NP-MRD: Showing NP-Card for 8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyltetraphene-7,12-dione (NP0184063)

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Record Information

Version

2.0

Created at

2022-09-03 23:05:48 UTC

Updated at

2022-09-03 23:05:49 UTC

NP-MRD ID

NP0184063

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyltetraphene-7,12-dione

Description

8-({5-[(4,5-Dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyl-7,12-dihydrotetraphene-7,12-dione belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone. 8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyltetraphene-7,12-dione is found in Streptomyces cyanogenus. 8-({5-[(4,5-Dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyl-7,12-dihydrotetraphene-7,12-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004251514272D          

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M  END

     RDKit          3D

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M  END


  Mrv1533004251514272D          

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    7.5274    0.7341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7974   -0.0454    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6075   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.8776   -0.9809    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6877   -1.1368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3375   -1.6046    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5274   -1.4486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9873   -2.0723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.2573   -0.6691    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3670    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0970    1.2018    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.8269   -0.2014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3965    0.2664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5864    0.4223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0463   -0.2014    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  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  2  8  1  0  0  0  0
  8  9  1  0  0  0  0
  4 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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 20 21  1  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 33 34  2  0  0  0  0
 34 35  1  0  0  0  0
 34 36  1  0  0  0  0
 25 36  2  0  0  0  0
 29 36  1  0  0  0  0
 26 37  1  0  0  0  0
 37 38  2  0  0  0  0
 37 39  1  0  0  0  0
 17 39  1  0  0  0  0
 22 39  2  0  0  0  0
 15 40  1  0  0  0  0
 40 41  1  0  0  0  0
 11 41  1  0  0  0  0
 41 42  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184063

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(CC(O)C1O)OC1C(C)OC(CC1O)OC1=CC=C(O)C2=C1C(=O)C1=CC=C3C=C(C)C=C(O)C3=C1C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H32O11/c1-12-8-15-4-5-16-25(24(15)18(33)9-12)30(38)26-17(32)6-7-21(27(26)29(16)37)41-22-11-20(35)31(14(3)40-22)42-23-10-19(34)28(36)13(2)39-23/h4-9,13-14,19-20,22-23,28,31-36H,10-11H2,1-3H3

> <INCHI_KEY>
NIYADHCAUUYEPB-UHFFFAOYSA-N

> <FORMULA>
C31H32O11

> <MOLECULAR_WEIGHT>
580.586

> <EXACT_MASS>
580.19446185

> <JCHEM_ACCEPTOR_COUNT>
11

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
59.137053893938386

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
5

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyl-7,12-dihydrotetraphene-7,12-dione

> <ALOGPS_LOGP>
2.65

> <JCHEM_LOGP>
4.017100576000001

> <ALOGPS_LOGS>
-3.48

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.040159307462064

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.40964583589982

> <JCHEM_PKA_STRONGEST_BASIC>
-3.2525606455789813

> <JCHEM_POLAR_SURFACE_AREA>
172.20999999999998

> <JCHEM_REFRACTIVITY>
147.034

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.93e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyltetraphene-7,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 25-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-APR-15         0                                  
HETATM    1  C   UNK     0      -4.096   0.788   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.584   0.497   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.576   1.661   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -0.063   1.370   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.441  -0.085   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.567  -1.249   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.063  -2.704   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      -2.080  -0.958   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0      -3.088  -2.122   0.000  0.00  0.00           O+0
HETATM   10  O   UNK     0       0.945   2.534   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.457   2.243   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.465   3.408   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.961   4.863   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.978   3.117   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.482   1.661   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.994   1.370   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.498  -0.085   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.490  -1.249   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.994  -2.704   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.506  -2.995   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       9.010  -4.450   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.514  -1.831   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      11.027  -2.122   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      11.531  -3.577   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      12.035  -0.958   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.531   0.497   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      12.539   1.661   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.051   1.370   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      14.555  -0.085   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      16.067  -0.376   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      16.571  -1.831   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      18.084  -2.122   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      15.563  -2.995   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      14.051  -2.704   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      13.043  -3.868   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0      13.547  -1.249   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      10.018   0.788   0.000  0.00  0.00           C+0
HETATM   38  O   UNK     0       9.514   2.243   0.000  0.00  0.00           O+0
HETATM   39  C   UNK     0       9.010  -0.376   0.000  0.00  0.00           C+0
HETATM   40  O   UNK     0       4.473   0.497   0.000  0.00  0.00           O+0
HETATM   41  C   UNK     0       2.961   0.788   0.000  0.00  0.00           C+0
HETATM   42  C   UNK     0       1.953  -0.376   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    2    9                                                  
CONECT    9    8                                                            
CONECT   10    4   11                                                       
CONECT   11   10   12   41                                                  
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   40                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   39                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23   39                                                  
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   36                                                  
CONECT   26   25   27   37                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30   36                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34   25   29                                                  
CONECT   37   26   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   17   22                                                  
CONECT   40   15   41                                                       
CONECT   41   40   11   42                                                  
CONECT   42   41                                                            
MASTER        0    0    0    0    0    0    0    0   42    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₂O₁₁

Average Mass

580.5860 Da

Monoisotopic Mass

580.19446 Da

IUPAC Name

8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyl-7,12-dihydrotetraphene-7,12-dione

Traditional Name

8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyltetraphene-7,12-dione

CAS Registry Number

Not Available

SMILES

CC1OC(CC(O)C1O)OC1C(C)OC(CC1O)OC1=CC=C(O)C2=C1C(=O)C1=CC=C3C=C(C)C=C(O)C3=C1C2=O

InChI Identifier

InChI=1S/C31H32O11/c1-12-8-15-4-5-16-25(24(15)18(33)9-12)30(38)26-17(32)6-7-21(27(26)29(16)37)41-22-11-20(35)31(14(3)40-22)42-23-10-19(34)28(36)13(2)39-23/h4-9,13-14,19-20,22-23,28,31-36H,10-11H2,1-3H3

InChI Key

NIYADHCAUUYEPB-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
Streptomyces cyanogenus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as angucyclines. These are polyketides with a structure based on then benz[a]anthracene skeleton, with the particularity that the central ring of the anthracene moiety is a para-quinone.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Angucyclines

Sub Class

Not Available

Direct Parent

Angucyclines

Alternative Parents

Substituents

Angucycline core
9,10-anthraquinone
Anthraquinone
Phenanthrol
Anthracene
Phenanthrene
Disaccharide
Glycosyl compound
1-naphthol
O-glycosyl compound
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
1-hydroxy-4-unsubstituted benzenoid
Benzenoid
Oxane
Vinylogous acid
Ketone
Secondary alcohol
Acetal
Organoheterocyclic compound
Oxacycle
Organooxygen compound
Hydrocarbon derivative
Aldehyde
Alcohol
Organic oxygen compound
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	2.65	ALOGPS
logP	4.02	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	8.41	ChemAxon
pKa (Strongest Basic)	-3.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	11	ChemAxon
Hydrogen Donor Count	5	ChemAxon
Polar Surface Area	172.21 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	147.03 m³·mol⁻¹	ChemAxon
Polarizability	59.14 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	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

75597901

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyltetraphene-7,12-dione (NP0184063)

MOL for NP0184063 (8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyltetraphene-7,12-dione)

3D MOL for NP0184063 (8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyltetraphene-7,12-dione)

3D SDF for NP0184063 (8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyltetraphene-7,12-dione)

3D-SDF for NP0184063 (8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyltetraphene-7,12-dione)

PDB for NP0184063 (8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyltetraphene-7,12-dione)

3D PDB for NP0184063 (8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyltetraphene-7,12-dione)

SMILES for NP0184063 (8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyltetraphene-7,12-dione)

INCHI for NP0184063 (8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyltetraphene-7,12-dione)

Structure for NP0184063 (8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyltetraphene-7,12-dione)

3D Structure for NP0184063 (8-({5-[(4,5-dihydroxy-6-methyloxan-2-yl)oxy]-4-hydroxy-6-methyloxan-2-yl}oxy)-1,11-dihydroxy-3-methyltetraphene-7,12-dione)