NP-MRD: Showing NP-Card for (1r,2s,4s)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6ar,10ar)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6ah,7h,8h,10ah-benzo[c]isochromene-2-carboxylate (NP0211135)

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Record Information

Version

2.0

Created at

2022-09-05 09:16:02 UTC

Updated at

2022-09-05 09:16:02 UTC

NP-MRD ID

NP0211135

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,4s)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6ar,10ar)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6ah,7h,8h,10ah-benzo[c]isochromene-2-carboxylate

Description

(1R,2S,4S)-1,3,3-trimethylbicyclo[2.2.1]Heptan-2-yl (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylate belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position. (1r,2s,4s)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6ar,10ar)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6ah,7h,8h,10ah-benzo[c]isochromene-2-carboxylate is found in Cannabis sativa. Based on a literature review very few articles have been published on (1R,2S,4S)-1,3,3-trimethylbicyclo[2.2.1]Heptan-2-yl (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052211162D          

 36 40  0  0  1  0            999 V2000
    7.3145    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END

     RDKit          3D

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M  END


  Mrv1652309052211162D          

 36 40  0  0  1  0            999 V2000
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    2.7770   -3.1599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -2.9536    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5395    0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.1270   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020   -0.3020    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105   -1.0164    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1105    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3020    1.1270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1270    1.1270    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5395    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7642    2.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6827    2.6539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.8414    0.0000 O   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  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  2  0  0  0  0
  6 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 13 15  1  0  0  0  0
 16 15  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 17 19  1  0  0  0  0
 17 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 20 25  1  6  0  0  0
 26  9  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  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
 32 31  1  1  0  0  0
 26 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 33 36  1  0  0  0  0
  8 36  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0211135

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCCCC1=CC2=C([C@@H]3C=C(C)CC[C@H]3C(C)(C)O2)C(O)=C1C(=O)O[C@H]1[C@]2(C)CC[C@@H](C2)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C32H46O4/c1-8-9-10-11-20-17-24-26(22-16-19(2)12-13-23(22)31(5,6)36-24)27(33)25(20)28(34)35-29-30(3,4)21-14-15-32(29,7)18-21/h16-17,21-23,29,33H,8-15,18H2,1-7H3/t21-,22+,23+,29+,32+/m0/s1

> <INCHI_KEY>
MQJYRDGWGIZCIV-IZFUNMHRSA-N

> <FORMULA>
C32H46O4

> <MOLECULAR_WEIGHT>
494.716

> <EXACT_MASS>
494.339609961

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
82

> <JCHEM_AVERAGE_POLARIZABILITY>
59.59261474526677

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylate

> <JCHEM_LOGP>
9.261576484333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.512481534959392

> <JCHEM_PKA_STRONGEST_BASIC>
-4.115143171528175

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
145.6578

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      13.654   3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      12.114   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.344   2.104   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.804   2.104   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       9.034   0.770   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.494   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.724   2.104   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.184   2.104   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.414   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.184  -0.564   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       4.414  -1.897   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       6.724  -0.564   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.494  -1.897   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       9.034  -1.897   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       6.724  -3.231   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.494  -4.565   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.034  -4.565   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.766  -3.048   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.481  -4.038   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       9.804  -5.898   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.034  -7.232   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.494  -7.232   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       6.724  -5.898   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       5.184  -5.898   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.264  -5.513   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       2.874   0.770   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       2.104  -0.564   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       0.564  -0.564   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      -0.206  -1.897   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.206   0.770   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.564   2.104   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.104   2.104   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.874   3.437   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       1.427   3.964   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.141   4.954   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       4.414   3.437   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9   36                                                  
CONECT    9    8   10   26                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10    6   13                                                  
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17   23                                                  
CONECT   17   16   18   19   20                                             
CONECT   18   17                                                            
CONECT   19   17                                                            
CONECT   20   17   21   25                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   16   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   20                                                       
CONECT   26    9   27   32                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   26   33                                                  
CONECT   33   32   34   35   36                                             
CONECT   34   33                                                            
CONECT   35   33                                                            
CONECT   36   33    8                                                       
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
(1R,2S,4S)-1,3,3-Trimethylbicyclo[2.2.1]heptan-2-yl (6ar,10ar)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,6ah,7H,8H,10ah-benzo[c]isochromene-2-carboxylic acid	Generator

Chemical Formula

C₃₂H₄₆O₄

Average Mass

494.7160 Da

Monoisotopic Mass

494.33961 Da

IUPAC Name

(1R,2S,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6H,6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylate

Traditional Name

(1R,2S,4S)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6aR,10aR)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6aH,7H,8H,10aH-benzo[c]isochromene-2-carboxylate

CAS Registry Number

Not Available

SMILES

CCCCCC1=CC2=C([C@@H]3C=C(C)CC[C@H]3C(C)(C)O2)C(O)=C1C(=O)O[C@H]1[C@]2(C)CC[C@@H](C2)C1(C)C

InChI Identifier

InChI=1S/C32H46O4/c1-8-9-10-11-20-17-24-26(22-16-19(2)12-13-23(22)31(5,6)36-24)27(33)25(20)28(34)35-29-30(3,4)21-14-15-32(29,7)18-21/h16-17,21-23,29,33H,8-15,18H2,1-7H3/t21-,22+,23+,29+,32+/m0/s1

InChI Key

MQJYRDGWGIZCIV-IZFUNMHRSA-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
Cannabis sativa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 2,2-dimethyl-1-benzopyrans. These are organic compounds containing a 1-benzopyran moiety that carries two methyl groups at the 2-position.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Benzopyrans

Sub Class

1-benzopyrans

Direct Parent

2,2-dimethyl-1-benzopyrans

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
Aromatic monoterpenoid
Fenchane monoterpenoid
Monoterpenoid
Salicylic acid or derivatives
Norbornane monoterpenoid
1-hydroxy-4-unsubstituted benzenoid
Alkyl aryl ether
Benzenoid
Vinylogous acid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Ether
Oxacycle
Carboxylic acid derivative
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic 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	9.26	ChemAxon
pKa (Strongest Acidic)	9.51	ChemAxon
pKa (Strongest Basic)	-4.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	55.76 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	145.66 m³·mol⁻¹	ChemAxon
Polarizability	59.59 Å³	ChemAxon
Number of Rings	5	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

58828763

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

162906422

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,4s)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6ar,10ar)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6ah,7h,8h,10ah-benzo[c]isochromene-2-carboxylate (NP0211135)

MOL for NP0211135 ((1r,2s,4s)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6ar,10ar)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6ah,7h,8h,10ah-benzo[c]isochromene-2-carboxylate)

3D MOL for NP0211135 ((1r,2s,4s)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6ar,10ar)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6ah,7h,8h,10ah-benzo[c]isochromene-2-carboxylate)

3D SDF for NP0211135 ((1r,2s,4s)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6ar,10ar)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6ah,7h,8h,10ah-benzo[c]isochromene-2-carboxylate)

3D-SDF for NP0211135 ((1r,2s,4s)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6ar,10ar)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6ah,7h,8h,10ah-benzo[c]isochromene-2-carboxylate)

PDB for NP0211135 ((1r,2s,4s)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6ar,10ar)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6ah,7h,8h,10ah-benzo[c]isochromene-2-carboxylate)

3D PDB for NP0211135 ((1r,2s,4s)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6ar,10ar)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6ah,7h,8h,10ah-benzo[c]isochromene-2-carboxylate)

SMILES for NP0211135 ((1r,2s,4s)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6ar,10ar)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6ah,7h,8h,10ah-benzo[c]isochromene-2-carboxylate)

INCHI for NP0211135 ((1r,2s,4s)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6ar,10ar)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6ah,7h,8h,10ah-benzo[c]isochromene-2-carboxylate)

Structure for NP0211135 ((1r,2s,4s)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6ar,10ar)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6ah,7h,8h,10ah-benzo[c]isochromene-2-carboxylate)

3D Structure for NP0211135 ((1r,2s,4s)-1,3,3-trimethylbicyclo[2.2.1]heptan-2-yl (6ar,10ar)-1-hydroxy-6,6,9-trimethyl-3-pentyl-6ah,7h,8h,10ah-benzo[c]isochromene-2-carboxylate)