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=C(O)C=C2OC(=O)C=CC2=C1
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) |
|||
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 |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| A new cytotoxic daphnane diterpenoid, rediocide G, from Trigonostemon reidioides. | 2005-10 |
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| HPLC-SPE-NMR hyphenation in natural products research: optimization of analysis of Croton membranaceus extract. | 2005-09 |
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| Scopoletin induces apoptosis in human promyeloleukemic cells, accompanied by activations of nuclear factor kappaB and caspase-3. | 2005-07-01 |
|
| A labdane diterpene glucoside from the rhizomes of Curcuma mangga. | 2005-07 |
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| Kinetic characterization of the 1A subfamily of recombinant human UDP-glucuronosyltransferases. | 2005-07 |
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| Metabolite fingerprinting in transgenic Nicotiana tabacum altered by the Escherichia coli glutamate dehydrogenase gene. | 2005-06-30 |
|
| [Effect of caffeic acid, seopoletin and scutellarin on rat retinal neurons in vitro]. | 2005-06 |
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| Purification and characterization of a cationic peroxidase Cs in Raphanus sativus. | 2005-06 |
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| Inhibitory effect of coumarins from Weigela subsessilis on low density lipoprotein oxidation. | 2005-06 |
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| Anthraquinones from Hedyotis capitellata. | 2005-05 |
|
| Antifungal synergistic effect of scopoletin, a hydroxycoumarin isolated from Melia azedarach L. fruits. | 2005-04-20 |
|
| Combination of extractive solvent addition and immobilization culture for continuous production of scopoletin by tobacco cells. | 2005-04-02 |
|
| Morning glory systemically accumulates scopoletin and scopolin after interaction with Fusarium oxysporum. | 2005-03-25 |
|
| Simultaneous determination of active ingredients in Erigeron breviscapus (Vant.) Hand-Mazz. by capillary electrophoresis with electrochemical detection. | 2005-03-09 |
|
| Acylperoxylated and seco-mexicanolides from stems of Khaya anthotheca. | 2005-03 |
|
| Cytotoxic constituents of the twigs of Simarouba glauca collected from a plot in Southern Florida. | 2005-02 |
|
| Hypouricemic action of scopoletin arising from xanthine oxidase inhibition and uricosuric activity. | 2005-02 |
|
| Total synthesis and biological activity of 13,14-dehydro-12-oxo-phytodienoic acids (deoxy-J1-phytoprostanes). | 2005-02 |
|
| A new antipsychotic effective neolignan from Firmiana simplex. | 2005-01 |
|
| [Determination of scopoletin and umbelliferone contents in Saussurea medusa Maxim by high-performance liquid chromatography]. | 2005-01 |
|
| B1-phytoprostanes trigger plant defense and detoxification responses. | 2005-01 |
|
| Comparison of cytotoxicity of cysteine and homocysteine for renal epithelial cells. | 2005 |
|
| The interactions between the N-terminal and C-terminal domains of the human UDP-glucuronosyltransferases are partly isoform-specific, and may involve both monomers. | 2004-12-15 |
|
| Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products. | 2004-12-02 |
|
| Characterization of cigarette tobacco by direct electrospray ionization-ion trap mass spectrometry (ESI-ITMS) analysis of the aqueous extract--a novel and simple approach. | 2004-12-01 |
|
| Oxidative stress responses during cassava post-harvest physiological deterioration. | 2004-11 |
|
| Antiinflammatory activity of Synurus deltoides. | 2004-11 |
|
| Beta-1,3 glucan sulfate, but not beta-1,3 glucan, induces the salicylic acid signaling pathway in tobacco and Arabidopsis. | 2004-11 |
|
| A new sesquiterpene lactone from Artemisia rubripes nakai. | 2004-10 |
|
| Oxidative DNA damage induced by a hydroperoxide derivative of cyclophosphamide. | 2004-09-15 |
|
| Nor-ent-kaurane diterpenes and hydroxylactones from Antennaria geyeri and Anaphalis margaritacea. | 2004-09 |
|
| Umbelliferone released from hairy root cultures of Pharbitis nil treated with copper sulfate and its subsequent glucosylation. | 2004-09 |
|
| A coumarin from Mallotus resinosus that mediates DNA cleavage. | 2004-09 |
|
| Cytotoxic constituents of roots of Chaerophyllum hirsutum. | 2004-09 |
|
| Phenylpropanoids, phenylalanine ammonia lyase and peroxidases in elicitor-challenged cassava (Manihot esculenta) suspension cells and leaves. | 2004-07 |
|
| Constituents of Carapa guianensis Aubl. (Meliaceae). | 2004-06 |
|
| Scopoletin suppresses pro-inflammatory cytokines and PGE2 from LPS-stimulated cell line, RAW 264.7 cells. | 2004-06 |
|
| [Study on constituents from Neonauclea griffithii]. | 2004-05 |
|
| Generation of hydrogen peroxide and failure of antioxidative responses in pancreatic islets of male C57BL/6 mice are associated with diabetes induced by multiple low doses of streptozotocin. | 2004-04 |
|
| An active and water-soluble truncation mutant of the human UDP-glucuronosyltransferase 1A9. | 2004-04 |
|
| Secondary metabolite content in Fabiana imbricata plants and in vitro cultures. | 2004-03-17 |
|
| Anthrone and oxanthrone C-glycosides from Picramnia latifolia collected in Peru. | 2004-03 |
|
| Potential cancer chemopreventive constituents of the leaves of Macaranga triloba. | 2004-02 |
|
| Over-expression of a scopoletin glucosyltransferase in Nicotiana tabacum leads to precocious lesion formation during the hypersensitive response to tobacco mosaic virus but does not affect virus resistance. | 2004-01 |
|
| Acetylcholinesterase inhibitors from the twigs of Vaccinium oldhami Miquel. | 2004-01 |
|
| Active components from Artemisia iwayomogi displaying ONOO(-) scavenging activity. | 2004-01 |
|
| Agrobacterium tumefaciens AK-6b gene modulates phenolic compound metabolism in tobacco. | 2004-01 |
|
| Influence of distillation system, oak wood type, and aging time on composition of cider brandy in phenolic and furanic compounds. | 2003-12-31 |
|
| Fc epsilon RI signaling of mast cells activates intracellular production of hydrogen peroxide: role in the regulation of calcium signals. | 2003-12-01 |
|
| [Studies on chemical constitutes of Phellinus igniarius]. | 2003-04 |
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
by
admin
on
Edited
Mon Mar 31 19:43:02 GMT 2025
by
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on
Mon Mar 31 19:43:02 GMT 2025
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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 | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
