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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2021-09-24 05:51:44 UTC
Update Date2022-09-22 18:34:59 UTC
HMDB IDHMDB0303943
Secondary Accession NumbersNone
Metabolite Identification
Common Name(+)-taxifolin
DescriptionTaxifolin, also known as dihydroquercetin or (+)-taxifolin, is a member of the class of compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively. Taxifolin is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Taxifolin can be found in a number of food items such as sweet rowanberry, arrowroot, evening primrose, and walnut, which makes taxifolin a potential biomarker for the consumption of these food products. Taxifolin is a flavanonol, a type of flavonoid .
Structure
Thumb
Synonyms
ValueSource
(+)-DihydroquercetinChEBI
(2R,3R)-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-oneChEBI
(2R,3R)-DihydroquercetinChEBI
(2R-trans)-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4-benzopyroneChEBI
DihydroquercetinChEBI
trans-DihydroquercetinChEBI
(+)-TaxifolinKegg
2,3-trans-DihydroquercetinChEBI
TaxifolinChEBI
(+)-(2R,3R)-DihydroquercetinPhytoBank
(+)-trans-TaxifolinPhytoBank
(2R,3R)-(+)-TaxifolinPhytoBank
(2R,3R)-3,3',4',5,7-PentahydroxyflavanonePhytoBank
(2R,3R)-3,3’,4’,5,7-PentahydroxyflavanonePhytoBank
2,3-DihydroquercetinPhytoBank
3,5,7,3',4'-PentahydroxyflavanonePhytoBank
3,5,7,3’,4’-PentahydroxyflavanonePhytoBank
DiquertinPhytoBank
DistylinPhytoBank
FlamenaPhytoBank
Flamena DPhytoBank
JikuberuchinPhytoBank
LariksinPhytoBank
LavitolPhytoBank
TaxifoliolPhytoBank
Chemical FormulaC15H12O7
Average Molecular Weight304.2516
Monoisotopic Molecular Weight304.058302738
IUPAC Name(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-one
Traditional Name(+)-taxifolin
CAS Registry NumberNot Available
SMILES
O[C@@H]1[C@H](OC2=CC(O)=CC(O)=C2C1=O)C1=CC(O)=C(O)C=C1
InChI Identifier
InChI=1S/C15H12O7/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/h1-5,14-19,21H/t14-,15+/m0/s1
InChI KeyCXQWRCVTCMQVQX-LSDHHAIUSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as flavanonols. Flavanonols are compounds containing a flavan-3-one moiety, with a structure characterized by a 2-phenyl-3,4-dihydro-2H-1-benzopyran bearing a hydroxyl group and a ketone at the carbon C2 and C3, respectively.
KingdomOrganic compounds
Super ClassPhenylpropanoids and polyketides
ClassFlavonoids
Sub ClassFlavans
Direct ParentFlavanonols
Alternative Parents
Substituents
  • Hydroxyflavonoid
  • Flavanonol
  • 3'-hydroxyflavonoid
  • 3-hydroxyflavonoid
  • 4'-hydroxyflavonoid
  • 5-hydroxyflavonoid
  • 7-hydroxyflavonoid
  • Chromone
  • Benzopyran
  • 1-benzopyran
  • Chromane
  • Catechol
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol
  • 1-hydroxy-4-unsubstituted benzenoid
  • 1-hydroxy-2-unsubstituted benzenoid
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Benzenoid
  • Vinylogous acid
  • Secondary alcohol
  • Ketone
  • Polyol
  • Organoheterocyclic compound
  • Oxacycle
  • Ether
  • Organooxygen compound
  • Organic oxide
  • Organic oxygen compound
  • Alcohol
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological locationSource
Process
Role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP1.07ALOGPS
logP1.82ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)7.74ChemAxon
pKa (Strongest Basic)-4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.45 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.61 m³·mol⁻¹ChemAxon
Polarizability29.03 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+170.28432859911
AllCCS[M+H-H2O]+166.67432859911
AllCCS[M+Na]+174.59732859911
AllCCS[M+NH4]+173.63432859911
AllCCS[M-H]-167.97932859911
AllCCS[M+Na-2H]-167.40132859911
AllCCS[M+HCOO]-166.932859911
DeepCCS[M+H]+170.58930932474
DeepCCS[M-H]-168.23130932474
DeepCCS[M-2H]-202.30430932474
DeepCCS[M+Na]+177.32130932474

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin ESI-TOF 25V, Negative-QTOFsplash10-00fr-0591000000-8c2bb267dbaff0ec84252017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin ESI-TOF 20V, Negative-QTOFsplash10-0fk9-0393000000-2ad9cdbeaebe4832addf2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin ESI-TOF , Negative-QTOFsplash10-0udi-0019000000-f4c2db21ffbf7fdec0ec2017-08-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin ESI-TOF 25V, Negative-QTOFsplash10-00fr-0591000000-8c2bb267dbaff0ec84252017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin ESI-TOF 20V, Negative-QTOFsplash10-0fk9-0393000000-2ad9cdbeaebe4832addf2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin ESI-TOF , Negative-QTOFsplash10-0udi-0019000000-f4c2db21ffbf7fdec0ec2017-09-12HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin DI-ESI-qTof , Positive-QTOFsplash10-0pc1-0980000000-2d1ecd15f61d12518b212017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin DI-ESI-qTof , Negative-QTOFsplash10-004r-0960000000-22428e71371e23f8c0f12017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin LC-ESI-qTof , Positive-QTOFsplash10-0a4r-0965000000-d0ca2227f5b5c9adb5092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin Linear Ion Trap , negative-QTOFsplash10-000i-0190000000-5cfd8e48c0ba0adace9c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin Linear Ion Trap , negative-QTOFsplash10-000i-0190000000-4e9899457ae22ca1e3a82017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin LC-ESI-TOF , negative-QTOFsplash10-00fr-0591000000-8c2bb267dbaff0ec84252017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin LC-ESI-TOF , negative-QTOFsplash10-0fk9-0393000000-2ad9cdbeaebe4832addf2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin Linear Ion Trap , positive-QTOFsplash10-004i-0090000000-1c45a54959ecd51d86152017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin , positive-QTOFsplash10-0a4r-0965000000-d0ca2227f5b5c9adb5092017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin , positive-QTOFsplash10-0ul1-0930000000-805f5b6770fe1b1ed7992017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin LC-ESI-QFT 21V, positive-QTOFsplash10-052r-0290000000-107edeec1397159412152020-07-24HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - (+)-taxifolin LC-ESI-IT 21V, positive-QTOFsplash10-0k9i-0490000000-54689ad702b3a9efd3312020-07-24HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-taxifolin 10V, Positive-QTOFsplash10-0a4i-0229000000-ca2358a4a03140a288002016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-taxifolin 20V, Positive-QTOFsplash10-0k9i-0932000000-8fe616c50e11538a79d22016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-taxifolin 40V, Positive-QTOFsplash10-0f79-3900000000-055fc061b8b4ca3c7e7d2016-06-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-taxifolin 10V, Negative-QTOFsplash10-0udi-0319000000-14f9f888c64a721095192016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-taxifolin 20V, Negative-QTOFsplash10-0udi-0923000000-2e407916474c282025532016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-taxifolin 40V, Negative-QTOFsplash10-0a4i-4910000000-da486b0c8e7b8f7c2a402016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - (+)-taxifolin 10V, Positive-QTOFsplash10-0a4i-0009000000-af408fd7a67d4a98dd0c2021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
UrineDetected but not QuantifiedNot QuantifiedNot SpecifiedNot SpecifiedNormal details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB02224
Phenol Explorer Compound IDNot Available
FooDB IDFDB030075
KNApSAcK IDC00000677
Chemspider ID388626
KEGG Compound IDC01617
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTaxifolin
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID17948
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDrw1504391
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available