Page last updated: 2024-12-08
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]
Related Flora
| Flora | Rank | Flora Definition | Family | Family Definition |
|---|---|---|---|---|
| Angelica | genus | A plant genus of the family Apiaceae.[MeSH] | Apiaceae | A 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 gigas | species | [no description available] | Apiaceae | A 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 Source | ID |
|---|---|
| PubMed CID | 442127 |
| CHEMBL ID | 481657 |
| CHEBI ID | 4354 |
| SCHEMBL ID | 14105325 |
| MeSH ID | M0449964 |
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)
| Role | Description |
|---|---|
| metabolite | Any 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) inhibitor | An 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 agent | A substance that inhibits or prevents the proliferation of neoplasms. |
| analgesic | An 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)
| Class | Description |
|---|---|
| organic heterotricyclic compound | An organic tricyclic compound in which at least one of the rings of the tricyclic skeleton contains one or more heteroatoms. |
| delta-lactone | A lactone having a six-membered lactone ring. |
| secondary alcohol | A 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 ether | Any 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
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| thioredoxin reductase | Rattus norvegicus (Norway rat) | Potency | 56.2341 | 0.1000 | 20.8793 | 79.4328 | AID588456 |
| ATAD5 protein, partial | Homo sapiens (human) | Potency | 16.3535 | 0.0041 | 10.8903 | 31.5287 | AID504467 |
| Smad3 | Homo sapiens (human) | Potency | 5.6234 | 0.0052 | 7.8098 | 29.0929 | AID588855 |
| [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) |
|---|---|---|---|---|---|---|---|
| Acetylcholinesterase | Homo sapiens (human) | IC50 (µMol) | 28.0000 | 0.0000 | 0.9332 | 10.0000 | AID360659 |
| Beta-secretase 1 | Homo sapiens (human) | IC50 (µMol) | 500.0000 | 0.0006 | 1.6194 | 10.0000 | AID637774 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
Biological Processes (30)
Molecular Functions (16)
Ceullar Components (29)
Bioassays (24)
| 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. |
| 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. |
| 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. |
| AID1745845 | Primary qHTS for Inhibitors of ATXN expression | |||
| 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. |
| AID1347082 | qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal | 2020 | Antiviral research, 01, Volume: 173 | A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity. |
| AID1347086 | qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal | 2020 | Antiviral research, 01, Volume: 173 | A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity. |
| AID1347083 | qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen | 2020 | Antiviral research, 01, Volume: 173 | A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity. |
| AID651635 | Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression | |||
| AID548093 | Cytotoxicity against mouse B16F10 cells assessed as cell viability after 24 hrs by MTT assay | 2010 | European 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. |
| AID548092 | Inhibition of melanin production in mouse B16F10 cells at 100 uM after 2 days | 2010 | European 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. |
| AID376761 | Neuroprotective effect against glutamate-stimulated rat cortical cells assessed as cell viability at 10 uM after 1 hr by LDH assay relative to control | 2005 | Journal of natural products, Jan, Volume: 68, Issue:1 | Four new neuroprotective dihydropyranocoumarins from Angelica gigas. |
| AID637774 | Inhibition of recombinant human BACE1 using Rh-EVNLDAEFK as substrate after 60 mins by fluorescence quenching assay | 2012 | Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2 | Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor. |
| AID360659 | Inhibition of AChE by spectrophotometry | 2001 | Journal of natural products, May, Volume: 64, Issue:5 | Coumarins isolated from Angelica gigas inhibit acetylcholinesterase: structure-activity relationships. |
| AID637775 | Inhibition of recombinant human BACE1 using Rh-EVNLDAEFK as substrate at 500 uM after 60 mins by fluorescence quenching assay | 2012 | Bioorganic & medicinal chemistry, Jan-15, Volume: 20, Issue:2 | Structure-activity relationships for naturally occurring coumarins as β-secretase inhibitor. |
| AID376759 | Neuroprotective effect against glutamate-stimulated rat cortical cells assessed as cell viability at 0.1 uM after 1 hr by LDH assay relative to control | 2005 | Journal of natural products, Jan, Volume: 68, Issue:1 | Four new neuroprotective dihydropyranocoumarins from Angelica gigas. |
| AID376760 | Neuroprotective effect against glutamate-stimulated rat cortical cells assessed as cell viability at 1 uM after 1 hr by LDH assay relative to control | 2005 | Journal 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)
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 3 (30.00) | 29.6817 |
| 2010's | 5 (50.00) | 24.3611 |
| 2020's | 2 (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.
| This Compound (27.70) 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 | 10 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||