NP-MRD: Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenoxy}oxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)propanoate (NP0243791)

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Record Information

Version

2.0

Created at

2022-09-07 04:25:17 UTC

Updated at

2022-09-07 04:25:17 UTC

NP-MRD ID

NP0243791

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenoxy}oxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)propanoate

Description

6''-O-(7,8-dihydrocaffeoyl)-alpha,beta-dihydrorhaponticin belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton. [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenoxy}oxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)propanoate is found in Tragopogon pratensis. Based on a literature review very few articles have been published on 6''-O-(7,8-dihydrocaffeoyl)-alpha,beta-dihydrorhaponticin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072206252D          

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M  END

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M  END


  Mrv1652309072206252D          

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    7.1447   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -5.3625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -5.3625    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.7145   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.9500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145   -5.3625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -7.8375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -8.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -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  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  2  0  0  0  0
 21 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
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  2  0  0  0  0
 25 32  1  0  0  0  0
 18 33  1  0  0  0  0
 33 34  1  1  0  0  0
 33 35  1  0  0  0  0
 35 36  1  6  0  0  0
 35 37  1  0  0  0  0
 16 37  1  0  0  0  0
 37 38  1  1  0  0  0
 14 39  2  0  0  0  0
  9 39  1  0  0  0  0
  6 40  1  0  0  0  0
 40 41  2  0  0  0  0
  3 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0243791

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(CCC2=CC(O)=CC(O[C@@H]3O[C@H](COC(=O)CCC4=CC=C(O)C(O)=C4)[C@@H](O)[C@H](O)[C@H]3O)=C2)C=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C30H34O12/c1-39-24-8-5-16(13-23(24)34)2-3-18-10-19(31)14-20(11-18)41-30-29(38)28(37)27(36)25(42-30)15-40-26(35)9-6-17-4-7-21(32)22(33)12-17/h4-5,7-8,10-14,25,27-34,36-38H,2-3,6,9,15H2,1H3/t25-,27-,28+,29-,30-/m1/s1

> <INCHI_KEY>
CWNGTSRPGSUPEU-LXRLAABLSA-N

> <FORMULA>
C30H34O12

> <MOLECULAR_WEIGHT>
586.59

> <EXACT_MASS>
586.205026535

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
59.672130857338686

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenoxy}oxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)propanoate

> <JCHEM_LOGP>
3.2860764356666663

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.595851125574665

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.041936266861493

> <JCHEM_PKA_STRONGEST_BASIC>
-3.6491029103322568

> <JCHEM_POLAR_SURFACE_AREA>
195.59999999999997

> <JCHEM_REFRACTIVITY>
147.3827

> <JCHEM_ROTATABLE_BOND_COUNT>
12

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenoxy}oxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)propanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 07-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-SEP-22         0                                  
HETATM    1  C   UNK     0      -4.001 -19.250   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -5.335 -18.480   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -5.335 -16.940   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.668 -16.170   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.668 -14.630   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      -5.335 -12.320   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.001 -11.550   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001 -10.010   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0       5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668  -5.390   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336  -6.930   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.669  -7.700   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.003  -6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      13.337  -7.700   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.337  -9.240   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      14.670 -10.010   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      12.003 -10.010   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      12.003 -11.550   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      10.669  -9.240   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       0.000  -9.240   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0      -1.334 -10.010   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0      -4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   41  C   UNK     0      -4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0      -2.667 -16.940   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   41                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   40                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   39                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15   39                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   37                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19   33                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   25                                                       
CONECT   33   18   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   16   38                                                  
CONECT   38   37                                                            
CONECT   39   14    9                                                       
CONECT   40    6   41                                                       
CONECT   41   40    3   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Value	Source
6''-O-(7,8-Dihydrocaffeoyl)-a,b-dihydrorhaponticin	Generator
6''-O-(7,8-Dihydrocaffeoyl)-α,β-dihydrorhaponticin	Generator

Chemical Formula

C₃₀H₃₄O₁₂

Average Mass

586.5900 Da

Monoisotopic Mass

586.20503 Da

IUPAC Name

Not Available

Traditional Name

Not Available

CAS Registry Number

Not Available

SMILES

COC1=CC=C(CCC2=CC(O)=CC(O[C@@H]3O[C@H](COC(=O)CCC4=CC=C(O)C(O)=C4)[C@@H](O)[C@H](O)[C@H]3O)=C2)C=C1O

InChI Identifier

InChI=1S/C30H34O12/c1-39-24-8-5-16(13-23(24)34)2-3-18-10-19(31)14-20(11-18)41-30-29(38)28(37)27(36)25(42-30)15-40-26(35)9-6-17-4-7-21(32)22(33)12-17/h4-5,7-8,10-14,25,27-34,36-38H,2-3,6,9,15H2,1H3/t25-,27-,28+,29-,30-/m1/s1

InChI Key

CWNGTSRPGSUPEU-LXRLAABLSA-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
Tragopogon pratensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as stilbene glycosides. Stilbene glycosides are compounds structurally characterized by the presence of a carbohydrate moiety glycosidically linked to the stilbene skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Stilbenes

Sub Class

Stilbene glycosides

Direct Parent

Stilbene glycosides

Alternative Parents

Substituents

Stilbene glycoside
Phenolic glycoside
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Anisole
Catechol
Phenoxy compound
Phenol ether
Methoxybenzene
Phenol
Fatty acid ester
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Fatty acyl
Benzenoid
Monocyclic benzene moiety
Oxane
Monosaccharide
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Polyol
Ether
Acetal
Monocarboxylic acid or derivatives
Organic oxide
Alcohol
Hydrocarbon derivative
Organic oxygen compound
Organooxygen compound
Carbonyl group
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

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

17250521

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

16091951

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenoxy}oxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)propanoate (NP0243791)

MOL for NP0243791 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenoxy}oxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)propanoate)

3D MOL for NP0243791 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenoxy}oxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)propanoate)

3D SDF for NP0243791 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenoxy}oxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)propanoate)

3D-SDF for NP0243791 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenoxy}oxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)propanoate)

PDB for NP0243791 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenoxy}oxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)propanoate)

3D PDB for NP0243791 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenoxy}oxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)propanoate)

SMILES for NP0243791 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenoxy}oxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)propanoate)

INCHI for NP0243791 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenoxy}oxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)propanoate)

Structure for NP0243791 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenoxy}oxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)propanoate)

3D Structure for NP0243791 ([(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-6-{3-hydroxy-5-[2-(3-hydroxy-4-methoxyphenyl)ethyl]phenoxy}oxan-2-yl]methyl 3-(3,4-dihydroxyphenyl)propanoate)