NP-MRD: Showing NP-Card for (1s,2s,11s,13s)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,15,17,19-hexaene-3,10,14,21-tetrone (NP0329409)

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Record Information

Version

2.0

Created at

2022-09-12 13:45:30 UTC

Updated at

2022-09-12 13:45:30 UTC

NP-MRD ID

NP0329409

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2s,11s,13s)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,15,17,19-hexaene-3,10,14,21-tetrone

Description

Hybocarpone belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. (1s,2s,11s,13s)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,15,17,19-hexaene-3,10,14,21-tetrone is found in Lecanora hybocarpa. It was first documented in 2004 (PMID: 14719960). Based on a literature review a small amount of articles have been published on Hybocarpone (PMID: 16438511) (PMID: 30484314) (PMID: 25632480) (PMID: 17415880).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309122215452D          

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M  END

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M  END


  Mrv1652309122215452D          

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  3 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 23 24  2  0  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  2  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  2  0  0  0  0
 25 34  1  0  0  0  0
 34 35  1  0  0  0  0
 35 36  2  0  0  0  0
 35 37  1  0  0  0  0
 21 37  1  0  0  0  0
  3 37  1  0  0  0  0
 37 38  1  1  0  0  0
 38 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0329409

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC[C@]12C(=O)C3=C(O)C(C)=C(O)C(O)=C3C(=O)[C@@]1(O)O[C@]1(O)C(=O)C3=C(O)C(O)=C(C)C(O)=C3C(=O)[C@]21CC

> <INCHI_IDENTIFIER>
InChI=1S/C26H24O13/c1-5-23-19(33)9-11(17(31)15(29)7(3)13(9)27)21(35)25(23,37)39-26(38)22(36)12-10(20(34)24(23,26)6-2)14(28)8(4)16(30)18(12)32/h27-32,37-38H,5-6H2,1-4H3/t23-,24-,25-,26-/m1/s1

> <INCHI_KEY>
MZNMSRGMWTWFRF-VEYUFSJPSA-N

> <FORMULA>
C26H24O13

> <MOLECULAR_WEIGHT>
544.465

> <EXACT_MASS>
544.121690833

> <JCHEM_ACCEPTOR_COUNT>
13

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
51.05476370771411

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
8

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2S,11S,13S)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-4(9),5,7,15(20),16,18-hexaene-3,10,14,21-tetrone

> <JCHEM_LOGP>
5.469621739

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.1428395805456

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.566796655909462

> <JCHEM_PKA_STRONGEST_BASIC>
-5.178304607805511

> <JCHEM_POLAR_SURFACE_AREA>
239.34999999999997

> <JCHEM_REFRACTIVITY>
130.79409999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2S,11S,13S)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-4(9),5,7,15(20),16,18-hexaene-3,10,14,21-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 12-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   12-SEP-22         0                                  
HETATM    1  C   UNK     0       5.138   2.359   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.865   2.020   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.917   0.266   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.947   1.410   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       7.170   3.187   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       9.454   1.090   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      10.484   2.235   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      10.620   3.875   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      11.990   1.914   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      13.099   3.065   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      12.466   0.450   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      14.027   0.127   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      11.436  -0.695   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      12.147  -2.125   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.930  -0.374   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.899  -1.519   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       9.682  -2.919   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       7.393  -1.199   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       7.744  -2.800   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0       6.147  -2.104   0.000  0.00  0.00           O+0
HETATM   21  C   UNK     0       4.901  -1.199   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       4.550  -2.800   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       3.395  -1.519   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       2.611  -2.919   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       2.364  -0.374   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.858  -0.695   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       0.146  -2.125   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0      -0.173   0.450   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -1.733   0.127   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.303   1.914   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.801   3.069   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.810   2.235   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       1.743   3.847   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       2.840   1.090   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.346   1.410   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.272   3.238   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       5.377   0.266   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       6.044   1.721   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       7.807   2.310   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   18   37                                             
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   15                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13    6   16                                                  
CONECT   16   15   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16    3   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22   23   37                                             
CONECT   22   21                                                            
CONECT   23   21   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   26   34                                                  
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   25   35                                                  
CONECT   35   34   36   37                                                  
CONECT   36   35                                                            
CONECT   37   35   21    3   38                                             
CONECT   38   37   39                                                       
CONECT   39   38                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₂₄O₁₃

Average Mass

544.4650 Da

Monoisotopic Mass

544.12169 Da

IUPAC Name

(1S,2S,11S,13S)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-4(9),5,7,15(20),16,18-hexaene-3,10,14,21-tetrone

Traditional Name

(1S,2S,11S,13S)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0^{2,11}.0^{4,9}.0^{15,20}]henicosa-4(9),5,7,15(20),16,18-hexaene-3,10,14,21-tetrone

CAS Registry Number

Not Available

SMILES

CC[C@]12C(=O)C3=C(O)C(C)=C(O)C(O)=C3C(=O)[C@@]1(O)O[C@]1(O)C(=O)C3=C(O)C(O)=C(C)C(O)=C3C(=O)[C@]21CC

InChI Identifier

InChI=1S/C26H24O13/c1-5-23-19(33)9-11(17(31)15(29)7(3)13(9)27)21(35)25(23,37)39-26(38)22(36)12-10(20(34)24(23,26)6-2)14(28)8(4)16(30)18(12)32/h27-32,37-38H,5-6H2,1-4H3/t23-,24-,25-,26-/m1/s1

InChI Key

MZNMSRGMWTWFRF-VEYUFSJPSA-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
Lecanora hybocarpa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
Naphthoquinone
Naphthalene
Tetralin
Quinone
Aryl ketone
Aryl alkyl ketone
Phenol
Benzenoid
Oxolane
Vinylogous acid
Hemiacetal
Ketone
Oxacycle
Polyol
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
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	5.47	ChemAxon
pKa (Strongest Acidic)	7.57	ChemAxon
pKa (Strongest Basic)	-5.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	13	ChemAxon
Hydrogen Donor Count	8	ChemAxon
Polar Surface Area	239.35 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	130.79 m³·mol⁻¹	ChemAxon
Polarizability	51.05 Å³	ChemAxon
Number of Rings	5	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

8635442

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10460029

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Chai CL, Elix JA, Moore FK: Concise formal total synthesis of hybocarpone and related naturally occurring naphthazarins. J Org Chem. 2006 Feb 3;71(3):992-1001. doi: 10.1021/jo0519561. [PubMed:16438511 ]
Chen W, Guo R, Yang Z, Gong J: Formal Total Synthesis of Hybocarpone Enabled by Visible-Light-Promoted Benzannulation. J Org Chem. 2018 Dec 21;83(24):15524-15532. doi: 10.1021/acs.joc.8b02595. Epub 2018 Dec 12. [PubMed:30484314 ]
Dragana SV, Pushilin MA, Glazunov VP, Denisenko VA, Anufriev VP: Total synthesis of hybocarpone, a cytotoxic naphthazarin derivative from the lichen Lecanora hybocarpa, and related compounds. Nat Prod Commun. 2014 Dec;9(12):1765-8. [PubMed:25632480 ]
Kokubun T, Shiu WK, Gibbons S: Inhibitory activities of lichen-derived compounds against methicillin- and multidrug-resistant Staphylococcus aureus. Planta Med. 2007 Feb;73(2):176-9. doi: 10.1055/s-2006-957070. [PubMed:17415880 ]
Nicolaou KC, Gray DL: Total synthesis of hybocarpone and analogues thereof. A facile dimerization of naphthazarins to pentacyclic systems. J Am Chem Soc. 2004 Jan 21;126(2):607-12. doi: 10.1021/ja030497n. [PubMed:14719960 ]
LOTUS database [Link]

Showing NP-Card for (1s,2s,11s,13s)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,15,17,19-hexaene-3,10,14,21-tetrone (NP0329409)

MOL for NP0329409 ((1s,2s,11s,13s)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,15,17,19-hexaene-3,10,14,21-tetrone)

3D MOL for NP0329409 ((1s,2s,11s,13s)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,15,17,19-hexaene-3,10,14,21-tetrone)

3D SDF for NP0329409 ((1s,2s,11s,13s)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,15,17,19-hexaene-3,10,14,21-tetrone)

3D-SDF for NP0329409 ((1s,2s,11s,13s)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,15,17,19-hexaene-3,10,14,21-tetrone)

PDB for NP0329409 ((1s,2s,11s,13s)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,15,17,19-hexaene-3,10,14,21-tetrone)

3D PDB for NP0329409 ((1s,2s,11s,13s)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,15,17,19-hexaene-3,10,14,21-tetrone)

SMILES for NP0329409 ((1s,2s,11s,13s)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,15,17,19-hexaene-3,10,14,21-tetrone)

INCHI for NP0329409 ((1s,2s,11s,13s)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,15,17,19-hexaene-3,10,14,21-tetrone)

Structure for NP0329409 ((1s,2s,11s,13s)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,15,17,19-hexaene-3,10,14,21-tetrone)

3D Structure for NP0329409 ((1s,2s,11s,13s)-1,2-diethyl-5,7,8,11,13,16,17,19-octahydroxy-6,18-dimethyl-12-oxapentacyclo[11.8.0.0²,¹¹.0⁴,⁹.0¹⁵,²⁰]henicosa-4,6,8,15,17,19-hexaene-3,10,14,21-tetrone)