NP-MRD: Showing NP-Card for trans-gamma-Bisabolene (NP0045054)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-10 18:57:11 UTC

Updated at

2022-03-10 22:22:41 UTC

NP-MRD ID

NP0045054

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trans-gamma-Bisabolene

Description

Trans-gamma-Bisabolene or (E)-gamma-bisabolene is biochemically a sesquiterpenoid. Sesquiterpenoids 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. 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. Beta-Bisabolene is considered to be an isoprenoid lipid molecule, as such, Beta-Bisabolene is a very hydrophobic molecule, practically insoluble in water and relatively neutral. Bisabolene has three isomers (alpha-, beta-, and gamma-bisabolene) which differ by the positions of the double bonds. Bisabolenes are naturally occurring sesquiterpenoid found in the essential oils of bisabol, and of a wide variety of other plants including cubeb, lemon, oregano and found in trace amounts in cannabis plants (PMID: 6991645 ). Trans-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). Bisabolenes are also produced in different insects such as stink bugs, fruit flies and by several fungi (PMID: 11673844 ; PMID: 25957494 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
   -4.8064    0.3063   -1.0574 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0959   -0.5813   -0.0957 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8866   -1.2848    0.9426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7855   -0.7629   -0.1366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9008   -0.1255   -1.1115 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8661    0.8028   -0.5915 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1023    0.2363    0.3584 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2522   -0.2155    1.7150 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3907    0.1556   -0.0271 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7749    0.6451   -1.3855 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2270    0.4166   -1.5740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1040    0.3656   -0.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5367    0.1358   -0.8469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6203    0.5459    0.7962 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4137   -0.4084    0.8865 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8958   -0.1683   -2.0635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8249    0.5560   -0.6983 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2876    1.3042   -1.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8412   -1.6944    0.5414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0753   -0.5664    1.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3135   -2.1636    1.3070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3465   -1.4344    0.5874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3858   -0.8770   -1.7759 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5449    0.4766   -1.8124 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3618    1.6784   -0.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3199    1.2265   -1.4567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3003    0.1740    1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2942   -1.2935    1.8160 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4192    0.2211    2.5181 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2218    0.1119   -2.1846 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6390    1.7563   -1.4608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6044    0.2786   -2.6128 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9995   -0.5748   -0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1390    1.0781   -0.7699 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7191   -0.3166   -1.8637 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2307    1.5950    0.8617 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3702    0.3217    1.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1105   -0.5661    1.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7621   -1.3550    0.3858 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


  Mrv1652309272007422D          

 15 15  0  0  0  0            999 V2000
 9999.629310000.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.3439 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.057110000.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.7723 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.485510000.4122    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.1987 9999.9999    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.485510001.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.629310001.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.7712 9998.7632    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.200610000.4131    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.486110000.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.4861 9999.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.2006 9998.7631    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.9151 9999.1755    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.915110000.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
 10 11  1  0  0  0  0
 10 15  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 12  9  1  0  0  0  0
  1 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0045054

> <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-CCEZHUSRSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.937897140633964

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4Z)-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>
(Z)-gamma-bisabolene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0    8665.9758667.436   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8667.3098666.666   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8668.6408667.436   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8669.9758666.666   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8671.3068667.436   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8672.6388666.666   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8671.3068668.975   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8665.9758668.975   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8660.6408664.358   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8663.3088667.438   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8661.9748666.668   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8661.9748665.128   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8663.3088664.358   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8664.6428665.128   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8664.6428666.668   0.000  0.00  0.00           C+0
CONECT    1    2    8   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    7                                                  
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8    1                                                            
CONECT    9   12                                                            
CONECT   10   11   15                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13    9                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   10   14    1                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

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

Traditional Name

(Z)-gamma-bisabolene

CAS Registry Number

11003-31-9

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-CCEZHUSRSA-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
Abies sibirica	LOTUS Database	35616633
Aframomum melegueta	LOTUS Database	35616633
Ajuga chamaepitys	LOTUS Database	35616633
Andrographis paniculata	LOTUS Database	35616633
Artemisia herba-alba	LOTUS Database	35616633
Artemisia xerophytica	LOTUS Database	35616633
Asarum trigynum	LOTUS Database	35616633
Asarum yakusimense	LOTUS Database	35616633
Atalantia buxifolia	LOTUS Database	35616633
Ayapana amygdalina	Plant	KNApSAcK
Baccharis salicifolia	LOTUS Database	35616633
Calypogeia suecica	LOTUS Database	35616633
Cananga odorata	LOTUS Database	35616633
Cannabis sativa	NULL	Not Available
Cephaelis ipecacuanha	LOTUS Database	35616633
Citrus aurantium	LOTUS Database	35616633
Citrus medica	LOTUS Database	35616633
Commiphora africana	LOTUS Database	35616633
Croton sarcopetalus	LOTUS Database	35616633
Curcuma longa	LOTUS Database	35616633
Cymbopogon martinii	LOTUS Database	35616633
Daucus carota	LOTUS Database	35616633
Dumortiera hirsuta	LOTUS Database	35616633
Erigeron philadelphicus	LOTUS Database	35616633
Eucalyptus sideroxylon	LOTUS Database	35616633
Geigeria burkei	LOTUS Database	35616633
Geigeria rigida	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Grindelia hirsutula	LOTUS Database	35616633
Hamamelis virginiana	LOTUS Database	35616633
Haplopappus glutinosus	LOTUS Database	35616633
Helichrysum argyrophyllum	LOTUS Database	35616633
Helichrysum mimetes	LOTUS Database	35616633
Heracleum dissectum	LOTUS Database	35616633
Humulus lupulus	LOTUS Database	35616633
Juniperus rigida	LOTUS Database	35616633
Lantana camara	LOTUS Database	35616633
Larix gmelini	LOTUS Database	35616633
Larix sibirica	LOTUS Database	35616633
Laurencia sp.	-	KNApSAcK
Lavandula angustifolia	LOTUS Database	35616633
Oedera squarrosa	LOTUS Database	35616633
Origanum dictamnus	LOTUS Database	35616633
Osyris quadripartita	LOTUS Database	35616633
Picea rubens	LOTUS Database	35616633
Pimpinella major	LOTUS Database	35616633
Pinus sibirica	LOTUS Database	35616633
Piper nigrum L.	Plant	KNApSAcK
Rhododendron dauricum	LOTUS Database	35616633
Rugelia nudicaulis	LOTUS Database	35616633
Salvia fruticosa	LOTUS Database	35616633
Santalum spicatum	LOTUS Database	35616633
Santolina rosmarinifolia	LOTUS Database	35616633
Solanum agrimoniifolium	LOTUS Database	35616633
Stevia eupatoria	LOTUS Database	35616633
Stevia rebaudiana	LOTUS Database	35616633
Zingiber officinale	LOTUS Database	35616633

Chemical Taxonomy

Classification

Not classified

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	26.94 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

External Links

Not Available

References

General References

Showing NP-Card for trans-gamma-Bisabolene (NP0045054)

MOL for NP0045054 (trans-gamma-Bisabolene)

3D MOL for NP0045054 (trans-gamma-Bisabolene)

3D SDF for NP0045054 (trans-gamma-Bisabolene)

3D-SDF for NP0045054 (trans-gamma-Bisabolene)

PDB for NP0045054 (trans-gamma-Bisabolene)

3D PDB for NP0045054 (trans-gamma-Bisabolene)

SMILES for NP0045054 (trans-gamma-Bisabolene)

INCHI for NP0045054 (trans-gamma-Bisabolene)

Structure for NP0045054 (trans-gamma-Bisabolene)

3D Structure for NP0045054 (trans-gamma-Bisabolene)