NP-MRD: Showing NP-Card for 13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate (NP0142551)

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Record Information

Version

2.0

Created at

2022-09-01 21:06:57 UTC

Updated at

2022-09-01 21:06:57 UTC

NP-MRD ID

NP0142551

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate

Description

13-(Acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]Nonadecan-16-yl butanoate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. 13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate is found in Briareum excavatum and Briareum stechei. 13-(Acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]Nonadecan-16-yl butanoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004161516212D          

 37 41  0  0  0  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1533004161516212D          

 37 41  0  0  0  0            999 V2000
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    1.6569   -2.4907    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8453   -2.3425    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3794   -1.7138    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  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 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
 11 16  1  0  0  0  0
 16 17  1  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 20  1  0  0  0  0
 20 21  2  0  0  0  0
 20 22  1  0  0  0  0
 22 23  1  0  0  0  0
 16 23  1  0  0  0  0
 23 24  1  0  0  0  0
 24 25  1  0  0  0  0
 24 26  1  0  0  0  0
 26 27  2  0  0  0  0
 26 28  1  0  0  0  0
 28 29  1  0  0  0  0
 29 30  1  0  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 31 33  1  0  0  0  0
 10 33  1  0  0  0  0
 33 34  1  0  0  0  0
 33 35  1  0  0  0  0
 35 36  1  0  0  0  0
 36 37  1  0  0  0  0
  7 37  1  0  0  0  0
 35 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0142551

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CCCC(=O)OC1C2OC2C2(C)C(C1C)C(OC(C)=O)C1(O)C(C)C(=O)OC1C(Cl)C(=C)C1OC1C2O

> <INCHI_IDENTIFIER>
InChI=1S/C26H35ClO10/c1-7-8-13(29)34-16-9(2)14-21(33-12(5)28)26(32)11(4)24(31)37-22(26)15(27)10(3)17-18(35-17)20(30)25(14,6)23-19(16)36-23/h9,11,14-23,30,32H,3,7-8H2,1-2,4-6H3

> <INCHI_KEY>
OTELLKVQFOZXJO-UHFFFAOYSA-N

> <FORMULA>
C26H35ClO10

> <MOLECULAR_WEIGHT>
543.01

> <EXACT_MASS>
542.191875

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.761785529961266

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate

> <ALOGPS_LOGP>
2.37

> <JCHEM_LOGP>
1.6182087363333344

> <ALOGPS_LOGS>
-3.07

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
13.597013802006124

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.346109407824347

> <JCHEM_PKA_STRONGEST_BASIC>
-3.4242449925601903

> <JCHEM_POLAR_SURFACE_AREA>
144.42000000000002

> <JCHEM_REFRACTIVITY>
124.94339999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.67e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 16-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   16-APR-15         0                                  
HETATM    1  C   UNK     0      -1.012   2.879   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.494   1.428   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.021   1.152   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.539  -0.298   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0       0.542  -1.472   0.000  0.00  0.00           O+0
HETATM    6  O   UNK     0       3.054  -0.575   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       3.572  -2.025   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.087  -2.302   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.084  -1.128   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.605  -3.752   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.101  -3.389   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       7.218  -1.853   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       8.606  -1.187   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       8.723   0.349   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       9.878  -2.056   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.526  -3.974   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       8.162  -2.478   0.000  0.00  0.00           O+0
HETATM   18  C   UNK     0       9.523  -2.801   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      10.834  -1.993   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.947  -3.386   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      12.258  -2.578   0.000  0.00  0.00           O+0
HETATM   22  O   UNK     0      10.830  -4.922   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0       9.334  -5.285   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.217  -6.821   0.000  0.00  0.00           C+0
HETATM   25 Cl   UNK     0      10.641  -7.406   0.000  0.00  0.00          Cl+0
HETATM   26  C   UNK     0       8.220  -7.995   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.028  -9.305   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.724  -8.358   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       5.504  -9.299   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       5.299  -7.772   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.491  -6.462   0.000  0.00  0.00           C+0
HETATM   32  O   UNK     0       2.995  -6.825   0.000  0.00  0.00           O+0
HETATM   33  C   UNK     0       4.608  -4.926   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       3.389  -5.867   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       3.093  -4.649   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.578  -4.373   0.000  0.00  0.00           O+0
HETATM   37  C   UNK     0       2.575  -3.199   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   37                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11   33                                                  
CONECT   11   10   12   16                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   11   17   18   23                                             
CONECT   17   16                                                            
CONECT   18   16   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   16   24                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28   30                                                       
CONECT   30   29   28   31                                                  
CONECT   31   30   32   33                                                  
CONECT   32   31                                                            
CONECT   33   31   10   34   35                                             
CONECT   34   33                                                            
CONECT   35   33   36   37                                                  
CONECT   36   35   37                                                       
CONECT   37   36    7   35                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   82    0
END

View in JSmol

Synonyms

Value	Source
13-(Acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0,.0,.0,]nonadecan-16-yl butanoic acid	Generator
13-(Acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoic acid	Generator

Chemical Formula

C₂₆H₃₅ClO₁₀

Average Mass

543.0100 Da

Monoisotopic Mass

542.19188 Da

IUPAC Name

13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate

Traditional Name

13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate

CAS Registry Number

Not Available

SMILES

CCCC(=O)OC1C2OC2C2(C)C(C1C)C(OC(C)=O)C1(O)C(C)C(=O)OC1C(Cl)C(=C)C1OC1C2O

InChI Identifier

InChI=1S/C26H35ClO10/c1-7-8-13(29)34-16-9(2)14-21(33-12(5)28)26(32)11(4)24(31)37-22(26)15(27)10(3)17-18(35-17)20(30)25(14,6)23-19(16)36-23/h9,11,14-23,30,32H,3,7-8H2,1-2,4-6H3

InChI Key

OTELLKVQFOZXJO-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
Briareum excavatum	LOTUS Database	35616633
Briareum stechei	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Fatty acid ester
Oxepane
Gamma butyrolactone
Fatty acyl
Tetrahydrofuran
Tertiary alcohol
Carboxylic acid ester
Lactone
Secondary alcohol
Dialkyl ether
Oxirane
Ether
Oxacycle
Organoheterocyclic compound
Hydrocarbon derivative
Organic oxide
Alkyl chloride
Alcohol
Organic oxygen compound
Alkyl halide
Organohalogen compound
Organochloride
Organooxygen compound
Carbonyl group
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	2.37	ALOGPS
logP	1.62	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Acidic)	12.35	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	144.42 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	124.94 m³·mol⁻¹	ChemAxon
Polarizability	53.76 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

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

73836895

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate (NP0142551)

MOL for NP0142551 (13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate)

3D MOL for NP0142551 (13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate)

3D SDF for NP0142551 (13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate)

3D-SDF for NP0142551 (13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate)

PDB for NP0142551 (13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate)

3D PDB for NP0142551 (13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate)

SMILES for NP0142551 (13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate)

INCHI for NP0142551 (13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate)

Structure for NP0142551 (13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate)

3D Structure for NP0142551 (13-(acetyloxy)-7-chloro-2,12-dihydroxy-1,11,15-trimethyl-6-methylidene-10-oxo-4,9,18-trioxapentacyclo[12.5.0.0³,⁵.0⁸,¹².0¹⁷,¹⁹]nonadecan-16-yl butanoate)