Detailed information for compound 44688

Basic information

Technical information
  • TDR Targets ID: 44688
  • Name: 2-[2,6-dibromo-4-[2-[[(1R,2S)-1-hydroxy-1-(4- hydroxyphenyl)propan-2-yl]amino]ethyl]anilino ]acetic acid
  • MW: 502.197 | Formula: C19H22Br2N2O4
  • H donors: 5 H acceptors: 4 LogP: 1.36 Rotable bonds: 9
    Rule of 5 violations (Lipinski): 2
  • SMILES: OC(=O)CNc1c(Br)cc(cc1Br)CCN[C@H]([C@@H](c1ccc(cc1)O)O)C
  • InChi: 1S/C19H22Br2N2O4/c1-11(19(27)13-2-4-14(24)5-3-13)22-7-6-12-8-15(20)18(16(21)9-12)23-10-17(25)26/h2-5,8-9,11,19,22-24,27H,6-7,10H2,1H3,(H,25,26)/t11-,19-/m0/s1
  • InChiKey: MBSXHCBRJMLUOW-WLRWDXFRSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 2-[2,6-dibromo-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methyl-ethyl]amino]ethyl]anilino]acetic acid
  • 2-[2,6-dibromo-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]anilino]acetic acid
  • 2-[[2,6-dibromo-4-[2-[[(1R,2S)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenyl]amino]ethanoic acid
  • 2-[[2,6-dibromo-4-[2-[[(1R,2S)-1-hydroxy-1-(4-hydroxyphenyl)propan-2-yl]amino]ethyl]phenyl]amino]acetic acid
  • 2-[[2,6-dibromo-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methyl-ethyl]amino]ethyl]phenyl]amino]acetic acid
  • 2-[[2,6-dibromo-4-[2-[[(1S,2R)-2-hydroxy-2-(4-hydroxyphenyl)-1-methylethyl]amino]ethyl]phenyl]amino]acetic acid

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Rattus norvegicus Beta-3 adrenergic receptor Starlite/ChEMBL References
Rattus norvegicus Beta-2 adrenergic receptor Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
No druggable targets predicted by orthology data
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Echinococcus granulosus rhodopsin orphan GPCR Beta-2 adrenergic receptor   418 aa 344 aa 20.6 %
Brugia malayi follicle stimulating hormone receptor Beta-2 adrenergic receptor   418 aa 364 aa 22.3 %
Onchocerca volvulus Beta-2 adrenergic receptor   418 aa 346 aa 19.9 %
Schistosoma japonicum ko:K04209 neuropeptide Y receptor, invertebrate, putative Beta-3 adrenergic receptor   400 aa 324 aa 22.2 %
Echinococcus multilocularis orexin receptor type 2 Beta-3 adrenergic receptor   400 aa 321 aa 22.7 %
Onchocerca volvulus Phospholipase d-related homolog Beta-2 adrenergic receptor   418 aa 392 aa 23.5 %
Onchocerca volvulus Mitochondrial inner membrane protein homolog Beta-3 adrenergic receptor   400 aa 328 aa 34.8 %
Loa Loa (eye worm) hypothetical protein Beta-2 adrenergic receptor   418 aa 401 aa 24.2 %
Schistosoma japonicum ko:K04135 adrenergic receptor, alpha 1a, putative Beta-3 adrenergic receptor   400 aa 343 aa 34.7 %
Echinococcus multilocularis thyrotropin releasing hormone receptor Beta-3 adrenergic receptor   400 aa 334 aa 24.6 %
Schistosoma mansoni biogenic amine (5HT) receptor Beta-3 adrenergic receptor   400 aa 385 aa 33.0 %
Schistosoma japonicum ko:K04136 adrenergic receptor, alpha 1b, putative Beta-2 adrenergic receptor   418 aa 396 aa 32.6 %
Onchocerca volvulus Beta-3 adrenergic receptor   400 aa 336 aa 20.5 %
Onchocerca volvulus Mitogen-activated protein kinase kinase kinase 8 homolog Beta-2 adrenergic receptor   418 aa 430 aa 22.3 %
Echinococcus granulosus orexin receptor type 2 Beta-3 adrenergic receptor   400 aa 321 aa 22.7 %
Echinococcus granulosus thyrotropin releasing hormone receptor Beta-3 adrenergic receptor   400 aa 338 aa 24.6 %
Onchocerca volvulus Beta-2 adrenergic receptor   418 aa 352 aa 28.1 %
Echinococcus multilocularis rhodopsin orphan GPCR Beta-2 adrenergic receptor   418 aa 397 aa 19.6 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Toxoplasma gondii thioredoxin reductase 0.0049 0.061 0.3591
Giardia lamblia NADH oxidase lateral transfer candidate 0.0017 0.0035 0.5
Schistosoma mansoni dihydrolipoamide dehydrogenase 0.0017 0.0035 0.0138
Schistosoma mansoni aldehyde dehydrogenase 0.0063 0.086 0.3391
Schistosoma mansoni alpha-galactosidase/alpha-n-acetylgalactosaminidase 0.007 0.1001 0.3948
Schistosoma mansoni alpha-galactosidase/alpha-n-acetylgalactosaminidase 0.007 0.1001 0.3948
Echinococcus multilocularis histone lysine methyltransferase setb histone lysine methyltransferase eggless 0.0031 0.0286 0.1746
Mycobacterium leprae DIHYDROLIPOAMIDE DEHYDROGENASE LPD (LIPOAMIDE REDUCTASE (NADH)) (LIPOYL DEHYDROGENASE) (DIHYDROLIPOYL DEHYDROGENASE) (DIAPHORASE 0.0124 0.1961 1
Mycobacterium tuberculosis Probable dehydrogenase 0.0111 0.1737 0.8837
Echinococcus multilocularis Alpha N acetylgalactosaminidase 0.0106 0.1636 1
Toxoplasma gondii histone lysine methyltransferase SET/SUV39 0.0031 0.0286 0.1565
Chlamydia trachomatis dihydrolipoyl dehydrogenase 0.0017 0.0035 0.5
Trichomonas vaginalis alpha-galactosidase/alpha-N-acetylgalactosaminidase, putative 0.007 0.1001 0.2355
Echinococcus multilocularis thioredoxin glutathione reductase 0.0049 0.061 0.3729
Schistosoma mansoni aldehyde dehydrogenase 0.0063 0.086 0.3391
Schistosoma mansoni histone-lysine n-methyltransferase suv9 0.0031 0.0286 0.1126
Schistosoma mansoni histone-lysine n-methyltransferase setb1 0.0031 0.0286 0.1126
Mycobacterium tuberculosis NAD(P)H quinone reductase LpdA 0.0124 0.1961 1
Plasmodium vivax SET domain protein, putative 0.0031 0.0286 0.4358
Onchocerca volvulus 0.0244 0.4139 1
Schistosoma mansoni alpha-galactosidase/alpha-n-acetylgalactosaminidase 0.0106 0.1636 0.6451
Schistosoma mansoni alpha-galactosidase/alpha-n-acetylgalactosaminidase 0.0106 0.1636 0.6451
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0017 0.0035 0.5
Mycobacterium ulcerans aldehyde dehydrogenase 0.0063 0.086 1
Toxoplasma gondii melibiase subfamily protein 0.0106 0.1636 1
Mycobacterium ulcerans aldehyde dehydrogenase 0.0063 0.086 1
Brugia malayi Pre-SET motif family protein 0.0031 0.0286 0.0251
Plasmodium vivax glutathione reductase, putative 0.0049 0.061 1
Mycobacterium ulcerans aldehyde dehydrogenase 0.0063 0.086 1
Loa Loa (eye worm) hypothetical protein 0.0569 1 1
Echinococcus granulosus thioredoxin glutathione reductase 0.0049 0.061 0.3729
Plasmodium falciparum glutathione reductase 0.0049 0.061 1
Mycobacterium tuberculosis Probable reductase 0.0111 0.1737 0.8837
Loa Loa (eye worm) glutathione reductase 0.0049 0.061 0.061
Schistosoma mansoni histone-lysine n-methyltransferase setb1 0.0031 0.0286 0.1126
Schistosoma mansoni alpha-galactosidase/alpha-n-acetylgalactosaminidase 0.0106 0.1636 0.6451
Mycobacterium tuberculosis Dihydrolipoamide dehydrogenase LpdC (lipoamide reductase (NADH)) (lipoyl dehydrogenase) (dihydrolipoyl dehydrogenase) (diaphoras 0.0124 0.1961 1
Echinococcus multilocularis histone lysine N methyltransferase SETMAR 0.0031 0.0286 0.1746
Mycobacterium tuberculosis Putative ferredoxin reductase 0.0111 0.1737 0.8837
Echinococcus multilocularis nuclear factor of activated T cells 5 0.0076 0.11 0.6726
Mycobacterium tuberculosis Probable oxidoreductase 0.0124 0.1961 1
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0017 0.0035 0.5
Brugia malayi Thioredoxin reductase 0.0049 0.061 0.0577
Mycobacterium tuberculosis Probable aldehyde dehydrogenase 0.0063 0.086 0.4283
Echinococcus granulosus dihydrolipoamide dehydrogenase 0.0017 0.0035 0.0215
Schistosoma mansoni alpha-galactosidase/alpha-n-acetylgalactosaminidase 0.0106 0.1636 0.6451
Trypanosoma brucei trypanothione reductase 0.0049 0.061 1
Echinococcus granulosus 5'partial|histone lysine N methyltransferase SETDB2 0.003 0.0265 0.1621
Loa Loa (eye worm) thioredoxin reductase 0.0049 0.061 0.061
Loa Loa (eye worm) hypothetical protein 0.007 0.1001 0.1001
Plasmodium vivax thioredoxin reductase, putative 0.0049 0.061 1
Echinococcus multilocularis Glycoside hydrolase, family 27 0.0106 0.1636 1
Brugia malayi Pre-SET motif family protein 0.0215 0.3602 0.3579
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr 0.0049 0.061 0.2985
Mycobacterium tuberculosis Probable nitrite reductase [NAD(P)H] large subunit [FAD flavoprotein] NirB 0.0111 0.1737 0.8837
Echinococcus granulosus nuclear factor of activated T cells 5 0.0076 0.11 0.6726
Mycobacterium tuberculosis Probable membrane NADH dehydrogenase NdhA 0.0111 0.1737 0.8837
Plasmodium falciparum thioredoxin reductase 0.0049 0.061 1
Mycobacterium tuberculosis Probable NADH dehydrogenase Ndh 0.0111 0.1737 0.8837
Brugia malayi hypothetical protein 0.0125 0.1995 0.1966
Treponema pallidum NADH oxidase 0.0017 0.0035 0.5
Loa Loa (eye worm) hypothetical protein 0.0031 0.0286 0.0286
Loa Loa (eye worm) hypothetical protein 0.0327 0.5632 0.5632
Leishmania major trypanothione reductase 0.0049 0.061 0.697
Loa Loa (eye worm) pre-SET domain-containing protein family protein 0.0215 0.3602 0.3602
Loa Loa (eye worm) hypothetical protein 0.0569 1 1
Echinococcus granulosus aldehyde dehydrogenase mitochondrial 0.0063 0.086 0.5257
Echinococcus multilocularis dihydrolipoamide dehydrogenase 0.0017 0.0035 0.0215
Loa Loa (eye worm) NNMT/PNMT/TEMT family protein 0.0569 1 1
Echinococcus granulosus Alpha N acetylgalactosaminidase 0.0106 0.1636 1
Leishmania major aldehyde dehydrogenase, mitochondrial precursor 0.0063 0.086 1
Brugia malayi Melibiase family protein 0.007 0.1001 0.0969
Trypanosoma cruzi trypanothione reductase, putative 0.0049 0.061 1
Echinococcus granulosus histone lysine methyltransferase setb 0.0031 0.0286 0.1746
Schistosoma mansoni histone-lysine n-methyltransferase setb1 0.0031 0.0286 0.1126
Echinococcus multilocularis aldehyde dehydrogenase, mitochondrial 0.0063 0.086 0.5257
Toxoplasma gondii aldehyde dehydrogenase 0.0063 0.086 0.5153
Trichomonas vaginalis set domain proteins, putative 0.0244 0.4137 1
Brugia malayi glutathione reductase 0.0049 0.061 0.0577

Activities

Activity type Activity value Assay description Source Reference
-Log EC20 (functional) = 4.72 Increase in BPM in isolated rat atria. ChEMBL. 11311067
-Log EC20 (functional) = 4.72 Increase in BPM in isolated rat atria. ChEMBL. 11311067
-Log EC50 (functional) = 7.09 Agonistic activity towards beta-3 adrenoceptor. Mean concentration required to produce 50% relaxation of detrusor before the addition of the compound in the ferret detrusor ChEMBL. 11311067
-Log IC50 (functional) = 5.59 Agonistic activity towards beta-2 adrenoceptor. Mean concentration required to produce 50% inhibition of uterine contraction ChEMBL. 11311067
EC50 (functional) = 7.09 Agonistic activity towards beta-3 adrenoceptor. Mean concentration required to produce 50% relaxation of detrusor before the addition of the compound in the ferret detrusor ChEMBL. 11311067
IC50 (functional) = 5.59 Agonistic activity towards beta-2 adrenoceptor. Mean concentration required to produce 50% inhibition of uterine contraction ChEMBL. 11311067
Intrinsic activity (functional) = 0.83 Activity compared to that observed following forskolin (10e -5). ChEMBL. 11311067
Intrinsic activity (functional) = 0.83 Activity compared to that observed following forskolin (10e -5). ChEMBL. 11311067
Selectivity (functional) = 32 Concentration ratio of beta2 (EC50) to beta3 (EC50) ChEMBL. 11311067
Selectivity (functional) = 235 Concentration ratio of beta1 (EC50) to beta3 (EC50) ChEMBL. 11311067

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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