NP-MRD: Showing NP-Card for (1r,2r,5s,6r,9r,14r,15r,19s,21r)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-11,22-dione (NP0145441)

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Record Information

Version

2.0

Created at

2022-09-02 00:38:20 UTC

Updated at

2022-09-02 00:38:20 UTC

NP-MRD ID

NP0145441

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,5s,6r,9r,14r,15r,19s,21r)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-11,22-dione

Description

Wilforlide B belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units. (1r,2r,5s,6r,9r,14r,15r,19s,21r)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-11,22-dione is found in Tripterygium regelii. (1r,2r,5s,6r,9r,14r,15r,19s,21r)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-11,22-dione was first documented in 2014 (PMID: 25237706). Based on a literature review a small amount of articles have been published on Wilforlide B (PMID: 34232166) (PMID: 34004587) (PMID: 35763252).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309022202382D          

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M  END

     RDKit          3D

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M  END


  Mrv1652309022202382D          

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   -0.6293   -0.4695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  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
  8  9  1  6  0  0  0
  8 10  1  0  0  0  0
  2 10  1  0  0  0  0
 10 11  1  6  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  6  0  0  0
 13 15  1  0  0  0  0
  8 15  1  0  0  0  0
 15 16  1  6  0  0  0
 16 17  1  0  0  0  0
 17 18  2  0  0  0  0
 19 18  1  1  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  1  0  0  0
 21 23  1  0  0  0  0
 24 23  1  1  0  0  0
 24 25  1  0  0  0  0
 25 26  1  0  0  0  0
 21 26  1  0  0  0  0
 26 27  2  0  0  0  0
 24 28  1  0  0  0  0
 19 28  1  0  0  0  0
 28 29  1  6  0  0  0
 28 30  1  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 18 32  1  0  0  0  0
 13 32  1  0  0  0  0
 32 33  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0145441

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C[C@@]12C[C@@H](OC1=O)[C@]1(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]1C2

> <INCHI_IDENTIFIER>
InChI=1S/C30H44O3/c1-25(2)20-10-13-30(7)21(28(20,5)12-11-22(25)31)9-8-18-19-16-26(3)17-23(33-24(26)32)27(19,4)14-15-29(18,30)6/h8,19-21,23H,9-17H2,1-7H3/t19-,20-,21+,23+,26+,27+,28-,29+,30+/m0/s1

> <INCHI_KEY>
SNNNDALPPUPEKW-RSWVLDSRSA-N

> <FORMULA>
C30H44O3

> <MOLECULAR_WEIGHT>
452.679

> <EXACT_MASS>
452.329045277

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
53.396695402504896

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,5S,6R,9R,14R,15R,19S,21R)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0^{2,19}.0^{5,18}.0^{6,15}.0^{9,14}]tetracos-17-ene-11,22-dione

> <ALOGPS_LOGP>
5.86

> <JCHEM_LOGP>
6.592021196666667

> <ALOGPS_LOGS>
-6.14

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
6

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.95829272985901

> <JCHEM_PKA_STRONGEST_BASIC>
-6.959084669564529

> <JCHEM_POLAR_SURFACE_AREA>
43.370000000000005

> <JCHEM_REFRACTIVITY>
130.8255

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.31e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,5S,6R,9R,14R,15R,19S,21R)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0^{2,19}.0^{5,18}.0^{6,15}.0^{9,14}]tetracos-17-ene-11,22-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      -8.922  -2.033   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -7.464  -2.532   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.227  -1.010   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -8.208  -3.880   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -9.748  -3.910   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -7.412  -5.199   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.872  -5.168   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.129  -3.820   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.333  -5.138   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.925  -2.501   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.181  -1.153   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.641  -1.123   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.845  -2.441   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -2.102  -1.093   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -3.589  -3.790   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.793  -5.108   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      -1.253  -5.078   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      -0.510  -3.729   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.030  -3.699   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       1.621  -5.121   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       3.101  -5.546   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       3.360  -7.064   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       3.628  -3.843   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       3.292  -2.091   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0       4.441  -3.116   0.000  0.00  0.00           O+0
HETATM   26  C   UNK     0       4.356  -4.654   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0       5.705  -5.398   0.000  0.00  0.00           O+0
HETATM   28  C   UNK     0       1.774  -2.350   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0       2.415  -0.950   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       0.978  -1.032   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      -0.562  -1.062   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      -1.306  -2.411   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      -1.175  -0.876   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4   10                                             
CONECT    3    2                                                            
CONECT    4    2    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   10   15                                             
CONECT    9    8                                                            
CONECT   10    8    2   11                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15   32                                             
CONECT   14   13                                                            
CONECT   15   13    8   16                                                  
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19   32                                                  
CONECT   19   18   20   28                                                  
CONECT   20   19   21                                                       
CONECT   21   20   22   23   26                                             
CONECT   22   21                                                            
CONECT   23   21   24                                                       
CONECT   24   23   25   28                                                  
CONECT   25   24   26                                                       
CONECT   26   25   21   27                                                  
CONECT   27   26                                                            
CONECT   28   24   19   29   30                                             
CONECT   29   28                                                            
CONECT   30   28   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   18   13   33                                             
CONECT   33   32                                                            
MASTER        0    0    0    0    0    0    0    0   33    0   76    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₃₀H₄₄O₃

Average Mass

452.6790 Da

Monoisotopic Mass

452.32905 Da

IUPAC Name

(1R,2R,5S,6R,9R,14R,15R,19S,21R)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0^{2,19}.0^{5,18}.0^{6,15}.0^{9,14}]tetracos-17-ene-11,22-dione

Traditional Name

(1R,2R,5S,6R,9R,14R,15R,19S,21R)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0^{2,19}.0^{5,18}.0^{6,15}.0^{9,14}]tetracos-17-ene-11,22-dione

CAS Registry Number

Not Available

SMILES

C[C@@]12C[C@@H](OC1=O)[C@]1(C)CC[C@]3(C)C(=CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@@]34C)[C@@H]1C2

InChI Identifier

InChI=1S/C30H44O3/c1-25(2)20-10-13-30(7)21(28(20,5)12-11-22(25)31)9-8-18-19-16-26(3)17-23(33-24(26)32)27(19,4)14-15-29(18,30)6/h8,19-21,23H,9-17H2,1-7H3/t19-,20-,21+,23+,26+,27+,28-,29+,30+/m0/s1

InChI Key

SNNNDALPPUPEKW-RSWVLDSRSA-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
Tripterygium regelii	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as triterpenoids. These are terpene molecules containing six isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Triterpenoids

Direct Parent

Triterpenoids

Alternative Parents

Substituents

Triterpenoid
Caprolactone
Oxepane
Gamma butyrolactone
Tetrahydrofuran
Carboxylic acid ester
Ketone
Lactone
Cyclic ketone
Monocarboxylic acid or derivatives
Oxacycle
Organoheterocyclic compound
Carboxylic acid derivative
Organooxygen compound
Carbonyl group
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
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	5.86	ALOGPS
logP	6.59	ChemAxon
logS	-6.1	ALOGPS
pKa (Strongest Acidic)	19.96	ChemAxon
pKa (Strongest Basic)	-7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	43.37 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	130.83 m³·mol⁻¹	ChemAxon
Polarizability	53.4 Å³	ChemAxon
Number of Rings	6	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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

152089

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

174362

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Ding Q, Wu Y, Liu W: Molecular mechanism of reproductive toxicity induced by Tripterygium Wilfordii based on network pharmacology. Medicine (Baltimore). 2021 Jul 9;100(27):e26197. doi: 10.1097/MD.0000000000026197. [PubMed:34232166 ]
Zhao K, Sun S, Wang H, Wang L, Qin G, Fan J, Guo M, Wang W: alpha-Glucosidase inhibitory triterpenoids from Euonymus fortunei. Bioorg Chem. 2021 Jun;111:104980. doi: 10.1016/j.bioorg.2021.104980. Epub 2021 May 11. [PubMed:34004587 ]
Qian Q, Gao Y, Xun G, Wang X, Ge J, Zhang H, Mou F, Su S, Wang Q: Synchronous Investigation of the Mechanism and Substance Basis of Tripterygium Glycosides Tablets on Anti-rheumatoid Arthritis and Hepatotoxicity. Appl Biochem Biotechnol. 2022 Nov;194(11):5333-5352. doi: 10.1007/s12010-022-04011-6. Epub 2022 Jun 28. [PubMed:35763252 ]
Su P, Cheng Q, Wang X, Cheng X, Zhang M, Tong Y, Li F, Gao W, Huang L: Characterization of eight terpenoids from tissue cultures of the Chinese herbal plant, Tripterygium wilfordii, by high-performance liquid chromatography coupled with electrospray ionization tandem mass spectrometry. Biomed Chromatogr. 2014 Sep;28(9):1183-92. doi: 10.1002/bmc.3140. [PubMed:25237706 ]
LOTUS database [Link]

Showing NP-Card for (1r,2r,5s,6r,9r,14r,15r,19s,21r)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-11,22-dione (NP0145441)

MOL for NP0145441 ((1r,2r,5s,6r,9r,14r,15r,19s,21r)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-11,22-dione)

3D MOL for NP0145441 ((1r,2r,5s,6r,9r,14r,15r,19s,21r)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-11,22-dione)

3D SDF for NP0145441 ((1r,2r,5s,6r,9r,14r,15r,19s,21r)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-11,22-dione)

3D-SDF for NP0145441 ((1r,2r,5s,6r,9r,14r,15r,19s,21r)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-11,22-dione)

PDB for NP0145441 ((1r,2r,5s,6r,9r,14r,15r,19s,21r)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-11,22-dione)

3D PDB for NP0145441 ((1r,2r,5s,6r,9r,14r,15r,19s,21r)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-11,22-dione)

SMILES for NP0145441 ((1r,2r,5s,6r,9r,14r,15r,19s,21r)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-11,22-dione)

INCHI for NP0145441 ((1r,2r,5s,6r,9r,14r,15r,19s,21r)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-11,22-dione)

Structure for NP0145441 ((1r,2r,5s,6r,9r,14r,15r,19s,21r)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-11,22-dione)

3D Structure for NP0145441 ((1r,2r,5s,6r,9r,14r,15r,19s,21r)-2,5,6,10,10,14,21-heptamethyl-23-oxahexacyclo[19.2.1.0²,¹⁹.0⁵,¹⁸.0⁶,¹⁵.0⁹,¹⁴]tetracos-17-ene-11,22-dione)