NP-MRD: Showing NP-Card for (1's,2s,2'r,12's,14's,17's,19'r,21'r)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosane]-4',9'-diene-3',8',15',20'-tetrone (NP0174930)

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Record Information

Version

2.0

Created at

2022-09-03 12:17:02 UTC

Updated at

2022-09-03 12:17:03 UTC

NP-MRD ID

NP0174930

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1's,2s,2'r,12's,14's,17's,19'r,21'r)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosane]-4',9'-diene-3',8',15',20'-tetrone

Description

(1'S,2S,2'R,12'S,14'S,17'S,19'R,21'R)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]Henicosane]-4',9'-diene-3',8',15',20'-tetrone belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds. (1's,2s,2'r,12's,14's,17's,19'r,21'r)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosane]-4',9'-diene-3',8',15',20'-tetrone is found in Talaromyces ruber. Based on a literature review very few articles have been published on (1'S,2S,2'R,12'S,14'S,17'S,19'R,21'R)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]Henicosane]-4',9'-diene-3',8',15',20'-tetrone.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309032214172D          

 32 37  0  0  1  0            999 V2000
    0.1735   -2.3939    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4701   -1.6240    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0483   -0.9822    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.2484   -0.2124    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.1252    0.5232    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4589    1.1058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3308    1.9208    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.1935    0.7303    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.2377    1.5541    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9640    1.0250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6045    0.5050    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.3226    0.9112    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.8638    1.5969    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6870    1.6514    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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  8 32  1  0  0  0  0
M  END

     RDKit          3D

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 32 58  1  1
M  END


  Mrv1652309032214172D          

 32 37  0  0  1  0            999 V2000
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M  END
> <DATABASE_ID>
NP0174930

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@H]1O[C@H]2OC(=O)[C@@]3(C)C[C@@H]4[C@@]5(CO5)C5=CC(=O)OC(C)(C)C5=CC(=O)[C@@]4(C)[C@H]([C@@H]23)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C24H26O8/c1-10-18(27)16-17-19(30-10)31-20(28)22(17,4)8-13-23(16,5)14(25)6-11-12(24(13)9-29-24)7-15(26)32-21(11,2)3/h6-7,10,13,16-17,19H,8-9H2,1-5H3/t10-,13+,16-,17+,19+,22+,23+,24-/m1/s1

> <INCHI_KEY>
PCBBMDQLBUYDDZ-OLKDSNBSSA-N

> <FORMULA>
C24H26O8

> <MOLECULAR_WEIGHT>
442.464

> <EXACT_MASS>
442.162767797

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
58

> <JCHEM_AVERAGE_POLARIZABILITY>
43.77805391456674

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1'S,2S,2'R,12'S,14'S,17'S,19'R,21'R)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0^{2,12}.0^{5,10}.0^{17,21}]henicosane]-4',9'-diene-3',8',15',20'-tetrone

> <ALOGPS_LOGP>
2.31

> <JCHEM_LOGP>
2.2661276673333344

> <ALOGPS_LOGS>
-3.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.462121844859567

> <JCHEM_PKA_STRONGEST_BASIC>
-4.00739828214426

> <JCHEM_POLAR_SURFACE_AREA>
108.5

> <JCHEM_REFRACTIVITY>
109.55019999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.42e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1'S,2S,2'R,12'S,14'S,17'S,19'R,21'R)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0^{2,12}.0^{5,10}.0^{17,21}]henicosane]-4',9'-diene-3',8',15',20'-tetrone

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 03-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   03-SEP-22         0                                  
HETATM    1  C   UNK     0       0.324  -4.469   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.878  -3.032   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -0.090  -1.833   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.464  -0.396   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -0.234   0.977   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.857   2.064   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       0.618   3.585   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.228   1.363   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.310   2.901   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.666   1.913   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.862   0.943   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.202   1.701   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.346   2.981   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       6.882   3.083   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       7.631   1.126   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       8.688   2.245   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      10.186   1.890   0.000  0.00  0.00           C+0
HETATM   18  O   UNK     0      11.244   3.009   0.000  0.00  0.00           O+0
HETATM   19  O   UNK     0      10.627   0.414   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0       9.570  -0.705   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.856  -1.552   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       8.959  -2.119   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.072  -0.350   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       7.193  -1.614   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.656  -1.716   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0       5.081  -3.145   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0       4.619  -0.578   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0       4.317  -2.088   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.953  -1.356   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       2.399  -2.793   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       3.367  -3.991   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       1.985  -0.157   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   30                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   32                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   10   32                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   27                                                  
CONECT   12   11   13   14   15                                             
CONECT   13   12   14                                                       
CONECT   14   13   12                                                       
CONECT   15   12   16   23                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18   19                                                  
CONECT   18   17                                                            
CONECT   19   17   20                                                       
CONECT   20   19   21   22   23                                             
CONECT   21   20                                                            
CONECT   22   20                                                            
CONECT   23   20   15   24                                                  
CONECT   24   23   25                                                       
CONECT   25   24   26   27                                                  
CONECT   26   25                                                            
CONECT   27   25   11   28   29                                             
CONECT   28   27                                                            
CONECT   29   27   30   32                                                  
CONECT   30   29    2   31                                                  
CONECT   31   30                                                            
CONECT   32   29    4    8                                                  
MASTER        0    0    0    0    0    0    0    0   32    0   74    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₄H₂₆O₈

Average Mass

442.4640 Da

Monoisotopic Mass

442.16277 Da

IUPAC Name

(1'S,2S,2'R,12'S,14'S,17'S,19'R,21'R)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0^{2,12}.0^{5,10}.0^{17,21}]henicosane]-4',9'-diene-3',8',15',20'-tetrone

Traditional Name

(1'S,2S,2'R,12'S,14'S,17'S,19'R,21'R)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0^{2,12}.0^{5,10}.0^{17,21}]henicosane]-4',9'-diene-3',8',15',20'-tetrone

CAS Registry Number

Not Available

SMILES

C[C@H]1O[C@H]2OC(=O)[C@@]3(C)C[C@@H]4[C@@]5(CO5)C5=CC(=O)OC(C)(C)C5=CC(=O)[C@@]4(C)[C@H]([C@@H]23)C1=O

InChI Identifier

InChI=1S/C24H26O8/c1-10-18(27)16-17-19(30-10)31-20(28)22(17,4)8-13-23(16,5)14(25)6-11-12(24(13)9-29-24)7-15(26)32-21(11,2)3/h6-7,10,13,16-17,19H,8-9H2,1-5H3/t10-,13+,16-,17+,19+,22+,23+,24-/m1/s1

InChI Key

PCBBMDQLBUYDDZ-OLKDSNBSSA-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
Talaromyces ruber	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as furopyrans. These are organic polycyclic compounds containing a furan ring fused to a pyran ring. Furan is a five-membered aromatic ring with four carbon atoms and one oxygen atom. Pyran a six-membered heterocyclic, non-aromatic ring, made up of five carbon atoms and one oxygen atom and containing two double bonds.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Furopyrans

Sub Class

Not Available

Direct Parent

Furopyrans

Alternative Parents

Substituents

Furopyran
Dihydropyranone
Dicarboxylic acid or derivatives
Gamma butyrolactone
Oxane
Pyran
Alpha,beta-unsaturated carboxylic ester
Oxolane
Enoate ester
Furan
Carboxylic acid ester
Ketone
Lactone
Ether
Oxirane
Acetal
Dialkyl ether
Carboxylic acid derivative
Oxacycle
Organic oxide
Organooxygen compound
Organic oxygen compound
Hydrocarbon derivative
Aldehyde
Carbonyl group
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic 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	2.31	ALOGPS
logP	2.27	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.46	ChemAxon
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	108.5 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	109.55 m³·mol⁻¹	ChemAxon
Polarizability	43.78 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

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

100853850

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1's,2s,2'r,12's,14's,17's,19'r,21'r)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosane]-4',9'-diene-3',8',15',20'-tetrone (NP0174930)

MOL for NP0174930 ((1's,2s,2'r,12's,14's,17's,19'r,21'r)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosane]-4',9'-diene-3',8',15',20'-tetrone)

3D MOL for NP0174930 ((1's,2s,2'r,12's,14's,17's,19'r,21'r)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosane]-4',9'-diene-3',8',15',20'-tetrone)

3D SDF for NP0174930 ((1's,2s,2'r,12's,14's,17's,19'r,21'r)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosane]-4',9'-diene-3',8',15',20'-tetrone)

3D-SDF for NP0174930 ((1's,2s,2'r,12's,14's,17's,19'r,21'r)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosane]-4',9'-diene-3',8',15',20'-tetrone)

PDB for NP0174930 ((1's,2s,2'r,12's,14's,17's,19'r,21'r)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosane]-4',9'-diene-3',8',15',20'-tetrone)

3D PDB for NP0174930 ((1's,2s,2'r,12's,14's,17's,19'r,21'r)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosane]-4',9'-diene-3',8',15',20'-tetrone)

SMILES for NP0174930 ((1's,2s,2'r,12's,14's,17's,19'r,21'r)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosane]-4',9'-diene-3',8',15',20'-tetrone)

INCHI for NP0174930 ((1's,2s,2'r,12's,14's,17's,19'r,21'r)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosane]-4',9'-diene-3',8',15',20'-tetrone)

Structure for NP0174930 ((1's,2s,2'r,12's,14's,17's,19'r,21'r)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosane]-4',9'-diene-3',8',15',20'-tetrone)

3D Structure for NP0174930 ((1's,2s,2'r,12's,14's,17's,19'r,21'r)-2',6',6',14',19'-pentamethyl-7',16',18'-trioxaspiro[oxirane-2,11'-pentacyclo[12.6.1.0²,¹².0⁵,¹⁰.0¹⁷,²¹]henicosane]-4',9'-diene-3',8',15',20'-tetrone)