Detailed information for compound 411874

Basic information

Technical information
  • TDR Targets ID: 411874
  • Name: 2-prop-1-en-2-yl-2,3-dihydrobenzo[f][1]benzof uran-4,9-dione
  • MW: 240.254 | Formula: C15H12O3
  • H donors: 0 H acceptors: 2 LogP: 2.98 Rotable bonds: 1
    Rule of 5 violations (Lipinski): 1
  • SMILES: CC(=C)C1CC2=C(O1)C(=O)c1c(C2=O)cccc1
  • InChi: 1S/C15H12O3/c1-8(2)12-7-11-13(16)9-5-3-4-6-10(9)14(17)15(11)18-12/h3-6,12H,1,7H2,2H3
  • InChiKey: ZDMOREUAQLXRCQ-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 2-isopropenyl-2,3-dihydrobenzo[f]benzofuran-4,9-dione
  • 2-isopropenyl-2,3-dihydrobenzo[f]benzofuran-4,9-quinone
  • 2-prop-1-en-2-yl-2,3-dihydrobenzo[f][1]benzoxole-4,9-dione
  • 51920-95-7
  • Dehydro iso-.alpha.-lapachone
  • Dehydroiso-alpha-lapachone
  • 2-Isopropenyl-2,3-dihydronaphtho[2,3-b]furan-4,9-dione
  • AIDS-057047
  • AIDS057047
  • NCI60_009666
  • NSC629754

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
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0782 0.3153 1
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0782 0.3153 1
Plasmodium falciparum cysteine proteinase falcipain 2b 0.0782 0.3153 1
Echinococcus granulosus cathepsin b 0.1561 1 1
Trichomonas vaginalis Clan CA, family C1, cathepsin B-like cysteine peptidase 0.0607 0.1608 0.5099
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0782 0.3153 1
Loa Loa (eye worm) Papain cysteine protease/cathepsin propeptide inhibitor-containing protein 0.0782 0.3153 0.239
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0782 0.3153 1
Entamoeba histolytica cysteine proteinase, putative 0.0782 0.3153 1
Loa Loa (eye worm) cysteine protease 0.0782 0.3153 0.239
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0782 0.3153 1
Toxoplasma gondii cathepsin CPL 0.0782 0.3153 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0782 0.3153 1
Schistosoma mansoni cathepsin B-like peptidase (C01 family) 0.1561 1 1
Leishmania major cathepsin L-like protease 0.0782 0.3153 1
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0782 0.3153 1
Loa Loa (eye worm) ctsf protein 0.0782 0.3153 0.239
Schistosoma mansoni cathepsin B-like peptidase (C01 family) 0.1561 1 1
Entamoeba histolytica cysteine proteinase, putative 0.0782 0.3153 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0782 0.3153 1
Plasmodium vivax vivapain-2 0.0782 0.3153 1
Giardia lamblia Cathepsin B precursor 0.0607 0.1608 0.5
Leishmania major cathepsin L-like protease 0.0782 0.3153 1
Schistosoma mansoni cathepsin F (C01 family) 0.0782 0.3153 0.3153
Brugia malayi Cathepsin L-like precursor 0.0782 0.3153 0.3153
Echinococcus multilocularis cathepsin l cysteine peptidase 0.0782 0.3153 0.3153
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0782 0.3153 1
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0782 0.3153 1
Brugia malayi Papain family cysteine protease containing protein 0.0782 0.3153 0.3153
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0782 0.3153 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0782 0.3153 1
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0782 0.3153 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0782 0.3153 1
Loa Loa (eye worm) cathepsin B 0.0607 0.1608 0.0672
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0782 0.3153 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L or K-like cysteine peptidase 0.0782 0.3153 1
Onchocerca volvulus 0.0782 0.3153 1
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0782 0.3153 1
Echinococcus multilocularis cathepsin L cysteine protease 0.0782 0.3153 0.3153
Trypanosoma cruzi cysteine peptidase C (CPC), putative 0.1561 1 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0538 0.1003 0.3182
Brugia malayi Cathepsin L-like cysteine proteinase 0.0538 0.1003 0.1003
Echinococcus multilocularis cysteine protease 0.0782 0.3153 0.3153
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0782 0.3153 1
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0782 0.3153 1
Leishmania major cathepsin L-like protease 0.0782 0.3153 1
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0782 0.3153 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0782 0.3153 1
Echinococcus multilocularis cathepsin L cysteine protease 0.0782 0.3153 0.3153
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0782 0.3153 1
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0782 0.3153 1
Giardia lamblia Cathepsin B precursor 0.0607 0.1608 0.5
Onchocerca volvulus Cathepsin L homolog 0.0782 0.3153 1
Brugia malayi Cathepsin L-like precursor 0.0538 0.1003 0.1003
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0782 0.3153 1
Entamoeba histolytica cysteine protease, putative 0.0782 0.3153 1
Loa Loa (eye worm) hypothetical protein 0.1561 1 1
Echinococcus multilocularis cathepsin b 0.1561 1 1
Trypanosoma cruzi cysteine peptidase, putative 0.0782 0.3153 0.3153
Leishmania major cathepsin L-like protease 0.0782 0.3153 1
Trypanosoma cruzi cysteine peptidase, putative 0.0782 0.3153 0.3153
Loa Loa (eye worm) hypothetical protein 0.0782 0.3153 0.239
Echinococcus granulosus cathepsin l cysteine peptidase 0.0782 0.3153 0.3153
Schistosoma mansoni cathepsin B-like peptidase (C01 family) 0.0607 0.1608 0.1608
Trypanosoma cruzi cruzipain precursor, putative 0.0782 0.3153 0.3153
Onchocerca volvulus 0.0782 0.3153 1
Onchocerca volvulus 0.0782 0.3153 1
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0782 0.3153 1
Leishmania major cathepsin L-like protease 0.0782 0.3153 1
Onchocerca volvulus Cathepsin L homolog 0.0782 0.3153 1
Brugia malayi Cathepsin L-like precursor 0.0782 0.3153 0.3153
Brugia malayi Cathepsin L-like precursor 0.0782 0.3153 0.3153
Brugia malayi Cathepsin L-like precursor 0.0782 0.3153 0.3153
Leishmania major cathepsin L-like protease 0.0782 0.3153 1
Trypanosoma cruzi cysteine peptidase, putative 0.0782 0.3153 0.3153
Onchocerca volvulus 0.0782 0.3153 1
Plasmodium falciparum cysteine proteinase falcipain 2a 0.0782 0.3153 1
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0782 0.3153 1
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0782 0.3153 1
Plasmodium vivax vivapain-2 0.0782 0.3153 1
Echinococcus multilocularis cysteine protease 0.0782 0.3153 0.3153
Schistosoma mansoni SmCB2 peptidase (C01 family) 0.1561 1 1
Onchocerca volvulus Cathepsin F homolog 0.0782 0.3153 1
Schistosoma mansoni cathepsin B-like peptidase (C01 family) 0.1561 1 1
Schistosoma mansoni cathepsin F (C01 family) 0.0538 0.1003 0.1003
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0782 0.3153 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0538 0.1003 0.3182
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0782 0.3153 1
Echinococcus granulosus cathepsin b 0.1561 1 1
Trypanosoma cruzi cysteine peptidase C (CPC), putative 0.0607 0.1608 0.1608
Schistosoma mansoni cathepsin F (C01 family) 0.0782 0.3153 0.3153
Trypanosoma cruzi cysteine peptidase, putative 0.0782 0.3153 0.3153
Plasmodium falciparum cysteine proteinase falcipain 3 0.0782 0.3153 1
Leishmania major cathepsin L-like protease 0.0782 0.3153 1
Echinococcus granulosus cathepsin L cysteine proteinase 0.0782 0.3153 0.3153
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0782 0.3153 1
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0782 0.3153 1
Onchocerca volvulus 0.0782 0.3153 1
Brugia malayi Cathepsin L-like precursor 0.0782 0.3153 0.3153
Trichomonas vaginalis Clan CA, family C1, cathepsin L-like cysteine peptidase 0.0782 0.3153 1
Trypanosoma brucei cysteine peptidase C (CPC) 0.0607 0.1608 0.5099
Trypanosoma cruzi cysteine peptidase, clan CA, family C1, cathepsin L-like, putative 0.0538 0.1003 0.1003
Brugia malayi Cathepsin L-like precursor 0.0782 0.3153 0.3153
Leishmania major cysteine peptidase A (CPA) 0.0782 0.3153 1
Entamoeba histolytica cysteine proteinase, putative 0.0538 0.1003 0.3182
Echinococcus granulosus cathepsin l1 0.0538 0.1003 0.1003
Echinococcus multilocularis cathepsin l cysteine peptidase 0.0782 0.3153 0.3153
Echinococcus granulosus cathepsin l1 0.0782 0.3153 0.3153
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0782 0.3153 1
Brugia malayi cathepsin L-like precursor 0.0538 0.1003 0.1003
Trichomonas vaginalis Clan CA, family C1, papain-like cysteine peptidase 0.0782 0.3153 1
Onchocerca volvulus 0.0782 0.3153 1
Giardia lamblia Cathepsin B precursor 0.0607 0.1608 0.5
Loa Loa (eye worm) fibroinase 0.0782 0.3153 0.239
Onchocerca volvulus 0.0782 0.3153 1
Trichomonas vaginalis Clan CA, family C1, cathepsin L or K-like cysteine peptidase 0.0782 0.3153 1
Loa Loa (eye worm) papain family cysteine protease containing protein 0.0782 0.3153 0.239
Leishmania major cathepsin L-like protease 0.0782 0.3153 1
Trypanosoma brucei cysteine peptidase, Clan CA, family C1, Cathepsin L-like 0.0782 0.3153 1
Brugia malayi Cathepsin L-like precursor 0.0538 0.1003 0.1003
Echinococcus multilocularis cathepsin b 0.1561 1 1

Activities

Activity type Activity value Assay description Source Reference
ED50 (functional) = 0.2 ug ml-1 Cytotoxicity against human Col2 cells ChEMBL. 10785421
ED50 (functional) = 0.2 ug ml-1 Cytotoxicity against human KB cells ChEMBL. 10785421
ED50 (functional) = 0.2 ug ml-1 Cytotoxicity against human LNCaP cells ChEMBL. 10785421
ED50 (functional) = 0.2 ug ml-1 Cytotoxicity against human SK-N-SH cells ChEMBL. 10785421
ED50 (functional) = 0.3 ug ml-1 Cytotoxicity against human SW626 cells ChEMBL. 10785421
ED50 (functional) = 0.4 ug ml-1 Cytotoxicity against human M109 cells ChEMBL. 10785421
GI50 (functional) -5.471 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the HL-60(TB) Leukemia cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4.853 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the SK-MEL-5 Melanoma cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4.787 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the HOP-92 Non-Small Cell Lung cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4.732 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the SF-539 Central Nervous System cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4.724 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the NCI-H23 Non-Small Cell Lung cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4.719 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the SN12C Renal cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) = 1.9 uM Growth inhibition of human SW1573 cells after 48 hrs by sulforhodamine B assay ChEMBL. 20304655
GI50 (functional) = 2.1 uM Growth inhibition of human HeLa cells after 48 hrs by sulforhodamine B assay ChEMBL. 20304655
GI50 (functional) = 2.3 uM Growth inhibition of human HBL100 cells after 48 hrs by sulforhodamine B assay ChEMBL. 20304655
GI50 (functional) = 2.6 uM Growth inhibition of human A2780 cells after 48 hrs by sulforhodamine B assay ChEMBL. 20304655
GI50 (functional) = 2.7 uM Growth inhibition of human WiDr cells after 48 hrs by sulforhodamine B assay ChEMBL. 20304655
GI50 (functional) = 21 uM Growth inhibition of human T47D cells after 48 hrs by sulforhodamine B assay ChEMBL. 20304655
IC50 (functional) = 11.67 nM Anticancer activity against human DU145 cells after 72 hrs by XTT assay ChEMBL. 18829316
IC50 (functional) = 1.2 uM Cytotoxicity against human MCF7 cells after 3 days by SRB assay ChEMBL. 15217280
IC50 (ADMET) = 1.46 uM Cytotoxicity against human promyelocytic leukemia HL60 cell line by MTT assay ChEMBL. 17249647
IC50 (ADMET) = 1.46 uM Cytotoxicity against human promyelocytic leukemia HL60 cell line by MTT assay ChEMBL. 17249647
IC50 (functional) = 2.6 uM Cytotoxicity against human 1A9 cells after 3 days by SRB assay ChEMBL. 15217280
IC50 (functional) = 2.8 uM Cytotoxicity against paclitaxel-resistant human 1A9 cells after 3 days by SRB assay ChEMBL. 15217280
IC50 (functional) = 3.2 uM Cytotoxicity against camptothecin-resistant human KB cells after 3 days by SRB assay ChEMBL. 15217280
IC50 (functional) = 3.5 uM Cytotoxicity against etoposide-resistant human KB cells after 3 days by SRB assay ChEMBL. 15217280
IC50 (functional) = 4 uM Cytotoxicity against human HOS cells after 3 days by SRB assay ChEMBL. 15217280
IC50 (functional) = 4.1 uM Cytotoxicity against human KB cells after 3 days by SRB assay ChEMBL. 15217280
IC50 (ADMET) = 4.3 uM Antiproliferative activity against human HaCaT cells ChEMBL. 10479319
IC50 (functional) = 6.4 uM Cytotoxicity against human A549 cells after 3 days by SRB assay ChEMBL. 15217280
IC50 (functional) > 10 uM Cytotoxicity against human Caki1 cells after 3 days by SRB assay ChEMBL. 15217280
Inhibition (functional) = 26 % Cytotoxicity against human Caki1 cells at 10 uM after 3 days by SRB assay ChEMBL. 15217280
Inhibition (functional) = 100 % Anticancer activity against human DU145 cells after 72 hrs 25 ug/ml by XTT assay ChEMBL. 18829316
LogP = 3.4 Partition coefficient, log P of the compound ChEMBL. 17249647
MBC (functional) = 81.38 uM Antimycobacterial activity against Mycobacterium tuberculosis by Bactec TB-460 assay ChEMBL. No reference
MIC (functional) > 78.12 ug ml-1 Antibacterial activity against Escherichia coli after 24 hr by p-iodonitrotetrazolium assay ChEMBL. No reference
MIC (functional) = 40.67 uM Antimycobacterial activity against Mycobacterium tuberculosis by Bactec TB-460 assay ChEMBL. No reference

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Homo sapiens ChEMBL23 10479319

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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