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 |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| New indole alkaloids from Sarcocephalus latifolius. | 2001 |
|
| Quassinoids from Eurycoma harmandiana. | 2001 Aug |
|
| Terpenoids from Guarea rhophalocarpa. | 2001 Jan |
|
| Cr (VI) induces cell growth arrest through hydrogen peroxide-mediated reactions. | 2001 Jun |
|
| [Studies on chemical constituents from the herb of Peucedanum decursivum (Miq.) Maxim]. | 2001 Mar |
|
| Effects of scopoletin and aflatoxin B1 on bovine hepatic mitochondrial respiratory complexes, 2: a-ketoglutarate cytochrome c and succinate cytochrome c reductases. | 2001 Mar-Apr |
|
| Phenolic compounds with anti-inflammatory activity from Eupatorium buniifolium. | 2001 Nov |
|
| Purification and characterization of a cationic isoperoxidase from scented-geranium. | 2001 Nov |
|
| Coumarins with monoamine oxidase inhibitory activity and antioxidative coumarino-lignans from Hibiscus syriacus. | 2001 Sep |
|
| Inhibitory effects of phenylpropanoid metabolites on copper-induced protein oxidative modification of mice brain homogenate, in vitro. | 2002 Feb |
|
| Two new chlorinated amides from Nicotiana glauca R. Graham. | 2002 Mar |
|
| Downregulation of a pathogen-responsive tobacco UDP-Glc:phenylpropanoid glucosyltransferase reduces scopoletin glucoside accumulation, enhances oxidative stress, and weakens virus resistance. | 2002 May |
|
| Generation of reactive oxygen species in the enzymatic reduction of PbCrO4 and related DNA damage. | 2002 May-Jun |
|
| [Prediction of eluotropic sequence of solutes in countercurrent chromatography]. | 2002 Nov |
|
| Three new jatrophane-type diterpenes from Euphorbia pubescens. | 2003 Apr |
|
| 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 |
|
| Fc epsilon RI signaling of mast cells activates intracellular production of hydrogen peroxide: role in the regulation of calcium signals. | 2003 Dec 1 |
|
| Potential functional foods in the traditional Maori diet. | 2003 Feb-Mar |
|
| Molecular cloning and biological activity of alpha-, beta-, and gamma-megaspermin, three elicitins secreted by Phytophthora megasperma H20. | 2003 Jan |
|
| Glycosides of Atractylodes ovata. | 2003 Sep |
|
| Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products. | 2004 Dec 2 |
|
| Potential cancer chemopreventive constituents of the leaves of Macaranga triloba. | 2004 Feb |
|
| 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 |
|
| Anthrone and oxanthrone C-glycosides from Picramnia latifolia collected in Peru. | 2004 Mar |
|
| Oxidative DNA damage induced by a hydroperoxide derivative of cyclophosphamide. | 2004 Sep 15 |
|
| Cytotoxic constituents of the twigs of Simarouba glauca collected from a plot in Southern Florida. | 2005 Feb |
|
| Total synthesis and biological activity of 13,14-dehydro-12-oxo-phytodienoic acids (deoxy-J1-phytoprostanes). | 2005 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 |
|
| Scopoletin induces apoptosis in human promyeloleukemic cells, accompanied by activations of nuclear factor kappaB and caspase-3. | 2005 Jul 1 |
|
| [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 |
|
| Acylperoxylated and seco-mexicanolides from stems of Khaya anthotheca. | 2005 Mar |
|
| 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
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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92-61-5
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M9815
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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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