Detailed information for compound 228687

Basic information

Technical information
  • TDR Targets ID: 228687
  • Name: 2-[(Z)-(9-fluoro-2,2,4-trimethyl-1H-chromeno[ 3,4-f]quinolin-5-ylidene)methyl]benzonitrile
  • MW: 408.467 | Formula: C27H21FN2O
  • H donors: 1 H acceptors: 1 LogP: 5.89 Rotable bonds: 1
    Rule of 5 violations (Lipinski): 1
  • SMILES: N#Cc1ccccc1/C=C/1\Oc2ccc(cc2c2c1c1C(=CC(Nc1cc2)(C)C)C)F
  • InChi: 1S/C27H21FN2O/c1-16-14-27(2,3)30-22-10-9-20-21-13-19(28)8-11-23(21)31-24(26(20)25(16)22)12-17-6-4-5-7-18(17)15-29/h4-14,30H,1-3H3/b24-12-
  • InChiKey: GPYINFZHNYJFJI-MSXFZWOLSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 2-[(Z)-(9-fluoro-2,2,4-trimethyl-1H-[1]benzopyrano[3,4-f]quinolin-5-ylidene)methyl]benzonitrile
  • 2-[(Z)-(9-fluoro-2,2,4-trimethyl-1H-chromeno[3,4-f]quinolin-5-ylidene)methyl]benzenecarbonitrile

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens progesterone 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
No druggable targets predicted by sequence similarity
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Echinococcus granulosus dihydropyrimidine dehydrogenase NADP 0.1814 0.3884 1
Echinococcus granulosus cadherin EGF LAG seven pass G type receptor 0.0016 0.0000006962 0.0000017924
Loa Loa (eye worm) hypothetical protein 0.0485 0.1013 1
Mycobacterium ulcerans long-chain-fatty-acid--CoA ligase 0.0024 0.0017 0.0013
Schistosoma mansoni hypothetical protein 0.0169 0.033 0.033
Trypanosoma brucei inositol-1(or 4)-monophosphatase 1, putative 0.0036 0.0045 0.0045
Echinococcus granulosus inositol monophosphatase 1 0.0036 0.0045 0.0115
Leishmania major myo-inositol-1(or 4)-monophosphatase 1, putative 0.0036 0.0045 0.0045
Loa Loa (eye worm) hypothetical protein 0.0024 0.0017 0.0168
Mycobacterium ulcerans acyl-CoA synthetase 0.0024 0.0017 0.0013
Trichomonas vaginalis myo inositol monophosphatase, putative 0.0036 0.0045 0.0115
Trichomonas vaginalis cGMP-dependent 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Loa Loa (eye worm) inositol-1 0.0036 0.0045 0.044
Echinococcus multilocularis geminin 0.0169 0.033 0.085
Trichomonas vaginalis dihydroorotate dehydrogenase, putative 0.1814 0.3884 1
Mycobacterium leprae Probable dihydroorotate dehydrogenase PyrD 0.4647 1 1
Brugia malayi latrophilin 2 splice variant baaae 0.0034 0.0039 0.0039
Mycobacterium ulcerans extragenic suppressor protein SuhB 0.0036 0.0045 0.004
Trichomonas vaginalis dihydroorotate dehydrogenase, putative 0.1814 0.3884 1
Toxoplasma gondii hypothetical protein 0.0041 0.0054 0.0054
Trichomonas vaginalis high-affinity cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Schistosoma mansoni cellular tumor antigen P53 0.0049 0.0072 0.0072
Echinococcus granulosus tumor protein p63 0.0336 0.0692 0.1781
Toxoplasma gondii inositol(myo)-1(or 4)-monophosphatase 2, putative 0.0036 0.0045 0.0045
Trypanosoma cruzi myo-inositol-1(or 4)-monophosphatase 1, putative 0.0036 0.0045 0.0045
Loa Loa (eye worm) hypothetical protein 0.0016 0.0000006962 0.0000068758
Plasmodium vivax acyl-CoA synthetase, putative 0.0018 0.0004 0.0004
Brugia malayi Inositol-1 0.0036 0.0045 0.0045
Trichomonas vaginalis cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Trichomonas vaginalis rod cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Trichomonas vaginalis calcium/calmodulin-dependent 3,5-cyclic nucleotide phosphodiesterase, putative 0.0056 0.0088 0.0226
Mycobacterium ulcerans long-chain-fatty-acid-CoA ligase 0.0024 0.0017 0.0013
Mycobacterium ulcerans fatty-acid-CoA ligase 0.0024 0.0017 0.0013
Mycobacterium tuberculosis Probable fatty-acid-CoA ligase FadD2 (fatty-acid-CoA synthetase) (fatty-acid-CoA synthase) 0.0024 0.0017 0.0015
Schistosoma mansoni cgmp-dependent 35-cyclic phosphodiesterase 0.0056 0.0088 0.0088
Entamoeba histolytica myo-inositol monophosphatase, putative 0.0036 0.0045 0.0071
Brugia malayi follicle stimulating hormone receptor 0.0228 0.0458 0.0458
Leishmania major dihydroorotate dehydrogenase 0.4647 1 1
Trypanosoma cruzi dihydroorotate dehydrogenase, putative 0.1814 0.3884 0.3884
Toxoplasma gondii dihydroorotate dehydrogenase reveal, putative 0.4647 1 1
Echinococcus multilocularis tumor protein p63 0.0336 0.0692 0.1781
Schistosoma mansoni hypothetical protein 0.0034 0.0039 0.0039
Loa Loa (eye worm) latrophilin receptor protein 2 0.0016 0.0000006962 0.0000068758
Trichomonas vaginalis calcium/calmodulin-dependent 3,5-cyclic nucleotide phosphodiesterase, putative 0.0056 0.0088 0.0226
Mycobacterium tuberculosis Probable chain -fatty-acid-CoA ligase FadD13 (fatty-acyl-CoA synthetase) 0.0024 0.0017 0.0015
Schistosoma mansoni inositol monophosphatase 0.0036 0.0045 0.0045
Brugia malayi AMP-binding enzyme family protein 0.0024 0.0017 0.0017
Loa Loa (eye worm) hypothetical protein 0.0024 0.0017 0.0168
Echinococcus granulosus cAMP and cAMP inhibited cGMP 3'5' cyclic 0.05 0.1046 0.2694
Trichomonas vaginalis cGMP-dependent 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Trypanosoma cruzi cAMP specific phosphodiesterase, putative 0.0056 0.0088 0.0088
Trypanosoma cruzi cAMP specific phosphodiesterase, putative 0.0056 0.0088 0.0088
Trichomonas vaginalis cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Mycobacterium leprae possible inositol monophosphatase SubH (IMPase) (inositol-1-phosphatase) (I-1-Pase ). 0.0032 0.0036 0.0019
Trichomonas vaginalis dihydroorotate dehydrogenase, putative 0.1814 0.3884 1
Schistosoma mansoni hypothetical protein 0.0016 0.0000006962 0.0000006962
Brugia malayi calcium-independent alpha-latrotoxin receptor 2, putative 0.0016 0.0000006962 0.0000006962
Trichomonas vaginalis high-affinity cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Trichomonas vaginalis high-affinity cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Trypanosoma cruzi dihydroorotate dehydrogenase (fumarate), putative 0.4647 1 1
Echinococcus multilocularis cadherin EGF LAG seven pass G type receptor 0.0016 0.0000006962 0.0000017924
Loa Loa (eye worm) hypothetical protein 0.0024 0.0017 0.0168
Trichomonas vaginalis cyclic nucleotide phosphodiesterase, putative 0.0056 0.0088 0.0226
Schistosoma mansoni hypothetical protein 0.0016 0.0000006962 0.0000006962
Echinococcus granulosus GPCR family 2 0.0016 0.0000006962 0.0000017924
Mycobacterium tuberculosis Two component sensor histidine kinase DosT 0.0041 0.0054 0.0052
Toxoplasma gondii GAF domain-containing protein 0.0041 0.0054 0.0054
Trichomonas vaginalis cGMP-dependent 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Echinococcus multilocularis cAMP and cAMP inhibited cGMP 3',5' cyclic 0.05 0.1046 0.2694
Mycobacterium tuberculosis Probable dihydroorotate dehydrogenase PyrD 0.4647 1 1
Mycobacterium ulcerans two component sensor histidine kinase DevS 0.0041 0.0054 0.005
Giardia lamblia CAMP-specific 3,5-cyclic phosphodiesterase 4B 0.0016 0 0.5
Brugia malayi 3'5'-cyclic nucleotide phosphodiesterase family protein 0.0056 0.0088 0.0088
Brugia malayi Zinc finger, C2H2 type family protein 0.1814 0.3884 0.3884
Echinococcus granulosus diuretic hormone 44 receptor GPRdih2 0.0016 0.0000006962 0.0000017924
Echinococcus granulosus dihydropyrimidine dehydrogenase NADP 0.1814 0.3884 1
Trichomonas vaginalis cone cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Trichomonas vaginalis calcium/calmodulin-dependent 3,5-cyclic nucleotide phosphodiesterase, putative 0.0056 0.0088 0.0226
Mycobacterium ulcerans dihydroorotate dehydrogenase 2 0.4647 1 1
Trichomonas vaginalis conserved hypothetical protein 0.0056 0.0088 0.0226
Brugia malayi Corticotropin releasing factor receptor 2 precursor, putative 0.005 0.0073 0.0073
Mycobacterium ulcerans acyl-CoA synthetase 0.0024 0.0017 0.0013
Plasmodium falciparum dihydroorotate dehydrogenase 0.4647 1 1
Plasmodium falciparum acyl-CoA synthetase 0.0018 0.0004 0.0004
Echinococcus multilocularis diuretic hormone 44 receptor GPRdih2 0.0016 0.0000006962 0.0000017924
Toxoplasma gondii hypothetical protein 0.0041 0.0054 0.0054
Trichomonas vaginalis inositol monophosphatase, putative 0.0036 0.0045 0.0115
Mycobacterium ulcerans putative regulatory protein 0.0041 0.0054 0.005
Loa Loa (eye worm) hypothetical protein 0.0444 0.0925 0.9133
Giardia lamblia Hypothetical protein 0.0016 0 0.5
Mycobacterium tuberculosis Fatty-acid-AMP ligase FadD30 (fatty-acid-AMP synthetase) (fatty-acid-AMP synthase) 0.0018 0.0004 0.0002
Trypanosoma brucei cAMP-specific phosphodiesterase 0.0056 0.0088 0.0088
Trichomonas vaginalis conserved hypothetical protein 0.0041 0.0054 0.0139
Brugia malayi AMP-binding enzyme family protein 0.0024 0.0017 0.0017
Mycobacterium ulcerans long-chain fatty-acid CoA ligase 0.0024 0.0017 0.0013
Toxoplasma gondii hypothetical protein 0.0041 0.0054 0.0054
Trypanosoma cruzi myo-inositol-1(or 4)-monophosphatase 1, putative 0.0036 0.0045 0.0045
Brugia malayi Calcitonin receptor-like protein seb-1 0.005 0.0073 0.0073
Brugia malayi Latrophilin receptor protein 2 0.0016 0.0000006962 0.0000006962
Trichomonas vaginalis rod cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Schistosoma mansoni inositol monophosphatase 0.0036 0.0045 0.0045
Echinococcus multilocularis GPCR, family 2 0.0016 0.0000006962 0.0000017924
Loa Loa (eye worm) follicle stimulating hormone receptor 0.0228 0.0458 0.4519
Trichomonas vaginalis conserved hypothetical protein 0.0041 0.0054 0.0139
Schistosoma mansoni camp/cgmp cyclic nucleotide phosphodiesterase 0.0056 0.0088 0.0088
Mycobacterium tuberculosis Inositol-1-monophosphatase SuhB 0.0032 0.0036 0.0034
Leishmania major 4-coumarate:coa ligase-like protein 0.0024 0.0017 0.0017
Echinococcus granulosus geminin 0.0169 0.033 0.085
Trichomonas vaginalis calcium/calmodulin-dependent 3,5-cyclic nucleotide phosphodiesterase, putative 0.0056 0.0088 0.0226
Echinococcus multilocularis dual 3',5' cyclic AMP and GMP phosphodiesterase 0.0056 0.0088 0.0226
Mycobacterium tuberculosis Two component sensor histidine kinase DevS 0.0041 0.0054 0.0052
Loa Loa (eye worm) pigment dispersing factor receptor c 0.005 0.0073 0.0723
Chlamydia trachomatis acylglycerophosphoethanolamine acyltransferase 0.0018 0.0004 0.5
Trichomonas vaginalis cyclic nucleotide phosphodiesterase, putative 0.0056 0.0088 0.0226
Trichomonas vaginalis cAMP-specific phosphodiesterase, putative 0.0056 0.0088 0.0226
Trichomonas vaginalis conserved hypothetical protein 0.0041 0.0054 0.0139
Trichomonas vaginalis cyclic nucleotide phosphodiesterase, putative 0.0056 0.0088 0.0226
Trichomonas vaginalis calcium/calmodulin-dependent 3,5-cyclic nucleotide phosphodiesterase, putative 0.0056 0.0088 0.0226
Trichomonas vaginalis conserved hypothetical protein 0.0041 0.0054 0.0139
Trypanosoma brucei cAMP-specific phosphodiesterase 0.0056 0.0088 0.0088
Loa Loa (eye worm) hypothetical protein 0.005 0.0073 0.0723
Loa Loa (eye worm) hypothetical protein 0.0049 0.0072 0.0714
Wolbachia endosymbiont of Brugia malayi dihydroorotate dehydrogenase 2 0.4647 1 1
Trichomonas vaginalis rod cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Trypanosoma cruzi dihydroorotate dehydrogenase, putative 0.4647 1 1
Loa Loa (eye worm) hypothetical protein 0.0056 0.0088 0.0867
Loa Loa (eye worm) hypothetical protein 0.0018 0.0004 0.0041
Loa Loa (eye worm) hypothetical protein 0.0034 0.0039 0.0388
Loa Loa (eye worm) hypothetical protein 0.0018 0.0004 0.0041
Brugia malayi Probable 3',5'-cyclic phosphodiesterase C32E12.2, putative 0.05 0.1046 0.1046
Mycobacterium ulcerans putative regulatory protein 0.0041 0.0054 0.005
Trypanosoma brucei dihydroorotate dehydrogenase (fumarate) 0.4647 1 1
Brugia malayi AMP-binding enzyme family protein 0.0024 0.0017 0.0017
Entamoeba histolytica dihydropyrimidine dehydrogenase, putative 0.1814 0.3884 1
Trichomonas vaginalis dihydropyrimidine dehydrogenase, putative 0.1814 0.3884 1
Schistosoma mansoni hypothetical protein 0.0016 0.0000006962 0.0000006962
Echinococcus multilocularis inositol monophosphatase 1 0.0036 0.0045 0.0115
Trichomonas vaginalis cAMP-specific 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Loa Loa (eye worm) hypothetical protein 0.0018 0.0004 0.0041
Trichomonas vaginalis calcium/calmodulin-dependent 3,5-cyclic nucleotide phosphodiesterase, putative 0.0056 0.0088 0.0226
Loa Loa (eye worm) hypothetical protein 0.0018 0.0004 0.0041
Brugia malayi Dihydroorotate dehydrogenase, mitochondrial precursor, putative 0.4647 1 1
Mycobacterium ulcerans hypothetical protein 0.0024 0.0017 0.0013
Plasmodium vivax hypothetical protein, conserved 0.0041 0.0054 0.0054
Echinococcus multilocularis dihydropyrimidine dehydrogenase (NADP+) 0.1814 0.3884 1
Trichomonas vaginalis myo inositol monophosphatase, putative 0.0036 0.0045 0.0115
Echinococcus granulosus dual 3'5' cyclic AMP and GMP phosphodiesterase 0.0056 0.0088 0.0226
Trichomonas vaginalis cAMP-specific phosphodiesterase, putative 0.0056 0.0088 0.0226
Trypanosoma cruzi dihydroorotate dehydrogenase, putative 0.4647 1 1
Trichomonas vaginalis cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Schistosoma mansoni hypothetical protein 0.0169 0.033 0.033
Trichomonas vaginalis high-affinity cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Echinococcus multilocularis dihydropyrimidine dehydrogenase (NADP+) 0.1814 0.3884 1
Plasmodium vivax dihydroorotate dehydrogenase, mitochondrial precursor, putative 0.4647 1 1
Trichomonas vaginalis cone cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Giardia lamblia hypothetical protein 0.0016 0 0.5
Onchocerca volvulus 0.0049 0.0072 1
Trichomonas vaginalis cAMP/cGMP cyclic nucleotide phosphodiesterase, putative 0.0056 0.0088 0.0226
Loa Loa (eye worm) hypothetical protein 0.0018 0.0004 0.0041
Trichomonas vaginalis cAMP-specific 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Schistosoma mansoni dihydroorotate dehydrogenase 0.4647 1 1
Mycobacterium ulcerans acyl-CoA synthetase 0.0024 0.0017 0.0013
Mycobacterium leprae conserved hypothetical protein 0.0041 0.0054 0.0037
Trichomonas vaginalis dihydroorotate dehydrogenase, putative 0.1814 0.3884 1
Leishmania major 4-coumarate:coa ligase-like protein 0.0024 0.0017 0.0017
Trichomonas vaginalis high-affinity cGMP-specific 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Trichomonas vaginalis cGMP-inhibited 3,5-cyclic phosphodiesterase, putative 0.0056 0.0088 0.0226
Leishmania major 4-coumarate:coa ligase-like protein 0.0024 0.0017 0.0017
Trypanosoma cruzi cAMP specific phosphodiesterase, putative 0.0056 0.0088 0.0088
Plasmodium falciparum GAF domain-related protein, putative 0.0041 0.0054 0.0054
Trichomonas vaginalis dihydroorotate dehydrogenase, putative 0.1814 0.3884 1
Schistosoma mansoni hypothetical protein 0.0016 0.0000006962 0.0000006962

Activities

Activity type Activity value Assay description Source Reference
EC50 (functional) = 11 nM Agonistic activity against human progesterone receptor in CV-1 cells ChEMBL. 12954062
EC50 (functional) = 11 nM Agonistic activity against human progesterone receptor in CV-1 cells ChEMBL. 12954062
EC50 (functional) = 97 nM Agonistic activity against human progesterone receptor in T47D breast cancer cells ChEMBL. 12954062
EC50 (functional) = 97 nM Agonistic activity against human progesterone receptor in T47D breast cancer cells ChEMBL. 12954062
Efficacy (functional) = 62 % Percent agonistic effect towards human progesterone receptor in T47D breast cancer cells ChEMBL. 12954062
Efficacy (functional) = 62 % Percent agonistic effect towards human progesterone receptor in T47D breast cancer cells ChEMBL. 12954062
Efficacy (functional) = 78 % Percent agonistic effect towards human progesterone receptor in CV-1 cells ChEMBL. 12954062
Efficacy (functional) = 78 % Percent agonistic effect towards human progesterone receptor in CV-1 cells ChEMBL. 12954062
Ki (binding) = 11.4 nM Binding affinity towards human progesterone receptor A isoform using progesterone as radioligand ChEMBL. 12954062
Ki (binding) = 11.4 nM Binding affinity towards human progesterone receptor A isoform using progesterone as radioligand ChEMBL. 12954062

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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