Page last updated: 2024-12-11

2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone

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Description

2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone: has antineoplastic activity; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5470829
CHEMBL ID270361
SCHEMBL ID24510580
MeSH IDM0470069

Synonyms (14)

Synonym
7249-34-5
nsc-43319
nsc43319
nsc705595
2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone
nsc-705595
bdbm50241496
CHEMBL270361 ,
AKOS001465212
(2e,5e)-2,5-bis[(4-hydroxy-3-methoxyphenyl)methylidene]cyclopentan-1-one
(2e,5e)-2,5-bis(4-hydroxy-3-methoxybenzylidene)cyclopentanone
(2e,5e)-2,5-bis(4-hydroxy-3-methoxybenzylidene) cyclopentanone
mfcd00365994
SCHEMBL24510580
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cytochrome P450 1A2Homo sapiens (human)IC50 (µMol)19,471.70000.00011.774010.0000AID349320
Cytochrome P450 3A4Homo sapiens (human)IC50 (µMol)32,464.14920.00011.753610.0000AID349321
Cytochrome P450 2C9 Homo sapiens (human)IC50 (µMol)1,400.89000.00002.800510.0000AID349322
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (36)

Processvia Protein(s)Taxonomy
steroid catabolic processCytochrome P450 1A2Homo sapiens (human)
porphyrin-containing compound metabolic processCytochrome P450 1A2Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 1A2Homo sapiens (human)
cholesterol metabolic processCytochrome P450 1A2Homo sapiens (human)
estrogen metabolic processCytochrome P450 1A2Homo sapiens (human)
toxin biosynthetic processCytochrome P450 1A2Homo sapiens (human)
post-embryonic developmentCytochrome P450 1A2Homo sapiens (human)
alkaloid metabolic processCytochrome P450 1A2Homo sapiens (human)
regulation of gene expressionCytochrome P450 1A2Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 1A2Homo sapiens (human)
dibenzo-p-dioxin metabolic processCytochrome P450 1A2Homo sapiens (human)
epoxygenase P450 pathwayCytochrome P450 1A2Homo sapiens (human)
lung developmentCytochrome P450 1A2Homo sapiens (human)
methylationCytochrome P450 1A2Homo sapiens (human)
monocarboxylic acid metabolic processCytochrome P450 1A2Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 1A2Homo sapiens (human)
retinol metabolic processCytochrome P450 1A2Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 1A2Homo sapiens (human)
cellular respirationCytochrome P450 1A2Homo sapiens (human)
aflatoxin metabolic processCytochrome P450 1A2Homo sapiens (human)
hydrogen peroxide biosynthetic processCytochrome P450 1A2Homo sapiens (human)
oxidative demethylationCytochrome P450 1A2Homo sapiens (human)
cellular response to cadmium ionCytochrome P450 1A2Homo sapiens (human)
omega-hydroxylase P450 pathwayCytochrome P450 1A2Homo sapiens (human)
lipid hydroxylationCytochrome P450 3A4Homo sapiens (human)
lipid metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid catabolic processCytochrome P450 3A4Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid metabolic processCytochrome P450 3A4Homo sapiens (human)
cholesterol metabolic processCytochrome P450 3A4Homo sapiens (human)
androgen metabolic processCytochrome P450 3A4Homo sapiens (human)
estrogen metabolic processCytochrome P450 3A4Homo sapiens (human)
alkaloid catabolic processCytochrome P450 3A4Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 3A4Homo sapiens (human)
calcitriol biosynthetic process from calciolCytochrome P450 3A4Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D metabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D catabolic processCytochrome P450 3A4Homo sapiens (human)
retinol metabolic processCytochrome P450 3A4Homo sapiens (human)
retinoic acid metabolic processCytochrome P450 3A4Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 3A4Homo sapiens (human)
aflatoxin metabolic processCytochrome P450 3A4Homo sapiens (human)
oxidative demethylationCytochrome P450 3A4Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 2C9 Homo sapiens (human)
steroid metabolic processCytochrome P450 2C9 Homo sapiens (human)
cholesterol metabolic processCytochrome P450 2C9 Homo sapiens (human)
estrogen metabolic processCytochrome P450 2C9 Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 2C9 Homo sapiens (human)
epoxygenase P450 pathwayCytochrome P450 2C9 Homo sapiens (human)
urea metabolic processCytochrome P450 2C9 Homo sapiens (human)
monocarboxylic acid metabolic processCytochrome P450 2C9 Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 2C9 Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 2C9 Homo sapiens (human)
amide metabolic processCytochrome P450 2C9 Homo sapiens (human)
icosanoid biosynthetic processCytochrome P450 2C9 Homo sapiens (human)
oxidative demethylationCytochrome P450 2C9 Homo sapiens (human)
omega-hydroxylase P450 pathwayCytochrome P450 2C9 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (33)

Processvia Protein(s)Taxonomy
monooxygenase activityCytochrome P450 1A2Homo sapiens (human)
iron ion bindingCytochrome P450 1A2Homo sapiens (human)
protein bindingCytochrome P450 1A2Homo sapiens (human)
electron transfer activityCytochrome P450 1A2Homo sapiens (human)
oxidoreductase activityCytochrome P450 1A2Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenCytochrome P450 1A2Homo sapiens (human)
enzyme bindingCytochrome P450 1A2Homo sapiens (human)
heme bindingCytochrome P450 1A2Homo sapiens (human)
demethylase activityCytochrome P450 1A2Homo sapiens (human)
caffeine oxidase activityCytochrome P450 1A2Homo sapiens (human)
aromatase activityCytochrome P450 1A2Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 1A2Homo sapiens (human)
estrogen 2-hydroxylase activityCytochrome P450 1A2Homo sapiens (human)
hydroperoxy icosatetraenoate dehydratase activityCytochrome P450 1A2Homo sapiens (human)
monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
steroid bindingCytochrome P450 3A4Homo sapiens (human)
iron ion bindingCytochrome P450 3A4Homo sapiens (human)
protein bindingCytochrome P450 3A4Homo sapiens (human)
steroid hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
retinoic acid 4-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
oxidoreductase activityCytochrome P450 3A4Homo sapiens (human)
oxygen bindingCytochrome P450 3A4Homo sapiens (human)
enzyme bindingCytochrome P450 3A4Homo sapiens (human)
heme bindingCytochrome P450 3A4Homo sapiens (human)
vitamin D3 25-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
caffeine oxidase activityCytochrome P450 3A4Homo sapiens (human)
quinine 3-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
testosterone 6-beta-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1-alpha,25-dihydroxyvitamin D3 23-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 8,9 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 11,12 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 14,15 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
aromatase activityCytochrome P450 3A4Homo sapiens (human)
vitamin D 24-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 2-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1,8-cineole 2-exo-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
monooxygenase activityCytochrome P450 2C9 Homo sapiens (human)
iron ion bindingCytochrome P450 2C9 Homo sapiens (human)
arachidonic acid epoxygenase activityCytochrome P450 2C9 Homo sapiens (human)
steroid hydroxylase activityCytochrome P450 2C9 Homo sapiens (human)
arachidonic acid 14,15-epoxygenase activityCytochrome P450 2C9 Homo sapiens (human)
arachidonic acid 11,12-epoxygenase activityCytochrome P450 2C9 Homo sapiens (human)
oxidoreductase activityCytochrome P450 2C9 Homo sapiens (human)
(S)-limonene 6-monooxygenase activityCytochrome P450 2C9 Homo sapiens (human)
(S)-limonene 7-monooxygenase activityCytochrome P450 2C9 Homo sapiens (human)
caffeine oxidase activityCytochrome P450 2C9 Homo sapiens (human)
(R)-limonene 6-monooxygenase activityCytochrome P450 2C9 Homo sapiens (human)
aromatase activityCytochrome P450 2C9 Homo sapiens (human)
heme bindingCytochrome P450 2C9 Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenCytochrome P450 2C9 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
endoplasmic reticulum membraneCytochrome P450 1A2Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 1A2Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 1A2Homo sapiens (human)
cytoplasmCytochrome P450 3A4Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 3A4Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 3A4Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 2C9 Homo sapiens (human)
plasma membraneCytochrome P450 2C9 Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2C9 Homo sapiens (human)
cytoplasmCytochrome P450 2C9 Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2C9 Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (33)

Assay IDTitleYearJournalArticle
AID349322Inhibition of human recombinant CYP2C92008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Structure-activity relationships for the inhibition of recombinant human cytochromes P450 by curcumin analogues.
AID1062642Inhibition of Wnt3A/beta-catenin signaling in HEK293 cells at 20 uM after 24 hrs by firefly/renilla dual luciferase reporter gene assay relative to vehicle-treated control2014European journal of medicinal chemistry, Jan, Volume: 71Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway.
AID1062644Inhibition of Wnt3A/beta-catenin signaling in HEK293 cells at 5 uM after 24 hrs by firefly/renilla dual luciferase reporter gene assay relative to vehicle-treated control2014European journal of medicinal chemistry, Jan, Volume: 71Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway.
AID349321Inhibition of human recombinant CYP3A42008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Structure-activity relationships for the inhibition of recombinant human cytochromes P450 by curcumin analogues.
AID1062640Inhibition of Wnt3A/beta-catenin signaling in HEK293 cells after 24 hrs by firefly/renilla dual luciferase reporter gene assay relative to curcumin2014European journal of medicinal chemistry, Jan, Volume: 71Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway.
AID349319Stability assessed as decomposition at 25 uM and pH 7.4 after 30 mins2008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Structure-activity relationships for the inhibition of recombinant human cytochromes P450 by curcumin analogues.
AID1062641Inhibition of Wnt3A/beta-catenin signaling in HEK293 cells after 24 hrs by firefly/renilla dual luciferase reporter gene assay2014European journal of medicinal chemistry, Jan, Volume: 71Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway.
AID417440Antiinflammatory activity in mouse J774A1 cells assessed as inhibition of LPS-induced IL6 production at 10 uM preincubated for 3 hrs before LPS challenge measured after 21 hrs by ELISA2009European journal of medicinal chemistry, Feb, Volume: 44, Issue:2
Synthesis, crystal structure and anti-inflammatory properties of curcumin analogues.
AID664955Cytotoxicity against human PC3 cells after 72 hrs by MTT assay2012European journal of medicinal chemistry, Jul, Volume: 53Synthesis and evaluation of curcumin-related compounds for anticancer activity.
AID417439Antiinflammatory activity in mouse J774A1 cells assessed as inhibition of LPS-induced TNFalpha production at 10 uM preincubated for 3 hrs before LPS challenge measured after 21 hrs by ELISA2009European journal of medicinal chemistry, Feb, Volume: 44, Issue:2
Synthesis, crystal structure and anti-inflammatory properties of curcumin analogues.
AID1062631Cytotoxicity against human U2OS cells at dual luciferase reporter gene assay EC50 after 24 hrs by MTS assay2014European journal of medicinal chemistry, Jan, Volume: 71Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway.
AID315766Antiinflammatory activity in mouse J774A.1 cells assessed as inhibition of lipopolysaccharide-induced TNFalpha production pretreated for 2 hrs at 10 uM before LPS challenge2008Bioorganic & medicinal chemistry letters, Feb-15, Volume: 18, Issue:4
Synthesis and anti-inflammatory activities of mono-carbonyl analogues of curcumin.
AID349320Inhibition of human recombinant CYP1A22008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Structure-activity relationships for the inhibition of recombinant human cytochromes P450 by curcumin analogues.
AID664956Cytotoxicity against human PANC1 cells after 72 hrs by MTT assay2012European journal of medicinal chemistry, Jul, Volume: 53Synthesis and evaluation of curcumin-related compounds for anticancer activity.
AID315767Antiinflammatory activity in mouse J774A.1 cells assessed as inhibition of lipopolysaccharide-induced IL6 production pretreated for 2 hrs at 10 uM before LPS challenge2008Bioorganic & medicinal chemistry letters, Feb-15, Volume: 18, Issue:4
Synthesis and anti-inflammatory activities of mono-carbonyl analogues of curcumin.
AID759524Inhibition of 11beta-HSD1 in rat testis microsomes using [3H]-11-DHC as substrate assessed as formation of CORT at 100 uM after 60 to 90 mins by radiometric analysis relative to control2013Bioorganic & medicinal chemistry letters, Aug-01, Volume: 23, Issue:15
Mono-carbonyl curcumin analogues as 11β-hydroxysteroid dehydrogenase 1 inhibitors.
AID1145209Antitumor activity against mouse ascites Sarcoma 180 cells allografted in ddN mouse assessed as percentage of total packed cell volume ratio at 100 mg/kg/day for 5 days administered 24 hrs after tumor inoculation measured 7th day after tumor inoculation1976Journal of medicinal chemistry, Mar, Volume: 19, Issue:3
Structure and antitumor activity relationship of 2-arylidene-4-cyclopentene-1, 3-diones and 2-arylideneindan-1, 3-diones.
AID344535Inhibition of human recombinant CYP2C9 in presence of reduced glutathione2008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Structure-activity relationships for the inhibition of recombinant human cytochromes P450 by curcumin analogues.
AID1062639Inhibition of Wnt3A/beta-catenin signaling-mediated Tcf4 transcriptional activity in human U2OS cells at dual luciferase reporter gene assay EC50 after 24 hrs by FOPglow reporter gene assay2014European journal of medicinal chemistry, Jan, Volume: 71Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway.
AID759512Inhibition of 11beta-HSD2 in human kidney microsomes using [3H]-cortisol as substrate assessed as formation of cortisone at 100 uM after 30 mins by radiometric analysis relative to control2013Bioorganic & medicinal chemistry letters, Aug-01, Volume: 23, Issue:15
Mono-carbonyl curcumin analogues as 11β-hydroxysteroid dehydrogenase 1 inhibitors.
AID1062645Inhibition of Wnt3A/beta-catenin signaling in HEK293 cells at 1 uM after 24 hrs by firefly/renilla dual luciferase reporter gene assay relative to vehicle-treated control2014European journal of medicinal chemistry, Jan, Volume: 71Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway.
AID759517Inhibition of human 11beta-HSD1 transfected in CHOP cells at 100 uM relative to control2013Bioorganic & medicinal chemistry letters, Aug-01, Volume: 23, Issue:15
Mono-carbonyl curcumin analogues as 11β-hydroxysteroid dehydrogenase 1 inhibitors.
AID1062643Inhibition of Wnt3A/beta-catenin signaling in HEK293 cells at 10 uM after 24 hrs by firefly/renilla dual luciferase reporter gene assay relative to vehicle-treated control2014European journal of medicinal chemistry, Jan, Volume: 71Functionalized curcumin analogs as potent modulators of the Wnt/β-catenin signaling pathway.
AID344534Inhibition of human recombinant CYP1A2 in presence of reduced glutathione2008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Structure-activity relationships for the inhibition of recombinant human cytochromes P450 by curcumin analogues.
AID759519Inhibition of 11beta-HSD1 in Sprague-Dawley rat leydig cells at 100 uM relative to control2013Bioorganic & medicinal chemistry letters, Aug-01, Volume: 23, Issue:15
Mono-carbonyl curcumin analogues as 11β-hydroxysteroid dehydrogenase 1 inhibitors.
AID344536Inhibition of human recombinant CYP2D6 in presence of reduced glutathione2008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Structure-activity relationships for the inhibition of recombinant human cytochromes P450 by curcumin analogues.
AID664957Cytotoxicity against human HT-29 cells after 72 hrs by MTT assay2012European journal of medicinal chemistry, Jul, Volume: 53Synthesis and evaluation of curcumin-related compounds for anticancer activity.
AID344533Inhibition of human recombinant CYP3A4 in presence of reduced glutathione2008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Structure-activity relationships for the inhibition of recombinant human cytochromes P450 by curcumin analogues.
AID759526Inhibition of 11beta-HSD1 in human liver microsomes using [3H]-cortisone as substrate assessed as formation of cortisol at 100 uM after 60 to 90 mins by radiometric analysis relative to control2013Bioorganic & medicinal chemistry letters, Aug-01, Volume: 23, Issue:15
Mono-carbonyl curcumin analogues as 11β-hydroxysteroid dehydrogenase 1 inhibitors.
AID759513Inhibition of 11beta-HSD2 in rat kidney microsomes using [3H]-CORT as substrate assessed as formation of 11-DHC at 100 uM after 30 mins by radiometric analysis relative to control2013Bioorganic & medicinal chemistry letters, Aug-01, Volume: 23, Issue:15
Mono-carbonyl curcumin analogues as 11β-hydroxysteroid dehydrogenase 1 inhibitors.
AID344537Inhibition of human recombinant CYP2B6 in presence of reduced glutathione2008European journal of medicinal chemistry, Aug, Volume: 43, Issue:8
Structure-activity relationships for the inhibition of recombinant human cytochromes P450 by curcumin analogues.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (10.00)18.7374
1990's0 (0.00)18.2507
2000's4 (40.00)29.6817
2010's4 (40.00)24.3611
2020's1 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.92

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 Index11.92 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.32 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.92)

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%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]