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Record Information
Version5.0
StatusDetected and Quantified
Creation Date2012-09-11 17:33:07 UTC
Update Date2020-07-17 21:45:36 UTC
HMDB IDHMDB0029865
Secondary Accession Numbers
  • HMDB29865
Metabolite Identification
Common NameUmbelliferone
DescriptionUmbelliferone, also known as 7-hydroxycoumarin or hydrangin, 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. Umbelliferone is an extremely weak basic (essentially neutral) compound (based on its pKa). Outside of the human body, Umbelliferone is found, on average, in the highest concentration within anises and beers. Umbelliferone has also been detected, but not quantified in, several different foods, such as common buckwheats, sweet oranges, red beetroots, kohlrabis, and wild celeries. This could make umbelliferone a potential biomarker for the consumption of these foods. A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.
Structure
Data?1595022336
Synonyms
ValueSource
7-Hydroxy-2H-1-benzopyran-2-oneChEBI
7-HydroxycoumarinChEBI
beta-UmbelliferoneChEBI
HydranginChEBI
SkimmetinChEBI
b-UmbelliferoneGenerator
Β-umbelliferoneGenerator
7-Hydroxy-2H-chromen-2-oneHMDB
7-Hydroxy-coumarinHMDB
7-Hydroxycoumarin sulfateHMDB
7-Hydroxycoumarin sulphateHMDB
7-Hydroxycoumarin, 14C-labeledHMDB
7-OxycoumarinHMDB
beta -UmbelliferoneHMDB
HydrangineHMDB
SkimmetineHMDB
UmbelliferonHMDB
Umbelliferone (hydrangin, skimmetin)HMDB
Chemical FormulaC9H6O3
Average Molecular Weight162.144
Monoisotopic Molecular Weight162.031694053
IUPAC Name7-hydroxy-2H-chromen-2-one
Traditional Nameumbelliferone
CAS Registry Number93-35-6
SMILES
OC1=CC2=C(C=C1)C=CC(=O)O2
InChI Identifier
InChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H
InChI KeyORHBXUUXSCNDEV-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
  • 1-hydroxy-2-unsubstituted benzenoid
  • Pyranone
  • Benzenoid
  • Pyran
  • Heteroaromatic compound
  • Lactone
  • Oxacycle
  • 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 Molecular Properties
PropertyValueReference
Melting Point230 - 232 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility4.38 g/LALOGPS
logP1.85ALOGPS
logP1.48ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)7.84ChemAxon
pKa (Strongest Basic)-6.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity43.53 m³·mol⁻¹ChemAxon
Polarizability15.37 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Collision Cross Sections

NameAdductTypeData SourceValueReference
DeepCCS[M-H]-ExperimentalBaker130.56530932474
AllCCS[M-H]-ExperimentalNot Available130.565http://allccs.zhulab.cn/database/detail?ID=AllCCS00001940
DarkChem[M+H]+PredictedNot Available132.63231661259
DarkChem[M-H]-PredictedNot Available130.01831661259

Retention Indices

Underivatized

Not Available

Derivatized

DerivativeValueReference
Umbelliferone,1TMS,#11871.1514https://arxiv.org/abs/1905.12712
Umbelliferone,1TBDMS,#12132.5017https://arxiv.org/abs/1905.12712
Spectra

GC-MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03gi-9700000000-61b0cf13acd34fc7ef622017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-6900000000-dedc215fac13e97ee7692017-09-12View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03gi-9700000000-61b0cf13acd34fc7ef622018-05-18View Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-6900000000-dedc215fac13e97ee7692018-05-18View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02ai-0900000000-0624e9db800b4bf28fbb2017-07-27View Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-5940000000-389049e95813b961c56b2017-10-06View Spectrum
MSMass Spectrum (Electron Ionization)splash10-03e9-6900000000-0be270410ca1ed2de5312015-03-01View Spectrum

LC-MS/MS

Spectrum TypeDescriptionSplash KeyDeposition DateView
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0kmi-0920000000-2cd49ad40f2f08fee3ab2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0kmi-0920000000-2cd49ad40f2f08fee3ab2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0kmi-0920000000-2cd49ad40f2f08fee3ab2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0kmi-0920000000-2cd49ad40f2f08fee3ab2017-08-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0900000000-1c416a1d92a90a4424ff2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-03e9-0900000000-ceab22ae6ab894db98ee2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0900000000-9f3b0c63320b7a16d26f2017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-03di-0900000000-26b715dfa168a96a7f792017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0900000000-1349a86992b0b49b6c462017-09-12View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-03di-0900000000-a4062ec204d8a8bbf5572017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-03e9-0900000000-1243c09e68f71ea9dbc92017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-a0363e87c8dfdf5684e12017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-ef5555622fcf5901817a2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01q9-0900000000-0a23407c9d3acb3a96462017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0089-3900000000-b06b1adaffe70bae68292017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0900000000-18c4c14a01ab29d764d22017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0900000000-f9da00f6ddcb61b14a8c2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-03e9-0900000000-ceab22ae6ab894db98ee2017-09-14View Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0900000000-9f3b0c63320b7a16d26f2017-09-14View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-bafe152884074efd6ae42016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-ba2ab3999b706f4fba942016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-3900000000-94ba274c0fe68fcd55452016-08-01View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-a37e719efb7afa07f7072016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-a5780fb402be64e17c802016-08-03View Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3900000000-f5ab2c793215524c01ec2016-08-03View Spectrum

NMR

Spectrum TypeDescriptionDeposition DateView
1D NMR13C NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 100 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 200 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 300 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 400 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 500 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 600 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 700 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 800 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 900 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR13C NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
1D NMR1H NMR Spectrum (1D, 1000 MHz, D2O, predicted)2021-09-16View Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot Available
Normal
      Not Available
details
UrineDetected and Quantified0.13 umol/mmol creatinineAdult (>18 years old)BothNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound ID641
FooDB IDFDB001094
KNApSAcK IDC00002503
Chemspider ID4444774
KEGG Compound IDC09315
BioCyc IDCPD-8186
BiGG IDNot Available
Wikipedia LinkUmbelliferone
METLIN IDNot Available
PubChem Compound5281426
PDB ID07L
ChEBI ID27510
Food Biomarker OntologyNot Available
VMH IDHCOUMARIN
MarkerDB IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Gok E: Investigation of binding properties of umbelliferone (7hydroxycoumarin) to lysozyme. J Fluoresc. 2013 Mar;23(2):333-8. doi: 10.1007/s10895-012-1151-0. Epub 2012 Dec 8. [PubMed:23224618 ]
  2. (). 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
Umbelliferone → 3,4,5-trihydroxy-6-[(2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylic aciddetails