NP-MRD: Showing NP-Card for trans-trans-alpha-Farnesene (NP0044239)

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Record Information

Version

1.0

Created at

2022-02-14 20:33:34 UTC

Updated at

2022-03-10 22:22:42 UTC

NP-MRD ID

NP0044239

Secondary Accession Numbers

None

Natural Product Identification

Common Name

trans-trans-alpha-Farnesene

Description

Trans-trans-alpha-Farnesene, also known as (3E,6E)-alpha-Farnesene, 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. There are four known Alpha-farnesene stereoisomers which differ about the geometry of two of its three internal double bonds (the stereoisomers of the third internal double bond are identical). (3E,6E)-alpha-Farnesene is one of the 4 isomers of Alpha-farnesene and is the most common isomer, Trans-trans-alpha-Farnesene is a hydrophobic, neutral molecule that is not water soluble. It has a woody, bergamot, green and citrus like aroma and a fresh, green, fruity taste. Trans-trans-alpha-Farnesene is used as a flavoring and perfuming agent. It is found in the coating of apples, and other fruits, and it is responsible for the characteristic green apple odour (doi:10.1038/2101260A0). (3E,6E)-alpha-Farnesene is found within a few different foods, such as gingers, cottonseeds, common oregano and sweet oranges. (3E,6E)-alpha-Farnesene has also been detected, but not quantified in, several different foods, such as apples, pears, spearmints, guava, and carrots. Trans-trans-alpha-farnesene 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).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 38  0  0  0  0  0  0  0  0999 V2000
    5.5202   -1.5610    0.9551 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7155   -0.5257    0.9327 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8322   -0.1972   -0.1744 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7512   -1.0223   -1.4214 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0600    0.8967   -0.0615 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1528    1.2982   -1.1123 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7279    1.3804   -0.8558 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0415    1.1344    0.2343 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7259    0.7035    1.4549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4583    1.2917    0.2653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1457   -0.0123    0.5997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6063    0.2204    0.6100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4461   -0.4163   -0.1910 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8646   -1.4081   -1.1369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8966   -0.1736   -0.1686 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6153   -2.2738    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1417   -1.7041    1.8519 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7163    0.1274    1.8094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0699   -0.3876   -2.2921 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4308   -1.8564   -1.3444 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7099   -1.4029   -1.5730 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1507    1.4710    0.8397 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4854    2.2619   -1.6167 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2913    0.5519   -1.9664 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1114    1.7044   -1.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4193   -0.1378    1.3596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0480    0.3144    2.1942 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1433    1.5854    2.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7310    2.0633    1.0376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7705    1.6712   -0.7024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7623   -0.4909    1.4942 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9396   -0.7209   -0.2520 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0262    0.9488    1.3057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1802   -0.9047   -1.8601 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6753   -1.8490   -1.7590 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2974   -2.2004   -0.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2111    0.4480    0.6793 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2712    0.3056   -1.1035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4820   -1.1337   -0.0717 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  2  3
  3  4  1  0
  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 22  1  0
  4 19  1  0
  4 20  1  0
  4 21  1  0
  2 18  1  0
  1 16  1  0
  1 17  1  0
M  END


  Mrv1652309272007302D          

 15 14  0  0  0  0            999 V2000
 9998.0454 9998.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.7603 9997.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9999.4735 9998.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.1888 9997.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9042 9998.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.6174 9997.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.3328 9998.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.9042 9999.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9997.3309 9997.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9996.6141 9998.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.8996 9997.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1850 9998.1947    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9994.4705 9997.7833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9995.1850 9999.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9998.0454 9999.0200    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  9  1  0  0  0  0
  1 15  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  8  1  0  0  0  0
  6  7  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0044239

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9-10,12H,1,7-8,11H2,2-5H3/b14-10+,15-12+

> <INCHI_KEY>
CXENHBSYCFFKJS-VDQVFBMKSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.3511

> <EXACT_MASS>
204.187800768

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.857514706649745

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene

> <ALOGPS_LOGP>
5.70

> <JCHEM_LOGP>
5.138880741333333

> <ALOGPS_LOGS>
-4.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
73.2541

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.19e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
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    8663.0188663.297   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8664.3528662.529   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8665.6848663.297   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8667.0198662.529   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8668.3558663.297   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8669.6868662.529   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8671.0218663.297   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8668.3558664.837   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8661.6848662.529   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8660.3468663.297   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8659.0138662.529   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8657.6798663.297   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8656.3458662.529   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8657.6798664.837   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8663.0188664.837   0.000  0.00  0.00           C+0
CONECT    1    2    9   15                                                  
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7                                                       
CONECT    7    6                                                            
CONECT    8    5                                                            
CONECT    9    1   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12                                                            
CONECT   15    1                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   28    0
END

View in JSmol

Synonyms

Value	Source
(E,E)-Farnesene	HMDB
trans-Farnesene	HMDB
3,7,11-Trimethyl-(E,E)-1,3,6,10-dodecatetraene	HMDB
alpha-trans,trans-Farnesene	HMDB
trans,trans-alpha-Farnesene	HMDB
(3E,6E)-a-Farnesene	Generator
(3E,6E)-α-Farnesene	Generator
alpha-Farnesene	MeSH
(3E,6E)-3,7,11-Trimethyl-1,3,6,10-dodecatetraene	HMDB
(3E,6E)-alpha-Farnesene	HMDB
(E,E)-alpha-Farnesene	HMDB
(E,E)-α-Farnesene	HMDB
3,7,11-Trimethyl-1,3,6,10-dodecatetraene	HMDB
Farnesene	HMDB
trans,trans-α-Farnesene	HMDB
trans-2,6,10-Trimethyl-2,6,9,11-dodecatetraene	HMDB
trans-3,7,11-Trimethyl-1,3,6,10-dodecatetraene	HMDB
trans-alpha-Farnesene	HMDB
trans-α-Farnesene	HMDB
α-Farnesene	HMDB

Chemical Formula

C₁₅H₂₄

Average Mass

204.3511 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

(3E,6E)-3,7,11-trimethyldodeca-1,3,6,10-tetraene

Traditional Name

farnesene

CAS Registry Number

502-61-4

SMILES

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

InChI Identifier

InChI=1S/C15H24/c1-6-14(4)10-8-12-15(5)11-7-9-13(2)3/h6,9-10,12H,1,7-8,11H2,2-5H3/b14-10+,15-12+

InChI Key

CXENHBSYCFFKJS-VDQVFBMKSA-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
Abelmoschus esculentus	FooDB	FooDB
Actinidia chinensis	FooDB	FooDB
Agaricus bisporus	FooDB	FooDB
Agave	FooDB	FooDB
Ageratum conyzoides	LOTUS Database	35616633
Allium ampeloprasum	FooDB	FooDB
Allium ascalonicum	FooDB	FooDB
Allium cepa	FooDB	FooDB
Allium cepa L.	FooDB	FooDB
Allium fistulosum	FooDB	FooDB
Allium sativum	FooDB	FooDB
Allium schoenoprasum	FooDB	FooDB
Allium tuberosum	FooDB	FooDB
Aloysia triphylla	FooDB	FooDB
Alpinia galanga (L.) Sw.	Plant	KNApSAcK
Amaranthus	FooDB	FooDB
Amelanchier alnifolia	FooDB	FooDB
Anacardium occidentale	Plant	KNApSAcK
Ananas comosus	FooDB	FooDB
Anethum graveolens	FooDB	FooDB
Angelica keiskei	FooDB	FooDB
Annona cherimola	FooDB	FooDB
Annona muricata	FooDB	FooDB
Annona reticulata	FooDB	FooDB
Annona squamosa	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Anthemis cotula	LOTUS Database	35616633
Anthriscus cerefolium	FooDB	FooDB
Apium graveolens	FooDB	FooDB
Apium graveolens var. dulce	FooDB	FooDB
Apium graveolens var. rapaceum	FooDB	FooDB
Apium graveolens var. secalinum	FooDB	FooDB
Arachis hypogaea	FooDB	FooDB
Arctium lappa	FooDB	FooDB
Aristolochia macroura	LOTUS Database	35616633
Armoracia rusticana	FooDB	FooDB
Artemisia annua	LOTUS Database	35616633
Artemisia annua L.cultivar Jwarharti	Plant	KNApSAcK
Artemisia dracunculus	FooDB	FooDB
Artemisia frigida	LOTUS Database	35616633
Artemisia thuscula	LOTUS Database	35616633
Artemisia vulgaris	FooDB	FooDB
Artocarpus altilis	FooDB	FooDB
Artocarpus heterophyllus	FooDB	FooDB
Asparagus officinalis	FooDB	FooDB
Athamanta macedonica	LOTUS Database	35616633
Athanasia crithmifolia	LOTUS Database	35616633
Attalea speciosa	FooDB	FooDB
Auricularia auricula-judae	FooDB	FooDB
Auricularia polytricha	FooDB	FooDB
Austromyrtus dulcis	LOTUS Database	35616633
Avena sativa L.	FooDB	FooDB
Averrhoa carambola	FooDB	FooDB
Basella alba	FooDB	FooDB
Bellis perennis	LOTUS Database	35616633
Benincasa hispida	FooDB	FooDB
Bertholletia excelsa	FooDB	FooDB
Beta vulgaris	Plant	KNApSAcK
Beta vulgaris ssp. cicla	FooDB	FooDB
Blumea mollis	LOTUS Database	35616633
Borago officinalis	FooDB	FooDB
Brassica alboglabra	FooDB	FooDB
Brassica juncea	FooDB	FooDB
Brassica napus	FooDB	FooDB
Brassica napus var. napus	FooDB	FooDB
Brassica oleracea	FooDB	FooDB
Brassica oleracea var. botrytis	FooDB	FooDB
Brassica oleracea var. capitata	FooDB	FooDB
Brassica oleracea var. gemmifera	FooDB	FooDB
Brassica oleracea var. gongylodes	FooDB	FooDB
Brassica oleracea var. italica	FooDB	FooDB
Brassica oleracea var. sabauda	FooDB	FooDB
Brassica oleracea var. viridis	FooDB	FooDB
Brassica rapa	FooDB	FooDB
Brassica rapa ssp. chinensis	FooDB	FooDB
Brassica rapa var. pekinensis	FooDB	FooDB
Brassica rapa var. rapa	FooDB	FooDB
Brassica ruvo	FooDB	FooDB
Brosimum alicastrum	FooDB	FooDB
Buphthalmum salicifolium	LOTUS Database	35616633
Byrsonima crassifolia	FooDB	FooDB
Cajanus cajan	FooDB	FooDB
Cananga odorata	LOTUS Database	35616633
Canarium ovatum	FooDB	FooDB
Cannabis sativa	CannabisDB	Not Available
Cantharellus cibarius	FooDB	FooDB
Capparis spinosa	FooDB	FooDB
Capsicum annuum	FooDB	FooDB
Capsicum annuum L.	FooDB	FooDB
Capsicum annuum var. annuum	FooDB	FooDB
Capsicum chinense	FooDB	FooDB
Capsicum pubescens	FooDB	FooDB
Carica papaya L.	FooDB	FooDB
Carissa macrocarpa	FooDB	FooDB
Carthamus tinctorius	FooDB	FooDB
Carum carvi	FooDB	FooDB
Carya	FooDB	FooDB
Carya illinoinensis	FooDB	FooDB
Castanea	FooDB	FooDB
Castanea crenata	FooDB	FooDB
Castanea mollissima	FooDB	FooDB
Castanea sativa	FooDB	FooDB
Castanopsis cuspidata	LOTUS Database	35616633
Ceratitis capitata	LOTUS Database	35616633
Ceratonia siliqua	FooDB	FooDB
Chamaemelum nobile	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Chamerion angustifolium	FooDB	FooDB
Chamomilla recutina	Plant	KNApSAcK
Chenopodium album	FooDB	FooDB
Chenopodium quinoa	FooDB	FooDB
Chrysanthemum coronarium	FooDB	FooDB
Cicer arietinum	FooDB	FooDB
Cichorium endivia	FooDB	FooDB
Cichorium intybus	FooDB	FooDB
Cinnamomum	FooDB	FooDB
Cinnamomum aromaticum	FooDB	FooDB
Cinnamomum illicioides	Plant	KNApSAcK
Cinnamomum verum	FooDB	FooDB
Cirsium	FooDB	FooDB
Citrullus lanatus	FooDB	FooDB
Citrus ×limon (L.) Burm. f. (pro sp.)	FooDB	FooDB
Citrus aurantiifolia	FooDB	FooDB
Citrus aurantium	Plant	KNApSAcK
Citrus latifolia	FooDB	FooDB
Citrus limon	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus maxima	FooDB	FooDB
Citrus natsudaidai	LOTUS Database	35616633
Citrus paradisi	FooDB	FooDB
Citrus reticulata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus reticulate x Citrus sinensis	Plant	KNApSAcK
Citrus X sinensis (L.) Osbeck (pro. sp.)	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cocos nucifera	FooDB	FooDB
Coffea arabica L.	FooDB	FooDB
Coffea canephora	FooDB	FooDB
Colocasia esculenta	FooDB	FooDB
Corchorus olitorius	FooDB	FooDB
Coriandrum sativum L.	FooDB	FooDB
Corylus	FooDB	FooDB
Corylus avellana	FooDB	FooDB
Crateva religiosa	FooDB	FooDB
Crocus sativus	FooDB	FooDB
Croton jacobinensis	LOTUS Database	35616633
Cucumis melo	FooDB	FooDB
Cucumis metuliferus	FooDB	FooDB
Cucumis sativus L.	FooDB	FooDB
Cucurbita	FooDB	FooDB
Cucurbita maxima	FooDB	FooDB
Cucurbita moschata	FooDB	FooDB
Cuminum cyminum	FooDB	FooDB
Curcuma longa	FooDB	FooDB
Curcuma mangga	Plant	KNApSAcK
Cydonia oblonga	FooDB	FooDB
Cymbopogon citratus	FooDB	FooDB
Cymbopogon martinii	LOTUS Database	35616633
Cynara cardunculus	FooDB	FooDB
Cynara scolymus	FooDB	FooDB
Daphne papyracea	LOTUS Database	35616633
Daucus carota	Plant	KNApSAcK
Daucus carota ssp. sativus	FooDB	12926889
Dimocarpus longan	FooDB	FooDB
Dioscorea	FooDB	FooDB
Dioscorea pentaphylla	FooDB	FooDB
Diospyros	FooDB	FooDB
Diospyros kaki	FooDB	FooDB
Diospyros virginiana	FooDB	FooDB
Durio zibethinus	FooDB	FooDB
Dysphania ambrosioides	FooDB	FooDB
Elaeis	FooDB	FooDB
Eleocharis dulcis	FooDB	FooDB
Elettaria cardamomum	FooDB	FooDB
Empetrum nigrum	FooDB	FooDB
Encelia canescens	LOTUS Database	35616633
Entandrophragma cylindricum	LOTUS Database	35616633
Eragrostis tef	FooDB	FooDB
Eremanthus arboreus	LOTUS Database	35616633
Eriobotrya japonica	FooDB	FooDB
Eruca vesicaria subsp. Sativa	FooDB	FooDB
Eugenia javanica	FooDB	FooDB
Eugenia uniflora	FooDB	FooDB
Eupatorium cannabinum	LOTUS Database	35616633
Eutrema japonicum	FooDB	FooDB
Fagopyrum esculentum	FooDB	FooDB
Fagopyrum tataricum	FooDB	FooDB
Fagus	FooDB	FooDB
Feijoa sellowiana	Plant	KNApSAcK
Felicia filifolia	LOTUS Database	35616633
Ferula ovina	LOTUS Database	35616633
Ficus carica	FooDB	FooDB
Flammulina velutipes	FooDB	FooDB
Foeniculum vulgare	FooDB	FooDB
Fragaria x ananassa	FooDB	FooDB
Frullania spinifera	Plant	KNApSAcK
Garcinia mangostana	FooDB	FooDB
Gaylussacia baccata	FooDB	FooDB
Ginkgo biloba	FooDB	FooDB
Glycine max	FooDB	FooDB
Gossypium	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Gossypium hirsutum	LOTUS Database	35616633
Grifola frondosa	FooDB	FooDB
Gundelia tournefortii	LOTUS Database	35616633
Hamamelis virginiana	LOTUS Database	35616633
Haplocarpha scaposa	LOTUS Database	35616633
Hedysarum alpinum	FooDB	FooDB
Helianthus annuus L.	FooDB	FooDB
Helianthus tuberosus	FooDB	FooDB
Heracleum dissectum	LOTUS Database	35616633
Hibiscus sabbariffa	FooDB	FooDB
Hippophae rhamnoides	FooDB	FooDB
Hordeum vulgare	FooDB	FooDB
Houttuynia cordata	Plant	KNApSAcK
Houttuynia emeiensis	Plant	KNApSAcK
Humulus lupulus	LOTUS Database	35616633
Hyssopus officinalis L.	FooDB	FooDB
Illicium verum	FooDB	FooDB
Inula racemosa	LOTUS Database	35616633
Ipomoea aquatica	FooDB	FooDB
Ipomoea batatas	FooDB	FooDB
Juglans	FooDB	FooDB
Juglans ailanthifolia	FooDB	FooDB
Juglans cinerea	FooDB	FooDB
Juglans nigra L.	FooDB	FooDB
Juglans regia	FooDB	FooDB
Lablab purpureus	FooDB	FooDB
Lactuca sativa	FooDB	FooDB
Lagenaria siceraria	FooDB	FooDB
Lathyrus sativus	FooDB	FooDB
Laurus nobilis L.	FooDB	FooDB
Lens culinaris	FooDB	FooDB
Lentinus edodes	FooDB	FooDB
Lepechinia floribunda	LOTUS Database	35616633
Lepidium sativum	FooDB	FooDB
Levisticum officinale	FooDB	FooDB
Ligularia fischeri	LOTUS Database	35616633
Linum usitatissimum	FooDB	FooDB
Lippia rehmannii	LOTUS Database	35616633
Litchi chinensis	FooDB	FooDB
Litsea cubeba	Plant	KNApSAcK
Lonicera japonica	LOTUS Database	35616633
Luffa aegyptiaca	FooDB	FooDB
Lupinus	FooDB	FooDB
Lupinus albus	FooDB	FooDB
Macadamia	FooDB	FooDB
Macadamia tetraphylla	FooDB	FooDB
Malpighia emarginata	FooDB	FooDB
Malus	FooDB	KNAPSACK
Malus pumila	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Malus spp.	Plant	KNApSAcK
Mammea americana	FooDB	FooDB
Mangifera indica	FooDB	FooDB
Manihot esculenta	FooDB	FooDB
Manilkara zapota	FooDB	FooDB
Maranta arundinacea	FooDB	FooDB
Matricaria chamomilla	LOTUS Database	35616633
Matricaria recutita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Matteuccia struthiopteris	FooDB	FooDB
Medicago sativa	FooDB	FooDB
Melissa officinalis L.	FooDB	FooDB
Mentha	FooDB	FooDB
Mentha aquatica	FooDB	FooDB
Mentha arvensis	FooDB	FooDB
Mentha spicata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Mentha x piperita	FooDB	FooDB
Mespilus germanica	FooDB	FooDB
Metacalypogeia alternifolia	LOTUS Database	35616633
Metroxylon sagu	FooDB	FooDB
Microglossa zeylandica	Plant	KNApSAcK
Momordica charantia	FooDB	FooDB
Morchellaceae	FooDB	FooDB
Morella rubra	FooDB	FooDB
Morina persica	LOTUS Database	35616633
Moringa oleifera	FooDB	FooDB
Morus	FooDB	FooDB
Morus nigra	FooDB	FooDB
Murraya paniculata	Plant	KNApSAcK
Musa acuminata	FooDB	FooDB
Musa x paradisiaca	FooDB	FooDB
Myrica	FooDB	FooDB
Myristica fragrans	FooDB	FooDB
Myrmica scabrinodis	LOTUS Database	35616633
Myrtus communis	LOTUS Database	35616633
Nelumbo	FooDB	FooDB
Nelumbo nucifera	FooDB	FooDB
Nepeta nuda	LOTUS Database	35616633
Nephelium lappaceum	FooDB	FooDB
Nicotiana alata	Plant	KNApSAcK
Nuphar lutea	FooDB	FooDB
Nymphaea caerulea	Plant	KNApSAcK
Ocimum basilicum	Plant	KNApSAcK
Ocimum gratissimum	LOTUS Database	35616633
Ocimum kilimandscharicim	Plant	KNApSAcK
Ocimum tenuiflorum	Plant	KNApSAcK
Oenothera biennis	FooDB	FooDB
Olea europaea	FooDB	FooDB
Opuntia	FooDB	FooDB
Opuntia cochenillifera	FooDB	FooDB
Opuntia ficus-indica var.saboten	Plant	KNApSAcK
Opuntia macrorhiza	FooDB	FooDB
Origanum majorana	FooDB	FooDB
Origanum onites	FooDB	FooDB
Origanum sipyleum	LOTUS Database	35616633
Origanum vulgare	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum X majoricum	FooDB	FooDB
Oryza rufipogon	FooDB	FooDB
Oryza sativa	FooDB	FooDB
Pachyrhizus erosus	FooDB	FooDB
Panax ginseng	FooDB	FooDB
Pangium edule	FooDB	FooDB
Panicum miliaceum	FooDB	FooDB
Passiflora edulis	FooDB	FooDB
Pastinaca sativa	FooDB	FooDB
Pediomelum esculentum	FooDB	FooDB
Pelargonium endlicherianum	LOTUS Database	35616633
Perideridia oregana	FooDB	FooDB
Perilla frutescens	LOTUS Database	35616633
Persea americana	FooDB	FooDB
Petasites albus	Plant	KNApSAcK
Petasites hybridus	Plant	KNApSAcK
Petasites japonicus	FooDB	FooDB
Petroselinum crispum	FooDB	FooDB
Phaseolus coccineus	FooDB	FooDB
Phaseolus lunatus	FooDB	FooDB
Phaseolus vulgaris	FooDB	FooDB
Phoebe cinnamomifolia	Plant	KNApSAcK
Phoenix dactylifera	FooDB	FooDB
Photinia melanocarpa	FooDB	FooDB
Phyllostachys edulis	FooDB	FooDB
Physalis	FooDB	FooDB
Physalis philadelphica var. immaculata	FooDB	FooDB
Phytolacca americana	FooDB	FooDB
Pimenta dioica	FooDB	FooDB
Pimenta racemosa	LOTUS Database	35616633
Pimpinella anisum	FooDB	FooDB
Pinus	FooDB	FooDB
Pinus edulis	FooDB	FooDB
Pinus halepensis	Plant	KNApSAcK
Piper aduncum	LOTUS Database	35616633
Piper nigrum L.	Plant	KNApSAcK
Pistacia vera	FooDB	FooDB
Pisum sativum	FooDB	FooDB
Pleurotus ostreatus	FooDB	FooDB
Polygonum alpinum	FooDB	FooDB
Polygonum minus	Plant	KNApSAcK
Popillia japonica	LOTUS Database	35616633
Portulaca oleracea	FooDB	FooDB
Pouteria sapota	FooDB	FooDB
Primula halleri	Plant	KNApSAcK
Protium heptaphyllum	LOTUS Database	35616633
Prunus armeniaca	FooDB	FooDB
Prunus avium	FooDB	FooDB
Prunus avium L.	FooDB	FooDB
Prunus cerasus	FooDB	FooDB
Prunus domestica	FooDB	FooDB
Prunus dulcis	FooDB	FooDB
Prunus persica	FooDB	FooDB
Prunus persica var. nucipersica	FooDB	FooDB
Prunus persica var. persica	FooDB	FooDB
Prunus tomentosa	FooDB	FooDB
Prunus virginiana	FooDB	FooDB
Psidium cattleianum	FooDB	FooDB
Psidium guajava	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Psophocarpus tetragonolobus	FooDB	FooDB
Punica granatum	FooDB	FooDB
Pyrus communis	FooDB	Christian Chervin, Jim Speirs, Brian Loveys, Brian D Patterson. Influence of low oxygen storage o...
Pyrus pyrifolia	FooDB	FooDB
Pyrus spp.	Plant	KNApSAcK
Quercus	FooDB	FooDB
Raphanus sativus	FooDB	FooDB
Raphanus sativus var. longipinnatus	FooDB	FooDB
Raphanus sativus var. sativus	FooDB	FooDB
Rheum rhabarbarum	FooDB	FooDB
Rhododendron dauricum	LOTUS Database	35616633
Rhododendron mucronulatum	LOTUS Database	35616633
Ribes aureum	FooDB	FooDB
Ribes glandulosum	FooDB	FooDB
Ribes nigrum	FooDB	FooDB
Ribes rubrum	FooDB	FooDB
Ribes uva-crispa	FooDB	FooDB
Rosa	FooDB	FooDB
Rubus arcticus	FooDB	FooDB
Rubus chamaemorus	FooDB	FooDB
Rubus idaeus	FooDB	FooDB
Rubus occidentalis	FooDB	FooDB
Rubus spectabilis	FooDB	FooDB
Rugelia nudicaulis	LOTUS Database	35616633
Rumex	FooDB	FooDB
Rumex acetosa	FooDB	FooDB
Rumex articus	FooDB	FooDB
Sagittaria latifolia	FooDB	FooDB
Salix pulchra	FooDB	FooDB
Salvia elegans	FooDB	FooDB
Salvia hispanica	FooDB	FooDB
Salvia officinalis	FooDB	FooDB
Salvia rosmarinus	FooDB	FooDB
Sambucus nigra	FooDB	FooDB
Sambucus nigra L.	FooDB	FooDB
Satureja hortensis L.	FooDB	FooDB
Satureja montana	FooDB	FooDB
Scorzonera hispanica	FooDB	FooDB
Secale cereale	FooDB	FooDB
Sechium edule	FooDB	FooDB
Senecio inaequidens	LOTUS Database	35616633
Senecio vulgaris	Plant	KNApSAcK
Sesamum indicum	FooDB	FooDB
Sesbania bispinosa	FooDB	FooDB
Sinapis alba	FooDB	FooDB
Sisymbrium	FooDB	FooDB
Solanum lycopersicum	FooDB	FooDB
Solanum lycopersicum var. cerasiforme	FooDB	FooDB
Solanum lycopersicum var. lycopersicum	FooDB	FooDB
Solanum melongena	FooDB	FooDB
Solanum quitoense	FooDB	FooDB
Solanum tuberosum	FooDB	FooDB
Solenopsis invicta	LOTUS Database	35616633
Sorbus aucuparia	FooDB	FooDB
Sorghum bicolor	FooDB	FooDB
Spinacia oleracea	FooDB	FooDB
Syzygium aromaticum	FooDB	FooDB
Syzygium cumini	FooDB	FooDB
Syzygium jambos	FooDB	FooDB
Tamarindus indica	FooDB	FooDB
Tanacetum parthenium	LOTUS Database	35616633
Taraxacum officinale	FooDB	FooDB
Tetragonia tetragonioides	FooDB	FooDB
Thelesperma	FooDB	FooDB
Thymus longicaulis	LOTUS Database	35616633
Thymus pulegioides	FooDB	FooDB
Thymus vulgaris	FooDB	FooDB
Thymus zygioides	LOTUS Database	35616633
Tilia cordata	FooDB	FooDB
Tilia L.	FooDB	FooDB
Tipuana tipu	Plant	KNApSAcK
Tragopogon porrifolius	FooDB	FooDB
Trigonella foenum-graecum	FooDB	FooDB
Triticum	FooDB	FooDB
Triticum aestivum	FooDB	FooDB
Triticum durum	FooDB	FooDB
Triticum spelta	FooDB	FooDB
Triticum turanicum	FooDB	FooDB
Typha angustifolia	FooDB	FooDB
Vaccinium	FooDB	FooDB
Vaccinium angustifolium	FooDB	FooDB
Vaccinium angustifolium X Vaccinium corymbosum	FooDB	FooDB
Vaccinium arboreum	FooDB	FooDB
Vaccinium corymbosum	FooDB	FooDB
Vaccinium deliciosum	FooDB	FooDB
Vaccinium elliottii	FooDB	FooDB
Vaccinium macrocarpon	FooDB	FooDB
Vaccinium myrtilloides	FooDB	FooDB
Vaccinium myrtillus	FooDB	FooDB
Vaccinium ovalifolium	FooDB	FooDB
Vaccinium ovatum	FooDB	FooDB
Vaccinium oxycoccos	FooDB	FooDB
Vaccinium parvifolium	FooDB	FooDB
Vaccinium reticulatum	FooDB	FooDB
Vaccinium stamineum	FooDB	FooDB
Vaccinium uliginosum	FooDB	FooDB
Vaccinium vitis-idaea	FooDB	FooDB
Valerianella locusta	FooDB	FooDB
Vanda falcata	LOTUS Database	35616633
Vanilla	FooDB	FooDB
Verbena officinalis	FooDB	FooDB
Viburnum edule	FooDB	FooDB
Vicia faba	FooDB	FooDB
Vigna aconitifolia	FooDB	FooDB
Vigna angularis	FooDB	FooDB
Vigna mungo	FooDB	FooDB
Vigna radiata	FooDB	FooDB
Vigna umbellata	FooDB	FooDB
Vigna unguiculata	FooDB	FooDB
Vigna unguiculata ssp. cylindrica	FooDB	FooDB
Vigna unguiculata ssp. unguiculata	FooDB	FooDB
Vigna unguiculata var. sesquipedalis	FooDB	FooDB
Vismia cayennensis	LOTUS Database	35616633
Vitis	FooDB	FooDB
Vitis aestivalis	FooDB	FooDB
Vitis labrusca	FooDB	FooDB
Vitis rotundifolia	FooDB	FooDB
Vitis vinifera L.	FooDB	FooDB
Xanthosoma sagittifolium	FooDB	FooDB
Xylopia sericea	Plant	KNApSAcK
Zanthoxylum zanthoxyloides	LOTUS Database	35616633
Zea mays L.	FooDB	FooDB
Zingiber officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zingiber officinale ROSC.	Plant	KNApSAcK
Zizania	FooDB	FooDB
Zizania aquatica	FooDB	FooDB
Ziziphus zizyphus	FooDB	FooDB

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

alpha-farnesene (CHEBI:10280 )
Farnesenes (C09665 )

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	5.14	ChemAxon
logS	-4.6	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	6	ChemAxon
Refractivity	73.25 m³·mol⁻¹	ChemAxon
Polarizability	26.86 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

HMDB0036065

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Farnesene

METLIN ID

Not Available

PubChem Compound

5281516

PDB ID

Not Available

ChEBI ID

10280

Good Scents ID

Not Available

References

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
Bicker W, Lammerhofer M, Lindner W: Direct high-performance liquid chromatographic method for enantioselective and diastereoselective determination of selected pyrethroic acids. J Chromatogr A. 2004 Apr 30;1035(1):37-46. doi: 10.1016/j.chroma.2004.02.036. [PubMed:15117072 ]

Showing NP-Card for trans-trans-alpha-Farnesene (NP0044239)

MOL for NP0044239 (trans-trans-alpha-Farnesene)

3D MOL for NP0044239 (trans-trans-alpha-Farnesene)

3D SDF for NP0044239 (trans-trans-alpha-Farnesene)

3D-SDF for NP0044239 (trans-trans-alpha-Farnesene)

PDB for NP0044239 (trans-trans-alpha-Farnesene)

3D PDB for NP0044239 (trans-trans-alpha-Farnesene)

SMILES for NP0044239 (trans-trans-alpha-Farnesene)

INCHI for NP0044239 (trans-trans-alpha-Farnesene)

Structure for NP0044239 (trans-trans-alpha-Farnesene)

3D Structure for NP0044239 (trans-trans-alpha-Farnesene)