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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (1) Show 1 protein XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:14:05 UTC

Update Date

2022-03-07 02:55:34 UTC

HMDB ID

HMDB0037965

Secondary Accession Numbers

HMDB37965

Metabolite Identification

Common Name

ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate

Description

ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate, also known as 3-galloylprocyanidin B1 or procyanidin dimer B1 3-O-gallate, 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''. ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate has been detected, but not quantified in, fruits. This could make ent-epicatechin-(4alpha->8)-ent-epicatechin 3-gallate a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv0541 02241208552D          

 53 59  0  0  0  0            999 V2000
   -2.9144    1.4300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1994    1.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1994    2.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858    3.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858    3.9050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3499   -1.8425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6363   -1.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6363   -0.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9144   -0.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1994   -0.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858   -0.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858    1.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7707    1.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7707    2.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0557    3.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6580    2.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3730    3.0800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9144   -1.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1994   -1.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4858   -1.8425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7707   -1.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7707   -0.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0639   -0.1924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9144    0.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6580   -3.9050    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6580   -3.0800    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0639   -2.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0639   -1.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6580   -1.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3730   -1.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3730   -2.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0797   -3.0800    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0557    1.4300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6580    1.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3730    1.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880    1.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8016    1.4300    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5166    0.1924    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3730    0.6050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880    0.1924    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0880   -0.6325    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4939   -1.0037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.4939   -0.1787    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9226   -2.6538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6349   -2.2412    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6349   -1.4162    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9226   -1.0051    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9226   -3.4788    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3499   -2.6538    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.3499   -1.0037    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 14  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  7 18  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
  9 24  1  0  0  0  0
 10 11  1  0  0  0  0
 10 19  1  0  0  0  0
 11 22  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 33  1  0  0  0  0
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 16 34  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
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 21 22  1  0  0  0  0
 21 28  1  0  0  0  0
 22 23  1  0  0  0  0
 23 43  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 31  1  0  0  0  0
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 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 40  1  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 38 39  1  0  0  0  0
 38 41  1  0  0  0  0
 40 41  2  0  0  0  0
 41 42  1  0  0  0  0
 43 44  1  0  0  0  0
 43 45  2  0  0  0  0
 44 46  2  0  0  0  0
 44 50  1  0  0  0  0
 46 47  1  0  0  0  0
 47 48  2  0  0  0  0
 47 51  1  0  0  0  0
 48 49  1  0  0  0  0
 48 52  1  0  0  0  0
 49 50  2  0  0  0  0
 49 53  1  0  0  0  0
M  END

HMDB0037965
     RDKit          3D
ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate
 83 89  0  0  0  0  0  0  0  0999 V2000
   -1.2514    0.5945    2.2595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8868    0.8514    1.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7722    0.0386    0.1147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9566   -1.1318    0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6825   -2.3012   -0.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9011   -2.6991    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1103   -2.3753    1.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2807   -2.7692    2.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2493   -3.4917    1.6226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4069   -3.8739    2.3064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0468   -3.8254    0.2893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0520   -4.5560   -0.3281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8866   -3.4242   -0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1275   -2.0240   -1.7685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4937   -1.1897   -2.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0018   -1.0111   -3.9040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3888   -0.1705   -4.8202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8696    0.0347   -6.1035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450    0.4836   -4.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2661    0.3069   -3.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4248    0.9790   -2.7530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294   -0.5207   -2.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
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    4.9202   -3.7406   -0.3993 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5631   -1.8419    0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4220   -1.0837    0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.0739    0.4331    1.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8600    1.6582    1.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0334    2.6617    2.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7520    3.8010    2.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3058    3.9473    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0427    5.0689    0.4827 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1196    2.9334   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
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    5.0449   -0.0428    3.0150 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6453   -1.3783    1.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7633    2.0335    1.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6686    3.9514    2.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5954    2.5468    3.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8872    4.5851    2.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2079    5.8377    1.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5600    2.3430   -2.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2594    1.0025   -0.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.3856    2.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2721   -0.6486    3.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1141   -2.2967    1.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167   -0.7937    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
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 52 82  1  0
 53 83  1  0
M  END


  Mrv0541 02241208552D          

 53 59  0  0  0  0            999 V2000
   -2.9144    1.4300    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1994    1.8425    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1994    2.6675    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0037965

> <DATABASE_NAME>
hmdb

> <SMILES>
OC1CC2=C(O)C=C(O)C(C3C(OC(=O)C4=CC(O)=C(O)C(O)=C4)C(OC4=CC(O)=CC(O)=C34)C3=CC=C(O)C(O)=C3)=C2OC1C1=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

> <INCHI_KEY>
BXWABJPTCUDBMM-UHFFFAOYSA-N

> <FORMULA>
C37H30O16

> <MOLECULAR_WEIGHT>
730.6245

> <EXACT_MASS>
730.153384912

> <JCHEM_ACCEPTOR_COUNT>
15

> <JCHEM_AVERAGE_POLARIZABILITY>
69.90425129191613

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
12

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(3,4-dihydroxyphenyl)-4-[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

> <ALOGPS_LOGP>
3.33

> <JCHEM_LOGP>
4.700348897333333

> <ALOGPS_LOGS>
-3.93

> <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>
182.27270000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.68e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(3,4-dihydroxyphenyl)-4-[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

$$$$

HMDB0037965
     RDKit          3D
ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate
 83 89  0  0  0  0  0  0  0  0999 V2000
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   -1.6825   -2.3012   -0.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9011   -2.6991    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1103   -2.3753    1.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.2493   -3.4917    1.6226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4069   -3.8739    2.3064 O   0  0  0  0  0  0  0  0  0  0  0  0
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  7 56  1  0
  8 57  1  0
 10 58  1  0
 12 59  1  0
 13 60  1  0
 16 61  1  0
 18 62  1  0
 19 63  1  0
 21 64  1  0
 23 65  1  0
 26 66  1  0
 27 67  1  0
 29 68  1  0
 33 69  1  0
 35 70  1  0
 36 71  1  0
 38 72  1  0
 40 73  1  0
 41 74  1  0
 42 75  1  0
 43 76  1  0
 44 77  1  0
 44 78  1  0
 46 79  1  0
 48 80  1  0
 50 81  1  0
 52 82  1  0
 53 83  1  0
M  END

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  O   UNK     0      -5.440   2.669   0.000  0.00  0.00           O+0
HETATM    2  C   UNK     0      -4.106   3.439   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.106   4.979   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.773   5.749   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.773   7.289   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0      -8.120  -3.439   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -6.788  -2.669   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.788  -1.129   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -5.440  -0.359   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.106  -1.129   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.773  -0.359   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.773   2.669   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.439   3.439   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.439   4.979   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.104   5.749   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.228   4.979   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       2.563   5.749   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0      -5.440  -3.439   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.106  -2.669   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.773  -3.439   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0      -1.439  -2.669   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -1.439  -1.129   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -0.119  -0.359   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      -5.440   1.181   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       1.228  -7.289   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       1.228  -5.749   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.119  -4.979   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -0.119  -3.439   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.228  -2.669   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.563  -3.439   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       2.563  -4.979   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       3.882  -5.749   0.000  0.00  0.00           O+0
HETATM   33  O   UNK     0      -0.104   2.669   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.228   3.439   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.563   2.669   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       3.898   3.439   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       5.230   2.669   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.230   1.129   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       6.564   0.359   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       2.563   1.129   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0       3.898   0.359   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       3.898  -1.181   0.000  0.00  0.00           O+0
HETATM   43  C   UNK     0       2.789  -1.874   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0       4.123  -2.644   0.000  0.00  0.00           C+0
HETATM   45  O   UNK     0       2.789  -0.334   0.000  0.00  0.00           O+0
HETATM   46  C   UNK     0       4.123  -4.184   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0       5.456  -4.954   0.000  0.00  0.00           C+0
HETATM   48  C   UNK     0       6.785  -4.184   0.000  0.00  0.00           C+0
HETATM   49  C   UNK     0       6.785  -2.644   0.000  0.00  0.00           C+0
HETATM   50  C   UNK     0       5.456  -1.876   0.000  0.00  0.00           C+0
HETATM   51  O   UNK     0       5.456  -6.494   0.000  0.00  0.00           O+0
HETATM   52  O   UNK     0       8.120  -4.954   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0       8.120  -1.874   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4                                                            
CONECT    6    7                                                            
CONECT    7    6    8   18                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   24                                                  
CONECT   10    9   11   19                                                  
CONECT   11   10   22   12                                                  
CONECT   12    2   11   13                                                  
CONECT   13   12   14   33                                                  
CONECT   14    4   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   34                                                  
CONECT   17   16                                                            
CONECT   18    7   19                                                       
CONECT   19   10   18   20                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   28                                                  
CONECT   22   11   21   23                                                  
CONECT   23   22   43                                                       
CONECT   24    9                                                            
CONECT   25   26                                                            
CONECT   26   25   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   21   27   29                                                  
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   26   30   32                                                  
CONECT   32   31                                                            
CONECT   33   13   34                                                       
CONECT   34   16   33   35                                                  
CONECT   35   34   36   40                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38                                                       
CONECT   38   37   39   41                                                  
CONECT   39   38                                                            
CONECT   40   35   41                                                       
CONECT   41   38   40   42                                                  
CONECT   42   41                                                            
CONECT   43   23   44   45                                                  
CONECT   44   43   46   50                                                  
CONECT   45   43                                                            
CONECT   46   44   47                                                       
CONECT   47   46   48   51                                                  
CONECT   48   47   49   52                                                  
CONECT   49   48   50   53                                                  
CONECT   50   44   49                                                       
CONECT   51   47                                                            
CONECT   52   48                                                            
CONECT   53   49                                                            
MASTER        0    0    0    0    0    0    0    0   53    0  118    0
END

COMPND    HMDB0037965
HETATM    1  O1  UNL     1      -1.251   0.594   2.259  1.00  0.00           O  
HETATM    2  C1  UNL     1      -1.887   0.851   1.216  1.00  0.00           C  
HETATM    3  O2  UNL     1      -1.772   0.039   0.115  1.00  0.00           O  
HETATM    4  C2  UNL     1      -0.957  -1.132   0.074  1.00  0.00           C  
HETATM    5  C3  UNL     1      -1.682  -2.301  -0.477  1.00  0.00           C  
HETATM    6  C4  UNL     1      -2.901  -2.699   0.295  1.00  0.00           C  
HETATM    7  C5  UNL     1      -3.110  -2.375   1.610  1.00  0.00           C  
HETATM    8  C6  UNL     1      -4.281  -2.769   2.274  1.00  0.00           C  
HETATM    9  C7  UNL     1      -5.249  -3.492   1.623  1.00  0.00           C  
HETATM   10  O3  UNL     1      -6.407  -3.874   2.306  1.00  0.00           O  
HETATM   11  C8  UNL     1      -5.047  -3.825   0.289  1.00  0.00           C  
HETATM   12  O4  UNL     1      -6.052  -4.556  -0.328  1.00  0.00           O  
HETATM   13  C9  UNL     1      -3.887  -3.424  -0.338  1.00  0.00           C  
HETATM   14  O5  UNL     1      -2.127  -2.024  -1.769  1.00  0.00           O  
HETATM   15  C10 UNL     1      -1.494  -1.190  -2.636  1.00  0.00           C  
HETATM   16  C11 UNL     1      -2.002  -1.011  -3.904  1.00  0.00           C  
HETATM   17  C12 UNL     1      -1.389  -0.171  -4.820  1.00  0.00           C  
HETATM   18  O6  UNL     1      -1.870   0.035  -6.103  1.00  0.00           O  
HETATM   19  C13 UNL     1      -0.245   0.484  -4.413  1.00  0.00           C  
HETATM   20  C14 UNL     1       0.266   0.307  -3.144  1.00  0.00           C  
HETATM   21  O7  UNL     1       1.425   0.979  -2.753  1.00  0.00           O  
HETATM   22  C15 UNL     1      -0.329  -0.521  -2.229  1.00  0.00           C  
HETATM   23  C16 UNL     1       0.182  -0.749  -0.845  1.00  0.00           C  
HETATM   24  C17 UNL     1       1.403  -1.526  -0.787  1.00  0.00           C  
HETATM   25  C18 UNL     1       1.608  -2.712  -1.501  1.00  0.00           C  
HETATM   26  O8  UNL     1       0.653  -3.185  -2.365  1.00  0.00           O  
HETATM   27  C19 UNL     1       2.772  -3.454  -1.378  1.00  0.00           C  
HETATM   28  C20 UNL     1       3.757  -3.013  -0.531  1.00  0.00           C  
HETATM   29  O9  UNL     1       4.920  -3.741  -0.399  1.00  0.00           O  
HETATM   30  C21 UNL     1       3.563  -1.842   0.177  1.00  0.00           C  
HETATM   31  C22 UNL     1       2.422  -1.084   0.079  1.00  0.00           C  
HETATM   32  O10 UNL     1       2.238   0.083   0.790  1.00  0.00           O  
HETATM   33  C23 UNL     1       3.074   0.433   1.842  1.00  0.00           C  
HETATM   34  C24 UNL     1       3.860   1.658   1.491  1.00  0.00           C  
HETATM   35  C25 UNL     1       4.033   2.662   2.429  1.00  0.00           C  
HETATM   36  C26 UNL     1       4.752   3.801   2.120  1.00  0.00           C  
HETATM   37  C27 UNL     1       5.306   3.947   0.864  1.00  0.00           C  
HETATM   38  O11 UNL     1       6.043   5.069   0.483  1.00  0.00           O  
HETATM   39  C28 UNL     1       5.120   2.933  -0.054  1.00  0.00           C  
HETATM   40  O12 UNL     1       5.674   3.073  -1.319  1.00  0.00           O  
HETATM   41  C29 UNL     1       4.406   1.791   0.238  1.00  0.00           C  
HETATM   42  C30 UNL     1       4.022  -0.640   2.248  1.00  0.00           C  
HETATM   43  O13 UNL     1       5.045  -0.043   3.015  1.00  0.00           O  
HETATM   44  C31 UNL     1       4.645  -1.378   1.096  1.00  0.00           C  
HETATM   45  C32 UNL     1      -2.763   2.034   1.169  1.00  0.00           C  
HETATM   46  C33 UNL     1      -2.841   2.831   2.285  1.00  0.00           C  
HETATM   47  C34 UNL     1      -3.669   3.951   2.267  1.00  0.00           C  
HETATM   48  O14 UNL     1      -3.778   4.787   3.375  1.00  0.00           O  
HETATM   49  C35 UNL     1      -4.374   4.208   1.121  1.00  0.00           C  
HETATM   50  O15 UNL     1      -5.212   5.305   1.041  1.00  0.00           O  
HETATM   51  C36 UNL     1      -4.302   3.407  -0.015  1.00  0.00           C  
HETATM   52  O16 UNL     1      -5.042   3.710  -1.161  1.00  0.00           O  
HETATM   53  C37 UNL     1      -3.486   2.312   0.019  1.00  0.00           C  
HETATM   54  H1  UNL     1      -0.490  -1.368   1.045  1.00  0.00           H  
HETATM   55  H2  UNL     1      -1.007  -3.181  -0.389  1.00  0.00           H  
HETATM   56  H3  UNL     1      -2.386  -1.830   2.149  1.00  0.00           H  
HETATM   57  H4  UNL     1      -4.414  -2.498   3.310  1.00  0.00           H  
HETATM   58  H5  UNL     1      -7.124  -4.399   1.862  1.00  0.00           H  
HETATM   59  H6  UNL     1      -5.879  -4.791  -1.316  1.00  0.00           H  
HETATM   60  H7  UNL     1      -3.758  -3.696  -1.368  1.00  0.00           H  
HETATM   61  H8  UNL     1      -2.902  -1.517  -4.245  1.00  0.00           H  
HETATM   62  H9  UNL     1      -1.525  -0.595  -6.838  1.00  0.00           H  
HETATM   63  H10 UNL     1       0.259   1.146  -5.099  1.00  0.00           H  
HETATM   64  H11 UNL     1       1.906   1.606  -3.395  1.00  0.00           H  
HETATM   65  H12 UNL     1       0.477   0.349  -0.541  1.00  0.00           H  
HETATM   66  H13 UNL     1       0.783  -4.019  -2.879  1.00  0.00           H  
HETATM   67  H14 UNL     1       2.888  -4.372  -1.952  1.00  0.00           H  
HETATM   68  H15 UNL     1       5.058  -4.587  -0.912  1.00  0.00           H  
HETATM   69  H16 UNL     1       2.425   0.649   2.729  1.00  0.00           H  
HETATM   70  H17 UNL     1       3.595   2.547   3.423  1.00  0.00           H  
HETATM   71  H18 UNL     1       4.887   4.585   2.857  1.00  0.00           H  
HETATM   72  H19 UNL     1       6.208   5.838   1.116  1.00  0.00           H  
HETATM   73  H20 UNL     1       5.560   2.343  -2.033  1.00  0.00           H  
HETATM   74  H21 UNL     1       4.259   1.002  -0.476  1.00  0.00           H  
HETATM   75  H22 UNL     1       3.491  -1.386   2.896  1.00  0.00           H  
HETATM   76  H23 UNL     1       5.272  -0.649   3.750  1.00  0.00           H  
HETATM   77  H24 UNL     1       5.114  -2.297   1.515  1.00  0.00           H  
HETATM   78  H25 UNL     1       5.417  -0.794   0.594  1.00  0.00           H  
HETATM   79  H26 UNL     1      -2.277   2.610   3.176  1.00  0.00           H  
HETATM   80  H27 UNL     1      -3.264   4.604   4.213  1.00  0.00           H  
HETATM   81  H28 UNL     1      -5.341   5.959   1.816  1.00  0.00           H  
HETATM   82  H29 UNL     1      -5.625   4.524  -1.135  1.00  0.00           H  
HETATM   83  H30 UNL     1      -3.390   1.664  -0.814  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   45
CONECT    3    4
CONECT    4    5   23   54
CONECT    5    6   14   55
CONECT    6    7    7   13
CONECT    7    8   56
CONECT    8    9    9   57
CONECT    9   10   11
CONECT   10   58
CONECT   11   12   13   13
CONECT   12   59
CONECT   13   60
CONECT   14   15
CONECT   15   16   16   22
CONECT   16   17   61
CONECT   17   18   19   19
CONECT   18   62
CONECT   19   20   63
CONECT   20   21   22   22
CONECT   21   64
CONECT   22   23
CONECT   23   24   65
CONECT   24   25   25   31
CONECT   25   26   27
CONECT   26   66
CONECT   27   28   28   67
CONECT   28   29   30
CONECT   29   68
CONECT   30   31   31   44
CONECT   31   32
CONECT   32   33
CONECT   33   34   42   69
CONECT   34   35   35   41
CONECT   35   36   70
CONECT   36   37   37   71
CONECT   37   38   39
CONECT   38   72
CONECT   39   40   41   41
CONECT   40   73
CONECT   41   74
CONECT   42   43   44   75
CONECT   43   76
CONECT   44   77   78
CONECT   45   46   46   53
CONECT   46   47   79
CONECT   47   48   49   49
CONECT   48   80
CONECT   49   50   51
CONECT   50   81
CONECT   51   52   53   53
CONECT   52   82
CONECT   53   83
END

HMDB0037965
     RDKit          3D
ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate
 83 89  0  0  0  0  0  0  0  0999 V2000
   -1.2514    0.5945    2.2595 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8868    0.8514    1.2156 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7722    0.0386    0.1147 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9566   -1.1318    0.0739 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6825   -2.3012   -0.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9011   -2.6991    0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1103   -2.3753    1.6097 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2807   -2.7692    2.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2493   -3.4917    1.6226 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4069   -3.8739    2.3064 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0468   -3.8254    0.2893 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0520   -4.5560   -0.3281 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8866   -3.4242   -0.3380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1275   -2.0240   -1.7685 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4937   -1.1897   -2.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0018   -1.0111   -3.9040 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3888   -0.1705   -4.8202 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8696    0.0347   -6.1035 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2450    0.4836   -4.4131 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2661    0.3069   -3.1444 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4248    0.9790   -2.7530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3294   -0.5207   -2.2286 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1821   -0.7491   -0.8454 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4029   -1.5261   -0.7866 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6085   -2.7117   -1.5007 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6532   -3.1854   -2.3649 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7724   -3.4543   -1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7567   -3.0130   -0.5313 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9202   -3.7406   -0.3993 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5631   -1.8419    0.1769 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4220   -1.0837    0.0792 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2377    0.0834    0.7897 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0739    0.4331    1.8419 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8600    1.6582    1.4914 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0334    2.6617    2.4289 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7520    3.8010    2.1198 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3058    3.9473    0.8645 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0427    5.0689    0.4827 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1196    2.9334   -0.0541 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6737    3.0726   -1.3187 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.4060    1.7912    0.2380 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0221   -0.6400    2.2484 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0449   -0.0428    3.0150 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6453   -1.3783    1.0964 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7633    2.0335    1.1690 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8412    2.8307    2.2854 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6686    3.9514    2.2669 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7779    4.7871    3.3749 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3742    4.2081    1.1215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2124    5.3051    1.0413 O   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3025    3.4070   -0.0151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0424    3.7104   -1.1612 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4864    2.3119    0.0193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4902   -1.3676    1.0449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0068   -3.1813   -0.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3860   -1.8299    2.1493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4143   -2.4978    3.3097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1239   -4.3991    1.8619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8789   -4.7913   -1.3159 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7578   -3.6963   -1.3677 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9022   -1.5173   -4.2451 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5251   -0.5954   -6.8377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2594    1.1460   -5.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9064    1.6055   -3.3946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4772    0.3491   -0.5411 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7826   -4.0194   -2.8786 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8880   -4.3725   -1.9520 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0576   -4.5871   -0.9119 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4248    0.6492    2.7289 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5954    2.5468    3.4234 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8872    4.5851    2.8571 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2079    5.8377    1.1158 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5600    2.3430   -2.0335 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2594    1.0025   -0.4761 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -1.3856    2.8957 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2721   -0.6486    3.7503 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1141   -2.2967    1.5146 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4167   -0.7937    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2768    2.6102    3.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2639    4.6040    4.2128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3408    5.9590    1.8163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6249    4.5239   -1.1350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3899    1.6635   -0.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
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  5 14  1  0
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 15 16  2  0
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 53 83  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
ent-Epicatechin-(4a->8)-ent-epicatechin 3-gallate	Generator
ent-Epicatechin-(4a->8)-ent-epicatechin 3-gallic acid	Generator
ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallic acid	Generator
ent-Epicatechin-(4α->8)-ent-epicatechin 3-gallate	Generator
ent-Epicatechin-(4α->8)-ent-epicatechin 3-gallic acid	Generator
3-Galloylprocyanidin b1	HMDB
Procyanidin dimer b1 3-O-gallate	HMDB
2-(3,4-Dihydroxyphenyl)-4-[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-trihydroxybenzoic acid	HMDB

Chemical Formula

C₃₇H₃₀O₁₆

Average Molecular Weight

730.6245

Monoisotopic Molecular Weight

730.153384912

IUPAC Name

2-(3,4-dihydroxyphenyl)-4-[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

2-(3,4-dihydroxyphenyl)-4-[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

Not Available

SMILES

OC1CC2=C(O)C=C(O)C(C3C(OC(=O)C4=CC(O)=C(O)C(O)=C4)C(OC4=CC(O)=CC(O)=C34)C3=CC=C(O)C(O)=C3)=C2OC1C1=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

InChI Key

BXWABJPTCUDBMM-UHFFFAOYSA-N

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

Not Available

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.087 g/L	ALOGPS
logP	3.33	ALOGPS
logP	4.7	ChemAxon
logS	-3.9	ALOGPS
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	69.9 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	263.115	31661259
DarkChem	[M-H]-	249.983	31661259
DeepCCS	[M-2H]-	286.967	30932474
DeepCCS	[M+Na]+	260.742	30932474
AllCCS	[M+H]+	261.8	32859911
AllCCS	[M+H-H2O]+	261.0	32859911
AllCCS	[M+NH4]+	262.4	32859911
AllCCS	[M+Na]+	262.6	32859911
AllCCS	[M-H]-	254.3	32859911
AllCCS	[M+Na-2H]-	257.1	32859911
AllCCS	[M+HCOO]-	260.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	3.09 minutes	32390414
Predicted by Siyang on May 30, 2022	12.0896 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	4.22 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	122.1 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1587.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	128.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	113.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	106.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	106.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	738.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	464.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	884.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	734.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	409.3 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1457.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	259.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	323.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	451.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	493.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	528.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate	OC1CC2=C(O)C=C(O)C(C3C(OC(=O)C4=CC(O)=C(O)C(O)=C4)C(OC4=CC(O)=CC(O)=C34)C3=CC=C(O)C(O)=C3)=C2OC1C1=CC=C(O)C(O)=C1	9185.7	Standard polar	33892256
ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate	OC1CC2=C(O)C=C(O)C(C3C(OC(=O)C4=CC(O)=C(O)C(O)=C4)C(OC4=CC(O)=CC(O)=C34)C3=CC=C(O)C(O)=C3)=C2OC1C1=CC=C(O)C(O)=C1	5957.1	Standard non polar	33892256
ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate	OC1CC2=C(O)C=C(O)C(C3C(OC(=O)C4=CC(O)=C(O)C(O)=C4)C(OC4=CC(O)=CC(O)=C34)C3=CC=C(O)C(O)=C3)=C2OC1C1=CC=C(O)C(O)=C1	7521.5	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0w4i-0900030100-12cb7c59426319aa7026	2017-11-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_1_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_1_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_1_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_1_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_1_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_1_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_1_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_1_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_1_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_1_10) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_1_11) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_2_1) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_2_2) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_2_3) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_2_4) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_2_5) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_2_6) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_2_7) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_2_8) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_2_9) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_2_10) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_2_11) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_2_12) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate GC-MS (TMS_2_13) - 70eV, Positive	Not Available	2021-10-18	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 10V, Positive-QTOF	splash10-0in9-0610390800-81623953ceca8f3ecad3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 20V, Positive-QTOF	splash10-0pb9-0953821100-fcafbea2f9d2cea070e6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 40V, Positive-QTOF	splash10-0udl-0972010000-8a5bb4d6b0534651ba29	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 10V, Positive-QTOF	splash10-0in9-0610390800-81623953ceca8f3ecad3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 20V, Positive-QTOF	splash10-0pb9-0953821100-fcafbea2f9d2cea070e6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 40V, Positive-QTOF	splash10-0udl-0972010000-8a5bb4d6b0534651ba29	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 10V, Positive-QTOF	splash10-0in9-0610390800-81623953ceca8f3ecad3	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 20V, Positive-QTOF	splash10-0pb9-0953821100-fcafbea2f9d2cea070e6	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 40V, Positive-QTOF	splash10-0udl-0972010000-8a5bb4d6b0534651ba29	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 10V, Negative-QTOF	splash10-004i-0400020900-15c1d892670c625835a7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 20V, Negative-QTOF	splash10-0fbi-0920012100-f4b930a3016c013db44a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 40V, Negative-QTOF	splash10-00or-0911000000-9862fd11a465aba5dcb1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 10V, Negative-QTOF	splash10-004i-0400020900-15c1d892670c625835a7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 20V, Negative-QTOF	splash10-0fbi-0920012100-f4b930a3016c013db44a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 40V, Negative-QTOF	splash10-00or-0911000000-9862fd11a465aba5dcb1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 10V, Negative-QTOF	splash10-004i-0400020900-15c1d892670c625835a7	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 20V, Negative-QTOF	splash10-0fbi-0920012100-f4b930a3016c013db44a	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 40V, Negative-QTOF	splash10-00or-0911000000-9862fd11a465aba5dcb1	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 10V, Positive-QTOF	splash10-01q9-0000055900-69200b3149e105acda09	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 20V, Positive-QTOF	splash10-03e9-0270296600-9e0babdd1c35a0ce1e26	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 40V, Positive-QTOF	splash10-00fr-0710429300-7da74180b8fdfb5ef0ae	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 10V, Negative-QTOF	splash10-004i-0000000900-5e3d27c2e8bbd5f10b36	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 20V, Negative-QTOF	splash10-01t9-0200219800-b4f0b4cc80916da286df	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate 40V, Negative-QTOF	splash10-004u-2310139200-40fe53c1160e4950297c	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

172

FooDB ID

FDB021168

KNApSAcK ID

Not Available

Chemspider ID

35014493

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12795889

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Enzymes

Enzyme Details

1. Liver carboxylesterase 1

General function:: Lipid transport and metabolism
Specific function:: Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl-CoA ester. Hydrolyzes the methyl ester group of cocaine to form benzoylecgonine. Catalyzes the transesterification of cocaine to form cocaethylene. Displays fatty acid ethyl ester synthase activity, catalyzing the ethyl esterification of oleic acid to ethyloleate.
Gene Name:: CES1
Uniprot ID:: P23141
Molecular weight:: 62520.62

Reactions

ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate → ent-Epicatechin(4alpha->8)catechin	details
ent-Epicatechin-(4alpha->8)-ent-epicatechin 3,3'-digallate → ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate	details

Showing metabocard for ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate (HMDB0037965)

MOL for HMDB0037965 (ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate)

3D MOL for HMDB0037965 (ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate)

3D SDF for HMDB0037965 (ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate)

3D-SDF for HMDB0037965 (ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate)

PDB for HMDB0037965 (ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate)

3D PDB for HMDB0037965 (ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate)

SMILES for HMDB0037965 (ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate)

INCHI for HMDB0037965 (ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate)

Structure for HMDB0037965 (ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate)

3D Structure for HMDB0037965 (ent-Epicatechin-(4alpha->8)-ent-epicatechin 3-gallate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

Reactions