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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:35:13 UTC

Update Date

2022-03-07 02:54:55 UTC

HMDB ID

HMDB0036446

Secondary Accession Numbers

HMDB36446

Metabolite Identification

Common Name

beta-Kessyl ketone

Description

(4alpha,10alpha)-1(5),6-Guaiadiene, also known as (4α,10α)-1(5),6-guaiadiene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units (4alpha,10alpha)-1(5),6-Guaiadiene is possibly neutral.

Structure

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

HMDB0036446
     RDKit          3D
beta-Kessyl ketone
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.2916    1.9125   -0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099    1.2071    0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3516    0.0983    0.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4597   -1.0414   -0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7677   -1.8005   -1.0508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981   -0.9175    0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0201    0.5644    0.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1111    0.8816   -0.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2536   -0.0632   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765    0.6299    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9387    1.5143   -0.9364 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6032    1.3570    1.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4442   -0.9520   -1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1898   -1.8224   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1009   -1.6986    0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841   -3.0540    1.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0105   -1.0485    0.9303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5046    2.6661   -0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2149    1.1667   -1.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3082    2.3800   -1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6516    1.9330    1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1372    0.3103   -0.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7603   -0.1579    1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6119   -1.2235    1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7202    0.8722    1.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2866    0.7388   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3993    1.9462   -0.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3469   -0.1740    0.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0747    2.0501   -1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3780    0.9020   -1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7218    2.2453   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6835    1.1822    2.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4727    1.0870    2.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7298    2.4450    1.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4168   -0.3708   -2.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3614   -1.5214   -1.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658   -1.3728   -1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -2.8435   -1.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5246   -2.8343    2.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8341   -3.4746    1.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9061   -3.7194    0.5143 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  7  2  1  0
 17  9  1  0
 15  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
M  END


  Mrv0541 02241207412D          

 17 19  0  0  0  0            999 V2000
    0.5287    0.2465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3171    0.3171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8109   -0.3876    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5163   -0.1061    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2217   -0.5287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5163    0.6698    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7403    0.9520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5287    1.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2217   -0.8814    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5868   -0.3171    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8690    0.4581    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0930   -1.5868    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3876   -1.0930    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1055   -1.7279    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8814   -1.4458    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8109   -0.5287    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1055   -0.5287    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 16  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  3  4  1  0  0  0  0
  3 13  1  0  0  0  0
  4  5  2  0  0  0  0
  4  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 17  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036446

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C12CCC(C)(O1)C1C(C2)C(C)CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-9(2)15-6-5-14(4,17-15)13-11(8-15)10(3)7-12(13)16/h9-11,13H,5-8H2,1-4H3

> <INCHI_KEY>
CSLBUZGPLRECOR-UHFFFAOYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.3499

> <EXACT_MASS>
236.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.495627618446363

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,5-dimethyl-8-(propan-2-yl)-11-oxatricyclo[6.2.1.0²,⁶]undecan-3-one

> <ALOGPS_LOGP>
2.72

> <JCHEM_LOGP>
3.0234526993333333

> <ALOGPS_LOGS>
-3.68

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.657952843950444

> <JCHEM_PKA_STRONGEST_BASIC>
-4.214603091312701

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
67.2658

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.91e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
8-isopropyl-1,5-dimethyl-11-oxatricyclo[6.2.1.0²,⁶]undecan-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036446
     RDKit          3D
beta-Kessyl ketone
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.2916    1.9125   -0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099    1.2071    0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3516    0.0983    0.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4597   -1.0414   -0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7677   -1.8005   -1.0508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981   -0.9175    0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0201    0.5644    0.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1111    0.8816   -0.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2536   -0.0632   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765    0.6299    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9387    1.5143   -0.9364 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6032    1.3570    1.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4442   -0.9520   -1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1898   -1.8224   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1009   -1.6986    0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841   -3.0540    1.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0105   -1.0485    0.9303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5046    2.6661   -0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2149    1.1667   -1.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3082    2.3800   -1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6516    1.9330    1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1372    0.3103   -0.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7603   -0.1579    1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6119   -1.2235    1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7202    0.8722    1.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2866    0.7388   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3993    1.9462   -0.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3469   -0.1740    0.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0747    2.0501   -1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3780    0.9020   -1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7218    2.2453   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6835    1.1822    2.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4727    1.0870    2.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7298    2.4450    1.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4168   -0.3708   -2.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3614   -1.5214   -1.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658   -1.3728   -1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -2.8435   -1.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5246   -2.8343    2.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8341   -3.4746    1.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9061   -3.7194    0.5143 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  7  2  1  0
 17  9  1  0
 15  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  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       0.987   0.460   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.592   0.592   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.514  -0.724   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.830  -0.198   0.000  0.00  0.00           C+0
HETATM    5  O   UNK     0      -4.147  -0.987   0.000  0.00  0.00           O+0
HETATM    6  C   UNK     0      -2.830   1.250   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.382   1.777   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.987   3.225   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.147  -1.645   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.962  -0.592   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.489   0.855   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.040  -2.962   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.724  -2.040   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.197  -3.225   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.645  -2.699   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.514  -0.987   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.197  -0.987   0.000  0.00  0.00           O+0
CONECT    1    2   16                                                       
CONECT    2    1    3    7                                                  
CONECT    3    2    4   13                                                  
CONECT    4    3    5    6                                                  
CONECT    5    4                                                            
CONECT    6    4    7                                                       
CONECT    7    2    6    8                                                  
CONECT    8    7                                                            
CONECT    9   10                                                            
CONECT   10    9   11   16                                                  
CONECT   11   10                                                            
CONECT   12   13                                                            
CONECT   13    3   12   14   17                                             
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16    1   10   15   17                                             
CONECT   17   13   16                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0036446
HETATM    1  C1  UNL     1      -2.292   1.912  -0.951  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.310   1.207   0.375  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.352   0.098   0.273  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.460  -1.041  -0.166  1.00  0.00           C  
HETATM    5  O1  UNL     1      -2.768  -1.800  -1.051  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.298  -0.917   0.707  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.020   0.564   0.740  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.111   0.882  -0.211  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.254  -0.063  -0.026  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.577   0.630   0.214  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.939   1.514  -0.936  1.00  0.00           C  
HETATM   12  C11 UNL     1       2.603   1.357   1.535  1.00  0.00           C  
HETATM   13  C12 UNL     1       1.444  -0.952  -1.266  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.190  -1.822  -1.109  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.101  -1.699   0.339  1.00  0.00           C  
HETATM   16  C15 UNL     1      -0.184  -3.054   1.040  1.00  0.00           C  
HETATM   17  O2  UNL     1       1.011  -1.048   0.930  1.00  0.00           O  
HETATM   18  H1  UNL     1      -1.505   2.666  -0.955  1.00  0.00           H  
HETATM   19  H2  UNL     1      -2.215   1.167  -1.776  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.308   2.380  -1.075  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.652   1.933   1.140  1.00  0.00           H  
HETATM   22  H5  UNL     1      -4.137   0.310  -0.446  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.760  -0.158   1.285  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.612  -1.223   1.741  1.00  0.00           H  
HETATM   25  H8  UNL     1      -0.720   0.872   1.758  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.287   0.739  -1.238  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.399   1.946  -0.120  1.00  0.00           H  
HETATM   28  H11 UNL     1       3.347  -0.174   0.275  1.00  0.00           H  
HETATM   29  H12 UNL     1       2.075   2.050  -1.369  1.00  0.00           H  
HETATM   30  H13 UNL     1       3.378   0.902  -1.755  1.00  0.00           H  
HETATM   31  H14 UNL     1       3.722   2.245  -0.625  1.00  0.00           H  
HETATM   32  H15 UNL     1       1.684   1.182   2.127  1.00  0.00           H  
HETATM   33  H16 UNL     1       3.473   1.087   2.165  1.00  0.00           H  
HETATM   34  H17 UNL     1       2.730   2.445   1.290  1.00  0.00           H  
HETATM   35  H18 UNL     1       1.417  -0.371  -2.189  1.00  0.00           H  
HETATM   36  H19 UNL     1       2.361  -1.521  -1.091  1.00  0.00           H  
HETATM   37  H20 UNL     1      -0.566  -1.373  -1.776  1.00  0.00           H  
HETATM   38  H21 UNL     1       0.429  -2.844  -1.439  1.00  0.00           H  
HETATM   39  H22 UNL     1      -0.525  -2.834   2.073  1.00  0.00           H  
HETATM   40  H23 UNL     1       0.834  -3.475   1.048  1.00  0.00           H  
HETATM   41  H24 UNL     1      -0.906  -3.719   0.514  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    7   21
CONECT    3    4   22   23
CONECT    4    5    5    6
CONECT    6    7   15   24
CONECT    7    8   25
CONECT    8    9   26   27
CONECT    9   10   13   17
CONECT   10   11   12   28
CONECT   11   29   30   31
CONECT   12   32   33   34
CONECT   13   14   35   36
CONECT   14   15   37   38
CONECT   15   16   17
CONECT   16   39   40   41
END

HMDB0036446
     RDKit          3D
beta-Kessyl ketone
 41 43  0  0  0  0  0  0  0  0999 V2000
   -2.2916    1.9125   -0.9513 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3099    1.2071    0.3751 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3516    0.0983    0.2732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4597   -1.0414   -0.1664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7677   -1.8005   -1.0508 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2981   -0.9175    0.7069 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0201    0.5644    0.7402 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1111    0.8816   -0.2108 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2536   -0.0632   -0.0262 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5765    0.6299    0.2141 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9387    1.5143   -0.9364 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6032    1.3570    1.5347 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4442   -0.9520   -1.2665 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1898   -1.8224   -1.1091 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1009   -1.6986    0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1841   -3.0540    1.0403 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0105   -1.0485    0.9303 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5046    2.6661   -0.9553 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2149    1.1667   -1.7755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3082    2.3800   -1.0748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6516    1.9330    1.1401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1372    0.3103   -0.4457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7603   -0.1579    1.2848 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6119   -1.2235    1.7410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7202    0.8722    1.7577 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2866    0.7388   -1.2379 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3993    1.9462   -0.1202 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3469   -0.1740    0.2748 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0747    2.0501   -1.3689 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3780    0.9020   -1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7218    2.2453   -0.6253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6835    1.1822    2.1274 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4727    1.0870    2.1647 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7298    2.4450    1.2901 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4168   -0.3708   -2.1888 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3614   -1.5214   -1.0912 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5658   -1.3728   -1.7757 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4292   -2.8435   -1.4385 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5246   -2.8343    2.0729 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8341   -3.4746    1.0482 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9061   -3.7194    0.5143 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  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
  9 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 15 17  1  0
  7  2  1  0
 17  9  1  0
 15  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
 10 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 14 38  1  0
 16 39  1  0
 16 40  1  0
 16 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(4a,10a)-1(5),6-Guaiadiene	Generator
(4Α,10α)-1(5),6-guaiadiene	Generator
(1R-cis)-1,2,3,4,5,6-Hexahydro-1,4-dimethyl-7-(1-methylethyl)azulene	HMDB
7,10-Epoxy-2-guaianone	HMDB
b-Kessyl ketone	HMDB, Generator
Β-kessyl ketone	Generator

Chemical Formula

C₁₅H₂₄O₂

Average Molecular Weight

236.3499

Monoisotopic Molecular Weight

236.177630012

IUPAC Name

1,5-dimethyl-8-(propan-2-yl)-11-oxatricyclo[6.2.1.0²,⁶]undecan-3-one

Traditional Name

8-isopropyl-1,5-dimethyl-11-oxatricyclo[6.2.1.0²,⁶]undecan-3-one

CAS Registry Number

3466-16-8

SMILES

CC(C)C12CCC(C)(O1)C1C(C2)C(C)CC1=O

InChI Identifier

InChI=1S/C15H24O2/c1-9(2)15-6-5-14(4,17-15)13-11(8-15)10(3)7-12(13)16/h9-11,13H,5-8H2,1-4H3

InChI Key

CSLBUZGPLRECOR-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Sesquiterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0036446)
Cell membrane (HMDB: HMDB0036446)

Cellular substructure

Extracellular (HMDB: HMDB0036446)
Membrane (HMDB: HMDB0036446)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036446)

Source

Endogenous

Endogenous (HMDB: HMDB0036446)

Plant

Plant (HMDB: HMDB0036446)

Animal

Animal (HMDB: HMDB0036446)

Exogenous

Food

Food (HMDB: HMDB0036446)

Tea

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Fat and oil

Fats and oils (FooDB: FOOD00864)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036446)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036446)

Cellular process

Cell signaling (HMDB: HMDB0036446)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036446)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036446)

Nutrient

Nutrient (HMDB: HMDB0036446)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036446)

Emulsifier (HMDB: HMDB0036446)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	109 - 110 °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	0.049 g/L	ALOGPS
logP	2.72	ALOGPS
logP	3.02	ChemAxon
logS	-3.7	ALOGPS
pKa (Strongest Acidic)	19.66	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.27 m³·mol⁻¹	ChemAxon
Polarizability	27.5 Å³	ChemAxon
Number of Rings	3	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]+	156.346	31661259
DarkChem	[M-H]-	154.016	31661259
DeepCCS	[M-2H]-	193.556	30932474
DeepCCS	[M+Na]+	169.122	30932474
AllCCS	[M+H]+	155.3	32859911
AllCCS	[M+H-H2O]+	151.6	32859911
AllCCS	[M+NH4]+	158.6	32859911
AllCCS	[M+Na]+	159.6	32859911
AllCCS	[M-H]-	164.1	32859911
AllCCS	[M+Na-2H]-	164.4	32859911
AllCCS	[M+HCOO]-	164.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-Kessyl ketone	CC(C)C12CCC(C)(O1)C1C(C2)C(C)CC1=O	2258.7	Standard polar	33892256
beta-Kessyl ketone	CC(C)C12CCC(C)(O1)C1C(C2)C(C)CC1=O	1665.4	Standard non polar	33892256
beta-Kessyl ketone	CC(C)C12CCC(C)(O1)C1C(C2)C(C)CC1=O	1707.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
beta-Kessyl ketone,1TMS,isomer #1	CC1CC(O[Si](C)(C)C)=C2C1CC1(C(C)C)CCC2(C)O1	1833.4	Semi standard non polar	33892256
beta-Kessyl ketone,1TMS,isomer #1	CC1CC(O[Si](C)(C)C)=C2C1CC1(C(C)C)CCC2(C)O1	1788.6	Standard non polar	33892256
beta-Kessyl ketone,1TMS,isomer #2	CC1C=C(O[Si](C)(C)C)C2C1CC1(C(C)C)CCC2(C)O1	1802.4	Semi standard non polar	33892256
beta-Kessyl ketone,1TMS,isomer #2	CC1C=C(O[Si](C)(C)C)C2C1CC1(C(C)C)CCC2(C)O1	1752.0	Standard non polar	33892256
beta-Kessyl ketone,1TBDMS,isomer #1	CC1CC(O[Si](C)(C)C(C)(C)C)=C2C1CC1(C(C)C)CCC2(C)O1	2074.9	Semi standard non polar	33892256
beta-Kessyl ketone,1TBDMS,isomer #1	CC1CC(O[Si](C)(C)C(C)(C)C)=C2C1CC1(C(C)C)CCC2(C)O1	2014.8	Standard non polar	33892256
beta-Kessyl ketone,1TBDMS,isomer #2	CC1C=C(O[Si](C)(C)C(C)(C)C)C2C1CC1(C(C)C)CCC2(C)O1	2035.0	Semi standard non polar	33892256
beta-Kessyl ketone,1TBDMS,isomer #2	CC1C=C(O[Si](C)(C)C(C)(C)C)C2C1CC1(C(C)C)CCC2(C)O1	1906.2	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Kessyl ketone GC-MS (Non-derivatized) - 70eV, Positive	splash10-006x-8930000000-176f4acad793d482bea6	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Kessyl ketone 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 - beta-Kessyl ketone 10V, Positive-QTOF	splash10-000i-0090000000-ec5d9353ef77ab3e5a23	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Kessyl ketone 20V, Positive-QTOF	splash10-000i-1390000000-ec86dbdf656f6f2a4e2a	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Kessyl ketone 40V, Positive-QTOF	splash10-0udi-9310000000-3b25191a20537d997525	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Kessyl ketone 10V, Negative-QTOF	splash10-000i-0090000000-ff88305a80d6066d42a3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Kessyl ketone 20V, Negative-QTOF	splash10-000i-0190000000-6ce8e3a3027fa7747d29	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Kessyl ketone 40V, Negative-QTOF	splash10-0597-9710000000-3786389a6796b88ce1fe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Kessyl ketone 10V, Positive-QTOF	splash10-00kr-0090000000-9a9d418a32a074f83aeb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Kessyl ketone 20V, Positive-QTOF	splash10-000i-3490000000-d5964cd7e03786a77ffe	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Kessyl ketone 40V, Positive-QTOF	splash10-0a5i-9670000000-20d64c56b7421f12c6b7	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Kessyl ketone 10V, Negative-QTOF	splash10-000i-0090000000-c0031dc201eac6b6350a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Kessyl ketone 20V, Negative-QTOF	splash10-000i-0090000000-c0031dc201eac6b6350a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Kessyl ketone 40V, Negative-QTOF	splash10-000i-0390000000-4e17388c8247e6c86540	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

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

FDB015337

KNApSAcK ID

C00020375

Chemspider ID

10471161

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

15560254

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 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for beta-Kessyl ketone (HMDB0036446)

MOL for HMDB0036446 (beta-Kessyl ketone)

3D MOL for HMDB0036446 (beta-Kessyl ketone)

3D SDF for HMDB0036446 (beta-Kessyl ketone)

3D-SDF for HMDB0036446 (beta-Kessyl ketone)

PDB for HMDB0036446 (beta-Kessyl ketone)

3D PDB for HMDB0036446 (beta-Kessyl ketone)

SMILES for HMDB0036446 (beta-Kessyl ketone)

INCHI for HMDB0036446 (beta-Kessyl ketone)

Structure for HMDB0036446 (beta-Kessyl ketone)

3D Structure for HMDB0036446 (beta-Kessyl ketone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra