NP-MRD: Showing NP-Card for (1r,3e,7e,11r)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene (NP0145189)

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Record Information

Version

2.0

Created at

2022-09-02 00:19:56 UTC

Updated at

2022-09-02 00:19:56 UTC

NP-MRD ID

NP0145189

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,3e,7e,11r)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene

Description

Humulene epoxide II belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms). (1r,3e,7e,11r)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene is found in Callicarpa japonica, Teucrium polium and Teucrium scorodonia. (1r,3e,7e,11r)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene was first documented in 2021 (PMID: 33867898). Based on a literature review a small amount of articles have been published on Humulene epoxide II (PMID: 35889501) (PMID: 35766214) (PMID: 35625543) (PMID: 35436102).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 40 41  0  0  0  0  0  0  0  0999 V2000
    0.2697    3.0792   -1.6544 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2289    2.1036   -0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8802    1.4960   -0.1714 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0293    0.5118    0.9368 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9879   -0.6023    0.5601 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0837   -1.5403    1.7288 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3687    0.0602    0.4391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6460   -1.2562   -0.7209 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5595   -1.9317   -0.9747 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5666   -2.1953   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7583   -1.3033   -0.2646 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.7665   -1.3583    0.8622 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4254   -1.3634   -1.5152 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7017   -0.2363   -1.1325 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.4562    0.9717   -0.6023 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5596    1.9247    0.1276 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0050    2.7633   -2.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7002    3.1974   -2.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5459    4.0575   -1.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8114    1.6964   -0.7139 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0981    0.1876    1.3820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5727    1.0733    1.7587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0706   -1.4646    2.2753 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9988   -2.6028    1.4700 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3373   -1.3014    2.5403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5170    0.4376   -0.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4974    0.8733    1.1699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1758   -0.6832    0.6104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3944   -1.1539   -1.5340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4460   -2.3654   -1.9904 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3034   -2.1410    1.0218 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9264   -3.2410   -0.2099 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7658   -2.4304    1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8047   -1.1735    0.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4624   -0.7631    1.7461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9418    0.0427   -1.8680 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8399    1.5135   -1.4963 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3131    0.7257    0.0179 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0926    2.8897    0.2564 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4415    1.5025    1.1486 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  1  0
  5  6  1  0
  5  7  1  0
  5  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  1
 11 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16  2  1  0
 14 11  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  6 23  1  0
  6 24  1  0
  6 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  6
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
M  END


  Mrv1652309022202192D          

 16 17  0  0  1  0            999 V2000
    3.8725    0.2397    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2833   -0.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4040   -1.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0741   -1.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9368   -2.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7618   -2.5662    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0859   -3.3836    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1636   -2.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5278   -2.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7546   -2.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1188   -2.0964    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5931   -2.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4830   -1.5707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2561   -1.2829    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.0878   -0.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4698   -0.2003    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  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  6  0  0  0
 11 13  1  0  0  0  0
 14 13  1  6  0  0  0
 11 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0145189

> <DATABASE_NAME>
NP-MRD

> <SMILES>
C\C1=C/CC(C)(C)\C=C\C[C@@]2(C)O[C@@H]2CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-12-6-7-13-15(4,16-13)10-5-9-14(2,3)11-8-12/h5,8-9,13H,6-7,10-11H2,1-4H3/b9-5+,12-8+/t13-,15-/m1/s1

> <INCHI_KEY>
QTGAEXCCAPTGLB-UOAUIWSESA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.356

> <EXACT_MASS>
220.182715393

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
40

> <JCHEM_AVERAGE_POLARIZABILITY>
26.416475510810887

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,3E,7E,11R)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene

> <ALOGPS_LOGP>
5.03

> <JCHEM_LOGP>
3.9774975963333326

> <ALOGPS_LOGS>
-4.43

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.2267160324202

> <JCHEM_POLAR_SURFACE_AREA>
12.53

> <JCHEM_REFRACTIVITY>
70.309

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,3E,7E,11R)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene

> <JCHEM_VEBER_RULE>
1

$$$$

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       7.229   0.447   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.129  -0.630   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.354  -2.154   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.605  -3.283   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       7.349  -4.801   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.889  -4.790   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.627  -6.316   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.905  -5.339   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.719  -4.357   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.275  -4.895   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.088  -3.913   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.107  -5.100   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       0.902  -2.932   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0       2.345  -2.395   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.897  -1.739   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       4.610  -0.374   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   16                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7    8                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    5    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12   13   14                                             
CONECT   12   11                                                            
CONECT   13   11   14                                                       
CONECT   14   13   11   15                                                  
CONECT   15   14   16                                                       
CONECT   16   15    2                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O

Average Mass

220.3560 Da

Monoisotopic Mass

220.18272 Da

IUPAC Name

(1R,3E,7E,11R)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene

Traditional Name

(1R,3E,7E,11R)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene

CAS Registry Number

Not Available

SMILES

C\C1=C/CC(C)(C)\C=C\C[C@@]2(C)O[C@@H]2CC1

InChI Identifier

InChI=1S/C15H24O/c1-12-6-7-13-15(4,16-13)10-5-9-14(2,3)11-8-12/h5,8-9,13H,6-7,10-11H2,1-4H3/b9-5+,12-8+/t13-,15-/m1/s1

InChI Key

QTGAEXCCAPTGLB-UOAUIWSESA-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
Callicarpa japonica	LOTUS Database	35616633
Teucrium polium	LOTUS Database	35616633
Teucrium scorodonia	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as epoxides. Epoxides are compounds containing a cyclic ether with three ring atoms(one oxygen and two carbon atoms).

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Epoxides

Sub Class

Not Available

Direct Parent

Epoxides

Alternative Parents

Substituents

Oxacycle
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
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	5.03	ALOGPS
logP	3.98	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.31 m³·mol⁻¹	ChemAxon
Polarizability	26.42 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	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

C00012444

Chemspider ID

8879522

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10704181

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Fu J, Gao Y, Xing X: Preliminary Study on Phytochemical Constituents and Biological Activities of Essential Oil from Myriactis nepalensis Less. Molecules. 2022 Jul 20;27(14). pii: molecules27144631. doi: 10.3390/molecules27144631. [PubMed:35889501 ]
Lyna B, Fouzia M, Okkacha B, Dib MEA, Muselli A: A combined in vitro-in silico approach for the discovery of novel endogenous enzymatic and ctDNA sequence of bioactive molecules from aerial and root parts of Centaurea sulphurea as antioxidant's agents. J Biomol Struct Dyn. 2022 Jun 29:1-22. doi: 10.1080/07391102.2022.2090438. [PubMed:35766214 ]
Santos ACD, Nogueira ML, Oliveira FP, Costa EV, Bezerra DP: Essential Oils of Duguetia Species A. St. Hill (Annonaceae): Chemical Diversity and Pharmacological Potential. Biomolecules. 2022 Apr 21;12(5). pii: biom12050615. doi: 10.3390/biom12050615. [PubMed:35625543 ]
Zheljazkov VD, Noller JS, Maggi F, Dale R: Terpenes and Cannabinoids Yields and Profile from Direct-Seeded and Transplanted CBD-Cannabis sativa. J Agric Food Chem. 2022 Aug 31;70(34):10417-10428. doi: 10.1021/acs.jafc.1c06912. Epub 2022 Apr 18. [PubMed:35436102 ]
Amparo TR, Seibert JB, Silveira BM, Costa FSF, Almeida TC, Braga SFP, da Silva GN, Dos Santos ODH, de Souza GHB: Brazilian essential oils as source for the discovery of new anti-COVID-19 drug: a review guided by in silico study. Phytochem Rev. 2021;20(5):1013-1032. doi: 10.1007/s11101-021-09754-4. Epub 2021 Apr 13. [PubMed:33867898 ]
LOTUS database [Link]

Showing NP-Card for (1r,3e,7e,11r)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene (NP0145189)

MOL for NP0145189 ((1r,3e,7e,11r)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene)

3D MOL for NP0145189 ((1r,3e,7e,11r)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene)

3D SDF for NP0145189 ((1r,3e,7e,11r)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene)

3D-SDF for NP0145189 ((1r,3e,7e,11r)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene)

PDB for NP0145189 ((1r,3e,7e,11r)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene)

3D PDB for NP0145189 ((1r,3e,7e,11r)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene)

SMILES for NP0145189 ((1r,3e,7e,11r)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene)

INCHI for NP0145189 ((1r,3e,7e,11r)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene)

Structure for NP0145189 ((1r,3e,7e,11r)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene)

3D Structure for NP0145189 ((1r,3e,7e,11r)-1,5,5,8-tetramethyl-12-oxabicyclo[9.1.0]dodeca-3,7-diene)