NP-MRD: Showing NP-Card for (1r,13s,16r,22s)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0²,¹¹.0⁵,¹⁰.0¹⁴,²².0¹⁶,²⁰]tricosa-2(11),3,5(10),8-tetraene-15,21-dione (NP0277375)

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Record Information

Version

2.0

Created at

2022-09-09 01:59:35 UTC

Updated at

2022-09-09 01:59:35 UTC

NP-MRD ID

NP0277375

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,13s,16r,22s)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0²,¹¹.0⁵,¹⁰.0¹⁴,²².0¹⁶,²⁰]tricosa-2(11),3,5(10),8-tetraene-15,21-dione

Description

Speramide B belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. (1r,13s,16r,22s)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0²,¹¹.0⁵,¹⁰.0¹⁴,²².0¹⁶,²⁰]tricosa-2(11),3,5(10),8-tetraene-15,21-dione is found in Aspergillus ochraceus. (1r,13s,16r,22s)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0²,¹¹.0⁵,¹⁰.0¹⁴,²².0¹⁶,²⁰]tricosa-2(11),3,5(10),8-tetraene-15,21-dione was first documented in 2018 (PMID: 30765898). Based on a literature review very few articles have been published on Speramide B.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309092203592D          

 34 39  0  0  1  0            999 V2000
    3.0063    3.4211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9196    1.2401    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.5968    1.7113    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2542    1.2129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  6 34  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309092203592D          

 34 39  0  0  1  0            999 V2000
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 30 32  1  0  0  0  0
 32 33  2  0  0  0  0
 32 34  1  0  0  0  0
 23 34  1  1  0  0  0
  6 34  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0277375

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)(C=C)[C@@]12NC3=C(C=CC4=C3C=CC(C)(C)O4)[C@]1(O)C[C@@H]1N2C(=O)[C@]2(O)CCCN2C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C26H31N3O5/c1-6-22(2,3)26-24(32,14-17-20(30)28-13-7-11-25(28,33)21(31)29(17)26)16-8-9-18-15(19(16)27-26)10-12-23(4,5)34-18/h6,8-10,12,17,27,32-33H,1,7,11,13-14H2,2-5H3/t17-,24+,25+,26-/m0/s1

> <INCHI_KEY>
DMIIGSHOFYCWKW-WBSKELJPSA-N

> <FORMULA>
C26H31N3O5

> <MOLECULAR_WEIGHT>
465.55

> <EXACT_MASS>
465.22637111

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
65

> <JCHEM_AVERAGE_POLARIZABILITY>
49.54731347763112

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,13S,16R,22S)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0^{2,11}.0^{5,10}.0^{14,22}.0^{16,20}]tricosa-2(11),3,5(10),8-tetraene-15,21-dione

> <JCHEM_LOGP>
2.231587419666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
11.845016237309393

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.060143497461542

> <JCHEM_PKA_STRONGEST_BASIC>
0.2727740365739395

> <JCHEM_POLAR_SURFACE_AREA>
102.34

> <JCHEM_REFRACTIVITY>
127.69669999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,13S,16R,22S)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0^{2,11}.0^{5,10}.0^{14,22}.0^{16,20}]tricosa-2(11),3,5(10),8-tetraene-15,21-dione

> <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       5.612   6.386   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.558   5.263   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.004   3.789   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.530   3.343   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.478   4.235   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.450   2.315   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0       6.714   3.194   0.000  0.00  0.00           N+0
HETATM    8  C   UNK     0       7.941   2.264   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.436   0.809   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       8.442  -0.356   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.955  -0.066   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.461   1.388   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.454   2.553   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.959   4.008   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      11.472   4.297   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      12.479   3.132   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      13.452   4.326   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      13.824   2.382   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      11.973   1.678   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       5.896   0.841   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0       6.342  -0.633   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0       4.632  -0.039   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.405   0.892   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       1.892   0.602   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       1.386  -0.852   0.000  0.00  0.00           O+0
HETATM   26  N   UNK     0       0.885   1.768   0.000  0.00  0.00           N+0
HETATM   27  C   UNK     0      -0.655   1.799   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      -1.100   3.273   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       0.164   4.153   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.391   3.222   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       1.742   4.722   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       2.903   3.512   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.409   4.966   0.000  0.00  0.00           O+0
HETATM   34  N   UNK     0       3.910   2.346   0.000  0.00  0.00           N+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5    6                                             
CONECT    4    3                                                            
CONECT    5    3                                                            
CONECT    6    3    7   20   34                                             
CONECT    7    6    8                                                       
CONECT    8    7    9   13                                                  
CONECT    9    8   10   20                                                  
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   19                                                  
CONECT   13   12    8   14                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17   18   19                                             
CONECT   17   16                                                            
CONECT   18   16                                                            
CONECT   19   16   12                                                       
CONECT   20    9    6   21   22                                             
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24   34                                                  
CONECT   24   23   25   26                                                  
CONECT   25   24                                                            
CONECT   26   24   27   30                                                  
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   30                                                       
CONECT   30   29   26   31   32                                             
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   23    6                                                  
MASTER        0    0    0    0    0    0    0    0   34    0   78    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₃₁N₃O₅

Average Mass

465.5500 Da

Monoisotopic Mass

465.22637 Da

IUPAC Name

(1R,13S,16R,22S)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0^{2,11}.0^{5,10}.0^{14,22}.0^{16,20}]tricosa-2(11),3,5(10),8-tetraene-15,21-dione

Traditional Name

(1R,13S,16R,22S)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0^{2,11}.0^{5,10}.0^{14,22}.0^{16,20}]tricosa-2(11),3,5(10),8-tetraene-15,21-dione

CAS Registry Number

Not Available

SMILES

CC(C)(C=C)[C@@]12NC3=C(C=CC4=C3C=CC(C)(C)O4)[C@]1(O)C[C@@H]1N2C(=O)[C@]2(O)CCCN2C1=O

InChI Identifier

InChI=1S/C26H31N3O5/c1-6-22(2,3)26-24(32,14-17-20(30)28-13-7-11-25(28,33)21(31)29(17)26)16-8-9-18-15(19(16)27-26)10-12-23(4,5)34-18/h6,8-10,12,17,27,32-33H,1,7,11,13-14H2,2-5H3/t17-,24+,25+,26-/m0/s1

InChI Key

DMIIGSHOFYCWKW-WBSKELJPSA-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
Aspergillus ochraceus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrroloindoles. Pyrroloindoles are compounds containing a pyrroloindole moiety, which is a tricyclic heterocycle which consists of a pyrrole ring fused to an indole. Pyrrole is 5-membered ring consisting of four carbon atoms and one nitrogen atom. Indole is a bicyclic compound consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Pyrroloindoles

Direct Parent

Pyrroloindoles

Alternative Parents

Substituents

2,2-dimethyl-1-benzopyran
Pyrroloindole
1-benzopyran
Benzopyran
Alpha-amino acid or derivatives
Dihydroindole
Indole
2,5-dioxopiperazine
Dioxopiperazine
N-alkylpiperazine
Secondary aliphatic/aromatic amine
Alkyl aryl ether
Benzenoid
Piperazine
1,4-diazinane
Tertiary carboxylic acid amide
Tertiary alcohol
Pyrrolidine
Pyrrole
Lactam
Carboxamide group
Amino acid or derivatives
Oxacycle
Azacycle
Secondary amine
Ether
Carboxylic acid derivative
Alkanolamine
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Amine
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	2.23	ChemAxon
pKa (Strongest Acidic)	11.06	ChemAxon
pKa (Strongest Basic)	0.27	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	102.34 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	127.7 m³·mol⁻¹	ChemAxon
Polarizability	49.55 Å³	ChemAxon
Number of Rings	6	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

71048382

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

132550031

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Kai A, Kato H, Sherman DH, Williams RM, Tsukamoto S: Isolation of a new indoxyl alkaloid, Amoenamide B, from Aspergillus amoenus NRRL 35600: biosynthetic implications and correction of the structure of Speramide B. Tetrahedron Lett. 2018 Nov 28;50(48):4236-4240. doi: 10.1016/j.tetlet.2018.10.034. Epub 2018 Oct 20. [PubMed:30765898 ]
LOTUS database [Link]

Showing NP-Card for (1r,13s,16r,22s)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0²,¹¹.0⁵,¹⁰.0¹⁴,²².0¹⁶,²⁰]tricosa-2(11),3,5(10),8-tetraene-15,21-dione (NP0277375)

MOL for NP0277375 ((1r,13s,16r,22s)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0²,¹¹.0⁵,¹⁰.0¹⁴,²².0¹⁶,²⁰]tricosa-2(11),3,5(10),8-tetraene-15,21-dione)

3D MOL for NP0277375 ((1r,13s,16r,22s)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0²,¹¹.0⁵,¹⁰.0¹⁴,²².0¹⁶,²⁰]tricosa-2(11),3,5(10),8-tetraene-15,21-dione)

3D SDF for NP0277375 ((1r,13s,16r,22s)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0²,¹¹.0⁵,¹⁰.0¹⁴,²².0¹⁶,²⁰]tricosa-2(11),3,5(10),8-tetraene-15,21-dione)

3D-SDF for NP0277375 ((1r,13s,16r,22s)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0²,¹¹.0⁵,¹⁰.0¹⁴,²².0¹⁶,²⁰]tricosa-2(11),3,5(10),8-tetraene-15,21-dione)

PDB for NP0277375 ((1r,13s,16r,22s)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0²,¹¹.0⁵,¹⁰.0¹⁴,²².0¹⁶,²⁰]tricosa-2(11),3,5(10),8-tetraene-15,21-dione)

3D PDB for NP0277375 ((1r,13s,16r,22s)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0²,¹¹.0⁵,¹⁰.0¹⁴,²².0¹⁶,²⁰]tricosa-2(11),3,5(10),8-tetraene-15,21-dione)

SMILES for NP0277375 ((1r,13s,16r,22s)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0²,¹¹.0⁵,¹⁰.0¹⁴,²².0¹⁶,²⁰]tricosa-2(11),3,5(10),8-tetraene-15,21-dione)

INCHI for NP0277375 ((1r,13s,16r,22s)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0²,¹¹.0⁵,¹⁰.0¹⁴,²².0¹⁶,²⁰]tricosa-2(11),3,5(10),8-tetraene-15,21-dione)

Structure for NP0277375 ((1r,13s,16r,22s)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0²,¹¹.0⁵,¹⁰.0¹⁴,²².0¹⁶,²⁰]tricosa-2(11),3,5(10),8-tetraene-15,21-dione)

3D Structure for NP0277375 ((1r,13s,16r,22s)-1,16-dihydroxy-7,7-dimethyl-13-(2-methylbut-3-en-2-yl)-6-oxa-12,14,20-triazahexacyclo[11.10.0.0²,¹¹.0⁵,¹⁰.0¹⁴,²².0¹⁶,²⁰]tricosa-2(11),3,5(10),8-tetraene-15,21-dione)