NP-MRD: Showing NP-Card for methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate (NP0202432)

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Record Information

Version

2.0

Created at

2022-09-04 21:38:58 UTC

Updated at

2022-09-04 21:38:58 UTC

NP-MRD ID

NP0202432

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate

Description

Methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]Henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate belongs to the class of organic compounds known as 3-hydroxysteroids. These are steroids carrying a hydroxyl group at the 3-position of the steroid backbone. methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate is found in Garcinia speciosa. Methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]Henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004231520242D          

 35 39  0  0  0  0            999 V2000
    9.9662    0.3316    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    6.3859    0.6680    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 33 34  1  0  0  0  0
 17 34  1  0  0  0  0
  5 35  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004231520242D          

 35 39  0  0  0  0            999 V2000
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   -0.9266    0.5837    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3783    1.1659    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3635    1.5270    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6051    1.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1989    1.0803    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6833    1.7481    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5038    1.6625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6130   -0.4351    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  2  0  0  0  0
  3  5  1  0  0  0  0
  5  6  2  0  0  0  0
  6  7  1  4  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  1  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
  7 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 11 21  1  0  0  0  0
 16 21  1  0  0  0  0
 21 22  1  0  0  0  0
 18 23  1  0  0  0  0
 23 24  1  0  0  0  0
 23 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  0  0  0  0
 27 28  1  0  0  0  0
 27 29  1  0  0  0  0
 29 30  1  0  0  0  0
 29 31  1  0  0  0  0
 29 32  1  0  0  0  0
 23 32  1  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 17 34  1  0  0  0  0
  5 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0202432

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C(C)=CC1CC(C)C2(C)C(O1)C=C1C3=C(CCC21C)C1(C)CCC(O)C(C)(C)C1CC3

> <INCHI_IDENTIFIER>
InChI=1S/C31H46O4/c1-18(27(33)34-8)15-20-16-19(2)31(7)26(35-20)17-23-21-9-10-24-28(3,4)25(32)12-13-29(24,5)22(21)11-14-30(23,31)6/h15,17,19-20,24-26,32H,9-14,16H2,1-8H3

> <INCHI_KEY>
UHAGUOVAMDBBBA-UHFFFAOYSA-N

> <FORMULA>
C31H46O4

> <MOLECULAR_WEIGHT>
482.705

> <EXACT_MASS>
482.339609961

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
81

> <JCHEM_AVERAGE_POLARIZABILITY>
57.82014736176774

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate

> <ALOGPS_LOGP>
6.11

> <JCHEM_LOGP>
5.728001926333335

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.553786677396047

> <JCHEM_PKA_STRONGEST_BASIC>
-0.8068077247721303

> <JCHEM_POLAR_SURFACE_AREA>
55.760000000000005

> <JCHEM_REFRACTIVITY>
141.24790000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.49e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 23-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-APR-15         0                                  
HETATM    1  C   UNK     0      18.604   0.619   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      17.139   0.142   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      15.994   1.171   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      16.313   2.678   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      14.530   0.694   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.385   1.724   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.920   1.247   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      11.601  -0.260   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      10.137  -0.737   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.818  -2.243   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.992   0.293   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.517  -1.172   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.311   1.800   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      10.775   2.277   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.977   2.569   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.833   1.537   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.301   1.697   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.397   0.450   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       5.025  -0.956   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.556  -1.116   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       7.460   0.131   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       7.782  -1.375   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.865   0.610   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.493  -0.796   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.961  -0.636   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       0.429  -0.477   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -0.198   0.930   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      -1.730   1.090   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       0.706   2.176   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      -0.678   2.850   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       1.130   3.657   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.238   2.017   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       3.142   3.263   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       4.674   3.103   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      14.211  -0.812   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   35                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   21                                             
CONECT   12   11                                                            
CONECT   13   11   14   15                                                  
CONECT   14   13    7                                                       
CONECT   15   13   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18   34                                                  
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   11   16   22                                             
CONECT   22   21                                                            
CONECT   23   18   24   25   32                                             
CONECT   24   23                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   31   32                                             
CONECT   30   29                                                            
CONECT   31   29                                                            
CONECT   32   29   23   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   17                                                       
CONECT   35    5                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   78    0
END

View in JSmol

Synonyms

Value	Source
Methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0,.0,.0,]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoic acid	Generator
Methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoic acid	Generator

Chemical Formula

C₃₁H₄₆O₄

Average Mass

482.7050 Da

Monoisotopic Mass

482.33961 Da

IUPAC Name

methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate

Traditional Name

methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate

CAS Registry Number

Not Available

SMILES

COC(=O)C(C)=CC1CC(C)C2(C)C(O1)C=C1C3=C(CCC21C)C1(C)CCC(O)C(C)(C)C1CC3

InChI Identifier

InChI=1S/C31H46O4/c1-18(27(33)34-8)15-20-16-19(2)31(7)26(35-20)17-23-21-9-10-24-28(3,4)25(32)12-13-29(24,5)22(21)11-14-30(23,31)6/h15,17,19-20,24-26,32H,9-14,16H2,1-8H3

InChI Key

UHAGUOVAMDBBBA-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
Garcinia speciosa	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 3-hydroxysteroids. These are steroids carrying a hydroxyl group at the 3-position of the steroid backbone.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Hydroxysteroids

Direct Parent

3-hydroxysteroids

Alternative Parents

Substituents

3-hydroxysteroid
Fatty acid ester
Oxane
Fatty acyl
Cyclic alcohol
Methyl ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Oxacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid derivative
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
Alcohol
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	6.11	ALOGPS
logP	5.73	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	19.55	ChemAxon
pKa (Strongest Basic)	-0.81	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	3	ChemAxon
Refractivity	141.25 m³·mol⁻¹	ChemAxon
Polarizability	57.82 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	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate (NP0202432)

MOL for NP0202432 (methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate)

3D MOL for NP0202432 (methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate)

3D SDF for NP0202432 (methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate)

3D-SDF for NP0202432 (methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate)

PDB for NP0202432 (methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate)

3D PDB for NP0202432 (methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate)

SMILES for NP0202432 (methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate)

INCHI for NP0202432 (methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate)

Structure for NP0202432 (methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate)

3D Structure for NP0202432 (methyl 3-{17-hydroxy-8,9,10,14,18,18-hexamethyl-5-oxapentacyclo[11.8.0.0²,¹⁰.0⁴,⁹.0¹⁴,¹⁹]henicosa-1(13),2-dien-6-yl}-2-methylprop-2-enoate)