NP-MRD: Showing NP-Card for (6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate (NP0191298)

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Record Information

Version

2.0

Created at

2022-09-04 08:12:16 UTC

Updated at

2022-09-04 08:12:16 UTC

NP-MRD ID

NP0191298

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate

Description

(6-{[3-(3,4-Dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. (6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate is found in Gentiana pyrenaica. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit (6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171512212D          

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M  END

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  Mrv1533004171512212D          

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   12.8605   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460  -10.3125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.0750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737   -9.9000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -9.0750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  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
  5  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  6 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  2  0  0  0  0
 17 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  2  0  0  0  0
 25 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 32 35  2  0  0  0  0
 27 35  1  0  0  0  0
 22 36  1  0  0  0  0
 36 37  1  0  0  0  0
 36 38  1  0  0  0  0
 38 39  1  0  0  0  0
 38 40  1  0  0  0  0
 20 40  1  0  0  0  0
 40 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0191298

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1OC)C(=O)OCC(C)C(=O)OC1OC(COC(=O)C2=CC=C(O)C(OC)=C2)C(O)C(O)C1O

> <INCHI_IDENTIFIER>
InChI=1S/C27H32O14/c1-13(11-38-25(33)15-6-8-17(35-2)19(10-15)37-4)24(32)41-27-23(31)22(30)21(29)20(40-27)12-39-26(34)14-5-7-16(28)18(9-14)36-3/h5-10,13,20-23,27-31H,11-12H2,1-4H3

> <INCHI_KEY>
OIIQCNVBKMYPJT-UHFFFAOYSA-N

> <FORMULA>
C27H32O14

> <MOLECULAR_WEIGHT>
580.539

> <EXACT_MASS>
580.17920571

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
56.7928849863015

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate

> <ALOGPS_LOGP>
1.53

> <JCHEM_LOGP>
1.685357739666667

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.19794650921597

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.991471806468581

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491128856281065

> <JCHEM_POLAR_SURFACE_AREA>
196.73999999999998

> <JCHEM_REFRACTIVITY>
137.06550000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
14

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.47e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       1.334 -14.630   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000 -13.860   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668 -14.630   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       6.668 -16.170   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       8.002 -13.860   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       9.336 -14.630   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      10.669 -13.860   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.669 -12.320   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      12.003 -14.630   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      12.003 -16.170   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      13.337 -13.860   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      14.670 -14.630   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.004 -13.860   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      17.338 -14.630   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.672 -13.860   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      20.005 -14.630   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      21.339 -13.860   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      21.339 -12.320   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      22.673 -14.630   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      24.006 -13.860   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      25.340 -14.630   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      25.340 -16.170   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      26.674 -16.940   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      24.006 -16.940   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      24.006 -18.480   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      22.673 -19.250   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      22.673 -16.170   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      17.338 -16.170   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0      18.672 -16.940   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0      16.004 -16.940   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0      16.004 -18.480   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      14.670 -16.170   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      13.337 -16.940   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   11                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    6   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   40                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   36                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28   35                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   35                                                  
CONECT   33   32   34                                                       
CONECT   34   33                                                            
CONECT   35   32   27                                                       
CONECT   36   22   37   38                                                  
CONECT   37   36                                                            
CONECT   38   36   39   40                                                  
CONECT   39   38                                                            
CONECT   40   38   20   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   86    0
END

View in JSmol

Synonyms

Value	Source
(6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoic acid	Generator

Chemical Formula

C₂₇H₃₂O₁₄

Average Mass

580.5390 Da

Monoisotopic Mass

580.17921 Da

IUPAC Name

(6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate

Traditional Name

(6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1OC)C(=O)OCC(C)C(=O)OC1OC(COC(=O)C2=CC=C(O)C(OC)=C2)C(O)C(O)C1O

InChI Identifier

InChI=1S/C27H32O14/c1-13(11-38-25(33)15-6-8-17(35-2)19(10-15)37-4)24(32)41-27-23(31)22(30)21(29)20(40-27)12-39-26(34)14-5-7-16(28)18(9-14)36-3/h5-10,13,20-23,27-31H,11-12H2,1-4H3

InChI Key

OIIQCNVBKMYPJT-UHFFFAOYSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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
Gentiana pyrenaica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as hydrolyzable tannins. These are tannins with a structure characterized by either of the following models. In model 1, the structure contains galloyl units (in some cases, shikimic acid units) that are linked to diverse polyol carbohydrate-, catechin-, or triterpenoid units. In model 2, contains at least two galloyl units C-C coupled to each other, and do not contain a glycosidically linked catechin unit.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Tannins

Sub Class

Hydrolyzable tannins

Direct Parent

Hydrolyzable tannins

Alternative Parents

Substituents

Hydrolyzable tannin
P-hydroxybenzoic acid alkyl ester
P-hydroxybenzoic acid ester
M-methoxybenzoic acid or derivatives
P-methoxybenzoic acid or derivatives
Benzoate ester
Methoxyphenol
Dimethoxybenzene
O-dimethoxybenzene
Benzoic acid or derivatives
Tricarboxylic acid or derivatives
Anisole
Methoxybenzene
Benzoyl
Phenoxy compound
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Phenol
Oxane
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Carboxylic acid ester
Oxacycle
Polyol
Ether
Carboxylic acid derivative
Organoheterocyclic compound
Acetal
Organooxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	1.53	ALOGPS
logP	1.69	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	8.99	ChemAxon
pKa (Strongest Basic)	-3.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	196.74 Å²	ChemAxon
Rotatable Bond Count	14	ChemAxon
Refractivity	137.07 m³·mol⁻¹	ChemAxon
Polarizability	56.79 Å³	ChemAxon
Number of Rings	3	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

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

14483895

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate (NP0191298)

MOL for NP0191298 ((6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate)

3D MOL for NP0191298 ((6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate)

3D SDF for NP0191298 ((6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate)

3D-SDF for NP0191298 ((6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate)

PDB for NP0191298 ((6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate)

3D PDB for NP0191298 ((6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate)

SMILES for NP0191298 ((6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate)

INCHI for NP0191298 ((6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate)

Structure for NP0191298 ((6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate)

3D Structure for NP0191298 ((6-{[3-(3,4-dimethoxybenzoyloxy)-2-methylpropanoyl]oxy}-3,4,5-trihydroxyoxan-2-yl)methyl 4-hydroxy-3-methoxybenzoate)