Page last updated: 2024-11-09

4-hydroxyphenylmethylene hydantoin

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

Description

4-hydroxyphenylmethylene hydantoin: isoalted from the Red Sea sponge Hemimycale arabica; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID1550940
CHEMBL ID432684
SCHEMBL ID5346095
MeSH IDM0553286

Synonyms (33)

Synonym
(5z)-5-[(4-hydroxyphenyl)-methylene]-imidazolidine-2,4-dione
nsc49419
80171-33-1
SDCCGMLS-0064941.P001
bdbm50240462
(z)-5-(4-hydroxybenzylidene)-hydantoin
(z)-5-(4-hydroxybenzylidene)imidazolidine-2,4-dione
5-[1-(4-hydroxy-phenyl)-meth-(z)-ylidene]-imidazolidine-2,4-dione
4-hydroxyphenylmethylene hydantoin
CHEMBL432684 ,
HMS548F09
(5z)-5-[(4-hydroxyphenyl)methylidene]imidazolidine-2,4-dione
AKOS003248894
A839859
(5z)-5-(4-hydroxybenzylidene)imidazolidine-2,4-dione
STK742748
nsc 49419
2,4-imidazolidinedione, 5-((4-hydroxyphenyl)methylene)-
SCHEMBL5346095
5-(4-hydroxybenzylidene)hydantoin
hydantoin, 5-(p-hydroxybenzylidene)-
5-(p-hydroxybenzylidene)hydantoin
(5z)-5-(4-hydroxybenzylidene)-2,4-imidazolidinedione #
UPDDIBZITPTASO-YVMONPNESA-N
5-(4-hydroxyphenyl)methylenehydantoin
5-(4'-hydroxybenzylidene)hydantoin
2,4-imidazolidinedione, 5-[(4-hydroxyphenyl)methylene]-
HB4024
phenylmethylene hydantoin
sr-01000509736
SR-01000509736-1
(5z)-5-[(4-hydroxyphenyl)methylene]imidazolidine-2,4-dione
(5z)-5-(4-hydroxybenzylidene)-2,4-imidazolidinedione
[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)
Glycogen synthase kinase-3 betaHomo sapiens (human)IC50 (µMol)13.70000.00060.801310.0000AID430058
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (73)

Processvia Protein(s)Taxonomy
positive regulation of gene expressionGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of gene expressionGlycogen synthase kinase-3 betaHomo sapiens (human)
ER overload responseGlycogen synthase kinase-3 betaHomo sapiens (human)
peptidyl-serine phosphorylationGlycogen synthase kinase-3 betaHomo sapiens (human)
intracellular signal transductionGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of apoptotic processGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of protein export from nucleusGlycogen synthase kinase-3 betaHomo sapiens (human)
epithelial to mesenchymal transitionGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of cell-matrix adhesionGlycogen synthase kinase-3 betaHomo sapiens (human)
glycogen metabolic processGlycogen synthase kinase-3 betaHomo sapiens (human)
protein phosphorylationGlycogen synthase kinase-3 betaHomo sapiens (human)
mitochondrion organizationGlycogen synthase kinase-3 betaHomo sapiens (human)
dopamine receptor signaling pathwayGlycogen synthase kinase-3 betaHomo sapiens (human)
circadian rhythmGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of autophagyGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of gene expressionGlycogen synthase kinase-3 betaHomo sapiens (human)
peptidyl-serine phosphorylationGlycogen synthase kinase-3 betaHomo sapiens (human)
peptidyl-threonine phosphorylationGlycogen synthase kinase-3 betaHomo sapiens (human)
viral protein processingGlycogen synthase kinase-3 betaHomo sapiens (human)
hippocampus developmentGlycogen synthase kinase-3 betaHomo sapiens (human)
establishment of cell polarityGlycogen synthase kinase-3 betaHomo sapiens (human)
maintenance of cell polarityGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of cell migrationGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of axon extensionGlycogen synthase kinase-3 betaHomo sapiens (human)
neuron projection developmentGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of protein-containing complex assemblyGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of protein-containing complex assemblyGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of protein ubiquitinationGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of protein bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of proteasomal ubiquitin-dependent protein catabolic processGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of phosphoprotein phosphatase activityGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of microtubule-based processGlycogen synthase kinase-3 betaHomo sapiens (human)
intracellular signal transductionGlycogen synthase kinase-3 betaHomo sapiens (human)
cellular response to interleukin-3Glycogen synthase kinase-3 betaHomo sapiens (human)
regulation of circadian rhythmGlycogen synthase kinase-3 betaHomo sapiens (human)
proteasome-mediated ubiquitin-dependent protein catabolic processGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of GTPase activityGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of cell differentiationGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of osteoblast differentiationGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of glycogen biosynthetic processGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of cilium assemblyGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of protein catabolic processGlycogen synthase kinase-3 betaHomo sapiens (human)
protein autophosphorylationGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of protein export from nucleusGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of dendrite morphogenesisGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of axonogenesisGlycogen synthase kinase-3 betaHomo sapiens (human)
canonical Wnt signaling pathwayGlycogen synthase kinase-3 betaHomo sapiens (human)
excitatory postsynaptic potentialGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of microtubule cytoskeleton organizationGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of calcineurin-NFAT signaling cascadeGlycogen synthase kinase-3 betaHomo sapiens (human)
superior temporal gyrus developmentGlycogen synthase kinase-3 betaHomo sapiens (human)
cellular response to retinoic acidGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of canonical Wnt signaling pathwayGlycogen synthase kinase-3 betaHomo sapiens (human)
extrinsic apoptotic signaling pathwayGlycogen synthase kinase-3 betaHomo sapiens (human)
extrinsic apoptotic signaling pathway in absence of ligandGlycogen synthase kinase-3 betaHomo sapiens (human)
presynaptic modulation of chemical synaptic transmissionGlycogen synthase kinase-3 betaHomo sapiens (human)
neuron projection organizationGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of microtubule anchoring at centrosomeGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of cellular response to heatGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of protein localization to nucleusGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of long-term synaptic potentiationGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of mitochondrial outer membrane permeabilization involved in apoptotic signaling pathwayGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of protein acetylationGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of extrinsic apoptotic signaling pathway via death domain receptorsGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of protein localization to ciliumGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of dopaminergic neuron differentiationGlycogen synthase kinase-3 betaHomo sapiens (human)
cellular response to amyloid-betaGlycogen synthase kinase-3 betaHomo sapiens (human)
positive regulation of protein localization to centrosomeGlycogen synthase kinase-3 betaHomo sapiens (human)
beta-catenin destruction complex disassemblyGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of type B pancreatic cell developmentGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of glycogen (starch) synthase activityGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of mesenchymal stem cell differentiationGlycogen synthase kinase-3 betaHomo sapiens (human)
negative regulation of TOR signalingGlycogen synthase kinase-3 betaHomo sapiens (human)
regulation of neuron projection developmentGlycogen synthase kinase-3 betaHomo sapiens (human)
cell differentiationGlycogen synthase kinase-3 betaHomo sapiens (human)
insulin receptor signaling pathwayGlycogen synthase kinase-3 betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (17)

Processvia Protein(s)Taxonomy
protease bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
p53 bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
protein kinase activityGlycogen synthase kinase-3 betaHomo sapiens (human)
protein serine/threonine kinase activityGlycogen synthase kinase-3 betaHomo sapiens (human)
protein bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
ATP bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
beta-catenin bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
kinase activityGlycogen synthase kinase-3 betaHomo sapiens (human)
protein kinase bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
ubiquitin protein ligase bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
protein kinase A catalytic subunit bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
dynactin bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
tau protein bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
tau-protein kinase activityGlycogen synthase kinase-3 betaHomo sapiens (human)
NF-kappaB bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
RNA polymerase II-specific DNA-binding transcription factor bindingGlycogen synthase kinase-3 betaHomo sapiens (human)
protein serine kinase activityGlycogen synthase kinase-3 betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (14)

Processvia Protein(s)Taxonomy
glutamatergic synapseGlycogen synthase kinase-3 betaHomo sapiens (human)
nucleusGlycogen synthase kinase-3 betaHomo sapiens (human)
nucleoplasmGlycogen synthase kinase-3 betaHomo sapiens (human)
cytoplasmGlycogen synthase kinase-3 betaHomo sapiens (human)
mitochondrionGlycogen synthase kinase-3 betaHomo sapiens (human)
centrosomeGlycogen synthase kinase-3 betaHomo sapiens (human)
cytosolGlycogen synthase kinase-3 betaHomo sapiens (human)
plasma membraneGlycogen synthase kinase-3 betaHomo sapiens (human)
axonGlycogen synthase kinase-3 betaHomo sapiens (human)
dendriteGlycogen synthase kinase-3 betaHomo sapiens (human)
beta-catenin destruction complexGlycogen synthase kinase-3 betaHomo sapiens (human)
presynapseGlycogen synthase kinase-3 betaHomo sapiens (human)
postsynapseGlycogen synthase kinase-3 betaHomo sapiens (human)
Wnt signalosomeGlycogen synthase kinase-3 betaHomo sapiens (human)
cytosolGlycogen synthase kinase-3 betaHomo sapiens (human)
axonGlycogen synthase kinase-3 betaHomo sapiens (human)
nucleusGlycogen synthase kinase-3 betaHomo sapiens (human)
cytoplasmGlycogen synthase kinase-3 betaHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID538333Antimetastatic activity against human PC3 cells after 24 hrs by wound-healing assay2010European journal of medicinal chemistry, Nov, Volume: 45, Issue:11
Phenylmethylene hydantoins as prostate cancer invasion and migration inhibitors. CoMFA approach and QSAR analysis.
AID648279Inhibition of Escherichia coli MurA using PEP as substrate assessed as inorganic phosphate release at 25 uM preincubated for 10 mins measured after 60 mins by fluorimetric assay2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Privileged scaffolds or promiscuous binders: a comparative study on rhodanines and related heterocycles in medicinal chemistry.
AID538332Antimetastatic activity against human PC3 cells at 100 uM after 24 hrs by wound-healing assay2010European journal of medicinal chemistry, Nov, Volume: 45, Issue:11
Phenylmethylene hydantoins as prostate cancer invasion and migration inhibitors. CoMFA approach and QSAR analysis.
AID612367Antimigratory activity against human MDA-MB-231 cells at 200 uM after 24 hrs by wound healing assay2011Bioorganic & medicinal chemistry, Aug-15, Volume: 19, Issue:16
Semisynthetic analogues of the marine cembranoid sarcophine as prostate and breast cancer migration inhibitors.
AID393416Cytotoxicity against human PC3M cells assessed as cell viability up to 50 uM by MTT assay2009Bioorganic & medicinal chemistry, Feb-15, Volume: 17, Issue:4
Discovery, design, and synthesis of anti-metastatic lead phenylmethylene hydantoins inspired by marine natural products.
AID393156Antiinvasive activity in human PC3M cells expressing CTR assessed as inhibition of calcitonin-induced cell migration after 24 hrs by spheroid disaggregation assay2009Bioorganic & medicinal chemistry, Feb-15, Volume: 17, Issue:4
Discovery, design, and synthesis of anti-metastatic lead phenylmethylene hydantoins inspired by marine natural products.
AID612360Antimigratory activity against human PC3 cells at 200 uM after 24 hrs by wound healing assay2011Bioorganic & medicinal chemistry, Aug-15, Volume: 19, Issue:16
Semisynthetic analogues of the marine cembranoid sarcophine as prostate and breast cancer migration inhibitors.
AID648280Inhibition of Escherichia coli MetAP at 10 uM after 15 mins by fluorescence analysis2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Privileged scaffolds or promiscuous binders: a comparative study on rhodanines and related heterocycles in medicinal chemistry.
AID444567Inhibition of MCP1-induced chemotaxis in mouse RAW264.7 cells at 25 ug/mL relative to control2010Journal of medicinal chemistry, Jan-14, Volume: 53, Issue:1
Discovery of (Z)-5-(4-methoxybenzylidene)thiazolidine-2,4-dione, a readily available and orally active glitazone for the treatment of concanavalin A-induced acute liver injury of BALB/c mice.
AID393157Antiinvasive activity in human PC3M cells expressing CTR assessed as change in core spheroid at => 100 uM after 48 hrs by spheroid disaggregation assay2009Bioorganic & medicinal chemistry, Feb-15, Volume: 17, Issue:4
Discovery, design, and synthesis of anti-metastatic lead phenylmethylene hydantoins inspired by marine natural products.
AID648278Inhibition of bovine plasma thrombin using Boc-Val-Pro-Arg-AMC as substrate at 25 uM preincubated for 15 mins measured after 10 mins by fluorimetric assay2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Privileged scaffolds or promiscuous binders: a comparative study on rhodanines and related heterocycles in medicinal chemistry.
AID430058Inhibition of recombinant GSK3-beta by ELISA2009Bioorganic & medicinal chemistry, Aug-15, Volume: 17, Issue:16
The marine natural-derived inhibitors of glycogen synthase kinase-3beta phenylmethylene hydantoins: In vitro and in vivo activities and pharmacophore modeling.
AID479712Antimigratory activity against human PC3 cells at 200 uM by wound-healing assay2010Journal of natural products, May-28, Volume: 73, Issue:5
Pachycladins A-E, prostate cancer invasion and migration inhibitory Eunicellin-based diterpenoids from the red sea soft coral Cladiella pachyclados.
AID124090Anticonvulsant activity expressed as log(1/EDMES(2.5)) in MES assay on mice that responded a score of 2.52004Journal of medicinal chemistry, Mar-11, Volume: 47, Issue:6
Anticonvulsant activity of phenylmethylenehydantoins: a structure-activity relationship study.
AID112707Anticonvulsant activity measured as effective dose required to produce a response score of 2.5 in MES assay on mice2004Journal of medicinal chemistry, Mar-11, Volume: 47, Issue:6
Anticonvulsant activity of phenylmethylenehydantoins: a structure-activity relationship study.
AID648277Inhibition of Dengue virus NS2B-NS3 protease using Abz-NleKRRS-3-(NO2)Y as substrate at 50 uM preincubated for 15 mins measured every sec for 15 mins by fluorimetric analysis2012Journal of medicinal chemistry, Jan-26, Volume: 55, Issue:2
Privileged scaffolds or promiscuous binders: a comparative study on rhodanines and related heterocycles in medicinal chemistry.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[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-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (30.00)29.6817
2010's7 (70.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.95

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 Index11.95 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.35 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.95)

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]