NP-MRD: Showing NP-Card for α-farnesene (NP0330794)

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Record Information

Version

1.0

Created at

2022-09-12 16:30:02 UTC

Updated at

2022-09-12 16:30:02 UTC

NP-MRD ID

NP0330794

Secondary Accession Numbers

None

Natural Product Identification

Common Name

α-farnesene

Description

Alpha-farnesene, also known as α-farnesene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. α-farnesene is found in Blumea mollis, Buphthalmum salicifolium, Ceratitis capitata, Croton jacobinensis, Dumortiera hirsuta, Felicia filifolia, Haplocarpha scaposa, Helianthus tuberosus, Ligularia fischeri, Myrmica scabrinodis, Piper aduncum, Popillia japonica, Rugelia nudicaulis, Senecio inaequidens, Solenopsis invicta and Vismia cayennensis. Alpha-farnesene is possibly neutral.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 39 38  0  0  0  0  0  0  0  0999 V2000
    6.5019   -1.5207    0.1623 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3316   -1.3927   -0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.3745   -0.0787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6290    0.6370    0.9676 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1866   -0.3056   -0.6985 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2125    0.7351   -0.3506 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9712    0.0240    0.1140 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1615    0.1950   -0.5053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2587    1.0914   -1.6803 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3791   -0.5087   -0.0416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4371    0.5286    0.3392 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6276   -0.2619    0.7938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7801   -0.1383    0.1711 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9373   -0.9370    0.6491 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8770    0.7933   -0.9822 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1787   -2.3273   -0.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8917   -0.8922    0.9417 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0508   -2.1079   -1.1977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8258    0.5350    1.7533 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5178    1.6681    0.5687 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6268    0.5487    1.3941 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9553   -1.0216   -1.4618 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9480    1.3878   -1.2119 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5083    1.3965    0.4621 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1122   -0.6185    0.9815 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4591    0.7205   -2.4366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0464    2.1485   -1.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2728    1.0650   -2.1397 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1265   -1.0671    0.8794 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7904   -1.1912   -0.8185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6519    1.0982   -0.5723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0369    1.1642    1.1420 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5623   -0.9442    1.6361 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5959   -1.8492    1.1556 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4526   -0.3035    1.4224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6261   -1.1279   -0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9157    0.8785   -1.3644 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1673    0.4781   -1.7799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5615    1.7964   -0.6479 H   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0
  6  5  1  0
  5  3  2  0
  3  4  1  0
  3  2  1  0
  2  1  2  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  3
 13 14  1  0
 13 15  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
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

Farnesene-alpha
  Mrv1652304022019442D          

 17 16  0  0  0  0            999 V2000
   -0.2858    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0003   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2858    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1432    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7147    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4292   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1437    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2866   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5721    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8581   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1437    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0010    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4287   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4287   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8576   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8576   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  1 14  2  0  0  0  0
  1  2  1  0  0  0  0
  1  3  1  4  0  0  0
 14  4  1  0  0  0  0
  2  5  1  0  0  0  0
  4 16  1  0  0  0  0
  5  6  1  0  0  0  0
 16  7  2  0  0  0  0
  6  8  2  0  0  0  0
  7  9  1  0  0  0  0
  7 10  1  4  0  0  0
  8 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 13  2  0  0  0  0
 14 15  1  4  0  0  0
 16 17  1  4  0  0  0
M  END
> <DATABASE_ID>
NP0330794

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]C(CC([H])=C(C)C=C)=C(C)CCC=C(C)C

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

> <INCHI_KEY>
CXENHBSYCFFKJS-UHFFFAOYSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
27.03811702102358

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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>
α-farnesene

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Farnesene-alpha                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  C   UNK     0      -0.533   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.867  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.533   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.134   0.000   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.201   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.535  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.801   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -5.868   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.135  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.801   1.540   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -7.202  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -5.868   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       7.469   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.800  -0.770   0.000  0.00  0.00           C+0
HETATM   15  H   UNK     0       0.800  -2.310   0.000  0.00  0.00           H+0
HETATM   16  C   UNK     0       3.468  -0.770   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       3.468  -2.310   0.000  0.00  0.00           H+0
CONECT    1   14    2    3                                                  
CONECT    2    1    5                                                       
CONECT    3    1                                                            
CONECT    4   14   16                                                       
CONECT    5    2    6                                                       
CONECT    6    5    8                                                       
CONECT    7   16    9   10                                                  
CONECT    8    6   11   12                                                  
CONECT    9    7   13                                                       
CONECT   10    7                                                            
CONECT   11    8                                                            
CONECT   12    8                                                            
CONECT   13    9                                                            
CONECT   14    1    4   15                                                  
CONECT   15   14                                                            
CONECT   16    4    7   17                                                  
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

View in JSmol

Synonyms

Value	Source
2,6,10-Trimethyldodeca-2,6,9,11-tetraene	ChEBI
3,7,11-Trimethyl-1,3,6,10-dodecatetraene	ChEBI
a-Farnesene	Generator
Α-farnesene	Generator

Chemical Formula

C₁₅H₂₄

Average Mass

204.3570 Da

Monoisotopic Mass

204.18780 Da

IUPAC Name

3,7,11-trimethyldodeca-1,3,6,10-tetraene

Traditional Name

α-farnesene

CAS Registry Number

Not Available

SMILES

[H]C(CC([H])=C(C)C=C)=C(C)CCC=C(C)C

InChI Identifier

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

InChI Key

CXENHBSYCFFKJS-UHFFFAOYSA-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
Blumea mollis	LOTUS Database	35616633
Buphthalmum salicifolium	LOTUS Database	35616633
Ceratitis capitata	LOTUS Database	35616633
Croton jacobinensis	LOTUS Database	35616633
Dumortiera hirsuta	LOTUS Database	35616633
Felicia filifolia	LOTUS Database	35616633
Haplocarpha scaposa	LOTUS Database	35616633
Helianthus tuberosus	LOTUS Database	35616633
Ligularia fischeri	LOTUS Database	35616633
Myrmica scabrinodis	LOTUS Database	35616633
Piper aduncum	LOTUS Database	35616633
Popillia japonica	LOTUS Database	35616633
Rugelia nudicaulis	LOTUS Database	35616633
Senecio inaequidens	LOTUS Database	35616633
Solenopsis invicta	LOTUS Database	35616633
Vismia cayennensis	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

farnesene (CHEBI:39236 )
a sesquiterpenoid (CPD-9338 )

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	27.04 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

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Farnesene

METLIN ID

Not Available

PubChem Compound

442368

PDB ID

Not Available

ChEBI ID

39236

Good Scents ID

Not Available

References

General References

LOTUS database [Link]

Showing NP-Card for α-farnesene (NP0330794)

MOL for NP0330794 (α-farnesene)

3D MOL for NP0330794 (α-farnesene)

3D SDF for NP0330794 (α-farnesene)

3D-SDF for NP0330794 (α-farnesene)

PDB for NP0330794 (α-farnesene)

3D PDB for NP0330794 (α-farnesene)

SMILES for NP0330794 (α-farnesene)

INCHI for NP0330794 (α-farnesene)

Structure for NP0330794 (α-farnesene)

3D Structure for NP0330794 (α-farnesene)