NP-MRD: Showing NP-Card for 13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate (NP0184976)

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Record Information

Version

2.0

Created at

2022-09-04 00:14:54 UTC

Updated at

2022-09-04 00:14:54 UTC

NP-MRD ID

NP0184976

Secondary Accession Numbers

None

Natural Product Identification

Common Name

13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate

Description

13-(Acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]Hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid. 13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate is found in Taxus cuspidata. 13-(Acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]Hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1533004241502322D          

 39 42  0  0  0  0            999 V2000
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  7 37  1  0  0  0  0
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 37 39  1  0  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1533004241502322D          

 39 42  0  0  0  0            999 V2000
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    6.7914   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0789   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4914   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8414   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164   -1.5395    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6039   -2.2539    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2539   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9824   -1.2123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9824   -0.4377    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
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
 10  8  1  4  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 11 18  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 22 20  1  4  0  0  0
 22 23  2  0  0  0  0
 23 24  1  0  0  0  0
 24 25  2  0  0  0  0
 25 26  1  0  0  0  0
 26 27  2  0  0  0  0
 27 28  1  0  0  0  0
 28 29  2  0  0  0  0
 24 29  1  0  0  0  0
 13 30  1  0  0  0  0
 30 31  2  0  0  0  0
 30 32  1  0  0  0  0
 32 33  1  0  0  0  0
 32 34  1  0  0  0  0
 34 35  2  0  0  0  0
  5 35  1  0  0  0  0
 35 36  1  0  0  0  0
 34 37  1  0  0  0  0
  7 37  1  0  0  0  0
 37 38  1  0  0  0  0
 37 39  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0184976

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(=O)OC1CC2C(O)C=C3CC(C)(C(O)CC3OC(=O)C=CC3=CC=CC=C3)C(=O)C(O)C(=C1C)C2(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C31H38O8/c1-17-23(38-18(2)32)14-21-22(33)13-20-16-31(5,29(37)28(36)27(17)30(21,3)4)25(34)15-24(20)39-26(35)12-11-19-9-7-6-8-10-19/h6-13,21-25,28,33-34,36H,14-16H2,1-5H3

> <INCHI_KEY>
VMOOHFUGVODOEB-UHFFFAOYSA-N

> <FORMULA>
C31H38O8

> <MOLECULAR_WEIGHT>
538.637

> <EXACT_MASS>
538.256668184

> <JCHEM_ACCEPTOR_COUNT>
6

> <JCHEM_ATOM_COUNT>
77

> <JCHEM_AVERAGE_POLARIZABILITY>
57.19969331084409

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
3

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate

> <ALOGPS_LOGP>
2.32

> <JCHEM_LOGP>
3.0492539676666635

> <ALOGPS_LOGS>
-4.37

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
14.349867641287457

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.476360603023357

> <JCHEM_PKA_STRONGEST_BASIC>
-3.005840460200786

> <JCHEM_POLAR_SURFACE_AREA>
130.35999999999999

> <JCHEM_REFRACTIVITY>
145.97480000000002

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate

> <JCHEM_VEBER_RULE>
0

$$$$

HEADER    PROTEIN                                 24-APR-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-APR-15         0                                  
HETATM    1  C   UNK     0      -0.413   1.127   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.183  -0.206   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -2.723  -0.206   0.000  0.00  0.00           O+0
HETATM    4  O   UNK     0      -0.413  -1.540   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0       1.127  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.897  -0.206   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.437  -0.206   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.207   1.127   0.000  0.00  0.00           C+0
HETATM    9  O   UNK     0       3.437   2.461   0.000  0.00  0.00           O+0
HETATM   10  C   UNK     0       5.747   1.127   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.517  -0.206   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.747  -1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.517  -2.874   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       7.287  -4.207   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       8.057  -2.874   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       8.827  -4.207   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       8.827  -1.540   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.057  -0.206   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0       8.827   1.127   0.000  0.00  0.00           O+0
HETATM   20  C   UNK     0      10.367   1.127   0.000  0.00  0.00           C+0
HETATM   21  O   UNK     0      11.137   2.461   0.000  0.00  0.00           O+0
HETATM   22  C   UNK     0      11.137  -0.206   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      12.677  -0.206   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      13.447  -1.540   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      14.987  -1.540   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      15.757  -2.874   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0      14.987  -4.207   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.447  -4.207   0.000  0.00  0.00           C+0
HETATM   29  C   UNK     0      12.677  -2.874   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0       5.747  -4.207   0.000  0.00  0.00           C+0
HETATM   31  O   UNK     0       6.517  -5.541   0.000  0.00  0.00           O+0
HETATM   32  C   UNK     0       4.207  -4.207   0.000  0.00  0.00           C+0
HETATM   33  O   UNK     0       3.437  -5.541   0.000  0.00  0.00           O+0
HETATM   34  C   UNK     0       3.437  -2.874   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0       1.897  -2.874   0.000  0.00  0.00           C+0
HETATM   36  C   UNK     0       1.127  -4.207   0.000  0.00  0.00           C+0
HETATM   37  C   UNK     0       4.207  -1.540   0.000  0.00  0.00           C+0
HETATM   38  C   UNK     0       5.567  -2.263   0.000  0.00  0.00           C+0
HETATM   39  C   UNK     0       5.567  -0.817   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                                                       
CONECT    7    6    8   37                                                  
CONECT    8    7    9   10                                                  
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10   12   18                                                  
CONECT   12   11   13                                                       
CONECT   13   12   14   15   30                                             
CONECT   14   13                                                            
CONECT   15   13   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   11   19                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20                                                            
CONECT   22   20   23                                                       
CONECT   23   22   24                                                       
CONECT   24   23   25   29                                                  
CONECT   25   24   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26   28                                                       
CONECT   28   27   29                                                       
CONECT   29   28   24                                                       
CONECT   30   13   31   32                                                  
CONECT   31   30                                                            
CONECT   32   30   33   34                                                  
CONECT   33   32                                                            
CONECT   34   32   35   37                                                  
CONECT   35   34    5   36                                                  
CONECT   36   35                                                            
CONECT   37   34    7   38   39                                             
CONECT   38   37                                                            
CONECT   39   37                                                            
MASTER        0    0    0    0    0    0    0    0   39    0   84    0
END

View in JSmol

Synonyms

Value	Source
13-(Acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1,]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoic acid	Generator
13-(Acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoic acid	Generator

Chemical Formula

C₃₁H₃₈O₈

Average Mass

538.6370 Da

Monoisotopic Mass

538.25667 Da

IUPAC Name

13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate

Traditional Name

13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate

CAS Registry Number

Not Available

SMILES

CC(=O)OC1CC2C(O)C=C3CC(C)(C(O)CC3OC(=O)C=CC3=CC=CC=C3)C(=O)C(O)C(=C1C)C2(C)C

InChI Identifier

InChI=1S/C31H38O8/c1-17-23(38-18(2)32)14-21-22(33)13-20-16-31(5,29(37)28(36)27(17)30(21,3)4)25(34)15-24(20)39-26(35)12-11-19-9-7-6-8-10-19/h6-13,21-25,28,33-34,36H,14-16H2,1-5H3

InChI Key

VMOOHFUGVODOEB-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
Taxus cuspidata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cinnamic acid esters. These are compound containing an ester derivative of cinnamic acid.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Cinnamic acids and derivatives

Sub Class

Cinnamic acid esters

Direct Parent

Cinnamic acid esters

Alternative Parents

Substituents

Cinnamic acid ester
Styrene
Fatty acid ester
Monocyclic benzene moiety
Dicarboxylic acid or derivatives
Fatty acyl
Benzenoid
Cyclic alcohol
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Secondary alcohol
Ketone
Carboxylic acid derivative
Polyol
Hydrocarbon derivative
Organic oxide
Alcohol
Carbonyl group
Organic oxygen compound
Organooxygen compound
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic 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	2.32	ALOGPS
logP	3.05	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	11.48	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	3	ChemAxon
Polar Surface Area	130.36 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	145.97 m³·mol⁻¹	ChemAxon
Polarizability	57.2 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	Yes	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

Not Available

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for 13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate (NP0184976)

MOL for NP0184976 (13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate)

3D MOL for NP0184976 (13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate)

3D SDF for NP0184976 (13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate)

3D-SDF for NP0184976 (13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate)

PDB for NP0184976 (13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate)

3D PDB for NP0184976 (13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate)

SMILES for NP0184976 (13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate)

INCHI for NP0184976 (13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate)

Structure for NP0184976 (13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate)

3D Structure for NP0184976 (13-(acetyloxy)-2,7,10-trihydroxy-8,12,15,15-tetramethyl-9-oxotricyclo[9.3.1.1⁴,⁸]hexadeca-3,11-dien-5-yl 3-phenylprop-2-enoate)