NP-MRD: Showing NP-Card for (1r,2s,3s,4as,6r,8r,8ar)-2,6-bis(acetyloxy)-8-[(1e)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-hexahydro-1h-naphthalen-1-yl benzoate (NP0317685)

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Record Information

Version

2.0

Created at

2022-09-11 17:42:22 UTC

Updated at

2022-09-11 17:42:22 UTC

NP-MRD ID

NP0317685

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3s,4as,6r,8r,8ar)-2,6-bis(acetyloxy)-8-[(1e)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-hexahydro-1h-naphthalen-1-yl benzoate

Description

(1R,2S,3S,4aS,6R,8R,8aR)-2,6-bis(acetyloxy)-8-[(1E)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-decahydronaphthalen-1-yl benzoate belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other. Based on a literature review very few articles have been published on (1R,2S,3S,4aS,6R,8R,8aR)-2,6-bis(acetyloxy)-8-[(1E)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-decahydronaphthalen-1-yl benzoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112219422D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309112219422D          

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    2.8579   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434   -2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -4.1250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -4.1250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  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
  6  8  1  0  0  0  0
  8  9  1  6  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  8 13  1  0  0  0  0
 14 13  1  1  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 18  1  0  0  0  0
 18 19  1  6  0  0  0
 18 20  1  0  0  0  0
 20 21  1  6  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 20 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  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
 29 34  1  0  0  0  0
 25 35  1  0  0  0  0
 14 35  1  0  0  0  0
  5 35  1  0  0  0  0
 35 36  1  6  0  0  0
  3 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0317685

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@H]2C(C)(C)[C@H](O)[C@H](OC(C)=O)[C@H](OC(=O)C3=CC=CC=C3)[C@@]2(C)[C@@H](\C=C(/C=C)C(C)=O)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O9/c1-8-19(16(2)31)14-21-24(34)22(37-17(3)32)15-23-29(5,6)26(35)25(38-18(4)33)27(30(21,23)7)39-28(36)20-12-10-9-11-13-20/h8-14,21-23,25-27,35H,1,15H2,2-7H3/b19-14+/t21-,22+,23-,25-,26+,27-,30-/m0/s1

> <INCHI_KEY>
PHXNLVUWPCOMGG-XZHACOCXSA-N

> <FORMULA>
C30H36O9

> <MOLECULAR_WEIGHT>
540.609

> <EXACT_MASS>
540.235932739

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
75

> <JCHEM_AVERAGE_POLARIZABILITY>
55.97159270830221

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3S,4aS,6R,8R,8aR)-2,6-bis(acetyloxy)-8-[(1E)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-decahydronaphthalen-1-yl benzoate

> <JCHEM_LOGP>
3.6319931723333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.663846228470813

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.535061108223996

> <JCHEM_PKA_STRONGEST_BASIC>
-3.3878554398197407

> <JCHEM_POLAR_SURFACE_AREA>
133.27

> <JCHEM_REFRACTIVITY>
141.03340000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,4aS,6R,8R,8aR)-2,6-bis(acetyloxy)-8-[(1E)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-hexahydro-1H-naphthalen-1-yl benzoate

> <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      -1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000  -4.620   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.000  -3.080   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       1.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       8.002  -3.080   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      10.669  -3.080   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.335  -4.620   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.668  -5.390   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0       8.002  -4.620   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       6.668  -6.930   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.002  -7.700   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.668 -10.010   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       5.335  -7.700   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       1.334  -6.930   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       0.000  -7.700   0.000  0.00  0.00           C+0
HETATM   39  O   UNK     0       2.667  -7.700   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   37                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   35                                                  
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   35                                                  
CONECT   15   14   16   17   18                                             
CONECT   16   15                                                            
CONECT   17   15                                                            
CONECT   18   15   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22                                                            
CONECT   25   20   26   35                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29                                                       
CONECT   35   25   14    5   36                                             
CONECT   36   35                                                            
CONECT   37    3   38   39                                                  
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   82    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,3S,4AS,6R,8R,8ar)-2,6-bis(acetyloxy)-8-[(1E)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-decahydronaphthalen-1-yl benzoic acid	Generator

Chemical Formula

C₃₀H₃₆O₉

Average Mass

540.6090 Da

Monoisotopic Mass

540.23593 Da

IUPAC Name

(1R,2S,3S,4aS,6R,8R,8aR)-2,6-bis(acetyloxy)-8-[(1E)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-decahydronaphthalen-1-yl benzoate

Traditional Name

(1R,2S,3S,4aS,6R,8R,8aR)-2,6-bis(acetyloxy)-8-[(1E)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-hexahydro-1H-naphthalen-1-yl benzoate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@H]2C(C)(C)[C@H](O)[C@H](OC(C)=O)[C@H](OC(=O)C3=CC=CC=C3)[C@@]2(C)[C@@H](\C=C(/C=C)C(C)=O)C1=O

InChI Identifier

InChI=1S/C30H36O9/c1-8-19(16(2)31)14-21-24(34)22(37-17(3)32)15-23-29(5,6)26(35)25(38-18(4)33)27(30(21,23)7)39-28(36)20-12-10-9-11-13-20/h8-14,21-23,25-27,35H,1,15H2,2-7H3/b19-14+/t21-,22+,23-,25-,26+,27-,30-/m0/s1

InChI Key

PHXNLVUWPCOMGG-XZHACOCXSA-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 bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Bicyclic monoterpenoids

Alternative Parents

Substituents

Bicyclic monoterpenoid
Benzoate ester
Aromatic monoterpenoid
Tricarboxylic acid or derivatives
Benzoic acid or derivatives
Benzoyl
Alpha-acyloxy ketone
Alpha-branched alpha,beta-unsaturated-ketone
Benzenoid
Monocyclic benzene moiety
Cyclitol or derivatives
Alpha,beta-unsaturated ketone
Enone
Cyclic alcohol
Acryloyl-group
Cyclic ketone
Secondary alcohol
Ketone
Carboxylic acid ester
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	3.63	ChemAxon
pKa (Strongest Acidic)	11.54	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	133.27 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	141.03 m³·mol⁻¹	ChemAxon
Polarizability	55.97 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

162938691

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3s,4as,6r,8r,8ar)-2,6-bis(acetyloxy)-8-[(1e)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-hexahydro-1h-naphthalen-1-yl benzoate (NP0317685)

MOL for NP0317685 ((1r,2s,3s,4as,6r,8r,8ar)-2,6-bis(acetyloxy)-8-[(1e)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-hexahydro-1h-naphthalen-1-yl benzoate)

3D MOL for NP0317685 ((1r,2s,3s,4as,6r,8r,8ar)-2,6-bis(acetyloxy)-8-[(1e)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-hexahydro-1h-naphthalen-1-yl benzoate)

3D SDF for NP0317685 ((1r,2s,3s,4as,6r,8r,8ar)-2,6-bis(acetyloxy)-8-[(1e)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-hexahydro-1h-naphthalen-1-yl benzoate)

3D-SDF for NP0317685 ((1r,2s,3s,4as,6r,8r,8ar)-2,6-bis(acetyloxy)-8-[(1e)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-hexahydro-1h-naphthalen-1-yl benzoate)

PDB for NP0317685 ((1r,2s,3s,4as,6r,8r,8ar)-2,6-bis(acetyloxy)-8-[(1e)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-hexahydro-1h-naphthalen-1-yl benzoate)

3D PDB for NP0317685 ((1r,2s,3s,4as,6r,8r,8ar)-2,6-bis(acetyloxy)-8-[(1e)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-hexahydro-1h-naphthalen-1-yl benzoate)

SMILES for NP0317685 ((1r,2s,3s,4as,6r,8r,8ar)-2,6-bis(acetyloxy)-8-[(1e)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-hexahydro-1h-naphthalen-1-yl benzoate)

INCHI for NP0317685 ((1r,2s,3s,4as,6r,8r,8ar)-2,6-bis(acetyloxy)-8-[(1e)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-hexahydro-1h-naphthalen-1-yl benzoate)

Structure for NP0317685 ((1r,2s,3s,4as,6r,8r,8ar)-2,6-bis(acetyloxy)-8-[(1e)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-hexahydro-1h-naphthalen-1-yl benzoate)

3D Structure for NP0317685 ((1r,2s,3s,4as,6r,8r,8ar)-2,6-bis(acetyloxy)-8-[(1e)-2-ethenyl-3-oxobut-1-en-1-yl]-3-hydroxy-4,4,8a-trimethyl-7-oxo-hexahydro-1h-naphthalen-1-yl benzoate)