Detailed information for compound 503020

Basic information

Technical information
  • TDR Targets ID: 503020
  • Name: caryophyllene oxide
  • MW: 220.35 | Formula: C15H24O
  • H donors: 0 H acceptors: 0 LogP: 3.56 Rotable bonds: 0
    Rule of 5 violations (Lipinski): 1
  • SMILES: C=C1CC[C@@H]2O[C@@]2(CC[C@@H]2[C@@H]1CC2(C)C)C
  • InChi: 1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3/t11-,12-,13+,15-/m1/s1
  • InChiKey: NVEQFIOZRFFVFW-GUIRCDHDSA-N  


Substructure search Similarity search

Network

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Synonyms

  • ZINC02083321
  • (-)-Caryophyllene oxide

Targets

Known targets for this compound

No curated genes were found associated with this compound

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 fructose bisphosphate aldolase class I 0.0104357 0.404212 0.391202
Plasmodium falciparum fructose-bisphosphate aldolase 0.0104357 0.404212 0.5055
Loa Loa (eye worm) TK/INSR protein kinase 0.00569312 0.0213705 0.0213705
Mycobacterium ulcerans formate dehydrogenase H FdhF 0.0153341 0.799627 0.5
Echinococcus multilocularis epidermal growth factor receptor 0.0178163 1 1
Brugia malayi FAD binding domain containing protein 0.0153341 0.799627 0.799627
Loa Loa (eye worm) TK/EGFR protein kinase 0.0178163 1 1
Loa Loa (eye worm) FAD binding domain-containing protein 0.0099057 0.361427 0.361427
Trypanosoma cruzi fructose-bisphosphate aldolase, glycosomal, putative 0.0104357 0.404212 0.5055
Leishmania major cytochrome P450 reductase, putative 0.0140681 0.697431 0.872195
Echinococcus multilocularis epidermal growth factor receptor 0.00957253 0.334532 0.329872
Trypanosoma cruzi cytochrome P450 reductase, putative 0.0153341 0.799627 1
Brugia malayi fructose-bisphosphate aldolase 2 0.0104357 0.404212 0.404212
Schistosoma mansoni tyrosine kinase 0.0178163 1 1
Trypanosoma cruzi fructose-bisphosphate aldolase, glycosomal, putative 0.0104357 0.404212 0.5055
Loa Loa (eye worm) hypothetical protein 0.0153341 0.799627 0.799627
Echinococcus granulosus fructose 16 bisphosphate aldolase 0.0104357 0.404212 0.391202
Toxoplasma gondii fructose-1,6-bisphosphate aldolase 0.0104357 0.404212 1
Entamoeba histolytica type A flavoprotein, putative 0.00542838 0 0.5
Plasmodium falciparum nitric oxide synthase, putative 0.0153341 0.799627 1
Echinococcus multilocularis fructose 1,6 bisphosphate aldolase 0.0104357 0.404212 0.40004
Giardia lamblia Nitric oxide synthase, inducible 0.0140681 0.697431 0.5
Brugia malayi flavodoxin family protein 0.0153341 0.799627 0.799627
Entamoeba histolytica type A flavoprotein, putative 0.00542838 0 0.5
Giardia lamblia Hypothetical protein 0.0140681 0.697431 0.5
Echinococcus granulosus melanoma receptor tyrosine protein kinase 0.00957253 0.334532 0.32
Schistosoma mansoni tyrosine kinase 0.00957253 0.334532 0.32
Echinococcus multilocularis insulin receptor 0.00569312 0.0213705 0.0145169
Echinococcus multilocularis fructose 1,6 bisphosphate aldolase 0.0104357 0.404212 0.40004
Echinococcus multilocularis methionine synthase reductase 0.0099057 0.361427 0.356955
Trypanosoma cruzi cytochrome P450 reductase, putative 0.0153341 0.799627 1
Trypanosoma cruzi p450 reductase, putative 0.0153341 0.799627 1
Echinococcus granulosus fructose 16 bisphosphate aldolase 0.0104357 0.404212 0.391202
Echinococcus granulosus NADPH dependent diflavin oxidoreductase 1 0.0153341 0.799627 0.795252
Plasmodium vivax fructose 1,6-bisphosphate aldolase, putative 0.0104357 0.404212 0.5055
Echinococcus multilocularis fructose 1,6 bisphosphate aldolase 0.0104357 0.404212 0.40004
Echinococcus granulosus NADPH cytochrome P450 reductase 0.0153341 0.799627 0.795252
Schistosoma mansoni NADPH flavin oxidoreductase 0.0086397 0.25923 0.243054
Loa Loa (eye worm) fructose-bisphosphate aldolase 2 0.0104357 0.404212 0.404212
Loa Loa (eye worm) FAD binding domain-containing protein 0.0153341 0.799627 0.799627
Echinococcus granulosus epidermal growth factor receptor 0.0178163 1 1
Trichomonas vaginalis sulfite reductase, putative 0.0153341 0.799627 1
Leishmania major p450 reductase, putative 0.0153341 0.799627 1
Trypanosoma brucei NADPH-dependent diflavin oxidoreductase 1 0.0153341 0.799627 1
Loa Loa (eye worm) fructose-bisphosphate aldolase 1 0.0104357 0.404212 0.404212
Echinococcus granulosus methionine synthase reductase 0.0099057 0.361427 0.347482
Echinococcus multilocularis NADPH cytochrome P450 reductase 0.0153341 0.799627 0.798224
Schistosoma mansoni tyrosine kinase 0.00947154 0.326379 0.311669
Trypanosoma cruzi fructose-bisphosphate aldolase, glycosomal, putative 0.0104357 0.404212 0.5055
Echinococcus granulosus epidermal growth factor receptor 0.00957253 0.334532 0.32
Schistosoma mansoni cytochrome P450 reductase 0.0153341 0.799627 0.795252
Trypanosoma cruzi fructose-bisphosphate aldolase, glycosomal, putative 0.0104357 0.404212 0.5055
Leishmania major NADPH-cytochrome p450 reductase-like protein 0.0153341 0.799627 1
Chlamydia trachomatis sulfite reductase 0.0099057 0.361427 0.5
Trypanosoma brucei NADPH--cytochrome P450 reductase, putative 0.0153341 0.799627 1
Schistosoma mansoni diflavin oxidoreductase 0.00669439 0.102197 0.0825912
Trypanosoma brucei NADPH--cytochrome P450 reductase, putative 0.0153341 0.799627 1
Treponema pallidum flavodoxin 0.00542838 0 0.5
Plasmodium vivax flavodoxin domain containing protein 0.0140681 0.697431 0.872195
Toxoplasma gondii fructose-bisphosphate aldolase, putative 0.0104357 0.404212 1
Entamoeba histolytica type A flavoprotein, putative 0.00542838 0 0.5
Schistosoma mansoni tyrosine kinase 0.00947154 0.326379 0.311669
Plasmodium vivax NADPH-cytochrome p450 reductase, putative 0.0153341 0.799627 1
Echinococcus multilocularis insulin growth factor 1 receptor beta 0.00569312 0.0213705 0.0145169
Schistosoma mansoni tyrosine kinase 0.00957253 0.334532 0.32
Entamoeba histolytica type A flavoprotein, putative 0.00542838 0 0.5
Brugia malayi fructose-bisphosphate aldolase 1 0.0104357 0.404212 0.404212
Brugia malayi Furin-like cysteine rich region family protein 0.0178163 1 1
Schistosoma mansoni 5-methyl tetrahydrofolate-homocysteine methyltransferase reductase 0.0099057 0.361427 0.347482
Trypanosoma cruzi NADPH-dependent FMN/FAD containing oxidoreductase, putative 0.0153341 0.799627 1
Leishmania major fructose-1,6-bisphosphate aldolase 0.0104357 0.404212 0.5055
Schistosoma mansoni fructose 16-bisphosphate aldolase 0.0104357 0.404212 0.391202
Entamoeba histolytica type A flavoprotein, putative 0.00542838 0 0.5
Schistosoma mansoni fructose 16-bisphosphate aldolase 0.0104357 0.404212 0.391202
Brugia malayi Protein kinase domain containing protein 0.00569312 0.0213705 0.0213705
Trypanosoma brucei NADPH-cytochrome p450 reductase, putative 0.0153341 0.799627 1
Brugia malayi FAD binding domain containing protein 0.0099057 0.361427 0.361427
Trypanosoma brucei fructose-bisphosphate aldolase, glycosomal, putative 0.0104357 0.404212 0.5055
Echinococcus granulosus fructose 16 bisphosphate aldolase 0.0104357 0.404212 0.391202
Toxoplasma gondii fructose-1,6-bisphosphate aldolase 0.0104357 0.404212 1
Trichomonas vaginalis NADPH fad oxidoreductase, putative 0.0140681 0.697431 0.872195
Echinococcus multilocularis NADPH dependent diflavin oxidoreductase 1 0.0153341 0.799627 0.798224
Schistosoma mansoni tyrosine kinase 0.00947154 0.326379 0.311669
Echinococcus multilocularis fructose bisphosphate aldolase class I 0.0104357 0.404212 0.40004

Activities

Activity type Activity value Assay description Source Reference
Activity (functional) Antituberculosis activity against Mycobacterium tuberculosis H37Ra by microplate alamar blue assay ChEMBL. 17845001
Activity (functional) 0 Antituberculosis activity against Mycobacterium tuberculosis H37Ra by microplate alamar blue assay ChEMBL. 17845001
Activity (functional) = 0.59 micromol/min Induction of cytosolic Glutathione S-transferase activity per mg of protein in A/J mouse forestomach at 20 mg, po for once every 2 days for total three doses measured after 24 hrs of last dose ChEMBL. 1402962
Activity (functional) = 1.2 micromol/min Induction of cytosolic Glutathione S-transferase activity per mg of protein in A/J mouse small bowel mucosa at 20 mg, po for once every 2 days for total three doses measured after 24 hrs of last dose ChEMBL. 1402962
Activity (functional) = 2.13 micromol/min Induction of cytosolic Glutathione S-transferase activity per mg of protein in A/J mouse liver at 20 mg, po for once every 2 days for total three doses measured after 24 hrs of last dose ChEMBL. 1402962
ED50 (functional) > 20 ug ml-1 Cytotoxicity against human A431 cells ChEMBL. 1517737
ED50 (functional) > 20 ug ml-1 Cytotoxicity against human Col2 cells ChEMBL. 1517737
ED50 (functional) > 20 ug ml-1 Cytotoxicity against human HT1080 cells ChEMBL. 1517737
ED50 (functional) > 20 ug ml-1 Cytotoxicity against mouse P388 cells ChEMBL. 1517737
ED50 (functional) > 20 ug ml-1 Cytotoxicity against human ZR-75-1 cells ChEMBL. 1517737
ED50 (functional) > 20 ug ml-1 Cytotoxicity against human SK-MEL-2 cells ChEMBL. 1517737
ED50 (functional) > 20 ug ml-1 Cytotoxicity against human Lu1 cells ChEMBL. 1517737
ED50 (functional) > 20 ug ml-1 Cytotoxicity against human LNCAP cells ChEMBL. 1517737
ED50 (functional) > 20 ug ml-1 Cytotoxicity against human KB cells ChEMBL. 1517737
IC50 (functional) = 2.8 ug ml-1 Antimalarial activity against multidrug-resistant Plasmodium falciparum K1 assessed as uptake of [3H]-hypoxanthine by microculture radioisotope technique ChEMBL. 17845001
IC50 (functional) = 2.8 ug ml-1 Antimalarial activity against multidrug-resistant Plasmodium falciparum K1 assessed as uptake of [3H]-hypoxanthine by microculture radioisotope technique ChEMBL. 17845001
IC50 (functional) > 5 ug ml-1 Cytotoxicity against human KB cells ChEMBL. 17845001
IC50 (functional) > 5 ug ml-1 Cytotoxicity against human BC1 cells ChEMBL. 17845001
IC50 (functional) > 5 ug ml-1 Cytotoxicity against human KB cells ChEMBL. 17845001
IC50 (functional) = 19.5 ug ml-1 Cytotoxicity against human NCI-H187 cells ChEMBL. 17845001
IC50 (functional) = 19.5 ug ml-1 Cytotoxicity against human NCI-H187 cells ChEMBL. 17845001
IC50 (functional) > 25 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) > 90 uM Antiparasitic activity against Trypanosoma brucei rhodesiense STIB 900 bloodstream form after 72 hrs by microplate fluorimetry ChEMBL. 21438586
IC50 (binding) = 208.4 uM Inhibition of horse serum BuChE by Ellman's method ChEMBL. 17067156
Inhibition (binding) = -12.83 % Inhibition of electric eel AChE at 2 mg/ml by Ellman's method ChEMBL. 23062825
Inhibition (binding) = 1.64 % Inhibition of horse BChE at 2 mg/ml by Ellman's method ChEMBL. 23062825

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Homo sapiens ChEMBL23 17845001
Plasmodium falciparum ChEMBL23 17845001

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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