NP-MRD: Showing NP-Card for (6s,8r,11ar,12r,14ar,15r,17ar)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-8h,9h,11ah,12h,14ah,15h-1,3-dioxacyclotrideca[4,5-d]isoindole-2,7-dione (NP0226470)

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Record Information

Version

2.0

Created at

2022-09-06 05:31:05 UTC

Updated at

2022-09-06 05:31:05 UTC

NP-MRD ID

NP0226470

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(6s,8r,11ar,12r,14ar,15r,17ar)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-8h,9h,11ah,12h,14ah,15h-1,3-dioxacyclotrideca[4,5-d]isoindole-2,7-dione

Description

Scoparasin A belongs to the class of organic compounds known as isoindoles. These are heteropolycyclic compounds with a structure containing isoindole, a benzo-fused pyrrole. (6s,8r,11ar,12r,14ar,15r,17ar)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-8h,9h,11ah,12h,14ah,15h-1,3-dioxacyclotrideca[4,5-d]isoindole-2,7-dione is found in Garcinia dulcis and Peroneutypa scoparia. Based on a literature review very few articles have been published on Scoparasin A.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062207312D          

 38 41  0  0  1  0            999 V2000
    0.4035    3.9267    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    0.3881    0.9522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1858    0.1524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7773   -0.4227    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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  6 37  1  0  0  0  0
 37 38  2  0  0  0  0
  3 38  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309062207312D          

 38 41  0  0  1  0            999 V2000
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    0.6597   -1.2393    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.2034    1.5273    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0011    2.3271    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  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
  8  7  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 12 10  1  6  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 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  1  1  0  0  0
 19 21  1  6  0  0  0
 19 22  1  0  0  0  0
 22 23  2  0  0  0  0
 22 24  1  0  0  0  0
 24 25  1  6  0  0  0
 24 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 29 28  1  6  0  0  0
 12 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  1  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 34 35  1  0  0  0  0
 36 34  1  6  0  0  0
  8 36  1  0  0  0  0
 12 36  1  0  0  0  0
  6 37  1  0  0  0  0
 37 38  2  0  0  0  0
  3 38  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0226470

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1=CC=C(C[C@H]2N=C(O)[C@]34OC(=O)O\C=C\[C@](C)(O)C(=O)[C@H](C)C\C=C\[C@@H]3[C@@H](O)C(C)=C(C)[C@H]24)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H35NO8/c1-16-7-6-8-21-24(31)18(3)17(2)23-22(15-19-9-11-20(36-5)12-10-19)30-26(33)29(21,23)38-27(34)37-14-13-28(4,35)25(16)32/h6,8-14,16,21-24,31,35H,7,15H2,1-5H3,(H,30,33)/b8-6+,14-13+/t16-,21-,22-,23-,24+,28+,29+/m1/s1

> <INCHI_KEY>
UKXQRSOMKIGRCJ-ZLVRRUFZSA-N

> <FORMULA>
C29H35NO8

> <MOLECULAR_WEIGHT>
525.598

> <EXACT_MASS>
525.236267091

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
53.58872396747743

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(6S,8R,12R,14aR,15R,17aR,17bR)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-2H,6H,7H,8H,9H,12H,14aH,15H,17bH-1,3-dioxacyclotrideca[5,4-e]isoindole-2,7-dione

> <JCHEM_LOGP>
2.5399427984686644

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.770235417959256

> <JCHEM_PKA_STRONGEST_ACIDIC>
1.496973379957737

> <JCHEM_PKA_STRONGEST_BASIC>
4.399684230353119

> <JCHEM_POLAR_SURFACE_AREA>
134.88000000000002

> <JCHEM_REFRACTIVITY>
140.87720000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(6S,8R,12R,14aR,15R,17aR,17bR)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-8H,9H,12H,14aH,15H,17bH-1,3-dioxacyclotrideca[5,4-e]isoindole-2,7-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       0.753   7.330   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       1.857   6.256   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       1.480   4.763   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.584   3.690   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.206   2.197   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.724   1.777   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.347   0.284   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.451  -0.789   0.000  0.00  0.00           C+0
HETATM    9  N   UNK     0       2.968  -0.527   0.000  0.00  0.00           N+0
HETATM   10  C   UNK     0       3.473  -1.847   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       5.211  -2.109   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       2.613  -2.993   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.972  -1.996   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       4.349  -0.503   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.363   0.680   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       5.886  -0.400   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       6.458  -1.830   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.936  -2.639   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.038  -4.176   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.534  -3.808   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.660  -5.585   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       6.759  -5.033   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       5.377  -4.353   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       6.861  -6.569   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.243  -7.249   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       5.581  -7.426   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.200  -6.746   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.097  -5.210   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.716  -4.530   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.436  -5.387   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.538  -6.923   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.054  -4.707   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.226  -5.564   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      -0.048  -3.170   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      -1.430  -2.490   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.231  -2.313   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.380   2.851   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -0.002   4.344   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   38                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   37                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   36                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   29   36                                             
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21   22                                             
CONECT   20   19                                                            
CONECT   21   19                                                            
CONECT   22   19   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   12   30                                                  
CONECT   30   29   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    8   12                                                  
CONECT   37    6   38                                                       
CONECT   38   37    3                                                       
MASTER        0    0    0    0    0    0    0    0   38    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₃₅NO₈

Average Mass

525.5980 Da

Monoisotopic Mass

525.23627 Da

IUPAC Name

(6S,8R,12R,14aR,15R,17aR,17bR)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-2H,6H,7H,8H,9H,12H,14aH,15H,17bH-1,3-dioxacyclotrideca[5,4-e]isoindole-2,7-dione

Traditional Name

(6S,8R,12R,14aR,15R,17aR,17bR)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-8H,9H,12H,14aH,15H,17bH-1,3-dioxacyclotrideca[5,4-e]isoindole-2,7-dione

CAS Registry Number

Not Available

SMILES

COC1=CC=C(C[C@H]2N=C(O)[C@]34OC(=O)O\C=C\[C@](C)(O)C(=O)[C@H](C)C\C=C\[C@@H]3[C@@H](O)C(C)=C(C)[C@H]24)C=C1

InChI Identifier

InChI=1S/C29H35NO8/c1-16-7-6-8-21-24(31)18(3)17(2)23-22(15-19-9-11-20(36-5)12-10-19)30-26(33)29(21,23)38-27(34)37-14-13-28(4,35)25(16)32/h6,8-14,16,21-24,31,35H,7,15H2,1-5H3,(H,30,33)/b8-6+,14-13+/t16-,21-,22-,23-,24+,28+,29+/m1/s1

InChI Key

UKXQRSOMKIGRCJ-ZLVRRUFZSA-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
Garcinia dulcis	LOTUS Database	35616633
Peroneutypa scoparia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindoles. These are heteropolycyclic compounds with a structure containing isoindole, a benzo-fused pyrrole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Isoindoles

Direct Parent

Isoindoles

Alternative Parents

Substituents

Isoindole
Phenoxy compound
Anisole
Phenol ether
Methoxybenzene
Alkyl aryl ether
Acyloin
Monocyclic benzene moiety
Carbonic acid diester
Benzenoid
Enol ester
Pyrroline
Tertiary alcohol
Cyclic carboximidic acid
Cyclic ketone
Secondary alcohol
Ketone
Carbonic acid derivative
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Ether
Oxacycle
Polyol
Azacycle
Organopnictogen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Alcohol
Organonitrogen compound
Organooxygen 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	2.54	ChemAxon
pKa (Strongest Acidic)	1.5	ChemAxon
pKa (Strongest Basic)	4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	134.88 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	140.88 m³·mol⁻¹	ChemAxon
Polarizability	53.59 Å³	ChemAxon
Number of Rings	4	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

C00041857

Chemspider ID

78438664

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

139588624

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (6s,8r,11ar,12r,14ar,15r,17ar)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-8h,9h,11ah,12h,14ah,15h-1,3-dioxacyclotrideca[4,5-d]isoindole-2,7-dione (NP0226470)

MOL for NP0226470 ((6s,8r,11ar,12r,14ar,15r,17ar)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-8h,9h,11ah,12h,14ah,15h-1,3-dioxacyclotrideca[4,5-d]isoindole-2,7-dione)

3D MOL for NP0226470 ((6s,8r,11ar,12r,14ar,15r,17ar)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-8h,9h,11ah,12h,14ah,15h-1,3-dioxacyclotrideca[4,5-d]isoindole-2,7-dione)

3D SDF for NP0226470 ((6s,8r,11ar,12r,14ar,15r,17ar)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-8h,9h,11ah,12h,14ah,15h-1,3-dioxacyclotrideca[4,5-d]isoindole-2,7-dione)

3D-SDF for NP0226470 ((6s,8r,11ar,12r,14ar,15r,17ar)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-8h,9h,11ah,12h,14ah,15h-1,3-dioxacyclotrideca[4,5-d]isoindole-2,7-dione)

PDB for NP0226470 ((6s,8r,11ar,12r,14ar,15r,17ar)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-8h,9h,11ah,12h,14ah,15h-1,3-dioxacyclotrideca[4,5-d]isoindole-2,7-dione)

3D PDB for NP0226470 ((6s,8r,11ar,12r,14ar,15r,17ar)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-8h,9h,11ah,12h,14ah,15h-1,3-dioxacyclotrideca[4,5-d]isoindole-2,7-dione)

SMILES for NP0226470 ((6s,8r,11ar,12r,14ar,15r,17ar)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-8h,9h,11ah,12h,14ah,15h-1,3-dioxacyclotrideca[4,5-d]isoindole-2,7-dione)

INCHI for NP0226470 ((6s,8r,11ar,12r,14ar,15r,17ar)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-8h,9h,11ah,12h,14ah,15h-1,3-dioxacyclotrideca[4,5-d]isoindole-2,7-dione)

Structure for NP0226470 ((6s,8r,11ar,12r,14ar,15r,17ar)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-8h,9h,11ah,12h,14ah,15h-1,3-dioxacyclotrideca[4,5-d]isoindole-2,7-dione)

3D Structure for NP0226470 ((6s,8r,11ar,12r,14ar,15r,17ar)-6,12,17-trihydroxy-15-[(4-methoxyphenyl)methyl]-6,8,13,14-tetramethyl-8h,9h,11ah,12h,14ah,15h-1,3-dioxacyclotrideca[4,5-d]isoindole-2,7-dione)