Detailed information for compound 78172

Basic information

Technical information
  • TDR Targets ID: 78172
  • Name: (1-hydroxy-1-phosphonobutyl)phosphonic acid
  • MW: 234.081 | Formula: C4H12O7P2
  • H donors: 5 H acceptors: 7 LogP: -2.78 Rotable bonds: 4
    Rule of 5 violations (Lipinski): 1
  • SMILES: CCCC(P(=O)(O)O)(P(=O)(O)O)O
  • InChi: 1S/C4H12O7P2/c1-2-3-4(5,12(6,7)8)13(9,10)11/h5H,2-3H2,1H3,(H2,6,7,8)(H2,9,10,11)
  • InChiKey: RUPZRJCPTQGQRU-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (1-hydroxy-1-phosphono-butyl)phosphonic acid
  • 16856-53-4

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
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
Plasmodium berghei geranylgeranyl pyrophosphate synthase, putative 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
Echinococcus multilocularis 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
Neospora caninum hypothetical protein 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
Cryptosporidium parvum putative 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
Leishmania major 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
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
Loa Loa (eye worm) polyprenyl synthetase 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
Plasmodium falciparum geranylgeranyl pyrophosphate synthase, putative 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
Leishmania infantum 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
Mycobacterium tuberculosis Probable geranylgeranyl pyrophosphate synthetase IdsA2 (ggppsase) (GGPP synthetase) (geranylgeranyl diphosphate synthase) Get druggable targets OG5_127590 All targets in OG5_127590
Cryptosporidium hominis 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
Giardia lamblia Farnesyl diphosphate 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
Trypanosoma cruzi farnesyl pyrophosphate synthase, putative 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
Plasmodium knowlesi 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
Brugia malayi Polyprenyl synthetase family protein 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
Trypanosoma brucei 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 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
Candida albicans similar to S. cerevisiae ERG20 (YJL167W) farnesyl diphosphate synthetase (FPP synthetase) 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
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
Plasmodium falciparum geranylgeranyl pyrophosphate synthase, putative 0.0124 0.4335 1
Treponema pallidum octaprenyl-diphosphate synthase 0.0031 0.0635 0.5
Loa Loa (eye worm) glutaminase 0.0266 1 1
Plasmodium vivax octaprenyl pyrophosphate synthase, putative 0.0031 0.0635 0.1465
Echinococcus granulosus farnesyl pyrophosphate synthase 0.0124 0.4335 1
Entamoeba histolytica bifunctional short chain isoprenyl diphosphate synthase, putative 0.0031 0.0635 0.5
Mycobacterium ulcerans geranylgeranyl pyrophosphate synthase 0.0124 0.4335 0.3951
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0044 0.1163 0.2682
Echinococcus multilocularis decaprenyl diphosphate synthase subunit 1 0.0031 0.0635 0.1465
Mycobacterium leprae PROBABLE POLYPRENYL-DIPHOSPHATE SYNTHASE GRCC1 (POLYPRENYL PYROPHOSPHATE SYNTHETASE) 0.0031 0.0635 0.5
Loa Loa (eye worm) geranylgeranyl pyrophosphate synthetase 0.0031 0.0635 0.0635
Mycobacterium tuberculosis Probable polyprenyl-diphosphate synthase GrcC2 (polyprenyl pyrophosphate synthetase) 0.0031 0.0635 0.1465
Toxoplasma gondii polyprenyl synthetase superfamily protein 0.0124 0.4335 1
Trypanosoma brucei solanesyl-diphosphate synthase, putative 0.0031 0.0635 0.1465
Echinococcus multilocularis geranylgeranyl pyrophosphate synthase 0.0031 0.0635 0.1465
Brugia malayi MH2 domain containing protein 0.0116 0.4022 0.4022
Echinococcus granulosus guanine nucleotide binding protein Gs subunit 0.0044 0.1163 0.2682
Schistosoma mansoni trans-prenyltransferase 0.0031 0.0635 0.0635
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0044 0.1163 0.2682
Loa Loa (eye worm) GTP-binding regulatory protein Gs alpha-S chain 0.0044 0.1163 0.1163
Loa Loa (eye worm) glutaminase 2 0.0266 1 1
Mycobacterium ulcerans geranylgeranyl pyrophosphate synthase 0.0124 0.4335 0.3951
Chlamydia trachomatis geranylgeranyl pyrophosphate synthase 0.0031 0.0635 0.5
Trypanosoma cruzi solanesyl-diphosphate synthase, putative 0.0031 0.0635 0.1465
Echinococcus granulosus geranylgeranyl pyrophosphate synthase 0.0031 0.0635 0.1465
Plasmodium falciparum octaprenyl pyrophosphate synthase 0.0031 0.0635 0.1465
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0044 0.1163 0.1163
Trypanosoma brucei farnesyl pyrophosphate synthase 0.0124 0.4335 1
Giardia lamblia Farnesyl diphosphate synthase 0.0124 0.4335 0.5
Mycobacterium tuberculosis Possible polyprenyl synthetase IdsB (polyprenyl transferase) (polyprenyl diphosphate synthase) 0.0031 0.0635 0.1465
Echinococcus multilocularis guanine nucleotide binding protein G(s) subunit 0.0044 0.1163 0.2682
Schistosoma mansoni geranylgeranyl pyrophosphate synthase 0.0031 0.0635 0.0635
Schistosoma mansoni farnesyl pyrophosphate synthase 0.0124 0.4335 0.4335
Loa Loa (eye worm) polyprenyl synthetase 0.0031 0.0635 0.0635
Echinococcus granulosus decaprenyl diphosphate synthase subunit 1 0.0031 0.0635 0.1465
Trypanosoma cruzi polyprenyl synthase, putative 0.0031 0.0635 0.1465
Echinococcus multilocularis prenyl (decaprenyl) diphosphate synthase 0.0031 0.0635 0.1465
Trypanosoma cruzi farnesyl pyrophosphate synthase 0.0124 0.4335 1
Mycobacterium tuberculosis Probable geranylgeranyl pyrophosphate synthetase IdsA2 (ggppsase) (GGPP synthetase) (geranylgeranyl diphosphate synthase) 0.0124 0.4335 1
Loa Loa (eye worm) polyprenyl synthetase 0.0124 0.4335 0.4335
Trypanosoma cruzi farnesyl pyrophosphate synthase, putative 0.0124 0.4335 1
Echinococcus multilocularis farnesyl pyrophosphate synthase 0.0124 0.4335 1
Leishmania major solanesyl-diphosphate synthase, putative 0.0031 0.0635 0.1465
Schistosoma mansoni glutathione synthetase 0.0031 0.0635 0.0635
Leishmania major farnesyl pyrophosphate synthase 0.0124 0.4335 1
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0044 0.1163 0.1163
Entamoeba histolytica geranylgeranyl pyrophosphate synthase, putative 0.0031 0.0635 0.5
Plasmodium vivax geranylgeranyl pyrophosphate synthase 0.0124 0.4335 1
Schistosoma mansoni Guanine nucleotide-binding protein G(s) subunit alpha (Adenylate cyclase-stimulating G alpha protein) 0.0044 0.1163 0.1163
Mycobacterium tuberculosis Probable multifunctional geranylgeranyl pyrophosphate synthetase IdsA1 (GGPP synthetase) (ggppsase) (geranylgeranyl diphosphate 0.0031 0.0635 0.1465
Loa Loa (eye worm) transcription factor SMAD2 0.0116 0.4022 0.4022
Brugia malayi GTP-binding regulatory protein Gs alpha-S chain, putative 0.0044 0.1163 0.1163
Trypanosoma cruzi solanesyl-diphosphate synthase, putative 0.0031 0.0635 0.1465
Mycobacterium ulcerans glutaminase 0.0266 1 1
Loa Loa (eye worm) MH2 domain-containing protein 0.0116 0.4022 0.4022
Brugia malayi Polyprenyl synthetase family protein 0.0031 0.0635 0.0635
Trichomonas vaginalis glutaminase, putative 0.0266 1 1
Brugia malayi geranylgeranyl pyrophosphate synthetase 0.0031 0.0635 0.0635
Wolbachia endosymbiont of Brugia malayi geranylgeranyl pyrophosphate synthase 0.0031 0.0635 0.5
Trypanosoma cruzi solanesyl-diphosphate synthase 0.0031 0.0635 0.1465
Wolbachia endosymbiont of Brugia malayi geranylgeranyl pyrophosphate synthase 0.0031 0.0635 0.5
Trypanosoma cruzi polyprenyl synthase, putative 0.0031 0.0635 0.1465
Entamoeba histolytica geranylgeranyl pyrophosphate synthetase, putative 0.0031 0.0635 0.5
Toxoplasma gondii polyprenyl synthetase superfamily protein 0.0031 0.0635 0.1465
Brugia malayi Polyprenyl synthetase family protein 0.0124 0.4335 0.4335
Schistosoma mansoni glutaminase 0.0266 1 1
Leishmania major polyprenyl synthase, putative 0.0031 0.0635 0.1465
Echinococcus granulosus prenyl decaprenyl diphosphate synthase 0.0031 0.0635 0.1465

Activities

Activity type Activity value Assay description Source Reference
IC50 (functional) = -4.04 Predicted pIC50 against Tryomastigotes Brucei rhodesiense. ChEMBL. 12086478
IC50 (functional) = 3.9 Growth inhibition of Plasmodium falciparum ChEMBL. 19053772
IC50 (functional) = 9.1 uM Inhibition of T. gondii tachyzoites in human foreskin fibroblast monolayer(DMEM with 10%fetal calf serum) ChEMBL. 11300872
IC50 (functional) = 9.1 uM Inhibition of T. gondii tachyzoites in human foreskin fibroblast monolayer(DMEM with 10%fetal calf serum) ChEMBL. 11300872
IC50 (functional) = 21.4 uM Inhibitory concentration against Trypanosoma cruzi (amastigotes) ChEMBL. 12951099
IC50 (functional) = 21.4 uM In vitro antiparasitic activity against T. cruzi (amastigotes) ChEMBL. 11277521
IC50 (functional) = 21.4 uM Inhibitory concentration against Trypanosoma cruzi (amastigotes) ChEMBL. 12951099
IC50 (functional) = 21.4 uM In vitro antiparasitic activity against T. cruzi (amastigotes) ChEMBL. 11277521
IC50 (binding) = 21.5 uM Inhibition of recombinant trypanosoma brucei soluble vacuolar pyrophosphatase expressed in escherichia coli ChEMBL. 16162013
IC50 (binding) = 21.5 uM Inhibition of recombinant trypanosoma brucei soluble vacuolar pyrophosphatase expressed in escherichia coli ChEMBL. 16162013
IC50 (binding) = 42.83 uM Inhibition of Trypanosoma cruzi farnesyl pyrophosphate synthase ChEMBL. 12951099
IC50 (binding) = 42.83 uM Inhibition of Trypanosoma cruzi farnesyl pyrophosphate synthase ChEMBL. 12951099
IC50 (functional) > 70 uM Inhibitory concentration against Trypanosoma cruzi (epimastigotes) ChEMBL. 12951099
IC50 (functional) > 70 uM In vitro antiparasitic activity against T. cruzi (epimastigotes) ChEMBL. 11277521
IC50 (functional) > 70 uM Inhibitory concentration against Trypanosoma cruzi (epimastigotes) ChEMBL. 12951099
IC50 (functional) > 70 uM In vitro antiparasitic activity against T. cruzi (epimastigotes) ChEMBL. 11277521
IC50 (functional) = 92 uM In vitro growth inhibition of blood-stream-form Trypanosoma brucei rhodesiense Trypomastigotes ChEMBL. 12086478
IC50 (functional) = 92 uM Inhibition of T. rhodesiense (strain STIB900) was determined using blood stream from trypomastigotes ChEMBL. 11300872
IC50 (functional) = 92 uM Inhibition of T. rhodesiense (strain STIB900) was determined using blood stream from trypomastigotes ChEMBL. 11300872
IC50 (functional) = 92 uM In vitro growth inhibition of blood-stream-form Trypanosoma brucei rhodesiense Trypomastigotes ChEMBL. 12086478
IC50 (binding) > 100 uM Inhibitory concentration of the compound against Trypanosoma brucei farnesyl pyrophosphate synthase activity ChEMBL. 12951099
IC50 (binding) > 100 uM Inhibitory activity against Leishmania major Farnesyl diphosphate synthase ChEMBL. 14695831
IC50 (binding) > 100 uM Inhibitory concentration of the compound against Trypanosoma brucei farnesyl pyrophosphate synthase activity ChEMBL. 12951099
IC50 (binding) > 100 uM Inhibitory activity against Leishmania major Farnesyl diphosphate synthase ChEMBL. 14695831
IC50 (functional) = 130 uM Inhibition of P. falciparum (intraerythrocytic stages) strain 3D7 ChEMBL. 11300872
IC50 (functional) = 130 uM In vitro growth inhibition against Plasmodium falciparum ChEMBL. 14695831
IC50 (functional) = 130 uM Inhibition of P. falciparum (intraerythrocytic stages) strain 3D7 ChEMBL. 11300872
IC50 (functional) = 130 uM In vitro growth inhibition against Plasmodium falciparum ChEMBL. 14695831
IC50 (functional) = 130 uM Growth inhibition of Plasmodium falciparum ChEMBL. 19053772
IC50 (functional) = 130 uM Antimicrobial activity against Plasmodium falciparum 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 In vitro growth inhibition against Entamoeba histolytica ChEMBL. 14695831
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 In vitro growth inhibition against Entamoeba histolytica ChEMBL. 14695831
IC50 (functional) = 200 uM Antimicrobial activity against Entamoeba histolytica ChEMBL. 20185316
IC50 (binding) = 620 uM Inhibitory activity against the human recombinant geranylgeranyl diphosphate synthase (GGPPSase). ChEMBL. 12014956
IC50 (binding) = 620 uM Inhibitory activity against the human recombinant geranylgeranyl diphosphate synthase (GGPPSase). ChEMBL. 12014956
IZ (functional) = 0 mm Antibacterial activity against Escherichia coli W3110 ChEMBL. 17149863
IZ (functional) = 0 mm Antibacterial activity against Escherichia coli W3110 ChEMBL. 17149863
Ki (binding) = 5.04 uM Binding affinity of the compound towards T. cruzi farnesyl pyrophosphate synthase (TcFPPS) ChEMBL. 12951099
Ki (binding) = 5.04 uM Binding affinity of the compound towards T. cruzi farnesyl pyrophosphate synthase (TcFPPS) ChEMBL. 12951099
LD50 (ADMET) > 967 uM 50% lethal dose for inhibition of KB cells growth ChEMBL. 12086478
LD50 (ADMET) > 967 uM Toxicity evaluated against human nasopharyngeal carcinoma KB cell line ChEMBL. 14695831
LD50 (ADMET) > 967 uM 50% lethal dose for inhibition of KB cells growth ChEMBL. 12086478
LD50 (ADMET) > 967 uM Toxicity evaluated against human nasopharyngeal carcinoma KB cell line ChEMBL. 14695831
Log IC50 (functional) = 4.04 Predicted pIC50 against Tryomastigotes Brucei rhodesiense. ChEMBL. 12086478
TI (ADMET) > 7.44 Therapeutic index was expressed as ratio of LD50 for KB cell line to IC50 against Plasmodium falciparum ChEMBL. 14695831
TI (ADMET) > 11 Therapeutic index measured as the ratio of LD50 (KB cells) to IC50 (T.b. rhodesiense) ChEMBL. 12086478

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Toxoplasma gondii 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.

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