NP-MRD: Showing NP-Card for 6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate (NP0190381)

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Record Information

Version

2.0

Created at

2022-09-04 07:02:34 UTC

Updated at

2022-09-04 07:02:34 UTC

NP-MRD ID

NP0190381

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate

Description

6-{[5-(3-Hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units. 6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate is found in Aster oharai. 6-{[5-(3-Hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171503152D          

 36 38  0  0  0  0            999 V2000
    3.5724   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
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 34 36  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004171503152D          

 36 38  0  0  0  0            999 V2000
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    1.3184   -3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9059   -2.9980    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -4.5375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -6.1875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -7.0125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158   -7.4250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -7.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 16 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 10 22  1  0  0  0  0
 15 22  1  0  0  0  0
 22 23  1  0  0  0  0
 13 24  1  0  0  0  0
 24 25  1  0  0  0  0
  6 26  1  0  0  0  0
 26 27  2  0  0  0  0
  4 28  1  0  0  0  0
 28 29  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 30 32  1  0  0  0  0
  2 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0190381

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1OC(OC(C)(CCC2=C(C)C(CC3C(C)(C)CCCC23C)OO)C=C)C(O)C(O)C1OC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C28H46O8/c1-9-27(7,35-25-23(31)22(30)24(17(3)33-25)34-18(4)29)14-11-19-16(2)20(36-32)15-21-26(5,6)12-10-13-28(19,21)8/h9,17,20-25,30-32H,1,10-15H2,2-8H3

> <INCHI_KEY>
CYFQGASFWKNUEE-UHFFFAOYSA-N

> <FORMULA>
C28H46O8

> <MOLECULAR_WEIGHT>
510.668

> <EXACT_MASS>
510.319268441

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
56.94671097723131

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate

> <ALOGPS_LOGP>
3.90

> <JCHEM_LOGP>
4.1385521496666655

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.374121655611795

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.605624234253746

> <JCHEM_PKA_STRONGEST_BASIC>
-3.691297537891672

> <JCHEM_POLAR_SURFACE_AREA>
114.68

> <JCHEM_REFRACTIVITY>
134.771

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.28e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       6.668 -13.090   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668 -11.550   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       5.335 -10.780   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       5.335  -9.240   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       4.001  -8.470   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       4.001  -6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.541  -6.930   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   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  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   0.000   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  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.345   1.180   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.325   1.180   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.335  -3.080   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       4.001  -3.850   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       0.000   0.000   0.000  0.00  0.00           O+0
HETATM   25  O   UNK     0       0.000   1.540   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       2.461  -6.930   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.691  -5.596   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.668  -8.470   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.668  -6.930   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       8.002  -9.240   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.336  -8.470   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.002 -10.780   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       9.336 -11.550   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       9.336 -13.090   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      10.669 -13.860   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       8.002 -13.860   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   32                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   28                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8   26                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   22                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   24                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16   22                                                  
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   10   15   23                                             
CONECT   23   22                                                            
CONECT   24   13   25                                                       
CONECT   25   24                                                            
CONECT   26    6   27                                                       
CONECT   27   26                                                            
CONECT   28    4   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30    2   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   76    0
END

View in JSmol

Synonyms

Value	Source
6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetic acid	Generator

Chemical Formula

C₂₈H₄₆O₈

Average Mass

510.6680 Da

Monoisotopic Mass

510.31927 Da

IUPAC Name

6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,5,6,7,8,8a-octahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate

Traditional Name

6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate

CAS Registry Number

Not Available

SMILES

CC1OC(OC(C)(CCC2=C(C)C(CC3C(C)(C)CCCC23C)OO)C=C)C(O)C(O)C1OC(C)=O

InChI Identifier

InChI=1S/C28H46O8/c1-9-27(7,35-25-23(31)22(30)24(17(3)33-25)34-18(4)29)14-11-19-16(2)20(36-32)15-21-26(5,6)12-10-13-28(19,21)8/h9,17,20-25,30-32H,1,10-15H2,2-8H3

InChI Key

CYFQGASFWKNUEE-UHFFFAOYSA-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
Aster oharai	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as diterpenoids. These are terpene compounds formed by four isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Diterpenoids

Alternative Parents

Substituents

Labdane diterpenoid
Diterpenoid
Fatty acyl glycoside
Fatty acyl glycoside of mono- or disaccharide
Alkyl glycoside
Hexose monosaccharide
Glycosyl compound
O-glycosyl compound
Fatty acyl
Monosaccharide
Oxane
1,2-diol
Carboxylic acid ester
Secondary alcohol
Hydroperoxide
Organoheterocyclic compound
Oxacycle
Alkyl hydroperoxide
Acetal
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Peroxol
Alcohol
Hydrocarbon derivative
Organic oxide
Carbonyl group
Organic oxygen compound
Organooxygen compound
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	3.9	ALOGPS
logP	4.14	ChemAxon
logS	-4.6	ALOGPS
pKa (Strongest Acidic)	11.61	ChemAxon
pKa (Strongest Basic)	-3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	114.68 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	134.77 m³·mol⁻¹	ChemAxon
Polarizability	56.95 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

73880600

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate (NP0190381)

MOL for NP0190381 (6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate)

3D MOL for NP0190381 (6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate)

3D SDF for NP0190381 (6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate)

3D-SDF for NP0190381 (6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate)

PDB for NP0190381 (6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate)

3D PDB for NP0190381 (6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate)

SMILES for NP0190381 (6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate)

INCHI for NP0190381 (6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate)

Structure for NP0190381 (6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate)

3D Structure for NP0190381 (6-{[5-(3-hydroperoxy-2,5,5,8a-tetramethyl-3,4,4a,6,7,8-hexahydronaphthalen-1-yl)-3-methylpent-1-en-3-yl]oxy}-4,5-dihydroxy-2-methyloxan-3-yl acetate)