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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H18O9
Molecular Weight 354.3087
Optical Activity UNSPECIFIED
Defined Stereocenters 5 / 5
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SCOPOLIN

SMILES

COC1=C(O[C@@H]2O[C@H](CO)[C@@H](O)[C@H](O)[C@H]2O)C=C3OC(=O)C=CC3=C1

InChI

InChIKey=SGTCGCCQZOUMJJ-YMILTQATSA-N
InChI=1S/C16H18O9/c1-22-9-4-7-2-3-12(18)23-8(7)5-10(9)24-16-15(21)14(20)13(19)11(6-17)25-16/h2-5,11,13-17,19-21H,6H2,1H3/t11-,13-,14+,15-,16-/m1/s1

HIDE SMILES / InChI

Molecular Formula C16H18O9
Molecular Weight 354.3087
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 5 / 5
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Studies on the constituents of the leaves of Morus alba L.
2001 Feb
Patterns of phenylpropanoids in non-inoculated and potato virus Y-inoculated leaves of transgenic tobacco plants expressing yeast-derived invertase.
2001 Mar
[Determination of polyphenols in tobacco by solid phase extraction and high performance liquid chromatography].
2001 Nov
Downregulation of a pathogen-responsive tobacco UDP-Glc:phenylpropanoid glucosyltransferase reduces scopoletin glucoside accumulation, enhances oxidative stress, and weakens virus resistance.
2002 May
Scaphopetalone and scaphopetalumate, a lignan and a triterpene ester from Scaphopetalum thonneri.
2003 Feb
Acetylcholinesterase inhibitory activity of scopolin and scopoletin discovered by virtual screening of natural products.
2004 Dec 2
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
Phytochemical constituents from Diodia teres.
2004 Jan
Active components from Artemisia iwayomogi displaying ONOO(-) scavenging activity.
2004 Jan
Agrobacterium tumefaciens AK-6b gene modulates phenolic compound metabolism in tobacco.
2004 Jan
Phenylpropanoids, phenylalanine ammonia lyase and peroxidases in elicitor-challenged cassava (Manihot esculenta) suspension cells and leaves.
2004 Jul
Cytotoxic activity of five compounds isolated from Colombian plants.
2004 Mar
Molecular phenotyping of the pal1 and pal2 mutants of Arabidopsis thaliana reveals far-reaching consequences on phenylpropanoid, amino acid, and carbohydrate metabolism.
2004 Oct
Ectopic expression of a UDP-glucose:phenylpropanoid glucosyltransferase leads to increased resistance of transgenic tobacco plants against infection with Potato Virus Y.
2004 Sep
A new bisabolane sesquiterpenoid from Euphorbia chrysocoma.
2005 Dec
Morning glory systemically accumulates scopoletin and scopolin after interaction with Fusarium oxysporum.
2005 Jan-Feb
Accumulation of coumarins in Arabidopsis thaliana.
2006 Feb
Growth at elevated CO2 concentrations leads to modified profiles of secondary metabolites in tobacco cv. SamsunNN and to increased resistance against infection with potato virus Y.
2006 Jan
A new C9 nor-isoprenoid glucoside from Rantherium suaveolens.
2007 Aug
Cytotoxic triterpenoid saponins from the fruits of Aesculus pavia L.
2007 Aug
Antifungal activity of a new phenolic compound from capitulum of a head rot-resistant sunflower genotype.
2007 Dec
Identification and determination of glycosides in tobacco leaves by liquid chromatography with atmospheric pressure chemical ionization tandem mass spectrometry.
2007 Feb
Structures, biogenesis, and biological activities of pyrano[4,3-c]isochromen-4-one derivatives from the Fungus Phellinus igniarius.
2007 Feb
[Studies on the chemical constituents from Inula cappa (II)].
2007 Jan
Rare biscoumarins and a chlorogenic acid derivative from Erycibe obtusifolia.
2007 Jul
[Studies on chemical constituents of Saussurea laniceps].
2008 May
A high-performance liquid chromatographic method for determination of scopolin in rat plasma: application to pharmacokinetic studies.
2008 Oct
Scopoletin is biosynthesized via ortho-hydroxylation of feruloyl CoA by a 2-oxoglutarate-dependent dioxygenase in Arabidopsis thaliana.
2008 Sep
Novel sesquiterpene and coumarin constituents from the whole herbs of Crossostephium chinense.
2009
Protein and metabolite analysis reveals permanent induction of stress defense and cell regeneration processes in a tobacco cell suspension culture.
2009 Jul 6
[Effects of chemical constituents of Crossostephium chinense on insulin secretion in rat islets in vitro].
2009 Jun
[Non-alkaloid constituents of Gelsemium elegans].
2009 Sep
[Bioactivity guided isolation of alpha-glucosidase inhibitor from whole herbs of Crossostephium chinense].
2009 Sep
Constituents and secondary metabolite natural products in fresh and deteriorated cassava roots.
2010 Apr
Cassava: an appraisal of its phytochemistry and its biotechnological prospects.
2010 Dec
Traditional herbal medicine in far-west Nepal: a pharmacological appraisal.
2010 Dec 13
Scopolin-hydrolyzing beta-glucosidases in roots of Arabidopsis.
2010 Jan
The differential spatial distribution of secondary metabolites in Arabidopsis leaves reacting hypersensitively to Pseudomonas syringae pv. tomato is dependent on the oxidative burst.
2010 Jul
Coumarins from the leaves of Bambusa pervariabilis McClure.
2010 Mar
Managing phenol contents in crop plants by phytochemical farming and breeding-visions and constraints.
2010 Mar 2
[Chemical constituents from Hydrangea paniculata].
2010 Nov
Method development and validation for the simultaneous determination of four coumarins in Saussurea superba by capillary zone electrophoresis.
2010 Sep-Oct
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 20:09:44 GMT 2023
Edited
by admin
on Fri Dec 15 20:09:44 GMT 2023
Record UNII
1Y49270PY8
Record Status Validated (UNII)
Record Version
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Name Type Language
SCOPOLIN
MI  
Common Name English
6-METHOXYCOUMARIN 7-O-.BETA.-D-GLUCOSIDE
Common Name English
SCOPOLETIN 7-GLUCOSIDE
Common Name English
SCOPOLETIN 7-O-.BETA.-D-GLUCOPYRANOSIDE
Common Name English
NSC-404560
Code English
SCOPOLOSIDE
Common Name English
SCOPOLETIN 7-O-GLUCOSIDE
Common Name English
2H-1-BENZOPYRAN-2-ONE, 7-(.BETA.-D-GLUCOPYRANOSYLOXY)-6-METHOXY-
Systematic Name English
7-O-.BETA.-GLUCOPYRANOSYLSCOPOLETIN
Common Name English
7-(.BETA.-D-GLUCOPYRANOSYLOXY)-6-METHOXYCOUMARIN
Common Name English
6-METHOXY-7-(.BETA.-D-GLUCOPYRANOSYLOXY)COUMARIN
Common Name English
SCOPOLIN [MI]
Common Name English
Code System Code Type Description
PUBCHEM
439514
Created by admin on Fri Dec 15 20:09:44 GMT 2023 , Edited by admin on Fri Dec 15 20:09:44 GMT 2023
PRIMARY
MERCK INDEX
m9816
Created by admin on Fri Dec 15 20:09:44 GMT 2023 , Edited by admin on Fri Dec 15 20:09:44 GMT 2023
PRIMARY Merck Index
CAS
531-44-2
Created by admin on Fri Dec 15 20:09:44 GMT 2023 , Edited by admin on Fri Dec 15 20:09:44 GMT 2023
PRIMARY
CHEBI
16065
Created by admin on Fri Dec 15 20:09:44 GMT 2023 , Edited by admin on Fri Dec 15 20:09:44 GMT 2023
PRIMARY
MESH
C417572
Created by admin on Fri Dec 15 20:09:44 GMT 2023 , Edited by admin on Fri Dec 15 20:09:44 GMT 2023
PRIMARY
NSC
404560
Created by admin on Fri Dec 15 20:09:44 GMT 2023 , Edited by admin on Fri Dec 15 20:09:44 GMT 2023
PRIMARY
WIKIPEDIA
Scopolin
Created by admin on Fri Dec 15 20:09:44 GMT 2023 , Edited by admin on Fri Dec 15 20:09:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID20967621
Created by admin on Fri Dec 15 20:09:44 GMT 2023 , Edited by admin on Fri Dec 15 20:09:44 GMT 2023
PRIMARY
FDA UNII
1Y49270PY8
Created by admin on Fri Dec 15 20:09:44 GMT 2023 , Edited by admin on Fri Dec 15 20:09:44 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> CONSTITUENT ALWAYS PRESENT