NP-MRD: Showing NP-Card for (2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]oxy}oxan-3-yl acetate (NP0251226)

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Record Information

Version

2.0

Created at

2022-09-07 14:21:56 UTC

Updated at

2022-09-07 14:21:56 UTC

NP-MRD ID

NP0251226

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]oxy}oxan-3-yl acetate

Description

(2R,3R)-8-[(2-O-Acetyl-beta-D-glucopyranosyl)oxy]-3,4',5,7-tetrahydroxyflavanone belongs to the class of organic compounds known as flavonoid-8-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C8-position. (2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]oxy}oxan-3-yl acetate is found in Calluna vulgaris. Based on a literature review very few articles have been published on (2R,3R)-8-[(2-O-Acetyl-beta-D-glucopyranosyl)oxy]-3,4',5,7-tetrahydroxyflavanone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309072216212D          

 36 39  0  0  1  0            999 V2000
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    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
   -0.7145    2.0625    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 C   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
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    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8579    2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309072216212D          

 36 39  0  0  1  0            999 V2000
    0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0251226

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(O)C=C(O)C2=C1O[C@@H]([C@@H](O)C2=O)C1=CC=C(O)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C23H24O13/c1-8(25)33-22-17(31)15(29)13(7-24)34-23(22)36-20-12(28)6-11(27)14-16(30)18(32)19(35-21(14)20)9-2-4-10(26)5-3-9/h2-6,13,15,17-19,22-24,26-29,31-32H,7H2,1H3/t13-,15-,17+,18+,19-,22-,23+/m1/s1

> <INCHI_KEY>
PEHKDZYHMFEOTK-DFNIUYQXSA-N

> <FORMULA>
C23H24O13

> <MOLECULAR_WEIGHT>
508.432

> <EXACT_MASS>
508.121690833

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
47.59044675950074

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
7

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-8-yl]oxy}oxan-3-yl acetate

> <JCHEM_LOGP>
-0.010558415000000043

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.31575027302363

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.121994455292311

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9810930120670314

> <JCHEM_POLAR_SURFACE_AREA>
212.67

> <JCHEM_REFRACTIVITY>
115.90480000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]oxy}oxan-3-yl acetate

> <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       1.334   6.930   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.334   6.930   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.000   4.620   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.000  -4.620   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667  -0.000   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       9.336   2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       2.667  -4.620   0.000  0.00  0.00           O+0
HETATM   29  O   UNK     0      -2.667   1.540   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      -6.668   2.310   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      -5.335   4.620   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0      -2.667   6.160   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7   29                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   27                                                  
CONECT   15   14    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   25                                                  
CONECT   18   17   19   24                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22   23                                                  
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   18                                                       
CONECT   25   17   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   14   28                                                  
CONECT   28   27                                                            
CONECT   29    6   30                                                       
CONECT   30   29   31   33                                                  
CONECT   31   30   32                                                       
CONECT   32   31                                                            
CONECT   33   30   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33    5   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   78    0
END

View in JSmol

Synonyms

Value	Source
(2R,3R)-8-[(2-O-Acetyl-b-D-glucopyranosyl)oxy]-3,4',5,7-tetrahydroxyflavanone	Generator
(2R,3R)-8-[(2-O-Acetyl-β-D-glucopyranosyl)oxy]-3,4',5,7-tetrahydroxyflavanone	Generator

Chemical Formula

C₂₃H₂₄O₁₃

Average Mass

508.4320 Da

Monoisotopic Mass

508.12169 Da

IUPAC Name

(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-3,4-dihydro-2H-1-benzopyran-8-yl]oxy}oxan-3-yl acetate

Traditional Name

(2S,3R,4S,5S,6R)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2R,3R)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]oxy}oxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC1=C(O)C=C(O)C2=C1O[C@@H]([C@@H](O)C2=O)C1=CC=C(O)C=C1

InChI Identifier

InChI=1S/C23H24O13/c1-8(25)33-22-17(31)15(29)13(7-24)34-23(22)36-20-12(28)6-11(27)14-16(30)18(32)19(35-21(14)20)9-2-4-10(26)5-3-9/h2-6,13,15,17-19,22-24,26-29,31-32H,7H2,1H3/t13-,15-,17+,18+,19-,22-,23+/m1/s1

InChI Key

PEHKDZYHMFEOTK-DFNIUYQXSA-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
Calluna vulgaris	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-8-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C8-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-8-O-glycosides

Alternative Parents

Substituents

Flavonoid-8-o-glycoside
3-hydroxyflavonoid
4'-hydroxyflavonoid
5-hydroxyflavonoid
7-hydroxyflavonoid
Hydroxyflavonoid
Flavanonol
Flavanone
Flavan
Phenolic glycoside
Glycosyl compound
Chromone
O-glycosyl compound
Benzopyran
Chromane
1-benzopyran
Aryl ketone
Aryl alkyl ketone
Phenol
1-hydroxy-2-unsubstituted benzenoid
Alkyl aryl ether
Oxane
Benzenoid
Monosaccharide
Monocyclic benzene moiety
Vinylogous acid
Carboxylic acid ester
Secondary alcohol
Ketone
Oxacycle
Acetal
Organoheterocyclic compound
Polyol
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Ether
Primary alcohol
Organic oxygen compound
Organooxygen compound
Carbonyl group
Organic oxide
Alcohol
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	-0.011	ChemAxon
pKa (Strongest Acidic)	8.12	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	7	ChemAxon
Polar Surface Area	212.67 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	115.9 m³·mol⁻¹	ChemAxon
Polarizability	47.59 Å³	ChemAxon
Number of Rings	4	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

101923622

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]oxy}oxan-3-yl acetate (NP0251226)

MOL for NP0251226 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]oxy}oxan-3-yl acetate)

3D MOL for NP0251226 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]oxy}oxan-3-yl acetate)

3D SDF for NP0251226 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]oxy}oxan-3-yl acetate)

3D-SDF for NP0251226 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]oxy}oxan-3-yl acetate)

PDB for NP0251226 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]oxy}oxan-3-yl acetate)

3D PDB for NP0251226 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]oxy}oxan-3-yl acetate)

SMILES for NP0251226 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]oxy}oxan-3-yl acetate)

INCHI for NP0251226 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]oxy}oxan-3-yl acetate)

Structure for NP0251226 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]oxy}oxan-3-yl acetate)

3D Structure for NP0251226 ((2s,3r,4s,5s,6r)-4,5-dihydroxy-6-(hydroxymethyl)-2-{[(2r,3r)-3,5,7-trihydroxy-2-(4-hydroxyphenyl)-4-oxo-2,3-dihydro-1-benzopyran-8-yl]oxy}oxan-3-yl acetate)