NP-MRD: Showing NP-Card for Cis-gamma-Bisabolene (NP0045062)

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Record Information

Version

2.0

Created at

2022-03-10 18:57:20 UTC

Updated at

2022-03-10 22:19:51 UTC

NP-MRD ID

NP0045062

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Cis-gamma-Bisabolene

Description

Cis-gamma-Bisabolene is an isomer of Bisabolene. Three isomers are known, alpha-, beta-, and gamma-bisabolene, which differ by the positions of the double bonds. Bisabolenes are a group of closely related natural chemical compounds which are classified as sesquiterpenes. Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes that contain 15 carbon atoms and are comprised of three isoprene units. The biosynthesis of sesquiterpenes is known to occur mainly through the mevalonic acid pathway (MVA), in the cytosol. However, recent studies have found evidence of pathway crosstalk with the methyl-eritritol-phosphate (MEP) pathway in the plastid (PMID: 19932496 , 17710406 ) Farnesyl diphosphate (FPP) is a key intermediate in the biosynthesis of cyclic sesquiterpenes. FPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Bisabolenes are present in the essential oils of German chamomile (PMID: 22096322 ), And of a wide variety of other plants including cubeb, lemon, oregano, and Cannabis sativa (PMID: 6991645 , 26657499 ). Cis-gamma-Bisabolene is also a constituent of cannabis smoke and is volatilized during the combustion of cannabis (https://Doi.Org/10.1007/978-1-59259-947-9_2). Various derivates of bisabolol also function as pheromones in different insects (PMID: 31659569 ). Bisabolenes are produced by several fungi, though their biological role in that group of organisms remains unclear (doi:10.3390/F11030290).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    4.6094    0.0169   -0.6341 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1826    0.8102    0.5396 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1367    1.7574    1.1529 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9785    0.6919    1.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9975   -0.2373    0.4693 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7430    0.5096   -0.0085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2439   -0.4104   -0.5876 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0921   -1.2391   -1.7724 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4445   -0.4847   -0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4182   -1.4392   -0.6645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7811   -0.7821   -0.6160 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1515   -0.1975    0.5115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4530    0.4712    0.6701 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2018   -0.2303    1.6452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8758    0.2814    1.1347 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6883    0.1184   -0.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0663    0.3181   -1.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4270   -1.0492   -0.3931 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0072    1.6710    2.2668 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1785    1.3863    0.9475 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0105    2.7998    0.8096 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6939    1.2838    1.9044 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6940   -0.9482    1.2796 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3837   -0.8527   -0.3496 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0887    1.2010   -0.8340 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4039    1.0824    0.8646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2390   -2.2922   -1.5591 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4225   -0.9034   -2.6967 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1577   -1.2778   -1.9880 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1738   -1.6636   -1.7014 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4586   -2.3217    0.0058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4138   -0.8043   -1.4919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9514    0.6893   -0.2999 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3248    1.4446    1.2038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1536   -0.1166    1.3305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5633    0.3411    2.5240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0751   -1.3118    1.9167 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1333    0.3489    1.9503 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0607    1.3388    0.8059 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  1  0
 12 11  2  0
 11 10  1  0
 10  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
 15 38  1  0
 15 39  1  0
 14 36  1  0
 14 37  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 11 32  1  0
 10 30  1  0
 10 31  1  0
M  END

  Mrv1652303202019022D          

 15 15  0  0  0  0            999 V2000
    1.7734    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0309    0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0309   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3709   -1.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709    0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3709   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1133   -1.0305    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734   -0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7734    0.2055    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5159    0.6180    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0309    1.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7734    1.4430    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5159    1.8555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 14  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4  8  2  0  0  0  0
  6  7  1  0  0  0  0
  6 11  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045062

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C1/CCC(C)=CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8H,5,7,9-11H2,1-4H3/b15-14-

> <INCHI_KEY>
XBGUIVFBMBVUEG-PFONDFGASA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.868979322773733

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4E)-1-methyl-4-(6-methylhept-5-en-2-ylidene)cyclohex-1-ene

> <ALOGPS_LOGP>
5.88

> <JCHEM_LOGP>
4.777935431666666

> <ALOGPS_LOGS>
-3.55

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
71.08879999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.82e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(E)-gamma-bisabolene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         0                                  
HETATM    1  C   UNK     0       3.310   1.154   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.924   0.384   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.924  -1.154   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.692  -1.924   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.692  -3.464   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.078   1.154   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.692   0.384   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.692  -1.154   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.078  -1.924   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -3.310  -1.154   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.310   0.384   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.696   1.154   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.924   3.464   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.310   2.694   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.696   3.464   0.000  0.00  0.00           C+0
CONECT    1    2   14                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5    8                                                  
CONECT    5    4                                                            
CONECT    6    7   11                                                       
CONECT    7    6    8                                                       
CONECT    8    4    7    9                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11    6   10   12                                                  
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14    1   13   15                                                  
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Value	Source
(Z)-Laquo gammaraquo -bisabolene	HMDB
(e)-g-Bisabolene	Generator
(e)-Γ-bisabolene	Generator

Chemical Formula

C₁₅H₂₄

Average Mass

204.3511 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(4E)-1-methyl-4-(6-methylhept-5-en-2-ylidene)cyclohex-1-ene

Traditional Name

(E)-gamma-bisabolene

CAS Registry Number

13062-00-5

SMILES

CC(C)=CCC\C(C)=C1/CCC(C)=CC1

InChI Identifier

InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8H,5,7,9-11H2,1-4H3/b15-14-

InChI Key

XBGUIVFBMBVUEG-PFONDFGASA-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, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, 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
Ayapana amygdalina	LOTUS Database	35616633
Cannabis sativa	NULL	Not Available
Helichrysum mimetes	LOTUS Database	35616633
Larix gmelini	LOTUS Database	35616633
Laurencia nipponica	LOTUS Database	35616633
Molopospermum peloponnesiacum	LOTUS Database	35616633
Symphyopappus reticulatus	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

Bisabolane sesquiterpenoid
Sesquiterpenoid
Branched unsaturated hydrocarbon
Cycloalkene
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

gamma-bisabolene (CHEBI:49239 )
Bisabolane sesquiterpenoids (LMPR0103060005 )

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	5.88	ALOGPS
logP	4.78	ChemAxon
logS	-3.6	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	71.09 m³·mol⁻¹	ChemAxon
Polarizability	26.87 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon