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  


Substructure search Similarity search

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
Trypanosoma brucei variant surface glycoprotein (VSG), putative Human immunodeficiency virus type 1 protease   99 aa 80 aa 27.5 %
Candida albicans dethiobiotin synthetase Human immunodeficiency virus type 1 protease   99 aa 90 aa 22.2 %
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 %
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 %
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
Plasmodium falciparum 3-oxoacyl-acyl-carrier protein synthase I/II 0.0243 0 0.5
Mycobacterium ulcerans Type I modular polyketide synthase 0.0968 0.4555 0.6023
Loa Loa (eye worm) hypothetical protein 0.1625 0.869 1
Mycobacterium ulcerans phenolpthiocerol synthesis type-I polyketide synthase PpsE 0.064 0.2495 0.3299
Mycobacterium ulcerans polyketide synthase Pks13 0.1446 0.7562 1
Schistosoma mansoni intracisternal A-particle retropepsin (A02 family) 0.1528 0.8076 1
Echinococcus granulosus calcium:calmodulin dependent 3'5' cyclic 0.0482 0.1504 0.2107
Mycobacterium tuberculosis Probable polyketide synthase Pks8 0.0791 0.3447 0.4329
Mycobacterium tuberculosis Probable polyketide synthase Pks15 0.0391 0.0933 0.0864
Toxoplasma gondii type I fatty acid synthase, putative 0.1028 0.4933 1
Mycobacterium tuberculosis Probable polyketide synthase Pks5 0.0938 0.4368 0.5599
Plasmodium vivax 3',5'-cyclic nucleotide phosphodiesterase, putative 0.0482 0.1504 1
Mycobacterium tuberculosis Probable multifunctional mycocerosic acid synthase membrane-associated Mas 0.1028 0.4933 0.6376
Mycobacterium tuberculosis Phenolpthiocerol synthesis type-I polyketide synthase PpsD 0.0968 0.4555 0.5856
Leishmania major cAMP phosphodiesterase A, putative;with=GeneDB:LinJ18_V3.1100 0.0482 0.1504 1
Mycobacterium tuberculosis Polyketide synthetase MbtD (polyketide synthase) 0.0297 0.0343 0.0052
Mycobacterium leprae PROBABLE THIOESTERASE TESA 0.0806 0.3541 0.4398
Trypanosoma cruzi cAMP phosphodiesterase A, putative 0.0482 0.1504 1
Loa Loa (eye worm) AMP-binding enzyme family protein 0.0904 0.4155 0.4782
Leishmania major hypothetical protein, conserved 0.0291 0.0306 0.2032
Mycobacterium tuberculosis Polyketide synthetase MbtC (polyketide synthase) 0.0333 0.0564 0.0356
Loa Loa (eye worm) acyl carrier protein 0.0445 0.127 0.1462
Onchocerca volvulus 0.1684 0.9058 0.9285
Toxoplasma gondii AMP-binding enzyme domain-containing protein 0.0489 0.1547 0.3136
Mycobacterium ulcerans polyketide synthase 0.1028 0.4933 0.6522
Mycobacterium ulcerans phenolpthiocerol synthesis type-I polyketide synthase PpsD 0.0968 0.4555 0.6023
Loa Loa (eye worm) hypothetical protein 0.0542 0.1881 0.2164
Brugia malayi Methyltransferase-like protein 4 0.0291 0.0306 0.0306
Brugia malayi Probable 3',5'-cyclic phosphodiesterase T04D3.3, putative 0.1378 0.7135 0.7135
Echinococcus multilocularis calcium:calmodulin dependent 3',5' cyclic 0.1378 0.7135 1
Mycobacterium ulcerans polyketide synthase MbtD 0.0297 0.0343 0.0454
Mycobacterium tuberculosis Probable polyketide synthase Pks9 0.055 0.1931 0.224
Mycobacterium leprae Probable polyketide synthase Pks1 0.1028 0.4933 0.6337
Mycobacterium leprae Polyketide synthase Pks13 0.1446 0.7562 1
Mycobacterium ulcerans Type I modular polyketide synthase 0.0968 0.4555 0.6023
Mycobacterium tuberculosis Probable membrane bound polyketide synthase Pks6 0.1446 0.7562 1
Mycobacterium tuberculosis Phenyloxazoline synthase MbtB (phenyloxazoline synthetase) 0.0904 0.4155 0.5305
Mycobacterium tuberculosis Polyketide synthase Pks2 0.0938 0.4368 0.5599
Mycobacterium ulcerans thioesterase 0.0806 0.3541 0.4682
Trypanosoma brucei cAMP phosphodiesterase A, putative 0.0482 0.1504 1
Brugia malayi AMP-binding enzyme family protein 0.0904 0.4155 0.4155
Trichomonas vaginalis conserved hypothetical protein 0.0291 0.0306 0.5
Mycobacterium ulcerans thioesterase TesA 0.0806 0.3541 0.4682
Mycobacterium tuberculosis Probable polyketide synthase Pks7 0.1028 0.4933 0.6376
Echinococcus multilocularis calcium:calmodulin dependent 3',5' cyclic 0.0482 0.1504 0.2107
Brugia malayi Beta-ketoacyl synthase, N-terminal domain containing protein 0.0968 0.4555 0.4555
Mycobacterium leprae PHENOLPTHIOCEROL SYNTHESIS TYPE-I POLYKETIDE SYNTHASE PPSC 0.1028 0.4933 0.6337
Toxoplasma gondii type I fatty acid synthase, putative 0.0689 0.2802 0.5682
Echinococcus granulosus calcium:calmodulin dependent 3'5' cyclic 0.1378 0.7135 1
Mycobacterium ulcerans polyketide synthase 0.0968 0.4555 0.6023
Mycobacterium ulcerans Type I modular polyketide synthase 0.0968 0.4555 0.6023
Schistosoma mansoni family A2 unassigned peptidase (A02 family) 0.0278 0.0219 0.0272
Schistosoma mansoni calcium/calmodulin-dependent 35-cyclic nucleotide phosphodiesterase 0.1378 0.7135 0.8835
Trypanosoma cruzi cAMP phosphodiesterase A, putative 0.0482 0.1504 1
Loa Loa (eye worm) PDE1B protein 0.1378 0.7135 0.8211
Mycobacterium ulcerans polyketide synthase Pks9 0.064 0.2495 0.3299
Mycobacterium tuberculosis Polyketide synthase Pks12 0.1028 0.4933 0.6376
Mycobacterium tuberculosis Probable fatty acid synthase Fas (fatty acid synthetase) 0.0304 0.0384 0.0108
Mycobacterium leprae PHENOLPTHIOCEROL SYNTHESIS TYPE-I POLYKETIDE SYNTHASE PPSA 0.0968 0.4555 0.581
Mycobacterium tuberculosis Phenolpthiocerol synthesis type-I polyketide synthase PpsC 0.0968 0.4555 0.5856
Mycobacterium ulcerans multifunctional mycocerosic acid synthase membrane-associated Mas 0.1028 0.4933 0.6522
Mycobacterium leprae PHENOLPTHIOCEROL SYNTHESIS TYPE-I POLYKETIDE SYNTHASE PPSB 0.0779 0.3367 0.4155
Mycobacterium tuberculosis Phenolpthiocerol synthesis type-I polyketide synthase PpsA 0.0968 0.4555 0.5856
Chlamydia trachomatis 3-oxoacyl-ACP synthase 0.0243 0 0.5
Giardia lamblia Methyltransferase like 2 0.0291 0.0306 0.5
Mycobacterium leprae PHENOLPTHIOCEROL SYNTHESIS TYPE-I POLYKETIDE SYNTHASE PPSD 0.0968 0.4555 0.581
Mycobacterium ulcerans phenolpthiocerol synthesis type-I polyketide synthase PpsC 0.1028 0.4933 0.6522
Toxoplasma gondii 3'5'-cyclic nucleotide phosphodiesterase domain-containing protein 0.0482 0.1504 0.3048
Mycobacterium tuberculosis Probable thioesterase TesA 0.0806 0.3541 0.4459
Schistosoma mansoni methyltransferase-related 0.0291 0.0306 0.0378
Mycobacterium tuberculosis Polyketide synthase Pks13 0.1446 0.7562 1
Mycobacterium ulcerans phenolpthiocerol synthesis type-I polyketide synthase PpsB 0.0779 0.3367 0.4452
Loa Loa (eye worm) fatty acid synthase 0.0955 0.4474 0.5149
Mycobacterium leprae Probable multifunctional mycocerosic acid synthase membrane associated enzyme Mas 0.1028 0.4933 0.6337
Mycobacterium tuberculosis Probable polyketide synthase Pks1 0.0695 0.2842 0.3495
Mycobacterium ulcerans phenolpthiocerol synthesis type-I polyketide synthase PpsA 0.0779 0.3367 0.4452
Toxoplasma gondii 3'5'-cyclic nucleotide phosphodiesterase domain-containing protein 0.0482 0.1504 0.3048
Toxoplasma gondii beta-ketoacyl synthase, N-terminal domain-containing protein 0.0628 0.2419 0.4903
Wolbachia endosymbiont of Brugia malayi 3-oxoacyl-ACP synthase 0.0243 0 0.5
Mycobacterium leprae PHENOLPTHIOCEROL SYNTHESIS TYPE-I POLYKETIDE SYNTHASE PPSE 0.064 0.2495 0.2941
Brugia malayi AMP-binding enzyme family protein 0.0297 0.0343 0.0343
Mycobacterium ulcerans fatty acid synthase Fas 0.0304 0.0384 0.0508
Onchocerca volvulus Fatty acid synthase homolog 0.1744 0.9436 1

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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