Record Information
Version1.0
Creation date2010-04-08 22:10:01 UTC
Update date2018-05-28 23:34:37 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
SynonymSource
Murrayindb_source
Scopoletin 7-glucosidebiospider
Scopolindb_source
Scopolosidebiospider
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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
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
DescriptionThis compound 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 o-glycoside
  • Coumarin-7-o-glycoside
  • Phenolic glycoside
  • O-glycosyl compound
  • Glycosyl compound
  • 1-benzopyran
  • Benzopyran
  • Anisole
  • Pyranone
  • Alkyl aryl ether
  • Benzenoid
  • Pyran
  • Oxane
  • Monosaccharide
  • Saccharide
  • Heteroaromatic compound
  • Secondary alcohol
  • Polyol
  • Lactone
  • 1,2-diol
  • Oxacycle
  • Organoheterocyclic compound
  • Monocarboxylic acid or derivatives
  • Ether
  • Acetal
  • Hydrocarbon derivative
  • Primary alcohol
  • Organooxygen compound
  • Alcohol
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 54.24%; H 5.12%; O 40.64%DFC
Melting PointMp 217-219°DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKaNot Available
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data340 (e 9800) (MeOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052f-0907000000-03591ff21234792c11d2View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-d493445e19491b88fbd8View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004l-1900000000-bb497c4a1947e63d8e8bView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udl-1619000000-08cae2cb30ff5c1f9e60View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-002f-1912000000-4a678bacd1e80bcd96f0View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004m-1900000000-7fb5d3529ee331c5c317View in MoNA
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
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
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
anti cholinergic38323 Any drug used for its actions on cholinergic systems. Included here are agonists and antagonists, drugs that affect the life cycle of acetylcholine, and drugs that affect the survival of cholinergic neurons.DUKE
broncho elaxant52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
central nervous system depressant35470 A class of drugs producing both physiological and psychological effects through a variety of mechanisms involving the central nervous system.DUKE
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).