NP-MRD: Showing NP-Card for (1r,2s,3s,5r,6r,8s,10e,12r,13s,15r,16s,17s,18s)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹³,¹⁵]icosa-10,19-dien-7-one (NP0287045)

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Record Information

Version

2.0

Created at

2022-09-09 15:55:10 UTC

Updated at

2022-09-09 15:55:10 UTC

NP-MRD ID

NP0287045

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2s,3s,5r,6r,8s,10e,12r,13s,15r,16s,17s,18s)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹³,¹⁵]icosa-10,19-dien-7-one

Description

(1R,2S,3S,5R,6R,8S,10E,12R,13S,15R,16S,17S,18S)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹³,¹⁵]Icosa-10,19-dien-7-one belongs to the class of organic compounds known as isoindoles and derivatives. These are polycyclic compounds containing an isoindole moiety, which is structurally characterized by a cyclohexadiene fused to a pyrrole ring. (1r,2s,3s,5r,6r,8s,10e,12r,13s,15r,16s,17s,18s)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹³,¹⁵]icosa-10,19-dien-7-one is found in Xylaria obovata. Based on a literature review very few articles have been published on (1R,2S,3S,5R,6R,8S,10E,12R,13S,15R,16S,17S,18S)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹³,¹⁵]Icosa-10,19-dien-7-one.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092217552D          

 35 40  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309092217552D          

 35 40  0  0  1  0            999 V2000
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  7  8  1  6  0  0  0
  8  9  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  1  0  0  0
  9 11  1  0  0  0  0
 11 12  1  1  0  0  0
 11 13  1  0  0  0  0
 13 14  1  6  0  0  0
 14 15  1  6  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 16 21  1  0  0  0  0
 14 22  1  0  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 25 23  1  1  0  0  0
 13 25  1  0  0  0  0
  6 25  1  0  0  0  0
 25 26  1  0  0  0  0
 26 27  1  6  0  0  0
 26 28  1  0  0  0  0
 28 29  1  1  0  0  0
 30 29  1  1  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  6  0  0  0
 31 33  1  1  0  0  0
 31 34  1  0  0  0  0
  2 34  1  0  0  0  0
 34 35  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0287045

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1[C@@H]2[C@H](CC3=CC=CC=C3)N=C(O)[C@@]22[C@@H](\C=C\C[C@H](C)C(=O)[C@](C)(O)[C@@H]3O[C@H]3[C@H]2O)[C@@H]2O[C@]12C

> <INCHI_IDENTIFIER>
InChI=1S/C28H35NO6/c1-14-9-8-12-17-23-27(4,35-23)15(2)19-18(13-16-10-6-5-7-11-16)29-25(32)28(17,19)22(31)20-24(34-20)26(3,33)21(14)30/h5-8,10-12,14-15,17-20,22-24,31,33H,9,13H2,1-4H3,(H,29,32)/b12-8+/t14-,15-,17-,18-,19+,20-,22+,23-,24+,26-,27+,28-/m0/s1

> <INCHI_KEY>
CROHHODFFQILKQ-DGXMEGQVSA-N

> <FORMULA>
C28H35NO6

> <MOLECULAR_WEIGHT>
481.589

> <EXACT_MASS>
481.246437851

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
70

> <JCHEM_AVERAGE_POLARIZABILITY>
51.576448819157925

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2S,3S,5R,6R,8S,10E,12R,13S,15R,16S,17S,18S)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0^{1,17}.0^{3,5}.0^{13,15}]icosa-10,19-dien-7-one

> <JCHEM_LOGP>
2.389624860317931

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
12.217995362537057

> <JCHEM_PKA_STRONGEST_ACIDIC>
3.133470016652533

> <JCHEM_PKA_STRONGEST_BASIC>
5.493568548118767

> <JCHEM_POLAR_SURFACE_AREA>
115.18

> <JCHEM_REFRACTIVITY>
129.2298

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,3S,5R,6R,8S,10E,12R,13S,15R,16S,17S,18S)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0^{1,17}.0^{3,5}.0^{13,15}]icosa-10,19-dien-7-one

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 09-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   09-SEP-22         0                                  
HETATM    1  C   UNK     0      10.650   0.614   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.093   2.217   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.108   1.034   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.678   1.605   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.779   3.142   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.795   4.510   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.271   4.290   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       3.747   4.070   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       4.319   5.500   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.764   5.937   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.890   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.890   8.180   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.414   7.150   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.271   8.430   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.650   9.928   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.724  11.058   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       7.287  12.535   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.348  13.652   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.845  13.292   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      10.282  11.815   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       9.222  10.699   0.000  0.00  0.00           C+0
HETATM   22  N   UNK     0       8.753   8.011   0.000  0.00  0.00           N+0
HETATM   23  C   UNK     0       8.463   6.733   0.000  0.00  0.00           C+0
HETATM   24  O   UNK     0      10.098   6.343   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0       7.367   5.940   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.891   6.160   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      10.028   7.539   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       9.844   4.950   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.796   3.740   0.000  0.00  0.00           O+0
HETATM   30  C   UNK     0      11.368   5.170   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      12.321   3.960   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      13.501   5.082   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      13.720   3.147   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      11.749   2.530   0.000  0.00  0.00           C+0
HETATM   35  O   UNK     0      12.956   1.431   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   34                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   25                                                  
CONECT    7    6    8    9                                                  
CONECT    8    7    9                                                       
CONECT    9    8    7   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   25                                                  
CONECT   14   13   15   22                                                  
CONECT   15   14   16                                                       
CONECT   16   15   17   21                                                  
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   16                                                       
CONECT   22   14   23                                                       
CONECT   23   22   24   25                                                  
CONECT   24   23                                                            
CONECT   25   23   13    6   26                                             
CONECT   26   25   27   28                                                  
CONECT   27   26                                                            
CONECT   28   26   29   30                                                  
CONECT   29   28   30                                                       
CONECT   30   29   28   31                                                  
CONECT   31   30   32   33   34                                             
CONECT   32   31                                                            
CONECT   33   31                                                            
CONECT   34   31    2   35                                                  
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   80    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₅NO₆

Average Mass

481.5890 Da

Monoisotopic Mass

481.24644 Da

IUPAC Name

(1R,2S,3S,5R,6R,8S,10E,12R,13S,15R,16S,17S,18S)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0^{1,17}.0^{3,5}.0^{13,15}]icosa-10,19-dien-7-one

Traditional Name

(1R,2S,3S,5R,6R,8S,10E,12R,13S,15R,16S,17S,18S)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0^{1,17}.0^{3,5}.0^{13,15}]icosa-10,19-dien-7-one

CAS Registry Number

Not Available

SMILES

C[C@H]1[C@@H]2[C@H](CC3=CC=CC=C3)N=C(O)[C@@]22[C@@H](\C=C\C[C@H](C)C(=O)[C@](C)(O)[C@@H]3O[C@H]3[C@H]2O)[C@@H]2O[C@]12C

InChI Identifier

InChI=1S/C28H35NO6/c1-14-9-8-12-17-23-27(4,35-23)15(2)19-18(13-16-10-6-5-7-11-16)29-25(32)28(17,19)22(31)20-24(34-20)26(3,33)21(14)30/h5-8,10-12,14-15,17-20,22-24,31,33H,9,13H2,1-4H3,(H,29,32)/b12-8+/t14-,15-,17-,18-,19+,20-,22+,23-,24+,26-,27+,28-/m0/s1

InChI Key

CROHHODFFQILKQ-DGXMEGQVSA-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
Xylaria obovata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as isoindoles and derivatives. These are polycyclic compounds containing an isoindole moiety, which is structurally characterized by a cyclohexadiene fused to a pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Isoindoles and derivatives

Sub Class

Not Available

Direct Parent

Isoindoles and derivatives

Alternative Parents

Substituents

Isoindole or derivatives
Oxepane
Acyloin
Monocyclic benzene moiety
Benzenoid
Pyrroline
Tertiary alcohol
Cyclic carboximidic acid
Ketone
Secondary alcohol
Cyclic ketone
Oxacycle
Azacycle
Dialkyl ether
Oxirane
Ether
Organic 1,3-dipolar compound
Polyol
Propargyl-type 1,3-dipolar organic compound
Organopnictogen compound
Organonitrogen compound
Organooxygen compound
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Alcohol
Hydrocarbon derivative
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	2.39	ChemAxon
pKa (Strongest Acidic)	3.13	ChemAxon
pKa (Strongest Basic)	5.49	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	115.18 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	129.23 m³·mol⁻¹	ChemAxon
Polarizability	51.58 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	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

163187534

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2s,3s,5r,6r,8s,10e,12r,13s,15r,16s,17s,18s)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹³,¹⁵]icosa-10,19-dien-7-one (NP0287045)

MOL for NP0287045 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,15r,16s,17s,18s)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹³,¹⁵]icosa-10,19-dien-7-one)

3D MOL for NP0287045 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,15r,16s,17s,18s)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹³,¹⁵]icosa-10,19-dien-7-one)

3D SDF for NP0287045 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,15r,16s,17s,18s)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹³,¹⁵]icosa-10,19-dien-7-one)

3D-SDF for NP0287045 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,15r,16s,17s,18s)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹³,¹⁵]icosa-10,19-dien-7-one)

PDB for NP0287045 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,15r,16s,17s,18s)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹³,¹⁵]icosa-10,19-dien-7-one)

3D PDB for NP0287045 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,15r,16s,17s,18s)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹³,¹⁵]icosa-10,19-dien-7-one)

SMILES for NP0287045 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,15r,16s,17s,18s)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹³,¹⁵]icosa-10,19-dien-7-one)

INCHI for NP0287045 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,15r,16s,17s,18s)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹³,¹⁵]icosa-10,19-dien-7-one)

Structure for NP0287045 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,15r,16s,17s,18s)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹³,¹⁵]icosa-10,19-dien-7-one)

3D Structure for NP0287045 ((1r,2s,3s,5r,6r,8s,10e,12r,13s,15r,16s,17s,18s)-18-benzyl-2,6,20-trihydroxy-6,8,15,16-tetramethyl-4,14-dioxa-19-azapentacyclo[10.8.0.0¹,¹⁷.0³,⁵.0¹³,¹⁵]icosa-10,19-dien-7-one)