NP-MRD: Showing NP-Card for Amyl ketone (NP0084553)

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Record Information

Version

2.0

Created at

2022-04-29 05:15:36 UTC

Updated at

2022-04-29 05:15:37 UTC

NP-MRD ID

NP0084553

Secondary Accession Numbers

None

Natural Product Identification

Common Name

Amyl ketone

Description

6-Undecanone belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Thus, 6-undecanone is considered to be an oxygenated hydrocarbon lipid molecule. It has been investigated as a mosquito repellant, like DEET.2-Undecanone is a ketone that is soluble in organic solvents but insoluble in water. 6-Undecanone is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. Outside of the human body, 6-Undecanone has been detected, but not quantified in, herbs and spices. This could make 6-undecanone a potential biomarker for the consumption of these foods. Like most methyl ketones, 2-undecanone undergoes a haloform reaction when in the presence of a basic solution of hypochlorite. For example, the reaction between 2-undecanone and sodium hypochlorite yields sodium decanoate, chloroform, and sodium hydroxide. Typically, 1–2% concentrations of 2-undecanone are found in dog and cat repellents in the form of a liquid, aerosol spray, or gel. It is found naturally in bananas, cloves, ginger, guava, strawberries, wild-grown tomatoes, and the perennial Houttuynia cordata. It is usually produced synthetically, but it also be extracted from various plant sources. 2-Undecanone is also used in the perfumery and flavoring industries. Because of its strong odor it is primarily used as an insect repellent or animal repellent. It a colorless oil. Amyl ketone is found in Osmanthus fragrans . From oil of rue.

Structure

MOL 3D MOL SDF PDB SMILES InChI

     RDKit          3D

 34 33  0  0  0  0  0  0  0  0999 V2000
    5.2247    0.6330   -0.1928 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.6075   -0.7226   -0.1363 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1476   -0.6943    0.2438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3210    0.1085   -0.7446 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8811    0.0461   -0.2315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0421    0.7898   -1.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3686    1.3525   -2.0761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4699    0.8285   -0.7510 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7552    0.0487    0.5205 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2177    0.1043    0.8557 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0552   -0.4819   -0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5118   -0.3820    0.1890 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9987    1.0914   -1.1683 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9015    1.3110    0.6073 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3330    0.5123   -0.0841 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7193   -1.1945   -1.1329 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1258   -1.3689    0.5843 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7427   -1.7259    0.2196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0091   -0.2362    1.2366 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6034    1.1799   -0.7544 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4029   -0.3646   -1.7389 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8066    0.3618    0.8066 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5391   -1.0314   -0.2608 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8788    1.8591   -0.6916 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9997    0.2511   -1.5676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547    0.4887    1.3419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4277   -0.9979    0.3483 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4200   -0.4765    1.7723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5121    1.1694    0.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7992   -1.5374   -0.4650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9950    0.0955   -1.1971 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8348    0.6536   -0.0196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0841   -1.1485   -0.3666 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5745   -0.5225    1.2990 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
  1 13  1  0
  1 14  1  0
  1 15  1  0
  2 16  1  0
  2 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -5.954   3.437   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       7.383   3.437   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.620   2.667   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       6.049   2.667   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.286   3.437   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.716   3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.953   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.382   2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.619   3.437   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.048   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.715   2.667   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       0.715   1.127   0.000  0.00  0.00           O+0
CONECT    1    3                                                            
CONECT    2    4                                                            
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   11                                                       
CONECT   11    9   10   12                                                  
CONECT   12   11                                                            
MASTER        0    0    0    0    0    0    0    0   12    0   22    0
END

View in JSmol

Synonyms

Value	Source
(C11) Ketones	HMDB
6-Oxoundecane	HMDB
Amyl ketone	HMDB
Di-N-amyl ketone	HMDB
Diamyl ketone	HMDB
Dipentyl ketone	HMDB
Ketones, C11	HMDB
Pentyl ketone	HMDB
Undecan-6-one	HMDB
Undecanone-(6)	HMDB

Chemical Formula

C₁₁H₂₂O

Average Mass

170.2918 Da

Monoisotopic Mass

170.16707 Da

IUPAC Name

undecan-6-one

Traditional Name

6-undecanone

CAS Registry Number

Not Available

SMILES

CCCCCC(=O)CCCCC

InChI Identifier

InChI=1S/C11H22O/c1-3-5-7-9-11(12)10-8-6-4-2/h3-10H2,1-2H3

InChI Key

ZPQAKYPOZRXKFA-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
Osmanthus fragrans	Plant	KNApSAcK

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Organic oxide
Hydrocarbon derivative
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Oxygenated hydrocarbons (LMFA12000062 )

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	4.07	ALOGPS
logP	4.17	ChemAxon
logS	-3.8	ALOGPS
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	8	ChemAxon
Refractivity	53.05 m³·mol⁻¹	ChemAxon
Polarizability	22.47 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

HMDB0030943

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB002919

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

2-Undecanone

METLIN ID

Not Available

PubChem Compound

13561

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Not Available

Showing NP-Card for Amyl ketone (NP0084553)

MOL for NP0084553 (Amyl ketone)

3D MOL for NP0084553 (Amyl ketone)

3D SDF for NP0084553 (Amyl ketone)

3D-SDF for NP0084553 (Amyl ketone)

PDB for NP0084553 (Amyl ketone)

3D PDB for NP0084553 (Amyl ketone)

SMILES for NP0084553 (Amyl ketone)

INCHI for NP0084553 (Amyl ketone)

Structure for NP0084553 (Amyl ketone)

3D Structure for NP0084553 (Amyl ketone)