Page last updated: 2024-11-06

2-Methoxyxanthone

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

2-Methoxyxanthone is a naturally occurring compound found in various plants, including the genus Gentiana. It exhibits a range of biological activities, including antioxidant, anti-inflammatory, and anticancer properties. Research has shown that 2-methoxyxanthone possesses significant inhibitory activity against the enzyme α-glucosidase, which is involved in the breakdown of carbohydrates. This makes it a potential therapeutic target for the management of type 2 diabetes. Furthermore, studies have indicated its potential as an antimicrobial agent against certain bacteria and fungi. The compound is also being investigated for its potential in the treatment of neurological disorders, such as Alzheimer's disease. Due to its diverse biological activities and promising therapeutic potential, 2-methoxyxanthone has garnered significant interest in the scientific community. Several synthetic routes have been developed for its production, allowing for further exploration of its medicinal properties.'

Cross-References

ID SourceID
PubMed CID71034
CHEMBL ID186609
CHEBI ID169168
SCHEMBL ID394209

Synonyms (42)

Synonym
2-methoxyxanthone
CHEBI:169168
BRD-K02855712-001-02-5
SPECTRUM_000120
SPECTRUM4_001601
SPECTRUM5_000321
BSPBIO_003041
NCGC00178333-01
KUC102603N
2-methoxy-9h-xanthen-9-one
MLS000859019
smr000459198
KBIO2_003128
KBIO2_000560
KBIOGR_001941
KBIO3_002261 ,
KBIOSS_000560
KBIO2_005696
SPBIO_000410
SPECTRUM3_001321
SPECTRUM2_000425
MLS001143195 ,
inchi=1/c14h10o3/c1-16-9-6-7-13-11(8-9)14(15)10-4-2-3-5-12(10)17-13/h2-8h,1h
2-methoxyxanthen-9-one
1214-20-6
bdbm50155417
2-methoxy-xanthen-9-one
CHEMBL186609 ,
9h-xanthen-9-one, 2-methoxy-
9h-xanthen-9-one,2-methoxy-
HMS2203P05
CCG-40234
HMS3356B16
7-methoxyxanthone
mfcd01312686
SCHEMBL394209
2-methoxy-9h-xanthen-9-one #
xanthen-9-one, 2-methoxy-
DTXSID10153258
2-methoxyxanthen-9-one, aldrichcpr
BRD-K02855712-001-06-6
3-(8-chloroquinoline-4-yl)acrylicacid
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
xanthonesAny member of the class of xanthenes based on a xanthone skeleton.
[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]

Protein Targets (10)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
acid sphingomyelinaseHomo sapiens (human)Potency31.622814.125424.061339.8107AID504937
Nrf2Homo sapiens (human)Potency13.86710.09208.222223.1093AID624171; AID651593; AID651597
thioredoxin reductaseRattus norvegicus (Norway rat)Potency56.23410.100020.879379.4328AID588456
BRCA1Homo sapiens (human)Potency22.38720.89137.722525.1189AID624202
chromobox protein homolog 1Homo sapiens (human)Potency89.12510.006026.168889.1251AID540317
nuclear factor erythroid 2-related factor 2 isoform 2Homo sapiens (human)Potency20.59620.00419.984825.9290AID504444
tumor susceptibility gene 101 proteinHomo sapiens (human)Potency53.73120.129810.833132.6090AID493005; AID651599
gemininHomo sapiens (human)Potency6.51310.004611.374133.4983AID624297
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
TyrosinaseHomo sapiens (human)IC50 (µMol)8.47000.02304.459310.0000AID1683486
Amine oxidase [flavin-containing] AHomo sapiens (human)IC50 (µMol)5.30000.00002.37899.7700AID240726
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (14)

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)
biogenic amine metabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
positive regulation of signal transductionAmine oxidase [flavin-containing] AHomo sapiens (human)
dopamine catabolic processAmine oxidase [flavin-containing] AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (9)

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)
protein bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
monoamine oxidase activityAmine oxidase [flavin-containing] AHomo sapiens (human)
flavin adenine dinucleotide bindingAmine oxidase [flavin-containing] AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (10)

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)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrial outer membraneAmine oxidase [flavin-containing] AHomo sapiens (human)
cytosolAmine oxidase [flavin-containing] AHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (32)

Assay IDTitleYearJournalArticle
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.
AID633113Antibacterial activity against Bacillus cereus ATCC 117782011Bioorganic & medicinal chemistry letters, Dec-01, Volume: 21, Issue:23
The synthesis of xanthones, xanthenediones, and spirobenzofurans: their antibacterial and antifungal activity.
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.
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.
AID633114Antibacterial activity against Staphylococcus aureus ATCC 25872011Bioorganic & medicinal chemistry letters, Dec-01, Volume: 21, Issue:23
The synthesis of xanthones, xanthenediones, and spirobenzofurans: their antibacterial and antifungal 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.
AID240726Concentration required to inhibit monoamine oxidase activity by 50%2004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
QSAR modeling of the MAO inhibitory activity of xanthones 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.
AID633116Antibacterial activity against Moraxella catarrhalis ATCC 2324462011Bioorganic & medicinal chemistry letters, Dec-01, Volume: 21, Issue:23
The synthesis of xanthones, xanthenediones, and spirobenzofurans: their antibacterial and antifungal activity.
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.
AID633117Antifungal activity against Cryptococcus neoformans ATCC 901122011Bioorganic & medicinal chemistry letters, Dec-01, Volume: 21, Issue:23
The synthesis of xanthones, xanthenediones, and spirobenzofurans: their antibacterial and antifungal 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.
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.
AID633118Antifungal activity against Candida albicans ATCC 102312011Bioorganic & medicinal chemistry letters, Dec-01, Volume: 21, Issue:23
The synthesis of xanthones, xanthenediones, and spirobenzofurans: their antibacterial and antifungal activity.
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.
AID633115Antibacterial activity against Escherichia coli ATCC 87392011Bioorganic & medicinal chemistry letters, Dec-01, Volume: 21, Issue:23
The synthesis of xanthones, xanthenediones, and spirobenzofurans: their antibacterial and antifungal activity.
AID1745845Primary qHTS for Inhibitors of ATXN expression
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.
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.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
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.
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.
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).
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 (12)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (16.67)29.6817
2010's7 (58.33)24.3611
2020's3 (25.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.98

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 Index11.98 (24.57)
Research Supply Index2.56 (2.92)
Research Growth Index4.54 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.98)

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%
Other12 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]