NP-MRD: Showing NP-Card for (2r,4z,5r,6s)-18-hydroxy-4-(hydroxyimino)-5-methoxy-6-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),17,20(27),21(26),22,24-decaen-16-one (NP0265498)

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Record Information

Version

2.0

Created at

2022-09-08 09:30:10 UTC

Updated at

2022-09-08 09:30:11 UTC

NP-MRD ID

NP0265498

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2r,4z,5r,6s)-18-hydroxy-4-(hydroxyimino)-5-methoxy-6-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),17,20(27),21(26),22,24-decaen-16-one

Description

(9S)-10,11,12,13-Tetrahydro-10alpha-methoxy-9-methyl-11-hydroxyimino-9beta,13beta-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-Lm]pyrrolo[3,4-j][1,7]benzodiazonine-1,3(2H)-dione belongs to the class of organic compounds known as indolocarbazoles. These are polycyclic aromatic compounds containing an indole fused to a carbazole. (2r,4z,5r,6s)-18-hydroxy-4-(hydroxyimino)-5-methoxy-6-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),17,20(27),21(26),22,24-decaen-16-one is found in Streptomyces longisporoflavus. Based on a literature review very few articles have been published on (9S)-10,11,12,13-Tetrahydro-10alpha-methoxy-9-methyl-11-hydroxyimino-9beta,13beta-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-Lm]pyrrolo[3,4-j][1,7]benzodiazonine-1,3(2H)-dione.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309082211302D          

 36 43  0  0  1  0            999 V2000
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M  END

     RDKit          3D

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M  END


  Mrv1652309082211302D          

 36 43  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0265498

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CO[C@@H]1\C(C[C@H]2O[C@]1(C)N1C3=C(C=CC=C3)C3=C1C1=C(C4=CC=CC=C4N21)C1=C3C(=O)N=C1O)=N/O

> <INCHI_IDENTIFIER>
InChI=1S/C27H20N4O5/c1-27-24(35-2)14(29-34)11-17(36-27)30-15-9-5-3-7-12(15)18-20-21(26(33)28-25(20)32)19-13-8-4-6-10-16(13)31(27)23(19)22(18)30/h3-10,17,24,34H,11H2,1-2H3,(H,28,32,33)/b29-14-/t17-,24-,27+/m1/s1

> <INCHI_KEY>
QQUAZSGADPYWIJ-YYORNGEESA-N

> <FORMULA>
C27H20N4O5

> <MOLECULAR_WEIGHT>
480.48

> <EXACT_MASS>
480.14336976

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
49.25826397772864

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(2R,4Z,5R,6S)-18-hydroxy-4-(hydroxyimino)-5-methoxy-6-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1^{2,6}.0^{7,28}.0^{8,13}.0^{15,19}.0^{20,27}.0^{21,26}]nonacosa-8(13),9,11,14(28),15(19),17,20(27),21,23,25-decaen-16-one

> <JCHEM_LOGP>
4.345285290666666

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA>
9.643190237941274

> <JCHEM_PKA_STRONGEST_ACIDIC>
6.613481599855896

> <JCHEM_PKA_STRONGEST_BASIC>
-2.3006601360748467

> <JCHEM_POLAR_SURFACE_AREA>
110.57

> <JCHEM_REFRACTIVITY>
130.2163

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2R,4Z,5R,6S)-18-hydroxy-4-(hydroxyimino)-5-methoxy-6-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1^{2,6}.0^{7,28}.0^{8,13}.0^{15,19}.0^{20,27}.0^{21,26}]nonacosa-8(13),9,11,14(28),15(19),17,20(27),21,23,25-decaen-16-one

> <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       1.071   0.570   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       2.335  -0.310   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0       3.729   0.345   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.999  -0.612   0.000  0.00  0.00           C+0
HETATM    5  N   UNK     0       4.886  -2.148   0.000  0.00  0.00           N+0
HETATM    6  O   UNK     0       3.500  -2.818   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0       6.411   0.157   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.597   1.877   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       5.195   2.043   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       3.807   2.016   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.269   1.921   0.000  0.00  0.00           C+0
HETATM   12  N   UNK     0       3.518   3.691   0.000  0.00  0.00           N+0
HETATM   13  C   UNK     0       2.023   4.273   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.639   3.596   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.638   4.456   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -0.532   5.993   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       0.851   6.669   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       2.129   5.809   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.674   6.255   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.514   7.576   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       6.054   7.581   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.917   6.204   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.461   5.783   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.723   6.667   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      11.118   6.016   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      11.253   4.482   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.991   3.599   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.596   4.249   0.000  0.00  0.00           C+0
HETATM   29  N   UNK     0       7.067   3.562   0.000  0.00  0.00           N+0
HETATM   30  C   UNK     0       6.093   4.876   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       4.516   4.950   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       6.526   9.047   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       7.989   9.527   0.000  0.00  0.00           O+0
HETATM   34  N   UNK     0       5.277   9.948   0.000  0.00  0.00           N+0
HETATM   35  C   UNK     0       4.034   9.039   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       2.568   9.511   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4   10                                                  
CONECT    4    3    5    7                                                  
CONECT    5    4    6                                                       
CONECT    6    5                                                            
CONECT    7    4    8                                                       
CONECT    8    7    9   29                                                  
CONECT    9    8   10                                                       
CONECT   10    9    3   11   12                                             
CONECT   11   10                                                            
CONECT   12   10   13   31                                                  
CONECT   13   12   14   18                                                  
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   13   19                                                  
CONECT   19   18   20   31                                                  
CONECT   20   19   21   35                                                  
CONECT   21   20   22   32                                                  
CONECT   22   21   23   30                                                  
CONECT   23   22   24   28                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   23   29                                                  
CONECT   29   28    8   30                                                  
CONECT   30   29   22   31                                                  
CONECT   31   30   19   12                                                  
CONECT   32   21   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35                                                       
CONECT   35   34   20   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   86    0
END

View in JSmol

Synonyms

Value	Source
(9S)-10,11,12,13-Tetrahydro-10a-methoxy-9-methyl-11-hydroxyimino-9b,13b-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-LM]pyrrolo[3,4-J][1,7]benzodiazonine-1,3(2H)-dione	Generator
(9S)-10,11,12,13-Tetrahydro-10α-methoxy-9-methyl-11-hydroxyimino-9β,13β-epoxy-1H,9H-diindolo[1,2,3-gh:3',2',1'-LM]pyrrolo[3,4-J][1,7]benzodiazonine-1,3(2H)-dione	Generator

Chemical Formula

C₂₇H₂₀N₄O₅

Average Mass

480.4800 Da

Monoisotopic Mass

480.14337 Da

IUPAC Name

(2R,4Z,5R,6S)-18-hydroxy-4-(hydroxyimino)-5-methoxy-6-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1^{2,6}.0^{7,28}.0^{8,13}.0^{15,19}.0^{20,27}.0^{21,26}]nonacosa-8(13),9,11,14(28),15(19),17,20(27),21,23,25-decaen-16-one

Traditional Name

CAS Registry Number

Not Available

SMILES

CO[C@@H]1\C(C[C@H]2O[C@]1(C)N1C3=C(C=CC=C3)C3=C1C1=C(C4=CC=CC=C4N21)C1=C3C(=O)N=C1O)=N/O

InChI Identifier

InChI=1S/C27H20N4O5/c1-27-24(35-2)14(29-34)11-17(36-27)30-15-9-5-3-7-12(15)18-20-21(26(33)28-25(20)32)19-13-8-4-6-10-16(13)31(27)23(19)22(18)30/h3-10,17,24,34H,11H2,1-2H3,(H,28,32,33)/b29-14-/t17-,24-,27+/m1/s1

InChI Key

QQUAZSGADPYWIJ-YYORNGEESA-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
Streptomyces longisporoflavus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolocarbazoles. These are polycyclic aromatic compounds containing an indole fused to a carbazole.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Carbazoles

Direct Parent

Indolocarbazoles

Alternative Parents

Substituents

Indolocarbazole
Pyrrolo[2,3-a]carbazole
Pyrroloindole
Phthalimide
Isoindolone
Indole
Isoindoline
Isoindole or derivatives
Oxane
Benzenoid
Pyrrole
Carboxylic acid imide
Carboxylic acid imide, n-unsubstituted
Heteroaromatic compound
Oxacycle
Oxime
Azacycle
Carboxylic acid derivative
Dialkyl ether
Ether
Organooxygen compound
Organic oxygen compound
Organic nitrogen compound
Organic oxide
Hydrocarbon derivative
Organonitrogen compound
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	4.35	ChemAxon
pKa (Strongest Acidic)	6.61	ChemAxon
pKa (Strongest Basic)	-2.3	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	110.57 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	130.22 m³·mol⁻¹	ChemAxon
Polarizability	49.26 Å³	ChemAxon
Number of Rings	8	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

8989879

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10814574

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (2r,4z,5r,6s)-18-hydroxy-4-(hydroxyimino)-5-methoxy-6-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),17,20(27),21(26),22,24-decaen-16-one (NP0265498)

MOL for NP0265498 ((2r,4z,5r,6s)-18-hydroxy-4-(hydroxyimino)-5-methoxy-6-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),17,20(27),21(26),22,24-decaen-16-one)

3D MOL for NP0265498 ((2r,4z,5r,6s)-18-hydroxy-4-(hydroxyimino)-5-methoxy-6-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),17,20(27),21(26),22,24-decaen-16-one)

3D SDF for NP0265498 ((2r,4z,5r,6s)-18-hydroxy-4-(hydroxyimino)-5-methoxy-6-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),17,20(27),21(26),22,24-decaen-16-one)

3D-SDF for NP0265498 ((2r,4z,5r,6s)-18-hydroxy-4-(hydroxyimino)-5-methoxy-6-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),17,20(27),21(26),22,24-decaen-16-one)

PDB for NP0265498 ((2r,4z,5r,6s)-18-hydroxy-4-(hydroxyimino)-5-methoxy-6-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),17,20(27),21(26),22,24-decaen-16-one)

3D PDB for NP0265498 ((2r,4z,5r,6s)-18-hydroxy-4-(hydroxyimino)-5-methoxy-6-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),17,20(27),21(26),22,24-decaen-16-one)

SMILES for NP0265498 ((2r,4z,5r,6s)-18-hydroxy-4-(hydroxyimino)-5-methoxy-6-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),17,20(27),21(26),22,24-decaen-16-one)

INCHI for NP0265498 ((2r,4z,5r,6s)-18-hydroxy-4-(hydroxyimino)-5-methoxy-6-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),17,20(27),21(26),22,24-decaen-16-one)

Structure for NP0265498 ((2r,4z,5r,6s)-18-hydroxy-4-(hydroxyimino)-5-methoxy-6-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),17,20(27),21(26),22,24-decaen-16-one)

3D Structure for NP0265498 ((2r,4z,5r,6s)-18-hydroxy-4-(hydroxyimino)-5-methoxy-6-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8(13),9,11,14(28),15(19),17,20(27),21(26),22,24-decaen-16-one)