NP-MRD: Showing NP-Card for methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate (NP0321323)

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Record Information

Version

2.0

Created at

2022-09-11 23:28:23 UTC

Updated at

2022-09-11 23:28:23 UTC

NP-MRD ID

NP0321323

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate

Description

Methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position. methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate is found in Ligustrum lucidum. Methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191522332D          

 38 40  0  0  0  0            999 V2000
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 37 38  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004191522332D          

 38 40  0  0  0  0            999 V2000
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    1.4289   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  6 15  1  0  0  0  0
 15 16  1  0  0  0  0
  4 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
  3 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 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
 32 34  2  0  0  0  0
 27 34  1  0  0  0  0
 19 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 37 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0321323

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCC1C(OC2OC(CO)C(O)C(O)C2O)OC=C(C1CC(=O)OCCC1=CC=C(O)C(O)=C1)C(=O)OC

> <INCHI_IDENTIFIER>
InChI=1S/C25H34O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h4-5,8,11,13-14,18,20-22,24-28,30-32H,3,6-7,9-10H2,1-2H3

> <INCHI_KEY>
MPELAWXSOZTBPF-UHFFFAOYSA-N

> <FORMULA>
C25H34O13

> <MOLECULAR_WEIGHT>
542.534

> <EXACT_MASS>
542.199941155

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
54.219862014284644

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

> <ALOGPS_LOGP>
0.45

> <JCHEM_LOGP>
0.3245507740000009

> <ALOGPS_LOGS>
-2.78

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.094657782081036

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.284206923624142

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810847601468193

> <JCHEM_POLAR_SURFACE_AREA>
201.66999999999996

> <JCHEM_REFRACTIVITY>
127.50039999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
8.97e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 19-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   19-APR-15         0                                  
HETATM    1  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001 -10.010   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000 -13.860   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334 -16.170   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667 -16.940   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -4.001 -14.630   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.001 -11.550   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -1.334 -11.550   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.000  -9.240   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.335  -9.240   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   37  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   20                                                  
CONECT    4    3    5   17                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   15                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   11                                                  
CONECT    9    8   10                                                       
CONECT   10    9                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15                                                            
CONECT   17    4   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   35                                                  
CONECT   20   19    3   21                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   34                                                  
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   27                                                       
CONECT   35   19   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   38                                                       
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   80    0
END

View in JSmol

Synonyms

Value	Source
Methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylic acid	Generator

Chemical Formula

C₂₅H₃₄O₁₃

Average Mass

542.5340 Da

Monoisotopic Mass

542.19994 Da

IUPAC Name

methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-3-ethyl-2-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-3,4-dihydro-2H-pyran-5-carboxylate

Traditional Name

methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4H-pyran-3-carboxylate

CAS Registry Number

Not Available

SMILES

CCC1C(OC2OC(CO)C(O)C(O)C2O)OC=C(C1CC(=O)OCCC1=CC=C(O)C(O)=C1)C(=O)OC

InChI Identifier

InChI=1S/C25H34O13/c1-3-13-14(9-19(29)35-7-6-12-4-5-16(27)17(28)8-12)15(23(33)34-2)11-36-24(13)38-25-22(32)21(31)20(30)18(10-26)37-25/h4-5,8,11,13-14,18,20-22,24-28,30-32H,3,6-7,9-10H2,1-2H3

InChI Key

MPELAWXSOZTBPF-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
Ligustrum lucidum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-3-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C3-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-3-O-glycosides

Alternative Parents

Substituents

Flavonoid-3-o-glycoside
4p-methoxyflavonoid-skeleton
5-methoxyflavonoid-skeleton
Flavone
Chromone
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Benzodioxole
Phenoxy compound
Anisole
Methoxybenzene
Phenol ether
Alkyl aryl ether
Pyranone
Monocyclic benzene moiety
Benzenoid
Monosaccharide
Pyran
Oxane
Vinylogous ester
Heteroaromatic compound
Secondary alcohol
Ether
Organoheterocyclic compound
Oxacycle
Acetal
Polyol
Organic oxide
Organic oxygen compound
Alcohol
Organooxygen compound
Hydrocarbon derivative
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	0.45	ALOGPS
logP	0.32	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	9.28	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	201.67 Å²	ChemAxon
Rotatable Bond Count	12	ChemAxon
Refractivity	127.5 m³·mol⁻¹	ChemAxon
Polarizability	54.22 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

73157184

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate (NP0321323)

MOL for NP0321323 (methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D MOL for NP0321323 (methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D SDF for NP0321323 (methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D-SDF for NP0321323 (methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

PDB for NP0321323 (methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D PDB for NP0321323 (methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

SMILES for NP0321323 (methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

INCHI for NP0321323 (methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

Structure for NP0321323 (methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)

3D Structure for NP0321323 (methyl 4-{2-[2-(3,4-dihydroxyphenyl)ethoxy]-2-oxoethyl}-5-ethyl-6-{[3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-5,6-dihydro-4h-pyran-3-carboxylate)