NP-MRD: Showing NP-Card for 5,7-Dihydroxy-6,8-di-C-methylflavone 7-[6''-(3-hydroxy-3-methylglutaryl)glucoside] (NP0060075)

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Record Information

Version

2.0

Created at

2022-04-28 05:11:28 UTC

Updated at

2022-04-28 05:11:28 UTC

NP-MRD ID

NP0060075

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5,7-Dihydroxy-6,8-di-C-methylflavone 7-[6''-(3-hydroxy-3-methylglutaryl)glucoside]

Description

(3R)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-hydroxy-6,8-dimethyl-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]oxan-2-yl]methoxy}pentanoic acid belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position. 5,7-Dihydroxy-6,8-di-C-methylflavone 7-[6''-(3-hydroxy-3-methylglutaryl)glucoside] is found in Matteuccia orientalis . Based on a literature review very few articles have been published on (3R)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-hydroxy-6,8-dimethyl-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]oxan-2-yl]methoxy}pentanoic acid.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652304282207112D          

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M  END

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M  END


  Mrv1652304282207112D          

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    2.8579    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    3.3000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8579    4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    4.5375    0.0000 C   0  0  0  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
    1.4289    4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0329    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6829    3.3000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -2.4750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  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
  1  6  1  0  0  0  0
  2  7  1  0  0  0  0
  7  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  2  0  0  0  0
 11 13  1  0  0  0  0
  7 13  2  0  0  0  0
 10 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
  9 17  2  0  0  0  0
 17 18  1  0  0  0  0
 16 19  1  0  0  0  0
 20 19  1  6  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 20 25  1  0  0  0  0
 24 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  2  0  0  0  0
 33 35  1  0  0  0  0
 31 36  1  6  0  0  0
 31 37  1  6  0  0  0
 23 38  1  1  0  0  0
 22 39  1  6  0  0  0
 21 40  1  1  0  0  0
 15 41  1  0  0  0  0
 14 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0060075

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=C(O[C@@H]2O[C@H](COC(=O)C[C@](C)(O)CC(O)=O)[C@@H](O)[C@H](O)[C@H]2O)C(C)=C2OC(=CC(=O)C2=C1O)C1=CC=CC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H32O13/c1-13-22(34)21-16(30)9-17(15-7-5-4-6-8-15)40-27(21)14(2)26(13)42-28-25(37)24(36)23(35)18(41-28)12-39-20(33)11-29(3,38)10-19(31)32/h4-9,18,23-25,28,34-38H,10-12H2,1-3H3,(H,31,32)/t18-,23-,24+,25-,28+,29-/m1/s1

> <INCHI_KEY>
KMYUBNLNPRIIHP-UFQGYGRQSA-N

> <FORMULA>
C29H32O13

> <MOLECULAR_WEIGHT>
588.562

> <EXACT_MASS>
588.18429109

> <JCHEM_ACCEPTOR_COUNT>
12

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
58.626351213460524

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
6

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-hydroxy-6,8-dimethyl-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]oxan-2-yl]methoxy}pentanoic acid

> <ALOGPS_LOGP>
1.47

> <JCHEM_LOGP>
1.685259024333333

> <ALOGPS_LOGS>
-3.22

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
8.210194202063455

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.7531479870521647

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0083920901482806

> <JCHEM_POLAR_SURFACE_AREA>
209.50999999999996

> <JCHEM_REFRACTIVITY>
143.80530000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-hydroxy-6,8-dimethyl-4-oxo-2-phenylchromen-7-yl)oxy]oxan-2-yl]methoxy}pentanoic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 28-APR-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   28-APR-22         0                                  
HETATM    1  C   UNK     0      -4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+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      -5.335  -4.620   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.335  -3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+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       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       5.335  -3.080   0.000  0.00  0.00           O+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  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.002  -0.000   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       6.668  -0.770   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       5.335   6.160   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.335   7.700   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.001   8.470   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  O   UNK     0       2.667   7.700   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.795   6.160   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       6.875   6.160   0.000  0.00  0.00           O+0
HETATM   38  O   UNK     0      10.669  -0.000   0.000  0.00  0.00           O+0
HETATM   39  O   UNK     0      10.669  -3.080   0.000  0.00  0.00           O+0
HETATM   40  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       5.335  -0.000   0.000  0.00  0.00           C+0
HETATM   42  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    2    8   13                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   17                                                  
CONECT   10    9   11   14                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11    7                                                       
CONECT   14   10   15   42                                                  
CONECT   15   14   16   41                                                  
CONECT   16   15   17   19                                                  
CONECT   17   16    9   18                                                  
CONECT   18   17                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21   25                                                  
CONECT   21   20   22   40                                                  
CONECT   22   21   23   39                                                  
CONECT   23   22   24   38                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24   20                                                       
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32   36   37                                             
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   31                                                            
CONECT   37   31                                                            
CONECT   38   23                                                            
CONECT   39   22                                                            
CONECT   40   21                                                            
CONECT   41   15                                                            
CONECT   42   14                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   90    0
END

View in JSmol

Synonyms

Value	Source
(3R)-3-Hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-hydroxy-6,8-dimethyl-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]oxan-2-yl]methoxy}pentanoate	Generator

Chemical Formula

C₂₉H₃₂O₁₃

Average Mass

588.5620 Da

Monoisotopic Mass

588.18429 Da

IUPAC Name

(3R)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-hydroxy-6,8-dimethyl-4-oxo-2-phenyl-4H-chromen-7-yl)oxy]oxan-2-yl]methoxy}pentanoic acid

Traditional Name

(3R)-3-hydroxy-3-methyl-5-oxo-5-{[(2R,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(5-hydroxy-6,8-dimethyl-4-oxo-2-phenylchromen-7-yl)oxy]oxan-2-yl]methoxy}pentanoic acid

CAS Registry Number

Not Available

SMILES

CC1=C(O[C@@H]2O[C@H](COC(=O)C[C@](C)(O)CC(O)=O)[C@@H](O)[C@H](O)[C@H]2O)C(C)=C2OC(=CC(=O)C2=C1O)C1=CC=CC=C1

InChI Identifier

InChI=1S/C29H32O13/c1-13-22(34)21-16(30)9-17(15-7-5-4-6-8-15)40-27(21)14(2)26(13)42-28-25(37)24(36)23(35)18(41-28)12-39-20(33)11-29(3,38)10-19(31)32/h4-9,18,23-25,28,34-38H,10-12H2,1-3H3,(H,31,32)/t18-,23-,24+,25-,28+,29-/m1/s1

InChI Key

KMYUBNLNPRIIHP-UFQGYGRQSA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Matteuccia orientalis	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as flavonoid-7-o-glycosides. These are phenolic compounds containing a flavonoid moiety which is O-glycosidically linked to carbohydrate moiety at the C7-position.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Flavonoids

Sub Class

Flavonoid glycosides

Direct Parent

Flavonoid-7-O-glycosides

Alternative Parents

Substituents

Flavonoid-7-o-glycoside
Saccharolipid
Hydroxyflavonoid
Flavone
5-hydroxyflavonoid
Phenolic glycoside
O-glycosyl compound
Glycosyl compound
Chromone
1-benzopyran
Benzopyran
Pyranone
Fatty acid ester
Fatty acyl
Benzenoid
Pyran
Oxane
Monosaccharide
Dicarboxylic acid or derivatives
Monocyclic benzene moiety
Heteroaromatic compound
Vinylogous acid
Tertiary alcohol
Secondary alcohol
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Polyol
Carboxylic acid
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
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	1.47	ALOGPS
logP	1.69	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	3.75	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	12	ChemAxon
Hydrogen Donor Count	6	ChemAxon
Polar Surface Area	209.51 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	143.81 m³·mol⁻¹	ChemAxon
Polarizability	58.63 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

162906160

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for 5,7-Dihydroxy-6,8-di-C-methylflavone 7-[6''-(3-hydroxy-3-methylglutaryl)glucoside] (NP0060075)

MOL for NP0060075 (5,7-Dihydroxy-6,8-di-C-methylflavone 7-[6''-(3-hydroxy-3-methylglutaryl)glucoside])

3D MOL for NP0060075 (5,7-Dihydroxy-6,8-di-C-methylflavone 7-[6''-(3-hydroxy-3-methylglutaryl)glucoside])

3D SDF for NP0060075 (5,7-Dihydroxy-6,8-di-C-methylflavone 7-[6''-(3-hydroxy-3-methylglutaryl)glucoside])

3D-SDF for NP0060075 (5,7-Dihydroxy-6,8-di-C-methylflavone 7-[6''-(3-hydroxy-3-methylglutaryl)glucoside])

PDB for NP0060075 (5,7-Dihydroxy-6,8-di-C-methylflavone 7-[6''-(3-hydroxy-3-methylglutaryl)glucoside])

3D PDB for NP0060075 (5,7-Dihydroxy-6,8-di-C-methylflavone 7-[6''-(3-hydroxy-3-methylglutaryl)glucoside])

SMILES for NP0060075 (5,7-Dihydroxy-6,8-di-C-methylflavone 7-[6''-(3-hydroxy-3-methylglutaryl)glucoside])

INCHI for NP0060075 (5,7-Dihydroxy-6,8-di-C-methylflavone 7-[6''-(3-hydroxy-3-methylglutaryl)glucoside])

Structure for NP0060075 (5,7-Dihydroxy-6,8-di-C-methylflavone 7-[6''-(3-hydroxy-3-methylglutaryl)glucoside])

3D Structure for NP0060075 (5,7-Dihydroxy-6,8-di-C-methylflavone 7-[6''-(3-hydroxy-3-methylglutaryl)glucoside])