NP-MRD: Showing NP-Card for beta-Bisabolene (NP0044876)

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Record Information

Version

2.0

Created at

2022-03-10 18:37:03 UTC

Updated at

2022-03-10 22:18:24 UTC

NP-MRD ID

NP0044876

Secondary Accession Numbers

None

Natural Product Identification

Common Name

beta-Bisabolene

Description

Beta-Bisabolene is biochemically a sesquiterpenoid, comprised of three isoprene units. Sesquiterpenoids are terpenes that contain 15 carbon atoms. Beta-Bisabolene is an isoprenoid lipid molecule which is very hydrophobic, 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. Beta-Bisabolene has a balsamic odor. Bisabolenes are naturally occurring sesquiterpenoid found in the essential oils of bisabol from the shrub Commiphora guidottii, and in a wide variety of other plants including cubeb, lemon, oregano and in trace amounts in cannabis plants (PMID: 6991645 ). Beta-Bisabolene is also found in 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 by different insects such as stink bugs, fruit flies (PMID:11673844 ) And by several fungi (PMID: 25957494 ). Bisabolenes are intermediates in the biosynthesis of many other natural chemical compounds, including hernandulcin, a natural sweetener (PMID: 22867794 ) Which is approved as a food additive in Europe. Beta-Bisabolene has some medicinal properties. It had synergistic antibacterial activity with ampicillin against Staphylococcus aureus (PMID: 17235483 ) And was cytotoxic to breast cancer cell lines (PMID: 26666387 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 39  0  0  0  0  0  0  0  0999 V2000
    0.3151   -1.3671   -1.6339 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0409   -0.2141   -1.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9201    0.8929   -1.0038 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3537    0.5328   -1.2613 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8875   -0.4178   -0.2577 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9560   -0.0826    0.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5901    1.2338    0.2509 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4719   -1.0543    1.4646 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4071   -0.0235   -0.6092 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.4597    0.3080    0.8582 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8774    0.6549    1.1745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8998    0.2467    0.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2909    0.6495    0.8336 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7662   -0.5890   -0.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3422   -1.1525   -0.8859 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4040   -2.2023   -1.6923 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3032   -1.5636   -2.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8681    1.3226    0.0319 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6541    1.7493   -1.6924 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9817    1.4469   -1.2793 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4990    0.0714   -2.2656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4212   -1.3741   -0.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9511    1.3262   -0.7845 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4280    1.4108    0.9807 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8477    2.0397    0.4628 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0586   -2.0622    1.2636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1939   -0.6995    2.4741 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5780   -1.1470    1.3633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8262    0.8787   -1.1304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2368   -0.6092    1.4791 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8059    1.1423    1.1610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1219    1.2708    2.0498 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8124    1.0486   -0.0654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2675    1.4633    1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8198   -0.2560    1.1940 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9072    0.0514   -1.6762 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4762   -1.4360   -0.7925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2380   -1.9572   -0.1299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2793   -1.5325   -1.9303 H   0  0  0  0  0  0  0  0  0  0  0  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
  9  2  1  0
  2  1  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  2  3
  6  7  1  0
  6  8  1  0
 10  9  1  0
  9 29  1  6
 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
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
M  END

  Mrv1652307312018372D          

 16 16  0  0  1  0            999 V2000
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    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
    0.0000    0.0000    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
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    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
 10  8  1  0  0  0  0
 11  9  1  0  0  0  0
 12  1  1  0  0  0  0
 12  2  1  0  0  0  0
 12  6  2  0  0  0  0
 13  3  1  0  0  0  0
 13  8  2  0  0  0  0
 13  9  1  0  0  0  0
 14  4  2  0  0  0  0
 14  7  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 15 14  1  6  0  0  0
 15 16  1  1  0  0  0
M  END
> <DATABASE_ID>
NP0044876

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H][C@@]1(CCC(C)=CC1)C(=C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,15H,4-5,7,9-11H2,1-3H3/t15-/m1/s1

> <INCHI_KEY>
XZRVRYFILCSYSP-OAHLLOKOSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.836108479109953

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-1-methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohex-1-ene

> <ALOGPS_LOGP>
6.01

> <JCHEM_LOGP>
4.879526926666667

> <ALOGPS_LOGS>
-4.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
70.2829

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.41e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-β-bisabolene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 31-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   31-JUL-20         0                                  
HETATM    1  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5    6    7                                                       
CONECT    6    5   12                                                       
CONECT    7    5   14                                                       
CONECT    8   10   13                                                       
CONECT    9   11   13                                                       
CONECT   10    8   15                                                       
CONECT   11    9   15                                                       
CONECT   12    1    2    6                                                  
CONECT   13    3    8    9                                                  
CONECT   14    4    7   15                                                  
CONECT   15   10   11   14   16                                             
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

View in JSmol

Synonyms

Value	Source
(-)-beta-Bisabolene	ChEBI
(S)-(-)-6-Methyl-2-(4-methyl-3-cyclohexen-1-yl)-1,5-heptadiene	ChEBI
(S)-1-Methyl-4-(5-methyl-1-methylene-4-hexenyl)cyclohexene	ChEBI
beta-Bisabolene	ChEBI
L-beta-Bisabolene	ChEBI
(-)-b-Bisabolene	Generator
(-)-Β-bisabolene	Generator
b-Bisabolene	Generator
Β-bisabolene	Generator
L-b-Bisabolene	Generator
L-Β-bisabolene	Generator
(S)-b-Bisabolene	Generator
(S)-Β-bisabolene	Generator

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(4S)-1-methyl-4-(6-methylhepta-1,5-dien-2-yl)cyclohex-1-ene

Traditional Name

(-)-β-bisabolene

CAS Registry Number

495-61-4

SMILES

[H][C@@]1(CCC(C)=CC1)C(=C)CCC=C(C)C

InChI Identifier

InChI=1S/C15H24/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8,15H,4-5,7,9-11H2,1-3H3/t15-/m1/s1

InChI Key

XZRVRYFILCSYSP-OAHLLOKOSA-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 alba	LOTUS Database	35616633
Abies nordmanniana	LOTUS Database	35616633
Abies sibirica	LOTUS Database	35616633
Achillea grandifolia	LOTUS Database	35616633
Achillea nana	LOTUS Database	35616633
Aframomum angustifolium	LOTUS Database	35616633
Ageratina adenophora	Plant	KNApSAcK
Ageratum conyzoides	LOTUS Database	35616633
Aloysia gratissima	LOTUS Database	35616633
Alphinia galanga	-	KNApSAcK
Alpinia chinensis	LOTUS Database	35616633
Alpinia conchigera	LOTUS Database	35616633
Alpinia galanga	LOTUS Database	35616633
Alpinia latilabris	LOTUS Database	35616633
Alpinia mutica	LOTUS Database	35616633
Ambrosia artemisiifolia	Plant	KNApSAcK
Ambrosia trifida	Plant	KNApSAcK
Angelica archangelica	LOTUS Database	35616633
Anthemis aciphylla	LOTUS Database	35616633
Anthemis aciphylla BOISS.var.discoidea BOISS	Plant	KNApSAcK
Arabidopsis thaliana	Plant	KNApSAcK
Asarum asperum	LOTUS Database	35616633
Asarum epigynum	LOTUS Database	35616633
Aster scaber	LOTUS Database	35616633
Atalantia buxifolia	LOTUS Database	35616633
Avena fatua	LOTUS Database	35616633
Callitropsis nootkatensis	LOTUS Database	35616633
Cannabis sativa	NULL	Not Available
Cantinoa mutabilis	LOTUS Database	35616633
Carica papaya L.	Plant	KNApSAcK
Centaurea armena	Plant	KNApSAcK
Centaurea sessilis	Plant	KNApSAcK
Centella asiatica	LOTUS Database	35616633
Chromolaena laevigata	LOTUS Database	35616633
Cinnamomum parthenoxylon	LOTUS Database	35616633
Cinnamomum sieboldii	LOTUS Database	35616633
Cistus albidus	Plant	KNApSAcK
Citrus aurantiifolia	Plant	KNApSAcK
Citrus aurantium	LOTUS Database	35616633
Citrus bergamia	Plant	KNApSAcK
Citrus hystrix	Plant	KNApSAcK
Citrus latifolia	Plant	KNApSAcK
Citrus limettioides	Plant	KNApSAcK
Citrus limon	Plant	KNApSAcK
Citrus medica	LOTUS Database	35616633
Citrus paradisi	Plant	KNApSAcK
Citrus reticulata	Plant	KNApSAcK
Citrus X sinensis (L.) Osbeck (pro. sp.)	Plant	KNApSAcK
Clinopodium grandiflorum	LOTUS Database	35616633
Cochlospermum tinctorium	LOTUS Database	35616633
Commiphora africana	LOTUS Database	35616633
Copaifera duckei	Plant	KNApSAcK
Copaifera guianensis	Plant	KNApSAcK
Copaifera paupera	LOTUS Database	35616633
Cryptomeria japonica	LOTUS Database	35616633
Curcuma aeruginosa	Plant	KNApSAcK
Curcuma longa	Plant	KNApSAcK
Curcuma phaeocaulis	Plant	KNApSAcK
Curcuma pierreana	LOTUS Database	35616633
Cymbopogon martinii	LOTUS Database	35616633
Daucus carota	Plant	KNApSAcK
Elsholtzia ciliata	LOTUS Database	35616633
Encelia canescens	LOTUS Database	35616633
Eremanthus arboreus	LOTUS Database	35616633
Eryngium foetidum	LOTUS Database	35616633
Eupatorium cannabinum	LOTUS Database	35616633
Eupatorium capillifolium	LOTUS Database	35616633
Ferulago thirkeana	LOTUS Database	35616633
Frullania deplanata	Plant	KNApSAcK
Frullania probosciphora	Plant	KNApSAcK
Ganoderma lucidum	Fungi	KNApSAcK
Guatteriopsis blepharophylla	Plant	KNApSAcK
Hamamelis virginiana	LOTUS Database	35616633
Hedychium spicatum	LOTUS Database	35616633
Helianthus tuberosus	LOTUS Database	35616633
Helichrysum argyrophyllum	LOTUS Database	35616633
Helichrysum italicum	LOTUS Database	35616633
Jamesoniella autumnalis	LOTUS Database	35616633
Juniperus comitana	LOTUS Database	35616633
Lantana camara	LOTUS Database	35616633
Lavandula angustifolia	Plant	KNApSAcK
Lavandula canarien-sis	Plant	KNApSAcK
Lavandula latifolia	LOTUS Database	35616633
Lavandula multifida	Plant	KNApSAcK
Lepechinia chamaedryoides	LOTUS Database	35616633
Leptospermum scoparium	Plant	KNApSAcK
Ligularia altaica	LOTUS Database	35616633
Lippia nodiflora	LOTUS Database	35616633
Litsea cubeba	Plant	KNApSAcK
Metacalypogeia alternifolia	LOTUS Database	35616633
Metacalypogeia cordifolia	LOTUS Database	35616633
Mosla cavaleriei	LOTUS Database	35616633
Murraya paniculata	Plant	KNApSAcK
Myrrhis odorata	LOTUS Database	35616633
Myrtus communis	LOTUS Database	35616633
Nepeta nuda	LOTUS Database	35616633
Nepeta racemosa	LOTUS Database	35616633
Ocimum basilicum	Plant	KNApSAcK
Ocimum gratissimum	LOTUS Database	35616633
Ocimum selloi	LOTUS Database	35616633
Origanum cordifolium	LOTUS Database	35616633
Origanum majorana	LOTUS Database	35616633
Origanum onites	LOTUS Database	35616633
Origanum vulgare	Plant	KNApSAcK
Osyris quadripartita	LOTUS Database	35616633
Osyris tenuifolia	Plant	KNApSAcK
Panax ginseng	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Persea americana	LOTUS Database	35616633
Petasites albus	Plant	KNApSAcK
Petasites hybridus	Plant	KNApSAcK
Petroselinum crispum	Plant	KNApSAcK
Phyla dulcis	LOTUS Database	35616633
Picea glehnii	LOTUS Database	35616633
Picea koraiensis	LOTUS Database	35616633
Pimpinella anisum	LOTUS Database	35616633
Pinus massoniana	LOTUS Database	35616633
Pinus sibirica	Plant	KNApSAcK
Piper auritum	LOTUS Database	35616633
Piper guineense	LOTUS Database	35616633
Piper nigrum L.	Plant	KNApSAcK
Piper obliquum	Plant	KNApSAcK
Polygala senega	LOTUS Database	35616633
Polygonum minus	Plant	KNApSAcK
Porella vernicosa	LOTUS Database	35616633
Prangos heyniae	LOTUS Database	35616633
Psidium guajava	Plant	KNApSAcK
Pterocaulon virgatum	LOTUS Database	35616633
Rattus rattus	LOTUS Database	35616633
Rhaponticum carthamoides	Plant	KNApSAcK
Rhododendron mucronulatum	LOTUS Database	35616633
Salvia fruticosa	LOTUS Database	35616633
Salvia hydrangea	LOTUS Database	35616633
Salvia rosmarinus	Plant	KNApSAcK
Santalum spicatum	LOTUS Database	35616633
Satureja spicigera	LOTUS Database	35616633
Senecio squalidus	LOTUS Database	35616633
Senecio vulgaris	Plant	KNApSAcK
Sideritis romana	LOTUS Database	35616633
Silphium asteriscus	LOTUS Database	35616633
Smallanthus uvedalia	LOTUS Database	35616633
Solanum tuberosum	LOTUS Database	35616633
Solidago canadensis	LOTUS Database	35616633
Spondias mombin	LOTUS Database	35616633
Swertia japonica	LOTUS Database	35616633
Teucrium scorodonia	LOTUS Database	35616633
Thymbra spicata	LOTUS Database	35616633
Thymus kotschyanus	LOTUS Database	35616633
Thymus longicaulis	LOTUS Database	35616633
Thymus marschallianus	LOTUS Database	35616633
Thymus quinquecostatus	LOTUS Database	35616633
Thymus vulgaris	Plant	KNApSAcK
Tilesia baccata	LOTUS Database	35616633
Trachyspermum anethifolium	LOTUS Database	35616633
Tussilago farfara	LOTUS Database	35616633
Umbellularia californica	LOTUS Database	35616633
Valeriana officinalis	LOTUS Database	35616633
Vitex negundo	LOTUS Database	35616633
Wettsteinia schusteriana	LOTUS Database	35616633
Widdringtonia whytei	LOTUS Database	35616633
Zingiber montanum	Plant	KNApSAcK
Zingiber officinale	FooDB	PHYTOHUB
Zingiber zerumbet	LOTUS Database	35616633
Ziziphus jujuba	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

beta-bisabolene (CHEBI:49263 )
Bisabolane sesquiterpenoids (C16775 )
Bisabolanes (C16775 )
Bisabolane sesquiterpenoids (LMPR0103060013 )

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	6.01	ALOGPS
logP	4.88	ChemAxon
logS	-4.4	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	70.28 m³·mol⁻¹	ChemAxon
Polarizability	26.84 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

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00007242

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bisabolene

METLIN ID

Not Available

PubChem Compound

10104370

PDB ID

Not Available

ChEBI ID

49263

Good Scents ID

Not Available

References

General References

Lu F, Teal PE: Sex pheromone components in oral secretions and crop of male Caribbean fruit flies, Anastrepha suspensa (Loew). Arch Insect Biochem Physiol. 2001 Nov;48(3):144-54. doi: 10.1002/arch.1067. [PubMed:11673844 ]
Nascimento AM, Brandao MG, Oliveira GB, Fortes IC, Chartone-Souza E: Synergistic bactericidal activity of Eremanthus erythropappus oil or beta-bisabolene with ampicillin against Staphylococcus aureus. Antonie Van Leeuwenhoek. 2007 Jul;92(1):95-100. doi: 10.1007/s10482-006-9139-x. Epub 2007 Jan 18. [PubMed:17235483 ]
Yeo SK, Ali AY, Hayward OA, Turnham D, Jackson T, Bowen ID, Clarkson R: beta-Bisabolene, a Sesquiterpene from the Essential Oil Extract of Opoponax (Commiphora guidottii), Exhibits Cytotoxicity in Breast Cancer Cell Lines. Phytother Res. 2016 Mar;30(3):418-25. doi: 10.1002/ptr.5543. Epub 2015 Dec 15. [PubMed:26666387 ]

Showing NP-Card for beta-Bisabolene (NP0044876)

MOL for NP0044876 (beta-Bisabolene)

3D MOL for NP0044876 (beta-Bisabolene)

3D SDF for NP0044876 (beta-Bisabolene)

3D-SDF for NP0044876 (beta-Bisabolene)

PDB for NP0044876 (beta-Bisabolene)

3D PDB for NP0044876 (beta-Bisabolene)

SMILES for NP0044876 (beta-Bisabolene)

INCHI for NP0044876 (beta-Bisabolene)

Structure for NP0044876 (beta-Bisabolene)

3D Structure for NP0044876 (beta-Bisabolene)