NP-MRD: Showing NP-Card for Farnesol (NP0043872)

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Record Information

Version

1.0

Created at

2021-06-22 17:26:50 UTC

Updated at

2021-08-20 00:00:46 UTC

NP-MRD ID

NP0043872

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Farnesol

Description

Farnesol, also known as (2E,6E)-farnesol or trans-farnesol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, farnesol is considered to be an isoprenoid. Farnesol exists in all eukaryotes, ranging from yeast to plants to humans. In humans, farnesol is involved in the bile acid indirect signalling pathway. Farnesol is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Farnesol is found in Abies firma, Acokanthera oblongifolia, Ageratum conyzoides, Alpinia conchigera, Artemisia monosperma, Boletinus cavipes, Bombus hortorum, Bothriochloa bladhii, Centella asiatica, Chaerophyllum macrospermum, Cinnamomum sieboldii, Citrus aurantiifolia, Citrus aurantium, Citrus maxima, Citrus paradise x Poncirus trifoliata, Poncirus trifoliata , Cleistopholis patens, Coluria geoides, Cymbopogon distans, Cymbopogon martinii, Cymbopogon schoenanthus, Daphne odora, Eucalyptus globulus , Eucommia ulmoides, Humulus lupulus, Juniperus communis, Laggera alata, Lantana camara, Larix kaempferi, Lentinellus cochleatus, Lonicera japonica, Loxodonta africana, Matricaria chamomilla, Melaleuca leucadendra, Monodora myristica , Murraya paniculata , Nicotiana alata, Origanum majorana, Origanum sipyleum, Paeonia lactiflora, Perilla frutescens, Pinus thunbergii, Pittosporum tobira, Poncirus trifoliate x Citrus sinensis, Pulicaria arabica, Rosa centifolia, Rudbeckia mollis, Sideritis tragoriganum, Suillus cavipes, Tagetes lucida, Tanacetum millefolium, Torreya nucifera, Uvaria pandensis, Zanthoxylum simulans, Zanthoxylum zanthoxyloides and Zieria minutiflora. It was first documented in 2000 (PMID: 10753967). Based on a literature review a significant number of articles have been published on Farnesol (PMID: 15840382) (PMID: 11254751) (PMID: 15158752) (PMID: 16845684).

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

NP0043872
     RDKit          3D

 42 41  0  0  0  0  0  0  0  0999 V2000
    6.6109    0.3395   -0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2463    0.3989   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0727    0.2622    1.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1897    0.5721   -1.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8463    0.6288   -0.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9273   -0.4750   -1.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6171   -0.2850   -0.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5387   -0.3602    1.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5101   -0.0454   -0.9915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386    0.1503   -0.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8501   -0.8515   -0.7766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1498   -0.5899   -0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2865   -1.5201   -0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2980    0.4203    0.7297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6319    0.6235    1.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0569    1.9091    0.9710 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6967    1.2097   -1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7483   -0.6297   -1.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3807    0.4070   -0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7123    1.2015    1.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0218   -0.0159    1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3756   -0.5951    1.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2965    0.6743   -2.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9034    0.5877    0.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3148    1.5925   -0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3648   -1.4775   -0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8459   -0.3924   -2.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481   -1.0521    1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3324    0.6178    1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5071   -0.7315    1.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4385    0.0075   -2.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7616    0.0959    0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1908    1.1615   -0.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0428   -0.7538   -1.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231   -1.9056   -0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6837   -1.9313    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0737   -1.0207   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9199   -2.3841   -1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4902    1.0792    0.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3858   -0.0783    1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5986    0.6175    2.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5705    2.5381    1.5402 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 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
M  END


  Mrv1652306222119262D          

 16 15  0  0  0  0            999 V2000
    6.1875    3.5724    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9500    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3000    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7125    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0625    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375    0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8250    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2375   -0.7145    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
   -0.4125   -0.7145    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 12 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043872

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9+,15-11+

> <INCHI_KEY>
CRDAMVZIKSXKFV-YFVJMOTDSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.3663

> <EXACT_MASS>
222.198365454

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.69644639972201

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol

> <ALOGPS_LOGP>
4.84

> <JCHEM_LOGP>
4.1620975709999986

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.33002421872553

> <JCHEM_PKA_STRONGEST_BASIC>
-2.2170474067294528

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
74.98469999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.87e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(E)-farnesol

> <JCHEM_VEBER_RULE>
1

$$$$

NP0043872
     RDKit          3D

 42 41  0  0  0  0  0  0  0  0999 V2000
    6.6109    0.3395   -0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2463    0.3989   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0727    0.2622    1.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1897    0.5721   -1.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8463    0.6288   -0.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9273   -0.4750   -1.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6171   -0.2850   -0.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5387   -0.3602    1.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5101   -0.0454   -0.9915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386    0.1503   -0.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8501   -0.8515   -0.7766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1498   -0.5899   -0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2865   -1.5201   -0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2980    0.4203    0.7297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6319    0.6235    1.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0569    1.9091    0.9710 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6967    1.2097   -1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7483   -0.6297   -1.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3807    0.4070   -0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7123    1.2015    1.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0218   -0.0159    1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3756   -0.5951    1.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2965    0.6743   -2.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9034    0.5877    0.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3148    1.5925   -0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3648   -1.4775   -0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8459   -0.3924   -2.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481   -1.0521    1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3324    0.6178    1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5071   -0.7315    1.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4385    0.0075   -2.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7616    0.0959    0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1908    1.1615   -0.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0428   -0.7538   -1.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231   -1.9056   -0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6837   -1.9313    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0737   -1.0207   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9199   -2.3841   -1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4902    1.0792    0.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3858   -0.0783    1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5986    0.6175    2.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5705    2.5381    1.5402 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 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
M  END

HEADER    PROTEIN                                 22-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   22-JUN-21         0                                  
HETATM    1  C   UNK     0      11.550   6.668   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.780   5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      11.550   4.001   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.930   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.000  -2.667   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    NP0043872
HETATM    1  C1  UNL     1       6.611   0.339  -0.860  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.246   0.399  -0.279  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.073   0.262   1.192  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.190   0.572  -1.066  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.846   0.629  -0.477  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.927  -0.475  -1.013  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.617  -0.285  -0.328  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.539  -0.360   1.139  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.510  -0.045  -0.991  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.839   0.150  -0.345  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.850  -0.851  -0.777  1.00  0.00           C  
HETATM   12  C12 UNL     1      -4.150  -0.590  -0.108  1.00  0.00           C  
HETATM   13  C13 UNL     1      -5.286  -1.520  -0.424  1.00  0.00           C  
HETATM   14  C14 UNL     1      -4.298   0.420   0.730  1.00  0.00           C  
HETATM   15  C15 UNL     1      -5.632   0.623   1.365  1.00  0.00           C  
HETATM   16  O1  UNL     1      -6.057   1.909   0.971  1.00  0.00           O  
HETATM   17  H1  UNL     1       6.697   1.210  -1.570  1.00  0.00           H  
HETATM   18  H2  UNL     1       6.748  -0.630  -1.377  1.00  0.00           H  
HETATM   19  H3  UNL     1       7.381   0.407  -0.070  1.00  0.00           H  
HETATM   20  H4  UNL     1       4.712   1.202   1.647  1.00  0.00           H  
HETATM   21  H5  UNL     1       6.022  -0.016   1.695  1.00  0.00           H  
HETATM   22  H6  UNL     1       4.376  -0.595   1.398  1.00  0.00           H  
HETATM   23  H7  UNL     1       4.297   0.674  -2.148  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.903   0.588   0.629  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.315   1.592  -0.711  1.00  0.00           H  
HETATM   26  H10 UNL     1       2.365  -1.477  -0.793  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.846  -0.392  -2.104  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.248  -1.052   1.499  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.332   0.618   1.618  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.507  -0.732   1.527  1.00  0.00           H  
HETATM   31  H15 UNL     1      -0.439   0.007  -2.071  1.00  0.00           H  
HETATM   32  H16 UNL     1      -1.762   0.096   0.763  1.00  0.00           H  
HETATM   33  H17 UNL     1      -2.191   1.162  -0.619  1.00  0.00           H  
HETATM   34  H18 UNL     1      -3.043  -0.754  -1.875  1.00  0.00           H  
HETATM   35  H19 UNL     1      -2.523  -1.906  -0.624  1.00  0.00           H  
HETATM   36  H20 UNL     1      -5.684  -1.931   0.541  1.00  0.00           H  
HETATM   37  H21 UNL     1      -6.074  -1.021  -1.025  1.00  0.00           H  
HETATM   38  H22 UNL     1      -4.920  -2.384  -1.011  1.00  0.00           H  
HETATM   39  H23 UNL     1      -3.490   1.079   0.948  1.00  0.00           H  
HETATM   40  H24 UNL     1      -6.386  -0.078   1.012  1.00  0.00           H  
HETATM   41  H25 UNL     1      -5.599   0.617   2.453  1.00  0.00           H  
HETATM   42  H26 UNL     1      -5.571   2.538   1.540  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4    4
CONECT    3   20   21   22
CONECT    4    5   23
CONECT    5    6   24   25
CONECT    6    7   26   27
CONECT    7    8    9    9
CONECT    8   28   29   30
CONECT    9   10   31
CONECT   10   11   32   33
CONECT   11   12   34   35
CONECT   12   13   14   14
CONECT   13   36   37   38
CONECT   14   15   39
CONECT   15   16   40   41
CONECT   16   42
END

NP0043872
     RDKit          3D

42 41  0  0  0  0  0  0  0  0999 V2000
    6.6109    0.3395   -0.8598 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2463    0.3989   -0.2793 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0727    0.2622    1.1915 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1897    0.5721   -1.0656 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8463    0.6288   -0.4768 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9273   -0.4750   -1.0128 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6171   -0.2850   -0.3277 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5387   -0.3602    1.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5101   -0.0454   -0.9915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8386    0.1503   -0.3445 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8501   -0.8515   -0.7766 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1498   -0.5899   -0.1083 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2865   -1.5201   -0.4242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2980    0.4203    0.7297 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6319    0.6235    1.3654 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0569    1.9091    0.9710 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6967    1.2097   -1.5695 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7483   -0.6297   -1.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3807    0.4070   -0.0699 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7123    1.2015    1.6465 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0218   -0.0159    1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3756   -0.5951    1.3975 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2965    0.6743   -2.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9034    0.5877    0.6287 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3148    1.5925   -0.7111 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3648   -1.4775   -0.7932 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8459   -0.3924   -2.1044 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2481   -1.0521    1.4989 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3324    0.6178    1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5071   -0.7315    1.5269 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4385    0.0075   -2.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7616    0.0959    0.7626 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1908    1.1615   -0.6188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0428   -0.7538   -1.8754 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5231   -1.9056   -0.6236 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6837   -1.9313    0.5409 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0737   -1.0207   -1.0249 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9199   -2.3841   -1.0109 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4902    1.0792    0.9480 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3858   -0.0783    1.0123 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5986    0.6175    2.4529 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5705    2.5381    1.5402 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 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  2  0
 14 15  1  0
 15 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 11 34  1  0
 11 35  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
 16 42  1  0
M  END

View in JSmol

Synonyms

Value	Source
(2-trans,6-trans)-3,7,11-Trimethyldodeca-2,6,10-trien-1-ol	ChEBI
(2E,6E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol	ChEBI
(2E,6E)-Farnesol	ChEBI
(e)-Farnesol	ChEBI
(e,e)-Farnesol	ChEBI
2-trans,6-trans-Farnesol	ChEBI
all-trans-Farnesol	ChEBI
trans,trans-alpha-Farnesol	ChEBI
trans,trans-Farnesol	ChEBI
trans-Farnesol	ChEBI
Ditrans,polycis-polyprenol	Kegg
trans,trans-a-Farnesol	Generator
trans,trans-Α-farnesol	Generator
2-cis,6-trans-Farnesol	HMDB
3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol	HMDB
Farnesyl alcohol	HMDB
FCI 119a	HMDB
Nikkosome	HMDB
Farnesol	MeSH
(E)-beta-Farnesol	PhytoBank
(E)-β-Farnesol	PhytoBank
(E,E)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol	PhytoBank
(E,E)-Farnesyl alcohol	PhytoBank
(t,t)-Farnesol	PhytoBank
2,6-Di-trans-farnesol	PhytoBank
2,6-trans,trans-Farnesol	PhytoBank
3,7,11-Trimethyldodeca-2-trans,6-trans,10-trien-1-ol	PhytoBank
all-E-Farnesol	PhytoBank
trans-1-Hydroxy-3,7,11-trimethyl-2,6,10-dodecatriene	PhytoBank
trans-2,trans-6-Farnesol	PhytoBank
3,7,11-Trimethyl-2,6,10-dodecen-1-ol	PhytoBank

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3663 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trien-1-ol

Traditional Name

(E)-farnesol

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H26O/c1-13(2)7-5-8-14(3)9-6-10-15(4)11-12-16/h7,9,11,16H,5-6,8,10,12H2,1-4H3/b14-9+,15-11+

InChI Key

CRDAMVZIKSXKFV-YFVJMOTDSA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 62.9 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 250.1 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 150 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 250 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 175 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 225 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 125 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, Chloroform-d, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Abelmoschus moschatus	KNApSAcK Database	22123792
Abies firma	LOTUS Database	35616633
Acokanthera oblongifolia	LOTUS Database	35616633
Ageratum conyzoides	LOTUS Database	35616633
Alpinia conchigera	LOTUS Database	35616633
Artemisia monosperma	LOTUS Database	35616633
Azadirachta indica	KNApSAcK Database	22123792
Boletinus cavipes	Linigton's dataset	Tomonari Wada, Kenji Kobata, Yasuo Hayashi & Hisao Shibata (1995) Two Chemotypes of Boletinus cav...
Bombus hortorum	LOTUS Database	35616633
Bothriochloa bladhii	LOTUS Database	35616633
Cannabis sativa	CannabisDB	Not Available
Centella asiatica	LOTUS Database	35616633
Chaerophyllum macrospermum	LOTUS Database	35616633
Chamaemelum nobile	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cinnamomum aromaticum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cinnamomum sieboldii	LOTUS Database	35616633
Cinnamomum verum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Citrus aurantiifolia	LOTUS Database	35616633
Citrus aurantium	LOTUS Database	35616633
Citrus maxima	LOTUS Database	35616633
Citrus paradise x Poncirus trifoliata	Plant	KNApSAcK
Citrus trifoliata	Plant	KNApSAcK
Cleistopholis patens	LOTUS Database	35616633
Coluria geoides	LOTUS Database	35616633
Cuminum cyminum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cymbopogon citratus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Cymbopogon distans	LOTUS Database	35616633
Cymbopogon martinii	LOTUS Database	35616633
Cymbopogon schoenanthus	LOTUS Database	35616633
Daphne odora	LOTUS Database	35616633
Eucalyptus globulus	Plant	KNApSAcK
Eucommia ulmoides	LOTUS Database	35616633
Hibiscus abelmoschus	KNApSAcK Database	22123792
Humulus lupulus	LOTUS Database	35616633
Juniperus communis	LOTUS Database	35616633
Laggera alata	LOTUS Database	35616633
Lantana camara	LOTUS Database	35616633
Larix kaempferi	LOTUS Database	35616633
Lentinellus cochleatus	LOTUS Database	35616633
Lonicera japonica	LOTUS Database	35616633
Loxodonta africana	LOTUS Database	35616633
Malus pumila	FooDB	PHYTOHUB
Matricaria chamomilla	LOTUS Database	35616633
Matricaria recutita	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Melaleuca leucadendra	LOTUS Database	35616633
Mentha spicata	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Monodora myristica	Plant	KNApSAcK
Murraya paniculata	Plant	KNApSAcK
Nicotiana alata	Plant	KNApSAcK
Ocimum basilicum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum majorana	LOTUS Database	35616633
Origanum onites	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Origanum sipyleum	LOTUS Database	35616633
Paeonia lactiflora	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Pinus thunbergii	LOTUS Database	35616633
Pittosporum tobira	LOTUS Database	35616633
Polygonum minus	KNApSAcK Database	22123792
Poncirus trifoliate x Citrus sinensis	Plant	KNApSAcK
Pulicaria arabica	LOTUS Database	35616633
Rosa centifolia	LOTUS Database	35616633
Rubus idaeus	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Rudbeckia mollis	LOTUS Database	35616633
Salvia officinalis	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Santalum album	KNApSAcK Database	22123792
Santalum spicatum	KNApSAcK Database	22123792
Sideritis tragoriganum	LOTUS Database	35616633
Suillus cavipes	LOTUS Database	35616633
Tagetes lucida	LOTUS Database	35616633
Tanacetum millefolium	LOTUS Database	35616633
Torreya nucifera	LOTUS Database	35616633
Uvaria pandensis	LOTUS Database	35616633
Vaccinium corymbosum	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases
Zanthoxylum simulans	LOTUS Database	35616633
Zanthoxylum zanthoxyloides	LOTUS Database	35616633
Zieria minutiflora	LOTUS Database	35616633
Zingiber officinale	FooDB	Dr. Duke's Phytochemical and Ethnobotanical Databases

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
Fatty alcohol
Fatty acyl
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

farnesol (CHEBI:16619 )
Other Prenol lipids (C06081 )
Acyclic farnesane sesquiterpenoids (LMPR0103010001 )

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	283.00 to 284.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	1.29 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.314 (est)	The Good Scents Company Information System

Predicted Properties

Property	Value	Source
logP	4.84	ALOGPS
logP	4.16	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	16.33	ChemAxon
pKa (Strongest Basic)	-2.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	7	ChemAxon
Refractivity	74.98 m³·mol⁻¹	ChemAxon
Polarizability	28.7 Å³	ChemAxon
Number of Rings	0	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

HMDB0004305

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

2-TRANS6-TRANS-FARNESOL

BiGG ID

Not Available

Wikipedia Link

Farnesol

METLIN ID

7048

PubChem Compound

445070

PDB ID

Not Available

ChEBI ID

16619

Good Scents ID

rw1290201

References

General References

Horn TL, Long L, Cwik MJ, Morrissey RL, Kapetanovic IM, McCormick DL: Modulation of hepatic and renal drug metabolizing enzyme activities in rats by subchronic administration of farnesol. Chem Biol Interact. 2005 Apr 15;152(2-3):79-99. doi: 10.1016/j.cbi.2005.02.006. [PubMed:15840382 ]
Hanley K, Wood L, Ng DC, He SS, Lau P, Moser A, Elias PM, Bikle DD, Williams ML, Feingold KR: Cholesterol sulfate stimulates involucrin transcription in keratinocytes by increasing Fra-1, Fra-2, and Jun D. J Lipid Res. 2001 Mar;42(3):390-8. [PubMed:11254751 ]
DeBarber AE, Bleyle LA, Roullet JB, Koop DR: Omega-hydroxylation of farnesol by mammalian cytochromes p450. Biochim Biophys Acta. 2004 Jun 1;1682(1-3):18-27. doi: 10.1016/j.bbalip.2004.01.003. [PubMed:15158752 ]
Saidi S, Luitaud C, Rouabhia M: In vitro synergistic effect of farnesol and human gingival cells against Candida albicans. Yeast. 2006 Jul 15;23(9):673-87. doi: 10.1002/yea.1389. [PubMed:16845684 ]
Hanley K, Komuves LG, Ng DC, Schoonjans K, He SS, Lau P, Bikle DD, Williams ML, Elias PM, Auwerx J, Feingold KR: Farnesol stimulates differentiation in epidermal keratinocytes via PPARalpha. J Biol Chem. 2000 Apr 14;275(15):11484-91. doi: 10.1074/jbc.275.15.11484. [PubMed:10753967 ]
Tomonari Wada, Kenji Kobata, Yasuo Hayashi & Hisao Shibata (1995). Tomonari Wada, Kenji Kobata, Yasuo Hayashi & Hisao Shibata (1995) Two Chemotypes of Boletinus cavipes, Bioscience, Biotechnology, and Biochemistry, 59:6, 1036-1039, DOI: 10.1271/bbb.59.1036. Bioscience, Biotechnology, and Biochemistry.

Showing NP-Card for Farnesol (NP0043872)

MOL for NP0043872 (Farnesol)

3D MOL for NP0043872 (Farnesol)

3D SDF for NP0043872 (Farnesol)

3D-SDF for NP0043872 (Farnesol)

PDB for NP0043872 (Farnesol)

3D PDB for NP0043872 (Farnesol)

SMILES for NP0043872 (Farnesol)

INCHI for NP0043872 (Farnesol)

Structure for NP0043872 (Farnesol)

3D Structure for NP0043872 (Farnesol)