NP-MRD: Showing NP-Card for (1s,3s,5r,8s,9r,10s,11r,14r,16s,17r,18s,19s)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylpropanoate (NP0176410)

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Record Information

Version

2.0

Created at

2022-09-03 14:04:10 UTC

Updated at

2022-09-03 14:04:10 UTC

NP-MRD ID

NP0176410

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1s,3s,5r,8s,9r,10s,11r,14r,16s,17r,18s,19s)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylpropanoate

Description

(1S,3S,5R,8S,9R,10S,11R,14R,16S,17R,18S,19S)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-3-yl 2-methylpropanoate belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12. (1s,3s,5r,8s,9r,10s,11r,14r,16s,17r,18s,19s)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylpropanoate is found in Aconitum coreanum. Based on a literature review very few articles have been published on (1S,3S,5R,8S,9R,10S,11R,14R,16S,17R,18S,19S)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]Nonadecan-3-yl 2-methylpropanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032216042D          

 30 36  0  0  1  0            999 V2000
   -1.2475    0.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903    0.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1988    0.9528    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1128    0.6351    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9516    1.0290    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7866    0.6292    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.4136   -0.0353    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
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 30  8  1  6  0  0  0
  4 30  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309032216042D          

 30 36  0  0  1  0            999 V2000
   -1.2475    0.4022    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3903    0.2968    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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M  END
> <DATABASE_ID>
NP0176410

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)C(=O)O[C@H]1C[C@@]2(C)CN3[C@H]4C[C@]56CC(=C)[C@@H]7[C@@H](O)[C@H]5[C@](C1)([C@@H]24)[C@H]3[C@@]6(O)[C@H]7O

> <INCHI_IDENTIFIER>
InChI=1S/C24H33NO5/c1-10(2)19(28)30-12-6-21(4)9-25-13-8-22-5-11(3)14-15(26)17(22)23(7-12,16(13)21)20(25)24(22,29)18(14)27/h10,12-18,20,26-27,29H,3,5-9H2,1-2,4H3/t12-,13-,14+,15+,16+,17+,18-,20-,21-,22+,23-,24-/m0/s1

> <INCHI_KEY>
BKHLAQWOXOLRLR-NBNRPSMLSA-N

> <FORMULA>
C24H33NO5

> <MOLECULAR_WEIGHT>
415.53

> <EXACT_MASS>
415.235873167

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
63

> <JCHEM_AVERAGE_POLARIZABILITY>
56.541654263998794

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1S,3S,5R,8S,9R,10S,11R,14R,16S,17R,18S,19S)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-yl 2-methylpropanoate

> <JCHEM_LOGP>
0.10670256166666693

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
14.18485503640116

> <JCHEM_PKA_STRONGEST_ACIDIC>
12.813620703337357

> <JCHEM_PKA_STRONGEST_BASIC>
8.782874708059905

> <JCHEM_POLAR_SURFACE_AREA>
90.23

> <JCHEM_REFRACTIVITY>
107.8994

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1S,3S,5R,8S,9R,10S,11R,14R,16S,17R,18S,19S)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.329   0.751   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.728   0.554   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.371   1.778   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.077   1.185   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.643   1.921   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.202   1.174   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.372  -0.066   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.794   0.287   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.483   1.113   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.119   0.778   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       9.124   2.076   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      10.695   2.108   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      11.437   3.458   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      11.493   0.791   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      13.032   0.823   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      10.750  -0.558   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.997  -0.583   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.546  -1.242   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.324  -2.694   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.164  -1.998   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0       5.324  -0.638   0.000  0.00  0.00           N+0
HETATM   22  C   UNK     0       3.898  -1.127   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       2.391  -0.627   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0       1.436  -2.224   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       1.203  -1.750   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.481  -3.467   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      -0.060  -0.854   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       1.363  -0.070   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0       1.407   1.850   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0       3.129   0.314   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   27                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   23   30                                             
CONECT    5    4    6                                                       
CONECT    6    5    7   21                                                  
CONECT    7    6    8   18                                                  
CONECT    8    7    9   22   30                                             
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   10   18                                                       
CONECT   18   17    7   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20    6   22                                                  
CONECT   22   21    8   23                                                  
CONECT   23   22    4   24   25                                             
CONECT   24   23                                                            
CONECT   25   23   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25    2   28                                                  
CONECT   28   27   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28    8    4                                                  
MASTER        0    0    0    0    0    0    0    0   30    0   72    0
END

View in JSmol

Synonyms

Value	Source
(1S,3S,5R,8S,9R,10S,11R,14R,16S,17R,18S,19S)-9,10,19-Trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0,.0,.0,.0,.0,]nonadecan-3-yl 2-methylpropanoic acid	Generator

Chemical Formula

C₂₄H₃₃NO₅

Average Mass

415.5300 Da

Monoisotopic Mass

415.23587 Da

IUPAC Name

(1S,3S,5R,8S,9R,10S,11R,14R,16S,17R,18S,19S)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-yl 2-methylpropanoate

Traditional Name

(1S,3S,5R,8S,9R,10S,11R,14R,16S,17R,18S,19S)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0^{1,8}.0^{5,17}.0^{7,16}.0^{9,14}.0^{14,18}]nonadecan-3-yl 2-methylpropanoate

CAS Registry Number

Not Available

SMILES

CC(C)C(=O)O[C@H]1C[C@@]2(C)CN3[C@H]4C[C@]56CC(=C)[C@@H]7[C@@H](O)[C@H]5[C@](C1)([C@@H]24)[C@H]3[C@@]6(O)[C@H]7O

InChI Identifier

InChI=1S/C24H33NO5/c1-10(2)19(28)30-12-6-21(4)9-25-13-8-22-5-11(3)14-15(26)17(22)23(7-12,16(13)21)20(25)24(22,29)18(14)27/h10,12-18,20,26-27,29H,3,5-9H2,1-2,4H3/t12-,13-,14+,15+,16+,17+,18-,20-,21-,22+,23-,24-/m0/s1

InChI Key

BKHLAQWOXOLRLR-NBNRPSMLSA-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
Aconitum coreanum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as atisane diterpenoids. These are diterpenoids with a structure based on the atisane skeleton, which is a tetracyclic compound containing the [2,2,2]bicyc1ic ring system with the C15-C16 bridge attached at C12.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Atisane diterpenoids

Alternative Parents

Substituents

Atisane diterpenoid
Azaspirodecane
Quinolizidine
Isoindole or derivatives
Isoindoline
Indolizidine
Alkaloid or derivatives
Indole or derivatives
Azepane
Piperidine
N-alkylpyrrolidine
Cyclic alcohol
Pyrrolidine
Tertiary alcohol
Amino acid or derivatives
Tertiary aliphatic amine
1,2-aminoalcohol
Tertiary amine
Secondary alcohol
Carboxylic acid ester
Carboxylic acid derivative
Azacycle
Organoheterocyclic compound
Polyol
Monocarboxylic acid or derivatives
Alcohol
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Amine
Organooxygen compound
Organonitrogen 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	0.11	ChemAxon
pKa (Strongest Acidic)	12.81	ChemAxon
pKa (Strongest Basic)	8.78	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	90.23 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	107.9 m³·mol⁻¹	ChemAxon
Polarizability	56.54 Å³	ChemAxon
Number of Rings	7	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

163005101

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1s,3s,5r,8s,9r,10s,11r,14r,16s,17r,18s,19s)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylpropanoate (NP0176410)

MOL for NP0176410 ((1s,3s,5r,8s,9r,10s,11r,14r,16s,17r,18s,19s)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylpropanoate)

3D MOL for NP0176410 ((1s,3s,5r,8s,9r,10s,11r,14r,16s,17r,18s,19s)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylpropanoate)

3D SDF for NP0176410 ((1s,3s,5r,8s,9r,10s,11r,14r,16s,17r,18s,19s)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylpropanoate)

3D-SDF for NP0176410 ((1s,3s,5r,8s,9r,10s,11r,14r,16s,17r,18s,19s)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylpropanoate)

PDB for NP0176410 ((1s,3s,5r,8s,9r,10s,11r,14r,16s,17r,18s,19s)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylpropanoate)

3D PDB for NP0176410 ((1s,3s,5r,8s,9r,10s,11r,14r,16s,17r,18s,19s)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylpropanoate)

SMILES for NP0176410 ((1s,3s,5r,8s,9r,10s,11r,14r,16s,17r,18s,19s)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylpropanoate)

INCHI for NP0176410 ((1s,3s,5r,8s,9r,10s,11r,14r,16s,17r,18s,19s)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylpropanoate)

Structure for NP0176410 ((1s,3s,5r,8s,9r,10s,11r,14r,16s,17r,18s,19s)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylpropanoate)

3D Structure for NP0176410 ((1s,3s,5r,8s,9r,10s,11r,14r,16s,17r,18s,19s)-9,10,19-trihydroxy-5-methyl-12-methylidene-7-azaheptacyclo[9.6.2.0¹,⁸.0⁵,¹⁷.0⁷,¹⁶.0⁹,¹⁴.0¹⁴,¹⁸]nonadecan-3-yl 2-methylpropanoate)