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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 00:14:56 UTC

Update Date

2021-09-24 00:14:56 UTC

HMDB ID

HMDB0303214

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Dehydronootkatone

Description

(4R,4aS,6S)-4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6-hexahydronaphthalen-2-one 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 (4R,4aS,6S)-4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6-hexahydronaphthalen-2-one.

Structure

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

HMDB0303214
     RDKit          3D
Dehydronootkatone
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.9855    0.2377   -0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8132    0.7727   -0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6084    2.2093   -0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6994    0.0316    0.1440 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9490   -1.3414    0.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8743   -2.0402    0.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4203   -1.4008    0.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4532   -1.8779    1.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7685   -1.2030    1.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5827   -1.2549    2.4758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1468   -0.4483    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709   -0.4121   -0.6221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2369    0.5803   -1.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7038   -0.1644    0.1136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7904    1.0364    0.9980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961   -0.0136   -0.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8037    0.8362   -1.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1963   -0.8037   -0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5676    2.7555   -0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0312    2.6831    0.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0200    2.3080   -1.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3984    0.5963    1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9192   -1.8123    0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9657   -3.0579    1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3505   -2.7528    2.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5560    0.5596    0.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0008   -0.9675   -0.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9096   -1.4260   -1.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4013    0.6427   -2.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074    0.1728   -2.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5810    1.5620   -1.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8244    1.4129    1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1631    1.8417    0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3968    0.8383    2.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4439    0.8406   -1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5926   -0.9409   -1.3949 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  2  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  1
 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  1
  5 23  1  0
  6 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  6
 13 29  1  0
 13 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
M  END


  Mrv1533007131513492D          

 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  2  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  2  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  2  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  2  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  6  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  1  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  6  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  1  0  0  0
 12 18  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0303214

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@@]1(C)CC(=O)C=C2C=C[C@]([H])(C[C@@]12C)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h5-6,8,11-12H,1,7,9H2,2-4H3/t11-,12-,15+/m1/s1

> <INCHI_KEY>
PHRADXUJOZKVDN-JMSVASOKSA-N

> <FORMULA>
C15H20O

> <MOLECULAR_WEIGHT>
216.324

> <EXACT_MASS>
216.151415264

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
36

> <JCHEM_AVERAGE_POLARIZABILITY>
24.982050191693254

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4R,4aS,6S)-4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6-hexahydronaphthalen-2-one

> <ALOGPS_LOGP>
4.09

> <JCHEM_LOGP>
3.337915156

> <ALOGPS_LOGS>
-3.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.790472443021738

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
69.1871

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.32e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4R,4aS,6S)-4,4a-dimethyl-6-(prop-1-en-2-yl)-3,4,5,6-tetrahydronaphthalen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0303214
     RDKit          3D
Dehydronootkatone
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.9855    0.2377   -0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8132    0.7727   -0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6084    2.2093   -0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6994    0.0316    0.1440 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9490   -1.3414    0.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8743   -2.0402    0.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4203   -1.4008    0.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4532   -1.8779    1.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7685   -1.2030    1.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5827   -1.2549    2.4758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1468   -0.4483    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709   -0.4121   -0.6221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2369    0.5803   -1.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7038   -0.1644    0.1136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7904    1.0364    0.9980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961   -0.0136   -0.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8037    0.8362   -1.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1963   -0.8037   -0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5676    2.7555   -0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0312    2.6831    0.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0200    2.3080   -1.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3984    0.5963    1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9192   -1.8123    0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9657   -3.0579    1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3505   -2.7528    2.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5560    0.5596    0.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0008   -0.9675   -0.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9096   -1.4260   -1.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4013    0.6427   -2.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074    0.1728   -2.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5810    1.5620   -1.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8244    1.4129    1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1631    1.8417    0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3968    0.8383    2.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4439    0.8406   -1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5926   -0.9409   -1.3949 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  2  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  1
 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  1
  5 23  1  0
  6 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  6
 13 29  1  0
 13 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
M  END

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-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    HMDB0303214
HETATM    1  C1  UNL     1       3.986   0.238  -0.640  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.813   0.773  -0.417  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.608   2.209  -0.748  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.699   0.032   0.144  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.949  -1.341   0.599  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.874  -2.040   0.987  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.420  -1.401   0.927  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.453  -1.878   1.599  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.768  -1.203   1.520  1.00  0.00           C  
HETATM   10  O1  UNL     1      -3.583  -1.255   2.476  1.00  0.00           O  
HETATM   11  C10 UNL     1      -3.147  -0.448   0.298  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.971  -0.412  -0.622  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.237   0.580  -1.728  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.704  -0.164   0.114  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.790   1.036   0.998  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.496  -0.014  -0.797  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.804   0.836  -1.063  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.196  -0.804  -0.424  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.568   2.756  -0.847  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.031   2.683   0.076  1.00  0.00           H  
HETATM   21  H5  UNL     1       2.020   2.308  -1.671  1.00  0.00           H  
HETATM   22  H6  UNL     1       1.398   0.596   1.087  1.00  0.00           H  
HETATM   23  H7  UNL     1       2.919  -1.812   0.646  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.966  -3.058   1.337  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.350  -2.753   2.205  1.00  0.00           H  
HETATM   26  H10 UNL     1      -3.556   0.560   0.523  1.00  0.00           H  
HETATM   27  H11 UNL     1      -4.001  -0.967  -0.234  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.910  -1.426  -1.113  1.00  0.00           H  
HETATM   29  H13 UNL     1      -1.401   0.643  -2.439  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.107   0.173  -2.319  1.00  0.00           H  
HETATM   31  H15 UNL     1      -2.581   1.562  -1.349  1.00  0.00           H  
HETATM   32  H16 UNL     1      -1.824   1.413   1.155  1.00  0.00           H  
HETATM   33  H17 UNL     1      -0.163   1.842   0.566  1.00  0.00           H  
HETATM   34  H18 UNL     1      -0.397   0.838   2.017  1.00  0.00           H  
HETATM   35  H19 UNL     1       0.444   0.841  -1.467  1.00  0.00           H  
HETATM   36  H20 UNL     1       0.593  -0.941  -1.395  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    6   23
CONECT    6    7   24
CONECT    7    8    8   14
CONECT    8    9   25
CONECT    9   10   10   11
CONECT   11   12   26   27
CONECT   12   13   14   28
CONECT   13   29   30   31
CONECT   14   15   16
CONECT   15   32   33   34
CONECT   16   35   36
END

HMDB0303214
     RDKit          3D
Dehydronootkatone
 36 37  0  0  0  0  0  0  0  0999 V2000
    3.9855    0.2377   -0.6403 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8132    0.7727   -0.4171 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6084    2.2093   -0.7476 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6994    0.0316    0.1440 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.9490   -1.3414    0.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8743   -2.0402    0.9868 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4203   -1.4008    0.9274 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4532   -1.8779    1.5993 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7685   -1.2030    1.5200 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5827   -1.2549    2.4758 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1468   -0.4483    0.2977 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9709   -0.4121   -0.6221 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.2369    0.5803   -1.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7038   -0.1644    0.1136 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.7904    1.0364    0.9980 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4961   -0.0136   -0.7967 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8037    0.8362   -1.0630 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1963   -0.8037   -0.4245 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5676    2.7555   -0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0312    2.6831    0.0765 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0200    2.3080   -1.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3984    0.5963    1.0870 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9192   -1.8123    0.6457 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9657   -3.0579    1.3366 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3505   -2.7528    2.2053 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5560    0.5596    0.5229 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0008   -0.9675   -0.2339 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9096   -1.4260   -1.1129 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4013    0.6427   -2.4390 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1074    0.1728   -2.3189 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5810    1.5620   -1.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8244    1.4129    1.1545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1631    1.8417    0.5663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3968    0.8383    2.0166 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4439    0.8406   -1.4667 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5926   -0.9409   -1.3949 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  2  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  1
 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  1
  5 23  1  0
  6 24  1  0
  8 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  6
 13 29  1  0
 13 30  1  0
 13 31  1  0
 15 32  1  0
 15 33  1  0
 15 34  1  0
 16 35  1  0
 16 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₀O

Average Molecular Weight

216.324

Monoisotopic Molecular Weight

216.151415264

IUPAC Name

(4R,4aS,6S)-4,4a-dimethyl-6-(prop-1-en-2-yl)-2,3,4,4a,5,6-hexahydronaphthalen-2-one

Traditional Name

(4R,4aS,6S)-4,4a-dimethyl-6-(prop-1-en-2-yl)-3,4,5,6-tetrahydronaphthalen-2-one

CAS Registry Number

Not Available

SMILES

[H][C@@]1(C)CC(=O)C=C2C=C[C@]([H])(C[C@@]12C)C(C)=C

InChI Identifier

InChI=1S/C15H20O/c1-10(2)12-5-6-13-8-14(16)7-11(3)15(13,4)9-12/h5-6,8,11-12H,1,7,9H2,2-4H3/t11-,12-,15+/m1/s1

InChI Key

PHRADXUJOZKVDN-JMSVASOKSA-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

Not Available

Not Available

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	4.09	ALOGPS
logP	3.34	ChemAxon
logS	-3.8	ALOGPS
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	69.19 m³·mol⁻¹	ChemAxon
Polarizability	24.98 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]+	149.801	32859911
AllCCS	[M+H-H2O]+	145.878	32859911
AllCCS	[M+Na]+	154.502	32859911
AllCCS	[M+NH4]+	153.451	32859911
AllCCS	[M-H]-	157.833	32859911
AllCCS	[M+Na-2H]-	158.158	32859911
AllCCS	[M+HCOO]-	158.62	32859911
DeepCCS	[M-2H]-	187.111	30932474
DeepCCS	[M+Na]+	162.293	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dehydronootkatone,1TMS,isomer #1	C=C(C)[C@@H]1C=CC2=CC(O[Si](C)(C)C)=C[C@@H](C)[C@]2(C)C1	1941.0	Semi standard non polar	33892256
Dehydronootkatone,1TMS,isomer #1	C=C(C)[C@@H]1C=CC2=CC(O[Si](C)(C)C)=C[C@@H](C)[C@]2(C)C1	1787.7	Standard non polar	33892256
Dehydronootkatone,1TMS,isomer #1	C=C(C)[C@@H]1C=CC2=CC(O[Si](C)(C)C)=C[C@@H](C)[C@]2(C)C1	2188.1	Standard polar	33892256
Dehydronootkatone,1TBDMS,isomer #1	C=C(C)[C@@H]1C=CC2=CC(O[Si](C)(C)C(C)(C)C)=C[C@@H](C)[C@]2(C)C1	2216.7	Semi standard non polar	33892256
Dehydronootkatone,1TBDMS,isomer #1	C=C(C)[C@@H]1C=CC2=CC(O[Si](C)(C)C(C)(C)C)=C[C@@H](C)[C@]2(C)C1	2001.4	Standard non polar	33892256
Dehydronootkatone,1TBDMS,isomer #1	C=C(C)[C@@H]1C=CC2=CC(O[Si](C)(C)C(C)(C)C)=C[C@@H](C)[C@]2(C)C1	2345.9	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 - Dehydronootkatone 10V, Positive-QTOF	splash10-014i-0490000000-23bd148129982db2710c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronootkatone 20V, Positive-QTOF	splash10-016r-2940000000-6da01218c3959f4d8d2b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronootkatone 40V, Positive-QTOF	splash10-0gb9-9300000000-fc726327408d38d9f7db	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronootkatone 10V, Negative-QTOF	splash10-014i-0090000000-3b860c23029baac4c9e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronootkatone 20V, Negative-QTOF	splash10-014i-0190000000-d27e953b69458568565c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronootkatone 40V, Negative-QTOF	splash10-0002-1900000000-be22e472533588bb7eb3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronootkatone 10V, Positive-QTOF	splash10-014i-0590000000-82c5ad2c88b9d68b1624	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronootkatone 20V, Positive-QTOF	splash10-066r-0930000000-d651c03e94bc3bd50a93	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronootkatone 40V, Positive-QTOF	splash10-000f-9600000000-050706f98bfd8c1f2f5c	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronootkatone 10V, Negative-QTOF	splash10-014i-0090000000-93c59166c81b3b7c46b8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronootkatone 20V, Negative-QTOF	splash10-014i-0090000000-09293e9ff7df4bc98a6a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydronootkatone 40V, Negative-QTOF	splash10-03di-0890000000-549079ab489758e0ac67	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

FDB009276

KNApSAcK ID

C00054900

Chemspider ID

32701058

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

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 Dehydronootkatone (HMDB0303214)

MOL for HMDB0303214 (Dehydronootkatone)

3D MOL for HMDB0303214 (Dehydronootkatone)

3D SDF for HMDB0303214 (Dehydronootkatone)

3D-SDF for HMDB0303214 (Dehydronootkatone)

PDB for HMDB0303214 (Dehydronootkatone)

3D PDB for HMDB0303214 (Dehydronootkatone)

SMILES for HMDB0303214 (Dehydronootkatone)

INCHI for HMDB0303214 (Dehydronootkatone)

Structure for HMDB0303214 (Dehydronootkatone)

3D Structure for HMDB0303214 (Dehydronootkatone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra