NP-MRD: Showing NP-Card for 3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1⁴,⁸.0¹,¹⁵.0²,¹³.0²²,²⁶.0¹²,²⁷]heptacosa-2(13),3,8(27),9,11,18(26),19,21-octaene-7,17,23-trione (NP0214243)

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Record Information

Version

2.0

Created at

2022-09-05 13:29:12 UTC

Updated at

2022-09-05 13:29:12 UTC

NP-MRD ID

NP0214243

Secondary Accession Numbers

None

Natural Product Identification

Common Name

3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1⁴,⁸.0¹,¹⁵.0²,¹³.0²²,²⁶.0¹²,²⁷]heptacosa-2(13),3,8(27),9,11,18(26),19,21-octaene-7,17,23-trione

Description

Bacillosporin C belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four carbon and one oxygen atoms. Naphthalene is a polycyclic aromatic hydrocarbon made up of two fused benzene rings. 3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1⁴,⁸.0¹,¹⁵.0²,¹³.0²²,²⁶.0¹²,²⁷]heptacosa-2(13),3,8(27),9,11,18(26),19,21-octaene-7,17,23-trione is found in Aegiceras corniculatum and Talaromyces bacillisporus. 3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1⁴,⁸.0¹,¹⁵.0²,¹³.0²²,²⁶.0¹²,²⁷]heptacosa-2(13),3,8(27),9,11,18(26),19,21-octaene-7,17,23-trione was first documented in 2007 (PMID: 17372959). Based on a literature review very few articles have been published on Bacillosporin C (PMID: 18067932).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309052215292D          

 36 42  0  0  0  0            999 V2000
   -1.1911    0.3168    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5956   -0.2541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7922   -1.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1966   -1.6262    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3933   -2.4274    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5956   -1.3959    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7922   -0.5947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1966   -0.0238    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3933    0.7774    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2023    1.3484    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1855    1.0078    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


  Mrv1652309052215292D          

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M  END
> <DATABASE_ID>
NP0214243

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(O)=C2C(=O)OCC3=C2C1=C1OC2(O)CC(=O)C4=C5C(C(=O)OCC25C1=C3O)=C(O)C=C4C

> <INCHI_IDENTIFIER>
InChI=1S/C26H18O10/c1-8-3-12(28)18-19-14(8)13(29)5-26(33)25(19,7-35-24(18)32)20-21(30)10-6-34-23(31)17-11(27)4-9(2)15(16(10)17)22(20)36-26/h3-4,27-28,30,33H,5-7H2,1-2H3

> <INCHI_KEY>
KHBPWHLZTSXJPH-UHFFFAOYSA-N

> <FORMULA>
C26H18O10

> <MOLECULAR_WEIGHT>
490.42

> <EXACT_MASS>
490.08999678

> <JCHEM_ACCEPTOR_COUNT>
8

> <JCHEM_ATOM_COUNT>
54

> <JCHEM_AVERAGE_POLARIZABILITY>
46.745950929275025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
4

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1^{4,8}.0^{1,15}.0^{2,13}.0^{22,26}.0^{12,27}]heptacosa-2,4(27),8,10,12,18(26),19,21-octaene-7,17,23-trione

> <JCHEM_LOGP>
4.099923723333333

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
8.489645504378709

> <JCHEM_PKA_STRONGEST_ACIDIC>
7.848743041464785

> <JCHEM_PKA_STRONGEST_BASIC>
-4.312121670381235

> <JCHEM_POLAR_SURFACE_AREA>
159.82

> <JCHEM_REFRACTIVITY>
133.56439999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1^{4,8}.0^{1,15}.0^{2,13}.0^{22,26}.0^{12,27}]heptacosa-2,4(27),8,10,12,18(26),19,21-octaene-7,17,23-trione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 05-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-SEP-22         0                                  
HETATM    1  C   UNK     0      -2.223   0.591   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.112  -0.474   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.479  -1.970   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.367  -3.036   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.734  -4.531   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       1.112  -2.606   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.479  -1.110   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.367  -0.044   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.734   1.451   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.378   2.517   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       2.213   1.881   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.325   0.815   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       3.846   2.265   0.000  0.00  0.00           O+0
HETATM   14  O   UNK     0       4.860   0.929   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       5.443  -0.497   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.453  -1.379   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       4.540  -3.007   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0       3.363  -4.001   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       5.989  -3.528   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       7.165  -2.534   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.614  -3.056   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.790  -2.061   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      11.239  -2.583   0.000  0.00  0.00           O+0
HETATM   24  C   UNK     0       9.517  -0.546   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       8.068  -0.024   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       7.795   1.491   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       6.892  -1.019   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       8.887  -4.571   0.000  0.00  0.00           C+0
HETATM   29  O   UNK     0      10.336  -5.093   0.000  0.00  0.00           O+0
HETATM   30  O   UNK     0       7.711  -5.565   0.000  0.00  0.00           O+0
HETATM   31  C   UNK     0       6.262  -5.044   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0       2.958  -0.680   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0       4.069  -1.746   0.000  0.00  0.00           C+0
HETATM   34  O   UNK     0       3.702  -3.241   0.000  0.00  0.00           O+0
HETATM   35  C   UNK     0       2.223  -3.671   0.000  0.00  0.00           C+0
HETATM   36  O   UNK     0       1.856  -5.167   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    8                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7   35                                                  
CONECT    7    6    8   32                                                  
CONECT    8    7    2    9                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13   14   32                                             
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16   27                                                  
CONECT   16   15   17   32                                                  
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20   31                                                  
CONECT   20   19   21   27                                                  
CONECT   21   20   22   28                                                  
CONECT   22   21   23   24                                                  
CONECT   23   22                                                            
CONECT   24   22   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   15   20                                                  
CONECT   28   21   29   30                                                  
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   19                                                       
CONECT   32   16    7   12   33                                             
CONECT   33   32   34                                                       
CONECT   34   33   35                                                       
CONECT   35   34    6   36                                                  
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   84    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₆H₁₈O₁₀

Average Mass

490.4200 Da

Monoisotopic Mass

490.09000 Da

IUPAC Name

3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1^{4,8}.0^{1,15}.0^{2,13}.0^{22,26}.0^{12,27}]heptacosa-2,4(27),8,10,12,18(26),19,21-octaene-7,17,23-trione

Traditional Name

3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1^{4,8}.0^{1,15}.0^{2,13}.0^{22,26}.0^{12,27}]heptacosa-2,4(27),8,10,12,18(26),19,21-octaene-7,17,23-trione

CAS Registry Number

Not Available

SMILES

CC1=CC(O)=C2C(=O)OCC3=C2C1=C1OC2(O)CC(=O)C4=C5C(C(=O)OCC25C1=C3O)=C(O)C=C4C

InChI Identifier

InChI=1S/C26H18O10/c1-8-3-12(28)18-19-14(8)13(29)5-26(33)25(19,7-35-24(18)32)20-21(30)10-6-34-23(31)17-11(27)4-9(2)15(16(10)17)22(20)36-26/h3-4,27-28,30,33H,5-7H2,1-2H3

InChI Key

KHBPWHLZTSXJPH-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

Species Name	Source	Reference
Aegiceras corniculatum	LOTUS Database	35616633
Talaromyces bacillisporus	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as naphthofurans. Naphthofurans are compounds containing a furan ring fused to a naphthalene moiety. Furan is a 5 membered- ring aromatic ring with four 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

Naphthofurans

Sub Class

Not Available

Direct Parent

Naphthofurans

Alternative Parents

Substituents

Naphthofuran
2-naphthol
Benzopyran
Isochromane
Naphthalene
2-benzopyran
Tetralin
Coumaran
Aryl alkyl ketone
Aryl ketone
1-hydroxy-2-unsubstituted benzenoid
Phenol
Benzenoid
Vinylogous acid
Carboxylic acid ester
Hemiacetal
Ketone
Lactone
Carboxylic acid derivative
Oxacycle
Polyol
Organic oxide
Organic oxygen compound
Hydrocarbon derivative
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	4.1	ChemAxon
pKa (Strongest Acidic)	7.85	ChemAxon
pKa (Strongest Basic)	-4.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	8	ChemAxon
Hydrogen Donor Count	4	ChemAxon
Polar Surface Area	159.82 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	133.56 m³·mol⁻¹	ChemAxon
Polarizability	46.75 Å³	ChemAxon
Number of Rings	7	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

27025822

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

101285899

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Lin Z, Zhu T, Fang Y, Gu Q, Zhu W: Polyketides from Penicillium sp. JP-1, an endophytic fungus associated with the mangrove plant Aegiceras corniculatum. Phytochemistry. 2008 Mar;69(5):1273-8. doi: 10.1016/j.phytochem.2007.10.030. Epub 2007 Dec 11. [PubMed:18067932 ]
Guo Z, Shao C, She Z, Cai X, Liu F, Vrijimoed LL, Lin Y: 1H and 13C NMR assignments for two oxaphenalenones bacillosporin C and D from the mangrove endophytic fungus SBE-14. Magn Reson Chem. 2007 May;45(5):439-41. doi: 10.1002/mrc.1976. [PubMed:17372959 ]
LOTUS database [Link]

Showing NP-Card for 3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1⁴,⁸.0¹,¹⁵.0²,¹³.0²²,²⁶.0¹²,²⁷]heptacosa-2(13),3,8(27),9,11,18(26),19,21-octaene-7,17,23-trione (NP0214243)

MOL for NP0214243 (3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1⁴,⁸.0¹,¹⁵.0²,¹³.0²²,²⁶.0¹²,²⁷]heptacosa-2(13),3,8(27),9,11,18(26),19,21-octaene-7,17,23-trione)

3D MOL for NP0214243 (3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1⁴,⁸.0¹,¹⁵.0²,¹³.0²²,²⁶.0¹²,²⁷]heptacosa-2(13),3,8(27),9,11,18(26),19,21-octaene-7,17,23-trione)

3D SDF for NP0214243 (3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1⁴,⁸.0¹,¹⁵.0²,¹³.0²²,²⁶.0¹²,²⁷]heptacosa-2(13),3,8(27),9,11,18(26),19,21-octaene-7,17,23-trione)

3D-SDF for NP0214243 (3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1⁴,⁸.0¹,¹⁵.0²,¹³.0²²,²⁶.0¹²,²⁷]heptacosa-2(13),3,8(27),9,11,18(26),19,21-octaene-7,17,23-trione)

PDB for NP0214243 (3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1⁴,⁸.0¹,¹⁵.0²,¹³.0²²,²⁶.0¹²,²⁷]heptacosa-2(13),3,8(27),9,11,18(26),19,21-octaene-7,17,23-trione)

3D PDB for NP0214243 (3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1⁴,⁸.0¹,¹⁵.0²,¹³.0²²,²⁶.0¹²,²⁷]heptacosa-2(13),3,8(27),9,11,18(26),19,21-octaene-7,17,23-trione)

SMILES for NP0214243 (3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1⁴,⁸.0¹,¹⁵.0²,¹³.0²²,²⁶.0¹²,²⁷]heptacosa-2(13),3,8(27),9,11,18(26),19,21-octaene-7,17,23-trione)

INCHI for NP0214243 (3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1⁴,⁸.0¹,¹⁵.0²,¹³.0²²,²⁶.0¹²,²⁷]heptacosa-2(13),3,8(27),9,11,18(26),19,21-octaene-7,17,23-trione)

Structure for NP0214243 (3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1⁴,⁸.0¹,¹⁵.0²,¹³.0²²,²⁶.0¹²,²⁷]heptacosa-2(13),3,8(27),9,11,18(26),19,21-octaene-7,17,23-trione)

3D Structure for NP0214243 (3,9,15,21-tetrahydroxy-11,19-dimethyl-6,14,24-trioxaheptacyclo[16.7.1.1⁴,⁸.0¹,¹⁵.0²,¹³.0²²,²⁶.0¹²,²⁷]heptacosa-2(13),3,8(27),9,11,18(26),19,21-octaene-7,17,23-trione)