NP-MRD: Showing NP-Card for (1s,4s,6r,7s)-7-[(1e)-2-[(1r,6s,7s,8s)-8-[(1r,2e)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione (NP0149709)

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Record Information

Version

2.0

Created at

2022-09-02 05:38:17 UTC

Updated at

2022-09-02 05:38:18 UTC

NP-MRD ID

NP0149709

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,4s,6r,7s)-7-[(1e)-2-[(1r,6s,7s,8s)-8-[(1r,2e)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione

Description

Shimalactone B belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units. (1s,4s,6r,7s)-7-[(1e)-2-[(1r,6s,7s,8s)-8-[(1r,2e)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione is found in Aspergillus stellatus. (1s,4s,6r,7s)-7-[(1e)-2-[(1r,6s,7s,8s)-8-[(1r,2e)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione was first documented in 2020 (PMID: 32129542). Based on a literature review very few articles have been published on Shimalactone B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022207382D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309022207382D          

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 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  2  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
 16 17  1  1  0  0  0
 16 18  1  0  0  0  0
  7 18  1  0  0  0  0
 18 19  1  6  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  1  0  0  0
 22 24  1  0  0  0  0
 24 25  1  1  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 22 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 24 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0149709

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C=C(/C)[C@@H](O)[C@]1(C)[C@@H](\C(C)=C\[C@]2(C)[C@H]3OC(=O)[C@]2(C)C(=O)[C@@H]3C)[C@@]2(C)C=C(C)C=C(C)[C@@H]12

> <INCHI_IDENTIFIER>
InChI=1S/C29H40O4/c1-11-16(3)22(30)28(9)20-17(4)12-15(2)13-26(20,7)21(28)18(5)14-27(8)24-19(6)23(31)29(27,10)25(32)33-24/h11-14,19-22,24,30H,1-10H3/b16-11+,18-14+/t19-,20+,21-,22+,24-,26-,27+,28-,29-/m0/s1

> <INCHI_KEY>
BNFUGVFXZSYVMT-SXXAEEKTSA-N

> <FORMULA>
C29H40O4

> <MOLECULAR_WEIGHT>
452.635

> <EXACT_MASS>
452.292659768

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
51.26908343323345

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,4S,6R,7S)-7-[(1E)-2-[(1R,6S,7S,8S)-8-[(1R,2E)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione

> <ALOGPS_LOGP>
6.29

> <JCHEM_LOGP>
5.326630449333335

> <ALOGPS_LOGS>
-5.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.73437980274227

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5105369222193109

> <JCHEM_POLAR_SURFACE_AREA>
63.6

> <JCHEM_REFRACTIVITY>
133.81169999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.06e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1S,4S,6R,7S)-7-[(1E)-2-[(1R,6S,7S,8S)-8-[(1R,2E)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0      -0.638  -6.582   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.593  -5.043   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.762  -4.312   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.073  -5.121   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.808  -2.773   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -0.503  -1.964   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       2.163  -2.042   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.894  -3.398   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.433  -0.687   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.122   0.122   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.234  -0.609   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.167   1.661   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.523   2.392   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.568   3.931   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.833   1.583   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.788   0.044   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.287   0.399   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.519  -1.312   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       4.994  -1.754   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.114  -0.697   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.349  -3.252   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.824  -3.694   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       5.349  -4.136   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.209  -2.154   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       5.875  -2.924   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       5.875  -4.464   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       4.542  -5.234   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       7.209  -5.234   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       7.209  -6.774   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       8.543  -4.464   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       9.877  -5.234   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       8.543  -2.924   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.877  -2.154   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5    8    9   18                                             
CONECT    8    7                                                            
CONECT    9    7   10   16                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13   16                                                       
CONECT   16   15    9   17   18                                             
CONECT   17   16                                                            
CONECT   18   16    7   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20   19                                                            
CONECT   21   19   22                                                       
CONECT   22   21   23   24   28                                             
CONECT   23   22                                                            
CONECT   24   22   25   32                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   22   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   24   33                                                  
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₉H₄₀O₄

Average Mass

452.6350 Da

Monoisotopic Mass

452.29266 Da

IUPAC Name

(1S,4S,6R,7S)-7-[(1E)-2-[(1R,6S,7S,8S)-8-[(1R,2E)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

C\C=C(/C)[C@@H](O)[C@]1(C)[C@@H](\C(C)=C\[C@]2(C)[C@H]3OC(=O)[C@]2(C)C(=O)[C@@H]3C)[C@@]2(C)C=C(C)C=C(C)[C@@H]12

InChI Identifier

InChI=1S/C29H40O4/c1-11-16(3)22(30)28(9)20-17(4)12-15(2)13-26(20,7)21(28)18(5)14-27(8)24-19(6)23(31)29(27,10)25(32)33-24/h11-14,19-22,24,30H,1-10H3/b16-11+,18-14+/t19-,20+,21-,22+,24-,26-,27+,28-,29-/m0/s1

InChI Key

BNFUGVFXZSYVMT-SXXAEEKTSA-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
Aspergillus stellatus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesterterpenoids. These are terpenes composed of five consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesterterpenoids

Direct Parent

Sesterterpenoids

Alternative Parents

Substituents

Sesterterpenoid
Delta valerolactone
Delta_valerolactone
Gamma butyrolactone
Oxane
Oxolane
Carboxylic acid ester
Ketone
Lactone
Secondary alcohol
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Carbonyl group
Hydrocarbon derivative
Alcohol
Organic oxide
Organooxygen compound
Organic oxygen 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	6.29	ALOGPS
logP	5.33	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	16.73	ChemAxon
pKa (Strongest Basic)	-0.51	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	133.81 m³·mol⁻¹	ChemAxon
Polarizability	51.27 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	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

9822866

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15976830

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fujii I, Hashimoto M, Konishi K, Unezawa A, Sakuraba H, Suzuki K, Tsushima H, Iwasaki M, Yoshida S, Kudo A, Fujita R, Hichiwa A, Saito K, Asano T, Ishikawa J, Wakana D, Goda Y, Watanabe A, Watanabe M, Masumoto Y, Kanazawa J, Sato H, Uchiyama M: Shimalactone Biosynthesis Involves Spontaneous Double Bicyclo-Ring Formation with 8pi-6pi Electrocyclization. Angew Chem Int Ed Engl. 2020 May 25;59(22):8464-8470. doi: 10.1002/anie.202001024. Epub 2020 Mar 20. [PubMed:32129542 ]
LOTUS database [Link]

Showing NP-Card for (1s,4s,6r,7s)-7-[(1e)-2-[(1r,6s,7s,8s)-8-[(1r,2e)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione (NP0149709)

MOL for NP0149709 ((1s,4s,6r,7s)-7-[(1e)-2-[(1r,6s,7s,8s)-8-[(1r,2e)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione)

3D MOL for NP0149709 ((1s,4s,6r,7s)-7-[(1e)-2-[(1r,6s,7s,8s)-8-[(1r,2e)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione)

3D SDF for NP0149709 ((1s,4s,6r,7s)-7-[(1e)-2-[(1r,6s,7s,8s)-8-[(1r,2e)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione)

3D-SDF for NP0149709 ((1s,4s,6r,7s)-7-[(1e)-2-[(1r,6s,7s,8s)-8-[(1r,2e)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione)

PDB for NP0149709 ((1s,4s,6r,7s)-7-[(1e)-2-[(1r,6s,7s,8s)-8-[(1r,2e)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione)

3D PDB for NP0149709 ((1s,4s,6r,7s)-7-[(1e)-2-[(1r,6s,7s,8s)-8-[(1r,2e)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione)

SMILES for NP0149709 ((1s,4s,6r,7s)-7-[(1e)-2-[(1r,6s,7s,8s)-8-[(1r,2e)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione)

INCHI for NP0149709 ((1s,4s,6r,7s)-7-[(1e)-2-[(1r,6s,7s,8s)-8-[(1r,2e)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione)

Structure for NP0149709 ((1s,4s,6r,7s)-7-[(1e)-2-[(1r,6s,7s,8s)-8-[(1r,2e)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione)

3D Structure for NP0149709 ((1s,4s,6r,7s)-7-[(1e)-2-[(1r,6s,7s,8s)-8-[(1r,2e)-1-hydroxy-2-methylbut-2-en-1-yl]-2,4,6,8-tetramethylbicyclo[4.2.0]octa-2,4-dien-7-yl]prop-1-en-1-yl]-4,6,7-trimethyl-2-oxabicyclo[2.2.1]heptane-3,5-dione)