NP-MRD: Showing NP-Card for 6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione (NP0326594)

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Record Information

Version

2.0

Created at

2022-09-12 08:17:38 UTC

Updated at

2022-09-12 08:17:39 UTC

NP-MRD ID

NP0326594

Secondary Accession Numbers

None

Natural Product Identification

Common Name

6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione

Description

6-(Furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]Octadeca-12,16-diene-14,18-dione belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17. 6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione is found in Toona ciliata and Trichilia catigua. 6-(Furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]Octadeca-12,16-diene-14,18-dione is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241521152D          

 31 36  0  0  0  0            999 V2000
    4.2063   -1.1380    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4904   -0.3634    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0222    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.7419    1.0432    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9298    1.1884    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3979    0.5577    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6782   -0.2182    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1464   -0.8489    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3343   -0.7037    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8025   -1.3344    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0540    0.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5858    0.7029    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3055    1.4789    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4934    1.6241    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9616    0.9934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2419    0.2174    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5906   -0.2889    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3547   -0.5998    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0923    0.1741    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1370    0.9666    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3693    1.6179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1939    1.5911    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4742    2.3670    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8229    2.8734    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1400    2.4104    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6017    1.7357    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7431   -0.6920    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4267   -1.6248    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.1176    1.3336    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2038   -0.7776    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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  3  4  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
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  7 13  1  0  0  0  0
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  7 30  1  0  0  0  0
  2 31  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004241521152D          

 31 36  0  0  0  0            999 V2000
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    5.0222    0.2673    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8343    0.1221    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0326594

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC12CCC3C4(C)C=CC(=O)C(C)(C)C4=C(O)C(=O)C3(C)C11OC1CC2C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C26H30O5/c1-22(2)17(27)7-9-23(3)16-6-10-24(4)15(14-8-11-30-13-14)12-18-26(24,31-18)25(16,5)21(29)19(28)20(22)23/h7-9,11,13,15-16,18,28H,6,10,12H2,1-5H3

> <INCHI_KEY>
OQMUOVSEPOBWMK-UHFFFAOYSA-N

> <FORMULA>
C26H30O5

> <MOLECULAR_WEIGHT>
422.521

> <EXACT_MASS>
422.209324066

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
61

> <JCHEM_AVERAGE_POLARIZABILITY>
45.15931833129521

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione

> <ALOGPS_LOGP>
4.39

> <JCHEM_LOGP>
4.451640761666667

> <ALOGPS_LOGS>
-4.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
8.433175659991663

> <JCHEM_PKA_STRONGEST_BASIC>
-2.786111960642718

> <JCHEM_POLAR_SURFACE_AREA>
80.04

> <JCHEM_REFRACTIVITY>
116.60129999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.31e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0       7.852  -2.124   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.382  -0.678   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.375   0.499   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.891   0.228   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       8.852   1.947   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.336   2.218   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.343   1.041   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.866  -0.407   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       5.873  -1.585   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.357  -1.314   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       3.365  -2.491   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       3.834   0.135   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.827   1.312   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.304   2.761   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.788   3.032   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.795   1.854   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.318   0.406   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       1.102  -0.539   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       2.529  -1.120   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      -0.172   0.325   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       0.256   1.804   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      -0.689   3.020   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      -2.229   2.970   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      -2.752   4.418   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      -1.536   5.364   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      -0.261   4.499   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       1.123   3.240   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.254  -1.292   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       6.397  -3.033   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.820   2.489   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.714  -1.452   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    8   31                                             
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8   13   30                                             
CONECT    8    7    2    9                                                  
CONECT    9    8   10   29                                                  
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10   13   17   28                                             
CONECT   13   12    7   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   21   27                                             
CONECT   17   16   12   18   19                                             
CONECT   18   17   19   20                                                  
CONECT   19   18   17                                                       
CONECT   20   18   21                                                       
CONECT   21   20   16   22                                                  
CONECT   22   21   23   26                                                  
CONECT   23   22   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   22                                                       
CONECT   27   16                                                            
CONECT   28   12                                                            
CONECT   29    9                                                            
CONECT   30    7                                                            
CONECT   31    2                                                            
MASTER        0    0    0    0    0    0    0    0   31    0   72    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₀O₅

Average Mass

422.5210 Da

Monoisotopic Mass

422.20932 Da

IUPAC Name

6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione

Traditional Name

6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione

CAS Registry Number

Not Available

SMILES

CC12CCC3C4(C)C=CC(=O)C(C)(C)C4=C(O)C(=O)C3(C)C11OC1CC2C1=COC=C1

InChI Identifier

InChI=1S/C26H30O5/c1-22(2)17(27)7-9-23(3)16-6-10-24(4)15(14-8-11-30-13-14)12-18-26(24,31-18)25(16,5)21(29)19(28)20(22)23/h7-9,11,13,15-16,18,28H,6,10,12H2,1-5H3

InChI Key

OQMUOVSEPOBWMK-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
Toona ciliata	LOTUS Database	35616633
Trichilia catigua	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as limonoids. These are highly oxygenated, modified terpenoids with a prototypical structure either containing or derived from a precursor with a 4,4,8-trimethyl-17-furanylsteroid skeleton. All naturally occurring citrus limonoids contain a furan ring attached to the D-ring, at C-17, as well as oxygen containing functional groups at C-3, C-4, C-7, C-16 and C-17.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Limonoids

Alternative Parents

Substituents

Limonoid skeleton
17-furanylsteroid skeleton
3-oxo-delta-1-steroid
7-oxosteroid
Oxosteroid
Delta-1-steroid
Steroid
Naphthopyran
Naphthalene
Cyclohexenone
Pyran
Oxane
Heteroaromatic compound
Furan
Ketone
Cyclic ketone
Dialkyl ether
Enol
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Organic oxide
Carbonyl group
Hydrocarbon derivative
Organic oxygen compound
Organooxygen 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	4.39	ALOGPS
logP	4.45	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	8.43	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	80.04 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	116.6 m³·mol⁻¹	ChemAxon
Polarizability	45.16 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	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

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

5136005

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione (NP0326594)

MOL for NP0326594 (6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione)

3D MOL for NP0326594 (6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione)

3D SDF for NP0326594 (6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione)

3D-SDF for NP0326594 (6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione)

PDB for NP0326594 (6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione)

3D PDB for NP0326594 (6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione)

SMILES for NP0326594 (6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione)

INCHI for NP0326594 (6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione)

Structure for NP0326594 (6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione)

3D Structure for NP0326594 (6-(furan-3-yl)-17-hydroxy-1,7,11,15,15-pentamethyl-3-oxapentacyclo[8.8.0.0²,⁴.0²,⁷.0¹¹,¹⁶]octadeca-12,16-diene-14,18-dione)