NP-MRD: Showing NP-Card for 3'-O-(3,4-Di-O-methylgalloyl)procyanidin B2 (NP0086203)

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Record Information

Version

2.0

Created at

2022-04-29 06:33:21 UTC

Updated at

2022-04-29 06:33:21 UTC

NP-MRD ID

NP0086203

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3'-O-(3,4-Di-O-methylgalloyl)procyanidin B2

Description

3'-O-(3,4-Di-O-methylgalloyl)procyanidin B2 is found in Fagopyrum esculentum . Based on a literature review very few articles have been published on (2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3-hydroxy-4,5-dimethoxybenzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304292208332D          

 55 61  0  0  1  0            999 V2000
   -4.2868   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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 31 73  1  0
 30 72  1  0
 41 79  1  6
 49 84  1  0
 48 83  1  0
 46 82  1  0
 44 81  1  0
 43 80  1  0
M  END


  Mrv1652304292208332D          

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   -5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0013    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.7145    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.1994   -0.5701    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.1434   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  2  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
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  4  8  1  0  0  0  0
  9  8  1  6  0  0  0
  9 10  1  0  0  0  0
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 12 47  1  0  0  0  0
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 50 51  2  0  0  0  0
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 53 54  2  0  0  0  0
 47 54  1  0  0  0  0
 54 55  1  0  0  0  0
  9 55  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0086203

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=C(OC)C(O)=CC(=C1)C(=O)O[C@@H]1CC2=C(O)C=C(O)C([C@@H]3[C@@H](O)[C@H](OC4=CC(O)=CC(O)=C34)C3=CC(O)=C(O)C=C3)=C2O[C@@H]1C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C39H34O16/c1-51-29-10-17(9-27(48)38(29)52-2)39(50)54-30-13-19-22(43)14-26(47)32(37(19)55-35(30)15-3-5-20(41)23(44)7-15)33-31-25(46)11-18(40)12-28(31)53-36(34(33)49)16-4-6-21(42)24(45)8-16/h3-12,14,30,33-36,40-49H,13H2,1-2H3/t30-,33-,34-,35-,36-/m1/s1

> <INCHI_KEY>
HQALWOFLWXEXSU-VNCSWJDHSA-N

> <FORMULA>
C39H34O16

> <MOLECULAR_WEIGHT>
758.685

> <EXACT_MASS>
758.184685015

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
89

> <JCHEM_AVERAGE_POLARIZABILITY>
74.87679147545515

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3-hydroxy-4,5-dimethoxybenzoate

> <ALOGPS_LOGP>
3.81

> <JCHEM_LOGP>
4.992137009333334

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.044462403643909

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.62903233612003

> <JCHEM_PKA_STRONGEST_BASIC>
-4.408710789977516

> <JCHEM_POLAR_SURFACE_AREA>
265.52

> <JCHEM_REFRACTIVITY>
191.2373

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3-hydroxy-4,5-dimethoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 29-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   29-APR-22         0                                  
HETATM    1  O   UNK     0      -8.002  -7.700   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -6.668  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.668  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -5.335  -9.240   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.001  -2.310   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001  -0.770   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -8.002   0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -10.669   0.000   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0     -10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -6.668   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -8.002   4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -9.336   3.850   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0     -10.669   4.620   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0     -12.003   3.850   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0     -13.337   4.620   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0     -10.669   6.160   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0     -12.003   6.930   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0     -13.337   6.160   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -9.336   6.930   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      -9.336   8.470   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      -8.002   6.160   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0      -1.334   3.850   0.000  0.00  0.00           O+0
HETATM   44  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   46  O   UNK     0       1.334  -0.770   0.000  0.00  0.00           O+0
HETATM   47  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   49  O   UNK     0       2.239  -1.064   0.000  0.00  0.00           O+0
HETATM   50  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   51  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0       4.001  -5.390   0.000  0.00  0.00           O+0
HETATM   53  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   54  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM   55  O   UNK     0      -1.334  -5.390   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    5                                                  
CONECT    3    2    4                                                       
CONECT    4    3    8                                                       
CONECT    5    2    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    4    9                                                  
CONECT    9    8   10   55                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   47                                                  
CONECT   13   12   14   45                                                  
CONECT   14   13   15   41                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   25                                                  
CONECT   17   16   18   23                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22   17                                                       
CONECT   24   21                                                            
CONECT   25   16   26   40                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   39                                                  
CONECT   28   27   29   38                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34   36                                                  
CONECT   34   33   35                                                       
CONECT   35   34                                                            
CONECT   36   33   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   28                                                       
CONECT   39   27                                                            
CONECT   40   25   41                                                       
CONECT   41   40   14   42                                                  
CONECT   42   41   43   44                                                  
CONECT   43   42                                                            
CONECT   44   42   45                                                       
CONECT   45   44   13   46                                                  
CONECT   46   45                                                            
CONECT   47   12   48   54                                                  
CONECT   48   47   49   50                                                  
CONECT   49   48                                                            
CONECT   50   48   51                                                       
CONECT   51   50   52   53                                                  
CONECT   52   51                                                            
CONECT   53   51   54                                                       
CONECT   54   53   47   55                                                  
CONECT   55   54    9                                                       
MASTER        0    0    0    0    0    0    0    0   55    0  122    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R)-2-(3,4-Dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3-hydroxy-4,5-dimethoxybenzoic acid	Generator

Chemical Formula

C₃₉H₃₄O₁₆

Average Mass

758.6850 Da

Monoisotopic Mass

758.18469 Da

IUPAC Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3-hydroxy-4,5-dimethoxybenzoate

Traditional Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3R,4R)-2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-3,4-dihydro-2H-1-benzopyran-4-yl]-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3-hydroxy-4,5-dimethoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=C(OC)C(O)=CC(=C1)C(=O)O[C@@H]1CC2=C(O)C=C(O)C([C@@H]3[C@@H](O)[C@H](OC4=CC(O)=CC(O)=C34)C3=CC(O)=C(O)C=C3)=C2O[C@@H]1C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C39H34O16/c1-51-29-10-17(9-27(48)38(29)52-2)39(50)54-30-13-19-22(43)14-26(47)32(37(19)55-35(30)15-3-5-20(41)23(44)7-15)33-31-25(46)11-18(40)12-28(31)53-36(34(33)49)16-4-6-21(42)24(45)8-16/h3-12,14,30,33-36,40-49H,13H2,1-2H3/t30-,33-,34-,35-,36-/m1/s1

InChI Key

HQALWOFLWXEXSU-VNCSWJDHSA-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
Fagopyrum esculentum	Plant	KNApSAcK

Chemical Taxonomy

Classification

Not classified

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	3.81	ALOGPS
logP	4.99	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	8.63	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	265.52 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	191.24 m³·mol⁻¹	ChemAxon
Polarizability	74.88 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00056359

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

163183949

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 3'-O-(3,4-Di-O-methylgalloyl)procyanidin B2 (NP0086203)

MOL for NP0086203 (3'-O-(3,4-Di-O-methylgalloyl)procyanidin B2)

3D MOL for NP0086203 (3'-O-(3,4-Di-O-methylgalloyl)procyanidin B2)

3D SDF for NP0086203 (3'-O-(3,4-Di-O-methylgalloyl)procyanidin B2)

3D-SDF for NP0086203 (3'-O-(3,4-Di-O-methylgalloyl)procyanidin B2)

PDB for NP0086203 (3'-O-(3,4-Di-O-methylgalloyl)procyanidin B2)

3D PDB for NP0086203 (3'-O-(3,4-Di-O-methylgalloyl)procyanidin B2)

SMILES for NP0086203 (3'-O-(3,4-Di-O-methylgalloyl)procyanidin B2)

INCHI for NP0086203 (3'-O-(3,4-Di-O-methylgalloyl)procyanidin B2)

Structure for NP0086203 (3'-O-(3,4-Di-O-methylgalloyl)procyanidin B2)

3D Structure for NP0086203 (3'-O-(3,4-Di-O-methylgalloyl)procyanidin B2)