NP-MRD: Showing NP-Card for [(1s,2r,4as,8ar)-5-[(acetyloxy)methyl]-1-{2-[(3r,5r)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl acetate (NP0225654)

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Record Information

Version

2.0

Created at

2022-09-06 04:26:29 UTC

Updated at

2022-09-06 04:26:29 UTC

NP-MRD ID

NP0225654

Secondary Accession Numbers

None

Natural Product Identification

Common Name

[(1s,2r,4as,8ar)-5-[(acetyloxy)methyl]-1-{2-[(3r,5r)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl acetate

Description

[(1S,2R,4aS,8aR)-5-[(acetyloxy)methyl]-1-{2-[(3R,5R)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4a-yl]methyl acetate belongs to the class of organic compounds known as colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations. Based on a literature review very few articles have been published on [(1S,2R,4aS,8aR)-5-[(acetyloxy)methyl]-1-{2-[(3R,5R)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4a-yl]methyl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062206262D          

 31 33  0  0  1  0            999 V2000
    4.6011   -5.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -4.8314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.8021   -4.0084    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.1024   -3.5712    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3020   -2.7707    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7717   -2.1387    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9592   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8986   -2.2820    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1434    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 C   0  0  0  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    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.0000    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    2.8579   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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    4.4340   -3.4781    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  4  5  1  0  0  0  0
  5  6  1  1  0  0  0
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  8 10  1  0  0  0  0
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 13 14  1  0  0  0  0
 14 15  1  6  0  0  0
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 17 18  1  0  0  0  0
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  8 29  1  0  0  0  0
  5 30  1  0  0  0  0
 30 31  1  0  0  0  0
  3 31  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309062206262D          

 31 33  0  0  1  0            999 V2000
    4.6011   -5.1930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8596   -4.8314    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0225654

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@H]1C[C@@H](CC[C@@]2(C)[C@H](C)CC[C@]3(COC(C)=O)[C@@H]2CCC=C3COC(C)=O)CO1

> <INCHI_IDENTIFIER>
InChI=1S/C25H40O6/c1-17-9-12-25(16-31-19(3)27)21(15-29-18(2)26)7-6-8-22(25)24(17,4)11-10-20-13-23(28-5)30-14-20/h7,17,20,22-23H,6,8-16H2,1-5H3/t17-,20-,22-,23-,24+,25-/m1/s1

> <INCHI_KEY>
PUPLZFXCMMDGOD-WUNGIAJVSA-N

> <FORMULA>
C25H40O6

> <MOLECULAR_WEIGHT>
436.589

> <EXACT_MASS>
436.282489008

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
50.038806238470684

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
[(1S,2R,4aS,8aR)-5-[(acetyloxy)methyl]-1-{2-[(3R,5R)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4a-yl]methyl acetate

> <JCHEM_LOGP>
3.524937086333331

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.0049482721075

> <JCHEM_POLAR_SURFACE_AREA>
71.06

> <JCHEM_REFRACTIVITY>
118.51579999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
10

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
[(1S,2R,4aS,8aR)-5-[(acetyloxy)methyl]-1-{2-[(3R,5R)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl acetate

> <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       8.589  -9.694   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       7.205  -9.019   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       7.097  -7.482   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.791  -6.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.164  -5.172   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.174  -3.992   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.657  -4.260   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.677  -4.260   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+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       4.001   0.770   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.667   1.540   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       2.667   3.080   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.001   3.850   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       1.334   3.850   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0       6.668   2.310   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.336   2.310   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       8.002  -0.000   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       7.700  -5.065   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       8.277  -6.492   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   31                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6   30                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   29                                             
CONECT    9    8                                                            
CONECT   10    8   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   20   29                                             
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   14   21   26                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23                                                            
CONECT   26   20   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   14    8                                                  
CONECT   30    5   31                                                       
CONECT   31   30    3                                                       
MASTER        0    0    0    0    0    0    0    0   31    0   66    0
END

View in JSmol

Synonyms

Value	Source
[(1S,2R,4AS,8ar)-5-[(acetyloxy)methyl]-1-{2-[(3R,5R)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4a-yl]methyl acetic acid	Generator

Chemical Formula

C₂₅H₄₀O₆

Average Mass

436.5890 Da

Monoisotopic Mass

436.28249 Da

IUPAC Name

[(1S,2R,4aS,8aR)-5-[(acetyloxy)methyl]-1-{2-[(3R,5R)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-1,2,3,4,4a,7,8,8a-octahydronaphthalen-4a-yl]methyl acetate

Traditional Name

[(1S,2R,4aS,8aR)-5-[(acetyloxy)methyl]-1-{2-[(3R,5R)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl acetate

CAS Registry Number

Not Available

SMILES

CO[C@H]1C[C@@H](CC[C@@]2(C)[C@H](C)CC[C@]3(COC(C)=O)[C@@H]2CCC=C3COC(C)=O)CO1

InChI Identifier

InChI=1S/C25H40O6/c1-17-9-12-25(16-31-19(3)27)21(15-29-18(2)26)7-6-8-22(25)24(17,4)11-10-20-13-23(28-5)30-14-20/h7,17,20,22-23H,6,8-16H2,1-5H3/t17-,20-,22-,23-,24+,25-/m1/s1

InChI Key

PUPLZFXCMMDGOD-WUNGIAJVSA-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 colensane and clerodane diterpenoids. These are diterpenoids with a structure based on the clerodane or the colensane skeleton. Clerodanes arise from labdanes by two methyl migrations.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Colensane and clerodane diterpenoids

Alternative Parents

Substituents

Clerodane diterpenoid
Dicarboxylic acid or derivatives
Tetrahydrofuran
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Acetal
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen 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	3.52	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	71.06 Å²	ChemAxon
Rotatable Bond Count	10	ChemAxon
Refractivity	118.52 m³·mol⁻¹	ChemAxon
Polarizability	50.04 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

163031143

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for [(1s,2r,4as,8ar)-5-[(acetyloxy)methyl]-1-{2-[(3r,5r)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl acetate (NP0225654)

MOL for NP0225654 ([(1s,2r,4as,8ar)-5-[(acetyloxy)methyl]-1-{2-[(3r,5r)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl acetate)

3D MOL for NP0225654 ([(1s,2r,4as,8ar)-5-[(acetyloxy)methyl]-1-{2-[(3r,5r)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl acetate)

3D SDF for NP0225654 ([(1s,2r,4as,8ar)-5-[(acetyloxy)methyl]-1-{2-[(3r,5r)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl acetate)

3D-SDF for NP0225654 ([(1s,2r,4as,8ar)-5-[(acetyloxy)methyl]-1-{2-[(3r,5r)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl acetate)

PDB for NP0225654 ([(1s,2r,4as,8ar)-5-[(acetyloxy)methyl]-1-{2-[(3r,5r)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl acetate)

3D PDB for NP0225654 ([(1s,2r,4as,8ar)-5-[(acetyloxy)methyl]-1-{2-[(3r,5r)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl acetate)

SMILES for NP0225654 ([(1s,2r,4as,8ar)-5-[(acetyloxy)methyl]-1-{2-[(3r,5r)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl acetate)

INCHI for NP0225654 ([(1s,2r,4as,8ar)-5-[(acetyloxy)methyl]-1-{2-[(3r,5r)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl acetate)

Structure for NP0225654 ([(1s,2r,4as,8ar)-5-[(acetyloxy)methyl]-1-{2-[(3r,5r)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl acetate)

3D Structure for NP0225654 ([(1s,2r,4as,8ar)-5-[(acetyloxy)methyl]-1-{2-[(3r,5r)-5-methoxyoxolan-3-yl]ethyl}-1,2-dimethyl-2,3,4,7,8,8a-hexahydronaphthalen-4a-yl]methyl acetate)