Detailed information for compound 579449

Basic information

Technical information
  • TDR Targets ID: 579449
  • Name: (6aR,9S,10S,10aR)-6,6,9-trimethyl-3-pentyl-7, 8,10,10a-tetrahydro-6aH-benzo[c]chromene-1,9, 10-triol
  • MW: 348.476 | Formula: C21H32O4
  • H donors: 3 H acceptors: 3 LogP: 4.1 Rotable bonds: 4
    Rule of 5 violations (Lipinski): 1
  • SMILES: CCCCCc1cc(O)c2c(c1)OC([C@H]1[C@H]2[C@H](O)[C@@](CC1)(C)O)(C)C
  • InChi: 1S/C21H32O4/c1-5-6-7-8-13-11-15(22)18-16(12-13)25-20(2,3)14-9-10-21(4,24)19(23)17(14)18/h11-12,14,17,19,22-24H,5-10H2,1-4H3/t14-,17-,19+,21+/m1/s1
  • InChiKey: TZGCTXUTNDNTTE-DYZHCLJRSA-N  


Substructure search Similarity search

Network

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Synonyms

  • (6aR,9S,10S,10aR)-6,6,9-trimethyl-3-pentyl-7,8,10,10a-tetrahydro-6aH-benzo[c][1]benzopyran-1,9,10-triol
  • (6aR,9S,10S,10aR)-3-amyl-6,6,9-trimethyl-7,8,10,10a-tetrahydro-6aH-benzo[c]chromene-1,9,10-triol
  • cannabiripsol
  • 72236-32-9
  • (6aR,9S,10S,10aR)-9,10-Dihydroxyhexahydrocannabinol
  • 6H-Dibenzo(b,d)pyran-1,9,10-triol, 6a,7,8,9,10,10a-hexahydro-6,6,9-trimethyl-3-pentyl-, (6aR-(6aalpha,9beta,10alpha,10abeta))-

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens cannabinoid receptor 2 (macrophage) 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
Loa Loa (eye worm) hypothetical protein 0.0034 0.0685 0.0803
Mycobacterium tuberculosis Probable reductase 0.0191 0.4662 0.8958
Trichomonas vaginalis dihydrolipoamide dehydrogenase, putative 0.0008 0.0033 0.0057
Brugia malayi glutathione reductase 0.0084 0.1953 0.3846
Trichomonas vaginalis glutathione reductase, putative 0.0029 0.0571 0.0995
Schistosoma mansoni histone-lysine n-methyltransferase suv9 0.003 0.0596 0.0565
Echinococcus granulosus dihydrolipoamide dehydrogenase 0.0029 0.0571 0.054
Trichomonas vaginalis dihydroorotate dehydrogenase, putative 0.0008 0.0033 0.0057
Toxoplasma gondii hypothetical protein 0.0119 0.2841 1
Loa Loa (eye worm) hypothetical protein 0.0119 0.2841 0.346
Loa Loa (eye worm) hypothetical protein 0.0049 0.1077 0.1286
Toxoplasma gondii histone lysine methyltransferase SET1 0.0055 0.1217 0.4218
Chlamydia trachomatis dihydrolipoyl dehydrogenase 0.0029 0.0571 1
Schistosoma mansoni hypothetical protein 0.0403 1 1
Loa Loa (eye worm) hypothetical protein 0.003 0.0596 0.0693
Trichomonas vaginalis disulfide oxidoreductase, putative 0.0008 0.0033 0.0057
Trichomonas vaginalis set domain proteins, putative 0.0234 0.5739 1
Echinococcus granulosus mixed lineage leukemia protein mll 0.0008 0.0043 0.001
Echinococcus multilocularis histone lysine N methyltransferase MLL3 0.001 0.0086 0.0054
Toxoplasma gondii histone lysine methyltransferase SET/SUV39 0.003 0.0596 0.2004
Schistosoma mansoni histone-lysine n-methyltransferase setb1 0.003 0.0596 0.0565
Schistosoma mansoni dihydrolipoamide dehydrogenase 0.0029 0.0571 0.054
Mycobacterium ulcerans flavoprotein disulfide reductase 0.0029 0.0571 1
Schistosoma mansoni hypothetical protein 0.0016 0.023 0.0198
Entamoeba histolytica dihydropyrimidine dehydrogenase, putative 0.0008 0.0033 0.5
Schistosoma mansoni hypothetical protein 0.0016 0.023 0.0198
Leishmania major 2-oxoglutarate dehydrogenase, e3 component, lipoamidedehydrogenase-like protein 0.0029 0.0571 0.2803
Plasmodium falciparum thioredoxin reductase 0.0029 0.0571 0.2803
Echinococcus multilocularis thioredoxin glutathione reductase 0.0084 0.1965 0.1939
Brugia malayi calcium-independent alpha-latrotoxin receptor 2, putative 0.0016 0.023 0.0395
Echinococcus granulosus 5'partial|histone lysine N methyltransferase SETDB2 0.0028 0.0553 0.0522
Toxoplasma gondii pyruvate dehydrogenase complex subunit PDH-E3II 0.0029 0.0571 0.1916
Plasmodium vivax glutathione reductase, putative 0.0084 0.1953 1
Echinococcus multilocularis diuretic hormone 44 receptor GPRdih2 0.0016 0.023 0.0198
Echinococcus granulosus diuretic hormone 44 receptor GPRdih2 0.0016 0.023 0.0198
Trichomonas vaginalis mercuric reductase, putative 0.0029 0.0571 0.0995
Trypanosoma brucei dihydrolipoamide dehydrogenase 0.0029 0.0571 0.2803
Loa Loa (eye worm) pigment dispersing factor receptor c 0.0049 0.1077 0.1286
Leishmania major acetoin dehydrogenase e3 component-like protein 0.0029 0.0571 0.2803
Giardia lamblia NADH oxidase lateral transfer candidate 0.0029 0.0571 1
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative 0.0029 0.0571 0.2803
Onchocerca volvulus 0.0234 0.5739 1
Leishmania major trypanothione reductase 0.0084 0.1953 1
Schistosoma mansoni hypothetical protein 0.0034 0.0685 0.0654
Brugia malayi latrophilin 2 splice variant baaae 0.0034 0.0685 0.1306
Loa Loa (eye worm) hypothetical protein 0.033 0.815 1
Brugia malayi Thioredoxin reductase 0.0084 0.1953 0.3846
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0029 0.0571 1
Echinococcus granulosus thioredoxin glutathione reductase 0.0084 0.1965 0.1939
Trypanosoma cruzi trypanothione reductase, putative 0.0084 0.1953 1
Trypanosoma cruzi trypanothione reductase, putative 0.0029 0.0571 0.2803
Onchocerca volvulus 0.003 0.0596 0.0986
Echinococcus granulosus GPCR family 2 0.0016 0.023 0.0198
Loa Loa (eye worm) inward rectifying k channel family protein 1 0.033 0.815 1
Echinococcus granulosus cpg binding protein 0.003 0.0593 0.0562
Mycobacterium tuberculosis Probable oxidoreductase 0.0213 0.52 1
Echinococcus multilocularis dnaJ subfamily B 0.0403 1 1
Mycobacterium tuberculosis Probable membrane NADH dehydrogenase NdhA 0.0191 0.4662 0.8958
Mycobacterium tuberculosis NAD(P)H quinone reductase LpdA 0.0213 0.52 1
Leishmania major dihydrolipoamide dehydrogenase, putative 0.0029 0.0571 0.2803
Echinococcus multilocularis mixed lineage leukemia protein mll 0.0008 0.0043 0.001
Schistosoma mansoni hypothetical protein 0.0016 0.023 0.0198
Mycobacterium tuberculosis Probable soluble pyridine nucleotide transhydrogenase SthA (STH) (NAD(P)(+) transhydrogenase [B-specific]) (nicotinamide nucleot 0.0029 0.0571 0.1042
Toxoplasma gondii thioredoxin reductase 0.0084 0.1953 0.6836
Schistosoma mansoni histone-lysine n-methyltransferase setb1 0.003 0.0596 0.0565
Schistosoma mansoni hypothetical protein 0.0016 0.023 0.0198
Loa Loa (eye worm) histone methyltransferase 0.001 0.0086 0.0066
Plasmodium vivax dihydrolipoyl dehydrogenase, apicoplast, putative 0.0029 0.0571 0.2803
Schistosoma mansoni cpg binding protein 0.003 0.0593 0.0562
Schistosoma mansoni mixed-lineage leukemia protein mll 0.0008 0.0043 0.001
Wolbachia endosymbiont of Brugia malayi dihydrolipoamide dehydrogenase E3 component 0.0029 0.0571 1
Loa Loa (eye worm) hypothetical protein 0.0119 0.2841 0.346
Mycobacterium tuberculosis Probable dehydrogenase 0.0191 0.4662 0.8958
Mycobacterium tuberculosis NADPH-dependent mycothiol reductase Mtr 0.0084 0.1953 0.3716
Mycobacterium tuberculosis Dihydrolipoamide dehydrogenase LpdC (lipoamide reductase (NADH)) (lipoyl dehydrogenase) (dihydrolipoyl dehydrogenase) (diaphoras 0.0213 0.52 1
Entamoeba histolytica glutamate synthase beta subunit, putative 0.0008 0.0033 0.5
Echinococcus granulosus cadherin EGF LAG seven pass G type receptor 0.0016 0.023 0.0198
Entamoeba histolytica NAD(FAD)-dependent dehydrogenase, putative 0.0008 0.0033 0.5
Loa Loa (eye worm) pre-SET domain-containing protein family protein 0.0206 0.5024 0.6149
Loa Loa (eye worm) CXXC zinc finger family protein 0.0028 0.0552 0.0639
Brugia malayi Latrophilin receptor protein 2 0.0016 0.023 0.0395
Loa Loa (eye worm) glutathione reductase 0.0084 0.1953 0.2365
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative 0.0029 0.0571 0.2803
Trichomonas vaginalis glutamate synthase, putative 0.0008 0.0033 0.0057
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative 0.0029 0.0571 0.2803
Schistosoma mansoni histone-lysine n-methyltransferase setb1 0.003 0.0596 0.0565
Brugia malayi F/Y-rich N-terminus family protein 0.001 0.0084 0.0102
Brugia malayi alpha keto acid dehydrogenase complex, E3 component, lipoamide dehydrogenase 0.0021 0.0377 0.0689
Schistosoma mansoni mixed-lineage leukemia protein mll 0.0061 0.1379 0.1351
Trichomonas vaginalis dihydroorotate dehydrogenase, putative 0.0008 0.0033 0.0057
Entamoeba histolytica glutamate synthase beta subunit, putative 0.0008 0.0033 0.5
Trypanosoma cruzi dihydrolipoyl dehydrogenase, putative 0.0029 0.0571 0.2803
Echinococcus multilocularis GPCR, family 2 0.0016 0.023 0.0198
Brugia malayi Corticotropin releasing factor receptor 2 precursor, putative 0.0049 0.1077 0.2092
Trypanosoma brucei dihydrolipoyl dehydrogenase 0.0029 0.0571 0.2803
Mycobacterium tuberculosis Probable nitrite reductase [NAD(P)H] large subunit [FAD flavoprotein] NirB 0.0191 0.4662 0.8958
Entamoeba histolytica disulphide oxidoreductase, putative 0.0008 0.0033 0.5
Echinococcus granulosus histone lysine N methyltransferase MLL3 0.001 0.0086 0.0054
Trypanosoma brucei dihydrolipoamide dehydrogenase, point mutation 0.0029 0.0571 0.2803
Trypanosoma brucei dihydrolipoamide dehydrogenase 0.0029 0.0571 0.2803
Mycobacterium leprae PROBABLE NADH DEHYDROGENASE NDH 0.0191 0.4662 0.8958
Loa Loa (eye worm) thioredoxin reductase 0.0084 0.1953 0.2365
Loa Loa (eye worm) latrophilin receptor protein 2 0.0016 0.023 0.0243
Plasmodium vivax thioredoxin reductase, putative 0.0084 0.1953 1
Brugia malayi Pre-SET motif family protein 0.003 0.0596 0.1127
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative 0.0029 0.0571 0.2803
Brugia malayi Pre-SET motif family protein 0.0206 0.5024 1
Plasmodium falciparum dihydrolipoyl dehydrogenase, mitochondrial 0.0029 0.0571 0.2803
Trypanosoma cruzi dihydrolipoyl dehydrogenase, putative 0.0029 0.0571 0.2803
Echinococcus multilocularis cadherin EGF LAG seven pass G type receptor 0.0016 0.023 0.0198
Trichomonas vaginalis disulfide oxidoreductase, putative 0.0008 0.0033 0.0057
Schistosoma mansoni cpg binding protein 0.003 0.0593 0.0562
Trichomonas vaginalis disulfide oxidoreductase, putative 0.0008 0.0033 0.0057
Echinococcus multilocularis dihydrolipoamide dehydrogenase 0.0029 0.0571 0.054
Plasmodium falciparum thioredoxin reductase 0.0084 0.1953 1
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative 0.0029 0.0571 0.2803
Plasmodium falciparum dihydrolipoyl dehydrogenase, apicoplast 0.0029 0.0571 0.2803
Trichomonas vaginalis apoptosis inducing factor, putative 0.0008 0.0033 0.0057
Onchocerca volvulus 0.0028 0.0552 0.091
Trichomonas vaginalis glutamate synthase, putative 0.0008 0.0033 0.0057
Echinococcus multilocularis histone lysine N methyltransferase MLL3 0.0008 0.0043 0.001
Mycobacterium ulcerans dihydrolipoamide dehydrogenase 0.0029 0.0571 1
Mycobacterium ulcerans dihydrolipoamide dehydrogenase, LpdB 0.0029 0.0571 1
Trichomonas vaginalis disulfide oxidoreductase, putative 0.0008 0.0033 0.0057
Echinococcus granulosus histone lysine methyltransferase setb 0.003 0.0596 0.0565
Trypanosoma brucei trypanothione reductase 0.0084 0.1953 1
Brugia malayi Pyridine nucleotide-disulphide oxidoreductase, dimerisation domain containing protein 0.0021 0.0377 0.0689
Plasmodium vivax SET domain protein, putative 0.003 0.0596 0.2931
Loa Loa (eye worm) hypothetical protein 0.0016 0.023 0.0243
Mycobacterium tuberculosis Probable NADH dehydrogenase Ndh 0.0191 0.4662 0.8958
Entamoeba histolytica pyridine nucleotide-disulfide oxidoreductase family protein 0.0008 0.0033 0.5
Echinococcus multilocularis cpg binding protein 0.003 0.0593 0.0562
Trichomonas vaginalis disulfide oxidoreductase, putative 0.0008 0.0033 0.0057
Plasmodium vivax dihydrolipoyl dehydrogenase, mitochondrial, putative 0.0029 0.0571 0.2803
Mycobacterium leprae DIHYDROLIPOAMIDE DEHYDROGENASE LPD (LIPOAMIDE REDUCTASE (NADH)) (LIPOYL DEHYDROGENASE) (DIHYDROLIPOYL DEHYDROGENASE) (DIAPHORASE 0.0213 0.52 1
Mycobacterium tuberculosis Putative ferredoxin reductase 0.0191 0.4662 0.8958
Brugia malayi dihydrolipoyl dehydrogenase, mitochondrial precursor, putative 0.0029 0.0571 0.1078
Echinococcus multilocularis histone lysine N methyltransferase SETMAR 0.003 0.0596 0.0565
Plasmodium falciparum glutathione reductase 0.0029 0.0571 0.2803
Echinococcus multilocularis histone lysine methyltransferase setb histone lysine methyltransferase eggless 0.003 0.0596 0.0565
Trichomonas vaginalis disulfide oxidoreductase, putative 0.0008 0.0033 0.0057
Schistosoma mansoni cpg binding protein 0.0028 0.0552 0.0521
Entamoeba histolytica thioredoxin reductase, putative 0.0008 0.0033 0.5
Plasmodium falciparum glutathione reductase 0.0084 0.1953 1
Trypanosoma cruzi dihydrolipoamide dehydrogenase, putative 0.0029 0.0571 0.2803
Trichomonas vaginalis dihydropyrimidine dehydrogenase, putative 0.0008 0.0033 0.0057
Brugia malayi Calcitonin receptor-like protein seb-1 0.0049 0.1077 0.2092
Treponema pallidum NADH oxidase 0.0029 0.0571 1
Leishmania major dihydrolipoamide dehydrogenase, putative 0.0029 0.0571 0.2803
Echinococcus granulosus histone lysine N methyltransferase MLL3 0.0008 0.0043 0.001
Toxoplasma gondii NADPH-glutathione reductase 0.0029 0.0571 0.1916
Brugia malayi CXXC zinc finger family protein 0.0028 0.0552 0.104

Activities

Activity type Activity value Assay description Source Reference
Ki (binding) = 2143 nM Displacement of [3H]CP55940 from full length human recombinant CB2 receptor expressed in HEK293 cells after 90 mins by scintillation counting analysis ChEMBL. 26000707
Ki (binding) = 5668 nM Displacement of [3H]CP55940 from full length human recombinant CB1 receptor expressed in HEK293 cells after 90 mins by scintillation counting analysis ChEMBL. 26000707
T (functional) = 0.45 degrees C Neurobehavioral effect on Swiss Webster mouse assessed as decrease in rectal temperature at 20 mg/kg, ip (Rvb = 0.58 +/- 0.26 degC) by mouse tetrad assay ChEMBL. 26000707

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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