NP-MRD: Showing NP-Card for Taxifolin (NP0332353)

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Record Information

Version

1.0

Created at

2024-01-10 00:11:08 UTC

Updated at

2024-09-03 04:18:55 UTC

NP-MRD ID

NP0332353

DOI

https://doi.org/10.57994/1566

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Taxifolin

Description

Not Available

Structure

MOL SDF PDB SMILES InChI


  Mrv1652309272007472D          

 22 24  0  0  0  0            999 V2000
 9999.6614 9997.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.0876 9998.5361    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10001.805210002.2527    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.232110001.4279    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2367 9997.7072    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9996.807810000.1927    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10002.517710001.0171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.803210001.4295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.088710001.0170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.088610000.1920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.8031 9999.7795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.517710000.1921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.662310000.1884    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9478 9999.7759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9478 9998.9508    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.6623 9998.5384    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3768 9998.9508    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
10000.3768 9999.7759    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
 9998.236810000.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5221 9999.7758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.5221 9998.9507    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2367 9998.5382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12  7  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 13 14  1  0  0  0  0
 13 18  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 20  6  1  0  0  0  0
 22  5  1  0  0  0  0
  8  3  1  0  0  0  0
  7  4  1  0  0  0  0
  1 16  2  0  0  0  0
 18 10  1  6  0  0  0
 17  2  1  1  0  0  0
 14 19  2  0  0  0  0
 22 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0332353

> <DATABASE_NAME>
NP-MRD

> <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

> <FORMULA>
C15H12O7

> <MOLECULAR_WEIGHT>
304.2516

> <EXACT_MASS>
304.058302738

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
29.031784137700317

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2R,3R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
1.07

> <JCHEM_LOGP>
1.8163842679999997

> <ALOGPS_LOGS>
-2.42

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.00135173078782

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.742826994062549

> <JCHEM_PKA_STRONGEST_BASIC>
-4.04060800501074

> <JCHEM_POLAR_SURFACE_AREA>
127.45000000000002

> <JCHEM_REFRACTIVITY>
74.60890000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.16e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(+)-taxifolin

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  O   UNK     0    8666.0358662.387   0.000  0.00  0.00           O+0
HETATM    2  O   UNK     0    8668.6978663.934   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0    8670.0368670.872   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0    8672.7008669.332   0.000  0.00  0.00           O+0
HETATM    5  O   UNK     0    8663.3758662.387   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0    8660.7088667.026   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0    8671.3668668.565   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8670.0338669.335   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8668.6998668.565   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8668.6998667.025   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8670.0328666.255   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8671.3668667.025   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0    8666.0368667.018   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0    8664.7038666.248   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.7038664.708   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8666.0368663.938   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8667.3708664.708   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8667.3708666.248   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8663.3758667.018   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8662.0418666.248   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8662.0418664.708   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0    8663.3758663.938   0.000  0.00  0.00           C+0
CONECT    1   16                                                            
CONECT    2   17                                                            
CONECT    3    8                                                            
CONECT    4    7                                                            
CONECT    5   22                                                            
CONECT    6   20                                                            
CONECT    7    8   12    4                                                  
CONECT    8    7    9    3                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   18                                                  
CONECT   11   10   12                                                       
CONECT   12   11    7                                                       
CONECT   13   14   18                                                       
CONECT   14   15   13   19                                                  
CONECT   15   14   16   22                                                  
CONECT   16   15   17    1                                                  
CONECT   17   16   18    2                                                  
CONECT   18   17   13   10                                                  
CONECT   19   20   14                                                       
CONECT   20   19   21    6                                                  
CONECT   21   20   22                                                       
CONECT   22   21    5   15                                                  
MASTER        0    0    0    0    0    0    0    0   22    0   48    0
END

View in JSmol

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 Mass

304.2516 Da

Monoisotopic Mass

304.05830 Da

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-10	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-10	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-10	View Spectrum
1D NMR	[¹³C, ] NMR Spectrum (2D, 201 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-10	View Spectrum
1D NMR	[¹H, ] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	bgnzk@missouri.edu	MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-01-10	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.133705802, CD₃OD, simulated)	bgnzk@missouri.edu	Sumner Lab, MU Metabolomics Center, University of Missouri, Columbia. MO, USA	Dr. Bharat Goel	2024-05-14	View Spectrum

Species

Species of Origin

Not Available

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 )

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