NP-MRD: Showing NP-Card for Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallate (NP0335580)

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Record Information

Version

2.0

Created at

2024-09-11 02:15:36 UTC

Updated at

2024-09-11 02:15:36 UTC

NP-MRD ID

NP0335580

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallate

Description

Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallate 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''. Based on a literature review very few articles have been published on Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallate.

Structure

MOL SDF PDB SMILES InChI


  Mrv2104 05262304472D          

 65 72  0  0  0  0            999 V2000
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M  END


  Mrv2104 05262304472D          

 65 72  0  0  0  0            999 V2000
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M  END
> <DATABASE_ID>
NP0335580

> <DATABASE_NAME>
NP-MRD

> <SMILES>
OC1=CC2=C([C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C2=CC(O)=C(O)C(O)=C2)C2=C(O)C3=C(O[C@@H]([C@@H](C3)OC(=O)C3=CC(O)=C(O)C(O)=C3)C3=CC=C(O)C(O)=C3)C=C2O)C(O)=C1

> <INCHI_IDENTIFIER>
InChI=1/C44H34O21/c45-18-10-22(48)33-31(11-18)63-41(15-4-24(50)37(57)25(51)5-15)42(65-44(61)17-8-28(54)39(59)29(55)9-17)35(33)34-23(49)13-30-19(36(34)56)12-32(40(62-30)14-1-2-20(46)21(47)3-14)64-43(60)16-6-26(52)38(58)27(53)7-16/h1-11,13,32,35,40-42,45-59H,12H2/t32-,35-,40-,41-,42-/s2

> <INCHI_KEY>
KRHJUZZZEMFSIW-LHHFYSJSNA-N

> <FORMULA>
C44H34O21

> <MOLECULAR_WEIGHT>
898.735

> <EXACT_MASS>
898.159258115

> <JCHEM_ACCEPTOR_COUNT>
19

> <JCHEM_ATOM_COUNT>
99

> <JCHEM_AVERAGE_POLARIZABILITY>
85.91889601931314

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
15

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,3R)-6-[(2R,3R,4S)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

> <JCHEM_LOGP>
5.981387459333333

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.320258448291035

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.771058805508238

> <JCHEM_PKA_STRONGEST_BASIC>
-5.548931352793803

> <JCHEM_POLAR_SURFACE_AREA>
374.51000000000005

> <JCHEM_REFRACTIVITY>
220.01830000000007

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2R,3R)-6-[(2R,3R,4S)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 26-MAY-23   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAY-23         0                                  
HETATM    1  C   UNK     0      -8.518  -0.346   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.851  -1.116   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -9.851  -2.657   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.517  -3.426   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -7.184  -2.656   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -7.184  -1.116   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -5.850  -0.346   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -5.850  -3.426   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.517  -2.656   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.517  -1.116   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.183  -0.346   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.849   1.964   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.183   1.194   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.849  -1.116   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.516  -0.346   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.516   1.194   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0     -11.185  -0.347   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -1.133  -4.263   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       0.818   1.964   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       0.818  -1.116   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      -8.517  -4.966   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      -4.565  -9.646   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -4.565  -8.106   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      -5.899  -7.336   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      -7.233  -8.106   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -7.233  -9.646   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -5.899 -10.416   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -5.899 -11.956   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      -8.567 -10.416   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -8.567 -11.956   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -7.233 -12.726   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -7.233 -14.266   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.899 -16.576   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -5.899 -15.036   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -8.567 -15.036   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -8.567 -16.576   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -7.233 -17.346   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -3.232  -7.336   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      -7.233 -18.886   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -9.900 -17.346   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -8.567  -7.336   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0     -12.568 -12.726   0.000  0.00  0.00           C+0
HETATM   43  C   UNK     0     -12.568 -11.186   0.000  0.00  0.00           C+0
HETATM   44  C   UNK     0     -13.901 -10.416   0.000  0.00  0.00           C+0
HETATM   45  C   UNK     0     -15.235 -11.186   0.000  0.00  0.00           C+0
HETATM   46  C   UNK     0     -15.235 -12.726   0.000  0.00  0.00           C+0
HETATM   47  C   UNK     0     -13.901 -13.496   0.000  0.00  0.00           C+0
HETATM   48  O   UNK     0     -16.569 -10.416   0.000  0.00  0.00           O+0
HETATM   49  O   UNK     0     -16.569 -13.496   0.000  0.00  0.00           O+0
HETATM   50  O   UNK     0     -13.901  -8.876   0.000  0.00  0.00           O+0
HETATM   51  C   UNK     0     -11.234 -13.496   0.000  0.00  0.00           C+0
HETATM   52  O   UNK     0     -11.234 -15.036   0.000  0.00  0.00           O+0
HETATM   53  O   UNK     0      -9.900 -12.726   0.000  0.00  0.00           O+0
HETATM   54  C   UNK     0       0.200  -6.573   0.000  0.00  0.00           C+0
HETATM   55  C   UNK     0      -1.133  -7.343   0.000  0.00  0.00           C+0
HETATM   56  C   UNK     0      -1.133  -8.883   0.000  0.00  0.00           C+0
HETATM   57  C   UNK     0       0.200  -9.653   0.000  0.00  0.00           C+0
HETATM   58  C   UNK     0       1.534  -8.883   0.000  0.00  0.00           C+0
HETATM   59  C   UNK     0       1.534  -7.343   0.000  0.00  0.00           C+0
HETATM   60  O   UNK     0       0.200 -11.193   0.000  0.00  0.00           O+0
HETATM   61  O   UNK     0       2.868  -9.653   0.000  0.00  0.00           O+0
HETATM   62  O   UNK     0      -2.467  -9.653   0.000  0.00  0.00           O+0
HETATM   63  C   UNK     0       0.200  -5.033   0.000  0.00  0.00           C+0
HETATM   64  O   UNK     0       1.534  -4.263   0.000  0.00  0.00           O+0
HETATM   65  O   UNK     0      -1.849   3.504   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   17                                                  
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   24                                                  
CONECT    9    8   10   18                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16   65                                                  
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16   20                                                  
CONECT   16   12   15   19                                                  
CONECT   17    2                                                            
CONECT   18    9   63                                                       
CONECT   19   16                                                            
CONECT   20   15                                                            
CONECT   21    4                                                            
CONECT   22   23   27                                                       
CONECT   23   22   24   38                                                  
CONECT   24   23   25    8                                                  
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                                                       
CONECT   34   32   33                                                       
CONECT   35   32   36                                                       
CONECT   36   35   37   40                                                  
CONECT   37   33   36   39                                                  
CONECT   38   23                                                            
CONECT   39   37                                                            
CONECT   40   36                                                            
CONECT   41   25                                                            
CONECT   42   43   47   51                                                  
CONECT   43   42   44                                                       
CONECT   44   43   45   50                                                  
CONECT   45   44   46   48                                                  
CONECT   46   45   47   49                                                  
CONECT   47   46   42                                                       
CONECT   48   45                                                            
CONECT   49   46                                                            
CONECT   50   44                                                            
CONECT   51   42   52   53                                                  
CONECT   52   51                                                            
CONECT   53   30   51                                                       
CONECT   54   55   59   63                                                  
CONECT   55   54   56                                                       
CONECT   56   55   57   62                                                  
CONECT   57   56   58   60                                                  
CONECT   58   57   59   61                                                  
CONECT   59   58   54                                                       
CONECT   60   57                                                            
CONECT   61   58                                                            
CONECT   62   56                                                            
CONECT   63   54   64   18                                                  
CONECT   64   63                                                            
CONECT   65   12                                                            
MASTER        0    0    0    0    0    0    0    0   65    0  144    0
END

View in JSmol

Synonyms

Value	Source
Epigallocatechin-(4b->6)-epicatechin 3,3'-digallate	Generator
Epigallocatechin-(4b->6)-epicatechin 3,3'-digallic acid	Generator
Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallic acid	Generator
Epigallocatechin-(4β->6)-epicatechin 3,3'-digallate	Generator
Epigallocatechin-(4β->6)-epicatechin 3,3'-digallic acid	Generator

Chemical Formula

C₄₄H₃₄O₂₁

Average Mass

898.7350 Da

Monoisotopic Mass

898.15926 Da

IUPAC Name

(2R,3R)-6-[(2R,3R,4S)-5,7-dihydroxy-3-(3,4,5-trihydroxybenzoyloxy)-2-(3,4,5-trihydroxyphenyl)-3,4-dihydro-2H-1-benzopyran-4-yl]-2-(3,4-dihydroxyphenyl)-5,7-dihydroxy-3,4-dihydro-2H-1-benzopyran-3-yl 3,4,5-trihydroxybenzoate

Traditional Name

CAS Registry Number

Not Available

SMILES

OC1=CC2=C([C@@H]([C@@H](OC(=O)C3=CC(O)=C(O)C(O)=C3)[C@H](O2)C2=CC(O)=C(O)C(O)=C2)C2=C(O)C3=C(O[C@@H]([C@@H](C3)OC(=O)C3=CC(O)=C(O)C(O)=C3)C3=CC=C(O)C(O)=C3)C=C2O)C(O)=C1

InChI Identifier

InChI=1/C44H34O21/c45-18-10-22(48)33-31(11-18)63-41(15-4-24(50)37(57)25(51)5-15)42(65-44(61)17-8-28(54)39(59)29(55)9-17)35(33)34-23(49)13-30-19(36(34)56)12-32(40(62-30)14-1-2-20(46)21(47)3-14)64-43(60)16-6-26(52)38(58)27(53)7-16/h1-11,13,32,35,40-42,45-59H,12H2/t32-,35-,40-,41-,42-/s2

InChI Key

KRHJUZZZEMFSIW-LHHFYSJSNA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

Chemical Taxonomy

Description

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	5.98	ChemAxon
pKa (Strongest Acidic)	7.77	ChemAxon
pKa (Strongest Basic)	-5.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	19	ChemAxon
Hydrogen Donor Count	15	ChemAxon
Polar Surface Area	374.51 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	220.02 m³·mol⁻¹	ChemAxon
Polarizability	85.92 Å³	ChemAxon
Number of Rings	8	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00009230

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallate (NP0335580)

MOL for NP0335580 (Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallate)

3D MOL for NP0335580 (Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallate)

3D SDF for NP0335580 (Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallate)

3D-SDF for NP0335580 (Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallate)

PDB for NP0335580 (Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallate)

3D PDB for NP0335580 (Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallate)

SMILES for NP0335580 (Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallate)

INCHI for NP0335580 (Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallate)

Structure for NP0335580 (Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallate)

3D Structure for NP0335580 (Epigallocatechin-(4beta->6)-epicatechin 3,3'-digallate)