NP-MRD: Showing NP-Card for 2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol (NP0327701)

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Record Information

Version

2.0

Created at

2022-09-12 10:30:59 UTC

Updated at

2022-09-12 10:30:59 UTC

NP-MRD ID

NP0327701

Secondary Accession Numbers

None

Natural Product Identification

Common Name

2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Description

2-(4-{1,3-Dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones. 2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol is found in Eucommia ulmoides and Ligularia veitchiana. 2-(4-{1,3-Dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004191519572D          

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M  END

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M  END


  Mrv1533004191519572D          

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    3.5724   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -6.6000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -7.4250    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 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -9.9000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434  -10.3125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -6.6000    0.0000 C   0  0  0  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
    0.7145   -5.3625    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  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
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 12 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 10 19  1  0  0  0  0
 19 20  1  0  0  0  0
  5 21  1  0  0  0  0
 21 22  1  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
 23 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  1  0  0  0  0
 28 31  1  0  0  0  0
 31 32  2  0  0  0  0
 33 32  1  4  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  0  0  0  0
 32 37  1  0  0  0  0
 37 38  2  0  0  0  0
 27 38  1  0  0  0  0
 38 39  1  0  0  0  0
 39 40  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0327701

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(=CC=C1OC1OC(CO)C(O)C(O)C1O)C(O)C(CO)OC1=C(OC)C=C(C=CCO)C=C1OC

> <INCHI_IDENTIFIER>
InChI=1S/C27H36O13/c1-35-17-11-15(6-7-16(17)39-27-25(34)24(33)23(32)21(13-30)40-27)22(31)20(12-29)38-26-18(36-2)9-14(5-4-8-28)10-19(26)37-3/h4-7,9-11,20-25,27-34H,8,12-13H2,1-3H3

> <INCHI_KEY>
XMGKCJUCYBLMBY-UHFFFAOYSA-N

> <FORMULA>
C27H36O13

> <MOLECULAR_WEIGHT>
568.572

> <EXACT_MASS>
568.215591219

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
58.09975801212664

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <ALOGPS_LOGP>
0.24

> <JCHEM_LOGP>
-0.9227035223333329

> <ALOGPS_LOGS>
-3.05

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.979978463650248

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.167474409136984

> <JCHEM_PKA_STRONGEST_BASIC>
-2.5264907609046254

> <JCHEM_POLAR_SURFACE_AREA>
196.98999999999995

> <JCHEM_REFRACTIVITY>
139.7082

> <JCHEM_ROTATABLE_BOND_COUNT>
13

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.06e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

> <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       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -7.700   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -1.334  -6.930   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.667  -7.700   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.667  -9.240   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.335  -7.700   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      -2.667  -3.080   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.002  -9.240   0.000  0.00  0.00           O+0
HETATM   26  O   UNK     0       4.001 -10.010   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.001 -11.550   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335 -12.320   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.668 -11.550   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.002 -12.320   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335 -13.860   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       4.001 -14.630   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001 -16.170   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       2.667 -18.480   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.001 -19.250   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.667 -13.860   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.334 -11.550   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0       1.334 -10.010   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   21                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    3    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   19                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12   14                                                       
CONECT   14   13                                                            
CONECT   15   12   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   10   20                                                  
CONECT   20   19                                                            
CONECT   21    5   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24   26                                                  
CONECT   24   23   25                                                       
CONECT   25   24                                                            
CONECT   26   23   27                                                       
CONECT   27   26   28   38                                                  
CONECT   28   27   29   31                                                  
CONECT   29   28   30                                                       
CONECT   30   29                                                            
CONECT   31   28   32                                                       
CONECT   32   31   33   37                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35                                                            
CONECT   37   32   38                                                       
CONECT   38   37   27   39                                                  
CONECT   39   38   40                                                       
CONECT   40   39                                                            
MASTER        0    0    0    0    0    0    0    0   40    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₆O₁₃

Average Mass

568.5720 Da

Monoisotopic Mass

568.21559 Da

IUPAC Name

2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

Traditional Name

2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol

CAS Registry Number

Not Available

SMILES

COC1=CC(=CC=C1OC1OC(CO)C(O)C(O)C1O)C(O)C(CO)OC1=C(OC)C=C(C=CCO)C=C1OC

InChI Identifier

InChI=1S/C27H36O13/c1-35-17-11-15(6-7-16(17)39-27-25(34)24(33)23(32)21(13-30)40-27)22(31)20(12-29)38-26-18(36-2)9-14(5-4-8-28)10-19(26)37-3/h4-7,9-11,20-25,27-34H,8,12-13H2,1-3H3

InChI Key

XMGKCJUCYBLMBY-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
Eucommia ulmoides	LOTUS Database	35616633
Ligularia veitchiana	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as lignan glycosides. These are aromatic polycyclic compounds containing a carbohydrate component glycosidically linked to a lignan moiety. They include 1-aryltetralin lactones.

Kingdom

Organic compounds

Super Class

Lignans, neolignans and related compounds

Class

Lignan glycosides

Sub Class

Not Available

Direct Parent

Lignan glycosides

Alternative Parents

Substituents

Lignan glycoside
Phenolic glycoside
Hexose monosaccharide
O-glycosyl compound
Glycosyl compound
Cinnamyl alcohol
M-dimethoxybenzene
Dimethoxybenzene
Phenoxy compound
Phenol ether
Anisole
Styrene
Methoxybenzene
Alkyl aryl ether
Oxane
Monosaccharide
Monocyclic benzene moiety
Benzenoid
Secondary alcohol
Acetal
Oxacycle
Organoheterocyclic compound
Ether
Polyol
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Aromatic alcohol
Primary alcohol
Organooxygen compound
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	0.24	ALOGPS
logP	-0.92	ChemAxon
logS	-3	ALOGPS
pKa (Strongest Acidic)	12.17	ChemAxon
pKa (Strongest Basic)	-2.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	196.99 Å²	ChemAxon
Rotatable Bond Count	13	ChemAxon
Refractivity	139.71 m³·mol⁻¹	ChemAxon
Polarizability	58.1 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

72759220

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol (NP0327701)

MOL for NP0327701 (2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D MOL for NP0327701 (2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D SDF for NP0327701 (2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D-SDF for NP0327701 (2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

PDB for NP0327701 (2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D PDB for NP0327701 (2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

SMILES for NP0327701 (2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

INCHI for NP0327701 (2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

Structure for NP0327701 (2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)

3D Structure for NP0327701 (2-(4-{1,3-dihydroxy-2-[4-(3-hydroxyprop-1-en-1-yl)-2,6-dimethoxyphenoxy]propyl}-2-methoxyphenoxy)-6-(hydroxymethyl)oxane-3,4,5-triol)