Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C10H8O4 |
| Molecular Weight | 192.1681 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC2=C(OC(=O)C=C2)C=C1O
InChI
InChIKey=RODXRVNMMDRFIK-UHFFFAOYSA-N
InChI=1S/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3
| Molecular Formula | C10H8O4 |
| Molecular Weight | 192.1681 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Scopoletin is a coumarin that can be isolated from plants of the genus Scopolia. It has been identified as a natural antifungal compound. Scopoletin was also demonstrated to be an MAO inhibitor capable of increasing dopamine levels in mice and is therefore of potential interest for developing treatments for neurodegenerative diseases.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: P04637|||Q16810|||Q3LRW5|||Q9NZD0 Gene ID: 7157.0 Gene Symbol: TP53 Target Organism: Homo sapiens (Human) |
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Target ID: P27338 Gene ID: 4129.0 Gene Symbol: MAOB Target Organism: Homo sapiens (Human) |
20.7 µM [Ki] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| New indole alkaloids from Sarcocephalus latifolius. | 2001 |
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| Quassinoids from Eurycoma harmandiana. | 2001 Aug |
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| Terpenoids from Guarea rhophalocarpa. | 2001 Jan |
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| Mode of action of hot-water dip in reducing decay of lemon fruit. | 2001 Jan |
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| Gliotoxin induces apoptosis in cultured macrophages via production of reactive oxygen species and cytochrome c release without mitochondrial depolarization. | 2001 Jul |
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| Cr (VI) induces cell growth arrest through hydrogen peroxide-mediated reactions. | 2001 Jun |
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| Characterization of 2-[[4-[[2-(1H-tetrazol-5-ylmethyl)phenyl]methoxy]methyl]quinoline N-glucuronidation by in vitro and in vivo approaches. | 2001 Mar |
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| Effect of scopoletin on PC3 cell proliferation and apoptosis. | 2001 Oct |
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| Coumarins with monoamine oxidase inhibitory activity and antioxidative coumarino-lignans from Hibiscus syriacus. | 2001 Sep |
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| Cytotoxic and novel compounds from Solanum indicum. | 2001 Sep |
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| Inhibitory effects of phenylpropanoid metabolites on copper-induced protein oxidative modification of mice brain homogenate, in vitro. | 2002 Feb |
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| A pharmacophore for human pregnane X receptor ligands. | 2002 Jan |
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| [Studies on immunocompetent constituents of Patrinia scabra Bunge]. | 2002 Mar |
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| High-performance liquid chromatography determination of methionine adenosyltransferase activity using catechol-O-methyltransferase-coupled fluorometric detection. | 2003 Aug 1 |
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| Sulfated fucan oligosaccharides elicit defense responses in tobacco and local and systemic resistance against tobacco mosaic virus. | 2003 Feb |
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| Study on the determination of polyphenols in tobacco by HPLC coupled with ESI-MS after solid-phase extraction. | 2003 Jan |
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| New anthracene derivatives from Coussarea macrophylla. | 2003 Jul |
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| Cyclopentenone isoprostanes induced by reactive oxygen species trigger defense gene activation and phytoalexin accumulation in plants. | 2003 May |
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| DNA damage by ethylbenzenehydroperoxide formed from carcinogenic ethylbenzene by sunlight irradiation. | 2003 May 16 |
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| Antioxidant activity of compounds from the medicinal herb Aster tataricus. | 2003 Oct |
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| An active and water-soluble truncation mutant of the human UDP-glucuronosyltransferase 1A9. | 2004 Apr |
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| Active components from Artemisia iwayomogi displaying ONOO(-) scavenging activity. | 2004 Jan |
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| Secondary metabolite content in Fabiana imbricata plants and in vitro cultures. | 2004 Jan-Feb |
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| Scopoletin suppresses pro-inflammatory cytokines and PGE2 from LPS-stimulated cell line, RAW 264.7 cells. | 2004 Jun |
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| Oxidative stress responses during cassava post-harvest physiological deterioration. | 2004 Nov |
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| Antiinflammatory activity of Synurus deltoides. | 2004 Nov |
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| A new sesquiterpene lactone from Artemisia rubripes nakai. | 2004 Oct |
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| Oxidative DNA damage induced by a hydroperoxide derivative of cyclophosphamide. | 2004 Sep 15 |
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| B1-phytoprostanes trigger plant defense and detoxification responses. | 2005 Jan |
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| Morning glory systemically accumulates scopoletin and scopolin after interaction with Fusarium oxysporum. | 2005 Jan-Feb |
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| A labdane diterpene glucoside from the rhizomes of Curcuma mangga. | 2005 Jul |
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| Kinetic characterization of the 1A subfamily of recombinant human UDP-glucuronosyltransferases. | 2005 Jul |
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| Combination of extractive solvent addition and immobilization culture for continuous production of scopoletin by tobacco cells. | 2005 Mar-Apr |
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| HPLC-SPE-NMR hyphenation in natural products research: optimization of analysis of Croton membranaceus extract. | 2005 Sep |
Sample Use Guides
Scopoletin encapsulated in Soluplus micelles was administered to rats at an oral dose equivalent to 100 mg/kg of free scopoletin. Formulation with Soluplus micelles dramatically enhanced the oral bioavailability.
Route of Administration:
Oral
Four-day-old spores from F. verticilliodes were added to sterile glucose mineral salts medium to reach 10^ 5 spores/mL. Scopoletin dissolved in sterile dimethyl sulfoxide was incorporated into each well containing the spore suspension, resulting in concentrations ranging from 0.10 to 1.70 mg/mL. The percentage of fungi growth recorded as spore germination with respect to control was visually assessed with an inverted light microscope for each concentration of the compound. The MIC of scopoletin against F. Verticillioides was 1.50 mg/mL, with its IC50 equivalent to 0.73 mg/mL.
| Substance Class |
Chemical
Created
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admin
on
Edited
Fri Dec 15 19:19:05 GMT 2023
by
admin
on
Fri Dec 15 19:19:05 GMT 2023
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| Record UNII |
KLF1HS0SXJ
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C45597
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17488
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DTXSID0075368
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405647
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m9815
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SCOPOLETIN
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92-61-5
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KLF1HS0SXJ
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D012603
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C126100
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202-171-9
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1610090
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PARENT -> CONSTITUENT ALWAYS PRESENT |
