 12951099
IC50 (functional) > 70 uM In vitro antiparasitic activity against T. cruzi (epimastigotes) ChEMBL. 11277521
IC50 (functional) = 70 uM In vitro antiparasitic activity against T. cruzi (amastigotes) ChEMBL. 11277521
IC50 (functional) > 70 uM Inhibitory concentration against Trypanosoma cruzi (epimastigotes) ChEMBL. 12951099
IC50 (functional) > 70 uM Inhibitory concentration against Trypanosoma cruzi (amastigotes) ChEMBL. 12951099
IC50 (functional) > 70 uM In vitro antiparasitic activity against T. cruzi (epimastigotes) ChEMBL. 11277521
IC50 (functional) = 70 uM In vitro antiparasitic activity against T. cruzi (amastigotes) ChEMBL. 11277521
IC50 (functional) = 90 uM Inhibitory activity, for stimulation of TNF-alpha release in gamma-delta T cells, using individual observed maximum TNF-alpha release ChEMBL. 14711309
IC50 (functional) = 157 uM In vitro growth inhibition against Entamoeba histolytica ChEMBL. 14695831
IC50 (functional) = 157 uM In vitro growth inhibition against Entamoeba histolytica ChEMBL. 14695831
IC50 (functional) = 157 uM Antimicrobial activity against Entamoeba histolytica ChEMBL. 20185316
IC50 (functional) > 200 uM Inhibition of T. cruzi Amastigotes was determined in Vero cells culture and fetal calf serum ChEMBL. 11300872
IC50 (functional) > 200 uM Inhibition of L. donovani(Amastigotes) strain MHOM/ET/67/L82 maintained in female golden hamsters ChEMBL. 11300872
IC50 (functional) > 200 uM Inhibition of T. cruzi Amastigotes was determined in Vero cells culture and fetal calf serum ChEMBL. 11300872
IC50 (functional) > 200 uM Inhibition of L. donovani(Amastigotes) strain MHOM/ET/67/L82 maintained in female golden hamsters ChEMBL. 11300872
IC50 (functional) = 1200 uM Inhibitory activity against Entamoeba histolytica pyrophosphate-dependent phosphofructokinase (PFK) (Range is 600-1200) ChEMBL. 14695831
IC50 (functional) = 1612 uM Inhibitory activity, for stimulation of TNF-alpha release in gamma-delta T cells, using a constrained maximum TNF-alpha release of 2700 pg/mL ChEMBL. 14711309
Inhibition (functional) = 34 % Maximum inhibitory activity of the compound against Trypanosoma cruzi (epimastigotes) ChEMBL. 12951099
Inhibition (functional) = 34 % In vitro inhibition of antiparasitic activity against Trypanosoma cruzi at 70 microM (amastigotes) ChEMBL. 11277521
Inhibition (functional) = 34 % Maximum inhibitory activity of the compound against Trypanosoma cruzi (epimastigotes) ChEMBL. 12951099
Inhibition (functional) = 34 % In vitro inhibition of antiparasitic activity against Trypanosoma cruzi at 70 microM (amastigotes) ChEMBL. 11277521
Ki (binding) = 0.4 uM Binding affinity of the compound towards T. cruzi farnesyl pyrophosphate synthase (TcFPPS) ChEMBL. 12951099
Ki (binding) = 0.4 uM Binding affinity of the compound towards T. cruzi farnesyl pyrophosphate synthase (TcFPPS) ChEMBL. 12951099
LD50 (ADMET) > 993 uM 50% lethal dose for inhibition of KB cells growth ChEMBL. 12086478
LD50 (ADMET) > 993 uM Toxicity evaluated against human nasopharyngeal carcinoma KB cell line ChEMBL. 14695831
LD50 (ADMET) > 993 uM 50% lethal dose for inhibition of KB cells growth ChEMBL. 12086478
LD50 (ADMET) > 993 uM Toxicity evaluated against human nasopharyngeal carcinoma KB cell line ChEMBL. 14695831
Log IC50 (functional) = 2.79 pIC50 value for stimulation of TNF-alpha release in gamma-delta T cells, using a constrained maximum TNF-alpha release of 2700 pg/mL ChEMBL. 14711309
Log IC50 (functional) = 4.04 pIC50 value for stimulation of TNF-alpha release in gamma-delta T cells, using individual observed maximum TNF-alpha release ChEMBL. 14711309
Log IC50 (functional) = 4.2 Predicted pIC50 against Tryomastigotes Brucei rhodesiense. ChEMBL. 12086478
Reduction (functional) = 80 % Mean reduction in parasitaemia of Plasmodium berghei ANKA suppressive test in mice (in vivo) at 25 mg/kg scheduled for 4 days ChEMBL. 14695831
Reduction (functional) = 80 % Mean reduction in parasitaemia of Plasmodium berghei ANKA suppressive test in mice (in vivo) at 25 mg/kg scheduled for 4 days ChEMBL. 14695831
TI (functional) = 10 Ratio of ED50 against KB cell line to that of IC50 of TbVSP1 ChEMBL. 16162013
TI (ADMET) > 6.33 Therapeutic index was expressed as ratio of LD50 for KB cell line to IC50 against Entamoeba histolytica ChEMBL. 14695831
TI (functional) = 10 Ratio of ED50 against KB cell line to that of IC50 of TbVSP1 ChEMBL. 16162013
TI (ADMET) > 16 Therapeutic index measured as the ratio of LD50 (KB cells) to IC50 (T.b. rhodesiense) ChEMBL. 12086478
TI (ADMET) > 180 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 11300872

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

8 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.