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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 05:34:01 UTC

Update Date

2021-09-24 05:34:01 UTC

HMDB ID

HMDB0303909

Secondary Accession Numbers

None

Metabolite Identification

Common Name

5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one

Description

(-)-Nootkatone 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. Based on a literature review very few articles have been published on (-)-Nootkatone.

Structure

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

HMDB0303909
     RDKit          3D
5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one
 38 39  0  0  0  0  0  0  0  0999 V2000
    2.8279    1.9532    0.9502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8329    0.8982    0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1299    0.3667   -0.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5786    0.2007   -0.2478 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7247   -1.2432    0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4694   -2.0618    0.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7553   -1.2382    0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7540   -1.7865    0.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0034   -1.0368    1.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1121   -1.5714    1.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7558    0.4442    1.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1146    0.8554   -0.0082 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1813    0.5531   -1.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8484    0.1417   -0.2932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6047    0.1542   -1.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3618    0.8595    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7444    2.4309    1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8968    2.3515    1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9916    0.8915    0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1828   -0.7449   -0.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1271    0.4769   -1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5914    0.2674   -1.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2575   -1.3122    1.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4445   -1.6912   -0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610   -2.5695   -0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5694   -2.8638    0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6923   -2.8102    1.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0924    0.6567    2.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7525    0.9102    1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9457    1.9589   -0.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2027    0.7078   -0.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1691   -0.5166   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1403    1.2585   -1.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1260    1.1247   -2.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5329    0.1122   -2.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0086   -0.7300   -2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3446    0.6694    1.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3557    1.9327    0.0546 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  6
 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  6
  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  1
 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

  Mrv1533007151515392D          

 18 19  0  0  1  0            999 V2000
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  1  0  0  0
 11  7  1  0  0  0  0
 12  5  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  6  0  0  0
 13  6  1  0  0  0  0
 13  8  2  0  0  0  0
 14  7  1  0  0  0  0
 14  8  1  0  0  0  0
 15  4  1  1  0  0  0
 15  9  1  0  0  0  0
 15 11  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
 11 17  1  6  0  0  0
 12 18  1  1  0  0  0
M  END
> <DATABASE_ID>
HMDB0303909

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(CCC2=CC(=O)C[C@]([H])(C)[C@@]2(C)C1)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/t11-,12-,15+/m0/s1

> <INCHI_KEY>
WTOYNNBCKUYIKC-SLEUVZQESA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.34

> <EXACT_MASS>
218.167065328

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
38

> <JCHEM_AVERAGE_POLARIZABILITY>
26.044266022988257

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S,4aR,6S)-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>
-4.825729591983801

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0303909
     RDKit          3D
5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one
 38 39  0  0  0  0  0  0  0  0999 V2000
    2.8279    1.9532    0.9502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8329    0.8982    0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1299    0.3667   -0.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5786    0.2007   -0.2478 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7247   -1.2432    0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4694   -2.0618    0.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7553   -1.2382    0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7540   -1.7865    0.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0034   -1.0368    1.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1121   -1.5714    1.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7558    0.4442    1.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1146    0.8554   -0.0082 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1813    0.5531   -1.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8484    0.1417   -0.2932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6047    0.1542   -1.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3618    0.8595    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7444    2.4309    1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8968    2.3515    1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9916    0.8915    0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1828   -0.7449   -0.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1271    0.4769   -1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5914    0.2674   -1.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2575   -1.3122    1.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4445   -1.6912   -0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610   -2.5695   -0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5694   -2.8638    0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6923   -2.8102    1.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0924    0.6567    2.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7525    0.9102    1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9457    1.9589   -0.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2027    0.7078   -0.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1691   -0.5166   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1403    1.2585   -1.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1260    1.1247   -2.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5329    0.1122   -2.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0086   -0.7300   -2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3446    0.6694    1.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3557    1.9327    0.0546 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  6
 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  6
  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  1
 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                                 15-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   15-JUL-15         0                                  
HETATM    1  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668   3.850   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       8.002   3.080   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   15                                                            
CONECT    5    6   12                                                       
CONECT    6    5   13                                                       
CONECT    7   11   14                                                       
CONECT    8   13   14                                                       
CONECT    9   12   15                                                       
CONECT   10    1    2   12                                                  
CONECT   11    3    7   15   17                                             
CONECT   12    5    9   10   18                                             
CONECT   13    6    8   15                                                  
CONECT   14    7    8   16                                                  
CONECT   15    4    9   11   13                                             
CONECT   16   14                                                            
CONECT   17   11                                                            
CONECT   18   12                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   38    0
END

COMPND    HMDB0303909
HETATM    1  C1  UNL     1       2.828   1.953   0.950  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.833   0.898   0.174  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.130   0.367  -0.313  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.579   0.201  -0.248  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.725  -1.243   0.095  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.469  -2.062   0.052  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.755  -1.238   0.241  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.754  -1.787   0.903  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.003  -1.037   1.135  1.00  0.00           C  
HETATM   10  O1  UNL     1      -4.112  -1.571   1.185  1.00  0.00           O  
HETATM   11  C10 UNL     1      -2.756   0.444   1.303  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.115   0.855  -0.008  1.00  0.00           C  
HETATM   13  C12 UNL     1      -3.181   0.553  -1.073  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.848   0.142  -0.293  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.605   0.154  -1.803  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.362   0.860   0.323  1.00  0.00           C  
HETATM   17  H1  UNL     1       3.744   2.431   1.234  1.00  0.00           H  
HETATM   18  H2  UNL     1       1.897   2.351   1.313  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.992   0.892   0.110  1.00  0.00           H  
HETATM   20  H4  UNL     1       4.183  -0.745  -0.134  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.127   0.477  -1.433  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.591   0.267  -1.373  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.257  -1.312   1.068  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.445  -1.691  -0.653  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.361  -2.569  -0.927  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.569  -2.864   0.811  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.692  -2.810   1.296  1.00  0.00           H  
HETATM   28  H12 UNL     1      -2.092   0.657   2.144  1.00  0.00           H  
HETATM   29  H13 UNL     1      -3.753   0.910   1.396  1.00  0.00           H  
HETATM   30  H14 UNL     1      -1.946   1.959  -0.033  1.00  0.00           H  
HETATM   31  H15 UNL     1      -4.203   0.708  -0.613  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.169  -0.517  -1.356  1.00  0.00           H  
HETATM   33  H17 UNL     1      -3.140   1.259  -1.908  1.00  0.00           H  
HETATM   34  H18 UNL     1      -0.126   1.125  -2.045  1.00  0.00           H  
HETATM   35  H19 UNL     1      -1.533   0.112  -2.388  1.00  0.00           H  
HETATM   36  H20 UNL     1      -0.009  -0.730  -2.126  1.00  0.00           H  
HETATM   37  H21 UNL     1       0.345   0.669   1.409  1.00  0.00           H  
HETATM   38  H22 UNL     1       0.356   1.933   0.055  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

HMDB0303909
     RDKit          3D
5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one
 38 39  0  0  0  0  0  0  0  0999 V2000
    2.8279    1.9532    0.9502 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8329    0.8982    0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1299    0.3667   -0.3128 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5786    0.2007   -0.2478 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.7247   -1.2432    0.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4694   -2.0618    0.0524 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7553   -1.2382    0.2413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7540   -1.7865    0.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0034   -1.0368    1.1354 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1121   -1.5714    1.1846 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7558    0.4442    1.3027 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1146    0.8554   -0.0082 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.1813    0.5531   -1.0733 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8484    0.1417   -0.2932 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.6047    0.1542   -1.8025 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3618    0.8595    0.3227 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7444    2.4309    1.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8968    2.3515    1.3126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9916    0.8915    0.1096 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1828   -0.7449   -0.1339 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1271    0.4769   -1.4326 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5914    0.2674   -1.3734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2575   -1.3122    1.0683 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4445   -1.6912   -0.6529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3610   -2.5695   -0.9267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5694   -2.8638    0.8112 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6923   -2.8102    1.2964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0924    0.6567    2.1435 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7525    0.9102    1.3955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9457    1.9589   -0.0333 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2027    0.7078   -0.6130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1691   -0.5166   -1.3564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1403    1.2585   -1.9081 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1260    1.1247   -2.0447 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5329    0.1122   -2.3876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0086   -0.7300   -2.1258 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3446    0.6694    1.4093 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3557    1.9327    0.0546 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  6
 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  6
  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  1
 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
Nootkatone	MeSH
Nootkatone, (4R-(4alpha,4aalpha,6beta))-isomer	MeSH

Chemical Formula

C₁₅H₂₂O

Average Molecular Weight

218.34

Monoisotopic Molecular Weight

218.167065328

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

[H][C@@]1(CCC2=CC(=O)C[C@]([H])(C)[C@@]2(C)C1)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/t11-,12-,15+/m0/s1

InChI Key

WTOYNNBCKUYIKC-SLEUVZQESA-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

Physiological effect

Organoleptic effect

Odor

Terpentine

Disposition

Source

Exogenous

Exogenous (HMDB: HMDB0303909)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular 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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
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	26.04 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
AllCCS	[M+H]+	151.756	32859911
AllCCS	[M+H-H2O]+	147.931	32859911
AllCCS	[M+Na]+	156.337	32859911
AllCCS	[M+NH4]+	155.313	32859911
AllCCS	[M-H]-	159.535	32859911
AllCCS	[M+Na-2H]-	159.99	32859911
AllCCS	[M+HCOO]-	160.597	32859911
DeepCCS	[M+H]+	156.187	30932474
DeepCCS	[M-H]-	153.829	30932474
DeepCCS	[M-2H]-	187.717	30932474
DeepCCS	[M+Na]+	162.731	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one,1TMS,isomer #1	C=C(C)[C@H]1CCC2=CC(O[Si](C)(C)C)=C[C@H](C)[C@@]2(C)C1	1920.6	Semi standard non polar	33892256
5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one,1TMS,isomer #1	C=C(C)[C@H]1CCC2=CC(O[Si](C)(C)C)=C[C@H](C)[C@@]2(C)C1	1805.9	Standard non polar	33892256
5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one,1TMS,isomer #1	C=C(C)[C@H]1CCC2=CC(O[Si](C)(C)C)=C[C@H](C)[C@@]2(C)C1	2074.9	Standard polar	33892256
5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one,1TBDMS,isomer #1	C=C(C)[C@H]1CCC2=CC(O[Si](C)(C)C(C)(C)C)=C[C@H](C)[C@@]2(C)C1	2160.1	Semi standard non polar	33892256
5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one,1TBDMS,isomer #1	C=C(C)[C@H]1CCC2=CC(O[Si](C)(C)C(C)(C)C)=C[C@H](C)[C@@]2(C)C1	2026.5	Standard non polar	33892256
5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one,1TBDMS,isomer #1	C=C(C)[C@H]1CCC2=CC(O[Si](C)(C)C(C)(C)C)=C[C@H](C)[C@@]2(C)C1	2224.0	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 10V, Positive-QTOF	splash10-014i-0190000000-c24752b1318a3a711643	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 20V, Positive-QTOF	splash10-017i-2930000000-3df119a56dd77df5e286	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 40V, Positive-QTOF	splash10-0gb9-9600000000-83e236a5978c0753f062	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 10V, Negative-QTOF	splash10-014i-0090000000-985cf431add494d4b1ca	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 20V, Negative-QTOF	splash10-014i-0090000000-301348660067d0dbf005	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 40V, Negative-QTOF	splash10-0ukm-1930000000-b1fc47101855e9adbab3	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 10V, Positive-QTOF	splash10-014i-0590000000-341a117f17f53ffe7f34	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 20V, Positive-QTOF	splash10-014i-1930000000-519467321c99880f1dba	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 40V, Positive-QTOF	splash10-001c-5900000000-6f03c86b1c9d475d2571	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 10V, Negative-QTOF	splash10-014i-0090000000-868e2fb00a2cfbf6c529	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 20V, Negative-QTOF	splash10-014i-0090000000-a67ecc985c1a2f05f9c1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one 40V, Negative-QTOF	splash10-015a-0930000000-7dec12d146ded38aa03b	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

FDB029762

KNApSAcK ID

Not Available

Chemspider ID

5884295

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7567181

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

Not Available

Showing metabocard for 5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one (HMDB0303909)

MOL for HMDB0303909 (5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one)

3D MOL for HMDB0303909 (5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one)

3D SDF for HMDB0303909 (5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one)

3D-SDF for HMDB0303909 (5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one)

PDB for HMDB0303909 (5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one)

3D PDB for HMDB0303909 (5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one)

SMILES for HMDB0303909 (5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one)

INCHI for HMDB0303909 (5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one)

Structure for HMDB0303909 (5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one)

3D Structure for HMDB0303909 (5,6-dimethyl-8-isopropenylbicyclo[4.4.0]dec-1-en-3-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra