Page last updated: 2024-11-08

decursinol

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

Description

decursinol : An organic heterotricyclic compound that is 7,8-dihydro-2H,6H-pyrano[3,2-g]chromen-2-one substituted by a beta-hydroxy group at position 7 and two methyl groups at position 8. It is isolated from the roots of Angelica gigas and has been found to possess significant inhibitory activity against acetylcholinesterase enzyme (EC 3.1.1.7). [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]

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 gigasspecies[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 CID442127
CHEMBL ID481657
CHEBI ID4354
SCHEMBL ID14105325
MeSH IDM0449964

Synonyms (39)

Synonym
AKOS008901445
C09259
decursinol
23458-02-8
smr001397017
MLS002472906
(3s)-3-hydroxy-2,2-dimethyl-3,4-dihydropyrano[3,2-g]chromen-8-one
bdbm50259817
chebi:4354 ,
CHEMBL481657 ,
(+)-decursinol
2h,6h-benzo(1,2-b:5,4-b')dipyran-2-one, 7,8-dihydro-7-hydroxy-8,8-dimethyl-, (s)-
HMS2192M06
decursinol [inci]
smyrinol
2h,6h-benzo(1,2-b:5,4-b')dipyran-2-one, 7,8-dihydro-7-hydroxy-8,8-dimethyl-, (s)-(+)-
smirino
sfe decursinol
ubi4yb704b ,
unii-ubi4yb704b
(7s)-7-hydroxy-8,8-dimethyl-7,8-dihydro-2h,6h-pyrano[3,2-g]chromen-2-one
(s)-(+)-decursinol
7-hydroxy-8,8-dimethyl-7,8-dihydro-2h,6h-pyrano[3,2-g]chromen-2-one #
BGXFQDFSVDZUIW-LBPRGKRZSA-N
(s)-7-hydroxy-8,8-dimethyl-7,8-dihydropyrano(3,2-g)chromen-2(6h)-one
SCHEMBL14105325
(7s)-7,8-dihydro-7-hydroxy-8,8-dimethyl-2h,6h-benzo[1,2-b:5,4-b']dipyran-2-one
DTXSID70178008
mfcd06636641
BCP24688
HY-N4109
Q27068163
CS-0032117
D85508
(s)-7-hydroxy-8,8-dimethyl-7,8-dihydro-2h,6h-pyrano[3,2-g]chromen-2-one
WS-01956
(s)-7-hydroxy-8,8-dimethyl-7,8-dihydropyrano[3,2-g]chromen-2(6h)-one
(7s)-7-hydroxy-8,8-dimethyl-2h,6h,7h,8h-pyrano[3,2-g]chromen-2-one
2h,6h-benzo[1,2-b:5,4-b']dipyran-2-one, 7,8-dihydro-7-hydroxy-8,8-dimethyl-, (7s)-
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (4)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
EC 3.1.1.7 (acetylcholinesterase) inhibitorAn EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of enzyme acetylcholinesterase (EC 3.1.1.7), which helps breaking down of acetylcholine into choline and acetic acid.
antineoplastic agentA substance that inhibits or prevents the proliferation of neoplasms.
analgesicAn agent capable of relieving pain without the loss of consciousness or without producing anaesthesia. In addition, analgesic is a role played by a compound which is exhibited by a capability to cause a reduction of pain symptoms.
[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 (4)

ClassDescription
organic heterotricyclic compoundAn organic tricyclic compound in which at least one of the rings of the tricyclic skeleton contains one or more heteroatoms.
delta-lactoneA lactone having a six-membered lactone ring.
secondary alcoholA secondary alcohol is a compound in which a hydroxy group, -OH, is attached to a saturated carbon atom which has two other carbon atoms attached to it.
cyclic etherAny ether in which the oxygen atom forms part of a ring.
[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 (5)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
thioredoxin reductaseRattus norvegicus (Norway rat)Potency56.23410.100020.879379.4328AID588456
ATAD5 protein, partialHomo sapiens (human)Potency16.35350.004110.890331.5287AID504467
Smad3Homo sapiens (human)Potency5.62340.00527.809829.0929AID588855
[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)
AcetylcholinesteraseHomo sapiens (human)IC50 (µMol)28.00000.00000.933210.0000AID360659
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 (30)

Processvia Protein(s)Taxonomy
acetylcholine catabolic process in synaptic cleftAcetylcholinesteraseHomo sapiens (human)
regulation of receptor recyclingAcetylcholinesteraseHomo sapiens (human)
osteoblast developmentAcetylcholinesteraseHomo sapiens (human)
acetylcholine catabolic processAcetylcholinesteraseHomo sapiens (human)
cell adhesionAcetylcholinesteraseHomo sapiens (human)
nervous system developmentAcetylcholinesteraseHomo sapiens (human)
synapse assemblyAcetylcholinesteraseHomo sapiens (human)
receptor internalizationAcetylcholinesteraseHomo sapiens (human)
negative regulation of synaptic transmission, cholinergicAcetylcholinesteraseHomo sapiens (human)
amyloid precursor protein metabolic processAcetylcholinesteraseHomo sapiens (human)
positive regulation of protein secretionAcetylcholinesteraseHomo sapiens (human)
retina development in camera-type eyeAcetylcholinesteraseHomo sapiens (human)
acetylcholine receptor signaling pathwayAcetylcholinesteraseHomo sapiens (human)
positive regulation of cold-induced thermogenesisAcetylcholinesteraseHomo 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 (16)

Processvia Protein(s)Taxonomy
amyloid-beta bindingAcetylcholinesteraseHomo sapiens (human)
acetylcholinesterase activityAcetylcholinesteraseHomo sapiens (human)
cholinesterase activityAcetylcholinesteraseHomo sapiens (human)
protein bindingAcetylcholinesteraseHomo sapiens (human)
collagen bindingAcetylcholinesteraseHomo sapiens (human)
hydrolase activityAcetylcholinesteraseHomo sapiens (human)
serine hydrolase activityAcetylcholinesteraseHomo sapiens (human)
acetylcholine bindingAcetylcholinesteraseHomo sapiens (human)
protein homodimerization activityAcetylcholinesteraseHomo sapiens (human)
laminin bindingAcetylcholinesteraseHomo 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 (29)

Processvia Protein(s)Taxonomy
extracellular regionAcetylcholinesteraseHomo sapiens (human)
basement membraneAcetylcholinesteraseHomo sapiens (human)
extracellular spaceAcetylcholinesteraseHomo sapiens (human)
nucleusAcetylcholinesteraseHomo sapiens (human)
Golgi apparatusAcetylcholinesteraseHomo sapiens (human)
plasma membraneAcetylcholinesteraseHomo sapiens (human)
cell surfaceAcetylcholinesteraseHomo sapiens (human)
membraneAcetylcholinesteraseHomo sapiens (human)
neuromuscular junctionAcetylcholinesteraseHomo sapiens (human)
synaptic cleftAcetylcholinesteraseHomo sapiens (human)
synapseAcetylcholinesteraseHomo sapiens (human)
perinuclear region of cytoplasmAcetylcholinesteraseHomo sapiens (human)
side of membraneAcetylcholinesteraseHomo 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 (24)

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.
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
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.
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.
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
AID548093Cytotoxicity against mouse B16F10 cells assessed as cell viability after 24 hrs by MTT assay2010European journal of medicinal chemistry, Dec, Volume: 45, Issue:12
Synthesis of (S)-(+)-decursin and its analogues as potent inhibitors of melanin formation in B16 murine melanoma cells.
AID548092Inhibition of melanin production in mouse B16F10 cells at 100 uM after 2 days2010European journal of medicinal chemistry, Dec, Volume: 45, Issue:12
Synthesis of (S)-(+)-decursin and its analogues as potent inhibitors of melanin formation in B16 murine melanoma cells.
AID376761Neuroprotective effect against glutamate-stimulated rat cortical cells assessed as cell viability at 10 uM after 1 hr by LDH assay relative to control2005Journal of natural products, Jan, Volume: 68, Issue:1
Four new neuroprotective dihydropyranocoumarins from Angelica gigas.
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.
AID360659Inhibition of AChE by spectrophotometry2001Journal of natural products, May, Volume: 64, Issue:5
Coumarins isolated from Angelica gigas inhibit acetylcholinesterase: structure-activity relationships.
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.
AID376759Neuroprotective effect against glutamate-stimulated rat cortical cells assessed as cell viability at 0.1 uM after 1 hr by LDH assay relative to control2005Journal of natural products, Jan, Volume: 68, Issue:1
Four new neuroprotective dihydropyranocoumarins from Angelica gigas.
AID376760Neuroprotective effect against glutamate-stimulated rat cortical cells assessed as cell viability at 1 uM after 1 hr by LDH assay relative to control2005Journal of natural products, Jan, Volume: 68, Issue:1
Four new neuroprotective dihydropyranocoumarins from Angelica gigas.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's3 (30.00)29.6817
2010's5 (50.00)24.3611
2020's2 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 27.70

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 Index27.70 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.31 (4.65)
Search Engine Demand Index31.58 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (27.70)

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%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]