Compounds > 3-cinnamoyl-4-hydroxy-6-methyl-2h-pyran-2-one
Page last updated: 2024-10-15

3-cinnamoyl-4-hydroxy-6-methyl-2h-pyran-2-one

Description

3-cinnamoyl-4-hydroxy-6-methyl-2H-pyran-2-one: inhibits human ovarian cell proliferation by inducing apoptosis; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID135400373
CHEMBL ID1385551
SCHEMBL ID10618560
MeSH IDM000612266

Synonyms (24)

Synonym
4-hydroxy-6-methyl-3-[(2e)-3-phenylprop-2-enoyl]-2h-pyran-2-one
BB 0218890
MLS001164113
smr000539560
AKOS001827579
4-hydroxy-6-methyl-3-(3-phenyl-acryloyl)-pyran-2-one
593278-92-3
CHEMBL1385551
HMS2858H07
56364-25-1
AB00073994-01
11Y-0823
SCHEMBL10618560
3-cinnamoyl-4-hydroxy-6-methyl-2h-pyran-2-one
4-hydroxy-6-methyl-3-[(2e)-3-phenyl-2-propenoyl]-2h-pyran-2-one
SR-01000195966-1
sr-01000195966
4-hydroxy-6-methyl-3-[(e)-3-phenyl-2-propenoyl]-2h-pyran-2-one
4-hydroxy-6-methyl-3-((e)-3-phenylacryloyl)-2h-pyran-2-one
(e)-3-cinnamoyl-4-hydroxy-6-methyl-2h-pyran-2-one
4-hydroxy-6-methyl-3-[(e)-3-phenylprop-2-enoyl]pyran-2-one
2h-pyran-2-one, 4-hydroxy-6-methyl-3-[(2e)-1-oxo-3-phenyl-2-propenyl]-
STARBLD0003789
CS-0326902
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (14)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
LuciferasePhotinus pyralis (common eastern firefly)Potency19.01150.007215.758889.3584AID588342
Nrf2Homo sapiens (human)Potency35.48130.09208.222223.1093AID624171
TDP1 proteinHomo sapiens (human)Potency29.09290.000811.382244.6684AID686978; AID686979
thioredoxin glutathione reductaseSchistosoma mansoniPotency44.66840.100022.9075100.0000AID485364
apical membrane antigen 1, AMA1Plasmodium falciparum 3D7Potency35.48130.707912.194339.8107AID720542
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency89.12510.035520.977089.1251AID504332
vitamin D3 receptor isoform VDRAHomo sapiens (human)Potency100.00000.354828.065989.1251AID504847
importin subunit beta-1 isoform 1Homo sapiens (human)Potency50.11875.804836.130665.1308AID540263
snurportin-1Homo sapiens (human)Potency50.11875.804836.130665.1308AID540263
peptidyl-prolyl cis-trans isomerase NIMA-interacting 1Homo sapiens (human)Potency42.56150.425612.059128.1838AID504891
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency19.95260.050127.073689.1251AID588590
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency35.48130.00798.23321,122.0200AID2546
gemininHomo sapiens (human)Potency20.59620.004611.374133.4983AID624296
DNA dC->dU-editing enzyme APOBEC-3F isoform aHomo sapiens (human)Potency1.41250.025911.239831.6228AID602313
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (34)

Assay IDTitleYearJournalArticle
AID762110Cytotoxicity against human HCT116 cells by MTT assay2013European journal of medicinal chemistry, Aug, Volume: 66Synthesis and bioevaluation of a series of α-pyrone derivatives as potent activators of Nrf2/ARE pathway (part I).
AID1416772Antibacterial activity against Staphylococcus aureus ATCC 25923 after 24 hrs by broth microdilution method2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID1416777Antibacterial activity against Enterococcus faecalis ATCC 51299 after 24 hrs by broth microdilution method2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID762114Induction of Nrf2/Keap1 in human HCT116 cells assessed as induction of ARE activity at 50 uM after 12 hrs by luciferase reporter gene assay relative to control2013European journal of medicinal chemistry, Aug, Volume: 66Synthesis and bioevaluation of a series of α-pyrone derivatives as potent activators of Nrf2/ARE pathway (part I).
AID1416785Cytotoxicity against human MCF7 cells assessed as growth inhibition by MTT assay2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID1416784Cytotoxicity against human HCT116 cells assessed as growth inhibition at 100 uM by MTT assay relative to control2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID1416776Antibacterial activity against Escherichia coli ATCC 10536 after 24 hrs by broth microdilution method2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID1416781Cytotoxicity against HEK293 cells assessed as growth inhibition at 100 uM by MTT assay relative to control2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID1416783Cytotoxicity against human PC3 cells assessed as growth inhibition at 100 uM by MTT assay relative to control2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID1416780Cytotoxicity against HEK293 cells by MTT assay2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID1416769Antimycobacterial activity against Mycobacterium smegmatis after 72 hrs by broth microdilution method2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID1416768Antitubercular activity against Mycobacterium tuberculosis H37Rv after 2 weeks by broth microdilution method2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID1416775Antibacterial activity against Bacillus subtilis ATCC 11774 after 24 hrs by broth microdilution method2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID762113Induction of Nrf2/Keap1 in human HCT116 cells assessed as induction of ARE activity at 20 uM after 12 hrs by luciferase reporter gene assay relative to control2013European journal of medicinal chemistry, Aug, Volume: 66Synthesis and bioevaluation of a series of α-pyrone derivatives as potent activators of Nrf2/ARE pathway (part I).
AID1416786Cytotoxicity against human PC3 cells assessed as growth inhibition by MTT assay2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID1416774Antibacterial activity against Micrococcus luteus ATCC 10240 after 24 hrs by broth microdilution method2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID1416779Antibacterial activity against Klebsiella pneumoniae ATCC BAA-2146 after 24 hrs by broth microdilution method2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID1416782Cytotoxicity against human MCF7 cells assessed as growth inhibition at 100 uM by MTT assay relative to control2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID1416787Cytotoxicity against human HCT116 cells assessed as growth inhibition by MTT assay2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID1416773Antibacterial activity against Staphylococcus epidermidis ATCC 12228 after 24 hrs by broth microdilution method2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID1416778Antibacterial activity against Pseudomonas aeruginosa ATCC 10145 after 24 hrs by broth microdilution method2018MedChemComm, Jan-01, Volume: 9, Issue:1
Synthesis and
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (12.50)29.6817
2010's6 (75.00)24.3611
2020's1 (12.50)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
isoniazid
Hydra: A genus of freshwater polyps in the family Hydridae, order Hydroida, class HYDROZOA. They are of special interest because of their complex organization and because their adult organization corresponds roughly to the gastrula of higher animals.. hydrazide : Compounds derived from oxoacids RkE(=O)l(OH)m (l =/= 0) by replacing -OH by -NRNR2 (R groups are commonly H). (IUPAC).		2.1710carbohydrazideantitubercular agent;
drug allergen
ethambutol
Ethambutol: An antitubercular agent that inhibits the transfer of mycolic acids into the cell wall of the tubercle bacillus. It may also inhibit the synthesis of spermidine in mycobacteria. The action is usually bactericidal, and the drug can penetrate human cell membranes to exert its lethal effect. (From Smith and Reynard, Textbook of Pharmacology, 1992, p863). ethambutol : An ethylenediamine derivative that is ethane-1,2-diamine in which one hydrogen attached to each of the nitrogens is sutstituted by a 1-hydroxybutan-2-yl group (S,S-configuration). It is a bacteriostatic antimycobacterial drug, effective against Mycobacterium tuberculosis and some other mycobacteria. It is used (as the dihydrochloride salt) in combination with other antituberculous drugs in the treatment of pulmonary and extrapulmonary tuberculosis; resistant strains of M. tuberculosis are readily produced if ethambutol is used alone.		2.1710ethanolamines;
ethylenediamine derivative		antitubercular agent;
environmental contaminant;
xenobiotic
2-tert-butylhydroquinone
2-tert-butylhydroquinone: an anticarcinogenic and chemopreventive agent. 2-tert-butylhydroquinone : A member of the class of hydroquinones in which one of the ring hydrogens of hydroquinone is replaced by a tert-butyl group.		2.0810hydroquinonesfood antioxidant
levofloxacin
Levofloxacin: The L-isomer of Ofloxacin.. levofloxacin : An optically active form of ofloxacin having (S)-configuration; an inhibitor of bacterial topoisomerase IV and DNA gyrase.		2.17109-fluoro-3-methyl-10-(4-methylpiperazin-1-yl)-7-oxo-2,3-dihydro-7H-[1,4]oxazino[2,3,4-ij]quinoline-6-carboxylic acid;
fluoroquinolone antibiotic;
quinolone antibiotic		antibacterial drug;
DNA synthesis inhibitor;
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor;
topoisomerase IV inhibitor
warfarin
Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.		2.1110benzenes;
hydroxycoumarin;
methyl ketone
rifampin
Rifampin: A semisynthetic antibiotic produced from Streptomyces mediterranei. It has a broad antibacterial spectrum, including activity against several forms of Mycobacterium. In susceptible organisms it inhibits DNA-dependent RNA polymerase activity by forming a stable complex with the enzyme. It thus suppresses the initiation of RNA synthesis. Rifampin is bactericidal, and acts on both intracellular and extracellular organisms. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1160)		2.1710cyclic ketal;
hydrazone;
N-iminopiperazine;
N-methylpiperazine;
rifamycins;
semisynthetic derivative;
zwitterion		angiogenesis inhibitor;
antiamoebic agent;
antineoplastic agent;
antitubercular agent;
DNA synthesis inhibitor;
EC 2.7.7.6 (RNA polymerase) inhibitor;
Escherichia coli metabolite;
geroprotector;
leprostatic drug;
neuroprotective agent;
pregnane X receptor agonist;
protein synthesis inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Innate Inflammatory Response
[description not available]		02.0510
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.0510
Cancer of Ovary
[description not available]		02.1110
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		02.1110