NP-MRD: Showing NP-Card for Catechin-(2'->2')-taxifolin (NP0056152)

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Record Information

Version

2.0

Created at

2022-04-28 02:00:52 UTC

Updated at

2022-04-28 02:00:52 UTC

NP-MRD ID

NP0056152

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Catechin-(2'->2')-taxifolin

Description

(2S,3R)-3,5,7-trihydroxy-2-{2',3',5,6-tetrahydroxy-6'-[(2R,3S)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-[1,1'-biphenyl]-2-yl}-3,4-dihydro-2H-1-benzopyran-4-one belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol. Catechin-(2'->2')-taxifolin is found in Salix spp. Based on a literature review very few articles have been published on (2S,3R)-3,5,7-trihydroxy-2-{2',3',5,6-tetrahydroxy-6'-[(2R,3S)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-[1,1'-biphenyl]-2-yl}-3,4-dihydro-2H-1-benzopyran-4-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282204002D          

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M  END

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M  END


  Mrv1652304282204002D          

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    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4849   -1.8076    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2868   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8579   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
  9 11  1  6  0  0  0
  8 12  1  1  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  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
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 22 25  1  0  0  0  0
 26 19  1  1  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 26 32  1  0  0  0  0
 32 33  1  1  0  0  0
 29 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 28 37  1  0  0  0  0
 36 38  1  0  0  0  0
 34 39  1  0  0  0  0
 16 40  1  0  0  0  0
 15 41  1  0  0  0  0
  3 42  1  0  0  0  0
  1 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056152

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O)C(O)=C1C1=C(C=CC(O)=C1O)[C@@H]1OC2=C(C(O)=CC(O)=C2)C(=O)[C@@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H24O13/c31-10-5-17(35)14-9-19(37)29(42-20(14)7-10)12-1-3-15(33)25(38)22(12)23-13(2-4-16(34)26(23)39)30-28(41)27(40)24-18(36)6-11(32)8-21(24)43-30/h1-8,19,28-39,41H,9H2/t19-,28-,29+,30-/m0/s1

> <INCHI_KEY>
PWKAVSCALZMWDV-YMOFZHSNSA-N

> <FORMULA>
C30H24O13

> <MOLECULAR_WEIGHT>
592.509

> <EXACT_MASS>
592.121690833

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
67

> <JCHEM_AVERAGE_POLARIZABILITY>
56.67653807487261

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R)-3,5,7-trihydroxy-2-{2',3',5,6-tetrahydroxy-6'-[(2R,3S)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-[1,1'-biphenyl]-2-yl}-3,4-dihydro-2H-1-benzopyran-4-one

> <ALOGPS_LOGP>
2.55

> <JCHEM_LOGP>
3.285470829333333

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.48447836192211

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.681933232931816

> <JCHEM_PKA_STRONGEST_BASIC>
-5.078081827880426

> <JCHEM_POLAR_SURFACE_AREA>
237.82999999999996

> <JCHEM_REFRACTIVITY>
147.68680000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.54e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R)-3,5,7-trihydroxy-2-{2',3',5,6-tetrahydroxy-6'-[(2R,3S)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-[1,1'-biphenyl]-2-yl}-2,3-dihydro-1-benzopyran-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668 -10.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.667  -9.240   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.170  -6.021   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -4.906  -6.636   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0      -6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       0.905  -3.374   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0      -8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -5.335 -13.860   0.000  0.00  0.00           O+0
CONECT    1    2    6   43                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   42                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9                                                            
CONECT   12    8   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   41                                                  
CONECT   16   15   17   40                                                  
CONECT   17   16   12   18                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20   26                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   25                                                  
CONECT   23   22   18   24                                                  
CONECT   24   23                                                            
CONECT   25   22                                                            
CONECT   26   19   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   37                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   26   33                                                  
CONECT   33   32                                                            
CONECT   34   29   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   38                                                  
CONECT   37   36   28                                                       
CONECT   38   36                                                            
CONECT   39   34                                                            
CONECT   40   16                                                            
CONECT   41   15                                                            
CONECT   42    3                                                            
CONECT   43    1                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   96    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₂₄O₁₃

Average Mass

592.5090 Da

Monoisotopic Mass

592.12169 Da

IUPAC Name

(2S,3R)-3,5,7-trihydroxy-2-{2',3',5,6-tetrahydroxy-6'-[(2R,3S)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-[1,1'-biphenyl]-2-yl}-3,4-dihydro-2H-1-benzopyran-4-one

Traditional Name

(2S,3R)-3,5,7-trihydroxy-2-{2',3',5,6-tetrahydroxy-6'-[(2R,3S)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-2-yl]-[1,1'-biphenyl]-2-yl}-2,3-dihydro-1-benzopyran-4-one

CAS Registry Number

Not Available

SMILES

O[C@H]1CC2=C(O)C=C(O)C=C2O[C@@H]1C1=CC=C(O)C(O)=C1C1=C(C=CC(O)=C1O)[C@@H]1OC2=C(C(O)=CC(O)=C2)C(=O)[C@@H]1O

InChI Identifier

InChI=1S/C30H24O13/c31-10-5-17(35)14-9-19(37)29(42-20(14)7-10)12-1-3-15(33)25(38)22(12)23-13(2-4-16(34)26(23)39)30-28(41)27(40)24-18(36)6-11(32)8-21(24)43-30/h1-8,19,28-39,41H,9H2/t19-,28-,29+,30-/m0/s1

InChI Key

PWKAVSCALZMWDV-YMOFZHSNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Salix spp.	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechins. Catechins are compounds containing a catechin moiety, which is a 3,4-dihydro-2-chromene-3,5.7-Tiol.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechins

Alternative Parents

Substituents

Catechin
Hydroxyflavonoid
Flavanonol
Flavanone
7-hydroxyflavonoid
5-hydroxyflavonoid
4'-hydroxyflavonoid
3-hydroxyflavonoid
3'-hydroxyflavonoid
Biphenol
Biphenyl
Chromone
1-benzopyran
Benzopyran
Chromane
Aryl alkyl ketone
Aryl ketone
Catechol
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Vinylogous acid
Secondary alcohol
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Alcohol
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

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	2.55	ALOGPS
logP	3.29	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	7.68	ChemAxon
pKa (Strongest Basic)	-5.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	237.83 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	147.69 m³·mol⁻¹	ChemAxon
Polarizability	56.68 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

163184627

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Catechin-(2'->2')-taxifolin (NP0056152)

MOL for NP0056152 (Catechin-(2'->2')-taxifolin)

3D MOL for NP0056152 (Catechin-(2'->2')-taxifolin)

3D SDF for NP0056152 (Catechin-(2'->2')-taxifolin)

3D-SDF for NP0056152 (Catechin-(2'->2')-taxifolin)

PDB for NP0056152 (Catechin-(2'->2')-taxifolin)

3D PDB for NP0056152 (Catechin-(2'->2')-taxifolin)

SMILES for NP0056152 (Catechin-(2'->2')-taxifolin)

INCHI for NP0056152 (Catechin-(2'->2')-taxifolin)

Structure for NP0056152 (Catechin-(2'->2')-taxifolin)

3D Structure for NP0056152 (Catechin-(2'->2')-taxifolin)