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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-04-03 14:10:32 UTC

Update Date

2021-09-14 15:29:57 UTC

HMDB ID

HMDB0013687

Secondary Accession Numbers

HMDB13687

Metabolite Identification

Common Name

Nookatone

Description

Nootkatone is a natural organic compound and is the most important and expensive aromatic of grapefruit. It is a sesquiterpene and a ketone. Nootkatone was previously thought to be one of the main chemical components of the smell and flavour of grapefruits. In its solid form it is usually found as crystals. As a liquid, it is viscous and yellow. Nootkatone is typically extracted from grapefruit, but can also be manufactured with genetically modified organisms, or through the chemical or biochemical oxidation of valencene. It is also found in Alaska yellow cedar trees and vetiver grass.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

HMDB0013687
     RDKit          3D
Nookatone
 38 39  0  0  0  0  0  0  0  0999 V2000
    2.8268   -1.8732    0.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7453   -0.8530    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0256   -0.4928   -0.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4993   -0.0785   -0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7526    1.3732    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5219    2.2015    0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7430    1.5017    0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7827    2.1290   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0878    1.4897   -0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1379    2.1280   -0.8971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1558    0.0079   -0.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7538   -0.5735   -0.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8391   -2.0571   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9149    0.0858    0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6286    0.0705    1.7838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3992   -0.6433    0.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366   -2.1836    1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7811   -2.3941    1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8342    0.0620   -1.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6327    0.0611    0.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5632   -1.4240   -0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1943   -0.1922   -1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3969    1.4237    0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3714    1.7985   -0.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5218    2.6467    1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5334    3.0779   -0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7342    3.1781   -0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7037   -0.4212   -1.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6873   -0.3466    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3067   -0.2898   -1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7736   -2.3936   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9801   -2.3140    0.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0107   -2.6081   -0.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9769    0.5830    2.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7416   -0.9766    2.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5869    0.6308    1.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7124   -0.6067    1.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2966   -1.7271    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16  4  1  0
 14  7  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
M  END


  Mrv0541 02241219342D          

 16 17  0  0  0  0            999 V2000
   -0.6598    0.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1653    0.7420    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8243    1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4848    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021    0.0004    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416   -1.2371    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6497    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6598   -1.3198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7423   -0.4948    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4848   -0.2476    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4021    2.4747    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7416    1.9796    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.3921    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0827   -2.4747    0.0000 O   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  7  1  0  0  0  0
  2 11  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 16  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013687

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CC(=O)C=C2CCC(CC12C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3

> <INCHI_KEY>
WTOYNNBCKUYIKC-UHFFFAOYSA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.3346

> <EXACT_MASS>
218.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.102186863981856

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one

> <ALOGPS_LOGP>
3.89

> <JCHEM_LOGP>
3.699836812666668

> <ALOGPS_LOGS>
-3.88

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.911701752706282

> <JCHEM_PKA_STRONGEST_BASIC>
-4.825729591983798

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
68.0705

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.88e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
nootkatone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0013687
     RDKit          3D
Nookatone
 38 39  0  0  0  0  0  0  0  0999 V2000
    2.8268   -1.8732    0.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7453   -0.8530    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0256   -0.4928   -0.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4993   -0.0785   -0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7526    1.3732    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5219    2.2015    0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7430    1.5017    0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7827    2.1290   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0878    1.4897   -0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1379    2.1280   -0.8971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1558    0.0079   -0.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7538   -0.5735   -0.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8391   -2.0571   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9149    0.0858    0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6286    0.0705    1.7838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3992   -0.6433    0.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366   -2.1836    1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7811   -2.3941    1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8342    0.0620   -1.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6327    0.0611    0.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5632   -1.4240   -0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1943   -0.1922   -1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3969    1.4237    0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3714    1.7985   -0.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5218    2.6467    1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5334    3.0779   -0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7342    3.1781   -0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7037   -0.4212   -1.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6873   -0.3466    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3067   -0.2898   -1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7736   -2.3936   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9801   -2.3140    0.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0107   -2.6081   -0.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9769    0.5830    2.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7416   -0.9766    2.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5869    0.6308    1.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7124   -0.6067    1.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2966   -1.7271    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16  4  1  0
 14  7  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
M  END

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      -1.232   0.924   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   0.001   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.309   1.385   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.539   2.309   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.772   1.539   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.617   0.001   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.384  -0.769   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.384  -2.309   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.000  -3.079   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.232  -2.464   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.386  -0.924   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.772  -0.462   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.617   4.619   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.384   3.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   4.465   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       0.154  -4.619   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   11                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    2    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10   16                                                  
CONECT   10    9   11                                                       
CONECT   11    2   10   12                                                  
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14    4   13   15                                                  
CONECT   15   14                                                            
CONECT   16    9                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0013687
HETATM    1  C1  UNL     1       2.827  -1.873   0.895  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.745  -0.853   0.054  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.026  -0.493  -0.663  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.499  -0.079  -0.206  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.753   1.373   0.081  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.522   2.201   0.214  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.743   1.502   0.047  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.783   2.129  -0.466  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.088   1.490  -0.664  1.00  0.00           C  
HETATM   10  O1  UNL     1      -4.138   2.128  -0.897  1.00  0.00           O  
HETATM   11  C10 UNL     1      -3.156   0.008  -0.581  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.754  -0.573  -0.640  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.839  -2.057  -0.477  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.915   0.086   0.438  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.629   0.071   1.784  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.399  -0.643   0.627  1.00  0.00           C  
HETATM   17  H1  UNL     1       1.937  -2.184   1.445  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.781  -2.394   1.033  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.834   0.062  -1.588  1.00  0.00           H  
HETATM   20  H4  UNL     1       4.633   0.061   0.078  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.563  -1.424  -0.944  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.194  -0.192  -1.287  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.397   1.424   0.986  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.371   1.799  -0.757  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.522   2.647   1.251  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.533   3.078  -0.499  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.734   3.178  -0.779  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.704  -0.421  -1.451  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.687  -0.347   0.327  1.00  0.00           H  
HETATM   30  H14 UNL     1      -1.307  -0.290  -1.606  1.00  0.00           H  
HETATM   31  H15 UNL     1      -2.774  -2.394  -1.011  1.00  0.00           H  
HETATM   32  H16 UNL     1      -1.980  -2.314   0.580  1.00  0.00           H  
HETATM   33  H17 UNL     1      -1.011  -2.608  -0.963  1.00  0.00           H  
HETATM   34  H18 UNL     1      -0.977   0.583   2.504  1.00  0.00           H  
HETATM   35  H19 UNL     1      -1.742  -0.977   2.102  1.00  0.00           H  
HETATM   36  H20 UNL     1      -2.587   0.631   1.739  1.00  0.00           H  
HETATM   37  H21 UNL     1       0.712  -0.607   1.697  1.00  0.00           H  
HETATM   38  H22 UNL     1       0.297  -1.727   0.371  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3    4
CONECT    3   19   20   21
CONECT    4    5   16   22
CONECT    5    6   23   24
CONECT    6    7   25   26
CONECT    7    8    8   14
CONECT    8    9   27
CONECT    9   10   10   11
CONECT   11   12   28   29
CONECT   12   13   14   30
CONECT   13   31   32   33
CONECT   14   15   16
CONECT   15   34   35   36
CONECT   16   37   38
END

HMDB0013687
     RDKit          3D
Nookatone
 38 39  0  0  0  0  0  0  0  0999 V2000
    2.8268   -1.8732    0.8953 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7453   -0.8530    0.0536 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0256   -0.4928   -0.6631 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4993   -0.0785   -0.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7526    1.3732    0.0807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5219    2.2015    0.2136 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7430    1.5017    0.0468 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7827    2.1290   -0.4660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0878    1.4897   -0.6638 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1379    2.1280   -0.8971 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1558    0.0079   -0.5811 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7538   -0.5735   -0.6405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8391   -2.0571   -0.4771 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9149    0.0858    0.4380 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6286    0.0705    1.7838 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3992   -0.6433    0.6272 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9366   -2.1836    1.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7811   -2.3941    1.0325 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8342    0.0620   -1.5878 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6327    0.0611    0.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5632   -1.4240   -0.9442 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1943   -0.1922   -1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3969    1.4237    0.9862 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3714    1.7985   -0.7573 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5218    2.6467    1.2512 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5334    3.0779   -0.4987 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7342    3.1781   -0.7790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7037   -0.4212   -1.4511 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6873   -0.3466    0.3266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3067   -0.2898   -1.6062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7736   -2.3936   -1.0113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9801   -2.3140    0.5803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0107   -2.6081   -0.9633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9769    0.5830    2.5038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7416   -0.9766    2.1023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5869    0.6308    1.7395 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7124   -0.6067    1.6971 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2966   -1.7271    0.3709 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
 16  4  1  0
 14  7  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 15 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-5,6-Dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one	HMDB
4BetaH,5alpha-eremophila-1(10),11-dien-2-one	HMDB
4BetaH,5alpha-eremorphila-1(10)11-dien-2-one	HMDB
Nootkatane	HMDB
Nootkatone, (4R-(4alpha,4aalpha,6beta))-isomer	MeSH

Chemical Formula

C₁₅H₂₂O

Average Molecular Weight

218.3346

Monoisotopic Molecular Weight

218.167065326

IUPAC Name

4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one

Traditional Name

nootkatone

CAS Registry Number

4674-50-4

SMILES

CC1CC(=O)C=C2CCC(CC12C)C(C)=C

InChI Identifier

InChI=1S/C15H22O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h8,11-12H,1,5-7,9H2,2-4H3

InChI Key

WTOYNNBCKUYIKC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids. These are sesquiterpenoids with a structure based either on the eremophilane skeleton, its 8,9-seco derivative, or the furoeremophilane skeleton. Eremophilanes have been shown to be derived from eudesmanes by migration of the methyl group at C-10 to C-5.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eremophilane, 8,9-secoeremophilane and furoeremophilane sesquiterpenoids

Alternative Parents

Substituents

Eremophilane sesquiterpenoid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Cellular substructure

Membrane (HMDB: HMDB0013687)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0013687)

Source

Endogenous

Endogenous (HMDB: HMDB0013687)

Animal

Animal (HMDB: HMDB0013687)

Exogenous

Food

Food (HMDB: HMDB0013687)

Fruit

Citrus

Grapefruit (FooDB: FOOD00256)
Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Citrus (FooDB: FOOD00859)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0013687)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0013687)

Cellular process

Cell signaling (HMDB: HMDB0013687)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0013687)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	36 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.029 g/L	ALOGPS
logP	3.89	ALOGPS
logP	3.7	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	18.91	ChemAxon
pKa (Strongest Basic)	-4.8	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	1	ChemAxon
Refractivity	68.07 m³·mol⁻¹	ChemAxon
Polarizability	26.1 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	153.768	31661259
DarkChem	[M-H]-	150.979	31661259
DeepCCS	[M-2H]-	185.167	30932474
DeepCCS	[M+Na]+	160.261	30932474
AllCCS	[M+H]+	151.6	32859911
AllCCS	[M+H-H2O]+	147.7	32859911
AllCCS	[M+NH4]+	155.2	32859911
AllCCS	[M+Na]+	156.2	32859911
AllCCS	[M-H]-	159.5	32859911
AllCCS	[M+Na-2H]-	160.0	32859911
AllCCS	[M+HCOO]-	160.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Nookatone	CC1CC(=O)C=C2CCC(CC12C)C(C)=C	2566.9	Standard polar	33892256
Nookatone	CC1CC(=O)C=C2CCC(CC12C)C(C)=C	1753.8	Standard non polar	33892256
Nookatone	CC1CC(=O)C=C2CCC(CC12C)C(C)=C	1812.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Nookatone,1TMS,isomer #1	C=C(C)C1CCC2=CC(O[Si](C)(C)C)=CC(C)C2(C)C1	1914.5	Semi standard non polar	33892256
Nookatone,1TMS,isomer #1	C=C(C)C1CCC2=CC(O[Si](C)(C)C)=CC(C)C2(C)C1	1778.8	Standard non polar	33892256
Nookatone,1TMS,isomer #1	C=C(C)C1CCC2=CC(O[Si](C)(C)C)=CC(C)C2(C)C1	2084.1	Standard polar	33892256
Nookatone,1TBDMS,isomer #1	C=C(C)C1CCC2=CC(O[Si](C)(C)C(C)(C)C)=CC(C)C2(C)C1	2164.1	Semi standard non polar	33892256
Nookatone,1TBDMS,isomer #1	C=C(C)C1CCC2=CC(O[Si](C)(C)C(C)(C)C)=CC(C)C2(C)C1	2006.0	Standard non polar	33892256
Nookatone,1TBDMS,isomer #1	C=C(C)C1CCC2=CC(O[Si](C)(C)C(C)(C)C)=CC(C)C2(C)C1	2232.5	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Nookatone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fbi-1910000000-b45e411b466c6a4f701e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nookatone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nookatone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Nookatone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nookatone 10V, Positive-QTOF	splash10-014i-0190000000-c24752b1318a3a711643	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nookatone 20V, Positive-QTOF	splash10-017i-2930000000-22f4dc6376ca69ed6b2a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nookatone 40V, Positive-QTOF	splash10-0gb9-9700000000-fc684e09e444485e471b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nookatone 10V, Negative-QTOF	splash10-014i-0090000000-985cf431add494d4b1ca	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nookatone 20V, Negative-QTOF	splash10-014i-0090000000-9295b5b0acc45864f5c2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nookatone 40V, Negative-QTOF	splash10-0f79-0930000000-b1395e8a051a4ce6d609	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nookatone 10V, Negative-QTOF	splash10-014i-0090000000-868e2fb00a2cfbf6c529	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nookatone 20V, Negative-QTOF	splash10-014i-0090000000-868e2fb00a2cfbf6c529	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nookatone 40V, Negative-QTOF	splash10-014i-0890000000-6acaaae614c8694f91a8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nookatone 10V, Positive-QTOF	splash10-016r-0890000000-0186d1632d3974cab9e4	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nookatone 20V, Positive-QTOF	splash10-05br-1910000000-7e41e7df099107da9183	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Nookatone 40V, Positive-QTOF	splash10-0006-9200000000-451c0b277f60bba512c6	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB014799

KNApSAcK ID

C00016987

Chemspider ID

19575

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Nootkatone

METLIN ID

Not Available

PubChem Compound

20797

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Nookatone (HMDB0013687)

MOL for HMDB0013687 (Nookatone)

3D MOL for HMDB0013687 (Nookatone)

3D SDF for HMDB0013687 (Nookatone)

3D-SDF for HMDB0013687 (Nookatone)

PDB for HMDB0013687 (Nookatone)

3D PDB for HMDB0013687 (Nookatone)

SMILES for HMDB0013687 (Nookatone)

INCHI for HMDB0013687 (Nookatone)

Structure for HMDB0013687 (Nookatone)

3D Structure for HMDB0013687 (Nookatone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra