NP-MRD: Showing NP-Card for (1r,2r,7s,8r,9r,10s,11r,15r,16s)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadeca-3,12-dien-10-yl acetate (NP0224869)

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Record Information

Version

2.0

Created at

2022-09-06 03:25:29 UTC

Updated at

2022-09-06 03:25:29 UTC

NP-MRD ID

NP0224869

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,2r,7s,8r,9r,10s,11r,15r,16s)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadeca-3,12-dien-10-yl acetate

Description

(1R,2R,7S,8R,9R,10S,11R,15R,16S)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]Octadeca-3,12-dien-10-yl acetate belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom. (1r,2r,7s,8r,9r,10s,11r,15r,16s)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadeca-3,12-dien-10-yl acetate is found in Azadirachta indica. Based on a literature review very few articles have been published on (1R,2R,7S,8R,9R,10S,11R,15R,16S)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]Octadeca-3,12-dien-10-yl acetate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062205252D          

 36 40  0  0  1  0            999 V2000
    3.6900   -2.7534    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  8 18  1  0  0  0  0
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  5 35  1  0  0  0  0
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 35 36  1  1  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309062205252D          

 36 40  0  0  1  0            999 V2000
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    3.6909   -0.5706    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
  2  4  1  0  0  0  0
  5  4  1  6  0  0  0
  5  6  1  0  0  0  0
  6  7  1  6  0  0  0
  8  6  1  1  0  0  0
  8  9  1  0  0  0  0
  9 10  1  6  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
 11 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
  8 18  1  0  0  0  0
 18 19  1  1  0  0  0
 18 20  1  0  0  0  0
 20 21  1  1  0  0  0
 21 22  1  0  0  0  0
 22 23  1  0  0  0  0
 23 24  1  6  0  0  0
 23 25  1  0  0  0  0
 25 26  2  0  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 23 29  1  0  0  0  0
 29 30  1  6  0  0  0
 30 31  1  0  0  0  0
 31 32  2  0  0  0  0
 32 33  1  0  0  0  0
 33 34  1  0  0  0  0
 30 34  2  0  0  0  0
 25 35  1  0  0  0  0
  5 35  1  0  0  0  0
 20 35  1  0  0  0  0
 35 36  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0224869

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)O[C@@H]1[C@H](O)[C@H]2[C@H](O)C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](C(=O)C=C3[C@]12C)C1=COC=C1

> <INCHI_IDENTIFIER>
InChI=1S/C29H36O7/c1-15(30)36-25-23(33)22-24(34)26(2,3)20(32)8-11-27(22,4)18-7-10-28(5)19(29(18,25)6)13-17(31)21(28)16-9-12-35-14-16/h8-9,11-14,18,21-25,33-34H,7,10H2,1-6H3/t18-,21-,22+,23-,24+,25-,27-,28-,29-/m1/s1

> <INCHI_KEY>
GLEJKOVNWRUJSH-CVNHQMOTSA-N

> <FORMULA>
C29H36O7

> <MOLECULAR_WEIGHT>
496.6

> <EXACT_MASS>
496.246103499

> <JCHEM_ACCEPTOR_COUNT>
5

> <JCHEM_ATOM_COUNT>
72

> <JCHEM_AVERAGE_POLARIZABILITY>
53.07203795995525

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,2R,7S,8R,9R,10S,11R,15R,16S)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0^{2,8}.0^{12,16}]octadeca-3,12-dien-10-yl acetate

> <JCHEM_LOGP>
3.0996023920000018

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
5

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.191565567362698

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.579090329699532

> <JCHEM_PKA_STRONGEST_BASIC>
-2.8771528076504023

> <JCHEM_POLAR_SURFACE_AREA>
114.04

> <JCHEM_REFRACTIVITY>
133.3517

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2R,7S,8R,9R,10S,11R,15R,16S)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0^{2,8}.0^{12,16}]octadeca-3,12-dien-10-yl acetate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 06-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-SEP-22         0                                  
HETATM    1  C   UNK     0       6.888  -5.140   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.880  -3.975   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0       4.368  -4.265   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0       6.385  -2.520   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       5.377  -1.356   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.865  -1.646   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0       3.360  -3.101   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       2.857  -0.481   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.405  -0.994   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0       1.237  -2.525   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.099  -0.178   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.406  -1.633   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.432  -0.010   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.078   1.352   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -1.533   1.856   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0       1.008   2.443   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.539   2.275   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       3.362   0.974   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       3.974   2.387   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       4.874   1.264   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       5.379   2.719   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       6.891   3.009   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       7.899   1.845   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       8.553   3.239   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       7.394   0.390   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0       8.622  -0.540   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       9.886   0.341   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      11.341  -0.164   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0       9.439   1.814   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      10.368   3.042   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0       9.921   4.516   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      11.185   5.396   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0      12.413   4.467   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0      11.908   3.012   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       5.882   0.099   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       6.890  -1.065   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   35                                                  
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9   18                                                  
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14   11   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17    8   19   20                                             
CONECT   19   18                                                            
CONECT   20   18   21   35                                                  
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   24   25   29                                             
CONECT   24   23                                                            
CONECT   25   23   26   35                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   23   30                                                  
CONECT   30   29   31   34                                                  
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   34                                                       
CONECT   34   33   30                                                       
CONECT   35   25    5   20   36                                             
CONECT   36   35                                                            
MASTER        0    0    0    0    0    0    0    0   36    0   80    0
END

View in JSmol

Synonyms

Value	Source
(1R,2R,7S,8R,9R,10S,11R,15R,16S)-15-(Furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0,.0,]octadeca-3,12-dien-10-yl acetic acid	Generator

Chemical Formula

C₂₉H₃₆O₇

Average Mass

496.6000 Da

Monoisotopic Mass

496.24610 Da

IUPAC Name

(1R,2R,7S,8R,9R,10S,11R,15R,16S)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0^{2,8}.0^{12,16}]octadeca-3,12-dien-10-yl acetate

Traditional Name

(1R,2R,7S,8R,9R,10S,11R,15R,16S)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0^{2,8}.0^{12,16}]octadeca-3,12-dien-10-yl acetate

CAS Registry Number

Not Available

SMILES

CC(=O)O[C@@H]1[C@H](O)[C@H]2[C@H](O)C(C)(C)C(=O)C=C[C@]2(C)[C@H]2CC[C@@]3(C)[C@@H](C(=O)C=C3[C@]12C)C1=COC=C1

InChI Identifier

InChI=1S/C29H36O7/c1-15(30)36-25-23(33)22-24(34)26(2,3)20(32)8-11-27(22,4)18-7-10-28(5)19(29(18,25)6)13-17(31)21(28)16-9-12-35-14-16/h8-9,11-14,18,21-25,33-34H,7,10H2,1-6H3/t18-,21-,22+,23-,24+,25-,27-,28-,29-/m1/s1

InChI Key

GLEJKOVNWRUJSH-CVNHQMOTSA-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
Azadirachta indica	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as heteroaromatic compounds. Heteroaromatic compounds are compounds containing an aromatic ring where a carbon atom is linked to an hetero atom.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Heteroaromatic compounds

Sub Class

Not Available

Direct Parent

Heteroaromatic compounds

Alternative Parents

Substituents

Cyclic alcohol
Furan
Heteroaromatic compound
Carboxylic acid ester
Ketone
Cyclic ketone
Secondary alcohol
Carboxylic acid derivative
Oxacycle
Monocarboxylic acid or derivatives
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Alcohol
Carbonyl group
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	3.1	ChemAxon
pKa (Strongest Acidic)	13.58	ChemAxon
pKa (Strongest Basic)	-2.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	5	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	114.04 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	133.35 m³·mol⁻¹	ChemAxon
Polarizability	53.07 Å³	ChemAxon
Number of Rings	5	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

163070745

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for (1r,2r,7s,8r,9r,10s,11r,15r,16s)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadeca-3,12-dien-10-yl acetate (NP0224869)

MOL for NP0224869 ((1r,2r,7s,8r,9r,10s,11r,15r,16s)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadeca-3,12-dien-10-yl acetate)

3D MOL for NP0224869 ((1r,2r,7s,8r,9r,10s,11r,15r,16s)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadeca-3,12-dien-10-yl acetate)

3D SDF for NP0224869 ((1r,2r,7s,8r,9r,10s,11r,15r,16s)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadeca-3,12-dien-10-yl acetate)

3D-SDF for NP0224869 ((1r,2r,7s,8r,9r,10s,11r,15r,16s)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadeca-3,12-dien-10-yl acetate)

PDB for NP0224869 ((1r,2r,7s,8r,9r,10s,11r,15r,16s)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadeca-3,12-dien-10-yl acetate)

3D PDB for NP0224869 ((1r,2r,7s,8r,9r,10s,11r,15r,16s)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadeca-3,12-dien-10-yl acetate)

SMILES for NP0224869 ((1r,2r,7s,8r,9r,10s,11r,15r,16s)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadeca-3,12-dien-10-yl acetate)

INCHI for NP0224869 ((1r,2r,7s,8r,9r,10s,11r,15r,16s)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadeca-3,12-dien-10-yl acetate)

Structure for NP0224869 ((1r,2r,7s,8r,9r,10s,11r,15r,16s)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadeca-3,12-dien-10-yl acetate)

3D Structure for NP0224869 ((1r,2r,7s,8r,9r,10s,11r,15r,16s)-15-(furan-3-yl)-7,9-dihydroxy-2,6,6,11,16-pentamethyl-5,14-dioxotetracyclo[9.7.0.0²,⁸.0¹²,¹⁶]octadeca-3,12-dien-10-yl acetate)