Detailed information for compound 209827

Basic information

Technical information
  • TDR Targets ID: 209827
  • Name: 2-hydroxycyclohepta-2,4,6-trien-1-one
  • MW: 122.121 | Formula: C7H6O2
  • H donors: 1 H acceptors: 2 LogP: 1.45 Rotable bonds: 0
    Rule of 5 violations (Lipinski): 1
  • SMILES: Oc1cccccc1=O
  • InChi: 1S/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9)
  • InChiKey: MDYOLVRUBBJPFM-UHFFFAOYSA-N  


Substructure search Similarity search

Network

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Synonyms

  • 2-hydroxy-1-cyclohepta-2,4,6-trienone
  • Tropolone
  • 533-75-5
  • C15474
  • AIDS-228516
  • AIDS228516
  • NSC89303
  • 2-Hydroxy-2,4,6-cycloheptatrien-1-one
  • 93555_FLUKA
  • InChI=1/C7H6O2/c8-6-4-2-1-3-5-7(6)9/h1-5H,(H,8,9
  • ZINC00392003
  • NCIMech_000829
  • NCI60_041986
  • T89702_ALDRICH
  • 2,4,6-Cycloheptatrien-1-one, 2-hydroxy-
  • 2-Hydroxycyclohepta-2,4,6-trienone
  • 2-Hydroxytropone
  • 4-08-00-00159 (Beilstein Handbook Reference)
  • BRN 1904978
  • CCRIS 6609
  • CI TROPOLONE 8
  • EINECS 208-577-2
  • NSC 89303
  • Purpurocatechol

Targets

Known targets for this compound

Species Target name Source Bibliographic reference
Agaricus bisporus Tyrosinase Starlite/ChEMBL References
Homo sapiens jun proto-oncogene Starlite/ChEMBL No references
Homo sapiens nuclear factor of kappa light polypeptide gene enhancer in B-cells 1 Starlite/ChEMBL No references
Bos taurus Carboxypeptidase A1 Starlite/ChEMBL References
Homo sapiens dopamine beta-hydroxylase (dopamine beta-monooxygenase) Starlite/ChEMBL References

Predicted pathogen targets for this compound

By orthology
Species Potential target Known druggable target/s Ortholog Group
Echinococcus multilocularis jun protein Get druggable targets OG5_131442 All targets in OG5_131442
Echinococcus granulosus jun protein Get druggable targets OG5_131442 All targets in OG5_131442
Schistosoma japonicum ko:K00503 dopamine beta-monooxygenase [EC1.14.17.1], putative Get druggable targets OG5_129281 All targets in OG5_129281
Loa Loa (eye worm) hypothetical protein Get druggable targets OG5_131442 All targets in OG5_131442
Brugia malayi bZIP transcription factor family protein Get druggable targets OG5_131442 All targets in OG5_131442
Schistosoma mansoni dopamine-beta-monooxygenase Get druggable targets OG5_129281 All targets in OG5_129281
Echinococcus multilocularis Basic leucine zipper (bZIP) transcription factor Get druggable targets OG5_131442 All targets in OG5_131442
Echinococcus granulosus Basic leucine zipper bZIP transcription factor Get druggable targets OG5_131442 All targets in OG5_131442
By sequence similarity to non orthologous known druggable targets
Species Potential target Known druggable target Length Alignment span Identity
Candida albicans potential zinc carboxypeptidase similar to S. cerevisiae ECM14 Carboxypeptidase A1   419 aa 361 aa 28.0 %
Schistosoma japonicum ko:K01290 carboxypeptidase A [EC3.4.17.1], putative Carboxypeptidase A1   419 aa 423 aa 31.7 %
Onchocerca volvulus Replication factor C subunit 1 homolog Carboxypeptidase A1   419 aa 441 aa 33.8 %
Onchocerca volvulus Vacuolar protein sorting-associated protein 51 homolog Carboxypeptidase A1   419 aa 427 aa 34.0 %
Echinococcus granulosus subfamily M14A unassigned peptidase Carboxypeptidase A1   419 aa 403 aa 32.3 %
Onchocerca volvulus Carboxypeptidase A1   419 aa 422 aa 36.3 %
Onchocerca volvulus Carboxypeptidase A1   419 aa 448 aa 29.7 %
Candida albicans potential zinc carboxypeptidase similar to S. cerevisiae ECM14 Carboxypeptidase A1   419 aa 361 aa 28.0 %
Echinococcus multilocularis subfamily M14A unassigned peptidase Carboxypeptidase A1   419 aa 422 aa 31.3 %
Onchocerca volvulus Carboxypeptidase A1   419 aa 439 aa 30.5 %
Drosophila melanogaster CG4017 gene product from transcript CG4017-RA Carboxypeptidase A1   419 aa 417 aa 35.5 %
Obtained from network model

Ranking Plot

Putative Targets List

Species Potential target Raw Global Species
Loa Loa (eye worm) hypothetical protein 0.0149 0.4751 1
Brugia malayi Copper type II ascorbate-dependent monooxygenase, C-terminal domain containing protein 0.0149 0.4751 1
Loa Loa (eye worm) ShTK domain-containing protein 0.0111 0.3248 0.6837
Brugia malayi Hypothetical tyrosinase-like protein C02C2.1 in chromosome III 0.0111 0.3248 0.6837
Brugia malayi ShTK domain containing protein 0.0111 0.3248 0.6837
Brugia malayi Copper type II ascorbate-dependent monooxygenase, C-terminal domain containing protein 0.0074 0.1769 0.3724
Schistosoma mansoni tyrosinase precursor 0.0111 0.3248 0.2001
Echinococcus multilocularis nuclear factor of activated T cells 5 0.0089 0.2375 0.2556
Onchocerca volvulus 0.0111 0.3248 1
Schistosoma mansoni tyrosinase precursor 0.0111 0.3248 0.2001
Schistosoma mansoni peptidylglycine monooxygenase 0.0149 0.4751 0.3781
Loa Loa (eye worm) hypothetical protein 0.0149 0.4751 1
Loa Loa (eye worm) hypothetical protein 0.0111 0.3248 0.6837
Schistosoma mansoni peptidyl-glycine monooxygenase 0.0149 0.4751 0.3781
Loa Loa (eye worm) hypothetical protein 0.0056 0.1099 0.2313
Brugia malayi Hypothetical tyrosinase-like protein F21C3.2 in chromosome I 0.0111 0.3248 0.6837
Onchocerca volvulus 0.0111 0.3248 1
Onchocerca volvulus 0.0068 0.156 0.4801
Echinococcus granulosus Basic leucine zipper bZIP transcription factor 0.0101 0.2866 0.4095
Loa Loa (eye worm) hypothetical protein 0.0111 0.3248 0.6837
Onchocerca volvulus 0.0068 0.156 0.4801
Onchocerca volvulus Subfamily M14A unassigned peptidase homolog 0.0068 0.156 0.4801
Brugia malayi Common central domain of tyrosinase family protein 0.0111 0.3248 0.6837
Brugia malayi hypothetical protein 0.008 0.2009 0.4229
Echinococcus multilocularis jun protein 0.0101 0.2866 0.4095
Brugia malayi Hypothetical tyrosinase-like protein C02C2.1 in chromosome III 0.0111 0.3248 0.6837
Schistosoma mansoni hypothetical protein 0.0082 0.2119 0.0662
Onchocerca volvulus 0.0068 0.156 0.4801
Schistosoma mansoni jun-related protein 0.0082 0.2119 0.0662
Brugia malayi Copper type II ascorbate-dependent monooxygenase, C-terminal domain containing protein 0.0149 0.4751 1
Loa Loa (eye worm) hypothetical protein 0.0099 0.2757 0.5803
Onchocerca volvulus 0.008 0.2009 0.6186
Brugia malayi bZIP transcription factor family protein 0.0101 0.2866 0.6034
Loa Loa (eye worm) tyrosinase 1 0.0111 0.3248 0.6837
Onchocerca volvulus 0.0111 0.3248 1
Echinococcus granulosus peptidyl glycine alpha amidating monooxygenase 0.0149 0.4751 1
Echinococcus granulosus jun protein 0.0101 0.2866 0.4095
Brugia malayi Hypothetical tyrosinase-like protein C02C2.1 in chromosome III 0.0111 0.3248 0.6837
Loa Loa (eye worm) ShTK domain-containing protein 0.0111 0.3248 0.6837
Brugia malayi Copper type II ascorbate-dependent monooxygenase, N-terminal domain containing protein 0.0076 0.1857 0.3908
Echinococcus granulosus nuclear factor of activated T cells 5 0.0089 0.2375 0.2556
Echinococcus multilocularis peptidyl glycine alpha amidating monooxygenase 0.0149 0.4751 1
Onchocerca volvulus 0.0068 0.156 0.4801
Onchocerca volvulus 0.0111 0.3248 1
Echinococcus multilocularis Basic leucine zipper (bZIP) transcription factor 0.0101 0.2866 0.4095

Activities

Activity type Activity value Assay description Source Reference
EC50 (functional) > 10 uM Neuroprotective activity against glutamate-mediated oxidative stress-induced cell death in mouse HT22 cells assessed as survival after 24 hrs by MTT assay ChEMBL. 20045220
GI50 (functional) -4.923 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) -4.452 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the K-562 Leukemia cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4.096 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the UO-31 Renal cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4.081 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 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the MDA-N Breast cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the ACHN Renal cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4 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 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 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the DU-145 Prostate cell line. (Class of assay: confirmatory) ChEMBL. No reference
GI50 (functional) -4 PUBCHEM_BIOASSAY: NCI human tumor cell line growth inhibition assay. Data for the MALME-3M Melanoma cell line. (Class of assay: confirmatory) ChEMBL. No reference
IC50 (binding) = 4.68 10'-5M Inhibition of Clostridium histolyticum collagenase after 15 min ChEMBL. 14519960
IC50 (binding) = 7.11 10'-5M Inhibition of Bacillus thermoproteolyticus thermolysin after 15 min ChEMBL. 14519960
IC50 (binding) = 400 nM Inhibition of mushroom tyrosinase assessed as L-DOPA conversion to melanin preincubated for 10 mins prior to substrate addition measured after 10 mins by spectrophotometric analysis ChEMBL. 24074025
IC50 (functional) = 0.3 ug ml-1 Cytotoxicity against Homo sapiens (human) K562 ChEMBL. 15187442
IC50 (binding) = 0.4 uM Inhibition of mushroom tyrosinase ChEMBL. 18326070
IC50 (binding) = 0.4 uM Inhibition of mushroom tyrosinase ChEMBL. 18326070
IC50 (binding) = 0.4 uM Inhibition of mushroom tyrosinase ChEMBL. 18524420
IC50 (binding) = 0.4 uM Inhibition of mushroom tyrosinase ChEMBL. 19800229
IC50 (binding) = 0.4 uM Inhibition of mushroom tyrosinase after 10 mins ChEMBL. 21189019
IC50 (binding) = 2 uM Inhibition of dopamine beta-oxygenase (unknown origin) ChEMBL. 25089179
IC50 (binding) = 2.73 uM Inhibition of Bos taurus (bovine) pancrease carboxypeptidase A after 15 min ChEMBL. 14519960
IC50 (functional) > 100 uM Antimalarial activity against chloroquine-resistant Plasmodium falciparum K1 ChEMBL. 25089179
IC50 (binding) = 146 uM Inhibition of human recombinant MMP2 after 30 mins ChEMBL. 21189019
Inhibition (binding) = -3 % Inhibition of human recombinant 5-lipoxygenase at 1 mM after 10 mins by fluorescence assay ChEMBL. 21189019
Inhibition (binding) = 9 % Inhibition of mouse recombinant iNOS at 1 mM after 40 mins by colorimetric assay ChEMBL. 21189019
Inhibition (binding) = 55 % Inhibition of recombinant anthrax lethal factor at 1 mM after 30 mins by fluorescence assay ChEMBL. 21189019
Inhibition (binding) = 89 % Inhibition of human recombinant MMP2 at 1 mM after 30 mins ChEMBL. 21189019
Inhibition (binding) = 90 % Inhibition of mushroom tyrosinase at 1 mM after 10 mins ChEMBL. 21189019
Inhibition (binding) = 91 % Inhibition of human recombinant MMP9 at 1 mM after 30 mins ChEMBL. 21189019
Inhibition (binding) = 95 % Inhibition of human recombinant MMP3 at 1 mM after 30 mins ChEMBL. 21189019
Inhibition (binding) = 100 % Inhibition of human recombinant MMP8 at 1 mM after 30 mins ChEMBL. 21189019
Inhibition (binding) = 100 % Inhibition of human recombinant MMP1 at 1 mM after 30 mins ChEMBL. 21189019
mean log D (ADMET) = -0.14 Compound was tested for their chelating potential (free ligand) determined by distribution coefficient method. ChEMBL. 8809155
mean log D (ADMET) = 1.58 Compound was tested for their chelating potential with gallium-III complex determined by distribution coefficient method. ChEMBL. 8809155
mean log D (ADMET) = 1.74 Compound was tested for their chelating potential with Iron-III complex determined by distribution coefficient method. ChEMBL. 8809155
mean log D (ADMET) = 1.94 Compound was tested for their chelating potential with Indium-III complex determined by distribution coefficient method. ChEMBL. 8809155
Potency (functional) 19.8784 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule agonists of the NFkB signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 19.8784 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule agonists of the AP-1 signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 44.5022 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule antagonists of the androgen receptor (AR) signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 62.8611 uM PubChem BioAssay: Tox21. qHTS assay for small molecule activators of the heat shock response signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 62.8611 uM PubChem BioAssay: Tox21. qHTS assay to identify small molecule antagonists of the peroxisome proliferator-activated receptor delta (PPARd) signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference
Potency (functional) 78.4482 uM PubChem BioAssay: Tox21. qHTS assay for small molecule agonists of the antioxidant response element (ARE) signaling pathway. (Class of assay: confirmatory) ChEMBL. No reference

Phenotypes

Whole-cell/tissue/organism interactions

Species name Source Reference Is orphan
Mus musculus ChEMBL23 20045220
Homo sapiens ChEMBL23 15187442

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

11 literature references were collected for this gene.

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