Showing metabocard for Quercetin (BMDB0005794)

IdentificationTaxonomyPhysical propertiesPathwaysSpectraConcentrationsLinksReferencesenzymes (1) Show 1 proteinXML
Record Information
Version1.0
Creation Date2016-09-30 23:18:35 UTC
Update Date2020-04-22 15:16:20 UTC
BMDB IDBMDB0005794
Secondary Accession Numbers
  • BMDB05794
Metabolite Identification
Common NameQuercetin
DescriptionQuercetin, also known as sophoretin or xanthaurine, belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position. Thus, quercetin is considered to be a flavonoid. Quercetin exists in all living species, ranging from bacteria to plants to humans. Based on a literature review a significant number of articles have been published on Quercetin.
Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D Structure
Synonyms
ValueSource
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-1-benzopyran-4-oneChEBI
3,3',4',5,7-PentahydroxyflavoneChEBI
3,5,7,3',4'-PentahydroxyflavoneChEBI
SophoretinChEBI
XanthaurineChEBI
3,3',4,5,7-PentahydroxyflavoneKegg
DikvertinMeSH
2-(3,4-Dihydroxy-phenyl)-3,5,7-trihydroxy-chromen-4-oneHMDB
3',4',5,7-Tetrahydroxyflavan-3-olHMDB
3',4',5,7-Tetrahydroxyflavon-3-olHMDB
3,4',5,5',7-Pentahydroxy-flavoneHMDB
3,5,7-Trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-ONHMDB
Flavin meletinHMDB
MeletinHMDB
Quercetin dihydrateHMDB
QuercetolHMDB
QuertinHMDB
2-(3,4-Dihydroxyphenyl)-3,5,7-trihydroxy-4H-benzopyran-4-onePhytoBank
3,3’,4’,5,7-PentahydroxyflavonePhytoBank
3,5,7,3’,4’-PentahydroxyflavonePhytoBank
3,5,7-Trihydroxy-2-(3,4-dihydroxyphenyl)-4H-chromen-4-onePhytoBank
3'-HydroxykaempferolPhytoBank
3’-HydroxykaempferolPhytoBank
QuercetinePhytoBank
QuertinePhytoBank
Chemical FormulaC15H10O7
Average Molecular Weight302.2357
Monoisotopic Molecular Weight302.042652674
IUPAC Name2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-4H-chromen-4-one
Traditional Namequercetin
CAS Registry Number117-39-5
SMILES
OC1=CC2=C(C(O)=C1)C(=O)C(O)=C(O2)C1=CC=C(O)C(O)=C1
InChI Identifier
InChI=1S/C15H10O7/c16-7-4-10(19)12-11(5-7)22-15(14(21)13(12)20)6-1-2-8(17)9(18)3-6/h1-5,16-19,21H
InChI KeyREFJWTPEDVJJIY-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as flavonols. Flavonols are compounds that contain a flavone (2-phenyl-1-benzopyran-4-one) backbone carrying a hydroxyl group at the 3-position.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavones
Direct ParentFlavonols
Alternative Parents
Substituents
  • 3-hydroxyflavone
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Catechol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Phenol
  • Pyranone
  • Benzenoid
  • Monocyclic benzene moiety
  • Pyran
  • Heteroaromatic compound
  • Vinylogous acid
  • Oxacycle
  • Organoheterocyclic compound
  • Polyol
  • Organic oxide
  • Organic oxygen compound
  • Hydrocarbon derivative
  • Organooxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Exogenous
BiofunctionNot Available
ApplicationNot Available
Cellular locations
  • Cell membrane
  • Membrane
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point316 - 318 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.06 mg/mL at 16 °CNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP1.81ALOGPS
logP2.16ChemAxon
logS-3.1ALOGPS
pKa (Strongest Acidic)6.38ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.45 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity76.86 m³·mol⁻¹ChemAxon
Polarizability28.54 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
GC-MSGC-MS Spectrum - GC-MS (5 TMS)splash10-0bt9-2611390000-f8e98c928a7ed82acda4View in MoNA
GC-MSGC-MS Spectrum - GC-MS (Non-derivatized)splash10-0bt9-2611390000-f8e98c928a7ed82acda4View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0079-0591000000-2a146657da898ec9322eView in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (5 TMS) - 70eV, Positivesplash10-00l2-2093078000-1de46637305246feffd2View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableView in JSpectraViewer
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 10V, Positive (Annotated)splash10-0udi-0009000000-d4689b76f41c73487399View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 25V, Positive (Annotated)splash10-0udi-0967000000-613e61ec0c69ed0ee630View in MoNA
LC-MS/MSLC-MS/MS Spectrum - Quattro_QQQ 40V, Positive (Annotated)splash10-0uy0-5910000000-ee816015eec26c8621b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) 5V, Positivesplash10-0udi-0009000000-ec1cab852ed9f9f78fa4View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-1907000000-6f36df2733dadae380c2View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0309000000-976a99c106ceca16d73bView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0pi0-1900000000-b2e286366d41e47dd8fcView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-0209000000-e891863ec110aeb660b0View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0940000000-aa52db00c1defe3ccf75View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0219000000-5ef285c4b6bfd220b8b1View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Positivesplash10-0udi-0219000000-547c83bb70e7da007d6cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF (UPLC Q-Tof Premier, Waters) , Negativesplash10-0udi-1907000000-a59602c09f66e9656068View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Positivesplash10-0udi-0009000000-4416f39adf6c9b919bfaView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0udi-0019000000-eb14ec62fc2fb2f1da88View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-ITTOF (LCMS-IT-TOF) , Negativesplash10-0ufr-0910000000-0730bca525c17aac75c5View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-004i-0030290000-06238e4a98a4daad3265View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF , Negativesplash10-0udi-0039008002-9df3edfb34deb15f8474View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 10V, Negativesplash10-0udi-0039008002-9df3edfb34deb15f8474View in MoNA
LC-MS/MSLC-MS/MS Spectrum - ESI-TOF 20V, Negativesplash10-0uka-0193000000-3325ca1a080730a9c0bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0019000000-ee8570ac70818e8939bbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0279000000-71b5db7ef8322cc8b9e9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zg0-7960000000-7edbb229853a642749acView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-21580b9d8394d2eea3a5View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0239000000-b77fcb9c0ce11dc515bfView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0apr-5940000000-0590bdee504c5ed6ba36View in MoNA
1D NMR1H NMR Spectrum (1D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, experimental)Not AvailableView in JSpectraViewer
1D NMR1H NMR Spectrum (1D, 600 MHz, DMSO, experimental)Not AvailableView in JSpectraViewer
2D NMR[1H, 13C]-HSQC NMR Spectrum (2D, 600 MHz, 100%_DMSO, experimental)Not AvailableView in JSpectraViewer
Biological Properties
Cellular Locations
  • Cell membrane
  • Membrane
Biospecimen LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
HMDB IDHMDB0005794
DrugBank IDDB04216
Phenol Explorer Compound ID291
FooDB IDFDB011904
KNApSAcK IDC00004631
Chemspider ID4444051
KEGG Compound IDC00389
BioCyc IDCPD-520
BiGG IDNot Available
Wikipedia LinkQuercetin
METLIN IDNot Available
PubChem Compound5280343
PDB IDQUE
ChEBI ID16243
References
Synthesis ReferenceKrewson, Charles F. Colloidal flavonols. (1953), US 2637725 19530505 CAN 47:42700 AN 1953:42700
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Dehydrogenase/reductase SDR family member 4
General function:
Lipid transport and metabolism
Specific function:
Reduces all-trans-retinal and 9-cis retinal. Can also catalyze the oxidation of all-trans-retinol with NADP as co-factor, but with much lower efficiency. Reduces alkyl phenyl ketones and alpha-dicarbonyl compounds with aromatic rings, such as pyrimidine-4-aldehyde, 3-benzoylpyridine, 4-benzoylpyridine, menadione and 4-hexanoylpyridine. Has no activity towards aliphatic aldehydes and ketones (By similarity).
Gene Name:
DHRS4
Uniprot ID:
Q8SPU8
Molecular weight:
29440.0