NP-MRD: Showing NP-Card for (5e,9s,10s,13r,17z)-13-ethyl-3,10,23-trihydroxy-6,19-dimethyl-9-(2-methylprop-1-en-1-yl)-8,26-dioxa-2-azatricyclo[16.6.2.0²¹,²⁵]hexacosa-1(24),2,5,11,17,19,21(25),22-octaene-7,16-dione (NP0203976)

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Record Information

Version

2.0

Created at

2022-09-04 23:33:54 UTC

Updated at

2022-09-04 23:33:54 UTC

NP-MRD ID

NP0203976

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(5e,9s,10s,13r,17z)-13-ethyl-3,10,23-trihydroxy-6,19-dimethyl-9-(2-methylprop-1-en-1-yl)-8,26-dioxa-2-azatricyclo[16.6.2.0²¹,²⁵]hexacosa-1(24),2,5,11,17,19,21(25),22-octaene-7,16-dione

Description

Divergolide B belongs to the class of organic compounds known as 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position. Based on a literature review very few articles have been published on Divergolide B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052201332D          

 39 41  0  0  1  0            999 V2000
   11.1294    3.0929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   12.7430   -0.8787    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309052201332D          

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    9.3743    0.8374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2519    1.9652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.9030    1.4585    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4210    2.3574    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5343    3.1746    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6567    2.0469    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  3  2  1  1  0  0  0
  3  4  1  0  0  0  0
  4  5  2  3  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
  8 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
 16 18  2  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
 20 22  2  0  0  0  0
 22 23  1  4  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  2  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
 35 36  1  0  0  0  0
  3 36  1  0  0  0  0
 31 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
 28 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0203976

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@@H]1CCC(=O)\C=C2/OC3=C(C=C(O)C=C3N=C(O)C\C=C(C)\C(=O)O[C@@H](C=C(C)C)[C@@H](O)C=C1)C=C2C

> <INCHI_IDENTIFIER>
InChI=1S/C31H37NO7/c1-6-21-8-10-23(33)17-27-20(5)14-22-15-24(34)16-25(30(22)38-27)32-29(36)12-7-19(4)31(37)39-28(13-18(2)3)26(35)11-9-21/h7,9,11,13-17,21,26,28,34-35H,6,8,10,12H2,1-5H3,(H,32,36)/b11-9?,19-7+,27-17-/t21-,26+,28+/m1/s1

> <INCHI_KEY>
GGEGLRHQJXGBSH-CCSZFJTGSA-N

> <FORMULA>
C31H37NO7

> <MOLECULAR_WEIGHT>
535.637

> <EXACT_MASS>
535.257002535

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
76

> <JCHEM_AVERAGE_POLARIZABILITY>
57.564015799398256

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(5E,9S,10S,13R)-13-ethyl-3,10,23-trihydroxy-6,19-dimethyl-9-(2-methylprop-1-en-1-yl)-8,26-dioxa-2-azatricyclo[16.6.2.0^{21,25}]hexacosa-1(25),2,5,11,17,19,21,23-octaene-7,16-dione

> <JCHEM_LOGP>
5.976643755

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
9.649900132031012

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.81250154325098

> <JCHEM_PKA_STRONGEST_BASIC>
-0.38041786507569497

> <JCHEM_POLAR_SURFACE_AREA>
125.65

> <JCHEM_REFRACTIVITY>
156.18000000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(5E,9S,10S,13R)-13-ethyl-3,10,23-trihydroxy-6,19-dimethyl-9-(2-methylprop-1-en-1-yl)-8,26-dioxa-2-azatricyclo[16.6.2.0^{21,25}]hexacosa-1(25),2,5,11,17,19,21,23-octaene-7,16-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      20.775   5.773   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      21.990   4.828   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      21.779   3.302   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      22.994   2.356   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      22.783   0.831   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      23.998  -0.115   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      25.425   0.465   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0      23.787  -1.640   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.002  -2.586   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      24.791  -4.111   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      26.006  -5.057   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      23.364  -4.691   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      22.360  -2.220   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      21.145  -1.274   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      21.356   0.251   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      19.718  -1.854   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      19.507  -3.379   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      18.503  -0.908   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      17.076  -1.488   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      15.861  -0.542   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      16.072   0.984   0.000  0.00  0.00           O+0
HETATM   22  N   UNK     0      14.434  -1.122   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      13.218  -0.176   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      11.792  -0.755   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      10.576   0.190   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       9.150  -0.389   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      10.788   1.716   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      12.214   2.295   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.430   1.350   0.000  0.00  0.00           C+0
HETATM   30  O   UNK     0      14.857   1.929   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0      15.068   3.455   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      16.495   4.034   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      17.710   3.089   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0      17.499   1.563   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      19.137   3.668   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0      20.352   2.723   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      13.853   4.401   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      14.064   5.926   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0      12.426   3.821   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   36                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   13                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13    8   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29   39                                                  
CONECT   29   28   23   30                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32   37                                                  
CONECT   32   31   33                                                       
CONECT   33   32   34   35                                                  
CONECT   34   33                                                            
CONECT   35   33   36                                                       
CONECT   36   35    3                                                       
CONECT   37   31   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37   28                                                       
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₁H₃₇NO₇

Average Mass

535.6370 Da

Monoisotopic Mass

535.25700 Da

IUPAC Name

(5E,9S,10S,13R)-13-ethyl-3,10,23-trihydroxy-6,19-dimethyl-9-(2-methylprop-1-en-1-yl)-8,26-dioxa-2-azatricyclo[16.6.2.0^{21,25}]hexacosa-1(25),2,5,11,17,19,21,23-octaene-7,16-dione

Traditional Name

(5E,9S,10S,13R)-13-ethyl-3,10,23-trihydroxy-6,19-dimethyl-9-(2-methylprop-1-en-1-yl)-8,26-dioxa-2-azatricyclo[16.6.2.0^{21,25}]hexacosa-1(25),2,5,11,17,19,21,23-octaene-7,16-dione

CAS Registry Number

Not Available

SMILES

CC[C@@H]1CCC(=O)\C=C2/OC3=C(C=C(O)C=C3N=C(O)C\C=C(C)\C(=O)O[C@@H](C=C(C)C)[C@@H](O)C=C1)C=C2C

InChI Identifier

InChI=1S/C31H37NO7/c1-6-21-8-10-23(33)17-27-20(5)14-22-15-24(34)16-25(30(22)38-27)32-29(36)12-7-19(4)31(37)39-28(13-18(2)3)26(35)11-9-21/h7,9,11,13-17,21,26,28,34-35H,6,8,10,12H2,1-5H3,(H,32,36)/b11-9?,19-7+,27-17-/t21-,26+,28+/m1/s1

InChI Key

GGEGLRHQJXGBSH-CCSZFJTGSA-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 1-benzopyrans. These are organic aromatic compounds that 1-benzopyran, a bicyclic compound made up of a benzene ring fused to a pyran, so that the oxygen atom is at the 1-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

1-benzopyrans

Alternative Parents

Substituents

1-benzopyran
1-hydroxy-2-unsubstituted benzenoid
Benzenoid
Vinylogous ester
Cyclic carboximidic acid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Cyclic ketone
Secondary alcohol
Lactone
Ketone
Carboxylic acid ester
Oxacycle
Azacycle
Organic 1,3-dipolar compound
Propargyl-type 1,3-dipolar organic compound
Polyol
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen 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	5.98	ChemAxon
pKa (Strongest Acidic)	4.81	ChemAxon
pKa (Strongest Basic)	-0.38	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	125.65 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	156.18 m³·mol⁻¹	ChemAxon
Polarizability	57.56 Å³	ChemAxon
Number of Rings	3	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

102590736

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (5e,9s,10s,13r,17z)-13-ethyl-3,10,23-trihydroxy-6,19-dimethyl-9-(2-methylprop-1-en-1-yl)-8,26-dioxa-2-azatricyclo[16.6.2.0²¹,²⁵]hexacosa-1(24),2,5,11,17,19,21(25),22-octaene-7,16-dione (NP0203976)

MOL for NP0203976 ((5e,9s,10s,13r,17z)-13-ethyl-3,10,23-trihydroxy-6,19-dimethyl-9-(2-methylprop-1-en-1-yl)-8,26-dioxa-2-azatricyclo[16.6.2.0²¹,²⁵]hexacosa-1(24),2,5,11,17,19,21(25),22-octaene-7,16-dione)

3D MOL for NP0203976 ((5e,9s,10s,13r,17z)-13-ethyl-3,10,23-trihydroxy-6,19-dimethyl-9-(2-methylprop-1-en-1-yl)-8,26-dioxa-2-azatricyclo[16.6.2.0²¹,²⁵]hexacosa-1(24),2,5,11,17,19,21(25),22-octaene-7,16-dione)

3D SDF for NP0203976 ((5e,9s,10s,13r,17z)-13-ethyl-3,10,23-trihydroxy-6,19-dimethyl-9-(2-methylprop-1-en-1-yl)-8,26-dioxa-2-azatricyclo[16.6.2.0²¹,²⁵]hexacosa-1(24),2,5,11,17,19,21(25),22-octaene-7,16-dione)

3D-SDF for NP0203976 ((5e,9s,10s,13r,17z)-13-ethyl-3,10,23-trihydroxy-6,19-dimethyl-9-(2-methylprop-1-en-1-yl)-8,26-dioxa-2-azatricyclo[16.6.2.0²¹,²⁵]hexacosa-1(24),2,5,11,17,19,21(25),22-octaene-7,16-dione)

PDB for NP0203976 ((5e,9s,10s,13r,17z)-13-ethyl-3,10,23-trihydroxy-6,19-dimethyl-9-(2-methylprop-1-en-1-yl)-8,26-dioxa-2-azatricyclo[16.6.2.0²¹,²⁵]hexacosa-1(24),2,5,11,17,19,21(25),22-octaene-7,16-dione)

3D PDB for NP0203976 ((5e,9s,10s,13r,17z)-13-ethyl-3,10,23-trihydroxy-6,19-dimethyl-9-(2-methylprop-1-en-1-yl)-8,26-dioxa-2-azatricyclo[16.6.2.0²¹,²⁵]hexacosa-1(24),2,5,11,17,19,21(25),22-octaene-7,16-dione)

SMILES for NP0203976 ((5e,9s,10s,13r,17z)-13-ethyl-3,10,23-trihydroxy-6,19-dimethyl-9-(2-methylprop-1-en-1-yl)-8,26-dioxa-2-azatricyclo[16.6.2.0²¹,²⁵]hexacosa-1(24),2,5,11,17,19,21(25),22-octaene-7,16-dione)

INCHI for NP0203976 ((5e,9s,10s,13r,17z)-13-ethyl-3,10,23-trihydroxy-6,19-dimethyl-9-(2-methylprop-1-en-1-yl)-8,26-dioxa-2-azatricyclo[16.6.2.0²¹,²⁵]hexacosa-1(24),2,5,11,17,19,21(25),22-octaene-7,16-dione)

Structure for NP0203976 ((5e,9s,10s,13r,17z)-13-ethyl-3,10,23-trihydroxy-6,19-dimethyl-9-(2-methylprop-1-en-1-yl)-8,26-dioxa-2-azatricyclo[16.6.2.0²¹,²⁵]hexacosa-1(24),2,5,11,17,19,21(25),22-octaene-7,16-dione)

3D Structure for NP0203976 ((5e,9s,10s,13r,17z)-13-ethyl-3,10,23-trihydroxy-6,19-dimethyl-9-(2-methylprop-1-en-1-yl)-8,26-dioxa-2-azatricyclo[16.6.2.0²¹,²⁵]hexacosa-1(24),2,5,11,17,19,21(25),22-octaene-7,16-dione)