NP-MRD: Showing NP-Card for (1r,7s,8as)-1,8a-dimethyl-7-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalene (NP0212838)

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Record Information

Version

2.0

Created at

2022-09-05 11:37:24 UTC

Updated at

2022-09-05 11:37:24 UTC

NP-MRD ID

NP0212838

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(1r,7s,8as)-1,8a-dimethyl-7-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalene

Description

Eremophilene belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5. (1r,7s,8as)-1,8a-dimethyl-7-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalene is found in Picea glehnii, Sorangium cellulosum and Valeriana officinalis. (1r,7s,8as)-1,8a-dimethyl-7-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalene was first documented in 2015 (PMID: 25504914). Eremophilene is possibly neutral (PMID: 27294564) (PMID: 26947062).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 40  0  0  0  0  0  0  0  0999 V2000
    3.3179   -0.2494    1.8611 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8791   -0.3657    0.6236 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7216   -1.0572   -0.3871 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5720    0.1848    0.2581 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6761    1.2429   -0.8443 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3501    2.0130   -0.7741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7024    1.2080   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5104    1.7991    0.7506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5744    1.0581    1.4561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2881   -0.4194    1.5455 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7990   -1.0151    0.2733 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.9869   -1.3619   -0.6361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7530   -0.2423   -0.4446 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0642   -0.2918   -1.9468 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6104   -0.8624   -0.2603 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7289    0.2432    2.6017 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2846   -0.6625    2.1095 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7807   -0.9548   -0.0738 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6593   -0.5512   -1.3853 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4374   -2.1311   -0.4626 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1131    0.7021    1.1220 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8273    0.7738   -1.8276 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5269    1.8917   -0.6092 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0375    2.3531   -1.7780 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5607    2.8922   -0.1458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4065    2.8588    0.9476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5417    1.2647    0.9599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6947    1.4165    2.5168 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1980   -0.9433    1.8683 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5123   -0.5717    2.3222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3570   -2.0226    0.5350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6404   -1.8677   -1.5397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6156   -0.4801   -0.7949 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5859   -2.1310   -0.0651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8466   -1.2686   -2.3824 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4588    0.4653   -2.4846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1295    0.0265   -2.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0210   -1.2770   -1.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5610   -1.6672    0.4972 H   0  0  0  0  0  0  0  0  0  0  0  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 13 14  1  6
 13 15  1  0
  4  2  1  0
  2  3  1  0
  2  1  2  3
 15  4  1  0
 13  7  1  0
  4 21  1  1
  5 22  1  0
  5 23  1  0
  6 24  1  0
  6 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  1
 12 32  1  0
 12 33  1  0
 12 34  1  0
 14 35  1  0
 14 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
  3 18  1  0
  3 19  1  0
  3 20  1  0
  1 16  1  0
  1 17  1  0
M  END


  Mrv1652307301920052D          

 17 18  0  0  1  0            999 V2000
    5.0013   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868   -0.8250    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
  9  8  1  0  0  0  0
 11  1  2  0  0  0  0
 11  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  6  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  1  0  0  0  0
 13 11  1  0  0  0  0
 14  7  2  0  0  0  0
 14  9  1  0  0  0  0
 15  4  1  6  0  0  0
 15 10  1  0  0  0  0
 12 15  1  0  0  0  0
 15 14  1  0  0  0  0
 12 16  1  1  0  0  0
 13 17  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0212838

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CCC2=CCC[C@@]([H])(C)[C@]2(C)C1)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-11(2)13-8-9-14-7-5-6-12(3)15(14,4)10-13/h7,12-13H,1,5-6,8-10H2,2-4H3/t12-,13+,15+/m1/s1

> <INCHI_KEY>
QEBNYNLSCGVZOH-IPYPFGDCSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.737739932701167

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3S,4aS,5R)-4a,5-dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene

> <JCHEM_LOGP>
4.519309391666669

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
67.45240000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(1R,7S,8aS)-1,8a-dimethyl-7-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1H-naphthalene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 30-JUL-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   30-JUL-19         0                                  
HETATM    1  C   UNK     0       9.336  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.669   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       9.336  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       2.667  -1.540   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0       8.002  -1.540   0.000  0.00  0.00           H+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   15                                                            
CONECT    5    6    7                                                       
CONECT    6    5   12                                                       
CONECT    7    5   14                                                       
CONECT    8    9   13                                                       
CONECT    9    8   14                                                       
CONECT   10   13   15                                                       
CONECT   11    1    2   13                                                  
CONECT   12    3    6   15   16                                             
CONECT   13    8   10   11   17                                             
CONECT   14    7    9   15                                                  
CONECT   15    4   10   12   14                                             
CONECT   16   12                                                            
CONECT   17   13                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(3S,4aS,5R)-4a,5-dimethyl-3-(prop-1-en-2-yl)-1,2,3,4,4a,5,6,7-octahydronaphthalene

Traditional Name

(1R,7S,8aS)-1,8a-dimethyl-7-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1H-naphthalene

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CCC2=CCC[C@@]([H])(C)[C@]2(C)C1)C(C)=C

InChI Identifier

InChI=1S/C15H24/c1-11(2)13-8-9-14-7-5-6-12(3)15(14,4)10-13/h7,12-13H,1,5-6,8-10H2,2-4H3/t12-,13+,15+/m1/s1

InChI Key

QEBNYNLSCGVZOH-IPYPFGDCSA-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
Picea glehnii	LOTUS Database	35616633
Sorangium cellulosum	LOTUS Database	35616633
Valeriana officinalis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic 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	4.52	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.45 m³·mol⁻¹	ChemAxon
Polarizability	25.74 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

FDB014408

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-20084

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6431897

PDB ID

Not Available

ChEBI ID

137562

Good Scents ID

Not Available

References

General References

Burkhardt I, Siemon T, Henrot M, Studt L, Rosler S, Tudzynski B, Christmann M, Dickschat JS: Mechanistic Characterisation of Two Sesquiterpene Cyclases from the Plant Pathogenic Fungus Fusarium fujikuroi. Angew Chem Int Ed Engl. 2016 Jul 18;55(30):8748-51. doi: 10.1002/anie.201603782. Epub 2016 Jun 13. [PubMed:27294564 ]
Schifrin A, Ly TT, Gunnewich N, Zapp J, Thiel V, Schulz S, Hannemann F, Khatri Y, Bernhardt R: Characterization of the gene cluster CYP264B1-geoA from Sorangium cellulosum So ce56: biosynthesis of (+)-eremophilene and its hydroxylation. Chembiochem. 2015 Jan 19;16(2):337-44. doi: 10.1002/cbic.201402443. Epub 2014 Dec 12. [PubMed:25504914 ]
Schifrin A, Khatri Y, Kirsch P, Thiel V, Schulz S, Bernhardt R: A single terpene synthase is responsible for a wide variety of sesquiterpenes in Sorangium cellulosum Soce56. Org Biomol Chem. 2016 Apr 7;14(13):3385-93. doi: 10.1039/c6ob00130k. Epub 2016 Mar 7. [PubMed:26947062 ]
LOTUS database [Link]

Showing NP-Card for (1r,7s,8as)-1,8a-dimethyl-7-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalene (NP0212838)

MOL for NP0212838 ((1r,7s,8as)-1,8a-dimethyl-7-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalene)

3D MOL for NP0212838 ((1r,7s,8as)-1,8a-dimethyl-7-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalene)

3D SDF for NP0212838 ((1r,7s,8as)-1,8a-dimethyl-7-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalene)

3D-SDF for NP0212838 ((1r,7s,8as)-1,8a-dimethyl-7-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalene)

PDB for NP0212838 ((1r,7s,8as)-1,8a-dimethyl-7-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalene)

3D PDB for NP0212838 ((1r,7s,8as)-1,8a-dimethyl-7-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalene)

SMILES for NP0212838 ((1r,7s,8as)-1,8a-dimethyl-7-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalene)

INCHI for NP0212838 ((1r,7s,8as)-1,8a-dimethyl-7-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalene)

Structure for NP0212838 ((1r,7s,8as)-1,8a-dimethyl-7-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalene)

3D Structure for NP0212838 ((1r,7s,8as)-1,8a-dimethyl-7-(prop-1-en-2-yl)-2,3,5,6,7,8-hexahydro-1h-naphthalene)