Page last updated: 2024-12-08

dihydropinosylvin

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

Description

dihydropinosylvin : A member of the class of resorcinols carrying an additional 2-phenylethyl substituent at position 5. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID442700
CHEMBL ID228120
CHEBI ID4579
SCHEMBL ID501070

Synonyms (27)

Synonym
14531-52-3
dihydropinosylvin
LMPK13090034
chebi:4579 ,
3,5-dihydroxybibenzyl
CHEMBL228120 ,
FT-0657704
5-phenethylbenzene-1,3-diol
bdbm50211960
5-(2-phenylethyl)benzene-1,3-diol
A808347
LDBYHULIXFIJAZ-UHFFFAOYSA-N
AKOS015915007
SCHEMBL501070
5-(2-phenylethyl)resorcinol
1,3-benzenediol, 5-(2-phenylethyl)-
AC-24221
DTXSID30331915
mfcd16294420
Q27106413
5-(2-phenylethyl)-1,3-benzenediol; 5-phenethylresorcinol; dihydropinosylvin
resorcinol, 5-phenethyl-
E77955
SY262044
AS-75962
CS-0024158
HY-N3753
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
EC 1.14.18.1 (tyrosinase) inhibitorAny EC 1.14.18.* (oxidoreductase acting on paired donors, miscellaneous compound as one donor, incorporating 1 atom of oxygen) inhibitor that interferes with the action of tyrosinase (monophenol monooxygenase), EC 1.14.18.1, an enzyme that catalyses the oxidation of phenols (such as tyrosine) and is widespread in plants and animals.
plant metaboliteAny eukaryotic metabolite produced during a metabolic reaction in plants, the kingdom that include flowering plants, conifers and other gymnosperms.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
resorcinolsAny benzenediol in which the two hydroxy groups are meta to one another.
diphenylethaneCompounds containing two phenyl groups connected by an ethyl linker.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Pathways (1)

PathwayProteinsCompounds
pinosylvin metabolism211

Protein Targets (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Prostaglandin G/H synthase 1Homo sapiens (human)IC50 (µMol)46.70000.00021.557410.0000AID287085
Prostaglandin G/H synthase 2Homo sapiens (human)IC50 (µMol)46.70000.00010.995010.0000AID287086
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (60)

Processvia Protein(s)Taxonomy
prostaglandin biosynthetic processProstaglandin G/H synthase 1Homo sapiens (human)
response to oxidative stressProstaglandin G/H synthase 1Homo sapiens (human)
regulation of blood pressureProstaglandin G/H synthase 1Homo sapiens (human)
cyclooxygenase pathwayProstaglandin G/H synthase 1Homo sapiens (human)
regulation of cell population proliferationProstaglandin G/H synthase 1Homo sapiens (human)
cellular oxidant detoxificationProstaglandin G/H synthase 1Homo sapiens (human)
prostaglandin biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
angiogenesisProstaglandin G/H synthase 2Homo sapiens (human)
response to oxidative stressProstaglandin G/H synthase 2Homo sapiens (human)
embryo implantationProstaglandin G/H synthase 2Homo sapiens (human)
learningProstaglandin G/H synthase 2Homo sapiens (human)
memoryProstaglandin G/H synthase 2Homo sapiens (human)
regulation of blood pressureProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of cell population proliferationProstaglandin G/H synthase 2Homo sapiens (human)
response to xenobiotic stimulusProstaglandin G/H synthase 2Homo sapiens (human)
response to nematodeProstaglandin G/H synthase 2Homo sapiens (human)
response to fructoseProstaglandin G/H synthase 2Homo sapiens (human)
response to manganese ionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of vascular endothelial growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
cyclooxygenase pathwayProstaglandin G/H synthase 2Homo sapiens (human)
bone mineralizationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of prostaglandin biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of fever generationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of synaptic plasticityProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of synaptic transmission, dopaminergicProstaglandin G/H synthase 2Homo sapiens (human)
prostaglandin secretionProstaglandin G/H synthase 2Homo sapiens (human)
response to estradiolProstaglandin G/H synthase 2Homo sapiens (human)
response to lipopolysaccharideProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of peptidyl-serine phosphorylationProstaglandin G/H synthase 2Homo sapiens (human)
response to vitamin DProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to heatProstaglandin G/H synthase 2Homo sapiens (human)
response to tumor necrosis factorProstaglandin G/H synthase 2Homo sapiens (human)
maintenance of blood-brain barrierProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of protein import into nucleusProstaglandin G/H synthase 2Homo sapiens (human)
hair cycleProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of apoptotic processProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of nitric oxide biosynthetic processProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of cell cycleProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of vasoconstrictionProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of smooth muscle contractionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of smooth muscle contractionProstaglandin G/H synthase 2Homo sapiens (human)
decidualizationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of smooth muscle cell proliferationProstaglandin G/H synthase 2Homo sapiens (human)
regulation of inflammatory responseProstaglandin G/H synthase 2Homo sapiens (human)
brown fat cell differentiationProstaglandin G/H synthase 2Homo sapiens (human)
response to glucocorticoidProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of calcium ion transportProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of synaptic transmission, glutamatergicProstaglandin G/H synthase 2Homo sapiens (human)
response to fatty acidProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to mechanical stimulusProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to lead ionProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to ATPProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to hypoxiaProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to non-ionic osmotic stressProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to fluid shear stressProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of transforming growth factor beta productionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of cell migration involved in sprouting angiogenesisProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of fibroblast growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of brown fat cell differentiationProstaglandin G/H synthase 2Homo sapiens (human)
positive regulation of platelet-derived growth factor productionProstaglandin G/H synthase 2Homo sapiens (human)
cellular oxidant detoxificationProstaglandin G/H synthase 2Homo sapiens (human)
regulation of neuroinflammatory responseProstaglandin G/H synthase 2Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to osmotic stressProstaglandin G/H synthase 2Homo sapiens (human)
cellular response to homocysteineProstaglandin G/H synthase 2Homo sapiens (human)
response to angiotensinProstaglandin G/H synthase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
peroxidase activityProstaglandin G/H synthase 1Homo sapiens (human)
prostaglandin-endoperoxide synthase activityProstaglandin G/H synthase 1Homo sapiens (human)
protein bindingProstaglandin G/H synthase 1Homo sapiens (human)
heme bindingProstaglandin G/H synthase 1Homo sapiens (human)
metal ion bindingProstaglandin G/H synthase 1Homo sapiens (human)
oxidoreductase activity, acting on single donors with incorporation of molecular oxygen, incorporation of two atoms of oxygenProstaglandin G/H synthase 1Homo sapiens (human)
peroxidase activityProstaglandin G/H synthase 2Homo sapiens (human)
prostaglandin-endoperoxide synthase activityProstaglandin G/H synthase 2Homo sapiens (human)
protein bindingProstaglandin G/H synthase 2Homo sapiens (human)
enzyme bindingProstaglandin G/H synthase 2Homo sapiens (human)
heme bindingProstaglandin G/H synthase 2Homo sapiens (human)
protein homodimerization activityProstaglandin G/H synthase 2Homo sapiens (human)
metal ion bindingProstaglandin G/H synthase 2Homo sapiens (human)
oxidoreductase activity, acting on single donors with incorporation of molecular oxygen, incorporation of two atoms of oxygenProstaglandin G/H synthase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (13)

Processvia Protein(s)Taxonomy
photoreceptor outer segmentProstaglandin G/H synthase 1Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 1Homo sapiens (human)
endoplasmic reticulum membraneProstaglandin G/H synthase 1Homo sapiens (human)
Golgi apparatusProstaglandin G/H synthase 1Homo sapiens (human)
intracellular membrane-bounded organelleProstaglandin G/H synthase 1Homo sapiens (human)
extracellular exosomeProstaglandin G/H synthase 1Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 1Homo sapiens (human)
neuron projectionProstaglandin G/H synthase 1Homo sapiens (human)
nuclear inner membraneProstaglandin G/H synthase 2Homo sapiens (human)
nuclear outer membraneProstaglandin G/H synthase 2Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulumProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulum lumenProstaglandin G/H synthase 2Homo sapiens (human)
endoplasmic reticulum membraneProstaglandin G/H synthase 2Homo sapiens (human)
caveolaProstaglandin G/H synthase 2Homo sapiens (human)
neuron projectionProstaglandin G/H synthase 2Homo sapiens (human)
protein-containing complexProstaglandin G/H synthase 2Homo sapiens (human)
neuron projectionProstaglandin G/H synthase 2Homo sapiens (human)
cytoplasmProstaglandin G/H synthase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (17)

Assay IDTitleYearJournalArticle
AID716916Cytotoxicity against mouse B16F10 cells assessed as suppression of cell viability at 12.5 to 200 uM after 72 hrs2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Resveratrol as a kcat type inhibitor for tyrosinase: potentiated melanogenesis inhibitor.
AID716921Antimelanogenic activity in mouse assessed as cellular melanin content B16F10 cells after 72 hrs by spectrophotometric analysis2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Resveratrol as a kcat type inhibitor for tyrosinase: potentiated melanogenesis inhibitor.
AID287085Inhibition of COX1 by radioimmunoassay method2007Journal of natural products, May, Volume: 70, Issue:5
Bioactive compounds from Bauhinia purpurea possessing antimalarial, antimycobacterial, antifungal, anti-inflammatory, and cytotoxic activities.
AID377036Ex vivo inhibition of leukotriene formation in calcium ionophore activated human neutrophilic granulocyte by ELISA2005Journal of natural products, Jan, Volume: 68, Issue:1
Inhibition of leukotriene biosynthesis by stilbenoids from Stemona species.
AID399545Spasmolytic activity in guinea pig ileum assessed as inhibition of spontaneous contraction2004Journal of natural products, Feb, Volume: 67, Issue:2
Spasmolytic effects, mode of action, and structure-activity relationships of stilbenoids from Nidema boothii.
AID287088Cytotoxicity against BC cells by colorimetric method2007Journal of natural products, May, Volume: 70, Issue:5
Bioactive compounds from Bauhinia purpurea possessing antimalarial, antimycobacterial, antifungal, anti-inflammatory, and cytotoxic activities.
AID399550Inhibition of bovine brain CaM-dependent PDE assessed as inorganic phosphate release in presence of bovine brain calmodulin2004Journal of natural products, Feb, Volume: 67, Issue:2
Spasmolytic effects, mode of action, and structure-activity relationships of stilbenoids from Nidema boothii.
AID589667Induction of NGF production in rat C6 cells at 20 uM after 24 hrs by ELISA relative to untreated control2011Bioorganic & medicinal chemistry letters, Apr-01, Volume: 21, Issue:7
Furostanol saponins from the rhizomes of Dioscorea japonica and their effects on NGF induction.
AID399546Spasmolytic activity in guinea pig ileum assessed as inhibition of spontaneous contraction relative to papaverine2004Journal of natural products, Feb, Volume: 67, Issue:2
Spasmolytic effects, mode of action, and structure-activity relationships of stilbenoids from Nidema boothii.
AID399549Binding affinity to bovine brain calmodulin by electrophoretic mobility assay in presence of calcium chloride2004Journal of natural products, Feb, Volume: 67, Issue:2
Spasmolytic effects, mode of action, and structure-activity relationships of stilbenoids from Nidema boothii.
AID589668Cytotoxicity against rat C6 cells assessed as viable cells at 20 uM after 24 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Apr-01, Volume: 21, Issue:7
Furostanol saponins from the rhizomes of Dioscorea japonica and their effects on NGF induction.
AID287084Antifungal activity against Candida albicans by colorimetric method2007Journal of natural products, May, Volume: 70, Issue:5
Bioactive compounds from Bauhinia purpurea possessing antimalarial, antimycobacterial, antifungal, anti-inflammatory, and cytotoxic activities.
AID377037Ex vivo inhibition of leukotriene formation in calcium ionophore activated human neutrophilic granulocyte at 50 uM by ELISA2005Journal of natural products, Jan, Volume: 68, Issue:1
Inhibition of leukotriene biosynthesis by stilbenoids from Stemona species.
AID287082Antimycobacterial activity against Mycobacterium tuberculosis H37Ra by microplate Alamar Blue assay2007Journal of natural products, May, Volume: 70, Issue:5
Bioactive compounds from Bauhinia purpurea possessing antimalarial, antimycobacterial, antifungal, anti-inflammatory, and cytotoxic activities.
AID287087Cytotoxicity against KB cells by colorimetric method2007Journal of natural products, May, Volume: 70, Issue:5
Bioactive compounds from Bauhinia purpurea possessing antimalarial, antimycobacterial, antifungal, anti-inflammatory, and cytotoxic activities.
AID287086Inhibition of COX2 by radioimmunoassay method2007Journal of natural products, May, Volume: 70, Issue:5
Bioactive compounds from Bauhinia purpurea possessing antimalarial, antimycobacterial, antifungal, anti-inflammatory, and cytotoxic activities.
AID287083Antimalarial activity against multidrug-resistant Plasmodium falciparum K1 by micro culture radioisotope technique2007Journal of natural products, May, Volume: 70, Issue:5
Bioactive compounds from Bauhinia purpurea possessing antimalarial, antimycobacterial, antifungal, anti-inflammatory, and cytotoxic activities.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (60.00)29.6817
2010's2 (40.00)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: 17.81

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index17.81 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.42 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.81)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]