NP-MRD: Showing NP-Card for Catechin-(4alpha->8)-epicatechin 3'-gallate (NP0045683)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-17 19:33:56 UTC

Updated at

2022-03-17 19:33:56 UTC

NP-MRD ID

NP0045683

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Catechin-(4alpha->8)-epicatechin 3'-gallate

Description

Catechin-(4alpha->8)-epicatechin 3'-gallate is found in Camellia sinensis , Fagopyrum esculentum , Mallotus japonicus and Rheum sp..

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241212182D          

 53 59  0  0  0  0            999 V2000
   -4.0071    0.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7216    0.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7216   -0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0071   -0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2927   -0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2927    0.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782    0.7956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782   -0.8545    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8637   -0.4420    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8637    0.3830    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1493    0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4348    2.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1493    1.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4348    0.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797    0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797    1.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4348    2.8581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941    2.0331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1493   -0.8545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4361    0.7955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0366   -1.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782   -1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2927   -2.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2927   -2.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782   -3.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8637   -2.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8637   -2.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1493   -1.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1493   -3.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4348   -2.9170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4348   -2.0920    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2797   -1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797   -0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -2.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941    0.3830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4231   -0.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5652   -1.8857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782   -4.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -4.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -5.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -5.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4231   -5.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4231   -4.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -4.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -5.8045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -6.6295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797   -4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4348   -4.5670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797   -3.3295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  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
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
  9 19  1  1  0  0  0
  2 20  1  0  0  0  0
  4 21  1  0  0  0  0
  8 22  1  6  0  0  0
 22 23  2  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
 23 40  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 41  1  0  0  0  0
 27 26  2  0  0  0  0
 26 29  1  0  0  0  0
 28 27  1  0  0  0  0
 28 31  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 53  1  6  0  0  0
 31 32  1  6  0  0  0
 34 32  2  0  0  0  0
 32 35  1  0  0  0  0
 33 34  1  0  0  0  0
 33 37  2  0  0  0  0
 33 38  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 39  1  0  0  0  0
 42 43  2  0  0  0  0
 42 47  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 46 49  1  0  0  0  0
 45 50  1  0  0  0  0
 43 51  1  0  0  0  0
 51 52  2  0  0  0  0
 51 53  1  0  0  0  0
M  END


  Mrv0541 02241212182D          

 53 59  0  0  0  0            999 V2000
   -4.0071    0.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7216    0.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7216   -0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0071   -0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2927   -0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2927    0.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782    0.7956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782   -0.8545    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8637   -0.4420    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.8637    0.3830    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1493    0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4348    2.0331    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1493    1.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4348    0.3830    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797    0.7955    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797    1.6206    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4348    2.8581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941    2.0331    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1493   -0.8545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4361    0.7955    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0366   -1.4143    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782   -1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2927   -2.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2927   -2.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782   -3.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8637   -2.9170    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8637   -2.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1493   -1.6795    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1493   -3.3295    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4348   -2.9170    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.4348   -2.0920    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.2797   -1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -0.4420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797   -0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -2.0920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -1.6795    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -0.8545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941    0.3830    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4231   -0.4420    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5652   -1.8857    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5782   -4.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -4.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9941   -5.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -5.8045    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4231   -5.3920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4231   -4.5670    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -4.1545    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1375   -5.8045    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7086   -6.6295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797   -4.1545    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4348   -4.5670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2797   -3.3295    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  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
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 12 17  1  0  0  0  0
 16 18  1  0  0  0  0
  9 19  1  1  0  0  0
  2 20  1  0  0  0  0
  4 21  1  0  0  0  0
  8 22  1  6  0  0  0
 22 23  2  0  0  0  0
 22 27  1  0  0  0  0
 23 24  1  0  0  0  0
 23 40  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 25 41  1  0  0  0  0
 27 26  2  0  0  0  0
 26 29  1  0  0  0  0
 28 27  1  0  0  0  0
 28 31  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 53  1  6  0  0  0
 31 32  1  6  0  0  0
 34 32  2  0  0  0  0
 32 35  1  0  0  0  0
 33 34  1  0  0  0  0
 33 37  2  0  0  0  0
 33 38  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 39  1  0  0  0  0
 42 43  2  0  0  0  0
 42 47  1  0  0  0  0
 43 44  1  0  0  0  0
 44 45  2  0  0  0  0
 45 46  1  0  0  0  0
 46 47  2  0  0  0  0
 47 48  1  0  0  0  0
 46 49  1  0  0  0  0
 45 50  1  0  0  0  0
 43 51  1  0  0  0  0
 51 52  2  0  0  0  0
 51 53  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045683

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1[C@H](OC2=C([C@H]1C1=C(O)C=C(O)C3=C1O[C@@H]([C@@H](C3)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1)C(O)=CC(O)=C2)C1=CC(O)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C37H30O16/c38-16-9-23(44)29-27(10-16)51-35(14-2-4-19(40)22(43)6-14)33(49)31(29)30-24(45)12-20(41)17-11-28(52-37(50)15-7-25(46)32(48)26(47)8-15)34(53-36(17)30)13-1-3-18(39)21(42)5-13/h1-10,12,28,31,33-35,38-49H,11H2/t28-,31+,33+,34-,35-/m1/s1

> <INCHI_KEY>
VLFKNLZNDSEVBZ-GUFPFSRMSA-N

> <FORMULA>
C37H30O16

> <MOLECULAR_WEIGHT>
730.6245

> <EXACT_MASS>
730.153384912

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
69.79039639294308

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-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 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
3.32

> <JCHEM_LOGP>
4.700348897333333

> <ALOGPS_LOGS>
-4.00

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.848679852950948

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.025033737550777

> <JCHEM_PKA_STRONGEST_BASIC>
-5.214620821846933

> <JCHEM_POLAR_SURFACE_AREA>
287.52

> <JCHEM_REFRACTIVITY>
182.27270000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.37e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-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 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -7.480   1.485   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.814   0.715   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.814  -0.825   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.480  -1.595   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.146  -0.825   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -6.146   0.715   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -4.813   1.485   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -4.813  -1.595   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.479  -0.825   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.479   0.715   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.145   1.485   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.812   3.795   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.145   3.025   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.812   0.715   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.522   1.485   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.522   3.025   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -0.812   5.335   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       1.856   3.795   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -2.145  -1.595   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0     -10.147   1.485   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -7.535  -2.640   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.813  -3.135   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -6.146  -3.905   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -6.146  -5.445   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -4.813  -6.215   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -3.479  -5.445   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -3.479  -3.905   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -2.145  -3.135   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -2.145  -6.215   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.812  -5.445   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.812  -3.905   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       0.522  -3.135   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       1.856  -0.825   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       0.522  -1.595   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.856  -3.905   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.189  -3.135   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.189  -1.595   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       1.856   0.715   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0       4.523  -0.825   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -6.655  -3.520   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -4.813  -7.755   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       3.189  -7.755   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0       1.856  -8.525   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       1.856 -10.065   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0       3.189 -10.835   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0       4.523 -10.065   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       4.523  -8.525   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0       5.857  -7.755   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0       5.857 -10.835   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0       3.189 -12.375   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0       0.522  -7.755   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0      -0.812  -8.525   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       0.522  -6.215   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   21                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9   22                                                  
CONECT    9    8   10   19                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16   17                                                  
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16                                                       
CONECT   16   12   15   18                                                  
CONECT   17   12                                                            
CONECT   18   16                                                            
CONECT   19    9                                                            
CONECT   20    2                                                            
CONECT   21    4                                                            
CONECT   22    8   23   27                                                  
CONECT   23   22   24   40                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   41                                                  
CONECT   26   25   27   29                                                  
CONECT   27   22   26   28                                                  
CONECT   28   27   31                                                       
CONECT   29   26   30                                                       
CONECT   30   29   31   53                                                  
CONECT   31   28   30   32                                                  
CONECT   32   31   34   35                                                  
CONECT   33   34   37   38                                                  
CONECT   34   32   33                                                       
CONECT   35   32   36                                                       
CONECT   36   35   37                                                       
CONECT   37   33   36   39                                                  
CONECT   38   33                                                            
CONECT   39   37                                                            
CONECT   40   23                                                            
CONECT   41   25                                                            
CONECT   42   43   47                                                       
CONECT   43   42   44   51                                                  
CONECT   44   43   45                                                       
CONECT   45   44   46   50                                                  
CONECT   46   45   47   49                                                  
CONECT   47   42   46   48                                                  
CONECT   48   47                                                            
CONECT   49   46                                                            
CONECT   50   45                                                            
CONECT   51   43   52   53                                                  
CONECT   52   51                                                            
CONECT   53   30   51                                                       
MASTER        0    0    0    0    0    0    0    0   53    0  118    0
END

View in JSmol

Synonyms

Value	Source
(-)-Epicatechin-(4alpha->8)-(+)-catechin-3'-O-gallate	ChEBI
(-)-Epicatechin-(4a->8)-(+)-catechin-3'-O-gallate	Generator
(-)-Epicatechin-(4a->8)-(+)-catechin-3'-O-gallic acid	Generator
(-)-Epicatechin-(4alpha->8)-(+)-catechin-3'-O-gallic acid	Generator
(-)-Epicatechin-(4α->8)-(+)-catechin-3'-O-gallate	Generator
(-)-Epicatechin-(4α->8)-(+)-catechin-3'-O-gallic acid	Generator
Catechin-(4a->8)-epicatechin 3'-gallate	Generator
Catechin-(4a->8)-epicatechin 3'-gallic acid	Generator
Catechin-(4alpha->8)-epicatechin 3'-gallic acid	Generator
Catechin-(4α->8)-epicatechin 3'-gallate	Generator
Catechin-(4α->8)-epicatechin 3'-gallic acid	Generator

Chemical Formula

C₃₇H₃₀O₁₆

Average Mass

730.6245 Da

Monoisotopic Mass

730.15338 Da

IUPAC Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-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 3,4,5-trihydroxybenzoate

Traditional Name

(2R,3R)-2-(3,4-dihydroxyphenyl)-8-[(2R,3S,4S)-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 3,4,5-trihydroxybenzoate

CAS Registry Number

89064-33-5

SMILES

O[C@@H]1[C@H](OC2=C([C@H]1C1=C(O)C=C(O)C3=C1O[C@@H]([C@@H](C3)OC(=O)C1=CC(O)=C(O)C(O)=C1)C1=CC(O)=C(O)C=C1)C(O)=CC(O)=C2)C1=CC(O)=C(O)C=C1

InChI Identifier

InChI=1S/C37H30O16/c38-16-9-23(44)29-27(10-16)51-35(14-2-4-19(40)22(43)6-14)33(49)31(29)30-24(45)12-20(41)17-11-28(52-37(50)15-7-25(46)32(48)26(47)8-15)34(53-36(17)30)13-1-3-18(39)21(42)5-13/h1-10,12,28,31,33-35,38-49H,11H2/t28-,31+,33+,34-,35-/m1/s1

InChI Key

VLFKNLZNDSEVBZ-GUFPFSRMSA-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
Camellia sinensis	Plant	KNApSAcK
Fagopyrum esculentum	Plant	KNApSAcK
Mallotus japonicus	Plant	KNApSAcK
Rheum sp.	Plant	KNApSAcK
Vitis vinifera L.	FooDB	KNAPSACK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as biflavonoids and polyflavonoids. These are organic compounds containing at least two flavan/flavone units. These units are usually linked through CC or C-O-C bonds. Some examples include C2-O-C3, C2-O-C4, C3'-C3''', and C6-C8''.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Biflavonoids and polyflavonoids

Direct Parent

Biflavonoids and polyflavonoids

Alternative Parents

Substituents

B-type proanthocyanidin
Bi- and polyflavonoid skeleton
Proanthocyanidin
Catechin gallate
Catechin
3'-hydroxyflavonoid
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Flavan-3-ol
Hydroxyflavonoid
Flavan
Galloyl ester
Gallic acid or derivatives
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
1-benzopyran
Benzopyran
Chromane
Benzoate ester
Pyrogallol derivative
Benzoic acid or derivatives
Benzenetriol
Benzoyl
Catechol
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Phenol
Alkyl aryl ether
Benzenoid
Monocyclic benzene moiety
Carboxylic acid ester
Secondary alcohol
Ether
Oxacycle
Polyol
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

polyphenol (CHEBI:75655 )
gallate ester (CHEBI:75655 )
proanthocyanidin (CHEBI:75655 )
biflavonoid (CHEBI:75655 )

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	3.32	ALOGPS
logP	4.7	ChemAxon
logS	-4	ALOGPS
pKa (Strongest Acidic)	8.03	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	15	ChemAxon
Hydrogen Donor Count	12	ChemAxon
Polar Surface Area	287.52 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	182.27 m³·mol⁻¹	ChemAxon
Polarizability	69.79 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

FDB001638

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

15593123

PDB ID

Not Available

ChEBI ID

75655

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Catechin-(4alpha->8)-epicatechin 3'-gallate (NP0045683)

MOL for NP0045683 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

3D MOL for NP0045683 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

3D SDF for NP0045683 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

3D-SDF for NP0045683 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

PDB for NP0045683 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

3D PDB for NP0045683 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

SMILES for NP0045683 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

INCHI for NP0045683 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

Structure for NP0045683 (Catechin-(4alpha->8)-epicatechin 3'-gallate)

3D Structure for NP0045683 (Catechin-(4alpha->8)-epicatechin 3'-gallate)