Detailed information for compound 990986

Basic information

Technical information
  • TDR Targets ID: 990986
  • Name: 1617-70-5
  • MW: 424.702 | Formula: C30H48O
  • H donors: 0 H acceptors: 1 LogP: 9.56 Rotable bonds: 1
    Rule of 5 violations (Lipinski): 1
  • SMILES: CC(=C)[C@@H]1CC[C@]2([C@H]1[C@H]1CC[C@H]3[C@@]([C@]1(C)CC2)(C)CC[C@@H]1[C@]3(C)CCC(=O)C1(C)C)C
  • InChi: 1S/C30H48O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-23,25H,1,9-18H2,2-8H3/t20-,21+,22-,23+,25+,27+,28-,29+,30+/m0/s1
  • InChiKey: GRBHNQFQFHLCHO-BHMAJAPKSA-N  


Substructure search Similarity search

Network

Hover on a compound node to display the structore

Synonyms

  • LUPENONE
  • (1R,3aR,4S,5aR,5bR,7aR,11aR,11bR,13aR,13bR)-1-Isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-eicosahydro-cyclopenta[a]chrysen-9-one
  • AIDS-082905
  • AIDS082905
  • ZINC04081760
  • Lup-20(29)-en-3-one (8CI)(9CI)
  • NSC 281807

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Homo sapiens G protein-coupled bile acid receptor 1 Starlite/ChEMBL References
Human immunodeficiency virus 1 Reverse transcriptase Starlite/ChEMBL References
Homo sapiens nuclear receptor subfamily 1, group H, member 4 Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Trypanosoma brucei RNA helicase, putative Get druggable targets OG5_139608 All targets in OG5_139608
Plasmodium yoelii integrase-related Get druggable targets OG5_139608 All targets in OG5_139608
Schistosoma mansoni hypothetical protein Get druggable targets OG5_139608 All targets in OG5_139608
Trypanosoma congolense RNA helicase, putative Get druggable targets OG5_139608 All targets in OG5_139608
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Dictyostelium discoideum hypothetical protein Reverse transcriptase   259 aa 222 aa 22.5 %
Candida albicans ReverseTranscriptase similar to fruit fly Tom element Reverse transcriptase   259 aa 244 aa 27.9 %
Dictyostelium discoideum hypothetical protein Reverse transcriptase   259 aa 226 aa 24.3 %
Candida albicans hypothetical protein Reverse transcriptase   259 aa 223 aa 29.1 %
Trypanosoma congolense Retroviral aspartyl protease/Reverse transcriptase (RNA-dependent DNA polymerase)/RNase H, putative Reverse transcriptase   259 aa 237 aa 29.1 %
Candida albicans polyprotein of retrotransposon Tca8 Reverse transcriptase   259 aa 238 aa 26.5 %
Echinococcus multilocularis RNA directed DNA polymerase (reverse transcriptase) Reverse transcriptase   259 aa 208 aa 26.4 %
Dictyostelium discoideum hypothetical protein Reverse transcriptase   259 aa 245 aa 25.7 %
Echinococcus multilocularis RNA directed DNA polymerase (reverse transcriptase) Reverse transcriptase   259 aa 227 aa 26.4 %
Echinococcus multilocularis RNA directed DNA polymerase (reverse transcriptase) Reverse transcriptase   259 aa 227 aa 26.4 %
Echinococcus granulosus ecdysone induced protein 78C nuclear receptor subfamily 1, group H, member 4 476 aa 402 aa 28.1 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Brugia malayi ecdysteroid receptor 0.00122045 1 1
Loa Loa (eye worm) hypothetical protein 0.00122045 1 1
Brugia malayi photoreceptor-specific nuclear receptor 0.00122045 1 1
Schistosoma mansoni nuclear receptor 2DBD-gamma 0.00122045 1 1
Loa Loa (eye worm) nuclear hormone receptor family member nhr-40 0.00122045 1 1
Echinococcus multilocularis nuclear receptor 2DBD gamma 0.00122045 1 1
Schistosoma mansoni retinoid-x-receptor (RXR) 0.00122045 1 1
Treponema pallidum 4'-phosphopantetheinyl transferase 0.025 1 0.5
Loa Loa (eye worm) hypothetical protein 0.00122045 1 1
Brugia malayi Ligand-binding domain of nuclear hormone receptor family protein 0.00122045 1 1
Brugia malayi Nuclear hormone receptor family member nhr-25 0.00122045 1 1
Loa Loa (eye worm) hypothetical protein 0.00122045 1 1
Toxoplasma gondii 4'-phosphopantetheinyl transferase superfamily protein 0.0049 0.1562 0.5
Brugia malayi Nuclear hormone receptor family member nhr-14 0.00122045 1 1
Schistosoma mansoni FTZ-F1 nuclear receptor-like protein 0.00122045 1 1
Onchocerca volvulus Steroid hormone receptor family member cnr14 homolog 0.00122045 1 0.5
Brugia malayi Nuclear hormone receptor family member nhr-25 0.00122045 1 1
Echinococcus granulosus FTZ F1 nuclear receptor protein 0.00122045 1 1
Onchocerca volvulus Bile acid receptor homolog 0.00122045 1 0.5
Loa Loa (eye worm) nuclear hormone receptor family member nhr-41 0.00122045 1 1
Schistosoma mansoni aminoadipate-semialdehyde dehydrogenase 0.0049 0.1562 0.2402
Trypanosoma brucei RNA helicase, putative 0.0167 0.6503 1
Brugia malayi Nuclear hormone receptor family member nhr-49 0.00122045 1 1
Echinococcus granulosus nuclear receptor 2DBD gamma 0.00122045 1 1
Wolbachia endosymbiont of Brugia malayi 4'-phosphopantetheinyl transferase 0.025 1 0.5
Leishmania major phosphopantetheinyl transferase-like protein 0.0049 0.1562 0.5
Echinococcus granulosus COUP TF:Svp nuclear hormone receptor 0.00122045 1 1
Echinococcus granulosus hepatocyte nuclear factor 4 alpha 0.00122045 1 1
Schistosoma mansoni coup transcription factor 0.00122045 1 1
Loa Loa (eye worm) nuclear hormone receptor family member nhr-1 0.00122045 1 1
Loa Loa (eye worm) nuclear hormone receptor family member nhr-14 0.00122045 1 1
Schistosoma mansoni thyroid hormone receptor 0.00122045 1 1
Echinococcus granulosus FTZ F1 alpha 0.00122045 1 1
Echinococcus multilocularis Nuclear hormone receptor family member nhr 41 0.00122045 1 1
Schistosoma mansoni photoreceptor-specific nuclear receptor related 0.00122045 1 1
Brugia malayi nuclear hormone receptor 0.00122045 1 1
Echinococcus multilocularis hepatocyte nuclear factor 4 alpha 0.00122045 1 1
Brugia malayi Nuclear hormone receptor family member nhr-19 0.00122045 1 1
Brugia malayi Nuclear hormone receptor family member nhr-3 0.00122045 1 1
Loa Loa (eye worm) hypothetical protein 0.00122045 1 1
Onchocerca volvulus 0.00122045 1 0.5
Echinococcus multilocularis L aminoadipate semialdehyde 0.0049 0.1562 1
Brugia malayi Nuclear hormone receptor family member nhr-31 0.00122045 1 1
Brugia malayi Steroid receptor seven-up type 2 0.00122045 1 1
Brugia malayi nuclear receptor NHR-88 0.00122045 1 1
Loa Loa (eye worm) hypothetical protein 0.00122045 1 1
Brugia malayi aminoadipate-semialdehyde dehydrogenase-phosphopantetheinyl transferase 0.0049 0.1562 1
Toxoplasma gondii 4'-phosphopantetheinyl transferase domain-containing protein 0.0049 0.1562 0.5
Loa Loa (eye worm) hypothetical protein 0.00122045 1 1
Schistosoma mansoni steroid hormone receptor ad4bp 0.00122045 1 1
Brugia malayi Nuclear hormone receptor family member nhr-1 0.00122045 1 1
Echinococcus granulosus ecdysone induced protein 78C 0.00122045 1 1
Brugia malayi Nuclear hormone receptor-like 1 0.00122045 1 1
Entamoeba histolytica hypothetical protein 0.0049 0.1562 0.5
Echinococcus granulosus L aminoadipate semialdehyde 0.0049 0.1562 1
Onchocerca volvulus Protein ultraspiracle homolog 0.00122045 1 0.5
Loa Loa (eye worm) steroid hormone receptor 0.00122045 1 1
Loa Loa (eye worm) hypothetical protein 0.00122045 1 1
Loa Loa (eye worm) hypothetical protein 0.0049 0.1562 1
Echinococcus multilocularis FTZ F1 nuclear receptor protein 0.00122045 1 1
Loa Loa (eye worm) nuclear hormone receptor family member nhr-31 0.00122045 1 1
Echinococcus granulosus Nuclear hormone receptor family member nhr 41 0.00122045 1 1
Echinococcus multilocularis thyroid hormone receptor alpha 0.00122045 1 1
Mycobacterium leprae HOLO-[ACYL-CARRIER PROTEIN] SYNTHASE ACPS (HOLO-ACP SYNTHASE) (CoA:APO-[ACP]PANTETHEINEPHOSPHOTRANSFERASE) (CoA:APO-[ACYL-CARRIE 0.02 0.7924 1
Schistosoma mansoni retinoic acid receptor RXR 0.00122045 1 1
Schistosoma mansoni RAR-like nuclear receptor 0.00122045 1 1
Loa Loa (eye worm) nuclear Hormone Receptor family member 0.00122045 1 1
Brugia malayi Nuclear hormone receptor family member nhr-19 0.00122045 1 1
Schistosoma mansoni nuclear hormone receptor 0.00122045 1 1
Mycobacterium tuberculosis holo-[acyl-carrier protein] synthase AcpS (holo-ACP synthase) (CoA:APO-[ACP]pantetheinephosphotransferase) (CoA:APO-[acyl-carrie 0.025 1 0.5
Echinococcus granulosus nuclear receptor 2DBD gamma 0.00122045 1 1
Brugia malayi Ligand-binding domain of nuclear hormone receptor family protein 0.00122045 1 1
Loa Loa (eye worm) hypothetical protein 0.00122045 1 1
Echinococcus granulosus retinoic acid receptor rxr beta a 0.00122045 1 1
Plasmodium falciparum holo-[acyl-carrier-protein] synthase, putative 0.025 1 0.5
Mycobacterium ulcerans 4'-phosphopantetheinyl transferase 0.025 1 1
Plasmodium vivax holo-[acyl-carrier-protein] synthase, putative 0.025 1 0.5
Schistosoma mansoni thyroid hormone receptor 0.00122045 1 1
Brugia malayi steroid hormone receptor 0.00122045 1 1
Brugia malayi Nuclear hormone receptor family member nhr-41 0.00122045 1 1
Schistosoma mansoni nuclear hormone receptor nor-1/nor-2 0.00122045 1 1
Onchocerca volvulus 0.0049 0.1562 1
Schistosoma mansoni hypothetical protein 0.0167 0.6503 1
Schistosoma mansoni Tr4/Tr2 (homologue) 0.00122045 1 1
Echinococcus multilocularis FTZ F1 alpha 0.00122045 1 1
Echinococcus multilocularis nuclear receptor 2DBD gamma 0.00122045 1 1
Loa Loa (eye worm) nuclear hormone receptor family member nhr-49 0.00122045 1 1
Brugia malayi Nuclear hormone receptor family member nhr-40 0.00122045 1 1
Echinococcus multilocularis COUP TF:Svp nuclear hormone receptor 0.00122045 1 1
Echinococcus multilocularis ecdysone induced protein 78C 0.00122045 1 1

Activities

Activity type Activity value Assay description Source Reference
Activity (functional) Antibacterial activity against Escherichia coli CECT 99 up to 40 ug/mL by broth microdilution method ChEMBL. 16038541
Activity (functional) Antifungal activity against Candida albicans UBC1 up to 40 ug/mL by broth microdilution method ChEMBL. 16038541
CD (binding) > 10 ug ml-1 Induction of NADPH:quinone reductase activity in mouse Hepa-1c1c7 cells assessed as drug level required to double specific enzyme activity ChEMBL. 14510596
EC50 (functional) = 0 uM Agonist activity at human FXR expressed in COS1 cells by luciferase reporter gene assay ChEMBL. 19911773
EC50 (functional) > 10 uM Agonist activity at TGR5 expressed in CHO cells by CRE-driven luciferase reporter gene assay ChEMBL. 19911773
ED50 (functional) = 0.35 uM Induction of melanogenesis in mouse B16 2F2 cells assessed as intracellular melanin content after 3 days ChEMBL. 12027734
Efficacy (functional) = 0 % Agonist activity at TGR5 expressed in CHO cells by CRE-driven luciferase reporter gene assay relative to litocholic acid ChEMBL. 19911773
IC50 (binding) = 2.1 ug ml-1 Antiviral activity against HIV1 Reverse transcriptase activity ChEMBL. 19515569
IC50 (functional) > 10 ug ml-1 Cytotoxicity against human HeLa cells after 48 hrs by MTT assay ChEMBL. 16038541
IC50 (functional) > 10 ug ml-1 Cytotoxicity against human Hep2 cells after 48 hrs by MTT assay ChEMBL. 16038541
IC50 (functional) > 0.4 uM Antiinflammatory activity against mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide release after 24 hrs ChEMBL. 20192236
IC50 (functional) = 4.7 uM Antiplasmodial activity against chloroquine- and pyrimethamine-resistant Plasmodium falciparum K1 infected in human red blood cells assessed as [3H]hypoxanthine incorporation after 48 hrs by liquid scintillation counting ChEMBL. 21438586
IC50 (functional) = 25.4 uM Growth inhibition of mouse B16 2F2 cells after 3 days ChEMBL. 12027734
IC50 (functional) = 38.5 uM Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced NO production incubated for 1 hr prior to LPS challenge measured after 24 hrs by Griess method ChEMBL. 24909081
IC50 (functional) > 90 uM Antiparasitic activity against Trypanosoma brucei rhodesiense STIB 900 bloodstream form after 72 hrs by microplate fluorimetry ChEMBL. 21438586
Inhibition (binding) = -2.4 % Inhibition of tyrosinase at 333 uM ChEMBL. 14510598

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Mus musculus ChEMBL23 20192236
Homo sapiens ChEMBL23 16038541
Plasmodium falciparum 21438586

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

3 literature references were collected for this gene.

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