Detailed information for compound 114926

Basic information

Technical information
  • TDR Targets ID: 114926
  • Name: [4-[[2-[2-(4-aminophenyl)ethyl]-6-hydroxy-4-o xo-2-propan-2-yl-3H-pyran-5-yl]sulfanyl]-5-te rt-butyl-2-methylphenyl] N-ethylsulfamate
  • MW: 576.768 | Formula: C29H40N2O6S2
  • H donors: 3 H acceptors: 4 LogP: 6.61 Rotable bonds: 11
    Rule of 5 violations (Lipinski): 2
  • SMILES: CCNS(=O)(=O)Oc1cc(c(cc1C)SC1=C(O)OC(CC1=O)(CCc1ccc(cc1)N)C(C)C)C(C)(C)C
  • InChi: 1S/C29H40N2O6S2/c1-8-31-39(34,35)37-24-16-22(28(5,6)7)25(15-19(24)4)38-26-23(32)17-29(18(2)3,36-27(26)33)14-13-20-9-11-21(30)12-10-20/h9-12,15-16,18,31,33H,8,13-14,17,30H2,1-7H3
  • InChiKey: DKMXEBZKRGKHRS-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • [4-[[2-[2-(4-aminophenyl)ethyl]-6-hydroxy-2-isopropyl-4-oxo-3H-pyran-5-yl]sulfanyl]-5-tert-butyl-2-methyl-phenyl] N-ethylsulfamate
  • N-ethylsulfamic acid [4-[[2-[2-(4-aminophenyl)ethyl]-6-hydroxy-2-isopropyl-4-oxo-3H-pyran-5-yl]thio]-5-tert-butyl-2-methylphenyl] ester
  • [4-[[2-[2-(4-aminophenyl)ethyl]-6-hydroxy-4-oxo-2-propan-2-yl-3H-pyran-5-yl]sulfanyl]-5-tert-butyl-2-methyl-phenyl] N-ethylsulfamate
  • N-ethylsulfamic acid [4-[[2-[2-(4-aminophenyl)ethyl]-6-hydroxy-2-isopropyl-4-keto-3H-pyran-5-yl]thio]-5-tert-butyl-2-methyl-phenyl] ester
  • [4-[[6-[2-(4-aminophenyl)ethyl]-2-hydroxy-4-oxo-6-propan-2-yl-5H-pyran-3-yl]sulfanyl]-5-tert-butyl-2-methylphenyl] N-ethylsulfamate
  • [4-[[6-[2-(4-aminophenyl)ethyl]-2-hydroxy-6-isopropyl-4-oxo-5H-pyran-3-yl]sulfanyl]-5-tert-butyl-2-methyl-phenyl] N-ethylsulfamate
  • N-ethylsulfamic acid [4-[[6-[2-(4-aminophenyl)ethyl]-2-hydroxy-6-isopropyl-4-oxo-5H-pyran-3-yl]thio]-5-tert-butyl-2-methylphenyl] ester
  • N-ethylsulfamic acid [4-[[6-[2-(4-aminophenyl)ethyl]-2-hydroxy-6-isopropyl-4-keto-5H-pyran-3-yl]thio]-5-tert-butyl-2-methyl-phenyl] ester
  • [4-[[6-[2-(4-aminophenyl)ethyl]-2-hydroxy-4-oxo-6-propan-2-yl-5H-pyran-3-yl]sulfanyl]-5-tert-butyl-2-methyl-phenyl] N-ethylsulfamate
  • Dihydropyran-2-one deriv. 67
  • (+/-)-N-Ethylsulfamic acid, 4-[6-[2-(4-amino-phenyl)-ethyl]-4-hydroxy-6-isopropyl-2-oxo-5,6-dihydro-2H-pyran-3-ylsulfanyl]-5-tert-butyl-2-methyl-phenyl ester
  • 263843-06-7(HCL SALT)
  • AIDS-085459
  • AIDS085459

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Human immunodeficiency virus 1 Human immunodeficiency virus type 1 protease Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Schistosoma mansoni intracisternal A-particle retropepsin (A02 family) Get druggable targets OG5_131408 All targets in OG5_131408
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Entamoeba histolytica retroviral aspartyl protease domain-containing protein Human immunodeficiency virus type 1 protease   99 aa 103 aa 31.1 %
Entamoeba histolytica retroviral aspartyl protease domain-containing protein Human immunodeficiency virus type 1 protease   99 aa 103 aa 31.1 %
Giardia lamblia DNA-directed RNA polymerase subunit D Human immunodeficiency virus type 1 protease   99 aa 90 aa 27.8 %
Trypanosoma brucei variant surface glycoprotein (VSG), putative Human immunodeficiency virus type 1 protease   99 aa 80 aa 27.5 %
Mycobacterium leprae Hypothetical protein Human immunodeficiency virus type 1 protease   99 aa 86 aa 27.9 %
Candida albicans dethiobiotin synthetase Human immunodeficiency virus type 1 protease   99 aa 90 aa 22.2 %
Candida albicans dethiobiotin synthetase Human immunodeficiency virus type 1 protease   99 aa 90 aa 22.2 %
Echinococcus multilocularis Chromobox protein 3 Human immunodeficiency virus type 1 protease   99 aa 95 aa 28.4 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Entamoeba histolytica isopentenyl-diphosphate delta-isomerase, putative 0.006 0.0308 1
Mycobacterium ulcerans isopentenyl pyrophosphate isomerase 0.006 0.0308 0.2782
Mycobacterium leprae POSSIBLE L-LACTATE DEHYDROGENASE (CYTOCHROME) LLDD2 0.0168 0.1022 0.1762
Treponema pallidum methylgalactoside ABC transporter, periplasmic galactose-binding protein (mglB-2) 0.0869 0.5646 1
Trichomonas vaginalis sensory transduction histidine kinase, putative 0.0024 0.0069 0.5
Mycobacterium leprae Possible D-ribose-binding protein 0.0869 0.5646 1
Schistosoma mansoni tar DNA-binding protein 0.0061 0.0313 0.0177
Mycobacterium tuberculosis Probable sensor protein KdpD 0.0019 0.0033 0.032
Trichomonas vaginalis sensory transduction histidine kinase bacterial, putative 0.0024 0.0069 0.5
Trypanosoma brucei isopentenyl-diphosphate delta-isomerase (type II) 0.006 0.0308 0.5
Wolbachia endosymbiont of Brugia malayi signal transduction histidine kinase and receiver 0.0024 0.0069 1
Echinococcus multilocularis tar DNA binding protein 0.0061 0.0313 1
Onchocerca volvulus Bile acid receptor homolog 0.0158 0.0952 0.5
Brugia malayi RNA recognition motif domain containing protein 0.0061 0.0313 0.2147
Mycobacterium tuberculosis Two component sensory transduction histidine kinase MtrB 0.0019 0.0033 0.032
Trichomonas vaginalis two component sensor and regulator histidine kinase bacteria, putative 0.0024 0.0069 0.5
Chlamydia trachomatis two component regulatory system sensor histidine kinase 0.0019 0.0033 0.5
Echinococcus granulosus tar DNA binding protein 0.0061 0.0313 1
Mycobacterium tuberculosis Possible two component system response sensor kinase membrane associated PhoR 0.0019 0.0033 0.032
Mycobacterium tuberculosis Possible L-lactate dehydrogenase (cytochrome) LldD2 0.0168 0.1022 1
Schistosoma mansoni family A2 unassigned peptidase (A02 family) 0.0278 0.1744 0.1628
Loa Loa (eye worm) hypothetical protein 0.0158 0.0952 1
Treponema pallidum methylgalactoside ABC transporter, periplasmic galactose-binding protein (mglB-1) 0.0869 0.5646 1
Brugia malayi TAR-binding protein 0.0061 0.0313 0.2147
Schistosoma mansoni tar DNA-binding protein 0.0061 0.0313 0.0177
Leishmania major isopentenyl-diphosphate delta-isomerase, putative,isomerase, putative 0.006 0.0308 0.5
Schistosoma mansoni tar DNA-binding protein 0.0061 0.0313 0.0177
Schistosoma mansoni tar DNA-binding protein 0.0061 0.0313 0.0177
Schistosoma mansoni tar DNA-binding protein 0.0061 0.0313 0.0177
Mycobacterium ulcerans L-lactate dehydrogenase (cytochrome) LldD1 0.006 0.0308 0.2782
Mycobacterium ulcerans L-lactate dehydrogenase (cytochrome) LldD2 0.0168 0.1022 1
Mycobacterium tuberculosis Two component sensor histidine kinase TrcS 0.0019 0.0033 0.032
Trichomonas vaginalis receptor histidine kinase, putative 0.0024 0.0069 0.5
Mycobacterium tuberculosis Two component sensor histidine kinase PrrB 0.0019 0.0033 0.032
Brugia malayi ecdysteroid receptor 0.0158 0.0952 1
Trichomonas vaginalis receptor histidine kinase, putative 0.0024 0.0069 0.5
Mycobacterium tuberculosis Possible two component sensor kinase TcrY 0.0019 0.0033 0.032
Trichomonas vaginalis sensor histidine kinase, putative 0.0024 0.0069 0.5
Brugia malayi RNA binding protein 0.0061 0.0313 0.2147
Trichomonas vaginalis sensory transduction histidine kinase bacterial, putative 0.0024 0.0069 0.5
Mycobacterium tuberculosis Two component sensor kinase MprB 0.0019 0.0033 0.032

Activities

Activity type Activity value Assay description Source Reference
EC50 (functional) = 0.63 uM In vitro inhibition of HIV-1 (IIIB) cytopathic effects in CEM (human leukaemia) cells. ChEMBL. 10465549
EC50 (functional) = 0.7 uM Effective concentration at which 50% of the HIV-IIIB-infected human lymphocyte-derived CEM cells protected from HIV-1 infection ChEMBL. 10715152
IC50 (binding) = 4.3 nM Tested in vitro for HIV protease (PR) binding affinity ChEMBL. 10465549
IC50 (binding) = 4.3 nM Activity of potent nonpeptidic inhibitor against protease ChEMBL. 10715152
IC50 (binding) = 4.3 nM Tested in vitro for HIV protease (PR) binding affinity ChEMBL. 10465549
IC50 (binding) = 4.3 nM Activity of potent nonpeptidic inhibitor against protease ChEMBL. 10715152
TC50 (functional) = 74 uM In vitro Cytotoxicity against uninfected CEM (human leukaemia) cells. ChEMBL. 10465549
TC50 (ADMET) = 83 uM Concentration which elicits cytotoxicity in 50% of uninfected human lymphocyte derived CEM cells ChEMBL. 10715152
TC50 (ADMET) = 83 uM Concentration which elicits cytotoxicity in 50% of uninfected human lymphocyte derived CEM cells ChEMBL. 10715152
Therapeutic index (ADMET) = 117 Therapeutic index of the compound was determined ChEMBL. 10465549

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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