Record Information
Version1.0
Creation date2010-04-08 22:04:50 UTC
Update date2018-05-28 22:37:28 UTC
Primary IDFDB001094
Secondary Accession Numbers
  • FDB012649
Chemical Information
FooDB NameUmbelliferone
DescriptionOccurs widely in plants including Angelica subspecies Phytoalexin of infected sweet potato. Umbelliferone is found in many foods, some of which are macadamia nut, silver linden, quince, and capers.
CAS Number93-35-6
Structure
Thumb
Synonyms
SynonymSource
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
β-umbelliferonebiospider
2H-1-Benzopyran-2-one, 7-hydroxy-biospider
7-hydroxycoumarin sulfatebiospider
7-hydroxycoumarin, 14C-labeledbiospider
Beta-umbelliferonebiospider
Coumarin, 7-hydroxy-biospider
Umbelliferonedb_source
β-umbelliferoneGenerator
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
Chemical FormulaC9H6O3
IUPAC name7-hydroxy-2H-chromen-2-one
InChI IdentifierInChI=1S/C9H6O3/c10-7-3-1-6-2-4-9(11)12-8(6)5-7/h1-5,10H
InChI KeyORHBXUUXSCNDEV-UHFFFAOYSA-N
Isomeric SMILESOC1=CC2=C(C=C1)C=CC(=O)O2
Average Molecular Weight162.144
Monoisotopic Molecular Weight162.031694053
Classification
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
OntologyShould have ontology for this compound
Physico-Chemical Properties - Experimental
Physico-Chemical Properties - Experimental
PropertyValueReference
Physical stateNot Available
Physical DescriptionNot Available
Mass CompositionC 66.67%; H 3.73%; O 29.60%DFC
Melting PointMp 230-232° (223-224°, 227-228°)DFC
Boiling PointNot Available
Experimental Water SolubilityNot Available
Experimental logPNot Available
Experimental pKapKa1 7.7DFC
Isoelectric pointNot Available
ChargeNot Available
Optical RotationNot Available
Spectroscopic UV Data[base] lmax 377 () (NaOH) (Berdy)DFC
DensityNot Available
Refractive IndexNot Available
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
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
ChemSpider ID4444774
ChEMBL IDCHEMBL51628
KEGG Compound IDC09315
Pubchem Compound ID5281426
Pubchem Substance IDNot Available
ChEBI ID27510
Phenol-Explorer ID641
DrugBank IDNot Available
HMDB IDHMDB29865
CRC / DFC (Dictionary of Food Compounds) IDBSX04-T:BSX04-T
EAFUS IDNot Available
Dr. Duke IDUMBELLIFERONE
BIGG IDNot Available
KNApSAcK IDC00002503
HET ID07L
Flavornet IDNot Available
GoodScent IDNot Available
SuperScent IDNot Available
Wikipedia IDNot Available
Phenol-Explorer Metabolite IDNot Available
Duplicate IDSNot Available
Old DFC IDSNot Available
Associated Foods
FoodContent Range AverageReference
FoodReference
Biological Effects and Interactions
Health Effects / Bioactivities
DescriptorIDDefinitionReference
aldose reductase inhibitor48550 An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD(+) or NADP(+) acceptor) inhibitor that interferes with the action of aldehyde reductase (EC 1.1.1.21).DUKE
allelochemicDUKE
anti bacterial33282 A substance that kills or slows the growth of bacteria.DUKE
anti edemicDUKE
anti histaminic37956 Histamine antagonists are the drugs that bind to but do not activate histamine receptors, thereby blocking the actions of histamine or histamine agonists.DUKE
anti inflammatory35472 A substance that reduces or suppresses inflammation.DUKE
anti mitoticDUKE
anti mutagenicDUKE
anti prostaglandin49020 A chemical substance which inhibits the function of the endocrine glands, the biosynthesis of their secreted hormones, or the action of hormones upon their specific sites.DUKE
anti septic33281 A substance that kills or slows the growth of microorganisms, including bacteria, viruses, fungi and protozoans.DUKE
anti spasmodic52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
anti staphylococcic33282 A substance that kills or slows the growth of bacteria.DUKE
cancer preventive35610 A substance that inhibits or prevents the proliferation of neoplasms.DUKE
candidicideDUKE
cholereticDUKE
fungicide24127 A substance used to destroy fungal pests.DUKE
lipoxygenase inhibitor35856 A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.DUKE
perfumery48318 A substance, extract, or preparation for diffusing or imparting an agreeable or attractive smell.DUKE
pesticide25944 Strictly, a substance intended to kill pests. In common usage, any substance used for controlling, preventing, or destroying animal, microbiological or plant pests.DUKE
photoactiveDUKE
sunscreen52217 Any substance introduced into a living organism with therapeutic or diagnostic purpose.DUKE
xanthine oxidase inhibitor35634 An EC 1.17.3.* (oxidoreductase acting on CH or CH2 with oxygen as acceptor) inhibitor that interferes with the action of xanthine oxidase (EC 1.17.3.2).DUKE
EnzymesNot Available
PathwaysNot Available
MetabolismNot Available
BiosynthesisNot Available
Organoleptic Properties
FlavoursNot Available
Files
MSDSNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
Content Reference— Duke, James. 'Dr. Duke's Phytochemical and Ethnobotanical Databases. United States Department of Agriculture.' Agricultural Research Service, Accessed April 27 (2004).
— Shinbo, Y., et al. 'KNApSAcK: a comprehensive species-metabolite relationship database.' Plant Metabolomics. Springer Berlin Heidelberg, 2006. 165-181.
— Rothwell JA, Pérez-Jiménez J, Neveu V, Medina-Ramon A, M'Hiri N, Garcia Lobato P, Manach C, Knox K, Eisner R, Wishart D, Scalbert A. (2013) Phenol-Explorer 3.0: a major update of the Phenol-Explorer database to incorporate data on the effects of food processing on polyphenol content. Database, 10.1093/database/bat070.