NP-MRD: Showing NP-Card for Epigallocatechin 3,3',-di-O-gallate (NP0056122)

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Record Information

Version

2.0

Created at

2022-04-28 01:59:46 UTC

Updated at

2022-04-28 01:59:46 UTC

NP-MRD ID

NP0056122

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Epigallocatechin 3,3',-di-O-gallate

Description

(-)-Epigallocatechin 3,3'-di-gallate, also known as 3,3'-di-O-galloylepigallocatechin, belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin (-)-Epigallocatechin 3,3'-di-gallate is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (-)-Epigallocatechin 3,3'-di-gallate has been detected, but not quantified in, tea. Epigallocatechin 3,3',-di-O-gallate is found in Camellia sinensis and Phedimus stoloniferus. This could make (-)-epigallocatechin 3,3'-di-gallate a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv0541 02241211102D          

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M  END

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  Mrv0541 02241211102D          

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   -2.3205    1.3481    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1456    2.7770    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3205    4.2059    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.1545    2.7770    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670    3.4915    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5670    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  7  6  1  0  0  0  0
  6  5  2  0  0  0  0
  5  8  1  0  0  0  0
  7 10  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  6  0  0  0
 13 11  2  0  0  0  0
 11 14  1  0  0  0  0
 12 13  1  0  0  0  0
 12 16  2  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 18  1  0  0  0  0
  4 19  1  0  0  0  0
 12 44  1  0  0  0  0
  9 31  1  6  0  0  0
 20 21  2  0  0  0  0
 20 25  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 22 26  1  0  0  0  0
 23 27  1  0  0  0  0
 24 28  1  0  0  0  0
 20 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 15 32  1  0  0  0  0
 33 34  2  0  0  0  0
 33 38  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 36 37  1  0  0  0  0
 37 38  2  0  0  0  0
 35 39  1  0  0  0  0
 36 40  1  0  0  0  0
 37 41  1  0  0  0  0
 33 42  1  0  0  0  0
 42 43  2  0  0  0  0
 42 44  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056122

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C29H22O15/c30-13-7-15(31)14-9-23(44-29(41)12-4-18(34)25(38)19(35)5-12)27(42-21(14)8-13)10-1-20(36)26(39)22(6-10)43-28(40)11-2-16(32)24(37)17(33)3-11/h1-8,23,27,30-39H,9H2/t23-,27-/m1/s1

> <INCHI_KEY>
LGGSDHMXURUIDJ-YIXXDRMTSA-N

> <FORMULA>
C29H22O15

> <MOLECULAR_WEIGHT>
610.476

> <EXACT_MASS>
610.095870034

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_AVERAGE_POLARIZABILITY>
57.74838033514176

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
10

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.12

> <JCHEM_LOGP>
4.780450346666667

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.31610792322014

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.7565176802180105

> <JCHEM_PKA_STRONGEST_BASIC>
-4.669990136244807

> <JCHEM_POLAR_SURFACE_AREA>
264.12999999999994

> <JCHEM_REFRACTIVITY>
147.51000000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.30e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -5.610   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.944  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.944  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.610  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.276  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.276  -0.770   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -2.943   0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.943  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.609  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.609  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.275   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.058   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.275   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.058  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.392   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.392   1.540   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       3.726   2.310   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0      -8.277   0.000   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      -5.610  -4.620   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       1.058  -5.390   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -0.275  -6.160   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.275  -7.700   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       1.058  -8.470   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       2.392  -7.700   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       2.392  -6.160   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      -1.609  -8.470   0.000  0.00  0.00           O+0
HETATM   27  O   UNK     0       1.058 -10.010   0.000  0.00  0.00           O+0
HETATM   28  O   UNK     0       3.726  -8.470   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       1.058  -3.850   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0       2.392  -3.080   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0      -0.275  -3.080   0.000  0.00  0.00           O+0
HETATM   32  O   UNK     0       3.726  -0.770   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -1.252   5.184   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.022   3.850   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -3.562   3.850   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      -4.332   5.184   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -3.562   6.517   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -2.022   6.517   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      -4.332   2.516   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0      -5.872   5.184   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0      -4.332   7.851   0.000  0.00  0.00           O+0
HETATM   42  C   UNK     0       0.288   5.184   0.000  0.00  0.00           C+0
HETATM   43  O   UNK     0       1.058   6.517   0.000  0.00  0.00           O+0
HETATM   44  O   UNK     0       1.058   3.850   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   18                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   19                                                  
CONECT    5    4    6    8                                                  
CONECT    6    1    7    5                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   31                                                  
CONECT   10    7    9   11                                                  
CONECT   11   10   13   14                                                  
CONECT   12   13   16   44                                                  
CONECT   13   11   12                                                       
CONECT   14   11   15                                                       
CONECT   15   14   16   32                                                  
CONECT   16   12   15   17                                                  
CONECT   17   16                                                            
CONECT   18    2                                                            
CONECT   19    4                                                            
CONECT   20   21   25   29                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   26                                                  
CONECT   23   22   24   27                                                  
CONECT   24   23   25   28                                                  
CONECT   25   20   24                                                       
CONECT   26   22                                                            
CONECT   27   23                                                            
CONECT   28   24                                                            
CONECT   29   20   30   31                                                  
CONECT   30   29                                                            
CONECT   31    9   29                                                       
CONECT   32   15                                                            
CONECT   33   34   38   42                                                  
CONECT   34   33   35                                                       
CONECT   35   34   36   39                                                  
CONECT   36   35   37   40                                                  
CONECT   37   36   38   41                                                  
CONECT   38   33   37                                                       
CONECT   39   35                                                            
CONECT   40   36                                                            
CONECT   41   37                                                            
CONECT   42   33   43   44                                                  
CONECT   43   42                                                            
CONECT   44   12   42                                                       
MASTER        0    0    0    0    0    0    0    0   44    0   96    0
END

View in JSmol

Synonyms

Value	Source
(-)-Epigallocatechin 3,3'-di-gallic acid	Generator
(-)-Epigallocatechin 3,3'-di-O-gallate	HMDB
3,3'-Di-O-galloylepigallocatechin	HMDB
Epigallocatechin 3,3'-di-gallate	HMDB
Epigallocatechin 3,3'-di-O-gallate	HMDB
Epigallocatechin 3,3',-di-O-gallic acid	Generator
Epigallocatechin 3,3'-digallic acid	Generator

Chemical Formula

C₂₉H₂₂O₁₅

Average Mass

610.4760 Da

Monoisotopic Mass

610.09587 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C29H22O15/c30-13-7-15(31)14-9-23(44-29(41)12-4-18(34)25(38)19(35)5-12)27(42-21(14)8-13)10-1-20(36)26(39)22(6-10)43-28(40)11-2-16(32)24(37)17(33)3-11/h1-8,23,27,30-39H,9H2/t23-,27-/m1/s1

InChI Key

LGGSDHMXURUIDJ-YIXXDRMTSA-N

Experimental Spectra

Not Available

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Camellia sinensis	Plant	KNApSAcK
Phedimus stoloniferus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavans

Direct Parent

Catechin gallates

Alternative Parents

Substituents

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

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020126 )

Physical Properties

State

Not Available

Experimental Properties

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

Predicted Properties

Property	Value	Source
logP	3.12	ALOGPS
logP	4.78	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Acidic)	7.76	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	10	ChemAxon
Polar Surface Area	264.13 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	147.51 m³·mol⁻¹	ChemAxon
Polarizability	57.75 Å³	ChemAxon
Number of Rings	5	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

HMDB0039297

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB018843

KNApSAcK ID

C00008888

Chemspider ID

410664

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

467300

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Epigallocatechin 3,3',-di-O-gallate (NP0056122)

MOL for NP0056122 (Epigallocatechin 3,3',-di-O-gallate)

3D MOL for NP0056122 (Epigallocatechin 3,3',-di-O-gallate)

3D SDF for NP0056122 (Epigallocatechin 3,3',-di-O-gallate)

3D-SDF for NP0056122 (Epigallocatechin 3,3',-di-O-gallate)

PDB for NP0056122 (Epigallocatechin 3,3',-di-O-gallate)

3D PDB for NP0056122 (Epigallocatechin 3,3',-di-O-gallate)

SMILES for NP0056122 (Epigallocatechin 3,3',-di-O-gallate)

INCHI for NP0056122 (Epigallocatechin 3,3',-di-O-gallate)

Structure for NP0056122 (Epigallocatechin 3,3',-di-O-gallate)

3D Structure for NP0056122 (Epigallocatechin 3,3',-di-O-gallate)