NP-MRD: Showing NP-Card for geranylacetone (NP0300208)

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Record Information

Version

2.0

Created at

2022-09-10 12:28:53 UTC

Updated at

2022-09-10 12:28:53 UTC

NP-MRD ID

NP0300208

Secondary Accession Numbers

None

Natural Product Identification

Common Name

geranylacetone

Description

Geranyl acetone belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle. Thus, geranyl acetone is considered to be a hydrocarbon lipid molecule. geranylacetone is found in Anthemis aciphylla, Arum maculatum, Avena sativa, Bellis perennis, Bothriochloa bladhii, Calendula officinalis, Cannabis sativa, Catharanthus roseus, Cecropia pachystachya, Cichorium endivia, Citrullus lanatus, Conyza bonariensis, Cystophora moniliformis, Daphne papyracea, Daucus carota, Hamamelis virginiana, Helianthus annuus, Ilex paraguariensis, Lonicera japonica, Monteverdia ilicifolia, Persicaria minor, Polygala senega, Prunus dulcis, Santalum spicatum, Scutellaria baicalensis, Senna alexandrina, Vachellia rigidula, Zea mays and Zingiber mioga. geranylacetone was first documented in 2001 (PMID: 11166310). Geranyl acetone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral (PMID: 19500173) (PMID: 19919095) (PMID: 20127888) (PMID: 20491081).

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 36 35  0  0  0  0  0  0  0  0999 V2000
    5.0313    0.0740    1.0216 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8047   -0.3375   -0.3714 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7370   -0.6911   -1.0733 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3937   -0.3305   -0.9723 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4712    0.0614    0.0912 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0485    0.1618   -0.0825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3257   -0.1521   -1.1218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9537   -0.7245   -2.3384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1932    0.0368   -1.1024 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6823    0.5870    0.1982 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1555    0.7278    0.0887 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9377    0.0687    0.9194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4217    0.1842    0.8402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3517   -0.8230    1.9750 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4709   -0.5696    1.7292 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1128   -0.1101    1.2952 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8463    1.1723    1.1945 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5129    0.5026   -1.7427 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3045   -1.3222   -1.4113 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6211   -0.7144    0.9351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9185    0.9757    0.5995 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4217    0.5674    0.7786 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6689   -0.1030   -2.8533 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2276   -1.8072   -2.2199 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0922   -0.8116   -3.0974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6239   -0.9364   -1.3233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3713    0.8027   -1.8854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2717    1.5850    0.4350 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4463   -0.1016    1.0403 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5660    1.3648   -0.6665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8351   -0.8347    1.0548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7558    0.8891    1.6114 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7422    0.4836   -0.1599 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7113   -0.1980    2.6342 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1405   -1.3324    2.5389 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7571   -1.6095    1.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 12  1  0
 12 14  1  0
 12 11  2  3
 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
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 11 30  1  0
 10 28  1  0
 10 29  1  0
  9 26  1  0
  9 27  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  6 22  1  0
  5 20  1  0
  5 21  1  0
  4 18  1  0
  4 19  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
M  END

geranyl acetone
  Mrv1572001071617082D          

 14 13  0  0  0  0            999 V2000
    4.5375    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
    5.7750    2.8579    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5375    3.5724    0.0000 O   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    2.1434    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
   -0.4125    0.7145    0.0000 C   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
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  7  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 12 14  1  0  0  0  0
  1  5  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0300208

> <DATABASE_NAME>
NP-MRD

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H22O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h7,9H,5-6,8,10H2,1-4H3/b12-9+

> <INCHI_KEY>
HNZUNIKWNYHEJJ-FMIVXFBMSA-N

> <FORMULA>
C13H22O

> <MOLECULAR_WEIGHT>
194.318

> <EXACT_MASS>
194.167065328

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
24.90987585771945

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5E)-6,10-dimethylundeca-5,9-dien-2-one

> <ALOGPS_LOGP>
4.59

> <JCHEM_LOGP>
3.6816755403333334

> <ALOGPS_LOGS>
-3.31

> <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>
63.8259

> <JCHEM_ROTATABLE_BOND_COUNT>
6

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.42e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
geranylacetone

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 07-JAN-16   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: geranyl acetone                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JAN-16         0                                  
HETATM    1  C   UNK     0       8.470   4.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.240   5.335   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.780   5.335   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0       8.470   6.668   0.000  0.00  0.00           O+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   4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.850   1.334   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.310   1.334   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.540   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.770  -1.334   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.770   1.334   0.000  0.00  0.00           C+0
CONECT    1    2    5                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2                                                            
CONECT    5    6    1                                                       
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                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   26    0
END

View in JSmol

Synonyms

Value	Source
(e)-6,10-Dimethyl-5,9-undecadien-2-one	ChEBI
(e)-6,10-Dimethylundeca-5,9-dien-2-one	ChEBI
Geranylacetone	ChEBI
trans-Geranylacetone	ChEBI
Geranylacetone, (e)-isomer	MeSH

Chemical Formula

C₁₃H₂₂O

Average Mass

194.3180 Da

Monoisotopic Mass

194.16707 Da

IUPAC Name

(5E)-6,10-dimethylundeca-5,9-dien-2-one

Traditional Name

geranylacetone

CAS Registry Number

Not Available

SMILES

CC(C)=CCC\C(C)=C\CCC(C)=O

InChI Identifier

InChI=1S/C13H22O/c1-11(2)7-5-8-12(3)9-6-10-13(4)14/h7,9H,5-6,8,10H2,1-4H3/b12-9+

InChI Key

HNZUNIKWNYHEJJ-FMIVXFBMSA-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
Anthemis aciphylla	LOTUS Database	35616633
Arum maculatum	LOTUS Database	35616633
Avena sativa	LOTUS Database	35616633
Bellis perennis	LOTUS Database	35616633
Bothriochloa bladhii	LOTUS Database	35616633
Calendula officinalis	LOTUS Database	35616633
Cannabis sativa	LOTUS Database	35616633
Catharanthus roseus	LOTUS Database	35616633
Cecropia pachystachya	LOTUS Database	35616633
Cichorium endivia	LOTUS Database	35616633
Citrullus lanatus	LOTUS Database	35616633
Conyza bonariensis	LOTUS Database	35616633
Cystophora moniliformis	LOTUS Database	35616633
Daphne papyracea	LOTUS Database	35616633
Daucus carota	LOTUS Database	35616633
Hamamelis virginiana	LOTUS Database	35616633
Helianthus annuus	LOTUS Database	35616633
Ilex paraguariensis	LOTUS Database	35616633
Lonicera japonica	LOTUS Database	35616633
Monteverdia ilicifolia	LOTUS Database	35616633
Persicaria minor	LOTUS Database	35616633
Polygala senega	LOTUS Database	35616633
Prunus dulcis	LOTUS Database	35616633
Santalum spicatum	LOTUS Database	35616633
Scutellaria baicalensis	LOTUS Database	35616633
Senna alexandrina	LOTUS Database	35616633
Vachellia rigidula	LOTUS Database	35616633
Zea mays	LOTUS Database	35616633
Zingiber mioga	LOTUS Database	35616633

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as acyclic monoterpenoids. These are monoterpenes that do not contain a cycle.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Acyclic monoterpenoids

Alternative Parents

Substituents

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

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

monoterpene ketone (CHEBI:67206 )
Hydrocarbons (LMFA11000696 )

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	4.59	ALOGPS
logP	3.68	ChemAxon
logS	-3.3	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	6	ChemAxon
Refractivity	63.83 m³·mol⁻¹	ChemAxon
Polarizability	24.91 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

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

1549778

PDB ID

Not Available

ChEBI ID

67206

Good Scents ID

Not Available

References

General References

Meijerink J, Braks MA, Van Loon JJ: Olfactory receptors on the antennae of the malaria mosquito Anopheles gambiae are sensitive to ammonia and other sweat-borne components. J Insect Physiol. 2001 Apr;47(4-5):455-64. doi: 10.1016/s0022-1910(00)00136-0. [PubMed:11166310 ]
Petrick L, Dubowski Y: Heterogeneous oxidation of squalene film by ozone under various indoor conditions. Indoor Air. 2009 Oct;19(5):381-91. doi: 10.1111/j.1600-0668.2009.00599.x. Epub 2009 Feb 13. [PubMed:19500173 ]
Huang B, Ban X, He J, Tong J, Tian J, Wang Y: Comparative analysis of essential oil components and antioxidant activity of extracts of Nelumbo nucifera from various areas of China. J Agric Food Chem. 2010 Jan 13;58(1):441-8. doi: 10.1021/jf902643e. [PubMed:19919095 ]
Kaufman PE, Mann RS, Butler JF: Evaluation of semiochemical toxicity to Aedes aegypti, Ae. albopictus and Anopheles quadrimaculatus (Diptera: Culicidae). Pest Manag Sci. 2010 May;66(5):497-504. doi: 10.1002/ps.1899. [PubMed:20127888 ]
Medini H, Elaissi A, Khouja ML, Chraief I, Farhat F, Hammami M, Chemli R, Harzallah-Skhiri F: Leaf essential oil of Juniperus oxycedrus L. (Cupressaceae) harvested in northern Tunisia: composition and intra-specific variability. Chem Biodivers. 2010 May;7(5):1254-66. doi: 10.1002/cbdv.200900241. [PubMed:20491081 ]
LOTUS database [Link]

Showing NP-Card for geranylacetone (NP0300208)

MOL for NP0300208 (geranylacetone)

3D MOL for NP0300208 (geranylacetone)

3D SDF for NP0300208 (geranylacetone)

3D-SDF for NP0300208 (geranylacetone)

PDB for NP0300208 (geranylacetone)

3D PDB for NP0300208 (geranylacetone)

SMILES for NP0300208 (geranylacetone)

INCHI for NP0300208 (geranylacetone)

Structure for NP0300208 (geranylacetone)

3D Structure for NP0300208 (geranylacetone)