Page last updated: 2024-12-11

2-crotonyloxymethyl-2-cyclohexenone

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

2-crotonyloxymethyl-2-cyclohexenone: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID6439061
CHEMBL ID60020
SCHEMBL ID5496677
SCHEMBL ID5496671
MeSH IDM0198569

Synonyms (14)

Synonym
2-comc
2-crotonyloxymethyl-cyclohex-2-enone
bdbm50122751
(6-oxo-cyclohex-1-enyl)-acetic acid (e)-propenyl ester
(6-oxocyclohex-1-enyl)methyl but-2-enoate
but-2-enoic acid 6-oxo-cyclohex-1-enylmethyl ester
CHEMBL60020 ,
(6-oxocyclohexen-1-yl)methyl (e)-but-2-enoate
2-butenoic acid, (6-oxo-1-cyclohexen-1-yl)methyl ester
106281-45-2
2-crotonyloxymethyl-2-cyclohexenone
SCHEMBL5496677
SCHEMBL5496671
comc
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glutathione S-transferase PHomo sapiens (human)IC50 (µMol)21.40000.05121.70194.0000AID254795; AID254811
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (33)

Processvia Protein(s)Taxonomy
response to reactive oxygen speciesGlutathione S-transferase PHomo sapiens (human)
negative regulation of acute inflammatory responseGlutathione S-transferase PHomo sapiens (human)
negative regulation of protein kinase activityGlutathione S-transferase PHomo sapiens (human)
prostaglandin metabolic processGlutathione S-transferase PHomo sapiens (human)
glutathione metabolic processGlutathione S-transferase PHomo sapiens (human)
xenobiotic metabolic processGlutathione S-transferase PHomo sapiens (human)
central nervous system developmentGlutathione S-transferase PHomo sapiens (human)
negative regulation of biosynthetic processGlutathione S-transferase PHomo sapiens (human)
negative regulation of tumor necrosis factor-mediated signaling pathwayGlutathione S-transferase PHomo sapiens (human)
negative regulation of interleukin-1 beta productionGlutathione S-transferase PHomo sapiens (human)
negative regulation of tumor necrosis factor productionGlutathione S-transferase PHomo sapiens (human)
regulation of stress-activated MAPK cascadeGlutathione S-transferase PHomo sapiens (human)
negative regulation of stress-activated MAPK cascadeGlutathione S-transferase PHomo sapiens (human)
positive regulation of superoxide anion generationGlutathione S-transferase PHomo sapiens (human)
common myeloid progenitor cell proliferationGlutathione S-transferase PHomo sapiens (human)
nitric oxide storageGlutathione S-transferase PHomo sapiens (human)
negative regulation of apoptotic processGlutathione S-transferase PHomo sapiens (human)
negative regulation of canonical NF-kappaB signal transductionGlutathione S-transferase PHomo sapiens (human)
negative regulation of MAP kinase activityGlutathione S-transferase PHomo sapiens (human)
negative regulation of MAPK cascadeGlutathione S-transferase PHomo sapiens (human)
negative regulation of JUN kinase activityGlutathione S-transferase PHomo sapiens (human)
linoleic acid metabolic processGlutathione S-transferase PHomo sapiens (human)
negative regulation of fibroblast proliferationGlutathione S-transferase PHomo sapiens (human)
hepoxilin biosynthetic processGlutathione S-transferase PHomo sapiens (human)
negative regulation of nitric-oxide synthase biosynthetic processGlutathione S-transferase PHomo sapiens (human)
regulation of ERK1 and ERK2 cascadeGlutathione S-transferase PHomo sapiens (human)
negative regulation of ERK1 and ERK2 cascadeGlutathione S-transferase PHomo sapiens (human)
negative regulation of leukocyte proliferationGlutathione S-transferase PHomo sapiens (human)
cellular response to lipopolysaccharideGlutathione S-transferase PHomo sapiens (human)
negative regulation of monocyte chemotactic protein-1 productionGlutathione S-transferase PHomo sapiens (human)
cellular oxidant detoxificationGlutathione S-transferase PHomo sapiens (human)
glutathione derivative biosynthetic processGlutathione S-transferase PHomo sapiens (human)
negative regulation of extrinsic apoptotic signaling pathwayGlutathione S-transferase PHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

Processvia Protein(s)Taxonomy
glutathione transferase activityGlutathione S-transferase PHomo sapiens (human)
glutathione peroxidase activityGlutathione S-transferase PHomo sapiens (human)
fatty acid bindingGlutathione S-transferase PHomo sapiens (human)
protein bindingGlutathione S-transferase PHomo sapiens (human)
JUN kinase bindingGlutathione S-transferase PHomo sapiens (human)
kinase regulator activityGlutathione S-transferase PHomo sapiens (human)
S-nitrosoglutathione bindingGlutathione S-transferase PHomo sapiens (human)
dinitrosyl-iron complex bindingGlutathione S-transferase PHomo sapiens (human)
nitric oxide bindingGlutathione S-transferase PHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
extracellular regionGlutathione S-transferase PHomo sapiens (human)
extracellular spaceGlutathione S-transferase PHomo sapiens (human)
nucleusGlutathione S-transferase PHomo sapiens (human)
cytoplasmGlutathione S-transferase PHomo sapiens (human)
mitochondrionGlutathione S-transferase PHomo sapiens (human)
cytosolGlutathione S-transferase PHomo sapiens (human)
vesicleGlutathione S-transferase PHomo sapiens (human)
secretory granule lumenGlutathione S-transferase PHomo sapiens (human)
extracellular exosomeGlutathione S-transferase PHomo sapiens (human)
ficolin-1-rich granule lumenGlutathione S-transferase PHomo sapiens (human)
TRAF2-GSTP1 complexGlutathione S-transferase PHomo sapiens (human)
cytosolGlutathione S-transferase PHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (24)

Assay IDTitleYearJournalArticle
AID1665580Antitumor activity against human HT-29 cells xenografted in nude BALB/c mouse assessed as reduction in tumor volume at 40 mg/kg, ip dosed every day for 21 days
AID1665556Antiproliferative activity against human HT-29 cells by MTT assay
AID1665603Induction of autophagy in human HT-29 cells assessed as reduction in p62 protein level at 2.5 uM incubated for 72 hrs by Western blot analysis
AID254795Inhibitory concentration against GSTP1-1 over-expressed in MCF7wt cells2005Journal of medicinal chemistry, Oct-20, Volume: 48, Issue:21
Selective inhibition of MCF-7(piGST) breast tumors using glutathione transferase-derived 2-methylene-cycloalkenones.
AID305797Cytotoxicity against human H460 cells by MTT assay2007Bioorganic & medicinal chemistry letters, Jan-15, Volume: 17, Issue:2
Analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) with anti-tumor properties.
AID1665593Induction of apoptosis in human HT-29 cells assessed as increase in Bax protein level at 2.5 uM incubated for 72 hrs by Western blot analysis
AID1665595Induction of apoptosis in human HT-29 cells assessed as reduction in Bcl2 protein level at 2.5 uM incubated for 72 hrs by Western blot analysis
AID305796Cytotoxicity against human A549 cells by MTT assay2007Bioorganic & medicinal chemistry letters, Jan-15, Volume: 17, Issue:2
Analogues of 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC) with anti-tumor properties.
AID84292Tested for cytotoxicity against HT-29 (MDR)cells2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Molecular basis of the antitumor activities of 2-crotonyloxymethyl-2-cycloalkenones.
AID1665599Induction of apoptosis in human HT-29 cells assessed as increase in cleaved caspase-3 protein level at 2.5 uM incubated for 72 hrs by Western blot analysis
AID255162Ratio between MCF7wt to MCF-7piGST cells overexpressing in GSTP1-12005Journal of medicinal chemistry, Oct-20, Volume: 48, Issue:21
Selective inhibition of MCF-7(piGST) breast tumors using glutathione transferase-derived 2-methylene-cycloalkenones.
AID1665557Antiproliferative activity against human HepG2 cells by MTT assay
AID309932Cytotoxicity against human H460 cells assessed as surviving cells after 4 days by MTT assay2007Bioorganic & medicinal chemistry letters, Nov-01, Volume: 17, Issue:21
Arene cis-dihydrodiols: useful precursors for the preparation of analogues of the anti-tumour agent, 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC).
AID1665558Antiproliferative activity against rat 9L-2 cells by MTT assay
AID84293Tested for cytotoxicity against HT-29 (wt)cells2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Molecular basis of the antitumor activities of 2-crotonyloxymethyl-2-cycloalkenones.
AID1665598Induction of apoptosis in human HT-29 cells assessed as increase in cleaved PARP protein level at 2.5 uM incubated for 72 hrs by Western blot analysis
AID1665602Induction of autophagy in human HT-29 cells assessed as increase in Beclin-1 protein level at 2.5 uM incubated for 72 hrs by Western blot analysis
AID40726Tested in vitro growth inhibition against B16 melanotic melanoma cells2003Journal of medicinal chemistry, Jan-02, Volume: 46, Issue:1
Molecular basis of the antitumor activities of 2-crotonyloxymethyl-2-cycloalkenones.
AID1665584Induction of apoptosis in human HT-29 cells at 2.5 uM incubated for 72 hrs by FITC-AnnexinV/PI staining based flow cytometry relative to control
AID309931Cytotoxicity against human A549 cells assessed as surviving cells after 4 days by MTT assay2007Bioorganic & medicinal chemistry letters, Nov-01, Volume: 17, Issue:21
Arene cis-dihydrodiols: useful precursors for the preparation of analogues of the anti-tumour agent, 2-crotonyloxymethyl-(4R,5R,6R)-4,5,6-trihydroxycyclohex-2-enone (COTC).
AID254811Inhibitory concentration against GSTP1-1 over-expressed in MCF-7piGST cells2005Journal of medicinal chemistry, Oct-20, Volume: 48, Issue:21
Selective inhibition of MCF-7(piGST) breast tumors using glutathione transferase-derived 2-methylene-cycloalkenones.
AID1665559Cytotoxicity against human CCD-841 cells by MTT assay
AID1665601Induction of autophagy in human HT-29 cells assessed as increase in LC3-II protein level at 2.5 uM incubated for 72 hrs by Western blot analysis
AID1665582Antitumor activity against human HT-29 cells xenografted in nude BALB/c mouse assessed as tumor weight level at 40 mg/kg, ip dosed every day for 21 days (Rvb = 1.49 +/- 0.27 g)
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (11.11)18.2507
2000's7 (77.78)29.6817
2010's0 (0.00)24.3611
2020's1 (11.11)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.83

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.83 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index5.14 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.83)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]