Page last updated: 2024-12-06

xanthotoxol

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Description

8-hydroxyfurocoumarin : A furanocoumarin which bears a hydroxy group at position 8. [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 CID65090
CHEMBL ID1192
CHEBI ID15709
SCHEMBL ID499269
MeSH IDM0077070

Synonyms (69)

Synonym
AC-12979
CHEBI:15709 ,
7h-furo(3,2-g)(1)benzopyran-7-one, 9-hydroxy-
5-benzofuranacrylic acid, 6,7-dihydroxy-, gamma-lactone
einecs 217-923-1
9-hydroxy-7h-furo(3,2-g)(1)benzopyran-7-one
brn 0189491
nsc 401269
6,7-dihydroxy-5-benzofuranacrylic acid gamma-lactone
7h-furo[3,2-g][1]benzopyran-7-one, 9-hydroxy-
9-hydroxy-7h-furo[3,2-g]chromen-7-one
inchi=1/c11h6o4/c12-8-2-1-6-5-7-3-4-14-10(7)9(13)11(6)15-8/h1-5,13
7h-furo[3, 9-hydroxy-
psoralen, 8-hydroxy-
nsc-401269
2-propenoic acid,7-dihydroxy-5-benzofuranyl)-, .delta.-lactone
8-hydroxyfuranocoumarin
2009-24-7
xanthotoxol
C00841
8-hydroxypsoralen
NSC401269 ,
8-hydroxypsoralene
9-hydroxyfuro[3,2-g]chromen-7-one
8-hydroxyfurocoumarin
8-hydroxyfuranocoumarins
8-hydroxyfurocoumarins ,
an 8-hydroxyfurocoumarin
MLS002472938
smr001397046
AKOS000276803
CHEMBL1192
xanthoxol
NCGC00247457-01
9-hydroxy-furo[3,2-g]chromen-7-one
HMS2267B05
S9174
5-19-06-00014 (beilstein handbook reference)
unii-8rl486l8a5
8rl486l8a5 ,
bdbm50361378
FT-0633974
9-hydroxy-7h-furo[3,2-g][1]benzopyran-7-one
mfcd00017408
SCHEMBL499269
W-201757
5-benzofuranacrylic acid, 6,7-dihydroxy-, .delta.-lactone
2-propenoic acid, 3-(6,7-dihydroxy-5-benzofuranyl)-, .delta.-lactone
9-hydroxy-7h-furo[3,2-g]chromen-7-one #
7h-furo[3,2-g][1]benzopyran-7-one,9-hydroxy-
AC-34294
HY-30152
CS-8023
DTXSID50173910
9-hydroxy-2h-furo[3,2-g]chromen-2-one
xanthotoxol (6ci)
xanthotol
8-hydroxy-psoralen
8-hydroxyanthotoxol
9-hydroxy-7h-furo[3,2-g][1]benzopyran-7-one, 9ci
Q4021722
6-(3,4-dichlorophenyl)-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole
A14771
HMS3886P18
CCG-266594
xanthotol; xanthotoxol
A879846
H10450
BS-21947

Research Excerpts

Overview

Xanthotoxol is a furanocoumarin that possesses many pharmacological activities. In this study its in vitro glucuronidation was studied.

ExcerptReferenceRelevance
"1. Xanthotoxol is a furanocoumarin that possesses many pharmacological activities and in this study its in vitro glucuronidation was studied. "( Identification and characterization of human UDP-glucuronosyltransferases responsible for xanthotoxol glucuronidation.
Finel, M; Ge, GB; He, G; Lv, X; Ning, J; Troberg, J; Xia, YL; Yang, L; Zhu, LL, 2018
)
1.32

Pharmacokinetics

ExcerptReferenceRelevance
" This study was aimed at investigating the effects of Acori Tatarinowii Rhizoma volatile oil on the pharmacokinetic parameters of xanthotoxol, oxypeucedanin hydrate, and byakangelicin from Angelicae Dahuricae Radix in rat, and in vitro absorption behavior of the three compounds using rat everted gut sac, in situ single-pass intestinal perfusion, and Caco-2 cell monolayer models."( Effect of co-administration of Acori Tatarinowii Rhizoma volatile oil on pharmacokinetic fate of xanthotoxol, oxypeucedanin hydrate, and byakangelicin from Angelicae Dahuricae Radix in rat.
Bian, L; Jia, P; Liu, J; Shi, B; Wang, S; Zhang, Q; Zheng, X, 2020
)
0.98
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
8-hydroxyfurocoumarinA furanocoumarin which bears a hydroxy group at position 8.
[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 (2)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
acid sphingomyelinaseHomo sapiens (human)Potency25.118914.125424.061339.8107AID504937
[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)
Beta-secretase 1Homo sapiens (human)IC50 (µMol)500.00000.00061.619410.0000AID637774
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (16)

Processvia Protein(s)Taxonomy
proteolysisBeta-secretase 1Homo sapiens (human)
membrane protein ectodomain proteolysisBeta-secretase 1Homo sapiens (human)
response to lead ionBeta-secretase 1Homo sapiens (human)
protein processingBeta-secretase 1Homo sapiens (human)
amyloid-beta formationBeta-secretase 1Homo sapiens (human)
amyloid precursor protein catabolic processBeta-secretase 1Homo sapiens (human)
positive regulation of neuron apoptotic processBeta-secretase 1Homo sapiens (human)
amyloid-beta metabolic processBeta-secretase 1Homo sapiens (human)
detection of mechanical stimulus involved in sensory perception of painBeta-secretase 1Homo sapiens (human)
prepulse inhibitionBeta-secretase 1Homo sapiens (human)
cellular response to copper ionBeta-secretase 1Homo sapiens (human)
cellular response to manganese ionBeta-secretase 1Homo sapiens (human)
presynaptic modulation of chemical synaptic transmissionBeta-secretase 1Homo sapiens (human)
signaling receptor ligand precursor processingBeta-secretase 1Homo sapiens (human)
cellular response to amyloid-betaBeta-secretase 1Homo sapiens (human)
amyloid fibril formationBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (8)

Processvia Protein(s)Taxonomy
amyloid-beta bindingBeta-secretase 1Homo sapiens (human)
endopeptidase activityBeta-secretase 1Homo sapiens (human)
aspartic-type endopeptidase activityBeta-secretase 1Homo sapiens (human)
protein bindingBeta-secretase 1Homo sapiens (human)
peptidase activityBeta-secretase 1Homo sapiens (human)
beta-aspartyl-peptidase activityBeta-secretase 1Homo sapiens (human)
enzyme bindingBeta-secretase 1Homo sapiens (human)
protein serine/threonine kinase bindingBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (20)

Processvia Protein(s)Taxonomy
lysosomeBeta-secretase 1Homo sapiens (human)
endosomeBeta-secretase 1Homo sapiens (human)
early endosomeBeta-secretase 1Homo sapiens (human)
late endosomeBeta-secretase 1Homo sapiens (human)
multivesicular bodyBeta-secretase 1Homo sapiens (human)
endoplasmic reticulum lumenBeta-secretase 1Homo sapiens (human)
Golgi apparatusBeta-secretase 1Homo sapiens (human)
trans-Golgi networkBeta-secretase 1Homo sapiens (human)
plasma membraneBeta-secretase 1Homo sapiens (human)
synaptic vesicleBeta-secretase 1Homo sapiens (human)
cell surfaceBeta-secretase 1Homo sapiens (human)
endosome membraneBeta-secretase 1Homo sapiens (human)
membraneBeta-secretase 1Homo sapiens (human)
axonBeta-secretase 1Homo sapiens (human)
dendriteBeta-secretase 1Homo sapiens (human)
neuronal cell bodyBeta-secretase 1Homo sapiens (human)
membrane raftBeta-secretase 1Homo sapiens (human)
recycling endosomeBeta-secretase 1Homo sapiens (human)
Golgi-associated vesicle lumenBeta-secretase 1Homo sapiens (human)
hippocampal mossy fiber to CA3 synapseBeta-secretase 1Homo sapiens (human)
endosomeBeta-secretase 1Homo sapiens (human)
plasma membraneBeta-secretase 1Homo sapiens (human)
trans-Golgi networkBeta-secretase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (46)

Assay IDTitleYearJournalArticle
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
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.
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.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID402909Cytotoxicity against human MS-G2 cells at 100 uM by MTT assay2004Journal of natural products, Jun, Volume: 67, Issue:6
Biotransformation of imperatorin by Aspergillus flavus.
AID456257Inhibition of human recombinant BACE1 at 100 to 500 uM after 60 mins by fluorescence assay2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Biotransformation of isoimperatorin and imperatorin by Glomerella cingulata and beta-secretase inhibitory activity.
AID402910Cytotoxicity against human MS-G2 cells at 50 uM by MTT assay2004Journal of natural products, Jun, Volume: 67, Issue:6
Biotransformation of imperatorin by Aspergillus flavus.
AID411504Anticorpulence activity against mouse 3T3L1 cells assessed as inhibition of lipid droplet accumulation2009Bioorganic & medicinal chemistry, Jan-01, Volume: 17, Issue:1
Identification and physiological evaluation of the components from citrus fruits as potential drugs for anti-corpulence and anticancer.
AID487718Antioxidant activity assessed as galvinoxyl radical scavenging activity measured up to 210 mins2010European journal of medicinal chemistry, Jun, Volume: 45, Issue:6
Synthesis of methyl-substituted xanthotoxol to clarify prooxidant effect of methyl on radical-induced oxidation of DNA.
AID402905Antiviral activity against hepatitis B virus infected in human MS-G2 cells assessed as inhibition of surface antigen production at 10 uM after 48 hrs2004Journal of natural products, Jun, Volume: 67, Issue:6
Biotransformation of imperatorin by Aspergillus flavus.
AID637775Inhibition of recombinant human BACE1 using Rh-EVNLDAEFK as substrate at 500 uM after 60 mins by fluorescence quenching assay2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor.
AID724355Inhibition of soybean LOX using sodium linoleate as substrate by spectrophotometric analysis2013European journal of medicinal chemistry, Feb, Volume: 60Syntheses and evaluation of the antioxidant activity of novel methoxypsoralen derivatives.
AID663619Antioxidant activity against AAPH-induced DNA oxidation assessed as decrease in thiobarbituric acid reactive substances at 80 to 200 uM measured every 120 mins by spectrophotometry2012European journal of medicinal chemistry, Jul, Volume: 53Synthesis of 4-methylcoumarin derivatives containing 4,5-dihydropyrazole moiety to scavenge radicals and to protect DNA.
AID487720Antioxidant activity assessed as protection against APPH-induced oxidation of DNA up to 675 mins2010European journal of medicinal chemistry, Jun, Volume: 45, Issue:6
Synthesis of methyl-substituted xanthotoxol to clarify prooxidant effect of methyl on radical-induced oxidation of DNA.
AID724354Antioxidant activity assessed as inhibition of AAPH-induced linoleic acid lipid peroxidation at 100 uM by spectrophotometric analysis2013European journal of medicinal chemistry, Feb, Volume: 60Syntheses and evaluation of the antioxidant activity of novel methoxypsoralen derivatives.
AID456256Inhibition of human recombinant BACE1 after 60 mins by fluorescence assay2010Bioorganic & medicinal chemistry, Jan-01, Volume: 18, Issue:1
Biotransformation of isoimperatorin and imperatorin by Glomerella cingulata and beta-secretase inhibitory activity.
AID487719Antioxidant activity assessed as protection against Cu(2+)/GST-induced DNA damage up to 180 mins by TBARS assay2010European journal of medicinal chemistry, Jun, Volume: 45, Issue:6
Synthesis of methyl-substituted xanthotoxol to clarify prooxidant effect of methyl on radical-induced oxidation of DNA.
AID487717Antioxidant activity assessed as DPPH radical scavenging activity measured up to 300 mins2010European journal of medicinal chemistry, Jun, Volume: 45, Issue:6
Synthesis of methyl-substituted xanthotoxol to clarify prooxidant effect of methyl on radical-induced oxidation of DNA.
AID724358Antioxidant activity assessed as DPPH radical scavenging activity at 100 uM after 20 mins by spectrophotometric analysis2013European journal of medicinal chemistry, Feb, Volume: 60Syntheses and evaluation of the antioxidant activity of novel methoxypsoralen derivatives.
AID540195Antibacterial activity against Helicobacter pylori SS1 assessed as inhibition of visible growth after 96 hrs by agar dilution method2010European journal of medicinal chemistry, Nov, Volume: 45, Issue:11
Structural modification of a specific antimicrobial lead against Helicobacter pylori discovered from traditional Chinese medicine and a structure-activity relationship study.
AID487715Antioxidant activity against beta-carotene and linoleic acid assessed as inhibition of bleaching of beta-carotene at 13.3 uM measured up to 540 mins by autooxidation assay2010European journal of medicinal chemistry, Jun, Volume: 45, Issue:6
Synthesis of methyl-substituted xanthotoxol to clarify prooxidant effect of methyl on radical-induced oxidation of DNA.
AID663621Antioxidant activity assessed as DPPH radical scavenging activity at 40 uM2012European journal of medicinal chemistry, Jul, Volume: 53Synthesis of 4-methylcoumarin derivatives containing 4,5-dihydropyrazole moiety to scavenge radicals and to protect DNA.
AID402908Antiviral activity against hepatitis B virus infected in human MS-G2 cells assessed as inhibition of e-antigen production at 10 uM after 48 hrs2004Journal of natural products, Jun, Volume: 67, Issue:6
Biotransformation of imperatorin by Aspergillus flavus.
AID663620Antioxidant activity assessed as ABTS radical scavenging activity at 40 uM2012European journal of medicinal chemistry, Jul, Volume: 53Synthesis of 4-methylcoumarin derivatives containing 4,5-dihydropyrazole moiety to scavenge radicals and to protect DNA.
AID487716Antioxidant activity assessed as ABTS radical scavenging activity measured up to 90 mins2010European journal of medicinal chemistry, Jun, Volume: 45, Issue:6
Synthesis of methyl-substituted xanthotoxol to clarify prooxidant effect of methyl on radical-induced oxidation of DNA.
AID402630Antiviral activity against hepatitis B virus infected in human MS-G2 cells assessed as inhibition of surface antigen production at 100 uM after 48 hrs2004Journal of natural products, Jun, Volume: 67, Issue:6
Biotransformation of imperatorin by Aspergillus flavus.
AID724357Antioxidant activity assessed as DPPH radical scavenging activity at 100 uM after 60 mins by spectrophotometric analysis2013European journal of medicinal chemistry, Feb, Volume: 60Syntheses and evaluation of the antioxidant activity of novel methoxypsoralen derivatives.
AID402906Antiviral activity against hepatitis B virus infected in human MS-G2 cells assessed as inhibition of e-antigen production at 100 uM after 48 hrs2004Journal of natural products, Jun, Volume: 67, Issue:6
Biotransformation of imperatorin by Aspergillus flavus.
AID402911Cytotoxicity against human MS-G2 cells at 10 uM by MTT assay2004Journal of natural products, Jun, Volume: 67, Issue:6
Biotransformation of imperatorin by Aspergillus flavus.
AID637774Inhibition of recombinant human BACE1 using Rh-EVNLDAEFK as substrate after 60 mins by fluorescence quenching assay2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor.
AID402631Antiviral activity against hepatitis B virus infected in human MS-G2 cells assessed as inhibition of surface antigen production at 50 uM after 48 hrs2004Journal of natural products, Jun, Volume: 67, Issue:6
Biotransformation of imperatorin by Aspergillus flavus.
AID487721Antioxidant activity assessed as protection against APPH-induced oxidation of DNA at 0.2 mM up to 675 mins2010European journal of medicinal chemistry, Jun, Volume: 45, Issue:6
Synthesis of methyl-substituted xanthotoxol to clarify prooxidant effect of methyl on radical-induced oxidation of DNA.
AID402907Antiviral activity against hepatitis B virus infected in human MS-G2 cells assessed as inhibition of e-antigen production at 50 uM after 48 hrs2004Journal of natural products, Jun, Volume: 67, Issue:6
Biotransformation of imperatorin by Aspergillus flavus.
AID411503Anticancer activity against human HT-29 cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry, Jan-01, Volume: 17, Issue:1
Identification and physiological evaluation of the components from citrus fruits as potential drugs for anti-corpulence and anticancer.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (37)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (13.51)18.2507
2000's7 (18.92)29.6817
2010's18 (48.65)24.3611
2020's7 (18.92)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.82

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 Index25.82 (24.57)
Research Supply Index3.69 (2.92)
Research Growth Index4.84 (4.65)
Search Engine Demand Index29.35 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.82)

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%
Other39 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]