NP-MRD: Showing NP-Card for (2s,5s)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol (NP0269180)

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Record Information

Version

2.0

Created at

2022-09-08 14:33:22 UTC

Updated at

2022-09-08 14:33:22 UTC

NP-MRD ID

NP0269180

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2s,5s)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol

Description

Trans-Sesquisabinene hydrate belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. (2s,5s)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol is found in Daucus carota. (2s,5s)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol was first documented in 2016 (PMID: 27448034). Based on a literature review a small amount of articles have been published on trans-Sesquisabinene hydrate (PMID: 32041311) (PMID: 30268652) (PMID: 29996001) (PMID: 29606759).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 43  0  0  0  0  0  0  0  0999 V2000
   -5.4019   -0.1568    1.3447 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2356    0.0535    0.4450 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4523    0.1684   -1.0247 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0207    0.1366    0.9549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8045    0.3479    0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9060   -0.8159    0.3146 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3777   -0.8070   -0.4494 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1867   -0.7753   -1.9412 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3921    0.1579    0.0600 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.1028   -0.2271    1.3707 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3153    0.6574    1.4408 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7393    0.7578    0.0158 C   0  0  2  0  0  0  0  0  0  0  0  0
    4.4384   -0.5226   -0.4163 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4888    1.8821   -0.2710 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.4066    0.8164   -0.7170 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.2880    1.6154   -0.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9619   -1.0445    0.9284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1030    0.6950    1.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1046   -0.3742    2.3706 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4763   -0.1455   -1.2690 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7730   -0.5757   -1.5215 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2638    1.1852   -1.4100 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9068    0.0481    2.0267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3235    1.2703    0.5208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1497    0.5066   -0.9154 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4726   -1.7459    0.0887 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6553   -0.8695    1.3935 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8079   -1.8388   -0.2467 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0153   -1.7990   -2.3684 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0166   -0.3506   -2.4997 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7352   -0.2025   -2.2354 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4330   -0.0878    2.2315 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4550   -1.2666    1.2463 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1074    0.1095    2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1299    1.6270    1.9230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7599   -1.1751   -1.0124 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8072   -1.0842    0.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3556   -0.2521   -1.0172 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4798    1.9951   -1.2544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5144    0.8427   -1.7995 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5444    2.3195    0.7148 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5846    2.0795   -0.8372 H   0  0  0  0  0  0  0  0  0  0  0  0
  8  7  1  0
  7  6  1  0
  6  5  1  0
  5  4  1  0
  4  2  2  3
  2  1  1  0
  2  3  1  0
  7  9  1  0
  9 16  1  1
 16 15  1  0
 15 12  1  0
 12 13  1  0
 12 14  1  1
 12 11  1  0
 11 10  1  0
 15  9  1  0
 10  9  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  7 28  1  6
  6 26  1  0
  6 27  1  0
  5 24  1  0
  5 25  1  0
  4 23  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
 16 41  1  0
 16 42  1  0
 15 40  1  6
 13 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 11 34  1  0
 11 35  1  0
 10 32  1  0
 10 33  1  0
M  END


  Mrv1652309082216332D          

 16 17  0  0  1  0            999 V2000
   -2.0102    2.8710    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1897    2.7848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7048    3.4522    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8542    2.0311    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0337    1.9449    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3019    1.1912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1224    1.1050    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6073    1.7724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579    0.3513    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.2425    0.6062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7275   -0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2425   -0.7286    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.9570   -1.1411    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9070   -1.4823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.4579   -0.4737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7434   -0.0612    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  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
  9  7  1  1  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  1  0  0  0
 12 14  1  6  0  0  0
 12 15  1  0  0  0  0
  9 15  1  0  0  0  0
 15 16  1  0  0  0  0
  9 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0269180

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(CCC=C(C)C)[C@]12CC1[C@@](C)(O)CC2

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-11(2)6-5-7-12(3)15-9-8-14(4,16)13(15)10-15/h6,12-13,16H,5,7-10H2,1-4H3/t12?,13?,14-,15-/m0/s1

> <INCHI_KEY>
IRDFGGRWKUKANK-WUCCLRPBSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.372

> <EXACT_MASS>
222.198365457

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.006971931853947

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2S,5S)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol

> <JCHEM_LOGP>
3.5517479776666674

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.131148001331002

> <JCHEM_PKA_STRONGEST_BASIC>
-0.991835864217819

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
69.357

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(2S,5S)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0      -3.752   5.359   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.221   5.198   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.316   6.444   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.594   3.791   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.063   3.630   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.563   2.224   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.095   2.063   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.000   3.308   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.721   0.656   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.186   1.132   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.091  -0.114   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.186  -1.360   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.520  -2.130   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0       3.560  -2.767   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0       2.721  -0.884   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.388  -0.114   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                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10   15   16                                             
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14   15                                             
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15   12    9   16                                                  
CONECT   16   15    9                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

View in JSmol

Synonyms

Value	Source
trans-Sesquisabinene hydric acid	Generator

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3720 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

(2S,5S)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol

Traditional Name

(2S,5S)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol

CAS Registry Number

Not Available

SMILES

CC(CCC=C(C)C)[C@]12CC1[C@@](C)(O)CC2

InChI Identifier

InChI=1S/C15H26O/c1-11(2)6-5-7-12(3)15-9-8-14(4,16)13(15)10-15/h6,12-13,16H,5,7-10H2,1-4H3/t12?,13?,14-,15-/m0/s1

InChI Key

IRDFGGRWKUKANK-WUCCLRPBSA-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
Daucus carota	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquisabinane sesquiterpenoid
Sesquiterpenoid
Tertiary alcohol
Cyclic alcohol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Alcohol
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	3.55	ChemAxon
pKa (Strongest Acidic)	19.13	ChemAxon
pKa (Strongest Basic)	-0.99	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.36 m³·mol⁻¹	ChemAxon
Polarizability	28.01 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

C00053857

Chemspider ID

4933849

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6428444

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Noriega P, Ballesteros J, De la Cruz A, Veloz T: Chemical Composition and Preliminary Antimicrobial Activity of the Hydroxylated Sesquiterpenes in the Essential Oil from Piper barbatum Kunth Leaves. Plants (Basel). 2020 Feb 6;9(2):211. doi: 10.3390/plants9020211. [PubMed:32041311 ]
Chen Z, Quan L, Zhou H, Zhao Y, Chen P, Hu L, Yang Z, Hu C, Cao D: Screening of active fractions from Curcuma Longa Radix isolated by HPLC and GC-MS for promotion of blood circulation and relief of pain. J Ethnopharmacol. 2019 Apr 24;234:68-75. doi: 10.1016/j.jep.2018.09.035. Epub 2018 Sep 27. [PubMed:30268652 ]
Chen D, Du Z, Lin Z, Su P, Huang H, Ou Z, Pan W, Huang S, Zhang K, Zheng X, Lin L, Zhang L: The Chemical Compositions of Angelica pubescens Oil and Its Prevention of UV-B Radiation-Induced Cutaneous Photoaging. Chem Biodivers. 2018 Oct;15(10):e1800235. doi: 10.1002/cbdv.201800235. Epub 2018 Oct 7. [PubMed:29996001 ]
Swapna Sonale R, Ramalakshmi K, Udaya Sankar K: Characterization of Neem (Azadirachta indica A. Juss) seed volatile compounds obtained by supercritical carbon dioxide process. J Food Sci Technol. 2018 Apr;55(4):1444-1454. doi: 10.1007/s13197-018-3060-y. Epub 2018 Feb 3. [PubMed:29606759 ]
Benomari FZ, Djabou N, Medbouhi A, Khadir A, Bendahou M, Selles C, Desjobert JM, Costa J, Muselli A: Chemical Variability and Biological Activities of Essential Oils of Micromeria inodora (Desf.) Benth. from Algeria. Chem Biodivers. 2016 Nov;13(11):1559-1572. doi: 10.1002/cbdv.201600098. Epub 2016 Oct 27. [PubMed:27448034 ]
LOTUS database [Link]

Showing NP-Card for (2s,5s)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol (NP0269180)

MOL for NP0269180 ((2s,5s)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol)

3D MOL for NP0269180 ((2s,5s)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol)

3D SDF for NP0269180 ((2s,5s)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol)

3D-SDF for NP0269180 ((2s,5s)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol)

PDB for NP0269180 ((2s,5s)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol)

3D PDB for NP0269180 ((2s,5s)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol)

SMILES for NP0269180 ((2s,5s)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol)

INCHI for NP0269180 ((2s,5s)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol)

Structure for NP0269180 ((2s,5s)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol)

3D Structure for NP0269180 ((2s,5s)-2-methyl-5-(6-methylhept-5-en-2-yl)bicyclo[3.1.0]hexan-2-ol)