Detailed information for compound 37861

Basic information

Technical information
  • TDR Targets ID: 37861
  • Name: (+-)-2,4'-Dichloro-alpha-(pyrimidin-5-yl)benz hydryl alcohol
  • MW: 331.196 | Formula: C17H12Cl2N2O
  • H donors: 1 H acceptors: 3 LogP: 3.75 Rotable bonds: 3
    Rule of 5 violations (Lipinski): 1
  • SMILES: Clc1ccc(cc1)C(c1ccccc1Cl)(c1cncnc1)O
  • InChi: 1S/C17H12Cl2N2O/c18-14-7-5-12(6-8-14)17(22,13-9-20-11-21-10-13)15-3-1-2-4-16(15)19/h1-11,22H
  • InChiKey: NHOWDZOIZKMVAI-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (2-chlorophenyl)-(4-chlorophenyl)-pyrimidin-5-ylmethanol
  • (2-chlorophenyl)-(4-chlorophenyl)-pyrimidin-5-yl-methanol
  • (2-chlorophenyl)-(4-chlorophenyl)-(5-pyrimidinyl)methanol
  • (2-chlorophenyl)-(4-chlorophenyl)-(5-pyrimidyl)methanol
  • (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol
  • .alpha.-(2-Chlorophenyl)-.alpha.-(4-chlorophenyl)-5-pyrimidinemethanol
  • 162707-16-6
  • 2,4'-Dichloro-alpha(pyrimidin-5-yl)benzhydryl alcohol
  • 45484_RIEDEL
  • 5-Pyrimidinemethanol, .alpha.-(2-chlorophenyl)-.alpha.-(4-chlorophenyl)-
  • 5-Pyrimidinemethanol, alpha-(2-chlorophenyl)-alpha-(4-chlorophenyl)-
  • 5-Pyrimidinemethanol, alpha-(2-chlorophenyl)-alpha-(4-chlorophenyl)- (9CI)
  • 60168-88-9
  • alpha-(2-Chlorophenyl)-alpha-4-(chlorophenyl)-5-pyrimidinemethanol
  • alpha-(2-Chlorophenyl)-alpha-(4-chlorophenyl)-5-pyrimidinemethanol
  • BLOC
  • BRN 5972869
  • C11226
  • Caswell No. 207AA
  • Compound 56722
  • EINECS 262-095-7
  • EL 222
  • EPA Pesticide Chemical Code 206600
  • fenarimol
  • Fenarimol [ANSI:BSI:ISO]
  • NCGC00163917-02
  • NCGC00163917-01
  • PS1073_SUPELCO
  • Rimidin
  • Rubigan

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens jun proto-oncogene Starlite/ChEMBL No references
Homo sapiens nuclear factor, erythroid 2-like 2 Starlite/ChEMBL No references
Rattus norvegicus Cytochrome P450 19A1 Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Echinococcus granulosus Basic leucine zipper bZIP transcription factor Get druggable targets OG5_131442 All targets in OG5_131442
Echinococcus multilocularis jun protein Get druggable targets OG5_131442 All targets in OG5_131442
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_131442 All targets in OG5_131442
Brugia malayi bZIP transcription factor family protein Get druggable targets OG5_131442 All targets in OG5_131442
Echinococcus granulosus jun protein Get druggable targets OG5_131442 All targets in OG5_131442
Echinococcus multilocularis Basic leucine zipper (bZIP) transcription factor Get druggable targets OG5_131442 All targets in OG5_131442
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Loa Loa (eye worm) cytochrome P450 family protein Cytochrome P450 19A1   508 aa 450 aa 21.1 %
Dictyostelium discoideum cytochrome P450 family protein Cytochrome P450 19A1   508 aa 473 aa 18.8 %
Brugia malayi Cytochrome P450 family protein Cytochrome P450 19A1   508 aa 448 aa 20.8 %
Drosophila melanogaster Cytochrome P450-4d1 Cytochrome P450 19A1   508 aa 464 aa 24.6 %
Dictyostelium discoideum cytochrome P450 family protein Cytochrome P450 19A1   508 aa 465 aa 21.5 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Loa Loa (eye worm) follicle stimulating hormone receptor 0.0254 0.857 1
Schistosoma mansoni hypothetical protein 0.0021 0.0193 0.0315
Plasmodium vivax SET domain protein, putative 0.003 0.0525 0.5
Schistosoma mansoni histone-lysine n-methyltransferase setb1 0.0047 0.1141 0.1864
Echinococcus granulosus fetal alzheimer antigen falz 0.0023 0.0262 0.0327
Echinococcus granulosus 5'partial|histone lysine N methyltransferase SETDB2 0.0029 0.0486 0.0697
Trichomonas vaginalis fructose-bisphosphate aldolase, putative 0.0294 1 1
Echinococcus multilocularis bromodomain adjacent to zinc finger domain 0.006 0.1603 0.2542
Trichomonas vaginalis fructose-bisphosphate aldolase, putative 0.0294 1 1
Schistosoma mansoni histone-lysine n-methyltransferase suv9 0.003 0.0525 0.0858
Schistosoma mansoni histone-lysine n-methyltransferase setb1 0.0047 0.1141 0.1864
Mycobacterium leprae Probable fructose bisphosphate aldolase Fba 0.0144 0.4602 0.5
Mycobacterium tuberculosis Probable fructose-bisphosphate aldolase Fba 0.0144 0.4602 0.5
Echinococcus multilocularis jun protein 0.0101 0.3086 0.4989
Echinococcus multilocularis histone lysine methyltransferase setb histone lysine methyltransferase eggless 0.0047 0.1141 0.1779
Echinococcus granulosus bromodomain adjacent to zinc finger domain 0.0036 0.0745 0.1125
Echinococcus multilocularis zinc finger protein 0.002 0.0154 0.015
Loa Loa (eye worm) PHD-finger family protein 0.0021 0.0193 0.0126
Schistosoma mansoni hypothetical protein 0.0043 0.1006 0.1644
Schistosoma mansoni hypothetical protein 0.0186 0.6122 1
Trichomonas vaginalis fructose-bisphosphate aldolase, putative 0.0294 1 1
Echinococcus granulosus zinc finger protein 0.002 0.0154 0.015
Mycobacterium ulcerans fructose-bisphosphate aldolase 0.0144 0.4602 0.5
Brugia malayi hypothetical protein 0.0043 0.1006 0.0802
Trypanosoma brucei ISWI complex protein 0.0015 0 0.5
Loa Loa (eye worm) hypothetical protein 0.0047 0.1141 0.1244
Trypanosoma cruzi ISWI complex protein 0.0015 0 0.5
Toxoplasma gondii histone lysine methyltransferase SET/SUV39 0.003 0.0525 0.5
Schistosoma mansoni hypothetical protein 0.0082 0.2404 0.3928
Brugia malayi follicle stimulating hormone receptor 0.0254 0.857 1
Schistosoma mansoni histone-lysine n-methyltransferase setb1 0.003 0.0525 0.0858
Brugia malayi Bromodomain containing protein 0.0075 0.2155 0.2199
Brugia malayi hypothetical protein 0.008 0.2305 0.2381
Schistosoma mansoni zinc finger protein 0.002 0.0154 0.0252
Onchocerca volvulus 0.0238 0.8 1
Echinococcus granulosus jun protein 0.0101 0.3086 0.4989
Loa Loa (eye worm) hypothetical protein 0.0041 0.0918 0.0982
Entamoeba histolytica fructose-1,6-bisphosphate aldolase, putative 0.0294 1 1
Brugia malayi Pre-SET motif family protein 0.0209 0.6962 0.8044
Loa Loa (eye worm) hypothetical protein 0.0099 0.2986 0.3419
Loa Loa (eye worm) pre-SET domain-containing protein family protein 0.0209 0.6962 0.8104
Schistosoma mansoni acetyl-CoA C-acetyltransferase 0.0023 0.0262 0.0427
Trichomonas vaginalis fructose-bisphosphate aldolase, putative 0.0294 1 1
Echinococcus multilocularis histone lysine N methyltransferase SETMAR 0.003 0.0525 0.0763
Giardia lamblia Fructose-bisphosphate aldolase 0.0294 1 0.5
Trichomonas vaginalis fructose-bisphosphate aldolase, putative 0.0294 1 1
Trypanosoma cruzi ISWI complex protein 0.0015 0 0.5
Schistosoma mansoni jun-related protein 0.0082 0.2404 0.3928
Brugia malayi Pre-SET motif family protein 0.003 0.0525 0.0217
Schistosoma mansoni methyl-cpg binding protein mbd 0.0017 0.0063 0.0103
Echinococcus multilocularis Basic leucine zipper (bZIP) transcription 0.0043 0.1006 0.1557
Trichomonas vaginalis fructose-bisphosphate aldolase, putative 0.0294 1 1
Echinococcus granulosus Basic leucine zipper bZIP transcription factor 0.0101 0.3086 0.4989
Loa Loa (eye worm) hypothetical protein 0.0071 0.2001 0.2258
Schistosoma mansoni bromodomain containing protein 0.0064 0.1732 0.283
Loa Loa (eye worm) hypothetical protein 0.0043 0.0987 0.1063
Trichomonas vaginalis fructose-bisphosphate aldolase, putative 0.0294 1 1
Echinococcus multilocularis fetal alzheimer antigen, falz 0.0023 0.0262 0.0327
Echinococcus granulosus bromodomain adjacent to zinc finger domain 0.006 0.1603 0.2542
Brugia malayi bZIP transcription factor family protein 0.0101 0.3086 0.3331
Treponema pallidum fructose-bisphosphate aldolase 0.0294 1 0.5
Echinococcus multilocularis geminin 0.0186 0.6122 1
Echinococcus granulosus histone lysine methyltransferase setb 0.0047 0.1141 0.1779
Leishmania major hypothetical protein, conserved 0.0015 0 0.5
Echinococcus granulosus geminin 0.0186 0.6122 1
Schistosoma mansoni transcription factor LCR-F1 0.0043 0.1006 0.1644
Onchocerca volvulus 0.008 0.2305 0.238
Schistosoma mansoni methyl-cpg binding protein mbd 0.0017 0.0063 0.0103
Echinococcus multilocularis bromodomain adjacent to zinc finger domain 0.0036 0.0745 0.1125
Echinococcus granulosus Basic leucine zipper bZIP transcription 0.0043 0.1006 0.1557
Echinococcus multilocularis Basic leucine zipper (bZIP) transcription factor 0.0101 0.3086 0.4989
Trichomonas vaginalis fructose-bisphosphate aldolase, putative 0.0294 1 1
Schistosoma mansoni hypothetical protein 0.0186 0.6122 1
Brugia malayi Bromodomain containing protein 0.0039 0.083 0.0588
Loa Loa (eye worm) hypothetical protein 0.0039 0.0833 0.0881

Activities

Activity type Activity value Assay description Source Reference
Activity (functional) = 80 % Antitrypanosomal activity against trypomastigotes of Trypanosoma cruzi Tulahuen infected in Swiss mouse model of chagas disease assessed as decrease in parasite level in blood at 100 mg/kg, ip administered 8 days after post infection qd for 5 days ChEMBL. 22536986
Cp (ADMET) = 2.1 uM Plasma concentration in Swiss mouse at 20 mg/kg, po after 1 hr ChEMBL. 22536986
EC50 (binding) = 4.1 uM In vitro inhibition of cytochrome P450 19A1 by rat ovarian microsomes incubated with [3H]-androstenedione and NADPH-generating system. ChEMBL. 3612685
EC50 (binding) = 4.1 uM In vitro inhibition of cytochrome P450 19A1 by rat ovarian microsomes incubated with [3H]-androstenedione and NADPH-generating system. ChEMBL. 3612685
IC50 (functional) = 0.25 uM DNDI: Inhibition of Chagas Disease parasite Trypanosoma cruzi (Tulahuen LacZ, Clone C4), in vitro. ChEMBL. No reference
IC50 (functional) = 0.35 uM DNDI: Inhibition of Chagas Disease parasite Trypanosoma cruzi (Tulahuen LacZ, Clone C4), in vitro. ChEMBL. No reference
IC50 (functional) = 0.35 uM Antitrypanosomal activity against trypomastigotes of Trypanosoma cruzi Tulahuen expressing the beta- galactosidase gene infected rat L6 cells after 96 hrs ChEMBL. 22536986
IC90 (functional) = DNDI: Inhibition of Chagas Disease parasite Trypanosoma cruzi (Tulahuen LacZ, Clone C4), in vitro. ChEMBL. No reference
IC90 (functional) = 0.56 uM DNDI: Inhibition of Chagas Disease parasite Trypanosoma cruzi (Tulahuen LacZ, Clone C4), in vitro. ChEMBL. No reference
Inhibition (ADMET) = 66 % Inhibition of CYP3A4/6 in human liver microsomes at 20 uM ChEMBL. 22536986
Potency (functional) 6.1131 uM PubChem BioAssay: Tox21. qHTS assay for small molecule agonists of the antioxidant response element (ARE) signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 12.5153 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule agonists of the AP-1 signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 24.5412 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule antagonists of the androgen receptor (AR) signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 28.1838 uM PUBCHEM_BIOASSAY: qHTS assay for small molecule agonists of retinoid X receptor alpha signaling. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 34.9714 uM PubChem BioAssay: Tox21. qHTS assay for small molecule agonists of the antioxidant response element (ARE) signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 39.8107 uM PUBCHEM_BIOASSAY: qHTS assay for small molecule antagonists of farnesoid X receptor signaling. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 44.6684 uM PUBCHEM_BIOASSAY: qHTS assay for small molecule agonists of peroxisome proliferator-activated receptor gamma signaling. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 44.6684 uM PubChem BioAssay. qHTS assay for small molecule activators of the rat pregnane X receptor (rPXR) signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 48.9662 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule agonists of the NFkB signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 49.8242 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule antagonists of the androgen receptor (AR) signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 50.1187 uM PUBCHEM_BIOASSAY: qHTS assay for small molecule antagonists of vitamin D receptor signaling. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 54.941 uM PubChem BioAssay: Tox21. qHTS assay for small molecule activators of the heat shock response signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 68.5896 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule antagonists of the androgen receptor (AR) signaling pathway using the MDA cell line. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 69.7771 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule antagonists of the androgen receptor (AR) signaling pathway using the MDA cell line. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 89.1251 uM PUBCHEM_BIOASSAY: Inhibitors of the vitamin D receptor (VDR): qHTS. (Class of assay: confirmatory) [Related pubchem assays (depositor defined):AID504855] ChEMBL. No reference

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Trypanosoma cruzi ChEMBL23 22536986

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.

If you have references for this compound, please enter them in a user comment (below) or Contact us.