Detailed information for compound 172330

Basic information

Technical information
  • TDR Targets ID: 172330
  • Name: (2R,3R,4R,5R)-2,5-bis[(2-fluorophenyl)methoxy ]-3,4-dihydroxy-N-[(1S,2R)-2-hydroxy-2,3-dihy dro-1H-inden-1-yl]-N'-[(2R)-2-hydroxy-2,3-dih ydro-1H-inden-1-yl]hexanediamide
  • MW: 688.714 | Formula: C38H38F2N2O8
  • H donors: 6 H acceptors: 6 LogP: 3.64 Rotable bonds: 15
    Rule of 5 violations (Lipinski): 3
  • SMILES: O=C([C@@H]([C@@H]([C@H]([C@H](C(=O)N[C@@H]1[C@H](O)Cc2c1cccc2)OCc1ccccc1F)O)O)OCc1ccccc1F)NC1[C@H](O)Cc2c1cccc2
  • InChi: 1S/C38H38F2N2O8/c39-27-15-7-3-11-23(27)19-49-35(37(47)41-31-25-13-5-1-9-21(25)17-29(31)43)33(45)34(46)36(50-20-24-12-4-8-16-28(24)40)38(48)42-32-26-14-6-2-10-22(26)18-30(32)44/h1-16,29-36,43-46H,17-20H2,(H,41,47)(H,42,48)/t29-,30-,31+,32?,33-,34-,35-,36-/m1/s1
  • InChiKey: LYHLPPXMBKMSSZ-NFSPSGFISA-N  

Network

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Synonyms

  • (2R,3R,4R,5R)-2,5-bis[(2-fluorophenyl)methoxy]-3,4-dihydroxy-N-[(1S,2R)-2-hydroxyindan-1-yl]-N'-[(2R)-2-hydroxyindan-1-yl]hexanediamide
  • (2R,3R,4R,5R)-2,5-bis[(2-fluorophenyl)methoxy]-3,4-dihydroxy-N-[(1S,2R)-2-hydroxy-1-indanyl]-N'-[(2R)-2-hydroxy-1-indanyl]hexanediamide
  • (2R,3R,4R,5R)-2,5-bis[(2-fluorobenzyl)oxy]-3,4-dihydroxy-N-[(1S,2R)-2-hydroxyindan-1-yl]-N'-[(2R)-2-hydroxyindan-1-yl]adipamide

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
Candida albicans dethiobiotin synthetase Human immunodeficiency virus type 1 protease   99 aa 90 aa 22.2 %
Giardia lamblia DNA-directed RNA polymerase subunit D Human immunodeficiency virus type 1 protease   99 aa 90 aa 27.8 %
Candida albicans dethiobiotin synthetase Human immunodeficiency virus type 1 protease   99 aa 90 aa 22.2 %
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 %
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 %
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
Mycobacterium tuberculosis Probable polyketide synthase Pks15 0.0391 0.0933 0.0864
Mycobacterium tuberculosis Phenolpthiocerol synthesis type-I polyketide synthase PpsA 0.0968 0.4555 0.5856
Mycobacterium tuberculosis Probable multifunctional mycocerosic acid synthase membrane-associated Mas 0.1028 0.4933 0.6376
Mycobacterium tuberculosis Probable fatty acid synthase Fas (fatty acid synthetase) 0.0304 0.0384 0.0108
Mycobacterium ulcerans thioesterase 0.0806 0.3541 0.4682
Mycobacterium ulcerans phenolpthiocerol synthesis type-I polyketide synthase PpsD 0.0968 0.4555 0.6023
Loa Loa (eye worm) AMP-binding enzyme family protein 0.0904 0.4155 0.4782
Mycobacterium leprae Probable polyketide synthase Pks1 0.1028 0.4933 0.6337
Mycobacterium ulcerans phenolpthiocerol synthesis type-I polyketide synthase PpsB 0.0779 0.3367 0.4452
Mycobacterium leprae PROBABLE THIOESTERASE TESA 0.0806 0.3541 0.4398
Echinococcus multilocularis calcium:calmodulin dependent 3',5' cyclic 0.0482 0.1504 0.2107
Echinococcus granulosus calcium:calmodulin dependent 3'5' cyclic 0.1378 0.7135 1
Mycobacterium ulcerans phenolpthiocerol synthesis type-I polyketide synthase PpsC 0.1028 0.4933 0.6522
Mycobacterium tuberculosis Phenolpthiocerol synthesis type-I polyketide synthase PpsD 0.0968 0.4555 0.5856
Mycobacterium tuberculosis Probable polyketide synthase Pks1 0.0695 0.2842 0.3495
Loa Loa (eye worm) PDE1B protein 0.1378 0.7135 0.8211
Mycobacterium leprae PHENOLPTHIOCEROL SYNTHESIS TYPE-I POLYKETIDE SYNTHASE PPSB 0.0779 0.3367 0.4155
Toxoplasma gondii 3'5'-cyclic nucleotide phosphodiesterase domain-containing protein 0.0482 0.1504 0.3048
Brugia malayi Methyltransferase-like protein 4 0.0291 0.0306 0.0306
Leishmania major cAMP phosphodiesterase A, putative;with=GeneDB:LinJ18_V3.1100 0.0482 0.1504 1
Loa Loa (eye worm) acyl carrier protein 0.0445 0.127 0.1462
Mycobacterium leprae PHENOLPTHIOCEROL SYNTHESIS TYPE-I POLYKETIDE SYNTHASE PPSD 0.0968 0.4555 0.581
Schistosoma mansoni calcium/calmodulin-dependent 35-cyclic nucleotide phosphodiesterase 0.1378 0.7135 0.8835
Mycobacterium tuberculosis Probable polyketide synthase Pks7 0.1028 0.4933 0.6376
Brugia malayi Probable 3',5'-cyclic phosphodiesterase T04D3.3, putative 0.1378 0.7135 0.7135
Toxoplasma gondii AMP-binding enzyme domain-containing protein 0.0489 0.1547 0.3136
Onchocerca volvulus Fatty acid synthase homolog 0.1744 0.9436 1
Leishmania major hypothetical protein, conserved 0.0291 0.0306 0.2032
Giardia lamblia Methyltransferase like 2 0.0291 0.0306 0.5
Trypanosoma cruzi cAMP phosphodiesterase A, putative 0.0482 0.1504 1
Mycobacterium tuberculosis Polyketide synthase Pks12 0.1028 0.4933 0.6376
Toxoplasma gondii type I fatty acid synthase, putative 0.1028 0.4933 1
Mycobacterium ulcerans thioesterase TesA 0.0806 0.3541 0.4682
Mycobacterium ulcerans phenolpthiocerol synthesis type-I polyketide synthase PpsE 0.064 0.2495 0.3299
Trypanosoma cruzi cAMP phosphodiesterase A, putative 0.0482 0.1504 1
Mycobacterium leprae Probable multifunctional mycocerosic acid synthase membrane associated enzyme Mas 0.1028 0.4933 0.6337
Loa Loa (eye worm) hypothetical protein 0.0542 0.1881 0.2164
Mycobacterium ulcerans fatty acid synthase Fas 0.0304 0.0384 0.0508
Mycobacterium ulcerans polyketide synthase 0.1028 0.4933 0.6522
Trypanosoma brucei cAMP phosphodiesterase A, putative 0.0482 0.1504 1
Schistosoma mansoni methyltransferase-related 0.0291 0.0306 0.0378
Plasmodium vivax 3',5'-cyclic nucleotide phosphodiesterase, putative 0.0482 0.1504 1
Echinococcus multilocularis calcium:calmodulin dependent 3',5' cyclic 0.1378 0.7135 1
Mycobacterium tuberculosis Probable thioesterase TesA 0.0806 0.3541 0.4459
Mycobacterium tuberculosis Polyketide synthetase MbtC (polyketide synthase) 0.0333 0.0564 0.0356
Echinococcus granulosus calcium:calmodulin dependent 3'5' cyclic 0.0482 0.1504 0.2107
Brugia malayi AMP-binding enzyme family protein 0.0904 0.4155 0.4155
Mycobacterium tuberculosis Probable polyketide synthase Pks8 0.0791 0.3447 0.4329
Mycobacterium leprae PHENOLPTHIOCEROL SYNTHESIS TYPE-I POLYKETIDE SYNTHASE PPSA 0.0968 0.4555 0.581
Mycobacterium ulcerans polyketide synthase Pks13 0.1446 0.7562 1
Mycobacterium leprae PHENOLPTHIOCEROL SYNTHESIS TYPE-I POLYKETIDE SYNTHASE PPSC 0.1028 0.4933 0.6337
Chlamydia trachomatis 3-oxoacyl-ACP synthase 0.0243 0 0.5
Schistosoma mansoni intracisternal A-particle retropepsin (A02 family) 0.1528 0.8076 1
Brugia malayi Beta-ketoacyl synthase, N-terminal domain containing protein 0.0968 0.4555 0.4555
Mycobacterium ulcerans polyketide synthase MbtD 0.0297 0.0343 0.0454
Onchocerca volvulus 0.1684 0.9058 0.9285
Mycobacterium tuberculosis Probable polyketide synthase Pks9 0.055 0.1931 0.224
Toxoplasma gondii beta-ketoacyl synthase, N-terminal domain-containing protein 0.0628 0.2419 0.4903
Mycobacterium ulcerans Type I modular polyketide synthase 0.0968 0.4555 0.6023
Mycobacterium tuberculosis Polyketide synthetase MbtD (polyketide synthase) 0.0297 0.0343 0.0052
Brugia malayi AMP-binding enzyme family protein 0.0297 0.0343 0.0343
Toxoplasma gondii type I fatty acid synthase, putative 0.0689 0.2802 0.5682
Loa Loa (eye worm) fatty acid synthase 0.0955 0.4474 0.5149
Mycobacterium tuberculosis Polyketide synthase Pks2 0.0938 0.4368 0.5599
Mycobacterium leprae Polyketide synthase Pks13 0.1446 0.7562 1
Mycobacterium ulcerans multifunctional mycocerosic acid synthase membrane-associated Mas 0.1028 0.4933 0.6522
Wolbachia endosymbiont of Brugia malayi 3-oxoacyl-ACP synthase 0.0243 0 0.5
Mycobacterium tuberculosis Phenyloxazoline synthase MbtB (phenyloxazoline synthetase) 0.0904 0.4155 0.5305
Toxoplasma gondii 3'5'-cyclic nucleotide phosphodiesterase domain-containing protein 0.0482 0.1504 0.3048
Mycobacterium ulcerans polyketide synthase 0.0968 0.4555 0.6023
Mycobacterium ulcerans polyketide synthase Pks9 0.064 0.2495 0.3299
Mycobacterium ulcerans phenolpthiocerol synthesis type-I polyketide synthase PpsA 0.0779 0.3367 0.4452
Mycobacterium tuberculosis Polyketide synthase Pks13 0.1446 0.7562 1
Mycobacterium tuberculosis Phenolpthiocerol synthesis type-I polyketide synthase PpsC 0.0968 0.4555 0.5856
Mycobacterium ulcerans Type I modular polyketide synthase 0.0968 0.4555 0.6023
Plasmodium falciparum 3-oxoacyl-acyl-carrier protein synthase I/II 0.0243 0 0.5
Mycobacterium leprae PHENOLPTHIOCEROL SYNTHESIS TYPE-I POLYKETIDE SYNTHASE PPSE 0.064 0.2495 0.2941
Mycobacterium tuberculosis Probable polyketide synthase Pks5 0.0938 0.4368 0.5599
Loa Loa (eye worm) hypothetical protein 0.1625 0.869 1
Mycobacterium tuberculosis Probable membrane bound polyketide synthase Pks6 0.1446 0.7562 1
Trichomonas vaginalis conserved hypothetical protein 0.0291 0.0306 0.5
Schistosoma mansoni family A2 unassigned peptidase (A02 family) 0.0278 0.0219 0.0272
Mycobacterium ulcerans Type I modular polyketide synthase 0.0968 0.4555 0.6023

Activities

Activity type Activity value Assay description Source Reference
ED50 (functional) = 0.05 uM Anti-HIV-1 activity against Wild type virus in MT-4 cells ChEMBL. 11543677
ED50 (functional) = 0.05 uM Anti-HIV-1 activity against Wild type virus in MT-4 cells ChEMBL. 11543677
ED50 (functional) = 0.08 uM Anti-HIV-1 activity against mutant HIV-1 in MT-4 cells (mutation selected with saquinavir) ChEMBL. 11543677
ED50 (functional) = 0.08 uM Anti-HIV-1 activity against mutant HIV-1 in MT-4 cells (mutation selected with saquinavir) ChEMBL. 11543677
ED50 (functional) = 0.21 uM Anti-HIV-1 activity against mutant HIV-1 in MT-4 cells (mutation selected with nelfinavir) ChEMBL. 11543677
ED50 (functional) = 0.21 uM Anti-HIV-1 activity against mutant HIV-1 in MT-4 cells (mutation selected with nelfinavir) ChEMBL. 11543677
ED50 (functional) = 0.27 uM Anti-HIV-1 activity against mutant HIV-1 in MT-4 cells (mutation selected with compound 1) ChEMBL. 11543677
ED50 (functional) = 0.27 uM Anti-HIV-1 activity against mutant HIV-1 in MT-4 cells (mutation selected with compound 1) ChEMBL. 11543677
ED50 (functional) = 0.51 uM Anti-HIV-1 activity against mutant HIV-1 in MT-4 cells (mutation selected with ritonavir) ChEMBL. 11543677
ED50 (functional) = 0.51 uM Anti-HIV-1 activity against mutant HIV-1 in MT-4 cells (mutation selected with ritonavir) ChEMBL. 11543677
Ki (binding) = 3.26 nM Inhibitory concentration against HIV-1 protease ChEMBL. 11543677
Ki (binding) = 3.26 nM Inhibitory concentration against HIV-1 protease ChEMBL. 11543677

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

1 literature reference was collected for this gene.

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