Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C10H8O4 |
| Molecular Weight | 192.1685 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
COc1cc2ccc(=O)oc2cc1O
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 | 192.1685 |
| 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 |
|||
| Primary | Unknown Approved UseUnknown |
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| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Study on the constituents from Neonauclea sessilifolia]. | 2002 Dec |
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| [Studies on immunocompetent constituents of Patrinia scabra Bunge]. | 2002 Mar |
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| [Prediction of eluotropic sequence of solutes in countercurrent chromatography]. | 2002 Nov |
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| [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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| High-performance liquid chromatography determination of methionine adenosyltransferase activity using catechol-O-methyltransferase-coupled fluorometric detection. | 2003 Aug 1 |
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| Directed immobilization of nucleic acids at ultramicroelectrodes using a novel electro-deposited polymer. | 2003 Dec 30 |
|
| Influence of distillation system, oak wood type, and aging time on composition of cider brandy in phenolic and furanic compounds. | 2003 Dec 31 |
|
| A polyacetylene and flavonoids from Cirsium rhinoceros. | 2003 Feb |
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| Sulfated fucan oligosaccharides elicit defense responses in tobacco and local and systemic resistance against tobacco mosaic virus. | 2003 Feb |
|
| Scaphopetalone and scaphopetalumate, a lignan and a triterpene ester from Scaphopetalum thonneri. | 2003 Feb |
|
| Potential functional foods in the traditional Maori diet. | 2003 Feb-Mar |
|
| Study on the determination of polyphenols in tobacco by HPLC coupled with ESI-MS after solid-phase extraction. | 2003 Jan |
|
| 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 |
|
| Glucuronidation activity of the UGT2B17 enzyme toward xenobiotics. | 2003 May |
|
| DNA damage by ethylbenzenehydroperoxide formed from carcinogenic ethylbenzene by sunlight irradiation. | 2003 May 16 |
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| An active and water-soluble truncation mutant of the human UDP-glucuronosyltransferase 1A9. | 2004 Apr |
|
| 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 |
|
| 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 |
|
| 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 |
|
| Phenylpropanoids, phenylalanine ammonia lyase and peroxidases in elicitor-challenged cassava (Manihot esculenta) suspension cells and leaves. | 2004 Jul |
|
| Constituents of Carapa guianensis Aubl. (Meliaceae). | 2004 Jun |
|
| 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 |
|
| Beta-1,3 glucan sulfate, but not beta-1,3 glucan, induces the salicylic acid signaling pathway in tobacco and Arabidopsis. | 2004 Nov |
|
| Nor-ent-kaurane diterpenes and hydroxylactones from Antennaria geyeri and Anaphalis margaritacea. | 2004 Sep |
|
| Umbelliferone released from hairy root cultures of Pharbitis nil treated with copper sulfate and its subsequent glucosylation. | 2004 Sep |
|
| A coumarin from Mallotus resinosus that mediates DNA cleavage. | 2004 Sep |
|
| Cytotoxic constituents of roots of Chaerophyllum hirsutum. | 2004 Sep |
|
| Comparison of cytotoxicity of cysteine and homocysteine for renal epithelial cells. | 2005 |
|
| 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 |
|
| A new antipsychotic effective neolignan from Firmiana simplex. | 2005 Jan |
|
| [Determination of scopoletin and umbelliferone contents in Saussurea medusa Maxim by high-performance liquid chromatography]. | 2005 Jan |
|
| B1-phytoprostanes trigger plant defense and detoxification responses. | 2005 Jan |
|
| Morning glory systemically accumulates scopoletin and scopolin after interaction with Fusarium oxysporum. | 2005 Jan-Feb |
|
| 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 |
|
| [Effect of caffeic acid, seopoletin and scutellarin on rat retinal neurons in vitro]. | 2005 Jun |
|
| Purification and characterization of a cationic peroxidase Cs in Raphanus sativus. | 2005 Jun |
|
| Metabolite fingerprinting in transgenic Nicotiana tabacum altered by the Escherichia coli glutamate dehydrogenase gene. | 2005 Jun 30 |
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| Acylperoxylated and seco-mexicanolides from stems of Khaya anthotheca. | 2005 Mar |
|
| Simultaneous determination of active ingredients in Erigeron breviscapus (Vant.) Hand-Mazz. by capillary electrophoresis with electrochemical detection. | 2005 Mar 9 |
|
| 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
by
admin
on
Edited
Sat Jun 26 03:59:00 UTC 2021
by
admin
on
Sat Jun 26 03:59:00 UTC 2021
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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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| Code System | Code | Type | Description | ||
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92-61-5
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M9815
Created by
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PRIMARY | Merck Index | ||
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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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1610090
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202-171-9
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