Record Information
Version1.0
Creation date2010-04-08 22:10:01 UTC
Update date2019-11-26 03:06:19 UTC
Primary IDFDB012168
Secondary Accession NumbersNot Available
Chemical Information
FooDB NameScopolin
DescriptionScopolin is a member of the class of compounds known as coumarin glycosides. Coumarin glycosides are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety. Scopolin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Scopolin can be found in a number of food items such as sweet potato, oat, wild celery, and potato, which makes scopolin a potential biomarker for the consumption of these food products. Scopolin is a glucoside of scopoletin formed by the action of the enzyme scopoletin glucosyltransferase .
CAS Number531-44-2
Structure
Thumb
Synonyms
Predicted Properties
PropertyValueSource
Water Solubility5.61 g/LALOGPS
logP-0.56ALOGPS
logP-0.95ChemAxon
logS-1.8ALOGPS
pKa (Strongest Acidic)12.2ChemAxon
pKa (Strongest Basic)-3ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count8ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area134.91 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity82.14 m³·mol⁻¹ChemAxon
Polarizability33.65 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Chemical FormulaC16H18O9
IUPAC name6-methoxy-7-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2H-chromen-2-one
InChI IdentifierInChI=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
InChI KeySGTCGCCQZOUMJJ-UHFFFAOYSA-N
Isomeric SMILESCOC1=CC2=C(OC(=O)C=C2)C=C1OC1OC(CO)C(O)C(O)C1O
Average Molecular Weight354.3087
Monoisotopic Molecular Weight354.095082174
Classification
Description Belongs to the class of organic compounds known as coumarin glycosides. These are aromatic compounds containing a carbohydrate moiety glycosidically bound to a coumarin moiety.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassCoumarin glycosides
Direct ParentCoumarin glycosides
Alternative Parents
Substituents
  • Coumarin-7-o-glycoside
  • Coumarin o-glycoside
  • Phenolic glycoside
  • Hexose monosaccharide
  • Glycosyl compound
  • O-glycosyl compound
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • Alkyl aryl ether
  • Pyranone
  • Benzenoid
  • Monosaccharide
  • Oxane
  • Pyran
  • Heteroaromatic compound
  • Secondary alcohol
  • Lactone
  • Acetal
  • Organoheterocyclic compound
  • Ether
  • Oxacycle
  • Polyol
  • Organooxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Organic oxygen compound
  • Primary alcohol
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
OntologyNo ontology term
Physico-Chemical Properties
Physico-Chemical Properties - Experimental
Spectra
Spectra
EI-MS/GC-MSNot Available
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0907000000-03591ff21234792c11d22016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-d493445e19491b88fbd82016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-1900000000-bb497c4a1947e63d8e8b2016-06-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udl-1619000000-08cae2cb30ff5c1f9e602016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-1912000000-4a678bacd1e80bcd96f02016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004m-1900000000-7fb5d3529ee331c5c3172016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0904000000-b26534126ef22da7c37a2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0901000000-306f58175a4be02dc16d2021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-4940000000-cb6707468f7d80f853c22021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0309000000-467a8018d608fcb3ac462021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fbc-2945000000-a3a76507241adf8effc12021-10-21View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-2901000000-dc569781a728ec97a7f62021-10-21View Spectrum
NMRNot Available
ChemSpider IDNot Available
ChEMBL IDNot Available
KEGG Compound IDC01527
Pubchem Compound ID346340
Pubchem Substance IDNot Available
ChEBI ID16065
Phenol-Explorer IDNot Available
DrugBank IDNot Available
HMDB IDNot Available
CRC / DFC (Dictionary of Food Compounds) IDHJZ66-A:HDW78-A
EAFUS IDNot Available
Dr. Duke IDSCOPOLIN|SCOPOLETIN-7-GLUCOSIDE
BIGG IDNot Available
KNApSAcK IDC00002500
HET IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
Processing...
Biological Effects and Interactions
Health Effects / Bioactivities
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).