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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
[Study on the constituents from Neonauclea sessilifolia].
2002 Dec
[Studies on immunocompetent constituents of Patrinia scabra Bunge].
2002 Mar
[Prediction of eluotropic sequence of solutes in countercurrent chromatography].
2002 Nov
[Studies on chemical constitutes of Phellinus igniarius].
2003 Apr
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
Antioxidant properties of scopoletin isolated from Sinomonium acutum.
2003 Aug
High-performance liquid chromatography determination of methionine adenosyltransferase activity using catechol-O-methyltransferase-coupled fluorometric detection.
2003 Aug 1
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
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
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
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
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
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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