NP-MRD: Showing NP-Card for (3r,4e,8z)-1-[(3e,4s,5r)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(e,z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate (NP0317201)

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Record Information

Version

2.0

Created at

2022-09-11 16:54:53 UTC

Updated at

2022-09-11 16:54:53 UTC

NP-MRD ID

NP0317201

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(3r,4e,8z)-1-[(3e,4s,5r)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(e,z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate

Description

(3R,4E,8Z)-1-[(3E,4S,5R)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(E,Z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate belongs to the class of organic compounds known as diterpene lactones. These are diterpenoids containing a lactone moiety. Based on a literature review very few articles have been published on (3R,4E,8Z)-1-[(3E,4S,5R)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(E,Z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112218542D          

 39 40  0  0  1  0            999 V2000
    2.1353   -4.0104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  1  2  1  0  0  0  0
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 37 39  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309112218542D          

 39 40  0  0  1  0            999 V2000
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   -1.4289  -14.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289  -13.2000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3819   -4.0526    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1665   -4.3075    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1270   -3.2680    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3020   -3.2680    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1830   -2.6005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1526   -1.8468    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9731   -1.7606    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3323   -1.1794    0.0000 C   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
  2  4  1  0  0  0  0
  5  4  1  1  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  1  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  2  0  0  0  0
  9 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 19 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 29 30  1  0  0  0  0
 30 31  2  0  0  0  0
 26 31  1  0  0  0  0
  6 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  1  6  0  0  0
 36 37  2  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0317201

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=C[C@H]1OC(=O)\C(=C\C[C@@H](OC(C)=O)C(\C)=C\CC\C(C)=C/COC(=O)C2=CC=CC=C2)[C@@H]1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C31H38O8/c1-20(2)19-28-29(38-24(6)33)26(31(35)39-28)15-16-27(37-23(5)32)22(4)12-10-11-21(3)17-18-36-30(34)25-13-8-7-9-14-25/h7-9,12-15,17,19,27-29H,10-11,16,18H2,1-6H3/b21-17-,22-12+,26-15+/t27-,28-,29+/m1/s1

> <INCHI_KEY>
FMYFGWHRNXSKJT-RGLUGEENSA-N

> <FORMULA>
C31H38O8

> <MOLECULAR_WEIGHT>
538.637

> <EXACT_MASS>
538.256668184

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
57.842268650883156

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(3R,4E,8Z)-1-[(3E,4S,5R)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(E,Z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate

> <JCHEM_LOGP>
5.908241291333335

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.37068020508038

> <JCHEM_POLAR_SURFACE_AREA>
105.2

> <JCHEM_REFRACTIVITY>
149.37580000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(3R,4E,8Z)-1-[(3E,4S,5R)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(E,Z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       3.986  -7.486   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.521  -7.010   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       2.201  -5.504   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       1.377  -8.041   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      -0.088  -7.565   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334  -8.470   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334 -10.010   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000 -10.780   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000 -12.320   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.334 -13.090   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667 -10.780   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       4.001 -13.090   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.334 -13.090   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667 -12.320   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.334 -14.630   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -2.667 -15.400   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -2.667 -16.940   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      -4.001 -17.710   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      -5.335 -16.940   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      -4.001 -19.250   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -2.667 -20.020   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      -2.667 -21.560   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0      -1.334 -22.330   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.000 -21.560   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.334 -23.870   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       0.000 -24.640   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.000 -26.180   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -1.334 -26.950   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -2.667 -26.180   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -2.667 -24.640   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -2.580  -7.565   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -4.044  -8.041   0.000  0.00  0.00           O+0
HETATM   34  O   UNK     0      -2.104  -6.100   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0      -0.564  -6.100   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       0.342  -4.854   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0      -0.285  -3.447   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0      -1.816  -3.286   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       0.620  -2.202   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7   32                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    9   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   31                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   31                                                       
CONECT   31   30   26                                                       
CONECT   32    6   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34    5   36                                                  
CONECT   36   35   37                                                       
CONECT   37   36   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   80    0
END

View in JSmol

Synonyms

Value	Source
(3R,4E,8Z)-1-[(3E,4S,5R)-4-(Acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(e,Z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetic acid	Generator

Chemical Formula

C₃₁H₃₈O₈

Average Mass

538.6370 Da

Monoisotopic Mass

538.25667 Da

IUPAC Name

(3R,4E,8Z)-1-[(3E,4S,5R)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(E,Z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate

Traditional Name

(3R,4E,8Z)-1-[(3E,4S,5R)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(E,Z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC(C)=C[C@H]1OC(=O)\C(=C\C[C@@H](OC(C)=O)C(\C)=C\CC\C(C)=C/COC(=O)C2=CC=CC=C2)[C@@H]1OC(C)=O

InChI Identifier

InChI=1S/C31H38O8/c1-20(2)19-28-29(38-24(6)33)26(31(35)39-28)15-16-27(37-23(5)32)22(4)12-10-11-21(3)17-18-36-30(34)25-13-8-7-9-14-25/h7-9,12-15,17,19,27-29H,10-11,16,18H2,1-6H3/b21-17-,22-12+,26-15+/t27-,28-,29+/m1/s1

InChI Key

FMYFGWHRNXSKJT-RGLUGEENSA-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 diterpene lactones. These are diterpenoids containing a lactone moiety.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Diterpene lactones

Alternative Parents

Substituents

Diterpene lactone
Diterpenoid
Tetracarboxylic acid or derivatives
Fatty alcohol ester
Benzoate ester
Benzoic acid or derivatives
Benzoyl
Monocyclic benzene moiety
Benzenoid
Gamma butyrolactone
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Tetrahydrofuran
Carboxylic acid ester
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic 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	5.91	ChemAxon
pKa (Strongest Basic)	-6.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	105.2 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	149.38 m³·mol⁻¹	ChemAxon
Polarizability	57.84 Å³	ChemAxon
Number of Rings	2	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

163187749

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (3r,4e,8z)-1-[(3e,4s,5r)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(e,z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate (NP0317201)

MOL for NP0317201 ((3r,4e,8z)-1-[(3e,4s,5r)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(e,z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate)

3D MOL for NP0317201 ((3r,4e,8z)-1-[(3e,4s,5r)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(e,z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate)

3D SDF for NP0317201 ((3r,4e,8z)-1-[(3e,4s,5r)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(e,z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate)

3D-SDF for NP0317201 ((3r,4e,8z)-1-[(3e,4s,5r)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(e,z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate)

PDB for NP0317201 ((3r,4e,8z)-1-[(3e,4s,5r)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(e,z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate)

3D PDB for NP0317201 ((3r,4e,8z)-1-[(3e,4s,5r)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(e,z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate)

SMILES for NP0317201 ((3r,4e,8z)-1-[(3e,4s,5r)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(e,z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate)

INCHI for NP0317201 ((3r,4e,8z)-1-[(3e,4s,5r)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(e,z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate)

Structure for NP0317201 ((3r,4e,8z)-1-[(3e,4s,5r)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(e,z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate)

3D Structure for NP0317201 ((3r,4e,8z)-1-[(3e,4s,5r)-4-(acetyloxy)-5-(2-methylprop-1-en-1-yl)-2-oxooxolan-3-ylidene]-10-[(e,z)-benzoyloxy]-4,8-dimethyldeca-4,8-dien-3-yl acetate)