NP-MRD: Showing NP-Card for 4-[(1r,2s,4r,5s,6r,9s,10r,13s,15s)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-6-yl]-5h-furan-2-one (NP0223947)

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Record Information

Version

2.0

Created at

2022-09-06 02:11:05 UTC

Updated at

2022-09-06 02:11:05 UTC

NP-MRD ID

NP0223947

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-[(1r,2s,4r,5s,6r,9s,10r,13s,15s)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-6-yl]-5h-furan-2-one

Description

4-[(1R,2S,4R,5S,6R,9S,10R,13S,15S)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0¹,¹³.0²,¹⁰.0⁵,⁹]Nonadecan-6-yl]-2,5-dihydrofuran-2-one belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative. 4-[(1r,2s,4r,5s,6r,9s,10r,13s,15s)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-6-yl]-5h-furan-2-one is found in Asclepias curassavica. Based on a literature review very few articles have been published on 4-[(1R,2S,4R,5S,6R,9S,10R,13S,15S)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0¹,¹³.0²,¹⁰.0⁵,⁹]Nonadecan-6-yl]-2,5-dihydrofuran-2-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062204112D          

 30 35  0  0  1  0            999 V2000
   -1.6450    0.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0368    0.0880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2500    0.3361    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2167    1.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3385    0.4683    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2061    1.2209    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5740    0.5432    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1395   -0.3897    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6829   -1.0696    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5130   -0.9374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8679   -0.1767    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2432    0.3621    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3975    1.1726    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1765    1.4442    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.3308    2.2546    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8012    0.9053    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.0394    1.6952    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6197    1.0090    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0169    1.7321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6654    2.4784    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2666    3.0434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1629    3.8619    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9897    2.6462    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.8353    1.8358    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9712    0.2626    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3700   -0.3023    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6469    0.0949    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5782   -0.7273    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  3  8  1  0  0  0  0
  6  9  1  0  0  0  0
  9 10  1  1  0  0  0
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  9 30  1  0  0  0  0
  3 30  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309062204112D          

 30 35  0  0  1  0            999 V2000
   -1.6450    0.6453    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0368    0.0880    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.2167    1.1720    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6168    1.1163    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0223947

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@]12CC[C@@]3(CO1)[C@@H](CC[C@@H]1[C@@H]3C[C@@H](O)[C@]3(C)[C@H](CC[C@]13O)C1=CC(=O)OC1)C2

> <INCHI_IDENTIFIER>
InChI=1S/C24H34O6/c1-21-16(14-9-20(26)29-12-14)5-6-24(21,27)17-4-3-15-11-23(28-2)8-7-22(15,13-30-23)18(17)10-19(21)25/h9,15-19,25,27H,3-8,10-13H2,1-2H3/t15-,16+,17+,18-,19+,21-,22+,23-,24-/m0/s1

> <INCHI_KEY>
GFPPTQYNSHRMQH-IMVRBGBTSA-N

> <FORMULA>
C24H34O6

> <MOLECULAR_WEIGHT>
418.53

> <EXACT_MASS>
418.235538815

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
45.567396419451086

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-[(1R,2S,4R,5S,6R,9S,10R,13S,15S)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0^{1,13}.0^{2,10}.0^{5,9}]nonadecan-6-yl]-2,5-dihydrofuran-2-one

> <JCHEM_LOGP>
1.7135154656666658

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.97169679565733

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.151116396616132

> <JCHEM_PKA_STRONGEST_BASIC>
-2.976132980663439

> <JCHEM_POLAR_SURFACE_AREA>
85.22

> <JCHEM_REFRACTIVITY>
109.85999999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
4-[(1R,2S,4R,5S,6R,9S,10R,13S,15S)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0^{1,13}.0^{2,10}.0^{5,9}]nonadecan-6-yl]-5H-furan-2-one

> <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      -3.071   1.205   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      -1.935   0.164   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      -0.467   0.627   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.405   2.188   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.151   2.084   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.499   0.874   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.251   2.279   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       1.071   1.014   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       2.127  -0.727   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.141  -1.997   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.691  -1.750   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.353  -0.330   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.187   0.676   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.475   2.189   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.930   2.696   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       6.218   4.209   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       7.096   1.690   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.540   3.164   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.623   1.883   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.365   3.233   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.709   4.626   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.831   5.681   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       9.637   7.209   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      11.181   4.940   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      10.893   3.427   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       9.280   0.490   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       8.157  -0.564   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.808   0.177   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.679  -1.358   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       0.494  -0.634   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    8   30                                             
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    9   13                                             
CONECT    7    6    8                                                       
CONECT    8    7    3                                                       
CONECT    9    6   10   30                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   28                                                  
CONECT   13   12    6   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19   28                                             
CONECT   18   17                                                            
CONECT   19   17   20   26                                                  
CONECT   20   19   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   20                                                       
CONECT   26   19   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   12   17   29                                             
CONECT   29   28                                                            
CONECT   30    9    3                                                       
MASTER        0    0    0    0    0    0    0    0   30    0   70    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₃₄O₆

Average Mass

418.5300 Da

Monoisotopic Mass

418.23554 Da

IUPAC Name

4-[(1R,2S,4R,5S,6R,9S,10R,13S,15S)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0^{1,13}.0^{2,10}.0^{5,9}]nonadecan-6-yl]-2,5-dihydrofuran-2-one

Traditional Name

4-[(1R,2S,4R,5S,6R,9S,10R,13S,15S)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0^{1,13}.0^{2,10}.0^{5,9}]nonadecan-6-yl]-5H-furan-2-one

CAS Registry Number

Not Available

SMILES

CO[C@@]12CC[C@@]3(CO1)[C@@H](CC[C@@H]1[C@@H]3C[C@@H](O)[C@]3(C)[C@H](CC[C@]13O)C1=CC(=O)OC1)C2

InChI Identifier

InChI=1S/C24H34O6/c1-21-16(14-9-20(26)29-12-14)5-6-24(21,27)17-4-3-15-11-23(28-2)8-7-22(15,13-30-23)18(17)10-19(21)25/h9,15-19,25,27H,3-8,10-13H2,1-2H3/t15-,16+,17+,18-,19+,21-,22+,23-,24-/m0/s1

InChI Key

GFPPTQYNSHRMQH-IMVRBGBTSA-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
Asclepias curassavica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cardenolides and derivatives. These are steroid lactones containing a furan-2-one moiety linked to the C17 atom of a cyclopenta[a]phenanthrene derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Cardenolides and derivatives

Alternative Parents

Substituents

Cardanolide-skeleton
Naphthopyran
Naphthalene
Ketal
2-furanone
Oxane
Pyran
Cyclic alcohol
Dihydrofuran
Alpha,beta-unsaturated carboxylic ester
Tertiary alcohol
Enoate ester
Lactone
Carboxylic acid ester
Secondary alcohol
Oxacycle
Monocarboxylic acid or derivatives
Acetal
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Alcohol
Organic oxide
Organic oxygen compound
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	1.71	ChemAxon
pKa (Strongest Acidic)	7.15	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	85.22 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	109.86 m³·mol⁻¹	ChemAxon
Polarizability	45.57 Å³	ChemAxon
Number of Rings	6	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

163020300

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-[(1r,2s,4r,5s,6r,9s,10r,13s,15s)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-6-yl]-5h-furan-2-one (NP0223947)

MOL for NP0223947 (4-[(1r,2s,4r,5s,6r,9s,10r,13s,15s)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-6-yl]-5h-furan-2-one)

3D MOL for NP0223947 (4-[(1r,2s,4r,5s,6r,9s,10r,13s,15s)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-6-yl]-5h-furan-2-one)

3D SDF for NP0223947 (4-[(1r,2s,4r,5s,6r,9s,10r,13s,15s)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-6-yl]-5h-furan-2-one)

3D-SDF for NP0223947 (4-[(1r,2s,4r,5s,6r,9s,10r,13s,15s)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-6-yl]-5h-furan-2-one)

PDB for NP0223947 (4-[(1r,2s,4r,5s,6r,9s,10r,13s,15s)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-6-yl]-5h-furan-2-one)

3D PDB for NP0223947 (4-[(1r,2s,4r,5s,6r,9s,10r,13s,15s)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-6-yl]-5h-furan-2-one)

SMILES for NP0223947 (4-[(1r,2s,4r,5s,6r,9s,10r,13s,15s)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-6-yl]-5h-furan-2-one)

INCHI for NP0223947 (4-[(1r,2s,4r,5s,6r,9s,10r,13s,15s)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-6-yl]-5h-furan-2-one)

Structure for NP0223947 (4-[(1r,2s,4r,5s,6r,9s,10r,13s,15s)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-6-yl]-5h-furan-2-one)

3D Structure for NP0223947 (4-[(1r,2s,4r,5s,6r,9s,10r,13s,15s)-4,9-dihydroxy-15-methoxy-5-methyl-16-oxapentacyclo[13.2.2.0¹,¹³.0²,¹⁰.0⁵,⁹]nonadecan-6-yl]-5h-furan-2-one)