NP-MRD: Showing NP-Card for (2Z,6E)-Farnesol (NP0336943)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2024-09-11 08:32:15 UTC

Updated at

2024-09-11 08:32:15 UTC

NP-MRD ID

NP0336943

Secondary Accession Numbers

None

Natural Product Identification

Common Name

(2Z,6E)-Farnesol

Description

(Z)-Farnesol, also known as (2Z,6E)-farnesol, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, (Z)-farnesol is considered to be an isoprenoid lipid molecule (Z)-Farnesol is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, (Z)-Farnesol has been detected, but not quantified in, lindens. This could make (Z)-farnesol a potential biomarker for the consumption of these foods. These are terpenes with three consecutive isoprene units.

Structure

MOL SDF PDB SMILES InChI


  Mrv0541 02241215452D          

 16 15  0  0  0  0            999 V2000
   -5.3920    2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6775    2.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9630    2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2486    2.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5341    2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8196    2.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1051    2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3907    2.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3238    2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0383    2.6223    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7527    2.2098    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6775    3.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8196    3.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0383    3.4473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7527    1.3848    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4671    0.9723    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  2  3  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
  2 12  1  0  0  0  0
  6 13  1  0  0  0  0
 10 14  1  0  0  0  0
 11 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0336943

> <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-PVMFERMNSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.3663

> <EXACT_MASS>
222.198365454

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
28.878152081633225

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,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>
(Z,E)-farnesol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0     -10.065   4.125   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.731   4.895   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -7.398   4.125   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -6.064   4.895   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.730   4.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.397   4.895   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.063   4.125   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.729   4.895   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.604   4.125   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.938   4.895   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.272   4.125   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.731   6.435   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.397   6.435   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.938   6.435   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.272   2.585   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       4.605   1.815   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   12                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   14                                                  
CONECT   11   10   15                                                       
CONECT   12    2                                                            
CONECT   13    6                                                            
CONECT   14   10                                                            
CONECT   15   11   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-cis,6-trans)-3,7,11-Trimethyldodeca-2,6,10-trien-1-ol	ChEBI
(2Z,6E)-Farnesol	ChEBI
(Z,e)-3,7,11-Trimethyl-2,6,10-dodecatrien-1-ol	ChEBI
(Z,e)-Farnesol	ChEBI
2-cis,6-trans-Farnesol	ChEBI
cis,trans-Farnesol	ChEBI
(2-cis,6-trans)-Farnesol	HMDB
(2Z,6E)-3,7,11-Trimethyldodeca-2,6,10-trien-1-ol	HMDB

Chemical Formula

C₁₅H₂₆O

Average Mass

222.3663 Da

Monoisotopic Mass

222.19837 Da

IUPAC Name

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

Traditional Name

(Z,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-PVMFERMNSA-N

Experimental Spectra

Not Available

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Not Available

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:16774 )
Acyclic farnesane sesquiterpenoids (C03220 )
Farnesenes (C03220 )
Acyclic farnesane sesquiterpenoids (LMPR0103010013 )

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	4.84	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	28.88 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

HMDB0059849

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB014760

KNApSAcK ID

Not Available

Chemspider ID

1266074

KEGG Compound ID

C03220

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

1549108

PDB ID

Not Available

ChEBI ID

16774

Good Scents ID

Not Available

References

General References

Showing NP-Card for (2Z,6E)-Farnesol (NP0336943)

MOL for NP0336943 ((2Z,6E)-Farnesol)

3D MOL for NP0336943 ((2Z,6E)-Farnesol)

3D SDF for NP0336943 ((2Z,6E)-Farnesol)

3D-SDF for NP0336943 ((2Z,6E)-Farnesol)

PDB for NP0336943 ((2Z,6E)-Farnesol)

3D PDB for NP0336943 ((2Z,6E)-Farnesol)

SMILES for NP0336943 ((2Z,6E)-Farnesol)

INCHI for NP0336943 ((2Z,6E)-Farnesol)

Structure for NP0336943 ((2Z,6E)-Farnesol)

3D Structure for NP0336943 ((2Z,6E)-Farnesol)