NP-MRD: Showing NP-Card for (E)-Beta-Farnesene (NP0045030)

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Record Information

Version

2.0

Created at

2022-03-10 18:53:01 UTC

Updated at

2022-03-10 22:22:40 UTC

NP-MRD ID

NP0045030

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(E)-Beta-Farnesene

Description

(E)-Beta-Farnesene, also known as EBF or trans-beta-Farnesene¬¨‚Ä†, belongs to the class of organic compounds known as sesquiterpenoids. Sesquiterpenes 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-erythritol-phosphate (MEP) pathway in the cytosol. The term farnesene refers to a set of six closely related chemical compounds (4 alpha-Farnesenes and 2 Beta-Farnesenes) which all are sesquiterpenes. Alpha-Farnesene and beta-Farnesene are isomers, differing by the location of one double bond. Beta-Farnesene is 7,11-dimethyl-3-methylene-1,6,10-dodecatriene while¬¨‚Ä†alpha-Farnesene is 3,7,11-trimethyl-1,3,6,10-dodecatetraene. The beta isomer exists as two stereoisomers (cis and trans) about the geometry of its central double bond. However, only the trans isomer exists in nature. Beta-Farnesene exists as a clear colorless liquid and is a hydrophobic, neutral compound that is insoluble in water. It has a woody, sweet, citrus aroma and is used as a masking or perfuming agent. Beta-Farnesene is found naturally in many plants and plant essential oils including basil, blood orange, carrots, celery, ginger, grapefruit, lavender, mint, orange peel, parsley, peppermint, pine, rosemary and thyme. It is one of several sesquiterpenes that are found in cannabis plants (PMID: 6991645 ).¬¨‚Ä†It 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).¬¨‚Ä†Beta-Farnesene is also released by aphids as an alarm pheremone upon death to warn away other aphids (PMID: 21092302 )

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 38  0  0  0  0  0  0  0  0999 V2000
   -5.3683    1.7191    0.5426 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4422    0.4246    0.3208 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4260   -0.4076   -0.2607 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6409   -1.6959   -0.4494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1297    0.1454   -0.6761 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3182    0.4561    0.5576 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9922    1.0426    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1059    0.4089    0.5940 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0235   -0.8479    1.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4508    0.9598    0.2667 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1637   -0.1046   -0.5772 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5005    0.4479   -0.9001 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5680   -0.2109   -0.4978 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9298    0.3491   -0.8251 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4436   -1.4801    0.2630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2131    2.2558    0.9982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5396    2.3431    0.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3910   -0.0672    0.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9157   -2.3625   -0.8918 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5855   -2.1455   -0.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5585   -0.5645   -1.3230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2645    1.0754   -1.2910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1731   -0.5174    1.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9115    1.0776    1.2350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9280    1.9675   -0.3477 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5018   -1.6651    0.7684 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9984   -1.2377    1.6181 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5413   -0.7222    2.3290 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3464    1.8767   -0.3476 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0440    1.2194    1.1470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2033   -1.0590   -0.0451 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6051   -0.1916   -1.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5481    1.3710   -1.4537 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9519    1.4061   -0.4821 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9529    0.4016   -1.9477 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7238   -0.2656   -0.4040 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8100   -1.3636    1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0600   -2.2792   -0.4051 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4584   -1.7592    0.6608 H   0  0  0  0  0  0  0  0  0  0  0  0
 14 13  1  0
 13 15  1  0
 13 12  2  3
 12 11  1  0
 11 10  1  0
 10  8  1  0
  8  9  1  0
  8  7  2  0
  7  6  1  0
  6  5  1  0
  5  3  1  0
  3  4  2  3
  3  2  1  0
  2  1  2  3
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 12 33  1  0
 11 31  1  0
 11 32  1  0
 10 29  1  0
 10 30  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
  7 25  1  0
  6 23  1  0
  6 24  1  0
  5 21  1  0
  5 22  1  0
  4 19  1  0
  4 20  1  0
  2 18  1  0
  1 16  1  0
  1 17  1  0
M  END


  Mrv1652309272007292D          

 15 14  0  0  0  0            999 V2000
   -0.2858    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4287   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0003   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2858    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1432    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7147    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8576   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4291   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1437    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2866   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8581   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1437    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0010    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
  1  4  1  0  0  0  0
  2  5  1  0  0  0  0
  3  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  9  1  0  0  0  0
  8 10  2  0  0  0  0
  9 11  1  0  0  0  0
  9 12  2  0  0  0  0
 10 13  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  2  0  0  0  0
M  END
> <DATABASE_ID>
NP0045030

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCC\C(C)=C\CCC(=C)C=C

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

> <INCHI_KEY>
JSNRRGGBADWTMC-NTCAYCPXSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.893005093461404

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(6E)-7,11-dimethyl-3-methylidenedodeca-1,6,10-triene

> <ALOGPS_LOGP>
5.70

> <JCHEM_LOGP>
5.196814411666667

> <ALOGPS_LOGS>
-4.78

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
72.18159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
3.38e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
β-farnesene

> <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      -0.533   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.800  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.867  -0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.533   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.134   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.201   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       3.468  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.534  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.801   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -5.868   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.135  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.801   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -7.202  -0.770   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -5.868   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       7.469   0.000   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5                                                       
CONECT    3    1    6                                                       
CONECT    4    1                                                            
CONECT    5    2    7                                                       
CONECT    6    3    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11   12                                                  
CONECT   10    8   13   14                                                  
CONECT   11    9   15                                                       
CONECT   12    9                                                            
CONECT   13   10                                                            
CONECT   14   10                                                            
CONECT   15   11                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
(6E)-7,11-Dimethyl-3-methylene-1,6,10-dodecatriene	ChEBI
(e)-7,11-Dimethyl-3-methylenedodeca-1,6,10-triene	ChEBI
beta-Farnesene	ChEBI
beta-trans-Farnesene	ChEBI
trans-7,11-Dimethyl-3-methylene-1,6,10-dodecatriene	ChEBI
b-Farnesene	Generator
Β-farnesene	Generator
b-trans-Farnesene	Generator
Β-trans-farnesene	Generator
(e)-b-Farnesene	Generator
(e)-Β-farnesene	Generator
(E)-beta-Farnesene	ChEBI, KEGG
trans-b-Farnesene	Generator
trans-β-Farnesene	Generator
(E)-7,11-Dimethyl-3-methylene-1,6,10-dodecatriene	PhytoBank
trans-beta-Farnesene	PhytoBank

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(6E)-7,11-dimethyl-3-methylidenedodeca-1,6,10-triene

Traditional Name

β-farnesene

CAS Registry Number

18452-58-9

SMILES

CC(C)=CCC\C(C)=C\CCC(=C)C=C

InChI Identifier

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

InChI Key

JSNRRGGBADWTMC-NTCAYCPXSA-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
Acca sellowiana	LOTUS Database	35616633
Achillea millefolium	LOTUS Database	35616633
Achyrospermum africanum	LOTUS Database	35616633
Acorus calamus	LOTUS Database	35616633
Alpinia zerumbet	LOTUS Database	35616633
Ambrosia trifida	LOTUS Database	35616633
Anthriscus sylvestris	LOTUS Database	35616633
Antidorcas marsupialis	LOTUS Database	35616633
Artemisia annua	LOTUS Database	35616633
Artemisia herba-alba	LOTUS Database	35616633
Artemisia pontica	LOTUS Database	35616633
Artemisia vulgaris	LOTUS Database	35616633
Asarum megacalyx	LOTUS Database	35616633
Aspergillus candidus	LOTUS Database	35616633
Aster scaber	LOTUS Database	35616633
Athamanta macedonica	LOTUS Database	35616633
Bedfordia arborescens	LOTUS Database	35616633
Blumea mollis	LOTUS Database	35616633
Callitropsis nootkatensis	LOTUS Database	35616633
Canella winterana	LOTUS Database	35616633
Cannabis sativa	NULL	Not Available
Centaurea solstitialis	LOTUS Database	35616633
Centella asiatica	LOTUS Database	35616633
Chengiopanax sciadophylloides	LOTUS Database	35616633
Citrus limon	LOTUS Database	35616633
Citrus maxima	LOTUS Database	35616633
Citrus reticulata	LOTUS Database	35616633
Cleistopholis patens	LOTUS Database	35616633
Conyza sumatrensis	LOTUS Database	35616633
Croton jacobinensis	LOTUS Database	35616633
Curcuma zedoaria	LOTUS Database	35616633
Cylindrocolea recurvifolia	LOTUS Database	35616633
Dasystenella acanthina	LOTUS Database	35616633
Daucus carota	LOTUS Database	35616633
Dipteryx lacunifera	LOTUS Database	35616633
Duhaldea cuspidata	LOTUS Database	35616633
Erigeron canadensis	LOTUS Database	35616633
Erigeron philadelphicus	LOTUS Database	35616633
Eryngium foetidum	LOTUS Database	35616633
Eupatorium capillifolium	LOTUS Database	35616633
Frullania pycnantha	LOTUS Database	35616633
Gossypium hirsutum	LOTUS Database	35616633
Grindelia camporum	LOTUS Database	35616633
Hamamelis virginiana	LOTUS Database	35616633
Hedychium spicatum	LOTUS Database	35616633
Helichrysum cephaloideum	LOTUS Database	35616633
Helichrysum chrysargyrum	LOTUS Database	35616633
Helichrysum cymosum	LOTUS Database	35616633
Hippia frutescens	LOTUS Database	35616633
Houttuynia cordata	LOTUS Database	35616633
Humulus lupulus	LOTUS Database	35616633
Isocoma tenuisecta	LOTUS Database	35616633
Juglans regia	LOTUS Database	35616633
Larix gmelini	LOTUS Database	35616633
Marrubium parviflorum	LOTUS Database	35616633
Marrubium peregrinum	LOTUS Database	35616633
Matricaria chamomilla	LOTUS Database	35616633
Matricaria discoidea	LOTUS Database	35616633
Matricaria matricarioides	LOTUS Database	35616633
Mentha piperita	LOTUS Database	35616633
Mentha rotundifolia	LOTUS Database	35616633
Microglossa pyrifolia	LOTUS Database	35616633
Micromeria sinaica	LOTUS Database	35616633
Monardella hypoleuca	LOTUS Database	35616633
Mosla cavaleriei	LOTUS Database	35616633
Mosla chinensis	LOTUS Database	35616633
Nepeta cataria	LOTUS Database	35616633
Nepeta nepetella	LOTUS Database	35616633
Nicotiana alata	LOTUS Database	35616633
Ocimum gratissimum	LOTUS Database	35616633
Origanum laevigatum	LOTUS Database	35616633
Origanum onites	LOTUS Database	35616633
Paeonia lactiflora	LOTUS Database	35616633
Paleosuchus trigonatus	LOTUS Database	35616633
Panax ginseng	LOTUS Database	35616633
Pelargonium endlicherianum	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Persicaria minor	LOTUS Database	35616633
Peucedanum zenkeri	LOTUS Database	35616633
Phyla dulcis	LOTUS Database	35616633
Picradeniopsis multiflora	LOTUS Database	35616633
Pimpinella anisum	LOTUS Database	35616633
Pinus koraiensis	LOTUS Database	35616633
Pinus merkusii	LOTUS Database	35616633
Pinus pinaster	LOTUS Database	35616633
Piper arboreum	LOTUS Database	35616633
Piper guineense	LOTUS Database	35616633
Ptychopetalum olacoides	LOTUS Database	35616633
Pycnanthemum floridanum	LOTUS Database	35616633
Radula javanica	LOTUS Database	35616633
Radula kojana	LOTUS Database	35616633
Rhaponticum carthamoides	LOTUS Database	35616633
Rhododendron groenlandicum	LOTUS Database	35616633
Rhododendron mucronulatum	LOTUS Database	35616633
Roldana aschenborniana	LOTUS Database	35616633
Rugelia nudicaulis	LOTUS Database	35616633
Salvia tomentosa	LOTUS Database	35616633
Sassafras albidum	LOTUS Database	35616633
Schefflera arboricola	LOTUS Database	35616633
Senecio inaequidens	LOTUS Database	35616633
Senecio lydenburgensis	LOTUS Database	35616633
Senecio nebrodensis	LOTUS Database	35616633
Sideritis montana	LOTUS Database	35616633
Sideritis tragoriganum	LOTUS Database	35616633
Smallanthus uvedalia	LOTUS Database	35616633
Solanum habrochaites	LOTUS Database	35616633
Solenostoma infuscum	LOTUS Database	35616633
Solidago odora	LOTUS Database	35616633
Stevia rebaudiana	LOTUS Database	35616633
Symphyopappus reticulatus	LOTUS Database	35616633
Tephroseris palustris	LOTUS Database	35616633
Teucrium cyprium	LOTUS Database	35616633
Teucrium sandrasicum	LOTUS Database	35616633
Tor sinensis	LOTUS Database	35616633
Tordylium apulum	LOTUS Database	35616633
Torilis arvensis	LOTUS Database	35616633
Trifolium pratense	LOTUS Database	35616633
Tripleurospermum maritimum	LOTUS Database	35616633
Umbellularia californica	LOTUS Database	35616633
Uvaria chamae	LOTUS Database	35616633
Viscum album	LOTUS Database	35616633
Vitex agnus-castus	LOTUS Database	35616633
Zea mays	LOTUS Database	35616633
Zingiber officinale	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

Farsesane sesquiterpenoid
Sesquiterpenoid
Alkatetraene
Branched unsaturated hydrocarbon
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Acyclic olefin
Hydrocarbon
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

beta-farnesene (CHEBI:10418 )
Farnesenes (C09666 )
Hydrocarbons (LMFA11000040 )

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	5.7	ALOGPS
logP	5.2	ChemAxon
logS	-4.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	72.18 m³·mol⁻¹	ChemAxon
Polarizability	26.89 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

HMDB0062763

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00003131

Chemspider ID

Not Available

KEGG Compound ID

C09666

BioCyc ID

CPD-8239

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281517

PDB ID

Not Available

ChEBI ID

10418

Good Scents ID

Not Available

References

General References

Schnee C, Kollner TG, Gershenzon J, Degenhardt J: The maize gene terpene synthase 1 encodes a sesquiterpene synthase catalyzing the formation of (E)-beta-farnesene, (E)-nerolidol, and (E,E)-farnesol after herbivore damage. Plant Physiol. 2002 Dec;130(4):2049-60. doi: 10.1104/pp.008326. [PubMed:12481088 ]
Kunert G, Reinhold C, Gershenzon J: Constitutive emission of the aphid alarm pheromone, (E)-beta-farnesene, from plants does not serve as a direct defense against aphids. BMC Ecol. 2010 Nov 23;10:23. doi: 10.1186/1472-6785-10-23. [PubMed:21092302 ]
Tesh RB, Guzman H, Wilson ML: Trans-beta-farnesene as a feeding stimulant for the sand fly Lutzomyia longipalpis (Diptera: Psychodidae). J Med Entomol. 1992 Mar;29(2):226-31. doi: 10.1093/jmedent/29.2.226. [PubMed:1495034 ]
Francis F, Lognay G, Haubruge E: Olfactory responses to aphid and host plant volatile releases: (E)-beta-farnesene an effective kairomone for the predator Adalia bipunctata. J Chem Ecol. 2004 Apr;30(4):741-55. doi: 10.1023/b:joec.0000028429.13413.a2. [PubMed:15260221 ]
Byers JA: A cost of alarm pheromone production in cotton aphids, Aphis gossypii. Naturwissenschaften. 2005 Feb;92(2):69-72. doi: 10.1007/s00114-004-0592-y. Epub 2004 Dec 7. [PubMed:15586262 ]
Su J, Zhu S, Zhang Z, Ge F: Effect of synthetic aphid alarm pheromone (E) -beta-farnesene on development and reproduction of Aphis gossypii (Homoptera: Aphididae). J Econ Entomol. 2006 Oct;99(5):1636-40. doi: 10.1603/0022-0493-99.5.1636. [PubMed:17066793 ]
Qiao H, Tuccori E, He X, Gazzano A, Field L, Zhou JJ, Pelosi P: Discrimination of alarm pheromone (E)-beta-farnesene by aphid odorant-binding proteins. Insect Biochem Mol Biol. 2009 May-Jun;39(5-6):414-9. doi: 10.1016/j.ibmb.2009.03.004. Epub 2009 Mar 27. [PubMed:19328854 ]
Vandermoten S, Mescher MC, Francis F, Haubruge E, Verheggen FJ: Aphid alarm pheromone: an overview of current knowledge on biosynthesis and functions. Insect Biochem Mol Biol. 2012 Mar;42(3):155-63. doi: 10.1016/j.ibmb.2011.11.008. Epub 2011 Dec 8. [PubMed:22178597 ]

Showing NP-Card for (E)-Beta-Farnesene (NP0045030)

MOL for NP0045030 ((E)-Beta-Farnesene)

3D MOL for NP0045030 ((E)-Beta-Farnesene)

3D SDF for NP0045030 ((E)-Beta-Farnesene)

3D-SDF for NP0045030 ((E)-Beta-Farnesene)

PDB for NP0045030 ((E)-Beta-Farnesene)

3D PDB for NP0045030 ((E)-Beta-Farnesene)

SMILES for NP0045030 ((E)-Beta-Farnesene)

INCHI for NP0045030 ((E)-Beta-Farnesene)

Structure for NP0045030 ((E)-Beta-Farnesene)

3D Structure for NP0045030 ((E)-Beta-Farnesene)