NP-MRD: Showing NP-Card for farnesyl acetone (NP0045000)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2022-03-10 18:52:31 UTC

Updated at

2022-03-10 22:20:41 UTC

NP-MRD ID

NP0045000

Secondary Accession Numbers

None

Natural Product Identification

Common Name

farnesyl acetone

Description

Farnesylacetone or (5E,9E)-Farnesylacetone, belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle. It is formally classified as an acyclic ketone although it is biochemically a diterpenoid as it is synthesized via isoprene units. Diterpenoids are biosynthesized by plants, animals and fungi via the HMG-CoA reductase pathway, with geranylgeranyl pyrophosphate being a primary intermediate. Four different Farnesylacetone isomers exist ((5E,9E)-Farnesylacetone, (5E,9Z)-Farnesylacetone, (5Z,9E)-Farnesylacetone, and (5Z,9Z)-Farnesylacetone) with the most common being (5E,9E)-Farnesylacetone. Farnesylacetone is a hydrophobic, neutral molecule that insoluble in water. It is used as a food additive and a cosmetic/perfuming agent. It has a fruity, floral, wine-like odor and is often used as a floral base for fruit and floral fragrances. Farnesylacetone is found naturally in a number of foods and plants including tomatoes, watermelon, yarrow and mushrooms. Farnesylacetone is also one of more than 140 terpenes that are found in cannabis plants (PMID: 6991645 ).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 49 48  0  0  0  0  0  0  0  0999 V2000
   -7.7034    0.9497    0.5050 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1505   -0.2643   -0.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8920   -1.0638   -0.6568 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6479   -0.4553   -0.1081 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0032    0.6585    0.6099 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5679    0.6896    0.7725 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6344   -0.1635    0.4375 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8026   -1.4837   -0.2055 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1910    0.1953    0.7633 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4558    0.2617   -0.5495 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9725    0.6073   -0.3744 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9118   -0.2064   -0.7811 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7102   -1.5143   -1.4469 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3517    0.2425   -0.5534 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9477   -0.8030    0.3239 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3228   -0.6545    0.7594 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1342    0.3288    0.5737 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9313    1.6064   -0.1310 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5349    0.1683    1.1728 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4461    0.9922    1.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8237    0.9893    0.4049 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3613    1.8952   -0.0034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3895   -0.4359   -1.2144 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4060   -1.4652    0.2514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4593    0.6581    1.6596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3677    1.6690    0.2233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1989    1.6300    1.2846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2296   -2.1683    0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3350   -1.4937   -1.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8082   -1.9808   -0.4311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1884    1.1362    1.3024 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7525   -0.6556    1.3302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5437   -0.6428   -1.1631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8729    1.0908   -1.2019 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2297    1.5417    0.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6655   -1.8591   -1.8926 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9531   -1.3991   -2.2713 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2729   -2.2180   -0.7257 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8093    0.1254   -1.5834 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3800    1.2648   -0.2071 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7681   -1.7848   -0.2079 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2629   -0.8703    1.2247 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7279   -1.5399    1.3463 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5694    1.4917   -1.1509 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3353    2.3096    0.4999 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9315    2.1427   -0.2586 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5579   -0.6518    1.8871 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1932   -0.0069    0.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7577    1.1361    1.6702 H   0  0  0  0  0  0  0  0  0  0  0  0
 18 17  1  0
 17 19  1  0
 17 16  2  3
 16 15  1  0
 15 14  1  0
 14 12  1  0
 12 13  1  0
 12 11  2  0
 11 10  1  0
 10  9  1  0
  9  7  1  0
  7  8  1  0
  7  6  2  0
  6  5  1  0
  5  4  1  0
  4  2  1  0
  2  1  1  0
  2  3  2  0
 18 44  1  0
 18 45  1  0
 18 46  1  0
 19 47  1  0
 19 48  1  0
 19 49  1  0
 16 43  1  0
 15 41  1  0
 15 42  1  0
 14 39  1  0
 14 40  1  0
 13 36  1  0
 13 37  1  0
 13 38  1  0
 11 35  1  0
 10 33  1  0
 10 34  1  0
  9 31  1  0
  9 32  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  6 27  1  0
  5 25  1  0
  5 26  1  0
  4 23  1  0
  4 24  1  0
  1 20  1  0
  1 21  1  0
  1 22  1  0
M  END


  Mrv1652303202019002D          

 19 18  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
    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
    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
    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 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4125   -2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -2.8579    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2375   -2.1434    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
    3.7125    0.7145    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
  1  2  1  0  0  0  0
  2  3  2  0  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  4  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  4  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 14 16  1  0  0  0  0
 10 17  1  0  0  0  0
  6 18  1  0  0  0  0
  2 19  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0045000

> <DATABASE_NAME>
NP-MRD

> <SMILES>
CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H30O/c1-15(2)9-6-10-16(3)11-7-12-17(4)13-8-14-18(5)19/h9,11,13H,6-8,10,12,14H2,1-5H3

> <INCHI_KEY>
LTUMRKDLVGQMJU-UHFFFAOYSA-N

> <FORMULA>
C18H30O

> <MOLECULAR_WEIGHT>
262.437

> <EXACT_MASS>
262.229665586

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
49

> <JCHEM_AVERAGE_POLARIZABILITY>
33.59011389870909

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
6,10,14-trimethylpentadeca-5,9,13-trien-2-one

> <ALOGPS_LOGP>
6.20

> <JCHEM_LOGP>
5.341389815333333

> <ALOGPS_LOGS>
-4.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.598762051814717

> <JCHEM_PKA_STRONGEST_BASIC>
-7.2778271430393975

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
87.62849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.16e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
6,10,14-trimethylpentadeca-5,9,13-trien-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 20-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   20-MAR-20         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       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.930   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.160   2.667   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.620   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -2.667   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.770  -4.001   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       0.000  -5.335   0.000  0.00  0.00           O+0
HETATM   16  C   UNK     0      -2.310  -4.001   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       2.310  -1.334   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       6.930   1.334   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.550   4.001   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3   19                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   18                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   17                                                  
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
CONECT   17   10                                                            
CONECT   18    6                                                            
CONECT   19    2                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   36    0
END

View in JSmol

Synonyms

Value	Source
Farnesylacetone, (e,e)-isomer	MeSH

Chemical Formula

C₁₈H₃₀O

Average Mass

262.4370 Da

Monoisotopic Mass

262.22967 Da

IUPAC Name

6,10,14-trimethylpentadeca-5,9,13-trien-2-one

Traditional Name

6,10,14-trimethylpentadeca-5,9,13-trien-2-one

CAS Registry Number

762-29-8

SMILES

CC(C)=CCCC(C)=CCCC(C)=CCCC(C)=O

InChI Identifier

InChI=1S/C18H30O/c1-15(2)9-6-10-16(3)11-7-12-17(4)13-8-14-18(5)19/h9,11,13H,6-8,10,12,14H2,1-5H3

InChI Key

LTUMRKDLVGQMJU-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, 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
Agrimonia pilosa	LOTUS Database	35616633
Bixa orellana	LOTUS Database	35616633
Cannabis sativa	NULL	Not Available
Carcinus maenas	Animalia	KNApSAcK
Cecropia pachystachya	LOTUS Database	35616633
Centaurea armena	Plant	KNApSAcK
Centaurea sessilis	Plant	KNApSAcK
Citrullus lanatus	LOTUS Database	35616633
Croton hutchinsonianus	LOTUS Database	35616633
Cystophora moniliformis	LOTUS Database	35616633
Daphne papyracea	LOTUS Database	35616633
Morina persica	LOTUS Database	35616633
Sargassum micracanthum	LOTUS Database	35616633
Scutellaria barbata	LOTUS Database	35616633
Tilia platyphyllos	LOTUS Database	35616633
Tipuana tipu	Plant	KNApSAcK
Tordylium apulum	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic diterpenoids. These are diterpenoids (compounds made of four consecutive isoprene units) that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Diterpenoids

Direct Parent

Acyclic diterpenoids

Alternative Parents

Substituents

Acyclic diterpenoid
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

a terpenoid derivative (CPD-12898 )

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	6.2	ALOGPS
logP	5.34	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	19.6	ChemAxon
pKa (Strongest Basic)	-7.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	87.63 m³·mol⁻¹	ChemAxon
Polarizability	33.59 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

Not Available

METLIN ID

Not Available

PubChem Compound

61206

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Showing NP-Card for farnesyl acetone (NP0045000)

MOL for NP0045000 (farnesyl acetone)

3D MOL for NP0045000 (farnesyl acetone)

3D SDF for NP0045000 (farnesyl acetone)

3D-SDF for NP0045000 (farnesyl acetone)

PDB for NP0045000 (farnesyl acetone)

3D PDB for NP0045000 (farnesyl acetone)

SMILES for NP0045000 (farnesyl acetone)

INCHI for NP0045000 (farnesyl acetone)

Structure for NP0045000 (farnesyl acetone)

3D Structure for NP0045000 (farnesyl acetone)