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) |
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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 |
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| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Studies on chemical constitutes of Phellinus igniarius]. | 2003 Apr |
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| Three new jatrophane-type diterpenes from Euphorbia pubescens. | 2003 Apr |
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| Compounds obtained from sida acuta with the potential to induce quinone reductase and to inhibit 7,12-dimethylbenz[a]anthracene-induced preneoplastic lesions in a mouse mammary organ culture model. | 2003 Aug |
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| Antioxidant properties of scopoletin isolated from Sinomonium acutum. | 2003 Aug |
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| Fc epsilon RI signaling of mast cells activates intracellular production of hydrogen peroxide: role in the regulation of calcium signals. | 2003 Dec 1 |
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| Directed immobilization of nucleic acids at ultramicroelectrodes using a novel electro-deposited polymer. | 2003 Dec 30 |
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| Influence of distillation system, oak wood type, and aging time on composition of cider brandy in phenolic and furanic compounds. | 2003 Dec 31 |
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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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| Glycosides of Atractylodes ovata. | 2003 Sep |
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| 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 Apr |
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| An active and water-soluble truncation mutant of the human UDP-glucuronosyltransferase 1A9. | 2004 Apr |
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| 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 Dec 1 |
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| 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 Dec 15 |
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| Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products. | 2004 Dec 2 |
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| Potential cancer chemopreventive constituents of the leaves of Macaranga triloba. | 2004 Feb |
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| 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 Jan |
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| Acetylcholinesterase inhibitors from the twigs of Vaccinium oldhami Miquel. | 2004 Jan |
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| Active components from Artemisia iwayomogi displaying ONOO(-) scavenging activity. | 2004 Jan |
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| Agrobacterium tumefaciens AK-6b gene modulates phenolic compound metabolism in tobacco. | 2004 Jan |
|
| Secondary metabolite content in Fabiana imbricata plants and in vitro cultures. | 2004 Jan-Feb |
|
| Phenylpropanoids, phenylalanine ammonia lyase and peroxidases in elicitor-challenged cassava (Manihot esculenta) suspension cells and leaves. | 2004 Jul |
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| Constituents of Carapa guianensis Aubl. (Meliaceae). | 2004 Jun |
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| Scopoletin suppresses pro-inflammatory cytokines and PGE2 from LPS-stimulated cell line, RAW 264.7 cells. | 2004 Jun |
|
| Anthrone and oxanthrone C-glycosides from Picramnia latifolia collected in Peru. | 2004 Mar |
|
| [Study on constituents from Neonauclea griffithii]. | 2004 May |
|
| Oxidative stress responses during cassava post-harvest physiological deterioration. | 2004 Nov |
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| Antiinflammatory activity of Synurus deltoides. | 2004 Nov |
|
| Beta-1,3 glucan sulfate, but not beta-1,3 glucan, induces the salicylic acid signaling pathway in tobacco and Arabidopsis. | 2004 Nov |
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| A new sesquiterpene lactone from Artemisia rubripes nakai. | 2004 Oct |
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| Nor-ent-kaurane diterpenes and hydroxylactones from Antennaria geyeri and Anaphalis margaritacea. | 2004 Sep |
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| Umbelliferone released from hairy root cultures of Pharbitis nil treated with copper sulfate and its subsequent glucosylation. | 2004 Sep |
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| A coumarin from Mallotus resinosus that mediates DNA cleavage. | 2004 Sep |
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| Cytotoxic constituents of roots of Chaerophyllum hirsutum. | 2004 Sep |
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| Oxidative DNA damage induced by a hydroperoxide derivative of cyclophosphamide. | 2004 Sep 15 |
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| Comparison of cytotoxicity of cysteine and homocysteine for renal epithelial cells. | 2005 |
|
| Antifungal synergistic effect of scopoletin, a hydroxycoumarin isolated from Melia azedarach L. fruits. | 2005 Apr 20 |
|
| Cytotoxic constituents of the twigs of Simarouba glauca collected from a plot in Southern Florida. | 2005 Feb |
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| Hypouricemic action of scopoletin arising from xanthine oxidase inhibition and uricosuric activity. | 2005 Feb |
|
| Total synthesis and biological activity of 13,14-dehydro-12-oxo-phytodienoic acids (deoxy-J1-phytoprostanes). | 2005 Feb |
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| B1-phytoprostanes trigger plant defense and detoxification responses. | 2005 Jan |
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| A labdane diterpene glucoside from the rhizomes of Curcuma mangga. | 2005 Jul |
|
| Kinetic characterization of the 1A subfamily of recombinant human UDP-glucuronosyltransferases. | 2005 Jul |
|
| Scopoletin induces apoptosis in human promyeloleukemic cells, accompanied by activations of nuclear factor kappaB and caspase-3. | 2005 Jul 1 |
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| Purification and characterization of a cationic peroxidase Cs in Raphanus sativus. | 2005 Jun |
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| Inhibitory effect of coumarins from Weigela subsessilis on low density lipoprotein oxidation. | 2005 Jun |
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| Simultaneous determination of active ingredients in Erigeron breviscapus (Vant.) Hand-Mazz. by capillary electrophoresis with electrochemical detection. | 2005 Mar 9 |
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| Anthraquinones from Hedyotis capitellata. | 2005 May |
|
| A new cytotoxic daphnane diterpenoid, rediocide G, from Trigonostemon reidioides. | 2005 Oct |
|
| 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
Mon Mar 31 19:43:02 GMT 2025
by
admin
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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5280460
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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 MAY BE PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT | |||
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PARENT -> CONSTITUENT ALWAYS PRESENT |
