Detailed information for compound 80149

Basic information

Technical information
  • TDR Targets ID: 80149
  • Name: [[(5-chloropyridin-2-yl)amino]-phosphonomethy l]phosphonic acid
  • MW: 302.546 | Formula: C6H9ClN2O6P2
  • H donors: 5 H acceptors: 7 LogP: -1.59 Rotable bonds: 4
    Rule of 5 violations (Lipinski): 1
  • SMILES: Clc1ccc(nc1)NC(P(=O)(O)O)P(=O)(O)O
  • InChi: 1S/C6H9ClN2O6P2/c7-4-1-2-5(8-3-4)9-6(16(10,11)12)17(13,14)15/h1-3,6H,(H,8,9)(H2,10,11,12)(H2,13,14,15)
  • InChiKey: BNMYZGAZFGNKTH-UHFFFAOYSA-N  


Substructure search Similarity search

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Synonyms

  • [{(5-Chloro-2-Pyridinyl)Amino} Methylene]-1,1-Bisphosphonate
  • [[(5-chloro-2-pyridyl)amino]-phosphono-methyl]phosphonic acid
  • [[(5-chloro-2-pyridyl)amino]-phosphonomethyl]phosphonic acid
  • [[(5-chloropyridin-2-yl)amino]-phosphono-methyl]phosphonic acid
  • [[(5-chloropyridin-1-ium-2-yl)amino]-phosphonomethyl]-hydroxyphosphinate
  • [[(5-chloropyridin-1-ium-2-yl)amino]-phosphono-methyl]-hydroxy-phosphinate
  • [[(5-chloro-2-pyridin-1-iumyl)amino]-phosphonomethyl]-hydroxyphosphinate
  • 70010-82-1
  • NSC722618
  • [[(5-chloro-2-pyridinyl)amino]methylene]-1,1-bisphosphonate
  • AIDS-257675
  • AIDS257675
  • Phosphonic acid, [[(5-chloro-2-pyridinyl)amino]methylene]bis-
  • CBQ
  • [(5-CHLORO-PYRIDIN-2-YLAMINO)-PHOSPHONO-METHYL]-PHOSPHONIC ACID

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens farnesyl diphosphate synthase Starlite/ChEMBL References
Homo sapiens farnesyl-diphosphate farnesyltransferase 1 Starlite/ChEMBL References
Escherichia coli 1-deoxy-D-xylulose 5-phosphate reductoisomerase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Candida albicans squalene synthase similar to S. cerevisiae ERG9 (YHR190W) involved in ergosterol biosynthesis Get druggable targets OG5_129470 All targets in OG5_129470
Plasmodium knowlesi geranylgeranyl 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
Babesia bovis 1-deoxy-D-xylulose 5-phosphate reductoisomerase family protein Get druggable targets OG5_130462 All targets in OG5_130462
Leishmania mexicana 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
Toxoplasma gondii polyprenyl synthetase superfamily protein Get druggable targets OG5_127590 All targets in OG5_127590
Trypanosoma brucei squalene synthase, putative Get druggable targets OG5_129470 All targets in OG5_129470
Echinococcus multilocularis 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
Cryptosporidium parvum putative farnesyl pyrophosphate synthase 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
Toxoplasma gondii 1-deoxy-D-xylulose 5-phosphate reductoisomerase, putative Get druggable targets OG5_130462 All targets in OG5_130462
Trichomonas vaginalis geranylgeranyl diphosphate synthase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Leishmania braziliensis squalene synthase, putative Get druggable targets OG5_129470 All targets in OG5_129470
Trypanosoma congolense squalene synthase, putative Get druggable targets OG5_129470 All targets in OG5_129470
Loa Loa (eye worm) polyprenyl synthetase Get druggable targets OG5_127590 All targets in OG5_127590
Candida albicans squalene synthase similar to S. cerevisiae ERG9 (YHR190W) involved in ergosterol biosynthesis Get druggable targets OG5_129470 All targets in OG5_129470
Schistosoma japonicum ko:K00787 dimethylallyltranstransferase [EC2.5.1.1], putative 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
Mycobacterium leprae PROBABLE 1-DEOXY-D-XYLULOSE 5-PHOSPHATE REDUCTOISOMERASE DXR (DXP REDUCTOISOMERASE) (1-DEOXYXYLULOSE-5-PHOSPHATE REDUCTOISOMERAS Get druggable targets OG5_130462 All targets in OG5_130462
Leishmania braziliensis farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Leishmania mexicana farnesyltransferase, putative Get druggable targets OG5_129470 All targets in OG5_129470
Theileria parva farnesyl pyrophosphate synthetase, putative Get druggable targets OG5_127590 All targets in OG5_127590
Leishmania infantum squalene synthase, putative Get druggable targets OG5_129470 All targets in OG5_129470
Leishmania infantum farnesyl pyrophosphate 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
Trypanosoma congolense squalene synthase, putative Get druggable targets OG5_129470 All targets in OG5_129470
Trypanosoma brucei farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Trypanosoma cruzi squalene synthase, putative Get druggable targets OG5_129470 All targets in OG5_129470
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
Plasmodium yoelii 1-deoxy-D-xylulose 5-phosphate reductoisomerase Get druggable targets OG5_130462 All targets in OG5_130462
Chlamydia trachomatis 1-deoxy-D-xylulose 5-phosphate reductoisomerase Get druggable targets OG5_130462 All targets in OG5_130462
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
Neospora caninum 1-deoxy-D-xylulose 5-phosphate reductoisomerase, putative Get druggable targets OG5_130462 All targets in OG5_130462
Plasmodium berghei 1-deoxy-D-xylulose 5-phosphate reductoisomerase, putative Get druggable targets OG5_130462 All targets in OG5_130462
Brugia malayi Polyprenyl synthetase family protein Get druggable targets OG5_127590 All targets in OG5_127590
Leishmania major squalene synthase, putative Get druggable targets OG5_129470 All targets in OG5_129470
Trypanosoma cruzi squalene synthase, putative Get druggable targets OG5_129470 All targets in OG5_129470
Giardia lamblia Farnesyl diphosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Trypanosoma congolense squalene synthase, putative Get druggable targets OG5_129470 All targets in OG5_129470
Treponema pallidum 1-deoxy-D-xylulose 5-phosphate reductoisomerase Get druggable targets OG5_130462 All targets in OG5_130462
Plasmodium falciparum 1-deoxy-D-xylulose 5-phosphate reductoisomerase Get druggable targets OG5_130462 All targets in OG5_130462
Mycobacterium tuberculosis Probable geranylgeranyl pyrophosphate synthetase IdsA2 (ggppsase) (GGPP synthetase) (geranylgeranyl diphosphate synthase) Get druggable targets OG5_127590 All targets in OG5_127590
Mycobacterium tuberculosis Probable 1-deoxy-D-xylulose 5-phosphate reductoisomerase Dxr (DXP reductoisomerase) (1-deoxyxylulose-5-phosphate reductoisomeras Get druggable targets OG5_130462 All targets in OG5_130462
Plasmodium yoelii 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
Wolbachia endosymbiont of Brugia malayi 1-deoxy-D-xylulose 5-phosphate reductoisomerase Get druggable targets OG5_130462 All targets in OG5_130462
Trypanosoma brucei gambiense farnesyltransferase, putative,squalene synthase, putative Get druggable targets OG5_129470 All targets in OG5_129470
Schistosoma mansoni farnesyl pyrophosphate synthase Get druggable targets OG5_127590 All targets in OG5_127590
Neospora caninum hypothetical protein 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
Leishmania donovani farnesyltransferase, putative Get druggable targets OG5_129470 All targets in OG5_129470
Cryptosporidium hominis 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
Trichomonas vaginalis 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
Theileria parva 1-deoxy-D-xylulose 5-phosphate reductoisomerase, putative Get druggable targets OG5_130462 All targets in OG5_130462
Mycobacterium ulcerans 1-deoxy-D-xylulose 5-phosphate reductoisomerase Get druggable targets OG5_130462 All targets in OG5_130462
Leishmania major 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 knowlesi 1-deoxy-D-xylulose 5-phosphate reductoisomerase, putative Get druggable targets OG5_130462 All targets in OG5_130462
Plasmodium vivax 1-deoxy-D-xylulose 5-phosphate reductoisomerase, putative Get druggable targets OG5_130462 All targets in OG5_130462
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
Toxoplasma gondii 1-deoxy-D-xylulose 5-phosphate reductoisomerase, putative 0.0519737 1 1
Brugia malayi Polyprenyl synthetase family protein 0.0123843 0 0.5
Mycobacterium leprae PROBABLE 1-DEOXY-D-XYLULOSE 5-PHOSPHATE REDUCTOISOMERASE DXR (DXP REDUCTOISOMERASE) (1-DEOXYXYLULOSE-5-PHOSPHATE REDUCTOISOMERAS 0.0519737 1 0.5
Loa Loa (eye worm) polyprenyl synthetase 0.0123843 0 0.5
Leishmania major squalene synthase, putative 0.0295602 0.433852 1
Mycobacterium ulcerans 1-deoxy-D-xylulose 5-phosphate reductoisomerase 0.0519737 1 1
Echinococcus granulosus farnesyl pyrophosphate synthase 0.0123843 0 0.5
Chlamydia trachomatis 1-deoxy-D-xylulose 5-phosphate reductoisomerase 0.0519737 1 0.5
Trichomonas vaginalis geranylgeranyl pyrophosphate synthase, putative 0.0123843 0 0.5
Trypanosoma cruzi squalene synthase, putative 0.0295602 0.433852 1
Trypanosoma brucei squalene synthase, putative 0.0295602 0.433852 1
Trypanosoma cruzi squalene synthase, putative 0.0295602 0.433852 1
Schistosoma mansoni farnesyl pyrophosphate synthase 0.0123843 0 0.5
Trichomonas vaginalis geranylgeranyl diphosphate synthase, putative 0.0123843 0 0.5
Plasmodium falciparum 1-deoxy-D-xylulose 5-phosphate reductoisomerase 0.0519737 1 1
Giardia lamblia Farnesyl diphosphate synthase 0.0123843 0 0.5
Plasmodium vivax 1-deoxy-D-xylulose 5-phosphate reductoisomerase, putative 0.0519737 1 1
Trichomonas vaginalis geranylgeranyl pyrophosphate synthase, putative 0.0123843 0 0.5
Echinococcus multilocularis farnesyl pyrophosphate synthase 0.0123843 0 0.5
Mycobacterium tuberculosis Probable 1-deoxy-D-xylulose 5-phosphate reductoisomerase Dxr (DXP reductoisomerase) (1-deoxyxylulose-5-phosphate reductoisomeras 0.0125 0.00292353 1
Wolbachia endosymbiont of Brugia malayi 1-deoxy-D-xylulose 5-phosphate reductoisomerase 0.0519737 1 0.5
Treponema pallidum 1-deoxy-D-xylulose 5-phosphate reductoisomerase 0.0519737 1 0.5

Activities

Activity type Activity value Assay description Source Reference
Activity (binding) = 92.4 % Inhibition of Arabidopsis thaliana P5C reductase catalytic activity assessed as residual concentration of enzyme at 535 nm OD at 0.5 mM by P5C utilization assay ChEMBL. 17474756
Activity (binding) = 101.4 % Inhibition of Arabidopsis thaliana P5C reductase catalytic activity assessed as inhibition of NADPH oxidation at 340 nm OD at 0.2 mM by NADPH oxidation assay ChEMBL. 17474756
IC50 (binding) = -6.62 Inhibitory activity against farnesyl Pyrophosphate Synthase expressed as #NAME? (M) ChEMBL. 14613320
IC50 (functional) = -4.27 Predicted pIC50 against Tryomastigotes Brucei rhodesiense. ChEMBL. 12086478
IC50 (functional) = 5 Growth inhibition of Plasmodium falciparum ChEMBL. 19053772
IC50 (binding) = 0.069 mM Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase assessed as inhibition of glutamine synthesis from glutamic acid after 15 min by biosynthetic assay ChEMBL. 15161194
IC50 (binding) = 0.096 mM Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase after 30 min by hemibiosynthetic assay ChEMBL. 15161194
IC50 (binding) = 1.04 mM Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase by transferase assay ChEMBL. 15161194
IC50 (binding) = 0.24 uM Inhibitory activity against Leishmania major Farnesyl-diphosphatesynthase (FPP synthase) ChEMBL. 14695831
IC50 (binding) = 0.24 uM Inhibitory activity against farnesyl Pyrophosphate Synthase was determined ChEMBL. 14613320
IC50 (binding) = 0.24 uM Inhibitory activity against Leishmania major Farnesyl-diphosphatesynthase (FPP synthase) ChEMBL. 14695831
IC50 (binding) = 0.24 uM Inhibitory activity against farnesyl Pyrophosphate Synthase was determined ChEMBL. 14613320
IC50 (binding) = 7 uM Inhibition of Escherichia coli DXR ChEMBL. 21379374
IC50 (functional) = 10.6 uM In vitro growth inhibition against Plasmodium falciparum ChEMBL. 14695831
IC50 (functional) = 10.6 uM In vitro growth inhibition against Plasmodium falciparum ChEMBL. 14695831
IC50 (functional) = 11 uM Growth inhibition of Plasmodium falciparum ChEMBL. 19053772
IC50 (functional) = 11 uM Antimicrobial activity against Plasmodium falciparum ChEMBL. 20185316
IC50 (functional) = 53.3 uM In vitro growth inhibition of blood-stream-form Trypanosoma brucei rhodesiense Trypomastigotes ChEMBL. 12086478
IC50 (functional) = 53.3 uM In vitro growth inhibition of blood-stream-form Trypanosoma brucei rhodesiense Trypomastigotes ChEMBL. 12086478
IC50 (functional) = 87 uM In vitro growth inhibition against Entamoeba histolytica ChEMBL. 14695831
IC50 (functional) = 87 uM In vitro growth inhibition against Entamoeba histolytica ChEMBL. 14695831
IC50 (functional) = 87 uM Antimicrobial activity against Entamoeba histolytica ChEMBL. 20185316
Inhibition (binding) Inhibition of Mycobacterium tuberculosis recombinant DXR expressed in Escherichia coli BL21 (DE3) using DXP as substrate and MgCl2 as cofactor at 100 uM preincubated for 10 mins ChEMBL. 21561155
Inhibition (binding) = 13.9 % Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase assessed as inhibition of glutamine synthesis from glutamic acid at 1 mM after 15 min by biosynthetic assay ChEMBL. 15161194
Inhibition (binding) = 17.5 % Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase at 1 mM after 30 min by hemibiosynthetic assay ChEMBL. 15161194
Inhibition (binding) = 52.8 % Inhibition of Oryza sativa cv. Gigante vercellese (rice) glutamine synthetase at 1 mM by transferase assay ChEMBL. 15161194
IZ (functional) = 9 mm Antibacterial activity against Escherichia coli pTMV19 ChEMBL. 17149863
IZ (functional) = 9 mm Antibacterial activity against Escherichia coli pTMV19 ChEMBL. 17149863
IZ (functional) = 12 mm Antibacterial activity against Escherichia coli pTMV19 in presence of mevalonate ChEMBL. 17149863
IZ (functional) = 12 mm Antibacterial activity against Escherichia coli pTMV19 in presence of mevalonate ChEMBL. 17149863
IZ (functional) = 13 mm Antibacterial activity against Escherichia coli W3110 ChEMBL. 17149863
IZ (functional) = 13 mm Antibacterial activity against Escherichia coli W3110 ChEMBL. 17149863
Ki (binding) = 0.023 uM Binding affinity towards farnesyl Pyrophosphate Synthase using [14C]- isopentenyl pyrophosphate as radioligand ChEMBL. 14613320
Ki (binding) = 0.023 uM Binding affinity towards farnesyl Pyrophosphate Synthase using [14C]- isopentenyl pyrophosphate as radioligand ChEMBL. 14613320
LD50 (ADMET) > 991 uM Toxicity evaluated against human nasopharyngeal carcinoma KB cell line ChEMBL. 14695831
LD50 (ADMET) > 991 uM Toxicity evaluated against human nasopharyngeal carcinoma KB cell line ChEMBL. 14695831
LD50 (ADMET) > 992 uM 50% lethal dose for inhibition of KB cells growth ChEMBL. 12086478
LD50 (ADMET) > 992 uM 50% lethal dose for inhibition of KB cells growth ChEMBL. 12086478
LED (functional) = 0.01 mgP kg-1 Bone resorption activity in rats. ChEMBL. 12086477
Log IC50 (functional) = 4.27 Predicted pIC50 against Tryomastigotes Brucei rhodesiense. ChEMBL. 12086478
Log IC50 (binding) = 6.62 Inhibitory activity against farnesyl Pyrophosphate Synthase expressed as #NAME? (M) ChEMBL. 14613320
TI (ADMET) > 11.4 Therapeutic index was expressed as ratio of LD50 for KB cell line to IC50 against Entamoeba histolytica ChEMBL. 14695831
TI (ADMET) > 19 Therapeutic index measured as the ratio of LD50 (KB cells) to IC50 (T.b. rhodesiense) ChEMBL. 12086478
TI (ADMET) > 93.5000000000001 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

9 literature references were collected for this gene.

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