Compounds > xanthoxyletin

Page last updated: 2024-12-06

xanthoxyletin

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

Description

Xanthoxyletin is a natural coumarin derivative found in various plants, particularly in the Rutaceae family. It exhibits a range of biological activities, including antioxidant, anti-inflammatory, and anticancer properties. Its synthesis has been explored through various methods, often involving natural sources like the fruits of Xanthoxylum species. Research into xanthoxyletin is driven by its potential therapeutic applications. For instance, studies have investigated its effects on cell proliferation, apoptosis, and the inhibition of tumor growth. The compound's ability to modulate signaling pathways involved in inflammation and oxidative stress makes it a promising target for the development of new drugs. The complexity of its biological mechanisms and its potential medicinal value continue to drive scientific interest in xanthoxyletin.'

xanthoxyletin: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	66548
CHEMBL ID	501358
CHEBI ID	69929
SCHEMBL ID	5793283
MeSH ID	M0454079

Synonyms (39)

Synonym
5-methoxy-8,8-dimethyl-2h,8h-pyrano[3,2-g]chromen-2-one
5-methoxy-2,2-dimethyl-pyrano[3,2-g]chromen-8-one
2h,2-b:5,4-b']dipyran-2-one, 5-methoxy-8,8-dimethyl-
xanthoxylin n
84-99-1
xanthoxyletin
2-propenoic acid,2-dimethyl-2h-1-benzopyran-6-yl)-, .delta.-lactone
nsc-35542
nsc35542
NCI60_003203
MEGXP0_001370
ACON1_000545
MLS000876794
smr000440571
NCGC00168976-01
BRD-K28556256-001-01-3
5-methoxy-2,2-dimethylpyrano[3,2-g]chromen-8-one
chebi:69929 ,
CHEMBL501358
2h,8h-benzo(1,2-b:5,4-b')dipyran-2-one, 5-methoxy-8,8-dimethyl-
69mpx4m5vd ,
nsc 35542
unii-69mpx4m5vd
bdbm50428432
HMS2269F07
xanthoxyloin
xanthoxyletin [mi]
7-hydroxy-5-methoxy-2,2-dimethyl-2h-1-benzopyran-6-acrylic acid .delta.-lactone
SCHEMBL5793283
DTXSID70232891
5-methoxy-8,8-dimethyl-2h,8h-benzo[1,2-b:5,4-b']dipyran-2-one,9ci
ncgc00168976-02!5-methoxy-2,2-dimethylpyrano[3,2-g]chromen-8-one
AKOS032962595
Q27138273
FS-8762
nsc 35542; xanthoxylin n
XX163678
CS-0016348
HY-N1065

Research Excerpts

Treatment

Excerpt	Reference	Relevance
"Xanthoxyletin treatment was associated with G2/M arrest of the cell cycle and with increased apoptosis and autophagy of SCC-1 cells."	( Xanthoxyletin Inhibits Proliferation of Human Oral Squamous Carcinoma Cells and Induces Apoptosis, Autophagy, and Cell Cycle Arrest by Modulation of the MEK/ERK Signaling Pathway. Huang, H; Liao, W; Luo, K; Wen, Q; Yang, H, 2019)	2.68

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

Role	Description
metabolite	Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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 (1)

Class	Description
coumarins
[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 (17)

Potency Measurements

Protein	Taxonomy	Measurement	Average (µ)	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Chain A, 2-oxoglutarate Oxygenase	Homo sapiens (human)	Potency	31.6228	0.1778	14.3909	39.8107	AID2147
Luciferase	Photinus pyralis (common eastern firefly)	Potency	16.9441	0.0072	15.7588	89.3584	AID588342
acid sphingomyelinase	Homo sapiens (human)	Potency	25.1189	14.1254	24.0613	39.8107	AID504937
glp-1 receptor, partial	Homo sapiens (human)	Potency	13.3573	0.0184	6.8060	14.1254	AID624172; AID624417
ATAD5 protein, partial	Homo sapiens (human)	Potency	23.0999	0.0041	10.8903	31.5287	AID504467
TDP1 protein	Homo sapiens (human)	Potency	18.7556	0.0008	11.3822	44.6684	AID686978; AID686979
euchromatic histone-lysine N-methyltransferase 2	Homo sapiens (human)	Potency	1.4125	0.0355	20.9770	89.1251	AID504332
chromobox protein homolog 1	Homo sapiens (human)	Potency	100.0000	0.0060	26.1688	89.1251	AID540317
nuclear factor erythroid 2-related factor 2 isoform 2	Homo sapiens (human)	Potency	7.3078	0.0041	9.9848	25.9290	AID504444
nuclear receptor ROR-gamma isoform 1	Mus musculus (house mouse)	Potency	14.1254	0.0079	8.2332	1,122.0200	AID2546
TAR DNA-binding protein 43	Homo sapiens (human)	Potency	12.5893	1.7783	16.2081	35.4813	AID652104
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Carbonic anhydrase 12	Homo sapiens (human)	Ki	0.9600	0.0002	1.1043	9.9000	AID729559
Carbonic anhydrase 1	Homo sapiens (human)	Ki	7.7100	0.0000	1.3726	10.0000	AID729563
Carbonic anhydrase 2	Homo sapiens (human)	Ki	100.0000	0.0000	0.7236	9.9200	AID729562
Carbonic anhydrase 7	Homo sapiens (human)	Ki	6.2700	0.0002	1.3737	9.9000	AID729561
Carbonic anhydrase 9	Homo sapiens (human)	Ki	0.7400	0.0001	0.7874	9.9000	AID729560
Carbonic anhydrase 13	Homo sapiens (human)	Ki	3.1500	0.0003	1.2309	9.8000	AID729558
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (35)

Process	via Protein(s)	Taxonomy
estrous cycle	Carbonic anhydrase 12	Homo sapiens (human)
chloride ion homeostasis	Carbonic anhydrase 12	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 12	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 1	Homo sapiens (human)
morphogenesis of an epithelium	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of synaptic transmission, GABAergic	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of cellular pH reduction	Carbonic anhydrase 2	Homo sapiens (human)
angiotensin-activated signaling pathway	Carbonic anhydrase 2	Homo sapiens (human)
regulation of monoatomic anion transport	Carbonic anhydrase 2	Homo sapiens (human)
secretion	Carbonic anhydrase 2	Homo sapiens (human)
regulation of intracellular pH	Carbonic anhydrase 2	Homo sapiens (human)
neuron cellular homeostasis	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of dipeptide transmembrane transport	Carbonic anhydrase 2	Homo sapiens (human)
regulation of chloride transport	Carbonic anhydrase 2	Homo sapiens (human)
carbon dioxide transport	Carbonic anhydrase 2	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 2	Homo sapiens (human)
positive regulation of synaptic transmission, GABAergic	Carbonic anhydrase 7	Homo sapiens (human)
positive regulation of cellular pH reduction	Carbonic anhydrase 7	Homo sapiens (human)
neuron cellular homeostasis	Carbonic anhydrase 7	Homo sapiens (human)
regulation of chloride transport	Carbonic anhydrase 7	Homo sapiens (human)
regulation of intracellular pH	Carbonic anhydrase 7	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 7	Homo sapiens (human)
negative regulation of protein phosphorylation	TAR DNA-binding protein 43	Homo sapiens (human)
mRNA processing	TAR DNA-binding protein 43	Homo sapiens (human)
RNA splicing	TAR DNA-binding protein 43	Homo sapiens (human)
negative regulation of gene expression	TAR DNA-binding protein 43	Homo sapiens (human)
regulation of protein stability	TAR DNA-binding protein 43	Homo sapiens (human)
positive regulation of insulin secretion	TAR DNA-binding protein 43	Homo sapiens (human)
response to endoplasmic reticulum stress	TAR DNA-binding protein 43	Homo sapiens (human)
positive regulation of protein import into nucleus	TAR DNA-binding protein 43	Homo sapiens (human)
regulation of circadian rhythm	TAR DNA-binding protein 43	Homo sapiens (human)
regulation of apoptotic process	TAR DNA-binding protein 43	Homo sapiens (human)
negative regulation by host of viral transcription	TAR DNA-binding protein 43	Homo sapiens (human)
rhythmic process	TAR DNA-binding protein 43	Homo sapiens (human)
regulation of cell cycle	TAR DNA-binding protein 43	Homo sapiens (human)
3'-UTR-mediated mRNA destabilization	TAR DNA-binding protein 43	Homo sapiens (human)
3'-UTR-mediated mRNA stabilization	TAR DNA-binding protein 43	Homo sapiens (human)
nuclear inner membrane organization	TAR DNA-binding protein 43	Homo sapiens (human)
amyloid fibril formation	TAR DNA-binding protein 43	Homo sapiens (human)
regulation of gene expression	TAR DNA-binding protein 43	Homo sapiens (human)
response to hypoxia	Carbonic anhydrase 9	Homo sapiens (human)
morphogenesis of an epithelium	Carbonic anhydrase 9	Homo sapiens (human)
response to xenobiotic stimulus	Carbonic anhydrase 9	Homo sapiens (human)
response to testosterone	Carbonic anhydrase 9	Homo sapiens (human)
secretion	Carbonic anhydrase 9	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 9	Homo sapiens (human)
one-carbon metabolic process	Carbonic anhydrase 13	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Process	via Protein(s)	Taxonomy
zinc ion binding	Carbonic anhydrase 12	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 12	Homo sapiens (human)
arylesterase activity	Carbonic anhydrase 1	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 1	Homo sapiens (human)
protein binding	Carbonic anhydrase 1	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 1	Homo sapiens (human)
hydro-lyase activity	Carbonic anhydrase 1	Homo sapiens (human)
cyanamide hydratase activity	Carbonic anhydrase 1	Homo sapiens (human)
arylesterase activity	Carbonic anhydrase 2	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 2	Homo sapiens (human)
protein binding	Carbonic anhydrase 2	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 2	Homo sapiens (human)
cyanamide hydratase activity	Carbonic anhydrase 2	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 7	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 7	Homo sapiens (human)
RNA polymerase II cis-regulatory region sequence-specific DNA binding	TAR DNA-binding protein 43	Homo sapiens (human)
DNA binding	TAR DNA-binding protein 43	Homo sapiens (human)
double-stranded DNA binding	TAR DNA-binding protein 43	Homo sapiens (human)
RNA binding	TAR DNA-binding protein 43	Homo sapiens (human)
mRNA 3'-UTR binding	TAR DNA-binding protein 43	Homo sapiens (human)
protein binding	TAR DNA-binding protein 43	Homo sapiens (human)
lipid binding	TAR DNA-binding protein 43	Homo sapiens (human)
identical protein binding	TAR DNA-binding protein 43	Homo sapiens (human)
pre-mRNA intronic binding	TAR DNA-binding protein 43	Homo sapiens (human)
molecular condensate scaffold activity	TAR DNA-binding protein 43	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 9	Homo sapiens (human)
protein binding	Carbonic anhydrase 9	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 9	Homo sapiens (human)
molecular function activator activity	Carbonic anhydrase 9	Homo sapiens (human)
protein binding	Carbonic anhydrase 13	Homo sapiens (human)
zinc ion binding	Carbonic anhydrase 13	Homo sapiens (human)
carbonate dehydratase activity	Carbonic anhydrase 13	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (21)

Process	via Protein(s)	Taxonomy
plasma membrane	Carbonic anhydrase 12	Homo sapiens (human)
membrane	Carbonic anhydrase 12	Homo sapiens (human)
basolateral plasma membrane	Carbonic anhydrase 12	Homo sapiens (human)
apical plasma membrane	Carbonic anhydrase 12	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 12	Homo sapiens (human)
cytosol	Carbonic anhydrase 1	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 1	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 2	Homo sapiens (human)
cytosol	Carbonic anhydrase 2	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 2	Homo sapiens (human)
myelin sheath	Carbonic anhydrase 2	Homo sapiens (human)
apical part of cell	Carbonic anhydrase 2	Homo sapiens (human)
extracellular exosome	Carbonic anhydrase 2	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 2	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 2	Homo sapiens (human)
apical part of cell	Carbonic anhydrase 2	Homo sapiens (human)
cytosol	Carbonic anhydrase 7	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 7	Homo sapiens (human)
intracellular non-membrane-bounded organelle	TAR DNA-binding protein 43	Homo sapiens (human)
nucleus	TAR DNA-binding protein 43	Homo sapiens (human)
nucleoplasm	TAR DNA-binding protein 43	Homo sapiens (human)
perichromatin fibrils	TAR DNA-binding protein 43	Homo sapiens (human)
mitochondrion	TAR DNA-binding protein 43	Homo sapiens (human)
cytoplasmic stress granule	TAR DNA-binding protein 43	Homo sapiens (human)
nuclear speck	TAR DNA-binding protein 43	Homo sapiens (human)
interchromatin granule	TAR DNA-binding protein 43	Homo sapiens (human)
nucleoplasm	TAR DNA-binding protein 43	Homo sapiens (human)
chromatin	TAR DNA-binding protein 43	Homo sapiens (human)
nucleolus	Carbonic anhydrase 9	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 9	Homo sapiens (human)
membrane	Carbonic anhydrase 9	Homo sapiens (human)
basolateral plasma membrane	Carbonic anhydrase 9	Homo sapiens (human)
microvillus membrane	Carbonic anhydrase 9	Homo sapiens (human)
plasma membrane	Carbonic anhydrase 9	Homo sapiens (human)
cytosol	Carbonic anhydrase 13	Homo sapiens (human)
myelin sheath	Carbonic anhydrase 13	Homo sapiens (human)
intracellular membrane-bounded organelle	Carbonic anhydrase 13	Homo sapiens (human)
cytoplasm	Carbonic anhydrase 13	Homo sapiens (human)
cytosol	Carbonic anhydrase 13	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (34)

Assay ID	Title	Year	Journal	Article
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2006	Cytometry. 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.
AID588499	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2006	Cytometry. 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.
AID588501	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504810	Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Current protocols in cytometry, Oct, Volume: Chapter 13	Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2006	Cytometry. 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.
AID588497	High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set	2010	Assay and drug development technologies, Feb, Volume: 8, Issue:1	High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845	Primary qHTS for Inhibitors of ATXN expression
AID651635	Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID504812	Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign	2010	Endocrinology, Jul, Volume: 151, Issue:7	A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID400457	Antimicrobial activity against Sarcina lutea 9341 at 500 ppm after 24 hrs
AID400476	Antimicrobial activity against penicillin-resistant Staphylococcus aureus at 500 ppm after 24 hrs
AID587893	Cytotoxicity against human NCI-H187 by resazurin microplate assay	2011	Journal of natural products, Feb-25, Volume: 74, Issue:2	Claurailas A-D, cytotoxic carbazole alkaloids from the roots of Clausena harmandiana.
AID400474	Antimicrobial activity against Aspergillus niger at 500 ppm after 24 hrs
AID400468	Antimicrobial activity against Saccharomyces carlsbergensis at 500 ppm after 24 hrs
AID587894	Cytotoxicity against african green monkey Vero cells by green fluorescent protein microplate assay	2011	Journal of natural products, Feb-25, Volume: 74, Issue:2	Claurailas A-D, cytotoxic carbazole alkaloids from the roots of Clausena harmandiana.
AID729559	Inhibition of human carbonic anhydrase 12 preincubated for 6 hrs by CO2 hydration stopped-flow assay	2013	Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6	Natural product coumarins that inhibit human carbonic anhydrases.
AID400188	Antimicrobial activity against Bordetella bronchiseptica 4614 at 500 ppm after 24 hrs
AID400200	Antimicrobial activity against Escherichia coli 10536 at 500 ppm after 24 hrs
AID729563	Inhibition of human carbonic anhydrase 1 preincubated for 6 hrs by CO2 hydration stopped-flow assay	2013	Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6	Natural product coumarins that inhibit human carbonic anhydrases.
AID587892	Cytotoxicity against human KB cells by resazurin microplate assay	2011	Journal of natural products, Feb-25, Volume: 74, Issue:2	Claurailas A-D, cytotoxic carbazole alkaloids from the roots of Clausena harmandiana.
AID729560	Inhibition of human carbonic anhydrase 9 preincubated for 6 hrs by CO2 hydration stopped-flow assay	2013	Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6	Natural product coumarins that inhibit human carbonic anhydrases.
AID400442	Antimicrobial activity against Bacillus subtilis 6633 at 500 ppm after 24 hrs
AID729561	Inhibition of human carbonic anhydrase 7 preincubated for 6 hrs by CO2 hydration stopped-flow assay	2013	Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6	Natural product coumarins that inhibit human carbonic anhydrases.
AID400194	Antimicrobial activity against Salmonella gallinarum X142 at 500 ppm after 24 hrs
AID729558	Inhibition of human carbonic anhydrase 13 preincubated for 6 hrs by CO2 hydration stopped-flow assay	2013	Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6	Natural product coumarins that inhibit human carbonic anhydrases.
AID431552	Antiviral activity against Hepatitis B virus infected in human Hep2A cells assessed as suppression of viral surface antigen production upto 15 uM after 48 hrs by enzyme immunoassay	2009	Bioorganic & medicinal chemistry, Aug-15, Volume: 17, Issue:16	Anti-HBV and cytotoxic activities of pyranocoumarin derivatives.
AID400452	Antimicrobial activity against Staphylococcus aureus 6538-P at 500 ppm after 24 hrs
AID400462	Antimicrobial activity against Pseudomonas aeruginosa NCTC 10490 at 500 ppm after 24 hrs
AID400447	Antimicrobial activity against Pneumococcus clinical isolates at 500 ppm after 24 hrs
AID729562	Inhibition of human carbonic anhydrase 2 preincubated for 6 hrs by CO2 hydration stopped-flow assay	2013	Bioorganic & medicinal chemistry, Mar-15, Volume: 21, Issue:6	Natural product coumarins that inhibit human carbonic anhydrases.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (14)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	4 (28.57)	29.6817
2010's	8 (57.14)	24.3611
2020's	2 (14.29)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 16.91

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.

Metric	This Compound (vs All)
Research Demand Index	16.91 (24.57)
Research Supply Index	2.77 (2.92)
Research Growth Index	4.50 (4.65)
Search Engine Demand Index	10.37 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (16.91)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	15 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
coumarin 2H-chromen-2-one: coumarin derivative	2.08	1	coumarins	fluorescent dye; human metabolite; plant metabolite
ellipticine ellipticine : A organic heterotetracyclic compound that is pyrido[4,3-b]carbazole carrying two methyl substituents at positions 5 and 11.	2.06	1	indole alkaloid; organic heterotetracyclic compound; organonitrogen heterocyclic compound; polycyclic heteroarene	antineoplastic agent; plant metabolite
calanolide b calanolide B: structure given in first source; one of a novel class of HIV-inhibiting coumarins from the tropical rainforest tree, Calophyllum lanigerum	2.08	1
xanthyletine xanthyletine: structure	2.44	2	coumarins
isopimpinellin isopimpinellin: from Ruta graveolens & Heracleum lanatum; structure	2.01	1	psoralens
seselin seselin: structure in first source	7.15	1	coumarins	metabolite
isoscopoletin isoscopoletin : A hydroxycoumarin that is esculetin in which the hydroxy group at position 7 is replaced by a methoxy group. It is the major primary metabolite of scoparone.	2.08	1	aromatic ether; hydroxycoumarin	plant metabolite
murrayanine murrayanine: carbazole alkaloid from Murraya koenigii; structure in first source	2.06	1	carbazoles	metabolite
girinimbine girinimbine: carbazole alkaloid	2.06	1	carbazoles	metabolite
7-methoxyheptaphylline 7-methoxyheptaphylline: cytotoxic carbazole alkaloid from the roots of Clausena harmandiana; structure in first source	2.06	1	carbazoles	metabolite
dentatin dentatin: from Clausena excavata; structure in first source	2.46	2	coumarins	metabolite
scopolin [no description available]	2.08	1	beta-D-glucoside; coumarins; monosaccharide derivative	plant metabolite
6,7,8-trimethoxycoumarin 6,7,8-trimethoxycoumarin: structure in first source	2.08	1	coumarins
fraxin fraxin: found in Fraxinus excelsior leaves; structure given in first source. fraxin : A beta-D-glucoside that is fraxetin attached to a beta-D-glucopyranosyl group at position 8 via a glycosidic linkage. It is a natural product isolated from the leaves of Fraxinus excelsior and exhibits potent hepatoprotective effects in vitro and in vivo.	2.08	1	aromatic ether; beta-D-glucoside; hydroxycoumarin	anti-inflammatory agent; hepatoprotective agent; plant metabolite
fraxetin fraxetin : A hydroxycoumarin that is 6-methoxycoumarin in which the hydrogens at positions 7 and 8 have been replaced by hydroxy groups.	2.08	1	aromatic ether; hydroxycoumarin	anti-inflammatory agent; antibacterial agent; antimicrobial agent; antioxidant; apoptosis inducer; apoptosis inhibitor; Arabidopsis thaliana metabolite; hepatoprotective agent; hypoglycemic agent
scopoletin [no description available]	2.08	1	hydroxycoumarin	plant growth regulator; plant metabolite
ellagic acid [no description available]	2.08	1	catechols; cyclic ketone; lactone; organic heterotetracyclic compound; polyphenol	antioxidant; EC 1.14.18.1 (tyrosinase) inhibitor; EC 2.3.1.5 (arylamine N-acetyltransferase) inhibitor; EC 2.4.1.1 (glycogen phosphorylase) inhibitor; EC 2.5.1.18 (glutathione transferase) inhibitor; EC 2.7.1.127 (inositol-trisphosphate 3-kinase) inhibitor; EC 2.7.1.151 (inositol-polyphosphate multikinase) inhibitor; EC 2.7.4.6 (nucleoside-diphosphate kinase) inhibitor; EC 2.7.7.7 (DNA-directed DNA polymerase) inhibitor; EC 5.99.1.2 (DNA topoisomerase) inhibitor; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; food additive; fungal metabolite; geroprotector; plant metabolite; skin lightening agent
clausarin clausarin: isolated from Enkleia siamensis; structure given in first source	2.05	1
clausine e clausine E: structure in first source	2.06	1	carbazoles	metabolite
heptaphylline heptaphylline: cytotoxic carbazole alkaloid from the roots of Clausena harmandiana; structure in first source	2.06	1	carbazoles	metabolite
geiparvarin geiparvarin: from Geijera parviflora; structure given in first source	2.08	1
trans-avicennol trans-avicennol: from Zanthoxylum chiloperone var. angustifolium; structure in first source	2.08	1
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.	3.33	6	benzenes; hydroxycoumarin; methyl ketone

Condition	Relationship Strength	Studies
Innate Inflammatory Response [description not available]	2.05	1
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.	2.05	1
Cancer of Pancreas [description not available]	3.52	4
Pancreatic Neoplasms Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).	3.52	4
Carcinoma, Epidermoid [description not available]	2.21	1
Cancer of Mouth [description not available]	2.21	1
Carcinoma, Squamous Cell A carcinoma derived from stratified SQUAMOUS EPITHELIAL CELLS. It may also occur in sites where glandular or columnar epithelium is normally present. (From Stedman, 25th ed)	2.21	1
Mouth Neoplasms Tumors or cancer of the MOUTH.	2.21	1
Adenocarcinoma, Basal Cell [description not available]	2.06	1
Cancer of Stomach [description not available]	2.06	1
Adenocarcinoma A malignant epithelial tumor with a glandular organization.	7.06	1
Stomach Neoplasms Tumors or cancer of the STOMACH.	2.06	1

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