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Record Information
Version4.0
StatusDetected and Quantified
Creation Date2012-09-11 17:33:07 UTC
Update Date2017-12-07 02:59:56 UTC
HMDB IDHMDB0029865
Secondary Accession Numbers
  • HMDB29865
Metabolite Identification
Common NameUmbelliferone
DescriptionUmbelliferone is found in anise. Umbelliferone occurs widely in plants including Angelica species Phytoalexin of infected sweet potat
Structure
Thumb
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
DescriptionThis compound belongs to the class of chemical entities known as 7-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to the C7 position the coumarin skeleton.
KingdomChemical entities
Super ClassOrganic compounds
ClassPhenylpropanoids and polyketides
Sub ClassCoumarins and derivatives
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

Biological Location:

  Subcellular:

  Biofluid and excreta:

  Cell and elements:

Source:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting Point230 - 232 °CNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03gi-9700000000-61b0cf13acd34fc7ef62View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-03di-6900000000-dedc215fac13e97ee769View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-02ai-0900000000-0624e9db800b4bf28fbbView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-00dl-5940000000-389049e95813b961c56bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0kmi-0920000000-2cd49ad40f2f08fee3abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0kmi-0920000000-2cd49ad40f2f08fee3abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-0kmi-0920000000-2cd49ad40f2f08fee3abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0kmi-0920000000-2cd49ad40f2f08fee3abView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0900000000-1c416a1d92a90a4424ffView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-03e9-0900000000-ceab22ae6ab894db98eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 30V, Negativesplash10-001i-0900000000-9f3b0c63320b7a16d26fView in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-03di-0900000000-26b715dfa168a96a7f79View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-03di-0900000000-1349a86992b0b49b6c46View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Positivesplash10-03di-0900000000-a4062ec204d8a8bbf557View in MoNA
LC-MS/MSLC-MS/MS Spectrum - DI-ESI-qTof , Negativesplash10-03e9-0900000000-1243c09e68f71ea9dbc9View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-a0363e87c8dfdf5684e1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-03di-0900000000-ef5555622fcf5901817aView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-01q9-0900000000-0a23407c9d3acb3a9646View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , negativesplash10-0089-3900000000-b06b1adaffe70bae6829View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0900000000-18c4c14a01ab29d764d2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Linear Ion Trap , negativesplash10-03di-0900000000-f9da00f6ddcb61b14a8cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-03e9-0900000000-ceab22ae6ab894db98eeView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-TOF , negativesplash10-001i-0900000000-9f3b0c63320b7a16d26fView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-bafe152884074efd6ae4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-0900000000-ba2ab3999b706f4fba94View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-014j-3900000000-94ba274c0fe68fcd5545View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0900000000-a37e719efb7afa07f707View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0900000000-a5780fb402be64e17c80View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-014i-3900000000-f5ab2c793215524c01ecView in MoNA
MSMass Spectrum (Electron Ionization)splash10-03e9-6900000000-0be270410ca1ed2de531View in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Extracellular
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot Available
Normal
    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
    DrugBank Metabolite IDNot Available
    Phenol Explorer Compound ID641
    Phenol Explorer Metabolite IDNot Available
    FoodDB IDFDB001094
    KNApSAcK IDC00002503
    Chemspider ID4444774
    KEGG Compound IDC09315
    BioCyc IDNot Available
    BiGG IDNot Available
    Wikipedia LinkUmbelliferone
    METLIN IDNot Available
    PubChem Compound5281426
    PDB ID07L
    ChEBI ID27510
    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