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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:09:38 UTC
Update Date2019-07-23 06:15:48 UTC
HMDB IDHMDB0034344
Secondary Accession Numbers
  • HMDB34344
Metabolite 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 in a few different foods, such as anises, oats, and sherries and in a lower concentration in . scopoletin has also been detected, but not quantified in, several different foods, such as green vegetables, carrots, tarragons, orange bell peppers, and pepper (c. frutescens). 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.
Structure
Data?1563862548
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
Acid, gelseminicHMDB
Aesculetin 6-methyl etherHMDB
b-MethylaesculetinHMDB
Baogongteng bHMDB
beta -MethylesculetinHMDB
beta-MethylesculetinHMDB
BuxuletinHMDB
Chrysatropic acidHMDB
Chrysotropic acidHMDB
EscopoletinHMDB
Esculetin 6-methyl etherHMDB
Esculetin-6-methyl etherHMDB
Gelseminic acidHMDB
MethylesculetinHMDB
MurrayetinHMDB
ScopoletineHMDB
ScopoletolHMDB
Chemical FormulaC10H8O4
Average Molecular Weight192.17
Monoisotopic Molecular Weight192.042258738
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
Water Solubility2.35 g/LALOGPS
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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - GC-MS (1 TMS)splash10-053r-2490000000-c200887014ff29ef3a8fSpectrum
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-053r-2490000000-c200887014ff29ef3a8fSpectrum
GC-MSGC-MS Spectrum - GC-EI-TOF (Non-derivatized)splash10-053r-1490000000-2146bc4f0afceba80b06Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-0900000000-46efa588a7f66072d294Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00di-2290000000-2215044fdc455cf39861Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-004i-0000092000-fe08120bacfe47df17f2Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0903000010-279e9ecfac68f75b37fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0903000010-279e9ecfac68f75b37fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-004i-0903000010-279e9ecfac68f75b37fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0901000000-f56262960dba956afd50Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 40V, Negativesplash10-0uk9-0900000000-37644bdb4253d408730bSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0903000010-279e9ecfac68f75b37fdSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004l-0900000000-0725f844ed58b7b3db24Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-004i-0900000000-f55cc5686f36a2c31bdfSpectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0092-0900000000-2371c5d87e204b2f3187Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0006-0901000000-f56262960dba956afd50Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0fh9-0900000000-9ee871d32b4eb22529b8Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-94eacbe24073498f4dccSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-18a42b21822b016c32ceSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-004i-0900000000-1dd9600ca8db6c98239bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0udi-0900000000-c13de07771b151ebed9eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-0uk9-0900000000-37644bdb4253d408730bSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004l-0900000000-0725f844ed58b7b3db24Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-004i-0900000000-f55cc5686f36a2c31bdfSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-0900000000-ce78be779b8108ca1e10Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0006-0900000000-5364ea5b64704765d3f4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-004j-1900000000-d4ccdf4b37aff5a77377Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0006-0900000000-bd8785dd1cd0807268bdSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0006-0900000000-8521e4d80e5fe256bb81Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00o1-1900000000-aa4c65b1940903b4e3e6Spectrum
MSMass Spectrum (Electron Ionization)splash10-002f-4900000000-b5bdf737b69c5cd7c5aaSpectrum
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 ID638
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General References
  1. (). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

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
Reactions
Scopoletin → 3,4,5-trihydroxy-6-[(6-methoxy-2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic aciddetails