Detailed information for compound 349505

Basic information

Technical information
  • TDR Targets ID: 349505
  • Name: (6aR,10aR)-6,6,9-trimethyl-3-(2-methylpentan- 2-yl)-6a,7,10,10a-tetrahydrobenzo[c]chromene
  • MW: 312.489 | Formula: C22H32O
  • H donors: 0 H acceptors: 0 LogP: 6.42 Rotable bonds: 3
    Rule of 5 violations (Lipinski): 1
  • SMILES: CCCC(c1ccc2c(c1)OC([C@H]1[C@H]2CC(=CC1)C)(C)C)(C)C
  • InChi: 1S/C22H32O/c1-7-12-21(3,4)16-9-10-17-18-13-15(2)8-11-19(18)22(5,6)23-20(17)14-16/h8-10,14,18-19H,7,11-13H2,1-6H3/t18-,19+/m0/s1
  • InChiKey: YSBFLLZNALVODA-RBUKOAKNSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (6aR,10aR)-3-(1,1-dimethylbutyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c]chromene
  • (6aR,10aR)-3-(1,1-dimethylbutyl)-6,6,9-trimethyl-6a,7,10,10a-tetrahydrobenzo[c][1]benzopyran
  • 1,1-dimethylbutyl-1-deoxy-Delta(9)-THC
  • 3-(1,1-Dimethylbutyl)-1-deoxy-Delta8-THC
  • 3-(1,1-Dimethylbutyl)-1-deoxy-Delta8-tetrahydrocannabinol
  • J2753_SIGMA
  • JWH-133

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Mus musculus cannabinoid receptor 1 (brain) Starlite/ChEMBL References
Homo sapiens cannabinoid receptor 2 (macrophage) Starlite/ChEMBL References
Mus musculus cannabinoid receptor 2 (macrophage) Starlite/ChEMBL References
Rattus norvegicus Cannabinoid CB1 receptor Starlite/ChEMBL References
Homo sapiens cannabinoid receptor 1 (brain) 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
Trypanosoma cruzi GMP reductase 0.278 1 0.5
Mycobacterium leprae Probable inosine-5'-monophosphate dehydrogenase GuaB2 (IMP dehydrogenase) (IMPDH) (IMPD) 0.278 1 1
Plasmodium vivax inosine-5'-monophosphate dehydrogenase, putative 0.2614 0.8869 0.5
Leishmania major guanosine monophosphate reductase 0.278 1 0.5
Trypanosoma cruzi GMP reductase 0.278 1 0.5
Toxoplasma gondii IMP dehydrogenas 0.278 1 0.5
Mycobacterium ulcerans inosine 5'-monophosphate dehydrogenase 0.278 1 1
Trypanosoma cruzi inosine-5'-monophosphate dehydrogenase, putative 0.278 1 0.5
Leishmania major inosine-5-monophosphate dehydrogenase 0.278 1 0.5
Schistosoma mansoni inosine-5-monophosphate dehydrogenase 0.278 1 0.5
Mycobacterium ulcerans inosine 5-monophosphate dehydrogenase 0.2614 0.8869 0.8869
Plasmodium falciparum inosine-5'-monophosphate dehydrogenase 0.2614 0.8869 0.5
Echinococcus multilocularis inosine 5' monophosphate dehydrogenase 2 0.278 1 0.5
Echinococcus granulosus inosine 5' monophosphate dehydrogenase 2 0.278 1 0.5
Trypanosoma brucei inosine-5'-monophosphate dehydrogenase 0.278 1 0.5
Trypanosoma cruzi inosine-5'-monophosphate dehydrogenase, putative 0.278 1 0.5
Wolbachia endosymbiont of Brugia malayi IMP dehydrogenase 0.278 1 0.5
Mycobacterium tuberculosis Probable inosine-5'-monophosphate dehydrogenase GuaB2 (imp dehydrogenase) (inosinic acid dehydrogenase) (inosinate dehydrogenase 0.278 1 1
Loa Loa (eye worm) IMP dehydrogenase 1 0.278 1 0.5
Mycobacterium leprae Probable inosine-5'-monophosphate dehydrogenase GuaB3 (IMP dehydrogenase 2) (inosinic acid dehydrogenase) (inosinate dehydrogena 0.1459 0.0954 0.0954
Trypanosoma cruzi inosine-5'-monophosphate dehydrogenase, putative 0.278 1 0.5
Trypanosoma brucei GMP reductase 0.278 1 0.5

Activities

Activity type Activity value Assay description Source Reference
Activity (binding) Displacement of [3H]-CP-55940 from human CB1 receptor expressed in CHO cells ChEMBL. 17915849
Activity (binding) 0 Displacement of [3H]-CP-55940 from human CB1 receptor expressed in CHO cells ChEMBL. 17915849
Activity (binding) 0 Displacement of [3H]-CP-55940 from human CB2 receptor expressed in CHO cells ChEMBL. 17915849
Activity (functional) = 148 % Effect on human CB2 receptor stimulation by [35S]-GTPgammaS binding at 10 uM (basal value set at 100%) ChEMBL. 16392793
Activity (functional) = 148 % Effect on human CB2 receptor stimulation by [35S]-GTPgammaS binding at 10 uM (basal value set at 100%) ChEMBL. 16392793
Activity (functional) = 201.4 % Activity at human CB2 receptor expressed in CHO cells assessed as stimulated [35S]GTPgammaS binding relative to control ChEMBL. 17915849
Activity (functional) = 201.4 % Activity at human CB2 receptor expressed in CHO cells assessed as stimulated [35S]GTPgammaS binding relative to control ChEMBL. 17915849
EC50 (functional) = -5.7 Displacement of [35S]GTPgammaS from rat cerebellar CB1 receptor ChEMBL. 16420041
EC50 (functional) = 4 nM Agonist activity at human CB2 receptor expressed in CHO cells assessed as stimulation of [35S]GTPgammaS binding after 1.5 hrs by liquid scintillation spectrophotometry ChEMBL. 20943404
EC50 (functional) = 145.6 nM Effect on [35S]GTPgammaS binding to human CB2 receptor ChEMBL. 16392793
EC50 (functional) = 145.6 nM Effect on [35S]GTPgammaS binding to human CB2 receptor ChEMBL. 16392793
Emax (functional) = 111.5 % Agonist activity at human CB2 receptor expressed in CHO cells assessed as stimulation of [35S]GTPgammaS binding after 1.5 hrs by liquid scintillation spectrophotometry relative to CP-55940 ChEMBL. 20943404
Emax (functional) = 149 % Effect on [35S]GTPgammaS binding to human CB2 receptor ChEMBL. 16392793
Emax (functional) = 149 % Effect on [35S]GTPgammaS binding to human CB2 receptor ChEMBL. 16392793
Emax (functional) = 158 % Displacement of [35S]GTPgammaS from rat cerebellar CB1 receptor ChEMBL. 16420041
Emax (functional) = 158 % Displacement of [35S]GTPgammaS from rat cerebellar CB1 receptor ChEMBL. 16420041
IC50 (binding) = 0.55 uM Displacement of human recombinant CB2 receptor expressed in HEK293 cell membranes incubated for 90 mins by radioligand binding assay ChEMBL. No reference
IC50 (binding) > 10 uM Displacement of human recombinant CB1 receptor expressed in HEK293 cell membranes incubated for 90 mins by radioligand binding assay ChEMBL. No reference
IC50 (functional) = 11.65 uM Cytotoxicity against human LNCAP cells expressing CB2 receptor assessed as decrease in cell viability after 72 hrs by neutral red uptake and accumulation assay ChEMBL. 25935384
Imax (binding) < 50 % Maximum displacement of human recombinant CB1 receptor expressed in HEK293 cell membranes at 10 uM incubated for 90 mins by radioligand binding assay ChEMBL. No reference
Imax (binding) = 50 % Maximum displacement of human recombinant CB2 receptor expressed in HEK293 cell membranes at 10 uM incubated for 90 mins by radioligand binding assay ChEMBL. No reference
Inhibition (functional) = 87 % Agonist activity at human CB2 receptor expressed in CHO cells assessed as inhibition of forskolin-induced cAMP level at 1 uM by scintillation counting ChEMBL. 22548457
Inhibition (functional) = 94 % Agonist activity at human CB2 receptor expressed in CHO cells assessed as inhibition of forskolin-induced cAMP level at 10 uM by scintillation counting ChEMBL. 22548457
Ki (binding) = 0.023 nM Displacement of [3H]CP-55940 from human recombinant CB2 receptor ChEMBL. 19143566
Ki (binding) = 0.797 nM Displacement of [3H]CP-55940 from human recombinant CB1 receptor ChEMBL. 19143566
Ki (binding) = 1.82 nM Displacement of [3H]CP55940 from recombinant human CB2 receptor expressed in human HEK293 cell membrane after 90 mins ChEMBL. 22483967
Ki (binding) = 3 nM Displacement of [3H]CP-55940 from human recombinant CB2 receptor expressed in HEK293 cells ChEMBL. 19435366
Ki (binding) = 3 nM Displacement of [3H]CP55,940 from human recombinant CB2 receptor expressed in HEK293 cell membranes after 90 mins ChEMBL. 24518874
Ki (binding) = 3 nM HEK293DHEK293iHEK293sHEK293pHEK293lHEK293aHEK293cHEK293eHEK293mHEK293eHEK293nHEK293tHEK293 HEK293oHEK293fHEK293 HEK293[HEK2933HEK293HHEK293]HEK293CHEK293PHEK293-HEK2935HEK2935HEK293,HEK2939HEK2934HEK2930HEK293 HEK293fHEK293rHEK293oHEK293mHEK293 HEK293hHEK293uHEK293mHEK293aHEK293nHEK293 HEK293rHEK293eHEK293cHEK293oHEK293mHEK293bHEK293iHEK293nHEK293aHEK293nHEK293tHEK293 HEK293CHEK293BHEK2932HEK293RHEK293 HEK293eHEK293xHEK293pHEK293rHEK293eHEK293sHEK293sHEK293eHEK293dHEK293 HEK293iHEK293nHEK293 HEK293HHEK293EHEK293KHEK293-HEK2932HEK2939HEK2933HEK293 HEK293cHEK293eHEK293lHEK293lHEK293sHEK293 HEK293aHEK293fHEK293tHEK293eHEK293rHEK293 HEK2939HEK2930HEK293 HEK293mHEK293iHEK293nHEK293sHEK293 HEK293bHEK293yHEK293 HEK293lHEK293iHEK293qHEK293uHEK293iHEK293dHEK293 HEK293sHEK293cHEK293iHEK293nHEK293tHEK293iHEK293lHEK293lHEK293aHEK293tHEK293iHEK293oHEK293nHEK293 HEK293cHEK293oHEK293uHEK293nHEK293tHEK293iHEK293nHEK293gHEK293 ChEMBL. 25272206
Ki (binding) = 3 nM Displacement of [3H]CP55,940 from human recombinant CB2 receptor expressed in HEK293 cell membranes after 90 mins ChEMBL. 25486424
Ki (binding) = 3 nM Displacement of [3H]-CP-55940 from recombinant human CB2 receptor overexpressed in HEK293 cell membranes after 90 mins ChEMBL. 25935384
Ki (binding) = 3.4 nM Binding affinity to CB2 receptor ChEMBL. 19143566
Ki (binding) = 3.4 nM Binding affinity to cannabinoid CB2 receptor ChEMBL. 20218623
Ki (binding) = 3.4 nM Displacement of [3H]CP-55940 from human CB2 receptor expressed in CHO cells after 1 hr by liquid scintillation spectrophotometry ChEMBL. 20943404
Ki (binding) = 3.4 nM Displacement of [3H]CP 55940 from human CB2 receptor in cell free system ChEMBL. 21183257
Ki (binding) = 3.4 nM Binding affinity to CB2 receptor ChEMBL. 21872477
Ki (binding) = 3.4 nM Binding affinity to human CB2 receptor ChEMBL. 23865723
Ki (binding) = 20.3 nM Displacement of [3H]-CP-55940 from human CB2 receptor ChEMBL. 16392793
Ki (binding) = 20.3 nM Displacement of [3H]-CP-55940 from human CB2 receptor ChEMBL. 16392793
Ki (binding) = 65 nM Displacement of [3H]CP 55940 from CB2 receptor in DBA/J2 mouse spleen ChEMBL. 17004710
Ki (binding) = 65 nM Displacement of [3H]CP 55940 from CB2 receptor in DBA/J2 mouse spleen ChEMBL. 17004710
Ki (binding) = 116.8 nM Displacement of [3H]CP55940 from recombinant human CB1 receptor expressed in human HEK293 cell membrane after 90 mins ChEMBL. 22483967
Ki (binding) = 458 nM Displacement of [3H]CP 55940 from CB1 receptor in DBA/J2 mouse brain ChEMBL. 17004710
Ki (binding) = 458 nM Displacement of [3H]CP 55940 from CB1 receptor in DBA/J2 mouse brain ChEMBL. 17004710
Ki (binding) = 677 nM Binding affinity to CB1 receptor ChEMBL. 19143566
Ki (binding) = 677 nM Displacement of [3H]CP-55940 from human recombinant CB1 receptor expressed in HEK293 cells ChEMBL. 19435366
Ki (binding) = 677 nM Binding affinity to cannabinoid CB1 receptor ChEMBL. 20218623
Ki (binding) = 677 nM Displacement of [3H]CP-55940 from CB1 receptor in Sprague-Dawley rat brain membranes after 1 hr by liquid scintillation spectrophotometry ChEMBL. 20943404
Ki (binding) = 677 nM Displacement of [3H]CP 55940 from human CB1 receptor in cell free system ChEMBL. 21183257
Ki (binding) = 677 nM Binding affinity to CB1 receptor ChEMBL. 21872477
Ki (binding) = 677 nM Displacement of [3H]CP55,940 from human recombinant CB1 receptor expressed in HEK293 cell membranes after 90 mins ChEMBL. 24518874
Ki (binding) = 677 nM Binding affinity to rat CB1 receptor ChEMBL. 23865723
Ki (binding) = 677 nM HEK293DHEK293iHEK293sHEK293pHEK293lHEK293aHEK293cHEK293eHEK293mHEK293eHEK293nHEK293tHEK293 HEK293oHEK293fHEK293 HEK293[HEK2933HEK293HHEK293]HEK293CHEK293PHEK293-HEK2935HEK2935HEK293,HEK2939HEK2934HEK2930HEK293 HEK293fHEK293rHEK293oHEK293mHEK293 HEK293hHEK293uHEK293mHEK293aHEK293nHEK293 HEK293rHEK293eHEK293cHEK293oHEK293mHEK293bHEK293iHEK293nHEK293aHEK293nHEK293tHEK293 HEK293CHEK293BHEK2931HEK293RHEK293 HEK293eHEK293xHEK293pHEK293rHEK293eHEK293sHEK293sHEK293eHEK293dHEK293 HEK293iHEK293nHEK293 HEK293HHEK293EHEK293KHEK293-HEK2932HEK2939HEK2933HEK293 HEK293cHEK293eHEK293lHEK293lHEK293sHEK293 HEK293aHEK293fHEK293tHEK293eHEK293rHEK293 HEK2939HEK2930HEK293 HEK293mHEK293iHEK293nHEK293sHEK293 HEK293bHEK293yHEK293 HEK293lHEK293iHEK293qHEK293uHEK293iHEK293dHEK293 HEK293sHEK293cHEK293iHEK293nHEK293tHEK293iHEK293lHEK293lHEK293aHEK293tHEK293iHEK293oHEK293nHEK293 HEK293cHEK293oHEK293uHEK293nHEK293tHEK293iHEK293nHEK293gHEK293 ChEMBL. 25272206
Ki (binding) = 677 nM Displacement of [3H]CP55,940 from human recombinant CB1 receptor expressed in HEK293 cell membranes after 90 mins ChEMBL. 25486424
Ki (binding) = 677 nM Displacement of [3H]-CP-55940 from recombinant human CB1 receptor overexpressed in HEK293 cell membranes after 90 mins ChEMBL. 25935384
Ki (binding) = 0.14 uM Displacement of human recombinant CB2 receptor expressed in HEK293 cell membranes incubated for 90 mins by Cheng-Prusoff equation based analysis ChEMBL. No reference
Ki (binding) > 10 uM Displacement of human recombinant CB1 receptor expressed in HEK293 cell membranes incubated for 90 mins by Cheng-Prusoff equation based analysis ChEMBL. No reference
Log EC50 (functional) = 5.7 Displacement of [35S]GTPgammaS from rat cerebellar CB1 receptor ChEMBL. 16420041
Ratio Ki (binding) = 7 Selectivity for DBA/J2 mouse CB2 receptor over CB1 receptor ChEMBL. 17004710
Ratio Ki (binding) = 7 Selectivity for DBA/J2 mouse CB2 receptor over CB1 receptor ChEMBL. 17004710

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Homo sapiens ChEMBL23 25935384

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

17 literature references were collected for this gene.

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