Cannabis Compound Database: Showing Compound Card for Taxifolin (CDB006368)

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Record Information

Version

1.0

Created at

2020-11-03 16:25:48 UTC

Updated at

2022-12-13 19:31:28 UTC

CannabisDB ID

CDB006368

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Taxifolin

Description

Taxifolin, also known as dihydroquercetin, 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. Taxifolin is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review very few articles have been published on Taxifolin.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+)-Dihydroquercetin	ChEBI
(2R,3R)-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4H-1-benzopyran-4-one	ChEBI
(2R,3R)-Dihydroquercetin	ChEBI
(2R-trans)-2-(3,4-Dihydroxyphenyl)-2,3-dihydro-3,5,7-trihydroxy-4-benzopyrone	ChEBI
Dihydroquercetin	ChEBI
trans-Dihydroquercetin	ChEBI
(+)-Taxifolin	Kegg
2,3-trans-Dihydroquercetin	ChEBI
Taxifolin	ChEBI
(+)-(2R,3R)-Dihydroquercetin	PhytoBank
(+)-trans-Taxifolin	PhytoBank
(2R,3R)-(+)-Taxifolin	PhytoBank
(2R,3R)-3,3',4',5,7-Pentahydroxyflavanone	PhytoBank
(2R,3R)-3,3’,4’,5,7-Pentahydroxyflavanone	PhytoBank
2,3-Dihydroquercetin	PhytoBank
3,5,7,3',4'-Pentahydroxyflavanone	PhytoBank
3,5,7,3’,4’-Pentahydroxyflavanone	PhytoBank
Diquertin	PhytoBank
Distylin	PhytoBank
Flamena	PhytoBank
Flamena D	PhytoBank
Jikuberuchin	PhytoBank
Lariksin	PhytoBank
Lavitol	PhytoBank
Taxifoliol	PhytoBank

Chemical Formula

C₁₅H₁₂O₇

Average Molecular Weight

304.2516

Monoisotopic Molecular Weight

304.058302738

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 Number

Not 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 Key

CXQWRCVTCMQVQX-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.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Flavanonols

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 Framework

Aromatic heteropolycyclic compounds

External Descriptors

taxifolin (CHEBI:17948 )
Dihyroflavonols (C01617 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	1.07	ALOGPS
logP	1.82	ChemAxon
logS	-2.4	ALOGPS
pKa (Strongest Acidic)	7.74	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	127.45 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.61 m³·mol⁻¹	ChemAxon
Polarizability	29.03 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Not Available

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - ESI-TOF 25V, Negative	splash10-00fr-0591000000-8c2bb267dbaff0ec8425	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0fk9-0393000000-2ad9cdbeaebe4832addf	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0udi-0019000000-f4c2db21ffbf7fdec0ec	2017-08-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 25V, Negative	splash10-00fr-0591000000-8c2bb267dbaff0ec8425	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF 20V, Negative	splash10-0fk9-0393000000-2ad9cdbeaebe4832addf	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - ESI-TOF , Negative	splash10-0udi-0019000000-f4c2db21ffbf7fdec0ec	2017-09-12	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Positive	splash10-0pc1-0980000000-2d1ecd15f61d12518b21	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - DI-ESI-qTof , Negative	splash10-004r-0960000000-22428e71371e23f8c0f1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-0a4r-0965000000-d0ca2227f5b5c9adb509	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-000i-0190000000-5cfd8e48c0ba0adace9c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , negative	splash10-000i-0190000000-4e9899457ae22ca1e3a8	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-00fr-0591000000-8c2bb267dbaff0ec8425	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-TOF , negative	splash10-0fk9-0393000000-2ad9cdbeaebe4832addf	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - Linear Ion Trap , positive	splash10-004i-0090000000-1c45a54959ecd51d8615	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0a4r-0965000000-d0ca2227f5b5c9adb509	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-0ul1-0930000000-805f5b6770fe1b1ed799	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT 21V, positive	splash10-052r-0290000000-107edeec139715941215	2020-07-24	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-IT 21V, positive	splash10-0k9i-0490000000-54689ad702b3a9efd331	2020-07-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0229000000-ca2358a4a03140a28800	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0k9i-0932000000-8fe616c50e11538a79d2	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f79-3900000000-055fc061b8b4ca3c7e7d	2016-06-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0319000000-14f9f888c64a72109519	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0923000000-2e407916474c28202553	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-4910000000-da486b0c8e7b8f7c2a40	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0009000000-af408fd7a67d4a98dd0c	2021-10-21	View Spectrum

NMR

Not Available

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Cannabis Cultivar	Status	Value	Reference	Details
Alien Dawg	Detected and Quantified	0.0167 mg/g dry wt	David S. Wishart,...	details
Gabriola	Detected and Quantified	0.0166 mg/g dry wt	David S. Wishart,...	details
Island Honey	Detected and Quantified	0.017 mg/g dry wt	David S. Wishart,...	details
Quadra	Detected and Quantified	0.0166 mg/g dry wt	David S. Wishart,...	details
Sensi Star	Detected and Quantified	0.0163 mg/g dry wt	David S. Wishart,...	details
Tangerine Dream	Detected and Quantified	0.0175 mg/g dry wt	David S. Wishart,...	details