NP-MRD: Showing NP-Card for methyl (3r)-5-[(1s,8r,9r,10r,12r)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-en-9-yl]-3-methylpentanoate (NP0233468)

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Record Information

Version

2.0

Created at

2022-09-06 15:05:01 UTC

Updated at

2022-09-06 15:05:01 UTC

NP-MRD ID

NP0233468

Secondary Accession Numbers

None

Natural Product Identification

Common Name

methyl (3r)-5-[(1s,8r,9r,10r,12r)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-en-9-yl]-3-methylpentanoate

Description

Methyl (3R)-5-[(1S,8R,9R,10R,12R)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0⁴,¹²]Dodec-4-en-9-yl]-3-methylpentanoate belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups. methyl (3r)-5-[(1s,8r,9r,10r,12r)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-en-9-yl]-3-methylpentanoate is found in Moquiniastrum paniculatum. Based on a literature review very few articles have been published on methyl (3R)-5-[(1S,8R,9R,10R,12R)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0⁴,¹²]Dodec-4-en-9-yl]-3-methylpentanoate.

Structure

MOL 3D MOL SDF PDB SMILES InChI


  Mrv1652309062217052D          

 35 38  0  0  1  0            999 V2000
    4.3169   -1.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0314   -2.2211    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.7459   -1.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7459   -0.9836    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.4603   -2.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1748   -1.8086    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    7.1748   -0.9836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8893   -2.2211    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6037   -1.8086    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3182   -2.2211    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    8.7879   -2.8531    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6004   -1.4459    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
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   10.6610   -2.7098    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   10.4614   -3.5103    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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 33 34  1  0  0  0  0
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 25 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END

     RDKit          3D

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M  END


  Mrv1652309062217052D          

 35 38  0  0  1  0            999 V2000
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 10 12  1  0  0  0  0
 12 13  1  6  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 15 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  2  0  0  0  0
 21 22  1  0  0  0  0
 22 23  2  0  0  0  0
 18 23  1  0  0  0  0
 12 24  1  0  0  0  0
 24 25  1  0  0  0  0
 25 26  1  6  0  0  0
 26 27  1  0  0  0  0
 27 28  2  0  0  0  0
 27 29  1  0  0  0  0
 29 30  2  0  0  0  0
 30 31  1  0  0  0  0
 31 32  1  0  0  0  0
 33 32  1  6  0  0  0
 10 33  1  0  0  0  0
 33 34  1  0  0  0  0
 29 34  1  0  0  0  0
 25 34  1  0  0  0  0
 34 35  1  6  0  0  0
M  END
> <DATABASE_ID>
NP0233468

> <DATABASE_NAME>
NP-MRD

> <SMILES>
COC(=O)C[C@H](C)CC[C@@]1(C)[C@H](COC(=O)CC2=CC=CC=C2)C[C@@H]2OC(=O)C3=CCC[C@H]1[C@@]23C

> <INCHI_IDENTIFIER>
InChI=1S/C29H38O6/c1-19(15-25(30)33-4)13-14-28(2)21(18-34-26(31)16-20-9-6-5-7-10-20)17-24-29(3)22(27(32)35-24)11-8-12-23(28)29/h5-7,9-11,19,21,23-24H,8,12-18H2,1-4H3/t19-,21+,23-,24+,28+,29+/m1/s1

> <INCHI_KEY>
YWDQSLLBRGADIX-NFGIMHRHSA-N

> <FORMULA>
C29H38O6

> <MOLECULAR_WEIGHT>
482.617

> <EXACT_MASS>
482.266838944

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
73

> <JCHEM_AVERAGE_POLARIZABILITY>
54.05197020149559

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
methyl (3R)-5-[(1S,8R,9R,10R,12R)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0^{4,12}]dodec-4-en-9-yl]-3-methylpentanoate

> <JCHEM_LOGP>
5.388806038333334

> <JCHEM_MDDR_LIKE_RULE>
1

> <JCHEM_NUMBER_OF_RINGS>
4

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.514194819631245

> <JCHEM_POLAR_SURFACE_AREA>
78.9

> <JCHEM_REFRACTIVITY>
132.40170000000003

> <JCHEM_ROTATABLE_BOND_COUNT>
11

> <JCHEM_RULE_OF_FIVE>
0

> <JCHEM_TRADITIONAL_IUPAC>
methyl (3R)-5-[(1S,8R,9R,10R,12R)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0^{4,12}]dodec-4-en-9-yl]-3-methylpentanoate

> <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       8.058  -3.376   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0       9.392  -4.146   0.000  0.00  0.00           O+0
HETATM    3  C   UNK     0      10.726  -3.376   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      10.726  -1.836   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      12.059  -4.146   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      13.393  -3.376   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      13.393  -1.836   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      14.727  -4.146   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.060  -3.376   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      17.394  -4.146   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      16.404  -5.326   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      17.921  -2.699   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      16.931  -1.519   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      17.458  -0.072   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0      18.974   0.195   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      19.964  -0.984   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0      19.501   1.642   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      21.017   1.910   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      21.544   3.357   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      23.061   3.624   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      24.051   2.445   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      23.524   0.998   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      22.007   0.730   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      19.437  -2.432   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0      20.427  -3.611   0.000  0.00  0.00           C+0
HETATM   26  O   UNK     0      21.966  -3.665   0.000  0.00  0.00           O+0
HETATM   27  C   UNK     0      22.391  -5.145   0.000  0.00  0.00           C+0
HETATM   28  O   UNK     0      23.838  -5.672   0.000  0.00  0.00           O+0
HETATM   29  C   UNK     0      21.114  -6.006   0.000  0.00  0.00           C+0
HETATM   30  C   UNK     0      20.900  -7.531   0.000  0.00  0.00           C+0
HETATM   31  C   UNK     0      19.472  -8.108   0.000  0.00  0.00           C+0
HETATM   32  C   UNK     0      18.258  -7.160   0.000  0.00  0.00           C+0
HETATM   33  C   UNK     0      18.384  -5.326   0.000  0.00  0.00           C+0
HETATM   34  C   UNK     0      19.900  -5.058   0.000  0.00  0.00           C+0
HETATM   35  C   UNK     0      19.528  -6.553   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4    5                                                  
CONECT    4    3                                                            
CONECT    5    3    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12   33                                             
CONECT   11   10                                                            
CONECT   12   10   13   24                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22   18                                                       
CONECT   24   12   25                                                       
CONECT   25   24   26   34                                                  
CONECT   26   25   27                                                       
CONECT   27   26   28   29                                                  
CONECT   28   27                                                            
CONECT   29   27   30   34                                                  
CONECT   30   29   31                                                       
CONECT   31   30   32                                                       
CONECT   32   31   33                                                       
CONECT   33   32   10   34                                                  
CONECT   34   33   29   25   35                                             
CONECT   35   34                                                            
MASTER        0    0    0    0    0    0    0    0   35    0   76    0
END

View in JSmol

Synonyms

Value	Source
Methyl (3R)-5-[(1S,8R,9R,10R,12R)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0,]dodec-4-en-9-yl]-3-methylpentanoic acid	Generator

Chemical Formula

C₂₉H₃₈O₆

Average Mass

482.6170 Da

Monoisotopic Mass

482.26684 Da

IUPAC Name

methyl (3R)-5-[(1S,8R,9R,10R,12R)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0^{4,12}]dodec-4-en-9-yl]-3-methylpentanoate

Traditional Name

methyl (3R)-5-[(1S,8R,9R,10R,12R)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0^{4,12}]dodec-4-en-9-yl]-3-methylpentanoate

CAS Registry Number

Not Available

SMILES

COC(=O)C[C@H](C)CC[C@@]1(C)[C@H](COC(=O)CC2=CC=CC=C2)C[C@@H]2OC(=O)C3=CCC[C@H]1[C@@]23C

InChI Identifier

InChI=1S/C29H38O6/c1-19(15-25(30)33-4)13-14-28(2)21(18-34-26(31)16-20-9-6-5-7-10-20)17-24-29(3)22(27(32)35-24)11-8-12-23(28)29/h5-7,9-11,19,21,23-24H,8,12-18H2,1-4H3/t19-,21+,23-,24+,28+,29+/m1/s1

InChI Key

YWDQSLLBRGADIX-NFGIMHRHSA-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
Gochnatia paniculata	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tricarboxylic acids and derivatives. These are carboxylic acids containing exactly three carboxyl groups.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Tricarboxylic acids and derivatives

Direct Parent

Tricarboxylic acids and derivatives

Alternative Parents

Substituents

Tricarboxylic acid or derivatives
Fatty acid ester
Fatty acid methyl ester
Monocyclic benzene moiety
Gamma butyrolactone
Fatty acyl
Benzenoid
Tetrahydrofuran
Methyl ester
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Lactone
Carboxylic acid ester
Oxacycle
Organoheterocyclic compound
Organooxygen compound
Hydrocarbon derivative
Organic oxide
Organic oxygen compound
Carbonyl group
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	5.39	ChemAxon
pKa (Strongest Basic)	-6.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	11	ChemAxon
Refractivity	132.4 m³·mol⁻¹	ChemAxon
Polarizability	54.05 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	No	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

163006437

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for methyl (3r)-5-[(1s,8r,9r,10r,12r)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-en-9-yl]-3-methylpentanoate (NP0233468)

MOL for NP0233468 (methyl (3r)-5-[(1s,8r,9r,10r,12r)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-en-9-yl]-3-methylpentanoate)

3D MOL for NP0233468 (methyl (3r)-5-[(1s,8r,9r,10r,12r)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-en-9-yl]-3-methylpentanoate)

3D SDF for NP0233468 (methyl (3r)-5-[(1s,8r,9r,10r,12r)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-en-9-yl]-3-methylpentanoate)

3D-SDF for NP0233468 (methyl (3r)-5-[(1s,8r,9r,10r,12r)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-en-9-yl]-3-methylpentanoate)

PDB for NP0233468 (methyl (3r)-5-[(1s,8r,9r,10r,12r)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-en-9-yl]-3-methylpentanoate)

3D PDB for NP0233468 (methyl (3r)-5-[(1s,8r,9r,10r,12r)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-en-9-yl]-3-methylpentanoate)

SMILES for NP0233468 (methyl (3r)-5-[(1s,8r,9r,10r,12r)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-en-9-yl]-3-methylpentanoate)

INCHI for NP0233468 (methyl (3r)-5-[(1s,8r,9r,10r,12r)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-en-9-yl]-3-methylpentanoate)

Structure for NP0233468 (methyl (3r)-5-[(1s,8r,9r,10r,12r)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-en-9-yl]-3-methylpentanoate)

3D Structure for NP0233468 (methyl (3r)-5-[(1s,8r,9r,10r,12r)-9,12-dimethyl-3-oxo-10-{[(2-phenylacetyl)oxy]methyl}-2-oxatricyclo[6.3.1.0⁴,¹²]dodec-4-en-9-yl]-3-methylpentanoate)