NP-MRD: Showing NP-Card for (1s,2r,4s,7s,8s,11r,12r,17r,19r)-7-(5-acetylfuran-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl acetate (NP0306299)

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Record Information

Version

2.0

Created at

2022-09-10 22:41:13 UTC

Updated at

2022-09-10 22:41:14 UTC

NP-MRD ID

NP0306299

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,2r,4s,7s,8s,11r,12r,17r,19r)-7-(5-acetylfuran-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl acetate

Description

23-Acetylgedunin 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. Based on a literature review very few articles have been published on 23-acetylgedunin.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309112200412D          

 38 43  0  0  1  0            999 V2000
    3.1449    3.0630    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


  Mrv1652309112200412D          

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    1.7946    1.3480    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5246    0.5684    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.3347    0.7243    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2644    1.5463    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  7  6  1  1  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  8 11  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
  7 15  1  0  0  0  0
 15 16  1  1  0  0  0
 15 17  1  0  0  0  0
 17 18  1  1  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  6  0  0  0
 20 22  1  0  0  0  0
 22 23  1  6  0  0  0
 23 24  2  0  0  0  0
 24 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  2  0  0  0  0
 26 30  2  0  0  0  0
 23 30  1  0  0  0  0
 22 31  1  0  0  0  0
 31 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 34 35  1  1  0  0  0
 36 35  1  1  0  0  0
 34 36  1  0  0  0  0
 20 36  1  0  0  0  0
 36 37  1  0  0  0  0
  5 37  1  0  0  0  0
 17 37  1  0  0  0  0
 37 38  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0306299

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](OC(=O)[C@H]4O[C@@]34[C@]12C)C1=COC(=C1)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C30H36O8/c1-15(31)18-12-17(14-35-18)23-28(6)11-8-19-27(5)10-9-21(33)26(3,4)20(27)13-22(36-16(2)32)29(19,7)30(28)24(38-30)25(34)37-23/h9-10,12,14,19-20,22-24H,8,11,13H2,1-7H3/t19-,20+,22-,23+,24-,27-,28+,29+,30-/m1/s1

> <INCHI_KEY>
ISWPEACHBAMEGH-LZFYJYPSSA-N

> <FORMULA>
C30H36O8

> <MOLECULAR_WEIGHT>
524.61

> <EXACT_MASS>
524.241018119

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
74

> <JCHEM_AVERAGE_POLARIZABILITY>
54.923711879588474

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1S,2R,4S,7R,8S,11R,12R,17R,19R)-7-(5-acetylfuran-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0^{2,4}.0^{2,8}.0^{12,17}]nonadec-13-en-19-yl acetate

> <JCHEM_LOGP>
3.7776329553333325

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.304720301067118

> <JCHEM_PKA_STRONGEST_BASIC>
-3.0251615741892404

> <JCHEM_POLAR_SURFACE_AREA>
112.41000000000003

> <JCHEM_REFRACTIVITY>
135.2733

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
(1S,2R,4S,7R,8S,11R,12R,17R,19R)-7-(5-acetylfuran-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0^{2,4}.0^{2,8}.0^{12,17}]nonadec-13-en-19-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 11-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-SEP-22         0                                  
HETATM    1  C   UNK     0       5.870   5.718   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.358   5.427   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       3.350   6.591   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       3.854   3.971   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       4.862   2.807   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.375   3.098   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.383   1.934   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.895   2.225   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.346   3.664   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      10.216   3.016   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.903   1.061   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      11.415   1.352   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       9.399  -0.394   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.887  -0.685   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.879   0.479   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.375  -0.976   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       5.366   0.188   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       4.862  -1.267   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.350  -1.558   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.342  -0.394   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       1.838  -1.849   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       0.830  -0.685   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.326  -2.140   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.206  -3.403   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       0.277  -4.632   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0      -1.178  -4.128   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      -2.441  -5.009   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -2.310  -6.543   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      -3.835  -4.355   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      -1.148  -2.588   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0      -0.179   0.479   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       0.326   1.934   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      -0.683   3.098   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       1.838   2.225   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       3.350   2.516   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       2.846   1.061   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.358   1.352   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       4.227   2.886   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   37                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8   15                                                  
CONECT    8    7    9   10   11                                             
CONECT    9    8                                                            
CONECT   10    8                                                            
CONECT   11    8   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14    7   16   17                                             
CONECT   16   15                                                            
CONECT   17   15   18   37                                                  
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22   36                                             
CONECT   21   20                                                            
CONECT   22   20   23   31                                                  
CONECT   23   22   24   30                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27   30                                                  
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27                                                            
CONECT   30   26   23                                                       
CONECT   31   22   32                                                       
CONECT   32   31   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   36                                                  
CONECT   35   34   36                                                       
CONECT   36   35   34   20   37                                             
CONECT   37   36    5   17   38                                             
CONECT   38   37                                                            
MASTER        0    0    0    0    0    0    0    0   38    0   86    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₃₆O₈

Average Mass

524.6100 Da

Monoisotopic Mass

524.24102 Da

IUPAC Name

(1S,2R,4S,7R,8S,11R,12R,17R,19R)-7-(5-acetylfuran-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0^{2,4}.0^{2,8}.0^{12,17}]nonadec-13-en-19-yl acetate

Traditional Name

(1S,2R,4S,7R,8S,11R,12R,17R,19R)-7-(5-acetylfuran-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0^{2,4}.0^{2,8}.0^{12,17}]nonadec-13-en-19-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1C[C@H]2C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](OC(=O)[C@H]4O[C@@]34[C@]12C)C1=COC(=C1)C(C)=O

InChI Identifier

InChI=1S/C30H36O8/c1-15(31)18-12-17(14-35-18)23-28(6)11-8-19-27(5)10-9-21(33)26(3,4)20(27)13-22(36-16(2)32)29(19,7)30(28)24(38-30)25(34)37-23/h9-10,12,14,19-20,22-24H,8,11,13H2,1-7H3/t19-,20+,22-,23+,24-,27-,28+,29+,30-/m1/s1

InChI Key

ISWPEACHBAMEGH-LZFYJYPSSA-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

Not Available

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
Naphthopyran
Naphthalene
Aryl ketone
Aryl alkyl ketone
Delta valerolactone
Dioxepane
Delta_valerolactone
1,4-dioxepane
Cyclohexenone
Dicarboxylic acid or derivatives
Oxane
Pyran
Heteroaromatic compound
Furan
Cyclic ketone
Carboxylic acid ester
Lactone
Ketone
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Organoheterocyclic compound
Oxirane
Ether
Organooxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxygen compound
Organic oxide
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	3.78	ChemAxon
pKa (Strongest Acidic)	14.3	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	112.41 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	135.27 m³·mol⁻¹	ChemAxon
Polarizability	54.92 Å³	ChemAxon
Number of Rings	6	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

8896195

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10720857

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,2r,4s,7s,8s,11r,12r,17r,19r)-7-(5-acetylfuran-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl acetate (NP0306299)

MOL for NP0306299 ((1s,2r,4s,7s,8s,11r,12r,17r,19r)-7-(5-acetylfuran-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl acetate)

3D MOL for NP0306299 ((1s,2r,4s,7s,8s,11r,12r,17r,19r)-7-(5-acetylfuran-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl acetate)

3D SDF for NP0306299 ((1s,2r,4s,7s,8s,11r,12r,17r,19r)-7-(5-acetylfuran-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl acetate)

3D-SDF for NP0306299 ((1s,2r,4s,7s,8s,11r,12r,17r,19r)-7-(5-acetylfuran-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl acetate)

PDB for NP0306299 ((1s,2r,4s,7s,8s,11r,12r,17r,19r)-7-(5-acetylfuran-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl acetate)

3D PDB for NP0306299 ((1s,2r,4s,7s,8s,11r,12r,17r,19r)-7-(5-acetylfuran-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl acetate)

SMILES for NP0306299 ((1s,2r,4s,7s,8s,11r,12r,17r,19r)-7-(5-acetylfuran-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl acetate)

INCHI for NP0306299 ((1s,2r,4s,7s,8s,11r,12r,17r,19r)-7-(5-acetylfuran-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl acetate)

Structure for NP0306299 ((1s,2r,4s,7s,8s,11r,12r,17r,19r)-7-(5-acetylfuran-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl acetate)

3D Structure for NP0306299 ((1s,2r,4s,7s,8s,11r,12r,17r,19r)-7-(5-acetylfuran-3-yl)-1,8,12,16,16-pentamethyl-5,15-dioxo-3,6-dioxapentacyclo[9.8.0.0²,⁴.0²,⁸.0¹²,¹⁷]nonadec-13-en-19-yl acetate)