Detailed information for compound 83410
Basic information
Technical information
- TDR Targets ID: 83410
- Name: (1-hydroxy-1-phosphono-3-pyridin-3-ylpropyl)p hosphonic acid
- MW: 297.139 | Formula: C8H13NO7P2
-
H donors: 5
H acceptors: 8
LogP: -2.79
Rotable bonds: 5
Rule of 5 violations (Lipinski): 1 - SMILES: OP(=O)(C(P(=O)(O)O)(CCc1cccnc1)O)O
- InChi: 1S/C8H13NO7P2/c10-8(17(11,12)13,18(14,15)16)4-3-7-2-1-5-9-6-7/h1-2,5-6,10H,3-4H2,(H2,11,12,13)(H2,14,15,16)
- InChiKey: ILROXFQHACCDLA-UHFFFAOYSA-N
Network
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Synonyms
- [1-hydroxy-1-phosphono-3-(3-pyridyl)propyl]phosphonic acid
- (1-hydroxy-1-phosphono-3-pyridin-3-yl-propyl)phosphonic acid
- NE 58051
- 104261-69-0
- 3-(3-Pyridyl)-1-hydroxypropylidene bisphosphonic acid
- NE-58051
- Phosphonic acid, (1-hydroxy-3-(3-pyridinyl)propylidene)bis-
- (1-Hydroxy-3-(3-pyridinyl)propylidene)bisphosphonic acid
Targets
Known targets for this compound
| Species | Target name | Source | Bibliographic reference |
|---|---|---|---|
| Trypanosoma cruzi | farnesyl pyrophosphate synthase | Curated by TDR Targets | No references |
| Homo sapiens | farnesyl diphosphate synthase | Starlite/ChEMBL | References |
| Trypanosoma cruzi | farnesyl pyrophosphate synthase, putative | Curated by TDR Targets | No references |
Predicted pathogen targets for this compound
By orthology
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 |
|---|---|---|---|---|
| Trichomonas vaginalis | geranylgeranyl pyrophosphate synthase, putative | 0.0123843 | 0.5 | 0.5 |
| Echinococcus granulosus | farnesyl pyrophosphate synthase | 0.0123843 | 0.5 | 0.5 |
| Loa Loa (eye worm) | polyprenyl synthetase | 0.0123843 | 0.5 | 0.5 |
| Trypanosoma cruzi | farnesyl pyrophosphate synthase | 0.0123843 | 0.5 | 0.5 |
| Plasmodium vivax | geranylgeranyl pyrophosphate synthase | 0.0123843 | 0.5 | 0.5 |
| Trichomonas vaginalis | geranylgeranyl pyrophosphate synthase, putative | 0.0123843 | 0.5 | 0.5 |
| Brugia malayi | Polyprenyl synthetase family protein | 0.0123843 | 0.5 | 0.5 |
| Mycobacterium ulcerans | geranylgeranyl pyrophosphate synthase | 0.0123843 | 0.5 | 0.5 |
| Trypanosoma cruzi | farnesyl pyrophosphate synthase, putative | 0.0123843 | 0.5 | 0.5 |
| Leishmania major | farnesyl pyrophosphate synthase | 0.0123843 | 0.5 | 0.5 |
| Echinococcus multilocularis | farnesyl pyrophosphate synthase | 0.0123843 | 0.5 | 0.5 |
| Toxoplasma gondii | polyprenyl synthetase superfamily protein | 0.0123843 | 0.5 | 0.5 |
| Schistosoma mansoni | farnesyl pyrophosphate synthase | 0.0123843 | 0.5 | 0.5 |
| Mycobacterium ulcerans | geranylgeranyl pyrophosphate synthase | 0.0123843 | 0.5 | 0.5 |
| Plasmodium falciparum | geranylgeranyl pyrophosphate synthase, putative | 0.0123843 | 0.5 | 0.5 |
| Trichomonas vaginalis | geranylgeranyl diphosphate synthase, putative | 0.0123843 | 0.5 | 0.5 |
| Trypanosoma brucei | farnesyl pyrophosphate synthase | 0.0123843 | 0.5 | 0.5 |
| Giardia lamblia | Farnesyl diphosphate synthase | 0.0123843 | 0.5 | 0.5 |
| Mycobacterium tuberculosis | Probable geranylgeranyl pyrophosphate synthetase IdsA2 (ggppsase) (GGPP synthetase) (geranylgeranyl diphosphate synthase) | 0.0123843 | 0.5 | 0.5 |
Activities
| Activity type | Activity value | Assay description | Source | Reference |
|---|---|---|---|---|
| IC50 (functional) | = -5.77 | Predicted pIC50 against Tryomastigotes Brucei rhodesiense. | ChEMBL. | 12086478 |
| IC50 (binding) | = -5.27 | Inhibitory activity against farnesyl Pyrophosphate Synthase expressed as #NAME? (M) | ChEMBL. | 14613320 |
| IC50 (binding) | = 78 nM | Inhibition of human FPPS using pre-incubation of compound with enzyme | ChEMBL. | 25815158 |
| IC50 (binding) | = 337.3 nM | Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 after 10 mins | ChEMBL. | 18327899 |
| IC50 (binding) | = 337.3 nM | Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 after 10 mins | ChEMBL. | 18327899 |
| IC50 (binding) | = 363 nM | Inhibition of human FPPS in absence of pre-incubation of compound with enzyme | ChEMBL. | 25815158 |
| IC50 (binding) | = 2113 nM | Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 | ChEMBL. | 18327899 |
| IC50 (binding) | = 2113 nM | Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 | ChEMBL. | 18327899 |
| IC50 (functional) | = 1.7 uM | In vitro growth inhibition of blood-stream-form Trypanosoma brucei rhodesiense Trypomastigotes | ChEMBL. | 12086478 |
| IC50 (functional) | = 1.7 uM | Inhibition of T. rhodesiense (strain STIB900) was determined using blood stream from trypomastigotes | ChEMBL. | 11300872 |
| IC50 (functional) | = 1.7 uM | Inhibition of T. rhodesiense (strain STIB900) was determined using blood stream from trypomastigotes | ChEMBL. | 11300872 |
| IC50 (functional) | = 1.7 uM | In vitro growth inhibition of blood-stream-form Trypanosoma brucei rhodesiense Trypomastigotes | ChEMBL. | 12086478 |
| IC50 (binding) | = 2.93 uM | Inhibitory activity against the human recombinant FPPSase(Farnesyl diphosphate) enzyme | ChEMBL. | 12014956 |
| IC50 (binding) | = 2.93 uM | Inhibitory activity against the human recombinant FPPSase(Farnesyl diphosphate) enzyme | ChEMBL. | 12014956 |
| IC50 (binding) | = 5.4 uM | Inhibitory activity against farnesyl Pyrophosphate Synthase was determined | ChEMBL. | 14613320 |
| IC50 (binding) | = 5.4 uM | Inhibitory activity against farnesyl Pyrophosphate Synthase was determined | ChEMBL. | 14613320 |
| IC50 (functional) | = 147.3 uM | In vitro inhibitory concentration against the growth of Toxoplasma gondii in human foreskin fibroblast monolayer cells (HFF cells) | ChEMBL. | 15857119 |
| IC50 (functional) | > 200 uM | In vitro growth inhibition against Entamoeba histolytica | ChEMBL. | 14695831 |
| IC50 (functional) | > 200 uM | In vitro growth inhibition against Plasmodium falciparum | 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 T. gondii tachyzoites in human foreskin fibroblast monolayer(DMEM with 10%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 P. falciparum (intraerythrocytic stages) strain 3D7 | ChEMBL. | 11300872 |
| IC50 (functional) | > 200 uM | In vitro growth inhibition against Entamoeba histolytica | ChEMBL. | 14695831 |
| IC50 (functional) | > 200 uM | In vitro growth inhibition against Plasmodium falciparum | 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 T. gondii tachyzoites in human foreskin fibroblast monolayer(DMEM with 10%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 P. falciparum (intraerythrocytic stages) strain 3D7 | ChEMBL. | 11300872 |
| IC50 (functional) | = 200 uM | Antimicrobial activity against Plasmodium falciparum | ChEMBL. | 20185316 |
| IC50 (functional) | = 200 uM | Antimicrobial activity against Entamoeba histolytica | ChEMBL. | 20185316 |
| IC50 (functional) | = 228 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) | = 310 uM | Ability to inhibit growth of D. discoideum. | ChEMBL. | 12086477 |
| IC50 (functional) | = 310 uM | Ability to inhibit growth of D. discoideum. | ChEMBL. | 12086477 |
| IC50 (functional) | = 310 uM | Antimicrobial activity against Dictyostelium discoideum | ChEMBL. | 18590315 |
| IC50 (binding) | = 410 uM | Inhibitory activity against the human recombinant geranylgeranyl diphosphate synthase (GGPPSase). | ChEMBL. | 12014956 |
| IC50 (binding) | = 410 uM | Inhibitory activity against the human recombinant geranylgeranyl diphosphate synthase (GGPPSase). | ChEMBL. | 12014956 |
| IC50 (functional) | = 917 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 |
| Infected (functional) | = 6 % | Percent infected vero cells was determined | ChEMBL. | 11300872 |
| Inhibition (binding) | = 23 % | Inhibition of farnesyl diphosphate synthase at 100 nM | ChEMBL. | 18590315 |
| Inhibition (functional) | = 81 % | Effect on proliferation of T. cruzi Amastigotes in vero cells at a conc of 150 microM was determined | ChEMBL. | 11300872 |
| Inhibition (functional) | = 81 % | Effect on proliferation of T. cruzi Amastigotes in vero cells at a conc of 150 microM was determined | ChEMBL. | 11300872 |
| 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) | = 78 nM | Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 after 10 mins | ChEMBL. | 18327899 |
| Ki (binding) | = 78 nM | Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 after 10 mins | ChEMBL. | 18327899 |
| Ki (binding) | = 362.6 nM | Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 | ChEMBL. | 18327899 |
| Ki (binding) | = 362.6 nM | Inhibition of human recombinant FPPS expressed in Escherichia coli BL21 | ChEMBL. | 18327899 |
| Ki (binding) | = 0.51 uM | Binding affinity towards farnesyl Pyrophosphate Synthase using [14C]- isopentenyl pyrophosphate as radioligand | ChEMBL. | 14613320 |
| Ki (binding) | = 0.51 uM | Binding affinity towards farnesyl Pyrophosphate Synthase using [14C]- isopentenyl pyrophosphate as radioligand | ChEMBL. | 14613320 |
| LD50 (ADMET) | > 804 uM | 50% lethal dose for inhibition of KB cells growth | ChEMBL. | 12086478 |
| LD50 (ADMET) | > 804 uM | Toxicity evaluated against human nasopharyngeal carcinoma KB cell line | ChEMBL. | 14695831 |
| LD50 (ADMET) | > 804 uM | 50% lethal dose for inhibition of KB cells growth | ChEMBL. | 12086478 |
| LD50 (ADMET) | > 804 uM | Toxicity evaluated against human nasopharyngeal carcinoma KB cell line | ChEMBL. | 14695831 |
| LD50 (functional) | > 804 uM | Lethal dose required to inhibit the growth of human KB (nasopharyngeal carcinoma) cell line | ChEMBL. | 15857119 |
| LED (functional) | = 1 mg kg-1 | Inhibition of bone resorption in rat assessed as phosphate | ChEMBL. | 18327899 |
| LED (functional) | = 1 mgP kg-1 | Bone resorption activity in rats. | ChEMBL. | 12086477 |
| Log IC50 (functional) | = 3.04 | 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) | = 3.64 | pIC50 value for stimulation of TNF-alpha release in gamma-delta T cells, using individual observed maximum TNF-alpha release | ChEMBL. | 14711309 |
| Log IC50 (binding) | = 5.27 | Inhibitory activity against farnesyl Pyrophosphate Synthase expressed as #NAME? (M) | ChEMBL. | 14613320 |
| Log IC50 (functional) | = 5.77 | Predicted pIC50 against Tryomastigotes Brucei rhodesiense. | ChEMBL. | 12086478 |
| TI (ADMET) | > 473 | 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 |
|---|---|---|---|
| Trypanosoma brucei | ChEMBL23 | 11300872 | |
| Trypanosoma brucei gambiense | 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:
| Affected Entity | Phenotypic quality | Occurs in | Occurs at | Evidence | Observed in | Targets |
|---|---|---|---|---|---|---|
| catalytic activity (GO:0003824) | decreased (PATO:0000468) | inferred from enzyme inhibition (ECO:0000184) | Trypanosoma cruzi | 46630 | ||
| Annotator: | millerja@u.washington.edu | Comment: | References: | 11435429 16143525 | ||
| catalytic activity (GO:0003824) | decreased (PATO:0000468) | inferred from enzyme inhibition (ECO:0000184) | Trypanosoma cruzi | 51685 | ||
| Annotator: | millerja@u.washington.edu | Comment: | References: | 11435429 16143525 | ||
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.
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
- Search by CAS
- ChEMBL: CHEMBL293522
- PubChem: 128523
Bibliographic References
11 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.