NP-MRD: Showing NP-Card for 5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0¹,³.0⁶,¹⁰]tetradeca-6,12-diene-8,14-dione (NP0159923)

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Record Information

Version

2.0

Created at

2022-09-02 17:45:21 UTC

Updated at

2022-09-02 17:45:21 UTC

NP-MRD ID

NP0159923

Secondary Accession Numbers

None

Natural Product Identification

Common Name

5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0¹,³.0⁶,¹⁰]tetradeca-6,12-diene-8,14-dione

Description

Guillonein belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative. 5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0¹,³.0⁶,¹⁰]tetradeca-6,12-diene-8,14-dione is found in Thapsia scabra. Based on a literature review very few articles have been published on Guillonein.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 39  0  0  0  0  0  0  0  0999 V2000
   -1.7841    3.3929    0.1741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7080    1.9292   -0.1712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1797    1.4066   -1.2985 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9499   -0.0233   -1.3225 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1480   -0.7864   -2.2774 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4414   -0.3784   -0.0019 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.4032   -1.1639    0.8259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1353   -1.6130    0.4512 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1817   -2.8343   -0.4292 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0652   -1.6984    1.5286 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2541   -1.4044    0.8566 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3542   -1.7058    1.6203 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2171    0.0308    0.4204 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0842    0.4267   -0.4852 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1417   -0.4237   -1.1534 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8477    1.8404   -0.7414 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5258    2.5205   -1.5719 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8042    2.2432    0.0575 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3791    1.1477    0.8071 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0984    0.8913    0.6989 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.5997    3.8595   -0.3850 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8411    3.9023   -0.1141 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0082    3.5196    1.2604 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6662    1.9957   -2.0774 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2220   -3.7392    0.2309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2770   -2.9446   -1.0558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0928   -2.7791   -1.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2709   -0.9666    2.3151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0683   -2.7043    2.0042 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3032   -2.0031   -0.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8375   -2.5336    1.3079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8959    0.2601   -1.5704 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6726   -1.0491   -0.3862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7178   -1.0183   -1.9725 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6454    1.3941    1.8813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5396    1.0085    1.7071 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  1
  7  8  1  0
  8  9  1  6
  8 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 14 15  1  0
 14 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20  2  1  0
  8  6  1  0
 19 13  1  0
 20  6  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  6
 12 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 19 35  1  1
 20 36  1  1
M  END


  Mrv1652309022219452D          

 20 23  0  0  0  0            999 V2000
    1.7887   -2.4909    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1756   -1.9388    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3687   -2.1103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0438   -1.3958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8643   -1.3095    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5083   -0.7827    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2870   -0.5632    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3008    0.0158    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3205    0.5586    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7957    0.6758    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6203    0.7005    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9559    1.4541    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1537    0.0711    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9728    0.1695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3746    0.8901    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3195   -0.5791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1290   -0.7385    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.7147   -1.1402    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.9942   -0.7383    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2619   -1.1183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  6  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 16 18  1  0  0  0  0
 18 19  1  0  0  0  0
 13 19  1  0  0  0  0
 19 20  1  0  0  0  0
  2 20  1  0  0  0  0
  6 20  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0159923

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC1=CC(=O)C23OC2(C)CC(O)C2=C(C)C(=O)OC2C13

> <INCHI_IDENTIFIER>
InChI=1S/C15H16O5/c1-6-4-9(17)15-11(6)12-10(7(2)13(18)19-12)8(16)5-14(15,3)20-15/h4,8,11-12,16H,5H2,1-3H3

> <INCHI_KEY>
RDCQKTDFVBOKPF-UHFFFAOYSA-N

> <FORMULA>
C15H16O5

> <MOLECULAR_WEIGHT>
276.288

> <EXACT_MASS>
276.099773615

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
27.708346992302836

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0^{1,3}.0^{6,10}]tetradeca-6,12-diene-8,14-dione

> <ALOGPS_LOGP>
0.58

> <JCHEM_LOGP>
0.6928008043333344

> <ALOGPS_LOGS>
-1.70

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.674136437280385

> <JCHEM_PKA_STRONGEST_ACIDIC>
10.707308603850995

> <JCHEM_PKA_STRONGEST_BASIC>
-3.075849017434229

> <JCHEM_POLAR_SURFACE_AREA>
76.13000000000001

> <JCHEM_REFRACTIVITY>
69.5074

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.50e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0^{1,3}.0^{6,10}]tetradeca-6,12-diene-8,14-dione

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 02-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-SEP-22         0                                  
HETATM    1  C   UNK     0       3.339  -4.650   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.195  -3.619   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.688  -3.939   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.082  -2.605   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -1.613  -2.444   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0       0.949  -1.461   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.536  -1.051   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.561   0.029   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.598   1.043   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.485   1.262   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.025   1.308   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.651   2.714   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0       4.020   0.133   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.549   0.316   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       6.299   1.661   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       6.196  -1.081   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       7.707  -1.379   0.000  0.00  0.00           O+0
HETATM   18  O   UNK     0       5.068  -2.128   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0       3.723  -1.378   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       2.356  -2.088   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   20                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7    8   20                                             
CONECT    7    6    8                                                       
CONECT    8    7    6    9   10                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11   14   19                                                  
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17   18                                                  
CONECT   17   16                                                            
CONECT   18   16   19                                                       
CONECT   19   18   13   20                                                  
CONECT   20   19    2    6                                                  
MASTER        0    0    0    0    0    0    0    0   20    0   46    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₁₆O₅

Average Mass

276.2880 Da

Monoisotopic Mass

276.09977 Da

IUPAC Name

5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0^{1,3}.0^{6,10}]tetradeca-6,12-diene-8,14-dione

Traditional Name

5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0^{1,3}.0^{6,10}]tetradeca-6,12-diene-8,14-dione

CAS Registry Number

Not Available

SMILES

CC1=CC(=O)C23OC2(C)CC(O)C2=C(C)C(=O)OC2C13

InChI Identifier

InChI=1S/C15H16O5/c1-6-4-9(17)15-11(6)12-10(7(2)13(18)19-12)8(16)5-14(15,3)20-15/h4,8,11-12,16H,5H2,1-3H3

InChI Key

RDCQKTDFVBOKPF-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
Guillonea scabra	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianolides and derivatives. These are diterpene lactones with a structure characterized by the presence of a gamma-lactone fused to a guaiane, forming 3,6,9-trimethyl-azuleno[4,5-b]furan-2-one or a derivative.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Terpene lactones

Direct Parent

Guaianolides and derivatives

Alternative Parents

Substituents

Guaianolide-skeleton
Sesquiterpenoid
2-furanone
Cyclic alcohol
Dihydrofuran
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Carboxylic acid ester
Secondary alcohol
Ketone
Lactone
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Dialkyl ether
Oxirane
Ether
Monocarboxylic acid or derivatives
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Alcohol
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	0.58	ALOGPS
logP	0.69	ChemAxon
logS	-1.7	ALOGPS
pKa (Strongest Acidic)	10.71	ChemAxon
pKa (Strongest Basic)	-3.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.13 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.51 m³·mol⁻¹	ChemAxon
Polarizability	27.71 Å³	ChemAxon
Number of Rings	4	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

C00020692

Chemspider ID

514539

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

591885

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0¹,³.0⁶,¹⁰]tetradeca-6,12-diene-8,14-dione (NP0159923)

MOL for NP0159923 (5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0¹,³.0⁶,¹⁰]tetradeca-6,12-diene-8,14-dione)

3D MOL for NP0159923 (5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0¹,³.0⁶,¹⁰]tetradeca-6,12-diene-8,14-dione)

3D SDF for NP0159923 (5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0¹,³.0⁶,¹⁰]tetradeca-6,12-diene-8,14-dione)

3D-SDF for NP0159923 (5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0¹,³.0⁶,¹⁰]tetradeca-6,12-diene-8,14-dione)

PDB for NP0159923 (5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0¹,³.0⁶,¹⁰]tetradeca-6,12-diene-8,14-dione)

3D PDB for NP0159923 (5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0¹,³.0⁶,¹⁰]tetradeca-6,12-diene-8,14-dione)

SMILES for NP0159923 (5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0¹,³.0⁶,¹⁰]tetradeca-6,12-diene-8,14-dione)

INCHI for NP0159923 (5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0¹,³.0⁶,¹⁰]tetradeca-6,12-diene-8,14-dione)

Structure for NP0159923 (5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0¹,³.0⁶,¹⁰]tetradeca-6,12-diene-8,14-dione)

3D Structure for NP0159923 (5-hydroxy-3,7,12-trimethyl-2,9-dioxatetracyclo[9.3.0.0¹,³.0⁶,¹⁰]tetradeca-6,12-diene-8,14-dione)