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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-11 19:09:38 UTC
Update Date2022-03-07 02:54:04 UTC
HMDB IDHMDB0034344
Secondary Accession Numbers
  • HMDB34344
Metabolite Identification
Common NameScopoletin
DescriptionScopoletin, also known as 6-methylesculetin, 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 exists in all living organisms, ranging from bacteria to humans. Scopoletin is found, on average, in the highest concentration within a few different foods, such as anises (Pimpinella anisum), andean blackberries (Rubus glaucus), and blackberries (Rubus) and in a lower concentration in tropical highland blackberries (Rubus adenotrichos), oats (Avena sativa), and sherry. Scopoletin has also been detected, but not quantified in, several different foods, such as grass peas (Lathyrus sativus), lantern fruits (Physalis alkekengi), pita bread, sweet cherries (Prunus avium), and pepper (capsicum). This could make scopoletin a potential biomarker for the consumption of these foods. Scopoletin is a secondary metabolite. Secondary metabolites are metabolically or physiologically non-essential metabolites that may serve a role as defense or signalling molecules. In some cases they are simply molecules that arise from the incomplete metabolism of other secondary metabolites. Based on a literature review a significant number of articles have been published on Scopoletin.
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, 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 Weight192.042258738
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

Biological location

Source

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point204 °CNot Available
Boiling Point410.80 °C. @ 760.00 mm Hg (est)The Good Scents Company Information System
Water Solubility1000000 mg/L @ 25 °C (est)The Good Scents Company Information System
LogP-1.880 (est)The Good Scents Company Information System
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available133.603http://allccs.zhulab.cn/database/detail?ID=AllCCS00001473
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+142.56831661259
DarkChem[M-H]-142.23131661259
DeepCCS[M+H]+143.8230932474
DeepCCS[M-H]-141.46230932474
DeepCCS[M-2H]-176.09930932474
DeepCCS[M+Na]+151.54530932474
AllCCS[M+H]+139.832859911
AllCCS[M+H-H2O]+135.432859911
AllCCS[M+NH4]+143.932859911
AllCCS[M+Na]+145.132859911
AllCCS[M-H]-139.832859911
AllCCS[M+Na-2H]-139.932859911
AllCCS[M+HCOO]-140.132859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
ScopoletinCOC1=C(O)C=C2OC(=O)C=CC2=C12996.9Standard polar33892256
ScopoletinCOC1=C(O)C=C2OC(=O)C=CC2=C11874.9Standard non polar33892256
ScopoletinCOC1=C(O)C=C2OC(=O)C=CC2=C11965.8Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Scopoletin,1TMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C)OC(=O)C=C22095.0Semi standard non polar33892256
Scopoletin,1TBDMS,isomer #1COC1=CC2=C(C=C1O[Si](C)(C)C(C)(C)C)OC(=O)C=C22348.9Semi standard non polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Scopoletin GC-MS (1 TMS)splash10-053r-2490000000-c200887014ff29ef3a8f2014-06-16HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Scopoletin GC-MS (Non-derivatized)splash10-053r-2490000000-c200887014ff29ef3a8f2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Scopoletin GC-EI-TOF (Non-derivatized)splash10-053r-1490000000-2146bc4f0afceba80b062017-09-12HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Scopoletin GC-MS (Non-derivatized) - 70eV, Positivesplash10-03dj-0900000000-46efa588a7f66072d2942017-07-27Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Scopoletin GC-MS (1 TMS) - 70eV, Positivesplash10-00di-2290000000-2215044fdc455cf398612017-10-06Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Scopoletin GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-002f-4900000000-b5bdf737b69c5cd7c5aa2015-03-01Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin ESI-TOF 40V, Negative-QTOFsplash10-004i-0000092000-fe08120bacfe47df17f22017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin ESI-TOF 10V, Negative-QTOFsplash10-004i-0903000010-279e9ecfac68f75b37fd2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin ESI-TOF 20V, Negative-QTOFsplash10-004i-0903000010-279e9ecfac68f75b37fd2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin ESI-TOF 30V, Negative-QTOFsplash10-004i-0903000010-279e9ecfac68f75b37fd2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin ESI-TOF , Negative-QTOFsplash10-0006-0901000000-f56262960dba956afd502017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin ESI-TOF 40V, Negative-QTOFsplash10-0uk9-0900000000-37644bdb4253d408730b2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin ESI-TOF 10V, Negative-QTOFsplash10-004i-0903000010-279e9ecfac68f75b37fd2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin ESI-TOF 10V, Negative-QTOFsplash10-004l-0900000000-0725f844ed58b7b3db242017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin ESI-TOF 20V, Negative-QTOFsplash10-004i-0900000000-f55cc5686f36a2c31bdf2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin ESI-TOF 30V, Negative-QTOFsplash10-0092-0900000000-2371c5d87e204b2f31872017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin ESI-TOF , Negative-QTOFsplash10-0006-0901000000-f56262960dba956afd502017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin LC-ESI-qTof , Positive-QTOFsplash10-0fh9-0900000000-9ee871d32b4eb22529b82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin LC-ESI-QTOF , negative-QTOFsplash10-004i-0900000000-94eacbe24073498f4dcc2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin LC-ESI-QTOF , negative-QTOFsplash10-004i-0900000000-18a42b21822b016c32ce2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin LC-ESI-QTOF , negative-QTOFsplash10-004i-0900000000-1dd9600ca8db6c98239b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin LC-ESI-QTOF , negative-QTOFsplash10-0udi-0900000000-c13de07771b151ebed9e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin LC-ESI-TOF , negative-QTOFsplash10-0uk9-0900000000-37644bdb4253d408730b2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin LC-ESI-TOF , negative-QTOFsplash10-004l-0900000000-0725f844ed58b7b3db242017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Scopoletin LC-ESI-TOF , negative-QTOFsplash10-004i-0900000000-f55cc5686f36a2c31bdf2017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Scopoletin 10V, Positive-QTOFsplash10-0006-0900000000-ce78be779b8108ca1e102015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Scopoletin 20V, Positive-QTOFsplash10-0006-0900000000-5364ea5b64704765d3f42015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Scopoletin 40V, Positive-QTOFsplash10-004j-1900000000-d4ccdf4b37aff5a773772015-04-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Scopoletin 10V, Negative-QTOFsplash10-0006-0900000000-bd8785dd1cd0807268bd2015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Scopoletin 20V, Negative-QTOFsplash10-0006-0900000000-8521e4d80e5fe256bb812015-04-25Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Scopoletin 40V, Negative-QTOFsplash10-00o1-1900000000-aa4c65b1940903b4e3e62015-04-25Wishart LabView Spectrum

NMR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted 1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
Predicted 1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-25Wishart LabView Spectrum
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
MarkerDB IDNot Available
Good Scents IDrw1495271
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