NP-MRD: Showing NP-Card for 9-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,5,8-trihydroxy-3-methyltetraphene-7,12-dione (NP0271965)

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Record Information

Version

2.0

Created at

2022-09-08 18:25:47 UTC

Updated at

2022-09-08 18:25:47 UTC

NP-MRD ID

NP0271965

Secondary Accession Numbers

None

Natural Product Identification

Common Name

9-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,5,8-trihydroxy-3-methyltetraphene-7,12-dione

Description

9-[(1R,5R,10R,11R,13S)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]Tetradecan-13-yl]-1,5,8-trihydroxy-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. Based on a literature review very few articles have been published on 9-[(1R,5R,10R,11R,13S)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]Tetradecan-13-yl]-1,5,8-trihydroxy-3-methyl-7,12-dihydrotetraphene-7,12-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082220252D          

 41 47  0  0  1  0            999 V2000
   -4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309082220252D          

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    2.8579    0.8250    0.0000 C   0  0  1  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
    2.1434    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  6  2  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
  2 13  1  0  0  0  0
  8 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 21 20  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  1  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  6  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 29 31  1  0  0  0  0
 31 32  1  0  0  0  0
 25 32  1  0  0  0  0
 32 33  1  0  0  0  0
 34 33  1  6  0  0  0
 23 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  1  1  0  0  0
 35 37  1  0  0  0  0
 21 37  1  0  0  0  0
 20 38  2  0  0  0  0
 16 38  1  0  0  0  0
 38 39  1  0  0  0  0
 17 40  1  0  0  0  0
  7 40  1  0  0  0  0
 40 41  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0271965

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1O[C@@H](C[C@H]2OC3O[C@H](C)C(=O)CC3O[C@H]12)C1=C(O)C2=C(C=C1)C(=O)C1=C(C=C(O)C3=CC(C)=CC(O)=C13)C2=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H28O10/c1-11-6-16-19(33)8-17-25(24(16)20(34)7-11)28(36)15-5-4-14(27(35)26(15)29(17)37)21-10-22-30(13(3)38-21)40-23-9-18(32)12(2)39-31(23)41-22/h4-8,12-13,21-23,30-31,33-35H,9-10H2,1-3H3/t12-,13-,21+,22-,23?,30-,31?/m1/s1

> <INCHI_KEY>
UAKCZICSIKJWDB-MEAGLVDUSA-N

> <FORMULA>
C31H28O10

> <MOLECULAR_WEIGHT>
560.555

> <EXACT_MASS>
560.168247102

> <JCHEM_ACCEPTOR_COUNT>
10

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
57.92488570701107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
9-[(1R,5R,10R,11R,13S)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0^{3,8}]tetradecan-13-yl]-1,5,8-trihydroxy-3-methyl-7,12-dihydrotetraphene-7,12-dione

> <JCHEM_LOGP>
4.908904526666667

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
7.82358407665878

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.829114317760134

> <JCHEM_PKA_STRONGEST_BASIC>
-3.7006984367707916

> <JCHEM_POLAR_SURFACE_AREA>
148.82

> <JCHEM_REFRACTIVITY>
144.31719999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
9-[(1R,5R,10R,11R,13S)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0^{3,8}]tetradecan-13-yl]-1,5,8-trihydroxy-3-methyltetraphene-7,12-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -8.002   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -6.668   8.470   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   9.240   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -4.001   8.470   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -2.667   9.240   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -4.001   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.667   6.160   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   4.620   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.001   3.850   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.335   4.620   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -6.668   3.850   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -5.335   6.160   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -6.668   6.930   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.334   2.310   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -0.000   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -0.000   6.160   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.334   6.930   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       2.667   6.160   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       5.335   4.620   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       8.002   4.620   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       9.336   3.850   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      10.669   4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      12.003   3.850   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.003   2.310   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      13.337   1.540   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      10.669   1.540   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       8.002   1.540   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       4.001   2.310   0.000  0.00  0.00           O+0
HETATM   38  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   40  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   41  O   UNK     0      -1.334   8.470   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   12                                                  
CONECT    7    6    8   40                                                  
CONECT    8    7    9   14                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6   13                                                  
CONECT   13   12    2                                                       
CONECT   14    8   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   38                                                  
CONECT   17   16   18   40                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   38                                                  
CONECT   21   20   22   37                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   34                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   32                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31                                                  
CONECT   30   29                                                            
CONECT   31   29   32                                                       
CONECT   32   31   25   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   23   35                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   21                                                       
CONECT   38   20   16   39                                                  
CONECT   39   38                                                            
CONECT   40   17    7   41                                                  
CONECT   41   40                                                            
MASTER        0    0    0    0    0    0    0    0   41    0   94    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₂₈O₁₀

Average Mass

560.5550 Da

Monoisotopic Mass

560.16825 Da

IUPAC Name

9-[(1R,5R,10R,11R,13S)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0^{3,8}]tetradecan-13-yl]-1,5,8-trihydroxy-3-methyl-7,12-dihydrotetraphene-7,12-dione

Traditional Name

9-[(1R,5R,10R,11R,13S)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0^{3,8}]tetradecan-13-yl]-1,5,8-trihydroxy-3-methyltetraphene-7,12-dione

CAS Registry Number

Not Available

SMILES

C[C@H]1O[C@@H](C[C@H]2OC3O[C@H](C)C(=O)CC3O[C@H]12)C1=C(O)C2=C(C=C1)C(=O)C1=C(C=C(O)C3=CC(C)=CC(O)=C13)C2=O

InChI Identifier

InChI=1S/C31H28O10/c1-11-6-16-19(33)8-17-25(24(16)20(34)7-11)28(36)15-5-4-14(27(35)26(15)29(17)37)21-10-22-30(13(3)38-21)40-23-9-18(32)12(2)39-31(23)41-22/h4-8,12-13,21-23,30-31,33-35H,9-10H2,1-3H3/t12-,13-,21+,22-,23?,30-,31?/m1/s1

InChI Key

UAKCZICSIKJWDB-MEAGLVDUSA-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 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
Hydroxyanthraquinone
Anthraquinone
9,10-anthraquinone
Phenanthrol
Phenanthrene
Anthracene
1-naphthol
Pyranodioxin
Aryl ketone
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Oxane
Para-dioxane
Vinylogous acid
Cyclic ketone
Ketone
Oxacycle
Organoheterocyclic compound
Polyol
Ether
Dialkyl ether
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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	4.91	ChemAxon
pKa (Strongest Acidic)	6.83	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	10	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	148.82 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	144.32 m³·mol⁻¹	ChemAxon
Polarizability	57.92 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	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

163195305

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 9-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,5,8-trihydroxy-3-methyltetraphene-7,12-dione (NP0271965)

MOL for NP0271965 (9-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,5,8-trihydroxy-3-methyltetraphene-7,12-dione)

3D MOL for NP0271965 (9-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,5,8-trihydroxy-3-methyltetraphene-7,12-dione)

3D SDF for NP0271965 (9-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,5,8-trihydroxy-3-methyltetraphene-7,12-dione)

3D-SDF for NP0271965 (9-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,5,8-trihydroxy-3-methyltetraphene-7,12-dione)

PDB for NP0271965 (9-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,5,8-trihydroxy-3-methyltetraphene-7,12-dione)

3D PDB for NP0271965 (9-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,5,8-trihydroxy-3-methyltetraphene-7,12-dione)

SMILES for NP0271965 (9-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,5,8-trihydroxy-3-methyltetraphene-7,12-dione)

INCHI for NP0271965 (9-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,5,8-trihydroxy-3-methyltetraphene-7,12-dione)

Structure for NP0271965 (9-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,5,8-trihydroxy-3-methyltetraphene-7,12-dione)

3D Structure for NP0271965 (9-[(1r,5r,10r,11r,13s)-5,11-dimethyl-6-oxo-2,4,9,12-tetraoxatricyclo[8.4.0.0³,⁸]tetradecan-13-yl]-1,5,8-trihydroxy-3-methyltetraphene-7,12-dione)