NP-MRD: Showing NP-Card for 6-galloyl-α-D-glucose + 6-galloyl-β-D-glucose (1:1, mol/mol) (NP0333063)

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Record Information

Version

2.0

Created at

2024-05-04 05:22:44 UTC

Updated at

2025-07-30 22:19:08 UTC

NP-MRD ID

NP0333063

Natural Product DOI

https://doi.org/10.57994/2362

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-galloyl-α-D-glucose + 6-galloyl-β-D-glucose (1:1, mol/mol)

Description

6-galloyl-α-D-glucose + 6-galloyl-β-D-glucose (1:1, mol/mol) was first documented in 2024 (PMID: 38359463).

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241221022D          

 23 24  0  0  1  0            999 V2000
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -2.4750    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5724   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -2.8875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  0  0  0  0
  5  8  1  0  0  0  0
  4  9  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  2  0  0  0  0
 10 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 13  1  6  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 14 19  1  0  0  0  0
 18 20  1  6  0  0  0
 17 21  1  1  0  0  0
 16 22  1  6  0  0  0
 15 23  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0333063

> <DATABASE_NAME>
NP-MRD

> <SMILES>
O[C@@H]1O[C@H](COC(=O)C2=CC(O)=C(O)C(O)=C2)[C@@H](O)[C@H](O)[C@H]1O

> <INCHI_IDENTIFIER>
InChI=1S/C13H16O10/c14-5-1-4(2-6(15)8(5)16)12(20)22-3-7-9(17)10(18)11(19)13(21)23-7/h1-2,7,9-11,13-19,21H,3H2/t7-,9-,10+,11-,13-/m1/s1

> <INCHI_KEY>
VGVDLJNNDOFWKT-JEUROIALSA-N

> <FORMULA>
C13H16O10

> <MOLECULAR_WEIGHT>
332.2601

> <EXACT_MASS>
332.074346732

> <JCHEM_ACCEPTOR_COUNT>
9

> <JCHEM_AVERAGE_POLARIZABILITY>
30.600650613864065

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

> <ALOGPS_LOGP>
-1.29

> <JCHEM_LOGP>
-1.3479353343333333

> <ALOGPS_LOGS>
-1.23

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
10.991189479316796

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.10762061314705

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6490839182932273

> <JCHEM_POLAR_SURFACE_AREA>
177.14

> <JCHEM_REFRACTIVITY>
71.6881

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.94e+01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl 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       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0      -2.667  -4.620   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      -2.667  -7.700   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.667  -9.240   0.000  0.00  0.00           O+0
HETATM   12  O   UNK     0       4.001  -6.930   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335  -4.620   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.002  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       9.336  -5.390   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0       4.001  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    9                                                  
CONECT    5    4    6    8                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    4                                                            
CONECT   10    2   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   19                                                  
CONECT   15   14   16   23                                                  
CONECT   16   15   17   22                                                  
CONECT   17   16   18   21                                                  
CONECT   18   17   19   20                                                  
CONECT   19   18   14                                                       
CONECT   20   18                                                            
CONECT   21   17                                                            
CONECT   22   16                                                            
CONECT   23   15                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   48    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₃H₁₆O₁₀

Average Mass

332.2601 Da

Monoisotopic Mass

332.07435 Da

IUPAC Name

[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

Traditional Name

[(2R,3S,4S,5R,6R)-3,4,5,6-tetrahydroxyoxan-2-yl]methyl 3,4,5-trihydroxybenzoate

CAS Registry Number

Not Available

SMILES

O[C@@H]1O[C@H](COC(=O)C2=CC(O)=C(O)C(O)=C2)[C@@H](O)[C@H](O)[C@H]1O

InChI Identifier

InChI=1S/C13H16O10/c14-5-1-4(2-6(15)8(5)16)12(20)22-3-7-9(17)10(18)11(19)13(21)23-7/h1-2,7,9-11,13-19,21H,3H2/t7-,9-,10+,11-,13-/m1/s1

InChI Key

VGVDLJNNDOFWKT-JEUROIALSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, CD3OD, experimental)	benjamin.metoyer@gmail.com	Polyphénols Biotech-ADERA, Unité de recherche Œnologie, UMR 1366 INRAE, ISVV, 33882 Villenave-d'Ornon, France	Benjamin Métoyer	2024-05-04	View Spectrum
HMBC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	benjamin.metoyer@gmail.com	Polyphénols Biotech-ADERA, Unité de recherche Œnologie, UMR 1366 INRAE, ISVV, 33882 Villenave-d'Ornon, France	Benjamin Métoyer	2024-05-04	View Spectrum
ROESY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	benjamin.metoyer@gmail.com	Polyphénols Biotech-ADERA, Unité de recherche Œnologie, UMR 1366 INRAE, ISVV, 33882 Villenave-d'Ornon, France	Benjamin Métoyer	2024-05-04	View Spectrum
HSQC NMR	[¹H, ¹³C] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	benjamin.metoyer@gmail.com	Polyphénols Biotech-ADERA, Unité de recherche Œnologie, UMR 1366 INRAE, ISVV, 33882 Villenave-d'Ornon, France	Benjamin Métoyer	2024-05-04	View Spectrum
COSY NMR	[¹H, ¹H] NMR Spectrum (2D, 600 MHz, CD3OD, experimental)	benjamin.metoyer@gmail.com	Polyphénols Biotech-ADERA, Unité de recherche Œnologie, UMR 1366 INRAE, ISVV, 33882 Villenave-d'Ornon, France	Benjamin Métoyer	2024-05-04	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CD3OD, experimental)	benjamin.metoyer@gmail.com	Polyphénols Biotech-ADERA, Unité de recherche Œnologie, UMR 1366 INRAE, ISVV, 33882 Villenave-d'Ornon, France	Benjamin Métoyer	2024-05-04	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View

Chemical Shift Submissions

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹H NMR Spectrum (1D, 600.27, CD₃OD, simulated)	benjamin.metoyer@gmail.com	Institut des sciences de la vigne et du vin	Métoyer	2024-05-04	View Spectrum

Species

Species of Origin

Species Name	Source	Reference
Castanea sativa		Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as galloyl esters. These are organic compounds that contain an ester derivative of 3,4,5-trihydroxybenzoic acid.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Galloyl esters

Alternative Parents

Substituents

Galloyl ester
P-hydroxybenzoic acid alkyl ester
M-hydroxybenzoic acid ester
P-hydroxybenzoic acid ester
Benzoate ester
Benzenetriol
Pyrogallol derivative
Benzoyl
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Monosaccharide
Oxane
Carboxylic acid ester
Hemiacetal
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Organoheterocyclic compound
Monocarboxylic acid or derivatives
Polyol
Alcohol
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

gallate ester (CHEBI:65941 )
galloyl beta-D-glucose (CHEBI:65941 )

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	-1.3	ALOGPS
logP	-1.3	ChemAxon
logS	-1.2	ALOGPS
pKa (Strongest Acidic)	8.11	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	9	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	177.14 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	71.69 m³·mol⁻¹	ChemAxon
Polarizability	30.6 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB006845

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5317463

PDB ID

Not Available

ChEBI ID

65941

Good Scents ID

Not Available

References

General References

Metoyer B, Renouf E, Jourdes M, Merillon JM, Teguo PW: Isolation of Hydrolyzable Tannins from Castanea sativa Using Centrifugal Partition Chromatography. J Nat Prod. 2024 Apr 26;87(4):652-663. doi: 10.1021/acs.jnatprod.3c00524. Epub 2024 Feb 15. [PubMed:38359463 ]
DOI: 10.1021/acs.jnatprod.3c00524
PMID: 38359463

Showing NP-Card for 6-galloyl-α-D-glucose + 6-galloyl-β-D-glucose (1:1, mol/mol) (NP0333063)

MOL for NP0333063 (6-galloyl-α-D-glucose + 6-galloyl-β-D-glucose (1:1, mol/mol) )

3D MOL for NP0333063 (6-galloyl-α-D-glucose + 6-galloyl-β-D-glucose (1:1, mol/mol) )

3D SDF for NP0333063 (6-galloyl-α-D-glucose + 6-galloyl-β-D-glucose (1:1, mol/mol) )

3D-SDF for NP0333063 (6-galloyl-α-D-glucose + 6-galloyl-β-D-glucose (1:1, mol/mol) )

PDB for NP0333063 (6-galloyl-α-D-glucose + 6-galloyl-β-D-glucose (1:1, mol/mol) )

3D PDB for NP0333063 (6-galloyl-α-D-glucose + 6-galloyl-β-D-glucose (1:1, mol/mol) )

SMILES for NP0333063 (6-galloyl-α-D-glucose + 6-galloyl-β-D-glucose (1:1, mol/mol) )

INCHI for NP0333063 (6-galloyl-α-D-glucose + 6-galloyl-β-D-glucose (1:1, mol/mol) )

Structure for NP0333063 (6-galloyl-α-D-glucose + 6-galloyl-β-D-glucose (1:1, mol/mol) )

3D Structure for NP0333063 (6-galloyl-α-D-glucose + 6-galloyl-β-D-glucose (1:1, mol/mol) )