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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 17:39:13 UTC
Update Date2019-07-23 06:07:22 UTC
HMDB IDHMDB0030818
Secondary Accession Numbers
  • HMDB30818
Metabolite Identification
Common NameScoparone
DescriptionScoparone belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one). Scoparone is a natural organic compound with the molecular formula C11H10O4. Scoparone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Scoparone is found, on average, in the highest concentration within sweet oranges and tarragons. Scoparone has also been detected, but not quantified in, several different foods, such as limes, citrus, wild celeries, mandarin orange (clementine, tangerine), and fennels. This could make scoparone a potential biomarker for the consumption of these foods.
Structure
Data?1563862042
Synonyms
ValueSource
6,7-DimethoxycoumarinKegg
6,7-Dimethoxy-2-benzopyroneHMDB
6,7-Dimethoxy-2H-1-benzopyran-2-oneHMDB
6,7-Dimethoxy-2H-chromen-2-oneHMDB
6,7-Dimethoxy-benzopyran-2-oneHMDB
6,7-Dimethoxy-coumarinHMDB, MeSH
6,7-Dimethoxybenzopyran-2-oneHMDB
6,7-DimethylesculetinHMDB, MeSH
Aesculetin dimethyl etherHMDB
Benzopyran-2-one, 6,7-dimethoxy- (9ci)HMDB
Dimethyl esculetinHMDB
DimethylaesculetinHMDB
EscoparoneHMDB
Esculetin 6,7-dimethyl etherHMDB
Esculetin dimethyl etherHMDB
O,O-DimethylesculetinHMDB
O-MethylisoscopoletinHMDB
O-MethylscopoletinHMDB
Scoparin?HMDB
ScoparonHMDB
Scopoletin methyl etherHMDB
Chemical FormulaC11H10O4
Average Molecular Weight206.197
Monoisotopic Molecular Weight206.057908802
IUPAC Name6,7-dimethoxy-2H-chromen-2-one
Traditional Namescoparone
CAS Registry Number120-08-1
SMILES
COC1=C(OC)C=C2C=CC(=O)OC2=C1
InChI Identifier
InChI=1S/C11H10O4/c1-13-9-5-7-3-4-11(12)15-8(7)6-10(9)14-2/h3-6H,1-2H3
InChI KeyGUAFOGOEJLSQBT-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as coumarins and derivatives. These are polycyclic aromatic compounds containing a 1-benzopyran moiety with a ketone group at the C2 carbon atom (1-benzopyran-2-one).
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassCoumarins and derivatives
Sub ClassNot Available
Direct ParentCoumarins and derivatives
Alternative Parents
Substituents
  • Coumarin
  • Benzopyran
  • 1-benzopyran
  • Anisole
  • 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:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point144 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.41 g/LALOGPS
logP1.8ALOGPS
logP1.47ChemAxon
logS-2.7ALOGPS
pKa (Strongest Basic)-4.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area44.76 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity54.48 m³·mol⁻¹ChemAxon
Polarizability20.38 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0bvu-6930000000-ced173387f2077948312Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7980000000-bac19c33733285c01d2eSpectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0bvu-6930000000-ced173387f2077948312Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0a4i-7980000000-bac19c33733285c01d2eSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01t9-1910000000-49576d749f9a27e74639Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-1920000000-9bd0d132645d4ed6bc1cSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-3ea9dfc965f95368cbc7Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0190000000-da5c9b027559bd7e9786Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0bvi-1910000000-dbe9795947b065d85bc1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0190000000-5054bd554f5a32a27974Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-0490000000-5077dddb7176cefd49daSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5a-3900000000-34600055b290259d617dSpectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB002774
KNApSAcK IDC00002498
Chemspider IDNot Available
KEGG Compound IDC09311
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkScoparone
METLIN IDNot Available
PubChem Compound8417
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Huang HC, Lee CR, Weng YI, Lee MC, Lee YT: Vasodilator effect of scoparone (6,7-dimethoxycoumarin) from a Chinese herb. Eur J Pharmacol. 1992 Jul 21;218(1):123-8. [PubMed:1327821 ]
  2. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .