Taxifolin

Identification

Name
Taxifolin
Accession Number
DB02224  (EXPT01185)
Type
Small Molecule
Groups
Experimental
Description
Not Available
Structure
Thumb
Synonyms
  • (+)-(2R,3R)-dihydroquercetin
  • (+)-dihydroquercetin
  • (+)-taxifolin
  • (2R,3R)-(+)-taxifolin
  • (2R,3R)-3,3',4',5,7-pentahydroxyflavanone
  • (2R,3R)-dihydroquercetin
  • Dihydroquercetin
Categories
UNII
9SOB9E3987
CAS number
480-18-2
Weight
Average: 304.2516
Monoisotopic: 304.058302738
Chemical Formula
C15H12O7
InChI Key
CXQWRCVTCMQVQX-LSDHHAIUSA-N
InChI
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
IUPAC Name
(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-one
SMILES
O[C@@H]1[C@H](OC2=CC(O)=CC(O)=C2C1=O)C1=CC=C(O)C(O)=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
Not Available
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism
Not Available
Route of elimination
Not Available
Half life
Not Available
Clearance
Not Available
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
(R)-warfarinThe risk or severity of bleeding and hemorrhage can be increased when Taxifolin is combined with (R)-warfarin.
(S)-WarfarinThe risk or severity of bleeding and hemorrhage can be increased when Taxifolin is combined with (S)-Warfarin.
1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic AcidThe risk or severity of renal failure, hyperkalemia, and hypertension can be increased when Taxifolin is combined with 1-(3-Mercapto-2-Methyl-Propionyl)-Pyrrolidine-2-Carboxylic Acid.
4-hydroxycoumarinThe risk or severity of bleeding and hemorrhage can be increased when Taxifolin is combined with 4-hydroxycoumarin.
AbciximabThe risk or severity of bleeding and hemorrhage can be increased when Taxifolin is combined with Abciximab.
AcebutololTaxifolin may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Aceclofenac is combined with Taxifolin.
AcemetacinThe risk or severity of adverse effects can be increased when Acemetacin is combined with Taxifolin.
AcenocoumarolThe risk or severity of bleeding and hemorrhage can be increased when Taxifolin is combined with Acenocoumarol.
AcetohexamideThe protein binding of Acetohexamide can be decreased when combined with Taxifolin.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Compound
C01617
PubChem Compound
439533
PubChem Substance
46508033
ChemSpider
388626
BindingDB
212435
ChEBI
17948
ChEMBL
CHEMBL66
HET
DQH
Wikipedia
Taxifolin
PDB Entries
1gp5 / 2c29 / 3tvq

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
logP0.95PERRISSOUD,D & TESTA,B (1986)
Predicted Properties
PropertyValueSource
Water Solubility1.16 mg/mLALOGPS
logP1.07ALOGPS
logP1.82ChemAxon
logS-2.4ALOGPS
pKa (Strongest Acidic)7.8ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area127.45 Å2ChemAxon
Rotatable Bond Count1ChemAxon
Refractivity74.61 m3·mol-1ChemAxon
Polarizability29.03 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.965
Blood Brain Barrier-0.5711
Caco-2 permeable-0.8957
P-glycoprotein substrateSubstrate0.5629
P-glycoprotein inhibitor INon-inhibitor0.9297
P-glycoprotein inhibitor IINon-inhibitor0.8382
Renal organic cation transporterNon-inhibitor0.931
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateNon-substrate0.653
CYP450 1A2 substrateInhibitor0.9106
CYP450 2C9 inhibitorNon-inhibitor0.5823
CYP450 2D6 inhibitorNon-inhibitor0.9287
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorInhibitor0.6951
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.5822
Ames testNon AMES toxic0.722
CarcinogenicityNon-carcinogens0.945
BiodegradationNot ready biodegradable0.8672
Rat acute toxicity3.0200 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9781
hERG inhibition (predictor II)Non-inhibitor0.8161
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 25V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 25V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF 20V, NegativeLC-MS/MSNot Available
MS/MS Spectrum - ESI-TOF , NegativeLC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - DI-ESI-qTof , NegativeLC-MS/MSNot Available
LC-MS/MS Spectrum - LC-ESI-qTof , PositiveLC-MS/MSNot Available
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-000i-0190000000-5cfd8e48c0ba0adace9c
MS/MS Spectrum - Linear Ion Trap , negativeLC-MS/MSsplash10-000i-0190000000-4e9899457ae22ca1e3a8
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-00fr-0591000000-8c2bb267dbaff0ec8425
LC-MS/MS Spectrum - LC-ESI-TOF , negativeLC-MS/MSsplash10-0fk9-0393000000-2ad9cdbeaebe4832addf
MS/MS Spectrum - Linear Ion Trap , positiveLC-MS/MSsplash10-004i-0090000000-1c45a54959ecd51d8615
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0a4r-0965000000-d0ca2227f5b5c9adb509
MS/MS Spectrum - , positiveLC-MS/MSsplash10-0ul1-0930000000-805f5b6770fe1b1ed799

Taxonomy

Description
This compound belongs to the class of organic compounds known as flavanonols. These 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.
Kingdom
Organic compounds
Super Class
Phenylpropanoids and polyketides
Class
Flavonoids
Sub Class
Flavans
Direct Parent
Flavanonols
Alternative Parents
3'-hydroxyflavonoids / 3-hydroxyflavonoids / 4'-hydroxyflavonoids / 5-hydroxyflavonoids / 7-hydroxyflavonoids / Chromones / Catechols / Aryl alkyl ketones / 1-hydroxy-2-unsubstituted benzenoids / 1-hydroxy-4-unsubstituted benzenoids
show 8 more
Substituents
Hydroxyflavonoid / Flavanonol / 3'-hydroxyflavonoid / 3-hydroxyflavonoid / 4'-hydroxyflavonoid / 5-hydroxyflavonoid / 7-hydroxyflavonoid / Chromone / Benzopyran / 1-benzopyran
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
taxifolin (CHEBI:17948) / Dihyroflavonols (C01617)

Drug created on June 13, 2005 07:24 / Updated on November 02, 2018 05:14