NP-MRD: Showing NP-Card for (e,z)-farnesol (NP0266358)

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Record Information

Version

2.0

Created at

2022-09-08 10:40:52 UTC

Updated at

2022-09-08 10:40:52 UTC

NP-MRD ID

NP0266358

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(e,z)-farnesol

Description

(2-Trans,6-cis)-farnesol, also known as (2E,6Z)-farnesol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, (2-trans,6-cis)-farnesol is considered to be an isoprenoid. (e,z)-farnesol is found in Abelmoschus moschatus, Abies firma, Abutilon indicum, Ageratum conyzoides, Alpinia conchigera, Anthemis cotula, Artemisia monosperma, Bothriochloa bladhii, Cannabis sativa, Centella asiatica, Chaerophyllum macrospermum, Cinnamomum sieboldii, Cinnamomum verum, Citrus aurantiifolia, Citrus aurantium, Cleistopholis patens, Cymbopogon distans, Cymbopogon martinii, Daphne odora, Humulus lupulus, Juniperus taxifolia, Laggera alata, Larix kaempferi, Lentinellus cochleatus, Loxodonta africana, Origanum majorana, Origanum sipyleum, Paeonia lactiflora, Perilla frutescens, Pittosporum tobira, Pulicaria arabica, Rosa gallica, Sideritis tragoriganum, Suillus cavipes, Tanacetum millefolium, Uvaria pandensis, Zanthoxylum simulans, Zieria minutiflora and Zingiber officinale. Based on a literature review very few articles have been published on (2-trans,6-cis)-farnesol.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 42 41  0  0  0  0  0  0  0  0999 V2000
   -5.5998   -1.7842    0.5059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4994   -0.8323    0.7740 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7930    0.4275    1.4915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2761   -1.1118    0.3749 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1482   -0.1489    0.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5669    0.2660   -0.7228 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4599    1.2078   -0.5196 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6578    2.5151    0.1773 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7353    0.9058   -0.9550 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1817   -0.2829   -1.6527 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0966   -1.1215   -0.8329 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3296   -0.4943   -0.3358 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3098    0.5778    0.6808 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4735   -0.9845   -0.7834 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8030   -0.4759   -0.3962 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8439    0.5667    0.4728 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2467   -2.8258    0.6840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4736   -1.6348    1.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9600   -1.7199   -0.5323 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3163    0.4262    2.4957 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4640    1.3281    0.9254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8825    0.5548    1.6531 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0732   -2.0381   -0.1500 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3139   -0.6439    1.1784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5424    0.6989    1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3039   -0.6646   -1.1959 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3978    0.8166   -1.2163 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7124    2.7623    0.3383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1692    2.4234    1.1703 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1652    3.3435   -0.3469 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5102    1.6916   -0.7942 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4110   -0.9526   -2.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7202    0.0790   -2.6024 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5467   -1.4707    0.1024 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3404   -2.0818   -1.3470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2685    0.7150    1.0770 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7122    1.4921    0.2402 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9715    0.3128    1.5478 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4582   -1.8427   -1.5061 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3063   -1.3454    0.1391 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4681   -0.3305   -1.2892 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5355    1.2002    0.2099 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

  Mrv1652309082212402D          

 16 15  0  0  0  0            999 V2000
    4.9500   -1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375   -0.7145    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
    4.9500   -0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    0.7145    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
    3.3000    1.4289    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
    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
   -1.2375   -0.7145    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>
NP0266358

> <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-GNESMGCMSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.372

> <EXACT_MASS>
222.198365457

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
42

> <JCHEM_AVERAGE_POLARIZABILITY>
28.71121379518336

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <JCHEM_LOGP>
4.1620975709999986

> <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>
74.9847

> <JCHEM_ROTATABLE_BOND_COUNT>
7

> <JCHEM_RULE_OF_FIVE>
1

> <JCHEM_TRADITIONAL_IUPAC>
(E,Z)-farnesol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 08-SEP-22   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-SEP-22         0                                  
HETATM    1  C   UNK     0       9.240  -2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.470  -1.334   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.930  -1.334   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       9.240  -0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       8.470   1.334   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.930   1.334   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   4.001   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      -2.310  -1.334   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

View in JSmol

Synonyms

Value	Source
(2-trans,6-cis)-3,7,11-Trimethyldodeca-2,6,10-trien-1-ol	ChEBI
(2E,6Z)-Farnesol	ChEBI
(e,Z)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol	ChEBI
(e,Z)-Farnesol	ChEBI
2-trans,6-cis-Farnesol	ChEBI
Farnesol	MeSH

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3720 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

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

Traditional Name

(E,Z)-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-GNESMGCMSA-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, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, H₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, 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 moschatus	LOTUS Database	35616633
Abies firma	LOTUS Database	35616633
Abutilon indicum	LOTUS Database	35616633
Ageratum conyzoides	LOTUS Database	35616633
Alpinia conchigera	LOTUS Database	35616633
Anthemis cotula	LOTUS Database	35616633
Artemisia monosperma	LOTUS Database	35616633
Bothriochloa bladhii	LOTUS Database	35616633
Cannabis sativa	LOTUS Database	35616633
Centella asiatica	LOTUS Database	35616633
Chaerophyllum macrospermum	LOTUS Database	35616633
Cinnamomum sieboldii	LOTUS Database	35616633
Cinnamomum verum	LOTUS Database	35616633
Citrus aurantiifolia	LOTUS Database	35616633
Citrus aurantium	LOTUS Database	35616633
Cleistopholis patens	LOTUS Database	35616633
Cymbopogon distans	LOTUS Database	35616633
Cymbopogon martinii	LOTUS Database	35616633
Daphne odora	LOTUS Database	35616633
Humulus lupulus	LOTUS Database	35616633
Juniperus taxifolia	LOTUS Database	35616633
Laggera alata	LOTUS Database	35616633
Larix kaempferi	LOTUS Database	35616633
Lentinellus cochleatus	LOTUS Database	35616633
Loxodonta africana	LOTUS Database	35616633
Origanum majorana	LOTUS Database	35616633
Origanum sipyleum	LOTUS Database	35616633
Paeonia lactiflora	LOTUS Database	35616633
Perilla frutescens	LOTUS Database	35616633
Pittosporum tobira	LOTUS Database	35616633
Pulicaria arabica	LOTUS Database	35616633
Rosa gallica	LOTUS Database	35616633
Sideritis tragoriganum	LOTUS Database	35616633
Suillus cavipes	LOTUS Database	35616633
Tanacetum millefolium	LOTUS Database	35616633
Uvaria pandensis	LOTUS Database	35616633
Zanthoxylum simulans	LOTUS Database	35616633
Zieria minutiflora	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
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:35966 )
Acyclic farnesane sesquiterpenoids (LMPR0103010006 )

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	4.16	ChemAxon
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	28.71 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

C00052495

Chemspider ID

1266075

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1549109

PDB ID

Not Available

ChEBI ID

35966

Good Scents ID

rw1595651

References

General References

LOTUS database [Link]

Showing NP-Card for (e,z)-farnesol (NP0266358)

MOL for NP0266358 ((e,z)-farnesol)

3D MOL for NP0266358 ((e,z)-farnesol)

3D SDF for NP0266358 ((e,z)-farnesol)

3D-SDF for NP0266358 ((e,z)-farnesol)

PDB for NP0266358 ((e,z)-farnesol)

3D PDB for NP0266358 ((e,z)-farnesol)

SMILES for NP0266358 ((e,z)-farnesol)

INCHI for NP0266358 ((e,z)-farnesol)

Structure for NP0266358 ((e,z)-farnesol)

3D Structure for NP0266358 ((e,z)-farnesol)