Detailed information for compound 201486

Basic information

Technical information
  • TDR Targets ID: 201486
  • Name: [(2R,3R)-3-acetyloxy-1-(hydroxyamino)-1-oxo-4 -phosphonooxybutan-2-yl] acetate
  • MW: 315.171 | Formula: C8H14NO10P
  • H donors: 4 H acceptors: 7 LogP: -2.82 Rotable bonds: 10
    Rule of 5 violations (Lipinski): 1
  • SMILES: ONC(=O)[C@@H]([C@H](OC(=O)C)COP(=O)(O)O)OC(=O)C
  • InChi: 1S/C8H14NO10P/c1-4(10)18-6(3-17-20(14,15)16)7(8(12)9-13)19-5(2)11/h6-7,13H,3H2,1-2H3,(H,9,12)(H2,14,15,16)/t6-,7-/m1/s1
  • InChiKey: KQWSEXYWBMLBQI-RNFRBKRXSA-N  


Substructure search Similarity search

Network

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Synonyms

  • [(1R,2R)-2-acetoxy-1-(hydroxycarbamoyl)-3-phosphonooxy-propyl] acetate
  • acetic acid [(1R,2R)-2-acetoxy-1-[(hydroxyamino)-oxomethyl]-3-phosphonooxypropyl] ester
  • [(2R,3R)-3-acetyloxy-1-(hydroxyamino)-1-oxo-4-phosphonooxy-butan-2-yl] ethanoate
  • acetic acid [(1R,2R)-2-acetoxy-1-(hydroxycarbamoyl)-3-phosphonooxy-propyl] ester

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens phosphogluconate dehydrogenase Starlite/ChEMBL References
Trypanosoma brucei 6-phosphogluconate dehydrogenase, decarboxylating Starlite/ChEMBL References
Ovis aries 6-phosphogluconate dehydrogenase, decarboxylating Starlite/ChEMBL References
Francisella tularensis subsp. tularensis (strain SCHU S4 / Schu 4) Arabinose phosphate isomerase Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Trichomonas vaginalis 6-phosphogluconate dehydrogenase, putative Get druggable targets OG5_127175 All targets in OG5_127175
Trypanosoma brucei 6-phosphogluconate dehydrogenase, decarboxylating Get druggable targets OG5_127175 All targets in OG5_127175
Candida albicans similar to S. cerevisiae GND1 (YHR183W) and GND2 (YGR256W) 6-phosphogluconate dehydrogenase Get druggable targets OG5_127175 All targets in OG5_127175
Trypanosoma congolense 6-phosphogluconate dehydrogenase, decarboxylating, putative Get druggable targets OG5_127175 All targets in OG5_127175
Mycobacterium tuberculosis Probable 6-phosphogluconate dehydrogenase, decarboxylating Gnd2 Get druggable targets OG5_127175 All targets in OG5_127175
Chlamydia trachomatis 6-phosphogluconate dehydrogenase Get druggable targets OG5_127175 All targets in OG5_127175
Leishmania infantum 6-phosphogluconate dehydrogenase, decarboxylating, putative Get druggable targets OG5_127175 All targets in OG5_127175
Plasmodium knowlesi 6-phosphogluconate dehydrogenase, decarboxylating, putative Get druggable targets OG5_127175 All targets in OG5_127175
Trichomonas vaginalis 3-hydroxyisobutyrate dehydrogenase, putative Get druggable targets OG5_127175 All targets in OG5_127175
Brugia malayi 6-phosphogluconate dehydrogenase, decarboxylating, putative Get druggable targets OG5_127175 All targets in OG5_127175
Mycobacterium leprae PROBABLE 6-PHOSPHOGLUCONATE DEHYDROGENASE GND1 Get druggable targets OG5_127175 All targets in OG5_127175
Leishmania mexicana 6-phosphogluconate dehydrogenase, decarboxylating, putative Get druggable targets OG5_127175 All targets in OG5_127175
Theileria parva 6-phosphogluconate dehydrogenase, putative Get druggable targets OG5_127175 All targets in OG5_127175
Plasmodium falciparum 6-phosphogluconate dehydrogenase, decarboxylating, putative Get druggable targets OG5_127175 All targets in OG5_127175
Toxoplasma gondii 6-phosphogluconate dehydrogenase Get druggable targets OG5_127175 All targets in OG5_127175
Leishmania braziliensis 6-phosphogluconate dehydrogenase, decarboxylating, putative Get druggable targets OG5_127175 All targets in OG5_127175
Candida albicans potential phosphosugar binding domain Get druggable targets OG5_130715 All targets in OG5_130715
Mycobacterium ulcerans 6-phosphogluconate dehydrogenase Get druggable targets OG5_127175 All targets in OG5_127175
Leishmania major 6-phosphogluconate dehydrogenase, decarboxylating, putative Get druggable targets OG5_127175 All targets in OG5_127175
Treponema pallidum 6-phosphogluconate dehydrogenase Get druggable targets OG5_127175 All targets in OG5_127175
Candida albicans similar to S. cerevisiae GND1 (YHR183W) and GND2 (YGR256W) 6-phosphogluconate dehydrogenase Get druggable targets OG5_127175 All targets in OG5_127175
Chlamydia trachomatis GutQ/KpsF family sugar-phosphate isomerase Get druggable targets OG5_130715 All targets in OG5_130715
Mycobacterium tuberculosis Probable 6-phosphogluconate dehydrogenase Gnd1 Get druggable targets OG5_127175 All targets in OG5_127175
Plasmodium vivax 6-phosphogluconate dehydrogenase, decarboxylating, putative Get druggable targets OG5_127175 All targets in OG5_127175
Trypanosoma cruzi 6-phosphogluconate dehydrogenase, decarboxylating, putative Get druggable targets OG5_127175 All targets in OG5_127175
Schistosoma mansoni 6-phosphogluconate dehydrogenase Get druggable targets OG5_127175 All targets in OG5_127175
Toxoplasma gondii 6-phosphogluconate dehydrogenase Get druggable targets OG5_127175 All targets in OG5_127175
Plasmodium berghei 6-phosphogluconate dehydrogenase, decarboxylating, putative Get druggable targets OG5_127175 All targets in OG5_127175
Loa Loa (eye worm) pgd protein Get druggable targets OG5_127175 All targets in OG5_127175
Mycobacterium ulcerans 6-phosphogluconate dehydrogenase Get druggable targets OG5_127175 All targets in OG5_127175
Giardia lamblia 6-phosphogluconate dehydrogenase, decarboxylating Get druggable targets OG5_127175 All targets in OG5_127175
Plasmodium yoelii 6-phosphogluconate dehydrogenase, decarboxylating Get druggable targets OG5_127175 All targets in OG5_127175
Schistosoma japonicum ko:K00033 6-phosphogluconate dehydrogenase [EC1.1.1.44], putative Get druggable targets OG5_127175 All targets in OG5_127175
Echinococcus multilocularis 6 phosphogluconate dehydrogenase Get druggable targets OG5_127175 All targets in OG5_127175
Candida albicans potential phosphosugar binding domain Get druggable targets OG5_130715 All targets in OG5_130715
Neospora caninum 6-phosphogluconate dehydrogenase, decarboxylating (EC 1.1.1.44), related Get druggable targets OG5_127175 All targets in OG5_127175
Leishmania donovani 6-phosphogluconate dehydrogenase, decarboxylating, putative Get druggable targets OG5_127175 All targets in OG5_127175
Echinococcus granulosus 6 phosphogluconate dehydrogenase Get druggable targets OG5_127175 All targets in OG5_127175
Babesia bovis 6-phosphogluconate dehydrogenase, putative Get druggable targets OG5_127175 All targets in OG5_127175
Trichomonas vaginalis 6-phosphogluconate dehydrogenase, putative Get druggable targets OG5_127175 All targets in OG5_127175
Trypanosoma brucei gambiense 6-phosphogluconate dehydrogenase, decarboxylating, putative Get druggable targets OG5_127175 All targets in OG5_127175
Neospora caninum 6-phosphogluconate dehydrogenase, decarboxylating (EC 1.1.1.44), related Get druggable targets OG5_127175 All targets in OG5_127175
Trypanosoma cruzi 6-phosphogluconate dehydrogenase, decarboxylating Get druggable targets OG5_127175 All targets in OG5_127175
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Onchocerca volvulus 6-phosphogluconate dehydrogenase, decarboxylating   483 aa 469 aa 69.5 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Echinococcus granulosus glycine receptor subunit beta 0.006 0.1496 0.1496
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Leishmania major 6-phosphogluconate dehydrogenase, decarboxylating, putative 0.0218 1 0.5
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Echinococcus multilocularis glycine receptor subunit alpha 1 0.006 0.1496 0.1496
Trypanosoma cruzi 6-phosphogluconate dehydrogenase, decarboxylating, putative 0.0218 1 1
Brugia malayi acetylcholine receptor, alpha-type subunit unc-38 precursor 0.006 0.1496 0.1496
Loa Loa (eye worm) excitatory GABA receptor EXP-1A 0.006 0.1496 0.1496
Plasmodium vivax 6-phosphogluconate dehydrogenase, decarboxylating, putative 0.0218 1 0.5
Mycobacterium ulcerans 6-phosphogluconate dehydrogenase 0.0218 1 0.5
Echinococcus multilocularis glycine receptor subunit alpha 1 0.006 0.1496 0.1496
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.006 0.1496 0.1496
Mycobacterium leprae PROBABLE 6-PHOSPHOGLUCONATE DEHYDROGENASE GND1 0.0218 1 0.5
Schistosoma mansoni Cys-loop ligand gated ion channel subunit 0.006 0.1496 0.1496
Onchocerca volvulus 0.006 0.1496 1
Brugia malayi excitatory GABA receptor EXP-1A 0.006 0.1496 0.1496
Brugia malayi nicotinic acetylcholine receptor beta-1 chain precursor 0.006 0.1496 0.1496
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.006 0.1496 0.1496
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Trichomonas vaginalis 6-phosphogluconate dehydrogenase, putative 0.0218 1 0.5
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.006 0.1496 0.1496
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.006 0.1496 0.1496
Onchocerca volvulus 0.006 0.1496 1
Schistosoma mansoni transcription initiation factor iia (tfiia) gamma chain 0.0088 0.3002 0.3002
Treponema pallidum 6-phosphogluconate dehydrogenase 0.0218 1 0.5
Brugia malayi Neurotransmitter-gated ion-channel transmembrane region family protein 0.006 0.1496 0.1496
Schistosoma mansoni nAChR subunit 0.006 0.1496 0.1496
Trypanosoma cruzi 6-phosphogluconate dehydrogenase, decarboxylating 0.013 0.5251 0.3213
Echinococcus granulosus glycine receptor subunit alpha 1 0.006 0.1496 0.1496
Onchocerca volvulus 0.006 0.1496 1
Entamoeba histolytica hypothetical protein 0.0032 0 0.5
Schistosoma mansoni nAChR subunit 0.006 0.1496 0.1496
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Brugia malayi Hypothetical glycine receptor like protein T20B12.9 in chromosome III 0.006 0.1496 0.1496
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Giardia lamblia 6-phosphogluconate dehydrogenase, decarboxylating 0.0218 1 0.5
Mycobacterium tuberculosis Probable 6-phosphogluconate dehydrogenase Gnd1 0.0218 1 0.5
Echinococcus granulosus Cys loop ligand gated ion channel subunit 0.006 0.1496 0.1496
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Schistosoma mansoni Cys-loop ligand gated ion channel subunit 0.006 0.1496 0.1496
Schistosoma mansoni nAChR subunit 0.006 0.1496 0.1496
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Brugia malayi Cation transporter family protein 0.006 0.1496 0.1496
Brugia malayi acetylcholine receptor protein, alpha-like chain, putative 0.006 0.1496 0.1496
Trypanosoma brucei 6-phosphogluconate dehydrogenase, decarboxylating 0.0218 1 0.5
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Echinococcus granulosus nicotinic acetylcholine receptor alpha subunit 0.006 0.1496 0.1496
Echinococcus granulosus acetylcholine receptor subunit beta 1 0.006 0.1496 0.1496
Echinococcus granulosus nicotinic acetylcholine receptor a11 subunit 0.006 0.1496 0.1496
Trichomonas vaginalis 6-phosphogluconate dehydrogenase, putative 0.0218 1 0.5
Loa Loa (eye worm) ACC-1 protein 0.006 0.1496 0.1496
Echinococcus multilocularis nicotinic acetylcholine receptor alpha subunit 0.006 0.1496 0.1496
Mycobacterium tuberculosis Probable 6-phosphogluconate dehydrogenase, decarboxylating Gnd2 0.0218 1 0.5
Echinococcus granulosus neuronal acetylcholine receptor subunit alpha 4 0.006 0.1496 0.1496
Trichomonas vaginalis 3-hydroxyisobutyrate dehydrogenase, putative 0.0218 1 0.5
Mycobacterium ulcerans 6-phosphogluconate dehydrogenase 0.0218 1 0.5
Schistosoma mansoni Cys-loop ligand gated ion channel subunit 0.006 0.1496 0.1496
Echinococcus multilocularis glycine receptor subunit beta 0.006 0.1496 0.1496
Loa Loa (eye worm) acetylcholine receptor alpha subunit 0.006 0.1496 0.1496
Echinococcus granulosus nAChR subunit 0.006 0.1496 0.1496
Schistosoma mansoni nAChR subunit 0.006 0.1496 0.1496
Loa Loa (eye worm) ACC-1 protein 0.006 0.1496 0.1496
Echinococcus granulosus nicotinic acetylcholine receptor subunit alpha 8 0.006 0.1496 0.1496
Echinococcus granulosus 6 phosphogluconate dehydrogenase 0.0218 1 1
Echinococcus granulosus nicotinic acetylcholine receptor beta 1 subunit 0.006 0.1496 0.1496
Brugia malayi Cation transporter family protein 0.006 0.1496 0.1496
Echinococcus multilocularis glycine receptor subunit alpha 1 0.006 0.1496 0.1496
Schistosoma mansoni nAChR subunit 0.006 0.1496 0.1496
Onchocerca volvulus Putative nachr subunit 0.006 0.1496 1
Brugia malayi Neurotransmitter-gated ion-channel transmembrane region family protein 0.006 0.1496 0.1496
Echinococcus multilocularis neuronal acetylcholine receptor subunit alpha 4 0.006 0.1496 0.1496
Brugia malayi acetylcholine receptor alpha subunit precursor, putative 0.006 0.1496 0.1496
Loa Loa (eye worm) glutamate-gated chloride channel alpha3A subunit 0.006 0.1496 0.1496
Schistosoma mansoni nAChR subunit 0.006 0.1496 0.1496
Schistosoma mansoni 6-phosphogluconate dehydrogenase 0.0218 1 1
Echinococcus granulosus glycine receptor subunit alpha 1 0.006 0.1496 0.1496
Echinococcus multilocularis nicotinic acetylcholine receptor a11 subunit 0.006 0.1496 0.1496
Schistosoma mansoni nAChR subunit (ShAR1-beta2-like) 0.006 0.1496 0.1496
Plasmodium falciparum 6-phosphogluconate dehydrogenase, decarboxylating, putative 0.0218 1 0.5
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Toxoplasma gondii 6-phosphogluconate dehydrogenase 0.0218 1 0.5
Schistosoma mansoni nAChR subunit 0.006 0.1496 0.1496
Brugia malayi nicotinic acetylcholine receptor alpha subunit, putative 0.006 0.1496 0.1496
Brugia malayi Neurotransmitter-gated ion-channel transmembrane region family protein 0.006 0.1496 0.1496
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Echinococcus multilocularis glycine receptor subunit beta 0.006 0.1496 0.1496
Loa Loa (eye worm) nicotinic acetylcholine receptor non-alpha subunit 0.006 0.1496 0.1496
Brugia malayi Cation transporter family protein 0.006 0.1496 0.1496
Echinococcus multilocularis nicotinic acetylcholine receptor beta 1 subunit 0.006 0.1496 0.1496
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Onchocerca volvulus 0.006 0.1496 1
Loa Loa (eye worm) pgd protein 0.0218 1 1
Echinococcus multilocularis 6 phosphogluconate dehydrogenase 0.0218 1 1
Echinococcus multilocularis nAChR subunit 0.006 0.1496 0.1496
Echinococcus granulosus nicotinic acetylcholine receptor subunit type 0.006 0.1496 0.1496
Loa Loa (eye worm) ligand-Gated ion Channel family member 0.006 0.1496 0.1496
Schistosoma mansoni nAChR subunit (ShAR1-alpha-like) 0.006 0.1496 0.1496
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.006 0.1496 0.1496
Schistosoma mansoni nAChR subunit (ShAR1-beta-like) 0.006 0.1496 0.1496
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Echinococcus granulosus glycine receptor subunit alpha 1 0.006 0.1496 0.1496
Toxoplasma gondii 6-phosphogluconate dehydrogenase 0.0218 1 0.5
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Echinococcus multilocularis Cys loop ligand gated ion channel subunit 0.006 0.1496 0.1496
Brugia malayi gamma-aminobutyric-acid receptor beta subunit precursor 0.006 0.1496 0.1496
Loa Loa (eye worm) LGC-31 protein 0.006 0.1496 0.1496
Echinococcus granulosus glycine receptor subunit beta 0.006 0.1496 0.1496
Echinococcus multilocularis acetylcholine receptor subunit beta 1 0.006 0.1496 0.1496
Onchocerca volvulus 0.006 0.1496 1
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Loa Loa (eye worm) nicotinic acetylcholine receptor alpha subunit 0.006 0.1496 0.1496
Onchocerca volvulus 0.006 0.1496 1
Brugia malayi Neurotransmitter-gated ion-channel ligand binding domain containing protein 0.006 0.1496 0.1496
Chlamydia trachomatis 6-phosphogluconate dehydrogenase 0.0218 1 1
Loa Loa (eye worm) hypothetical protein 0.006 0.1496 0.1496
Echinococcus multilocularis nicotinic acetylcholine receptor subunit alpha 8 0.006 0.1496 0.1496

Activities

Activity type Activity value Assay description Source Reference
Activity (functional) = 229 uM Antiparasitic activity against Trypanosoma brucei infected in rat L6 cells ChEMBL. 21236668
IC50 (functional) uM In vitro antiparasitic activity of the compound was determined against Leishmania donovani; na means data not availabel ChEMBL. 15189039
IC50 (functional) NA 0 uM In vitro antiparasitic activity of the compound was determined against Leishmania donovani; na means data not availabel ChEMBL. 15189039
IC50 (binding) = 7 uM Inhibition of Francisella tularensis N-terminal hexahistidine-tagged arabinose phosphate isomerase expressed in Escherichia coli BL21(DE3) after 3 hrs ChEMBL. 21236668
IC50 (functional) > 159 uM In vitro antiparasitic activity was determined against Plasmodium falciparum ChEMBL. 15189039
IC50 (functional) > 159 uM In vitro antiparasitic activity was determined against Plasmodium falciparum ChEMBL. 15189039
IC50 (functional) = 229 uM In vitro antiparasitic activity was determined against Trypanosoma brucei ChEMBL. 15189039
IC50 (functional) = 229 uM In vitro antiparasitic activity was determined against Trypanosoma brucei ChEMBL. 15189039
IC50 (functional) > 285 uM In vitro antiparasitic activity was determined against Trypanosoma cruzi ChEMBL. 15189039
IC50 (functional) > 285 uM In vitro cytotoxic activity of the compound was determined against L6 cells ChEMBL. 15189039
IC50 (functional) > 285 uM In vitro antiparasitic activity was determined against Trypanosoma cruzi ChEMBL. 15189039
Ki (binding) = 360 nM Inhibition of sheep 6-phosphogluconate dehydrogenase ChEMBL. 21236668
Ki (binding) = 0.08 uM Inhibition constant against 6-phosphogluconate dehydrogenase of Trypanosoma brucei expressed in Escherichia coli ChEMBL. 15189039
Ki (binding) = 0.08 uM Inhibition constant against 6-phosphogluconate dehydrogenase of Trypanosoma brucei expressed in Escherichia coli ChEMBL. 15189039
Ki (binding) = 0.08 uM Inhibition of Trypanosoma brucei 6-phosphogluconate dehydrogenase ChEMBL. 21236668
Ki (binding) = 0.36 uM Inhibition constant against 6-phosphogluconate dehydrogenase of sheep liver ChEMBL. 15189039
Ki (binding) = 0.36 uM Inhibition constant against 6-phosphogluconate dehydrogenase of sheep liver ChEMBL. 15189039
Ki (binding) = 0.36 uM Inhibition of sheep 6PGDH expressed in Escherichia coli by spectroscopy ChEMBL. 20598892
Ratio (binding) = 4.5 Selectivity ratio of inhibition constant of compound against 6-phosphogluconate dehydrogenase of sheep to 6-phosphogluconate dehydrogenase of trypanosoma brucei ChEMBL. 15189039

Phenotypes

Whole-cell/tissue/organism interactions

We have no records of whole-cell/tissue assays done with this compound What does this mean?

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

2 literature references were collected for this gene.

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