Page last updated: 2024-12-11

3,4-dihydroxy-xanthone

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Description

3,4-dihydroxy-xanthone: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5748382
CHEMBL ID446323
SCHEMBL ID133422
MeSH IDM0200553

Synonyms (13)

Synonym
3,4-dihydroxyxanthone
9h-xanthen-9-one, 3,4-dihydroxy-
3,4-dihydroxy-xanthone
39731-48-1
3,4-dihydroxyxanthen-9-one
bdbm50269645
CHEMBL446323 ,
SCHEMBL133422
YFVCSEXMOBEPQB-UHFFFAOYSA-N
3,4-dihydroxy-9h-xanthen-9-one
3,4-dihydroxy-xanthen-9-one
DTXSID20192815
PD181110
[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)
TyrosinaseHomo sapiens (human)IC50 (µMol)5.12000.02304.459310.0000AID1683486
Prostaglandin G/H synthase 1Homo sapiens (human)IC50 (µMol)100.00000.00021.557410.0000AID403703
Prostaglandin G/H synthase 2Homo sapiens (human)IC50 (µMol)1.89000.00010.995010.0000AID403704
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (70)

Processvia Protein(s)Taxonomy
melanin biosynthetic process from tyrosineTyrosinaseHomo sapiens (human)
eye pigment biosynthetic processTyrosinaseHomo sapiens (human)
visual perceptionTyrosinaseHomo sapiens (human)
cell population proliferationTyrosinaseHomo sapiens (human)
response to UVTyrosinaseHomo sapiens (human)
response to blue lightTyrosinaseHomo sapiens (human)
response to vitamin DTyrosinaseHomo sapiens (human)
melanin biosynthetic processTyrosinaseHomo sapiens (human)
thymus developmentTyrosinaseHomo sapiens (human)
response to cAMPTyrosinaseHomo sapiens (human)
pigmentationTyrosinaseHomo sapiens (human)
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 (11)

Processvia Protein(s)Taxonomy
tyrosinase activityTyrosinaseHomo sapiens (human)
copper ion bindingTyrosinaseHomo sapiens (human)
protein bindingTyrosinaseHomo sapiens (human)
identical protein bindingTyrosinaseHomo sapiens (human)
protein homodimerization activityTyrosinaseHomo sapiens (human)
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 (18)

Processvia Protein(s)Taxonomy
cytoplasmTyrosinaseHomo sapiens (human)
lysosomeTyrosinaseHomo sapiens (human)
Golgi-associated vesicleTyrosinaseHomo sapiens (human)
melanosome membraneTyrosinaseHomo sapiens (human)
melanosomeTyrosinaseHomo sapiens (human)
intracellular membrane-bounded organelleTyrosinaseHomo sapiens (human)
perinuclear region of cytoplasmTyrosinaseHomo sapiens (human)
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 (20)

Assay IDTitleYearJournalArticle
AID471934Antitumor activity against human SF268 cells assessed as inhibition of growth after 48 hrs using sulforhodamine B dye2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Bromoalkoxyxanthones as promising antitumor agents: synthesis, crystal structure and effect on human tumor cell lines.
AID403704Inhibition of human COX2 expressed in sf9 cells2005Journal of natural products, Oct, Volume: 68, Issue:10
Selective cyclooxygenase-2 inhibitors from Calophyllum membranaceum.
AID1683487Inhibition of Tyrosinase (unknown origin) at 150 uM using tyrosine as substrate incubated for 20 mins followed by substrate addition and measured every 10 mins for 30 mins relative to control2021Bioorganic & medicinal chemistry, 01-01, Volume: 29Xanthones for melanogenesis inhibition: Molecular docking and QSAR studies to understand their anti-tyrosinase activity.
AID1357644Cytotoxicity against mouse 3T3L1 cells at 50 uM after 48 hrs by sulforhodamine B assay2018European journal of medicinal chemistry, May-10, Volume: 151Lipid reducing activity and toxicity profiles of a library of polyphenol derivatives.
AID471932Antitumor activity against human MCF7 cells expressing estrogen receptor assessed as inhibition of growth after 48 hrs using sulforhodamine B dye2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Bromoalkoxyxanthones as promising antitumor agents: synthesis, crystal structure and effect on human tumor cell lines.
AID1683488Inhibition of Hyaluronidase (unknown origin) at 9.4 to 150 uM using hyaluronic acid as substrate incubated for 20 mins followed by substrate addition and measured after 40 mins2021Bioorganic & medicinal chemistry, 01-01, Volume: 29Xanthones for melanogenesis inhibition: Molecular docking and QSAR studies to understand their anti-tyrosinase activity.
AID1357647Lipid lowering activity in zebrafish embryos at 5 uM by Nile red fat metabolism assay2018European journal of medicinal chemistry, May-10, Volume: 151Lipid reducing activity and toxicity profiles of a library of polyphenol derivatives.
AID403703Inhibition of human COX1 expressed in sf9 cells2005Journal of natural products, Oct, Volume: 68, Issue:10
Selective cyclooxygenase-2 inhibitors from Calophyllum membranaceum.
AID1478622Antiproliferative activity against human MDA-MB-231 cells after 48 hrs by CCK8 assay2017European journal of medicinal chemistry, Jun-16, Volume: 133Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them.
AID1478625Antiproliferative activity against human K562 cells after 48 hrs by CCK8 assay2017European journal of medicinal chemistry, Jun-16, Volume: 133Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them.
AID1357643Cytotoxicity against mouse 3T3L1 cells at 50 uM after 24 hrs by sulforhodamine B assay2018European journal of medicinal chemistry, May-10, Volume: 151Lipid reducing activity and toxicity profiles of a library of polyphenol derivatives.
AID471931Antitumor activity against human NCI-H460 cells assessed as inhibition of growth after 48 hrs using sulforhodamine B dye2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Bromoalkoxyxanthones as promising antitumor agents: synthesis, crystal structure and effect on human tumor cell lines.
AID1478623Antiproliferative activity against human MCF7 cells after 48 hrs by CCK8 assay2017European journal of medicinal chemistry, Jun-16, Volume: 133Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them.
AID471933Antitumor activity against human estrogen receptor deficient MDA-MB-231 cells assessed as inhibition of growth after 48 hrs using sulforhodamine B dye2009European journal of medicinal chemistry, Sep, Volume: 44, Issue:9
Bromoalkoxyxanthones as promising antitumor agents: synthesis, crystal structure and effect on human tumor cell lines.
AID1478626Antiproliferative activity against human COLO320 cells after 48 hrs by CCK8 assay2017European journal of medicinal chemistry, Jun-16, Volume: 133Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them.
AID1683485Inhibition of Elastase (unknown origin) at 150 uM using N-methoxysuccinyl-Ala-Ala-Pro-Val-p-nitroanilide as substrate at 150 uM incubated for 20 mins followed by substrate addition and measured after 40 mins relative to control2021Bioorganic & medicinal chemistry, 01-01, Volume: 29Xanthones for melanogenesis inhibition: Molecular docking and QSAR studies to understand their anti-tyrosinase activity.
AID1357641Toxicity in zebra fish larvae at 5 uM after 48 hrs2018European journal of medicinal chemistry, May-10, Volume: 151Lipid reducing activity and toxicity profiles of a library of polyphenol derivatives.
AID1683483Inhibition of Collagenase (unknown origin) using FALGPA as substrate at 150 uM incubated for 20 mins followed by substrate addition and measured after 60 mins relative to control2021Bioorganic & medicinal chemistry, 01-01, Volume: 29Xanthones for melanogenesis inhibition: Molecular docking and QSAR studies to understand their anti-tyrosinase activity.
AID1683486Inhibition of Tyrosinase (unknown origin) using tyrosine as substrate incubated for 20 mins followed by substrate addition and measured every 10 mins for 30 mins2021Bioorganic & medicinal chemistry, 01-01, Volume: 29Xanthones for melanogenesis inhibition: Molecular docking and QSAR studies to understand their anti-tyrosinase activity.
AID1478624Antiproliferative activity against human HepG2 cells after 48 hrs by CCK8 assay2017European journal of medicinal chemistry, Jun-16, Volume: 133Synthesis of xanthone derivatives and studies on the inhibition against cancer cells growth and synergistic combinations of them.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (16.67)18.2507
2000's2 (33.33)29.6817
2010's2 (33.33)24.3611
2020's1 (16.67)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.85

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 Index12.85 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.80 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.85)

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%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]