NP-MRD: Showing NP-Card for Catechin 5,3'-di-O-gallate (NP0056114)

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Record Information

Version

2.0

Created at

2022-04-28 01:59:27 UTC

Updated at

2022-04-28 01:59:27 UTC

NP-MRD ID

NP0056114

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Catechin 5,3'-di-O-gallate

Description

Catechin 5,3'-di-o-gallate belongs to the class of organic compounds known as catechin gallates. These are organic compounds containing a gallate moiety glycosidically linked to a catechin. Catechin 5,3'-di-O-gallate is found in Acacia gerrardii , Acacia nilotica and Vachellia nilotica. Based on a literature review very few articles have been published on Catechin 5,3'-di-o-gallate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282203592D          

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M  END

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  Mrv1652304282203592D          

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  4 10  1  0  0  0  0
  9 11  1  1  0  0  0
  8 12  1  6  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 12 17  1  0  0  0  0
 15 18  1  0  0  0  0
 14 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 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
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 22 27  1  0  0  0  0
 26 28  1  0  0  0  0
 25 29  1  0  0  0  0
 24 30  1  0  0  0  0
  3 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
 35 36  1  0  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 38 39  2  0  0  0  0
 34 39  1  0  0  0  0
 38 40  1  0  0  0  0
 37 41  1  0  0  0  0
 36 42  1  0  0  0  0
  1 43  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0056114

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@H]1CC2=C(OC(=O)C3=CC(O)=C(O)C(O)=C3)C=C(O)C=C2O[C@@H]1C1=CC(OC(=O)C2=CC(O)=C(O)C(O)=C2)=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H22O14/c30-14-8-22-15(23(9-14)42-28(39)12-3-17(32)25(37)18(33)4-12)10-21(36)27(41-22)11-1-2-16(31)24(7-11)43-29(40)13-5-19(34)26(38)20(35)6-13/h1-9,21,27,30-38H,10H2/t21-,27+/m0/s1

> <INCHI_KEY>
OVHMMCMRYOPGQY-KDYSTLNUSA-N

> <FORMULA>
C29H22O14

> <MOLECULAR_WEIGHT>
594.481

> <EXACT_MASS>
594.100955388

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
56.35905387335134

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
9

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
3.21

> <JCHEM_LOGP>
4.553716553999999

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.323857862161631

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.748301292814373

> <JCHEM_PKA_STRONGEST_BASIC>
-4.351817355138061

> <JCHEM_POLAR_SURFACE_AREA>
243.89999999999995

> <JCHEM_REFRACTIVITY>
145.5291

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.21e-02 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       8.002   4.620   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.336   3.850   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       8.002   6.160   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668   6.930   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      10.669   9.240   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0       8.002  10.780   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       5.335   9.240   0.000  0.00  0.00           O+0
HETATM   31  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   41  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   42  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   43  O   UNK     0      -2.667   0.000   0.000  0.00  0.00           O+0
CONECT    1    2    6   43                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9    4                                                       
CONECT   11    9                                                            
CONECT   12    8   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   18                                                  
CONECT   16   15   17                                                       
CONECT   17   16   12                                                       
CONECT   18   15                                                            
CONECT   19   14   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   27                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25   30                                                  
CONECT   25   24   26   29                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26   22                                                       
CONECT   28   26                                                            
CONECT   29   25                                                            
CONECT   30   24                                                            
CONECT   31    3   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   39                                                  
CONECT   35   34   36                                                       
CONECT   36   35   37   42                                                  
CONECT   37   36   38   41                                                  
CONECT   38   37   39   40                                                  
CONECT   39   38   34                                                       
CONECT   40   38                                                            
CONECT   41   37                                                            
CONECT   42   36                                                            
CONECT   43    1                                                            
MASTER        0    0    0    0    0    0    0    0   43    0   94    0
END

View in JSmol

Synonyms

Value	Source
Catechin 5,3'-di-O-gallic acid	Generator

Chemical Formula

C₂₉H₂₂O₁₄

Average Mass

594.4810 Da

Monoisotopic Mass

594.10096 Da

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

O[C@H]1CC2=C(OC(=O)C3=CC(O)=C(O)C(O)=C3)C=C(O)C=C2O[C@@H]1C1=CC(OC(=O)C2=CC(O)=C(O)C(O)=C2)=C(O)C=C1

InChI Identifier

InChI=1S/C29H22O14/c30-14-8-22-15(23(9-14)42-28(39)12-3-17(32)25(37)18(33)4-12)10-21(36)27(41-22)11-1-2-16(31)24(7-11)43-29(40)13-5-19(34)26(38)20(35)6-13/h1-9,21,27,30-38H,10H2/t21-,27+/m0/s1

InChI Key

OVHMMCMRYOPGQY-KDYSTLNUSA-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
Acacia gerrardii	Plant	KNApSAcK
Acacia nilotica	Plant	KNApSAcK
Vachellia nilotica	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
Depside backbone
3-hydroxyflavonoid
4'-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Tannin
Galloyl ester
Gallic acid or derivatives
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Chromane
Benzopyran
Phenol ester
1-benzopyran
Pyrogallol derivative
Benzenetriol
Benzoic acid or derivatives
Phenoxy compound
Benzoyl
Phenol
Alkyl aryl ether
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Monocyclic benzene moiety
Secondary alcohol
Carboxylic acid ester
Ether
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Alcohol
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

Flavans, Flavanols and Leucoanthocyanidins (LMPK12020102 )

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	3.21	ALOGPS
logP	4.55	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	7.75	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	9	ChemAxon
Polar Surface Area	243.9 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	145.53 m³·mol⁻¹	ChemAxon
Polarizability	56.36 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00008878

Chemspider ID

24842560

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15689619

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for Catechin 5,3'-di-O-gallate (NP0056114)

MOL for NP0056114 (Catechin 5,3'-di-O-gallate)

3D MOL for NP0056114 (Catechin 5,3'-di-O-gallate)

3D SDF for NP0056114 (Catechin 5,3'-di-O-gallate)

3D-SDF for NP0056114 (Catechin 5,3'-di-O-gallate)

PDB for NP0056114 (Catechin 5,3'-di-O-gallate)

3D PDB for NP0056114 (Catechin 5,3'-di-O-gallate)

SMILES for NP0056114 (Catechin 5,3'-di-O-gallate)

INCHI for NP0056114 (Catechin 5,3'-di-O-gallate)

Structure for NP0056114 (Catechin 5,3'-di-O-gallate)

3D Structure for NP0056114 (Catechin 5,3'-di-O-gallate)