NP-MRD: Showing NP-Card for 10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]heptacosa-6(14),8,10,12,20-pentaen-24-yl acetate (NP0264951)

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Record Information

Version

2.0

Created at

2022-09-08 08:45:25 UTC

Updated at

2022-09-08 08:45:25 UTC

NP-MRD ID

NP0264951

Secondary Accession Numbers

None

Natural Product Identification

Common Name

10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]heptacosa-6(14),8,10,12,20-pentaen-24-yl acetate

Description

10-Chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]Heptacosa-6(14),8(13),9,11,20-pentaen-24-yl acetate belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. Based on a literature review very few articles have been published on 10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]Heptacosa-6(14),8(13),9,11,20-pentaen-24-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082210452D          

 37 43  0  0  0  0            999 V2000
   -0.5847   -0.3275    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


  Mrv1652309082210452D          

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  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 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
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  2  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 25 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 20 29  1  0  0  0  0
 23 29  1  0  0  0  0
 21 30  1  0  0  0  0
 18 30  1  0  0  0  0
 12 30  1  0  0  0  0
 30 31  1  0  0  0  0
 14 32  1  0  0  0  0
  9 32  1  0  0  0  0
 32 33  2  0  0  0  0
 33 34  1  0  0  0  0
 34 35  2  0  0  0  0
 34 36  1  0  0  0  0
  5 36  1  0  0  0  0
 36 37  1  0  0  0  0
  9 37  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0264951

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1(C)COC23CCC4(C)C5(C)C(CC6=C5NC5=CC(Cl)=CC=C65)CCC4(O)C2=CC(=O)C1O3

> <INCHI_IDENTIFIER>
InChI=1S/C29H32ClNO6/c1-15(32)36-25(2)14-35-29-10-9-26(3)27(4)16(7-8-28(26,34)22(29)13-21(33)24(25)37-29)11-19-18-6-5-17(30)12-20(18)31-23(19)27/h5-6,12-13,16,24,31,34H,7-11,14H2,1-4H3

> <INCHI_KEY>
TXNJCXRRMWHWPI-UHFFFAOYSA-N

> <FORMULA>
C29H32ClNO6

> <MOLECULAR_WEIGHT>
526.03

> <EXACT_MASS>
525.1918155

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
69

> <JCHEM_AVERAGE_POLARIZABILITY>
56.35954960431292

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0^{1,20}.0^{4,19}.0^{5,16}.0^{6,14}.0^{8,13}]heptacosa-6(14),8,10,12,20-pentaen-24-yl acetate

> <JCHEM_LOGP>
4.364661445333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.478364040423127

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.617180143089769

> <JCHEM_PKA_STRONGEST_BASIC>
-3.40336150710187

> <JCHEM_POLAR_SURFACE_AREA>
97.85000000000001

> <JCHEM_REFRACTIVITY>
136.7841

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0^{1,20}.0^{4,19}.0^{5,16}.0^{6,14}.0^{8,13}]heptacosa-6(14),8,10,12,20-pentaen-24-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -1.091  -0.611   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.773   0.895   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.919   1.924   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       0.691   1.373   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.837   0.344   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.768  -0.765   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.853   1.557   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       4.290   0.957   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.400  -0.685   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       5.782   0.300   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.339   0.032   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.783  -1.436   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.852  -0.327   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       6.700  -2.531   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       5.621  -3.630   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       7.107  -4.016   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       8.596  -4.407   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.679  -3.312   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.218  -3.385   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.762  -1.944   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.560  -0.981   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0      11.104   0.459   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0      12.643   0.387   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.726   1.482   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      15.215   1.091   0.000  0.00  0.00           C+0
HETATM   26 Cl   UNK     0      16.298   2.186   0.000  0.00  0.00          Cl+0
HETATM   27  C   UNK     0      15.622  -0.394   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      14.539  -1.489   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      13.049  -1.098   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.273  -1.827   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.506  -0.305   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       5.142  -2.135   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.091  -3.293   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       2.614  -2.676   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0       1.233  -3.358   0.000  0.00  0.00           O+0
HETATM   36  C   UNK     0       3.074  -0.934   0.000  0.00  0.00           C+0
HETATM   37  O   UNK     0       2.242  -1.262   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   36                                             
CONECT    6    5                                                            
CONECT    7    5    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   32   37                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   30                                             
CONECT   13   12                                                            
CONECT   14   12   15   16   32                                             
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   30                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   29                                                  
CONECT   21   20   22   30                                                  
CONECT   22   21   23                                                       
CONECT   23   22   24   29                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   20   23                                                  
CONECT   30   21   18   12   31                                             
CONECT   31   30                                                            
CONECT   32   14    9   33                                                  
CONECT   33   32   34                                                       
CONECT   34   33   35   36                                                  
CONECT   35   34                                                            
CONECT   36   34    5   37                                                  
CONECT   37   36    9                                                       
MASTER        0    0    0    0    0    0    0    0   37    0   86    0
END

View in JSmol

Synonyms

Value	Source
10-Chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0,.0,.0,.0,.0,]heptacosa-6(14),8(13),9,11,20-pentaen-24-yl acetic acid	Generator

Chemical Formula

C₂₉H₃₂ClNO₆

Average Mass

526.0300 Da

Monoisotopic Mass

525.19182 Da

IUPAC Name

10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0^{1,20}.0^{4,19}.0^{5,16}.0^{6,14}.0^{8,13}]heptacosa-6(14),8,10,12,20-pentaen-24-yl acetate

Traditional Name

10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0^{1,20}.0^{4,19}.0^{5,16}.0^{6,14}.0^{8,13}]heptacosa-6(14),8,10,12,20-pentaen-24-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1(C)COC23CCC4(C)C5(C)C(CC6=C5NC5=CC(Cl)=CC=C65)CCC4(O)C2=CC(=O)C1O3

InChI Identifier

InChI=1S/C29H32ClNO6/c1-15(32)36-25(2)14-35-29-10-9-26(3)27(4)16(7-8-28(26,34)22(29)13-21(33)24(25)37-29)11-19-18-6-5-17(30)12-20(18)31-23(19)27/h5-6,12-13,16,24,31,34H,7-11,14H2,1-4H3

InChI Key

TXNJCXRRMWHWPI-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

Not Available

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthopyrans. Naphthopyrans are compounds containing a pyran ring fused to a naphthalene moiety. Furan is a 6 membered-ring non-aromatic ring with five carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Naphthopyrans

Sub Class

Not Available

Direct Parent

Naphthopyrans

Alternative Parents

Substituents

Naphthopyran
3-alkylindole
Naphthalene
Indole or derivatives
Indole
Ketal
Dihydropyranone
Benzenoid
Pyran
Aryl halide
Aryl chloride
Meta-dioxane
Heteroaromatic compound
Tertiary alcohol
Pyrrole
Cyclic alcohol
Ketone
Carboxylic acid ester
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Acetal
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Organochloride
Organohalogen compound
Carbonyl group
Alcohol
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	4.36	ChemAxon
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	-3.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	97.85 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	136.78 m³·mol⁻¹	ChemAxon
Polarizability	56.36 Å³	ChemAxon
Number of Rings	7	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

129008994

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]heptacosa-6(14),8,10,12,20-pentaen-24-yl acetate (NP0264951)

MOL for NP0264951 (10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]heptacosa-6(14),8,10,12,20-pentaen-24-yl acetate)

3D MOL for NP0264951 (10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]heptacosa-6(14),8,10,12,20-pentaen-24-yl acetate)

3D SDF for NP0264951 (10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]heptacosa-6(14),8,10,12,20-pentaen-24-yl acetate)

3D-SDF for NP0264951 (10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]heptacosa-6(14),8,10,12,20-pentaen-24-yl acetate)

PDB for NP0264951 (10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]heptacosa-6(14),8,10,12,20-pentaen-24-yl acetate)

3D PDB for NP0264951 (10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]heptacosa-6(14),8,10,12,20-pentaen-24-yl acetate)

SMILES for NP0264951 (10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]heptacosa-6(14),8,10,12,20-pentaen-24-yl acetate)

INCHI for NP0264951 (10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]heptacosa-6(14),8,10,12,20-pentaen-24-yl acetate)

Structure for NP0264951 (10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]heptacosa-6(14),8,10,12,20-pentaen-24-yl acetate)

3D Structure for NP0264951 (10-chloro-19-hydroxy-4,5,24-trimethyl-22-oxo-26,27-dioxa-7-azaheptacyclo[21.3.1.0¹,²⁰.0⁴,¹⁹.0⁵,¹⁶.0⁶,¹⁴.0⁸,¹³]heptacosa-6(14),8,10,12,20-pentaen-24-yl acetate)