NP-MRD: Showing NP-Card for (3r,4r)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one (NP0219177)

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Record Information

Version

1.0

Created at

2022-09-05 20:05:27 UTC

Updated at

2022-09-05 20:05:28 UTC

NP-MRD ID

NP0219177

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4r)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

Description

Matairesinol monoglucoside 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. (3r,4r)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one is found in Saussurea parviflora. It was first documented in 2022 (PMID: 36075691). Based on a literature review a significant number of articles have been published on Matairesinol monoglucoside (PMID: 36075690) (PMID: 36075689) (PMID: 36075688) (PMID: 36075687).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052222052D          

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M  END

     RDKit          3D

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  Mrv1652309052222052D          

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 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 19 18  1  6  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  6  0  0  0
 22 23  1  0  0  0  0
 21 24  1  0  0  0  0
 24 25  1  1  0  0  0
 24 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  1  0  0  0
 17 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 30 33  2  0  0  0  0
 14 33  1  0  0  0  0
  5 34  2  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
  3 36  1  0  0  0  0
 36 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0219177

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC(C[C@@H]2[C@@H](CC3=CC=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(OC)=C3)COC2=O)=CC=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C26H32O11/c1-33-19-9-14(3-5-17(19)28)8-16-15(12-35-25(16)32)7-13-4-6-18(20(10-13)34-2)36-26-24(31)23(30)22(29)21(11-27)37-26/h3-6,9-10,15-16,21-24,26-31H,7-8,11-12H2,1-2H3/t15-,16+,21+,22+,23-,24+,26+/m0/s1

> <INCHI_KEY>
FWRZDNFXFFWBGP-LHHMAMHXSA-N

> <FORMULA>
C26H32O11

> <MOLECULAR_WEIGHT>
520.531

> <EXACT_MASS>
520.19446185

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
51.11024257074025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4R)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

> <JCHEM_LOGP>
1.0237144176666668

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.202181540681128

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.943135640673946

> <JCHEM_PKA_STRONGEST_BASIC>
-2.981092354907191

> <JCHEM_POLAR_SURFACE_AREA>
164.37

> <JCHEM_REFRACTIVITY>
127.77880000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4R)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.334  -5.390   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.755  -7.835   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -1.291  -7.359   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0      -3.231  -9.300   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -4.771  -9.300   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.247  -7.835   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.712  -7.359   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -7.032  -5.853   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -8.496  -5.377   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -8.817  -3.871   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -7.672  -2.840   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      -7.992  -1.334   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      -9.457  -0.858   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0     -10.601  -1.888   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0     -12.066  -1.413   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0     -13.210  -2.443   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0     -12.890  -3.949   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0     -12.386   0.094   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0     -13.851   0.570   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0     -11.242   1.124   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0     -11.562   2.631   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -9.777   0.648   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -8.633   1.679   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -6.207  -3.316   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -5.063  -2.286   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0      -3.598  -2.762   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -5.887  -4.822   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   34                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   12                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11    7   13                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15   33                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   30                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   24                                                  
CONECT   22   21   23                                                       
CONECT   23   22                                                            
CONECT   24   21   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   19   29                                                  
CONECT   29   28                                                            
CONECT   30   17   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   14                                                       
CONECT   34    5   35                                                       
CONECT   35   34   36                                                       
CONECT   36   35    3   37                                                  
CONECT   37   36                                                            
MASTER        0    0    0    0    0    0    0    0   37    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₂O₁₁

Average Mass

520.5310 Da

Monoisotopic Mass

520.19446 Da

IUPAC Name

(3R,4R)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

Traditional Name

(3R,4R)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2S,3R,4S,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one

CAS Registry Number

Not Available

SMILES

COC1=CC(C[C@@H]2[C@@H](CC3=CC=C(O[C@@H]4O[C@H](CO)[C@@H](O)[C@H](O)[C@H]4O)C(OC)=C3)COC2=O)=CC=C1O

InChI Identifier

InChI=1S/C26H32O11/c1-33-19-9-14(3-5-17(19)28)8-16-15(12-35-25(16)32)7-13-4-6-18(20(10-13)34-2)36-26-24(31)23(30)22(29)21(11-27)37-26/h3-6,9-10,15-16,21-24,26-31H,7-8,11-12H2,1-2H3/t15-,16+,21+,22+,23-,24+,26+/m0/s1

InChI Key

FWRZDNFXFFWBGP-LHHMAMHXSA-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
Saussurea parviflora	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
Dibenzylbutyrolactone
Lignan lactone
Tetrahydrofuran lignan
9,9p-epoxylignan
Furanoid lignan
Phenolic glycoside
Fatty acyl glycoside of mono- or disaccharide
Fatty acyl glycoside
Alkyl glycoside
Glycosyl compound
O-glycosyl compound
Methoxyphenol
Phenol ether
Phenoxy compound
Methoxybenzene
Anisole
Phenol
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
Monocyclic benzene moiety
Fatty acyl
Gamma butyrolactone
Benzenoid
Monosaccharide
Oxane
Tetrahydrofuran
Secondary alcohol
Lactone
Carboxylic acid ester
Polyol
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Oxacycle
Ether
Organoheterocyclic compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Primary alcohol
Alcohol
Organic oxygen 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	1.02	ChemAxon
pKa (Strongest Acidic)	9.94	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	164.37 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	127.78 m³·mol⁻¹	ChemAxon
Polarizability	51.11 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

23550858

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

23757184

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Abioye AI, Sudfeld CR, Hughes MD, Aboud S, Muhihi A, Ulenga N, Nagu TJ, Wang M, Mugusi F, Fawzi WW: Iron status among HIV-infected adults during the first year of antiretroviral therapy in Tanzania. HIV Med. 2022 Sep 8. doi: 10.1111/hiv.13396. [PubMed:36075691 ]
Authors unspecified: Resources Round-up. Altern Lab Anim. 2022 Sep 8:2611929221121256. doi: 10.1177/02611929221121256. [PubMed:36075690 ]
Kim JU, Khan W, Arowoshola L, Ahmad M: Correspondence. Eur Heart J Qual Care Clin Outcomes. 2022 Aug 26. pii: 6677390. doi: 10.1093/ehjqcco/qcac051. [PubMed:36075689 ]
DaVault L: Field Amputations Facilitated by a Surgical Extraction Team. Am Surg. 2022 Sep 8:31348221114521. doi: 10.1177/00031348221114521. [PubMed:36075688 ]
Szanyi J, Walles JK, Tesfaye F, Gudeta AN, Bjorkman P: Intrauterine HIV exposure is associated with linear growth restriction among Ethiopian children in the first 18 months of life. Trop Med Int Health. 2022 Sep;27(9):823-830. doi: 10.1111/tmi.13805. Epub 2022 Aug 17. [PubMed:36075687 ]
LOTUS database [Link]

Showing NP-Card for (3r,4r)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one (NP0219177)

MOL for NP0219177 ((3r,4r)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

3D MOL for NP0219177 ((3r,4r)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

3D SDF for NP0219177 ((3r,4r)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

3D-SDF for NP0219177 ((3r,4r)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

PDB for NP0219177 ((3r,4r)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

3D PDB for NP0219177 ((3r,4r)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

SMILES for NP0219177 ((3r,4r)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

INCHI for NP0219177 ((3r,4r)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

Structure for NP0219177 ((3r,4r)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)

3D Structure for NP0219177 ((3r,4r)-3-[(4-hydroxy-3-methoxyphenyl)methyl]-4-[(3-methoxy-4-{[(2s,3r,4s,5s,6r)-3,4,5-trihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}phenyl)methyl]oxolan-2-one)