NP-MRD: Showing NP-Card for 4-amino-11,12,18-trihydroxy-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 (NP0187399)

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Record Information

Version

2.0

Created at

2022-09-04 03:34:05 UTC

Updated at

2022-09-04 03:34:05 UTC

NP-MRD ID

NP0187399

Secondary Accession Numbers

None

Natural Product Identification

Common Name

4-amino-11,12,18-trihydroxy-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

4-Amino-11,12,18-trihydroxy-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),9,11,14,17,19,21,23,25,27-decaen-16-one belongs to the class of organic compounds known as indolocarbazoles. These are polycyclic aromatic compounds containing an indole fused to a carbazole. 4-Amino-11,12,18-trihydroxy-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),9,11,14,17,19,21,23,25,27-decaen-16-one is a very strong basic compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004171521042D          

 37 44  0  0  0  0            999 V2000
    1.1814   -0.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    3.5340    1.0056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    1.0837    2.2891    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


  Mrv1533004171521042D          

 37 44  0  0  0  0            999 V2000
    1.1814   -0.9881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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 29 34  1  0  0  0  0
 34 35  1  0  0  0  0
  7 35  1  0  0  0  0
 35 36  1  0  0  0  0
 28 36  2  0  0  0  0
 36 37  1  0  0  0  0
 11 37  1  0  0  0  0
 20 37  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0187399

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC1C(N)CC2OC1(C)N1C3=C(C4=C1C1=C(C5=CC=CC=C5N21)C1=C4C(=O)NC1=O)C(O)=C(O)C=C3

> <INCHI_IDENTIFIER>
InChI=1S/C27H22N4O6/c1-27-24(36-2)11(28)9-15(37-27)30-12-6-4-3-5-10(12)16-19-20(26(35)29-25(19)34)18-17-13(7-8-14(32)23(17)33)31(27)22(18)21(16)30/h3-8,11,15,24,32-33H,9,28H2,1-2H3,(H,29,34,35)

> <INCHI_KEY>
MPFXTYXHOXVKPU-UHFFFAOYSA-N

> <FORMULA>
C27H22N4O6

> <MOLECULAR_WEIGHT>
498.495

> <EXACT_MASS>
498.153934444

> <JCHEM_ACCEPTOR_COUNT>
7

> <JCHEM_ATOM_COUNT>
59

> <JCHEM_AVERAGE_POLARIZABILITY>
51.218341382079714

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
4-amino-22,23-dihydroxy-3-methoxy-2-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8,10,12,14(28),15(19),20(27),21(26),22,24-nonaene-16,18-dione

> <ALOGPS_LOGP>
2.46

> <JCHEM_LOGP>
1.6579360089044652

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
8

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
8.320561496877128

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.564476224619309

> <JCHEM_PKA_STRONGEST_BASIC>
9.632477868720617

> <JCHEM_POLAR_SURFACE_AREA>
140.97

> <JCHEM_REFRACTIVITY>
132.28639999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.41e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-amino-22,23-dihydroxy-3-methoxy-2-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8,10,12,14(28),15(19),20(27),21(26),22,24-nonaene-16,18-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 17-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-APR-15         0                                  
HETATM    1  C   UNK     0       2.205  -1.844   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  C   UNK     0       6.411   0.157   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.597   1.877   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       5.195   2.043   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       3.807   2.016   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.269   1.921   0.000  0.00  0.00           C+0
HETATM   11  N   UNK     0       3.518   3.691   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0       2.023   4.273   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.639   3.596   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.638   4.456   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.532   5.993   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.810   6.853   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       0.851   6.669   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       0.957   8.206   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       2.129   5.809   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       3.674   6.255   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       4.514   7.576   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       4.034   9.039   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0       2.568   9.511   0.000  0.00  0.00           O+0
HETATM   24  N   UNK     0       5.277   9.948   0.000  0.00  0.00           N+0
HETATM   25  C   UNK     0       6.526   9.047   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       7.989   9.527   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       6.054   7.581   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       6.917   6.204   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       8.461   5.783   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       9.723   6.667   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      11.118   6.016   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.253   4.482   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       9.991   3.599   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0       8.596   4.249   0.000  0.00  0.00           C+0
HETATM   35  N   UNK     0       7.067   3.562   0.000  0.00  0.00           N+0
HETATM   36  C   UNK     0       6.093   4.876   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.516   4.950   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    9                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8   35                                                  
CONECT    8    7    9                                                       
CONECT    9    8    3   10   11                                             
CONECT   10    9                                                            
CONECT   11    9   12   37                                                  
CONECT   12   11   13   19                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   12   20                                                  
CONECT   20   19   21   37                                                  
CONECT   21   20   22   27                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   21   28                                                  
CONECT   28   27   29   36                                                  
CONECT   29   28   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   29   35                                                  
CONECT   35   34    7   36                                                  
CONECT   36   35   28   37                                                  
CONECT   37   36   11   20                                                  
MASTER        0    0    0    0    0    0    0    0   37    0   88    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₇H₂₂N₄O₆

Average Mass

498.4950 Da

Monoisotopic Mass

498.15393 Da

IUPAC Name

4-amino-22,23-dihydroxy-3-methoxy-2-methyl-29-oxa-1,7,17-triazaoctacyclo[12.12.2.1²,⁶.0⁷,²⁸.0⁸,¹³.0¹⁵,¹⁹.0²⁰,²⁷.0²¹,²⁶]nonacosa-8,10,12,14(28),15(19),20(27),21(26),22,24-nonaene-16,18-dione

Traditional Name

CAS Registry Number

Not Available

SMILES

COC1C(N)CC2OC1(C)N1C3=C(C4=C1C1=C(C5=CC=CC=C5N21)C1=C4C(=O)NC1=O)C(O)=C(O)C=C3

InChI Identifier

InChI=1S/C27H22N4O6/c1-27-24(36-2)11(28)9-15(37-27)30-12-6-4-3-5-10(12)16-19-20(26(35)29-25(19)34)18-17-13(7-8-14(32)23(17)33)31(27)22(18)21(16)30/h3-8,11,15,24,32-33H,9,28H2,1-2H3,(H,29,34,35)

InChI Key

MPFXTYXHOXVKPU-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 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
Hydroxyindole
Isoindolone
Indole
Isoindole
Isoindole or derivatives
1-hydroxy-4-unsubstituted benzenoid
1-hydroxy-2-unsubstituted benzenoid
Phenol
Oxane
Benzenoid
Heteroaromatic compound
Pyrrole
Amino acid or derivatives
Propargyl-type 1,3-dipolar organic compound
Polyol
Azacycle
Oxacycle
Organic 1,3-dipolar compound
Carboxylic acid derivative
Dialkyl ether
Ether
Primary amine
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Organic nitrogen compound
Amine
Primary aliphatic amine
Organonitrogen compound
Organooxygen 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	2.46	ALOGPS
logP	1.66	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	7.56	ChemAxon
pKa (Strongest Basic)	9.63	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	7	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	140.97 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	132.29 m³·mol⁻¹	ChemAxon
Polarizability	51.22 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

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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 4-amino-11,12,18-trihydroxy-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 (NP0187399)

MOL for NP0187399 (4-amino-11,12,18-trihydroxy-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 NP0187399 (4-amino-11,12,18-trihydroxy-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 NP0187399 (4-amino-11,12,18-trihydroxy-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 NP0187399 (4-amino-11,12,18-trihydroxy-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 NP0187399 (4-amino-11,12,18-trihydroxy-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 NP0187399 (4-amino-11,12,18-trihydroxy-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 NP0187399 (4-amino-11,12,18-trihydroxy-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 NP0187399 (4-amino-11,12,18-trihydroxy-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 NP0187399 (4-amino-11,12,18-trihydroxy-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 NP0187399 (4-amino-11,12,18-trihydroxy-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)