Showing Compound Card for Scopoletin (CDB005047)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Created at2020-04-17 19:03:58 UTC
Updated at2020-11-18 16:39:15 UTC
CannabisDB IDCDB005047
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameScopoletin
DescriptionScopoletin, also known as 6-methylesculetin or acid, gelseminic, belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton. Scopoletin is an extremely weak basic (essentially neutral) compound (based on its pKa). Scopoletin exists in all living organisms, ranging from bacteria to humans. Outside of the human body, Scopoletin is found, on average, in the highest concentration within a few different foods, such as anises, oats, and sherries. Scopoletin has also been detected, but not quantified in, several different foods, such as barley, tarragons, mung beans, figs, and pepper (c. annuum). This could make scopoletin a potential biomarker for the consumption of these foods. A hydroxycoumarin that is umbelliferone bearing a methoxy substituent at position 6. Scopoletin is expected to be in Cannabis as all living plants are known to produce and metabolize it.
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
6-Methoxy-7-hydroxycoumarinChEBI
6-MethylesculetinChEBI
6-O-MethylesculetinChEBI
7-Hydroxy-6-methoxy-2H-1-benzopyran-2-oneChEBI
7-Hydroxy-6-methoxycoumarinChEBI
7-Hydroxy-6-methoxy-2H-chromen-2-oneKegg
2H-1-Benzopyran-2-one, 7-hydroxy-6-methoxy- (9ci)HMDB
6-MethoxyumbelliferoneHMDB
7-Hydroxy-5-methoxycoumarinHMDB
7-Hydroxy-6-methoxy-coumarinHMDB
Acid, chrysotropicHMDB, MeSH
Acid, gelseminicHMDB, MeSH
Aesculetin 6-methyl etherHMDB
b-MethylaesculetinHMDB
Baogongteng bHMDB
beta -MethylesculetinHMDB
beta-MethylesculetinHMDB
BuxuletinHMDB
Chrysatropic acidHMDB
Chrysotropic acidHMDB, MeSH
EscopoletinHMDB
Esculetin 6-methyl etherHMDB
Esculetin-6-methyl etherHMDB
Gelseminic acidHMDB, MeSH
MethylesculetinHMDB, MeSH
MurrayetinHMDB
ScopoletineHMDB
ScopoletolHMDB
Chemical FormulaC10H8O4
Average Molecular Weight192.17
Monoisotopic Molecular Weight192.0423
IUPAC Name7-hydroxy-6-methoxy-2H-chromen-2-one
Traditional Namescopoletin
CAS Registry Number92-61-5
SMILES
COC1=C(O)C=C2OC(=O)C=CC2=C1
InChI Identifier
InChI=1S/C10H8O4/c1-13-9-4-6-2-3-10(12)14-8(6)5-7(9)11/h2-5,11H,1H3
InChI KeyRODXRVNMMDRFIK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassHydroxycoumarins
Direct Parent7-hydroxycoumarins
Alternative Parents
Substituents
  • 7-hydroxycoumarin
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Pyranone
  • Pyran
  • Benzenoid
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • Ether
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Route of exposure:

Source:

Biological location:

Role

Biological role:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point204 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.65ALOGPS
logP1.32ChemAxon
logS-1.9ALOGPS
pKa (Strongest Acidic)8.26ChemAxon
pKa (Strongest Basic)-4.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area55.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity49.99 m³·mol⁻¹ChemAxon
Polarizability18.31 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-002f-4900000000-b5bdf737b69c5cd7c5aa2015-03-01View Spectrum
GC-MSScopoletin, 1 TMS, GC-MS Spectrumsplash10-053r-2490000000-c200887014ff29ef3a8fSpectrum
GC-MSScopoletin, non-derivatized, GC-MS Spectrumsplash10-053r-2490000000-c200887014ff29ef3a8fSpectrum
GC-MSScopoletin, non-derivatized, GC-MS Spectrumsplash10-053r-1490000000-2146bc4f0afceba80b06Spectrum
Predicted GC-MSScopoletin, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-03dj-0900000000-46efa588a7f66072d294Spectrum
Predicted GC-MSScopoletin, 1 TMS, Predicted GC-MS Spectrum - 70eV, Positivesplash10-00di-2290000000-2215044fdc455cf39861Spectrum
Predicted GC-MSScopoletin, non-derivatized, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-004i-0000092000-fe08120bacfe47df17f22017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0903000010-279e9ecfac68f75b37fd2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0903000010-279e9ecfac68f75b37fd2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0903000010-279e9ecfac68f75b37fd2017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0901000000-f56262960dba956afd502017-08-14View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0uk9-0900000000-37644bdb4253d408730b2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0903000010-279e9ecfac68f75b37fd2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004l-0900000000-0725f844ed58b7b3db242017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0900000000-f55cc5686f36a2c31bdf2017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0092-0900000000-2371c5d87e204b2f31872017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0901000000-f56262960dba956afd502017-09-12View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0fh9-0900000000-9ee871d32b4eb22529b82017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-94eacbe24073498f4dcc2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-18a42b21822b016c32ce2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-1dd9600ca8db6c98239b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0900000000-c13de07771b151ebed9e2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0uk9-0900000000-37644bdb4253d408730b2017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004l-0900000000-0725f844ed58b7b3db242017-09-14View Spectrum
MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0900000000-f55cc5686f36a2c31bdf2017-09-14View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-ce78be779b8108ca1e102015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-5364ea5b64704765d3f42015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-1900000000-d4ccdf4b37aff5a773772015-04-24View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-bd8785dd1cd0807268bd2015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-8521e4d80e5fe256bb812015-04-25View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o1-1900000000-aa4c65b1940903b4e3e62015-04-25View Spectrum
NMR
TypeDescriptionView
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)Spectrum
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
UDP-glucuronosyltransferase 1-1UGT1A12q37P22309 details
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0034344
DrugBank IDNot Available
Phenol Explorer Compound ID638
FoodDB IDFDB012705
KNApSAcK IDC00002499
Chemspider ID4444113
KEGG Compound IDC01752
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkScopoletin
METLIN IDNot Available
PubChem Compound5280460
PDB IDNot Available
ChEBI ID17488
References
General ReferencesNot Available

Enzymes

Enzyme Details
1. UDP-glucuronosyltransferase 1-1
General function:
Involved in transferase activity, transferring hexosyl groups
Specific function:
UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the IX-alpha-C8 and IX-alpha-C12 monoconjugates and diconjugate. Is also able to catalyze the glucuronidation of 17beta-estradiol, 17alpha-ethinylestradiol, 1-hydroxypyrene, 4-methylumbelliferone, 1-naphthol, paranitrophenol, scopoletin, and umbelliferone.
Gene Name:
UGT1A1
Uniprot ID:
P22309
Molecular weight:
59590.91