NP-MRD: Showing NP-Card for 6-(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one (NP0232620)

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Record Information

Version

2.0

Created at

2022-09-06 13:54:57 UTC

Updated at

2022-09-06 13:54:57 UTC

NP-MRD ID

NP0232620

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one

Description

6-(4-{[3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone. 6-(4-{[3,4-Dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171505062D          

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M  END

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  Mrv1533004171505062D          

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    5.0013   -0.4125    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
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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  2  0  0  0  0
  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 19 22  1  0  0  0  0
 22 23  1  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  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 29 33  1  0  0  0  0
 26 33  1  0  0  0  0
 33 34  1  0  0  0  0
 24 35  1  0  0  0  0
 17 35  1  0  0  0  0
 35 36  1  0  0  0  0
 16 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
 39 40  2  0  0  0  0
 13 40  1  0  0  0  0
 40 41  1  0  0  0  0
  9 41  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0232620

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C(C3OC(CO)C(O)C(OC4OCC(O)(CO)C4O)C3O)=C(O)C=C2O1

> <INCHI_IDENTIFIER>
InChI=1S/C27H30O14/c1-37-12-4-2-11(3-5-12)15-6-13(30)18-16(39-15)7-14(31)19(21(18)33)23-22(34)24(20(32)17(8-28)40-23)41-26-25(35)27(36,9-29)10-38-26/h2-7,17,20,22-26,28-29,31-36H,8-10H2,1H3

> <INCHI_KEY>
YDMXOIDNIPFRHO-UHFFFAOYSA-N

> <FORMULA>
C27H30O14

> <MOLECULAR_WEIGHT>
578.523

> <EXACT_MASS>
578.163555646

> <JCHEM_ACCEPTOR_COUNT>
14

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
57.82701887628036

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

> <ALOGPS_LOGP>
-0.12

> <JCHEM_LOGP>
-1.1812367753333328

> <ALOGPS_LOGS>
-2.48

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.755600941936667

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.138820971769322

> <JCHEM_PKA_STRONGEST_BASIC>
-2.9791998480836357

> <JCHEM_POLAR_SURFACE_AREA>
225.05999999999997

> <JCHEM_REFRACTIVITY>
137.1847

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.90e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0      -4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -4.001  -5.390   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      -2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000  -4.620   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  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.335   1.540   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      12.003   2.310   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      10.669  -0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      12.003  -0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      13.337  -0.000   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      13.498   1.532   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      15.004   1.852   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      15.774   0.518   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      17.020   1.423   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      16.805  -0.626   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0      18.311  -0.306   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0      14.744  -0.626   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      15.064  -2.133   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       9.336  -2.310   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   40  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0       2.667  -3.080   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9                                                  
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   41                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   40                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   37                                                  
CONECT   17   16   18   35                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20   22                                                  
CONECT   20   19   21                                                       
CONECT   21   20                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   35                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   33                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   31   33                                             
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31                                                            
CONECT   33   29   26   34                                                  
CONECT   34   33                                                            
CONECT   35   24   17   36                                                  
CONECT   36   35                                                            
CONECT   37   16   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   40                                                       
CONECT   40   39   13   41                                                  
CONECT   41   40    9                                                       
MASTER        0    0    0    0    0    0    0    0   41    0   90    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₃₀O₁₄

Average Mass

578.5230 Da

Monoisotopic Mass

578.16356 Da

IUPAC Name

6-(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)-4H-chromen-4-one

Traditional Name

6-(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C=C1)C1=CC(=O)C2=C(O)C(C3OC(CO)C(O)C(OC4OCC(O)(CO)C4O)C3O)=C(O)C=C2O1

InChI Identifier

InChI=1S/C27H30O14/c1-37-12-4-2-11(3-5-12)15-6-13(30)18-16(39-15)7-14(31)19(21(18)33)23-22(34)24(20(32)17(8-28)40-23)41-26-25(35)27(36,9-29)10-38-26/h2-7,17,20,22-26,28-29,31-36H,8-10H2,1H3

InChI Key

YDMXOIDNIPFRHO-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid c-glycosides. Flavonoid C-glycosides are compounds containing a carbohydrate moiety which is C-glycosidically linked to the 2-phenylchromen-4-one flavonoid backbone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid C-glycosides

Alternative Parents

Substituents

Flavonoid c-glycoside
4p-methoxyflavonoid-skeleton
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
7-hydroxyflavonoid
Phenolic glycoside
C-glycosyl compound
Chromone
Disaccharide
Glycosyl compound
O-glycosyl compound
Benzopyran
1-benzopyran
Anisole
Methoxybenzene
Phenoxy compound
Phenol ether
Alkyl aryl ether
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Oxane
Tertiary alcohol
Tetrahydrofuran
Vinylogous acid
Heteroaromatic compound
Secondary alcohol
Ether
Dialkyl ether
Acetal
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Organic oxygen compound
Alcohol
Hydrocarbon derivative
Primary alcohol
Organic oxide
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	-0.12	ALOGPS
logP	-1.2	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	6.14	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	14	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	225.06 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	137.18 m³·mol⁻¹	ChemAxon
Polarizability	57.83 Å³	ChemAxon
Number of Rings	5	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

73809264

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one (NP0232620)

MOL for NP0232620 (6-(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one)

3D MOL for NP0232620 (6-(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one)

3D SDF for NP0232620 (6-(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one)

3D-SDF for NP0232620 (6-(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one)

PDB for NP0232620 (6-(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one)

3D PDB for NP0232620 (6-(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one)

SMILES for NP0232620 (6-(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one)

INCHI for NP0232620 (6-(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one)

Structure for NP0232620 (6-(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one)

3D Structure for NP0232620 (6-(4-{[3,4-dihydroxy-4-(hydroxymethyl)oxolan-2-yl]oxy}-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl)-5,7-dihydroxy-2-(4-methoxyphenyl)chromen-4-one)