Page last updated: 2024-11-05

9-(2,3-dihydroxy-3-methylbutoxy)-4-methoxy-7h-furo(3,2-g)(1)benzopyran-7-one

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

Description

9-(2,3-dihydroxy-3-methylbutoxy)-4-methoxy-7H-furo(3,2-g)(1)benzopyran-7-one: isolated from Angelica dahurica (Umbelliferae); structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
AngelicagenusA plant genus of the family Apiaceae.[MeSH]ApiaceaeA large plant family in the order Apiales, also known as Umbelliferae. Most are aromatic herbs with alternate, feather-divided leaves that are sheathed at the base. The flowers often form a conspicuous flat-topped umbel. Each small individual flower is usually bisexual, with five sepals, five petals, and an enlarged disk at the base of the style. The fruits are ridged and are composed of two parts that split open at maturity.[MeSH]
Angelica dahuricaspecies[no description available]ApiaceaeA large plant family in the order Apiales, also known as Umbelliferae. Most are aromatic herbs with alternate, feather-divided leaves that are sheathed at the base. The flowers often form a conspicuous flat-topped umbel. Each small individual flower is usually bisexual, with five sepals, five petals, and an enlarged disk at the base of the style. The fruits are ridged and are composed of two parts that split open at maturity.[MeSH]

Cross-References

ID SourceID
PubMed CID10211
CHEMBL ID508648
CHEBI ID3250
MeSH IDM0398307

Synonyms (44)

Synonym
biacangelicin
byak-angelicin
9-(2,3-dihydroxy-3-methylbutoxy)-4-methoxy-7h-furo(3,2-g)(1)benzopyran-7-one
7h-furo(3,2-g)(1)benzopyran-7-one, 9-(2,3-dihydroxy-3-methylbutoxy)-4-methoxy-, (r)-
byankagelicine
bjacangelicin
bjakangelicin
(r)-9-(2,3-dihydroxy-3-methylbutoxy)-4-methoxy-7h-furo(3,2-g)(1)benzopyran-7-one
smr000156212
MLS000574875
482-25-7
byakangelicin
C09141
9-[(2r)-2,3-dihydroxy-3-methylbutoxy]-4-methoxyfuro[3,2-g]chromen-7-one
CHEMBL508648
byakangelicine
chebi:3250 ,
NCGC00247536-01
HMS2194N09
FT-0689305
bdbm50361390
unii-le80z850i1
le80z850i1 ,
7h-furo[3,2-g][1]benzopyran-7-one,9-[(2r)-2,3-dihydroxy-3-methylbutoxy]-4-methoxy-
PKRPFNXROFUNDE-LLVKDONJSA-N
byacangelicin
AC-33998
Q-100528
(+)-byakangelicin
9-[(2r)-2,3-dihydroxy-3-methyl-butoxy]-4-methoxy-furo[3,2-g]chromen-7-one
9-((2r)-2,3-dihydroxy-3-methylbutoxy)-4-methoxy-7h-furo(3,2-g)(1)benzopyran-7-one
7h-furo(3,2-g)(1)benzopyran-7-one, 9-((2r)-2,3-dihydroxy-3-methylbutoxy)-4-methoxy-
5-methoxy-8-(2,3-dihydroxy-3-methylbutoxy)psoralene
26091-78-1
byakangelicin, (+)-
biacangelicin, analytical standard
DTXSID70197456
(r)-9-(2,3-dihydroxy-3-methylbutoxy)-4-methoxy-7h-furo[3,2-g]chromen-7-one
AKOS032949081
Q3639306
BS-17100
A14670
CS-0032189
HY-N6022

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
"A high-performance liquid chromatographic method was developed and validated for the determination and pharmacokinetic study of oxypeucedanin hydrate and byak-angelicin after oral administration of Angelica dahurica extracts in mongrel dog plasma."( High-performance liquid chromatographic method for the determination and pharmacokinetic study of oxypeucedanin hydrate and byak-angelicin after oral administration of Angelica dahurica extracts in mongrel dog plasma.
Chen, Y; Fan, G; Lin, M; Wen, J; Wu, Y; Xie, Y, 2007
)
0.34
" 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
)
0.56
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
psoralensA furanocoumarin with a 7H-furo[3,2-g]chromen-7-one skeleton and its substituted derivatives thereof.
[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 (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency0.56230.044717.8581100.0000AID485294
Chain A, 2-oxoglutarate OxygenaseHomo sapiens (human)Potency39.81070.177814.390939.8107AID2147
USP1 protein, partialHomo sapiens (human)Potency11.22020.031637.5844354.8130AID743255
IDH1Homo sapiens (human)Potency18.35640.005210.865235.4813AID686970
chromobox protein homolog 1Homo sapiens (human)Potency89.12510.006026.168889.1251AID540317
muscleblind-like protein 1 isoform 1Homo sapiens (human)Potency17.78280.00419.962528.1838AID2675
Rap guanine nucleotide exchange factor 3Homo sapiens (human)Potency125.89206.309660.2008112.2020AID720707
[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)219.70000.00061.619410.0000AID637774
Beta-secretase 1Homo sapiens (human)Ki30.60000.00031.35248.0000AID637776; AID637827
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (36)

Processvia Protein(s)Taxonomy
angiogenesisRap guanine nucleotide exchange factor 3Homo sapiens (human)
adaptive immune responseRap guanine nucleotide exchange factor 3Homo sapiens (human)
signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
adenylate cyclase-activating G protein-coupled receptor signaling pathwayRap guanine nucleotide exchange factor 3Homo sapiens (human)
associative learningRap guanine nucleotide exchange factor 3Homo sapiens (human)
Rap protein signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
regulation of actin cytoskeleton organizationRap guanine nucleotide exchange factor 3Homo sapiens (human)
negative regulation of syncytium formation by plasma membrane fusionRap guanine nucleotide exchange factor 3Homo sapiens (human)
intracellular signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of GTPase activityRap guanine nucleotide exchange factor 3Homo sapiens (human)
regulation of angiogenesisRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of angiogenesisRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of protein export from nucleusRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of stress fiber assemblyRap guanine nucleotide exchange factor 3Homo sapiens (human)
regulation of phosphatidylinositol 3-kinase/protein kinase B signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
positive regulation of syncytium formation by plasma membrane fusionRap guanine nucleotide exchange factor 3Homo sapiens (human)
establishment of endothelial barrierRap guanine nucleotide exchange factor 3Homo sapiens (human)
cellular response to cAMPRap guanine nucleotide exchange factor 3Homo sapiens (human)
Ras protein signal transductionRap guanine nucleotide exchange factor 3Homo sapiens (human)
regulation of insulin secretionRap guanine nucleotide exchange factor 3Homo sapiens (human)
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 (11)

Processvia Protein(s)Taxonomy
guanyl-nucleotide exchange factor activityRap guanine nucleotide exchange factor 3Homo sapiens (human)
protein bindingRap guanine nucleotide exchange factor 3Homo sapiens (human)
protein domain specific bindingRap guanine nucleotide exchange factor 3Homo sapiens (human)
cAMP bindingRap guanine nucleotide exchange factor 3Homo sapiens (human)
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 (26)

Processvia Protein(s)Taxonomy
plasma membraneRap guanine nucleotide exchange factor 3Homo sapiens (human)
cortical actin cytoskeletonRap guanine nucleotide exchange factor 3Homo sapiens (human)
plasma membraneRap guanine nucleotide exchange factor 3Homo sapiens (human)
microvillusRap guanine nucleotide exchange factor 3Homo sapiens (human)
endomembrane systemRap guanine nucleotide exchange factor 3Homo sapiens (human)
membraneRap guanine nucleotide exchange factor 3Homo sapiens (human)
lamellipodiumRap guanine nucleotide exchange factor 3Homo sapiens (human)
filopodiumRap guanine nucleotide exchange factor 3Homo sapiens (human)
extracellular exosomeRap guanine nucleotide exchange factor 3Homo sapiens (human)
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 (25)

Assay IDTitleYearJournalArticle
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.
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.
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.
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.
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.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
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.
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.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID637776Inhibition of recombinant human BACE1 assessed as dissociation constant of enzyme-inhibitor complex using Rh-EVNLDAEFK as substrate by Dixon and Cornish-Bowden plots analysis2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor.
AID401513Effect on compound 48/80-induced histamine level in ddY mouse peritoneal cavity fluid assessed as histamine release at 10 mg/kg, ip administered 15 mins before compound 48/80 challenge measured after 10 mins by fluorometric assay relative to control1997Journal of natural products, Mar, Volume: 60, Issue:3
Histamine-release effectors from Angelica dahurica var. dahurica root.
AID1615748Inhibition of H2O2-induced ROS accumulation in human HepG2 cells assessed as ROS generation at 10 uM preincubated for 1 hr followed by H2O2-stimulation and measured after 30 mins by H2DCFDA staining based flow cytometry (Rvb = 100 +/- 11.53%)2019Journal of natural products, 09-27, Volume: 82, Issue:9
Furanocoumarins from the Roots of
AID637777Mixed type inhibition of recombinant human BACE1 using Rh-EVNLDAEFK as substrate by Dixon and Cornish-Bowden plots analysis2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor.
AID401514Effect on compound 48/80-induced histamine level in ddY mouse peritoneal cavity fluid assessed as histamine release at 25 mg/kg, ip administered 15 mins before compound 48/80 challenge measured after 10 mins by fluorometric assay relative to control1997Journal of natural products, Mar, Volume: 60, Issue:3
Histamine-release effectors from Angelica dahurica var. dahurica root.
AID1615747Hepatoprotective activity against H2O2-induced cell death in human HepG2 cells assessed as cell viability at 10 uM preincubated for 1 hr followed by H2O2-stimulation and measured after 24 hrs by EZ-Cytox cell viability assay (Rvb = 43.9 +/- 5.25%)2019Journal of natural products, 09-27, Volume: 82, Issue:9
Furanocoumarins from the Roots of
AID1615746Cytotoxicity against human HepG2 cells assessed as cell viability at 10 uM incubated for 1 hr by EZ-Cytox cell viability assay2019Journal of natural products, 09-27, Volume: 82, Issue:9
Furanocoumarins from the Roots of
AID637827Inhibition of recombinant human BACE1 assessed as dissociation constant of enzyme-substrate-inhibitor complex using Rh-EVNLDAEFK as substrate by Dixon and Cornish-Bowden plots analysis2012Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2
Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor.
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.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (22)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (4.55)18.2507
2000's6 (27.27)29.6817
2010's10 (45.45)24.3611
2020's5 (22.73)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.25

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 Index12.25 (24.57)
Research Supply Index3.14 (2.92)
Research Growth Index5.39 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.25)

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%
Other22 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]