NP-MRD: Showing NP-Card for Epicatechin-(4beta->8)-catechin 3-gallate (NP0045684)

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Record Information

Version

2.0

Created at

2022-03-17 19:33:57 UTC

Updated at

2022-03-17 19:33:57 UTC

NP-MRD ID

NP0045684

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epicatechin-(4beta->8)-catechin 3-gallate

Description

Epicatechin-(4beta->8)-catechin 3-gallate is found in Camellia sinensis and Hamamelis virginiana.

Structure

MOL SDF PDB SMILES InChI


  Mrv1652307301920012D          

 53 59  0  0  0  0            999 V2000
    2.7703    1.3092    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7615    2.9581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4786    2.5482    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4838    1.7206    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0497    2.5405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533    1.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3449    1.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6328    1.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6333    2.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3420    2.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0808    2.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1993    1.3102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1876    2.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1819    3.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8935    4.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6110    3.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6127    2.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9006    2.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3277    2.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3238    4.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3477    0.4829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4848    0.0727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1993    0.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9137    0.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6281    0.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9137   -0.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3426    0.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0571    0.4852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3426   -0.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0571   -1.1648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6281   -1.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6281   -1.9898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4921   -1.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4934   -0.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7785   -0.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7803   -2.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0650   -1.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0614   -0.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3424   -0.4335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6219   -0.8507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6254   -1.6838    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3491   -2.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7828   -2.9120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0879   -2.0985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0910   -0.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0920    0.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8067    0.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5211    0.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5162   -0.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8010   -0.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2280   -0.8651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2373    0.7907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2082   -0.4350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  4  1  0  0  0  0
  5  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  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  5  1  0  0  0  0
  9 11  1  0  0  0  0
  4 12  1  6  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 13  1  0  0  0  0
  3 13  1  6  0  0  0
 17 19  1  0  0  0  0
 16 20  1  0  0  0  0
  7 21  1  0  0  0  0
 12 23  1  0  0  0  0
 23 22  2  0  0  0  0
 23 24  1  0  0  0  0
 25 24  2  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 31  2  0  0  0  0
 31 29  1  0  0  0  0
 29 27  2  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
 31 32  1  0  0  0  0
 49 51  1  0  0  0  0
 40 41  1  0  0  0  0
 48 52  1  0  0  0  0
 41 42  1  0  0  0  0
 37 38  1  0  0  0  0
 36 43  1  0  0  0  0
 34 35  1  0  0  0  0
 41 44  1  6  0  0  0
 35 38  2  0  0  0  0
 33 34  2  0  0  0  0
 45 46  2  0  0  0  0
 37 36  2  0  0  0  0
 46 47  1  0  0  0  0
 36 33  1  0  0  0  0
 47 48  2  0  0  0  0
 37 42  1  0  0  0  0
 48 49  1  0  0  0  0
 38 39  1  0  0  0  0
 49 50  2  0  0  0  0
 50 45  1  0  0  0  0
 40 45  1  1  0  0  0
 39 40  1  0  0  0  0
 34 53  1  0  0  0  0
  1 35  1  1  0  0  0
M  END


  Mrv1652307301920012D          

 53 59  0  0  0  0            999 V2000
    2.7703    1.3092    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.7615    2.9581    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4786    2.5482    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4838    1.7206    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0497    2.5405    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0533    1.7194    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3449    1.3079    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6328    1.7160    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6333    2.5402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3420    2.9481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0808    2.9533    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1993    1.3102    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1876    2.9623    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1819    3.7883    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8935    4.2044    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6110    3.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6127    2.9664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9006    2.5539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3277    2.5550    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3238    4.2108    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3477    0.4829    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4848    0.0727    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1993    0.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9137    0.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6281    0.4852    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9137   -0.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3426    0.0727    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0571    0.4852    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3426   -0.7523    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0571   -1.1648    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.6281   -1.1648    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6281   -1.9898    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4921   -1.6743    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4934   -0.8470    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7785   -0.4340    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7803   -2.0870    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0650   -1.6779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0614   -0.8448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3424   -0.4335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6219   -0.8507    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.6254   -1.6838    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3491   -2.0997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7828   -2.9120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0879   -2.0985    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0910   -0.4409    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0920    0.3851    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8067    0.7956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5211    0.3812    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5162   -0.4481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8010   -0.8548    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2280   -0.8651    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2373    0.7907    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2082   -0.4350    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  6  1  0  0  0  0
  1  4  1  0  0  0  0
  5  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  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  5  1  0  0  0  0
  9 11  1  0  0  0  0
  4 12  1  6  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 13  1  0  0  0  0
  3 13  1  6  0  0  0
 17 19  1  0  0  0  0
 16 20  1  0  0  0  0
  7 21  1  0  0  0  0
 12 23  1  0  0  0  0
 23 22  2  0  0  0  0
 23 24  1  0  0  0  0
 25 24  2  0  0  0  0
 24 26  1  0  0  0  0
 25 27  1  0  0  0  0
 26 31  2  0  0  0  0
 31 29  1  0  0  0  0
 29 27  2  0  0  0  0
 27 28  1  0  0  0  0
 29 30  1  0  0  0  0
 31 32  1  0  0  0  0
 49 51  1  0  0  0  0
 40 41  1  0  0  0  0
 48 52  1  0  0  0  0
 41 42  1  0  0  0  0
 37 38  1  0  0  0  0
 36 43  1  0  0  0  0
 34 35  1  0  0  0  0
 41 44  1  6  0  0  0
 35 38  2  0  0  0  0
 33 34  2  0  0  0  0
 45 46  2  0  0  0  0
 37 36  2  0  0  0  0
 46 47  1  0  0  0  0
 36 33  1  0  0  0  0
 47 48  2  0  0  0  0
 37 42  1  0  0  0  0
 48 49  1  0  0  0  0
 38 39  1  0  0  0  0
 49 50  2  0  0  0  0
 50 45  1  0  0  0  0
 40 45  1  1  0  0  0
 39 40  1  0  0  0  0
 34 53  1  0  0  0  0
  1 35  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0045684

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CC2=C(O)C=C(O)C([C@@H]3[C@@H](OC(=O)C4=CC(O)=C(O)C(O)=C4)[C@H](OC4=C3C(O)=CC(O)=C4)C3=CC=C(O)C(O)=C3)=C2O[C@@H]1C1=CC=C(O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1S/C37H30O16/c38-16-9-23(44)29-28(10-16)51-34(14-2-4-19(40)22(43)6-14)36(53-37(50)15-7-25(46)32(49)26(47)8-15)31(29)30-24(45)12-20(41)17-11-27(48)33(52-35(17)30)13-1-3-18(39)21(42)5-13/h1-10,12,27,31,33-34,36,38-49H,11H2/t27-,31+,33+,34+,36+/m0/s1

> <INCHI_KEY>
BXWABJPTCUDBMM-NNJCKQBNSA-N

> <FORMULA>
C37H30O16

> <MOLECULAR_WEIGHT>
730.6245

> <EXACT_MASS>
730.153384912

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_ATOM_COUNT>
83

> <JCHEM_AVERAGE_POLARIZABILITY>
69.65053025348317

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <JCHEM_LOGP>
4.700348897333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.801308245449599

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.014799325247832

> <JCHEM_PKA_STRONGEST_BASIC>
-5.485687933076108

> <JCHEM_POLAR_SURFACE_AREA>
287.52

> <JCHEM_REFRACTIVITY>
182.2727

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0       5.171   2.444   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       5.155   5.522   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       6.493   4.757   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.503   3.212   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.826   4.742   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.833   3.210   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.510   2.441   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.181   3.203   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.182   4.742   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.505   5.503   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -0.151   5.513   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       7.839   2.446   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       7.817   5.530   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.806   7.071   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.135   7.848   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.474   7.085   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.477   5.537   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.148   4.767   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.812   4.769   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      11.804   7.860   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       2.516   0.901   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.505   0.136   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       7.839   0.906   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.172   0.136   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.506   0.906   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.172  -1.404   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      11.840   0.136   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      13.173   0.906   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      11.840  -1.404   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.173  -2.174   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.506  -2.174   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      10.506  -3.714   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       6.519  -3.125   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       6.521  -1.581   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.187  -0.810   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.190  -3.896   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       3.855  -3.132   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       3.848  -1.577   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.506  -0.809   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       1.161  -1.588   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       1.167  -3.143   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       2.518  -3.919   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       5.195  -5.436   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0      -0.164  -3.917   0.000  0.00  0.00           O+0
HETATM   45  C   UNK     0      -0.170  -0.823   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0      -0.172   0.719   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0      -1.506   1.485   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0      -2.839   0.712   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0      -2.830  -0.836   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0      -1.495  -1.596   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0      -4.159  -1.615   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0      -4.176   1.476   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       7.855  -0.812   0.000  0.00  0.00           O+0
CONECT    1    6    4   35                                                  
CONECT    2    5    3                                                       
CONECT    3    2    4   13                                                  
CONECT    4    1    3   12                                                  
CONECT    5    2    6   10                                                  
CONECT    6    1    5    7                                                  
CONECT    7    6    8   21                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9    5                                                       
CONECT   11    9                                                            
CONECT   12    4   23                                                       
CONECT   13   14   18    3                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   20                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17   13                                                       
CONECT   19   17                                                            
CONECT   20   16                                                            
CONECT   21    7                                                            
CONECT   22   23                                                            
CONECT   23   12   22   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   27                                                       
CONECT   26   24   31                                                       
CONECT   27   25   29   28                                                  
CONECT   28   27                                                            
CONECT   29   31   27   30                                                  
CONECT   30   29                                                            
CONECT   31   26   29   32                                                  
CONECT   32   31                                                            
CONECT   33   34   36                                                       
CONECT   34   35   33   53                                                  
CONECT   35   34   38    1                                                  
CONECT   36   43   37   33                                                  
CONECT   37   38   36   42                                                  
CONECT   38   37   35   39                                                  
CONECT   39   38   40                                                       
CONECT   40   41   45   39                                                  
CONECT   41   40   42   44                                                  
CONECT   42   41   37                                                       
CONECT   43   36                                                            
CONECT   44   41                                                            
CONECT   45   46   50   40                                                  
CONECT   46   45   47                                                       
CONECT   47   46   48                                                       
CONECT   48   52   47   49                                                  
CONECT   49   51   48   50                                                  
CONECT   50   49   45                                                       
CONECT   51   49                                                            
CONECT   52   48                                                            
CONECT   53   34                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  118    0
END

View in JSmol

Synonyms

Value	Source
(-)-Epicatechin-(4beta->8)-(+)-catechin-3-O-gallate	ChEBI
(-)-Epicatechin-(4b->8)-(+)-catechin-3-O-gallate	Generator
(-)-Epicatechin-(4b->8)-(+)-catechin-3-O-gallic acid	Generator
(-)-Epicatechin-(4beta->8)-(+)-catechin-3-O-gallic acid	Generator
(-)-Epicatechin-(4β->8)-(+)-catechin-3-O-gallate	Generator
(-)-Epicatechin-(4β->8)-(+)-catechin-3-O-gallic acid	Generator
Procyanidin dimer b1 3-gallic acid	Generator
Epicatechin-(4b->8)-catechin 3-gallate	Generator
Epicatechin-(4b->8)-catechin 3-gallic acid	Generator
Epicatechin-(4beta->8)-catechin 3-gallic acid	Generator
Epicatechin-(4β->8)-catechin 3-gallate	Generator
Epicatechin-(4β->8)-catechin 3-gallic acid	Generator

Chemical Formula

C₃₇H₃₀O₁₆

Average Mass

730.6245 Da

Monoisotopic Mass

730.15338 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

79907-45-2

SMILES

O[C@H]1CC2=C(O)C=C(O)C([C@@H]3[C@@H](OC(=O)C4=CC(O)=C(O)C(O)=C4)[C@H](OC4=C3C(O)=CC(O)=C4)C3=CC=C(O)C(O)=C3)=C2O[C@@H]1C1=CC=C(O)C(O)=C1

InChI Identifier

InChI=1S/C37H30O16/c38-16-9-23(44)29-28(10-16)51-34(14-2-4-19(40)22(43)6-14)36(53-37(50)15-7-25(46)32(49)26(47)8-15)31(29)30-24(45)12-20(41)17-11-27(48)33(52-35(17)30)13-1-3-18(39)21(42)5-13/h1-10,12,27,31,33-34,36,38-49H,11H2/t27-,31+,33+,34+,36+/m0/s1

InChI Key

BXWABJPTCUDBMM-NNJCKQBNSA-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	LOTUS Database	35616633
Hamamelis virginiana	LOTUS Database	35616633
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:75651 )
gallate ester (CHEBI:75651 )
proanthocyanidin (CHEBI:75651 )
biflavonoid (CHEBI:75651 )

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	4.7	ChemAxon
pKa (Strongest Acidic)	8.01	ChemAxon
pKa (Strongest Basic)	-5.5	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	69.65 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

FDB017139

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

12795888

PDB ID

Not Available

ChEBI ID

75651

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Epicatechin-(4beta->8)-catechin 3-gallate (NP0045684)

MOL for NP0045684 (Epicatechin-(4beta->8)-catechin 3-gallate)

3D MOL for NP0045684 (Epicatechin-(4beta->8)-catechin 3-gallate)

3D SDF for NP0045684 (Epicatechin-(4beta->8)-catechin 3-gallate)

3D-SDF for NP0045684 (Epicatechin-(4beta->8)-catechin 3-gallate)

PDB for NP0045684 (Epicatechin-(4beta->8)-catechin 3-gallate)

3D PDB for NP0045684 (Epicatechin-(4beta->8)-catechin 3-gallate)

SMILES for NP0045684 (Epicatechin-(4beta->8)-catechin 3-gallate)

INCHI for NP0045684 (Epicatechin-(4beta->8)-catechin 3-gallate)

Structure for NP0045684 (Epicatechin-(4beta->8)-catechin 3-gallate)

3D Structure for NP0045684 (Epicatechin-(4beta->8)-catechin 3-gallate)