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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
Structure of SCOPOLETIN

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

HIDE SMILES / InChI

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.

CNS Activity

Curator's Comment:: referenced study was conducted on mice

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment:: referenced study was conducted on rats.
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 Sat Jun 26 03:59:00 UTC 2021
Edited
by admin
on Sat Jun 26 03:59:00 UTC 2021
Record UNII
KLF1HS0SXJ
Record Status Validated (UNII)
Record Version
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Name Type Language
SCOPOLETIN
MI   USP-RS  
Common Name English
GELSEMINIC ACID
Common Name English
SCOPOLETIN [USP-RS]
Common Name English
6-O-METHYLESCULETIN
Common Name English
6-METHYLESCULETIN
Common Name English
CHRYSATROPIC ACID
Common Name English
SCOPOLETIN [MI]
Common Name English
SCOPOLETIN (CONSTITUENT OF STINGING NETTLE) [DSC]
Common Name English
ESCULETIN 6-METHYL ETHER
Common Name English
MURRAYETIN
Common Name English
NSC-405647
Code English
SCOPOLETINE
Common Name English
.BETA.-METHYLESCULETIN
Common Name English
7-HYDROXY-6-METHOXY-2H-1-BENZOPYRAN-2-ONE
Systematic Name English
ESCOPOLETIN
Common Name English
COPOLETIN
Common Name English
7-HYDROXY-6-METHOXYCOUMARIN
Systematic Name English
SCOPOLETOL
Common Name English
6-METHOXY-7-HYDROXYCOUMARIN
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C45597
Created by admin on Sat Jun 26 03:59:00 UTC 2021 , Edited by admin on Sat Jun 26 03:59:00 UTC 2021
Code System Code Type Description
EPA CompTox
92-61-5
Created by admin on Sat Jun 26 03:59:00 UTC 2021 , Edited by admin on Sat Jun 26 03:59:00 UTC 2021
PRIMARY
MERCK INDEX
M9815
Created by admin on Sat Jun 26 03:59:00 UTC 2021 , Edited by admin on Sat Jun 26 03:59:00 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
SCOPOLETIN
Created by admin on Sat Jun 26 03:59:00 UTC 2021 , Edited by admin on Sat Jun 26 03:59:00 UTC 2021
PRIMARY
CAS
92-61-5
Created by admin on Sat Jun 26 03:59:00 UTC 2021 , Edited by admin on Sat Jun 26 03:59:00 UTC 2021
PRIMARY
FDA UNII
KLF1HS0SXJ
Created by admin on Sat Jun 26 03:59:00 UTC 2021 , Edited by admin on Sat Jun 26 03:59:00 UTC 2021
PRIMARY
PUBCHEM
5280460
Created by admin on Sat Jun 26 03:59:00 UTC 2021 , Edited by admin on Sat Jun 26 03:59:00 UTC 2021
PRIMARY
MESH
D012603
Created by admin on Sat Jun 26 03:59:00 UTC 2021 , Edited by admin on Sat Jun 26 03:59:00 UTC 2021
PRIMARY
NCI_THESAURUS
C126100
Created by admin on Sat Jun 26 03:59:00 UTC 2021 , Edited by admin on Sat Jun 26 03:59:00 UTC 2021
PRIMARY
USP_CATALOG
1610090
Created by admin on Sat Jun 26 03:59:00 UTC 2021 , Edited by admin on Sat Jun 26 03:59:00 UTC 2021
PRIMARY USP-RS
ECHA (EC/EINECS)
202-171-9
Created by admin on Sat Jun 26 03:59:00 UTC 2021 , Edited by admin on Sat Jun 26 03:59:00 UTC 2021
PRIMARY
Related Record Type Details
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