Detailed information for compound 966734

Basic information

Technical information
  • TDR Targets ID: 966734
  • Name: 2169-44-0
  • MW: 341.401 | Formula: C20H23NO4
  • H donors: 1 H acceptors: 1 LogP: 3.05 Rotable bonds: 3
    Rule of 5 violations (Lipinski): 1
  • SMILES: COc1c(OC)cc2c3c1c1cc(OC)c(cc1C[C@@H]3N(CC2)C)O
  • InChi: 1S/C20H23NO4/c1-21-6-5-11-9-17(24-3)20(25-4)19-13-10-16(23-2)15(22)8-12(13)7-14(21)18(11)19/h8-10,14,22H,5-7H2,1-4H3/t14-/m0/s1
  • InChiKey: ZFLRVRLYWHNAEC-AWEZNQCLSA-N  


Substructure search Similarity search

Network

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Synonyms

  • NSC247564
  • 1,2,10-Trimethoxy-6a-alpha-aporphin-9-ol
  • 4H-Dibenzo(de,g)quinolin-9-ol, 5,6,6a,7-tetrahydro-1,2,10-trimethoxy-6-methyl-, (S)-
  • 6a-alpha-APORPHIN-9-OL, 1,2,10-TRIMETHOXY-
  • Lauroscholtzine
  • NSC 247506
  • NSC 247564
  • Rogersine
  • N-Methyllaurotetanine
  • NSC247506

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens dopamine receptor D3 Starlite/ChEMBL References
Homo sapiens solute carrier family 6 (neurotransmitter transporter), member 3 Starlite/ChEMBL References
Homo sapiens 5-hydroxytryptamine (serotonin) receptor 6, G protein-coupled Starlite/ChEMBL References
Homo sapiens 5-hydroxytryptamine (serotonin) receptor 2B, G protein-coupled Starlite/ChEMBL References
Homo sapiens solute carrier family 6 (neurotransmitter transporter), member 2 Starlite/ChEMBL References
Homo sapiens 5-hydroxytryptamine (serotonin) receptor 5A, G protein-coupled Starlite/ChEMBL References
Homo sapiens adrenoceptor alpha 2C Starlite/ChEMBL References
Homo sapiens 5-hydroxytryptamine (serotonin) receptor 7, adenylate cyclase-coupled Starlite/ChEMBL References
Homo sapiens solute carrier family 6 (neurotransmitter transporter), member 4 Starlite/ChEMBL References
Homo sapiens adrenoceptor beta 2, surface Starlite/ChEMBL References
Homo sapiens 5-hydroxytryptamine (serotonin) receptor 1A, G protein-coupled Starlite/ChEMBL References
Homo sapiens dopamine receptor D1 Starlite/ChEMBL References
Homo sapiens adrenoceptor alpha 1B Starlite/ChEMBL References
Homo sapiens 5-hydroxytryptamine (serotonin) receptor 2C, G protein-coupled Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Brugia malayi Sodium:neurotransmitter symporter family protein Get druggable targets OG5_128364 All targets in OG5_128364
Echinococcus granulosus serotonin transporter Get druggable targets OG5_128364 All targets in OG5_128364
Schistosoma japonicum ko:K04153 5-hydroxytryptamine (serotonin) receptor 1A, putative Get druggable targets OG5_133249 All targets in OG5_133249
Echinococcus granulosus biogenic amine 5HT receptor Get druggable targets OG5_133249 All targets in OG5_133249
Schistosoma japonicum 5-hydroxytryptamine receptor 1, putative Get druggable targets OG5_132667 All targets in OG5_132667
Echinococcus granulosus tm gpcr rhodopsin Get druggable targets OG5_145685 All targets in OG5_145685
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_128364 All targets in OG5_128364
Schistosoma japonicum ko:K05336 solute carrier family 6 (neurotransmitter transporter), invertebrate, putative Get druggable targets OG5_128364 All targets in OG5_128364
Brugia malayi Serotonin receptor Get druggable targets OG5_135430 All targets in OG5_135430
Echinococcus multilocularis serotonin transporter Get druggable targets OG5_128364 All targets in OG5_128364
Echinococcus multilocularis serotonin receptor Get druggable targets OG5_133249 All targets in OG5_133249
Schistosoma japonicum Sodium-dependent noradrenaline transporter, putative Get druggable targets OG5_128364 All targets in OG5_128364
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_128364 All targets in OG5_128364
Echinococcus multilocularis tm gpcr rhodopsin gpcr rhodopsin superfamily Get druggable targets OG5_145685 All targets in OG5_145685
Schistosoma japonicum Octopamine receptor, putative Get druggable targets OG5_133249 All targets in OG5_133249
Echinococcus granulosus hypothetical protein Get druggable targets OG5_144688 All targets in OG5_144688
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_133249 All targets in OG5_133249
Schistosoma mansoni biogenic amine (5HT) receptor Get druggable targets OG5_133249 All targets in OG5_133249
Schistosoma japonicum Sodium-dependent dopamine transporter, putative Get druggable targets OG5_128364 All targets in OG5_128364
Schistosoma japonicum ko:K04135 adrenergic receptor, alpha 1a, putative Get druggable targets OG5_128924 All targets in OG5_128924
Schistosoma japonicum Sodium-dependent dopamine transporter, putative Get druggable targets OG5_128364 All targets in OG5_128364
Schistosoma japonicum IPR000175,Sodium:neurotransmitter symporter,domain-containing Get druggable targets OG5_128364 All targets in OG5_128364
Echinococcus granulosus biogenic amine 5HT receptor Get druggable targets OG5_133074 All targets in OG5_133074
Schistosoma japonicum Sodium-dependent dopamine transporter, putative Get druggable targets OG5_128364 All targets in OG5_128364
Schistosoma mansoni biogenic amine (5HT) receptor Get druggable targets OG5_133074 All targets in OG5_133074
Onchocerca volvulus Get druggable targets OG5_128364 All targets in OG5_128364
Treponema pallidum sodium- and chloride- dependent transporter Get druggable targets OG5_128364 All targets in OG5_128364
Schistosoma japonicum Sodium-dependent dopamine transporter, putative Get druggable targets OG5_128364 All targets in OG5_128364
Echinococcus multilocularis serotonin receptor Get druggable targets OG5_133249 All targets in OG5_133249
Schistosoma japonicum 5-hydroxytryptamine receptor, putative Get druggable targets OG5_132667 All targets in OG5_132667
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_133249 All targets in OG5_133249
Schistosoma japonicum Sodium-dependent dopamine transporter, putative Get druggable targets OG5_128364 All targets in OG5_128364
Echinococcus multilocularis conserved hypothetical protein Get druggable targets OG5_144688 All targets in OG5_144688
Loa Loa (eye worm) serotonin transporter b Get druggable targets OG5_128364 All targets in OG5_128364
Loa Loa (eye worm) norepinephrine transporter Get druggable targets OG5_128364 All targets in OG5_128364
Loa Loa (eye worm) solute carrier family 6 member 4 Get druggable targets OG5_128364 All targets in OG5_128364
Schistosoma mansoni amine GPCR Get druggable targets OG5_128924 All targets in OG5_128924
Schistosoma japonicum expressed protein Get druggable targets OG5_133249 All targets in OG5_133249
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_128364 All targets in OG5_128364
Schistosoma japonicum Sodium-dependent dopamine transporter, putative Get druggable targets OG5_128364 All targets in OG5_128364
Schistosoma japonicum Alpha-1D adrenergic receptor, putative Get druggable targets OG5_128924 All targets in OG5_128924
Echinococcus multilocularis biogenic amine (5HT) receptor Get druggable targets OG5_133074 All targets in OG5_133074
Schistosoma mansoni norepinephrine/norepinephrine transporter Get druggable targets OG5_128364 All targets in OG5_128364
Schistosoma mansoni sodium/chloride dependent transporter Get druggable targets OG5_128364 All targets in OG5_128364
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Brugia malayi Sodium:neurotransmitter symporter family protein solute carrier family 6 (neurotransmitter transporter), member 4 630 aa 574 aa 31.5 %
Brugia malayi hypothetical protein dopamine receptor D3 400 aa 392 aa 19.9 %
Brugia malayi Sodium:neurotransmitter symporter family protein solute carrier family 6 (neurotransmitter transporter), member 2 617 aa 638 aa 32.5 %
Brugia malayi Sodium:neurotransmitter symporter family protein solute carrier family 6 (neurotransmitter transporter), member 3 620 aa 579 aa 33.2 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Trypanosoma cruzi lactoylglutathione lyase-like protein, putative 0.0215182 0.0326909 0.5
Echinococcus granulosus hypothetical protein 0.0874973 0.34122 0.34122
Loa Loa (eye worm) solute carrier family 6 member 4 0.0291991 0.0686081 1
Echinococcus multilocularis serotonin transporter 0.0291991 0.0686081 0.163681
Echinococcus multilocularis conserved hypothetical protein 0.0833333 0.321749 0.767611
Echinococcus multilocularis tm gpcr rhodopsin gpcr rhodopsin superfamily 0.104164 0.419156 1
Brugia malayi Serotonin receptor 0.0597195 0.211327 1
Brugia malayi Sodium:neurotransmitter symporter family protein 0.0291991 0.0686081 0.201064
Schistosoma mansoni amine GPCR 0.0241639 0.045063 0.282982
Loa Loa (eye worm) norepinephrine transporter 0.0291991 0.0686081 1
Loa Loa (eye worm) hypothetical protein 0.0291991 0.0686081 1
Loa Loa (eye worm) hypothetical protein 0.0291991 0.0686081 1
Onchocerca volvulus 0.0291991 0.0686081 1
Schistosoma mansoni biogenic amine (5HT) receptor 0.0485815 0.159243 1
Treponema pallidum sodium- and chloride- dependent transporter 0.0291991 0.0686081 0.5
Echinococcus granulosus serotonin transporter 0.0291991 0.0686081 0.0686081
Echinococcus granulosus Solute carrier family 22 5 0.228378 1 1
Plasmodium falciparum glyoxalase I 0.0215182 0.0326909 0.5
Loa Loa (eye worm) hypothetical protein 0.0215182 0.0326909 0.476488
Echinococcus granulosus tm gpcr rhodopsin 0.104164 0.419156 0.419156
Schistosoma mansoni sodium/chloride dependent transporter 0.0291991 0.0686081 0.430838
Loa Loa (eye worm) serotonin transporter b 0.0291991 0.0686081 1
Loa Loa (eye worm) hypothetical protein 0.0291991 0.0686081 1
Plasmodium vivax glyoxalase I, putative 0.0215182 0.0326909 0.5
Schistosoma mansoni norepinephrine/norepinephrine transporter 0.0291991 0.0686081 0.430838
Leishmania major glyoxalase I,trypanothione-dependent glyoxalase I 0.0215182 0.0326909 0.5
Echinococcus granulosus biogenic amine 5HT receptor 0.0485815 0.159243 0.159243
Trypanosoma cruzi lactoylglutathione lyase-like protein, putative 0.0215182 0.0326909 0.5
Toxoplasma gondii glyoxalase I, putative 0.0215182 0.0326909 0.5
Echinococcus multilocularis biogenic amine (5HT) receptor 0.0485815 0.159243 0.379914

Activities

Activity type Activity value Assay description Source Reference
EC50 (binding) = 0.16 uM Displacement of [3H]8-OH-DPAT from human recombinant 5HT1A receptor expressed in CHO cells ChEMBL. 16562853
IC50 (functional) = 2700 ng/ml Antimalarial activity against chloroquine-resistant Plasmodium falciparum W2 as [3H]hypoxanthine uptake ChEMBL. 8786363
IC50 (functional) = 7150 ng/ml Antimalarial activity against chloroquine-sensitive Plasmodium falciparum D6 as [3H]hypoxanthine uptake ChEMBL. 8786363
IC50 (binding) = 218.81 uM Inhibition of equine serum BChE preincubated for 15 mins followed by addition of S-butyrylthiocholine chloride as substrate measured after 30 mins by Ellman's microplate assay ChEMBL. 27492195
Inhibition (binding) = 38.79 % Inhibition of electric eel AChE at 100 ug/ml preincubated for 15 mins followed by addition of acetylthiocholine iodide as substrate measured after 30 mins by Ellman's microplate assay ChEMBL. 27492195
Inhibition (binding) < 50 % Displacement of [3H]prazosin from human recombinant adrenergic alpha1D receptor by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]prazosin from human recombinant adrenergic alpha1A receptor by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]GR65630 from human recombinant 5-HT3 receptor expressed in HEKT cell membranes by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]5-HT from human recombinant 5-HT1E receptor expressed in HEK cell membranes by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]rauwolscine from human recombinant adrenergic alpha2B receptor expressed in HEKT cell membranes by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]N-methylspiperone from human recombinant dopamine D2 receptor expressed in fibroblasts cell membranes by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]N-methylspiperone from human recombinant dopamine D4 receptor by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]SCH23390 from human recombinant dopamine D5 receptor expressed in HEKT cell membranes by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]DADLE from human recombinant DOR expressed in HEK cell membranes by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]pyrilamine from human recombinant histamine H1 receptor expressed in HEK cell membranes by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]alpha-methylhistamine from human recombinant histamine H3 receptor expressed in HEKFlp-In cell membranes by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]histamine from human recombinant histamine H4 receptor by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]U69593 from human recombinant KOR expressed in HEK cell membranes by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]QNB/[3H]]NMS from human recombinant muscarinic M1 receptor expressed in CHO cell membranes by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]QNB/[3H]]NMS from human recombinant muscarinic M2 receptor expressed in CHO cell membranes by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]QNB/[3H]]NMS from human recombinant muscarinic M3 receptor expressed in CHO cell membranes by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]QNB/[3H]]NMS from human recombinant muscarinic M4 receptor expressed in CHO cell membranes by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]QNB/[3H]]NMS from human recombinant muscarinic M5 receptor expressed in CHO cell membranes by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]DAMGO from human recombinant MOR expressed in HEK cell membranes by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Displacement of [3H]PK11195 from rat brain PBR by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) < 50 % Binding affinity to guinea pig sigma1 receptor by radioligand binding assay ChEMBL. 25695425
Inhibition (binding) = 50.95 % Inhibition of equine serum BChE at 100 ug/ml preincubated for 15 mins followed by addition of S-butyrylthiocholine chloride as substrate measured after 30 mins by Ellman's microplate assay ChEMBL. 27492195
Ki (binding) Displacement of [3H]ketanserin from human recombinant 5-HT2A receptor expressed in HEKT cell membranes by radioligand binding assay ChEMBL. 25695425
Ki (binding) = 20 nM Displacement of [3H]LSD from human recombinant 5-HT7 receptor expressed in HEK cell membranes by radioligand binding assay ChEMBL. 25695425
Ki (binding) = 306 nM Displacement of [3H]LSD from human recombinant 5-HT6 receptor expressed in HEK cell membranes by radioligand binding assay ChEMBL. 25695425
Ki (binding) = 314 nM Displacement of [3H]Way100635 from human recombinant 5-HT1A receptor expressed in CHO cell membranes by radioligand binding assay ChEMBL. 25695425
Ki (binding) = 323 nM Displacement of [3H]LSD from human recombinant 5-HT2B receptor expressed in HEK cell membranes by radioligand binding assay ChEMBL. 25695425
Ki (binding) = 373 nM Displacement of [3H]SCH23390 from human recombinant dopamine D1 receptor expressed in HEKT cell membranes by radioligand binding assay ChEMBL. 25695425
Ki (binding) = 566 nM Displacement of [3H]LSD from human recombinant 5-HT5A receptor expressed in Flp-In CHO cell membranes by radioligand binding assay ChEMBL. 25695425
Ki (binding) > 950 nM Displacement of [3H]mesulergine from human recombinant 5-HT2C receptor expressed in Flp-IN HEK cell membranes by radioligand binding assay ChEMBL. 25695425
Ki (binding) > 950 nM Displacement of [3H]prazosin from human recombinant adrenergic alpha1B receptor expressed in HEKT cell membranes by radioligand binding assay ChEMBL. 25695425
Ki (binding) > 950 nM Displacement of [3H]rauwolscine from human recombinant adrenergic alpha2C receptor expressed in MDCK cell membranes by radioligand binding assay ChEMBL. 25695425
Ki (binding) > 950 nM Displacement of [3H]CGP12177 from human recombinant adrenergic beta2 receptor expressed in CHO Flp-In cell membranes by radioligand binding assay ChEMBL. 25695425
Ki (binding) > 950 nM Displacement of [3H]N-methylspiperone from human recombinant dopamine D3 receptor expressed in HEKT cell membranes by radioligand binding assay ChEMBL. 25695425
Ki (binding) > 950 nM Displacement of [3H]WIN35428 from human recombinant DAT expressed in HEK cell membranes by radioligand binding assay ChEMBL. 25695425
Ki (binding) > 950 nM Displacement of [3H]nisoxetine from human recombinant NET expressed in HEK cell membranes by radioligand binding assay ChEMBL. 25695425
Ki (binding) > 950 nM Displacement of [3H]citalopram from human recombinant SERT expressed in HEK cell membranes by radioligand binding assay ChEMBL. 25695425
Ki (binding) = 0.085 uM Displacement of [3H]8-OH-DPAT from human recombinant 5HT1A receptor expressed in CHO cells ChEMBL. 16562853

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Plasmodium falciparum ChEMBL23 8786363

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.

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