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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:58:00 UTC

Update Date

2022-03-07 02:55:03 UTC

HMDB ID

HMDB0036790

Secondary Accession Numbers

HMDB36790

Metabolite Identification

Common Name

Kobusone

Description

Kobusone belongs to the class of organic compounds known as ketones. These are organic compounds in which a carbonyl group is bonded to two carbon atoms R2C=O (neither R may be a hydrogen atom). Ketones that have one or more alpha-hydrogen atoms undergo keto-enol tautomerization, the tautomer being an enol. Kobusone has been detected, but not quantified in, root vegetables. This could make kobusone a potential biomarker for the consumption of these foods. Based on a literature review a significant number of articles have been published on Kobusone.

Structure

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

HMDB0036790
     RDKit          3D
Kobusone
 38 40  0  0  0  0  0  0  0  0999 V2000
   -2.6075   -0.2867    1.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1694   -0.1005    0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0216   -0.9761   -0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2079    1.3714   -0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7426    1.2544   -0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640    2.0551    0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3019    2.3874    1.4019 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5270    2.4365   -0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5104    1.2844    0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2267    0.1723   -0.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1730   -0.7631   -1.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1352   -1.0908   -0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7361   -1.3866    1.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9995   -1.9225   -0.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155   -1.1470   -1.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6970   -0.1624   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5361   -0.9192    1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9006    0.6847    2.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589   -0.7404    2.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0722   -0.7377   -0.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7311   -0.9114   -1.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8674   -2.0265   -0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4054    2.0664    0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955    1.5749   -1.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299    1.4323   -1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6241    2.7781   -1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8597    3.2687    0.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5428    1.6232    0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2714    0.8948    1.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5616    0.4548   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0038   -1.4033    1.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5803   -0.6622    1.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2627   -2.3793    1.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2492   -2.6257   -1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6780   -2.5795    0.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0574   -0.6976   -2.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0322   -1.9089   -1.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1551   -0.3120    0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16  2  1  0
 16  5  1  0
 12 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
M  END


  Mrv0541 05061309202D          

 16 18  0  0  0  0            999 V2000
    5.8458   -1.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8972   -2.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7241   -1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1544    0.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3822    0.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916   -1.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7666   -1.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1666   -0.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3526   -0.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2179   -1.1149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9326    0.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9773   -0.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0319   -1.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1291   -1.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4562    1.0467    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.3509   -0.8629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  1  0  0  0  0
  7  6  1  0  0  0  0
  9  8  1  0  0  0  0
 10  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  4  1  0  0  0  0
 11  9  1  0  0  0  0
 12  5  1  0  0  0  0
 13  1  1  0  0  0  0
 13  2  1  0  0  0  0
 13  8  1  0  0  0  0
 13 10  1  0  0  0  0
 14  3  1  0  0  0  0
 14  7  1  0  0  0  0
 14 12  1  0  0  0  0
 15 11  2  0  0  0  0
 16 12  1  0  0  0  0
 16 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036790

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC3C(CC3(C)C)C(=O)CCC1O2

> <INCHI_IDENTIFIER>
InChI=1S/C14H22O2/c1-13(2)8-9-10(13)6-7-14(3)12(16-14)5-4-11(9)15/h9-10,12H,4-8H2,1-3H3

> <INCHI_KEY>
UETZJEZFLKASPR-UHFFFAOYSA-N

> <FORMULA>
C14H22O2

> <MOLECULAR_WEIGHT>
222.3233

> <EXACT_MASS>
222.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.44551485681503

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,12,12-trimethyl-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-9-one

> <ALOGPS_LOGP>
2.50

> <JCHEM_LOGP>
2.755904054666667

> <ALOGPS_LOGS>
-3.32

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.49805561593643

> <JCHEM_PKA_STRONGEST_BASIC>
-4.224184024856662

> <JCHEM_POLAR_SURFACE_AREA>
29.6

> <JCHEM_REFRACTIVITY>
62.554100000000005

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.05e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,12,12-trimethyl-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-9-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036790
     RDKit          3D
Kobusone
 38 40  0  0  0  0  0  0  0  0999 V2000
   -2.6075   -0.2867    1.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1694   -0.1005    0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0216   -0.9761   -0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2079    1.3714   -0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7426    1.2544   -0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640    2.0551    0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3019    2.3874    1.4019 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5270    2.4365   -0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5104    1.2844    0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2267    0.1723   -0.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1730   -0.7631   -1.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1352   -1.0908   -0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7361   -1.3866    1.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9995   -1.9225   -0.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155   -1.1470   -1.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6970   -0.1624   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5361   -0.9192    1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9006    0.6847    2.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589   -0.7404    2.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0722   -0.7377   -0.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7311   -0.9114   -1.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8674   -2.0265   -0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4054    2.0664    0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955    1.5749   -1.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299    1.4323   -1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6241    2.7781   -1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8597    3.2687    0.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5428    1.6232    0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2714    0.8948    1.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5616    0.4548   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0038   -1.4033    1.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5803   -0.6622    1.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2627   -2.3793    1.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2492   -2.6257   -1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6780   -2.5795    0.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0574   -0.6976   -2.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0322   -1.9089   -1.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1551   -0.3120    0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16  2  1  0
 16  5  1  0
 12 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      10.912  -2.584   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.141  -3.852   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.218  -3.464   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.888   1.275   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.447   0.733   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.704  -3.083   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       5.164  -3.100   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.644  -0.813   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.125  -0.562   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.873  -2.081   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.341   0.764   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.691  -0.609   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       9.393  -2.333   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.974  -2.122   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       8.318   1.954   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.522  -1.611   0.000  0.00  0.00           O+0
CONECT    1   13                                                            
CONECT    2   13                                                            
CONECT    3   14                                                            
CONECT    4    5   11                                                       
CONECT    5    4   12                                                       
CONECT    6    7   10                                                       
CONECT    7    6   14                                                       
CONECT    8    9   13                                                       
CONECT    9    8   10   11                                                  
CONECT   10    6    9   13                                                  
CONECT   11    4    9   15                                                  
CONECT   12    5   14   16                                                  
CONECT   13    1    2    8   10                                             
CONECT   14    3    7   12   16                                             
CONECT   15   11                                                            
CONECT   16   12   14                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0036790
HETATM    1  C1  UNL     1      -2.607  -0.287   1.590  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.169  -0.100   0.165  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.022  -0.976  -0.748  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.208   1.371  -0.198  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.743   1.254  -0.576  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.164   2.055   0.310  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.302   2.387   1.402  1.00  0.00           O  
HETATM    8  C7  UNL     1       1.527   2.436  -0.070  1.00  0.00           C  
HETATM    9  C8  UNL     1       2.510   1.284   0.140  1.00  0.00           C  
HETATM   10  C9  UNL     1       2.227   0.172  -0.816  1.00  0.00           C  
HETATM   11  O2  UNL     1       3.173  -0.763  -1.146  1.00  0.00           O  
HETATM   12  C10 UNL     1       2.135  -1.091  -0.213  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.736  -1.387   1.149  1.00  0.00           C  
HETATM   14  C12 UNL     1       0.999  -1.922  -0.678  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.215  -1.147  -1.097  1.00  0.00           C  
HETATM   16  C14 UNL     1      -0.697  -0.162  -0.094  1.00  0.00           C  
HETATM   17  H1  UNL     1      -3.536  -0.919   1.675  1.00  0.00           H  
HETATM   18  H2  UNL     1      -2.901   0.685   2.079  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.859  -0.740   2.238  1.00  0.00           H  
HETATM   20  H4  UNL     1      -4.072  -0.738  -0.535  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.731  -0.911  -1.796  1.00  0.00           H  
HETATM   22  H6  UNL     1      -2.867  -2.026  -0.367  1.00  0.00           H  
HETATM   23  H7  UNL     1      -2.405   2.066   0.620  1.00  0.00           H  
HETATM   24  H8  UNL     1      -2.896   1.575  -1.047  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.630   1.432  -1.647  1.00  0.00           H  
HETATM   26  H10 UNL     1       1.624   2.778  -1.108  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.860   3.269   0.598  1.00  0.00           H  
HETATM   28  H12 UNL     1       3.543   1.623   0.170  1.00  0.00           H  
HETATM   29  H13 UNL     1       2.271   0.895   1.173  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.562   0.455  -1.661  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.004  -1.403   1.955  1.00  0.00           H  
HETATM   32  H16 UNL     1       3.580  -0.662   1.328  1.00  0.00           H  
HETATM   33  H17 UNL     1       3.263  -2.379   1.028  1.00  0.00           H  
HETATM   34  H18 UNL     1       1.249  -2.626  -1.496  1.00  0.00           H  
HETATM   35  H19 UNL     1       0.678  -2.580   0.182  1.00  0.00           H  
HETATM   36  H20 UNL     1      -0.057  -0.698  -2.121  1.00  0.00           H  
HETATM   37  H21 UNL     1      -1.032  -1.909  -1.267  1.00  0.00           H  
HETATM   38  H22 UNL     1      -0.155  -0.312   0.880  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4   16
CONECT    3   20   21   22
CONECT    4    5   23   24
CONECT    5    6   16   25
CONECT    6    7    7    8
CONECT    8    9   26   27
CONECT    9   10   28   29
CONECT   10   11   12   30
CONECT   11   12
CONECT   12   13   14
CONECT   13   31   32   33
CONECT   14   15   34   35
CONECT   15   16   36   37
CONECT   16   38
END

HMDB0036790
     RDKit          3D
Kobusone
 38 40  0  0  0  0  0  0  0  0999 V2000
   -2.6075   -0.2867    1.5898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1694   -0.1005    0.1647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0216   -0.9761   -0.7482 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2079    1.3714   -0.1984 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7426    1.2544   -0.5762 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1640    2.0551    0.3096 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3019    2.3874    1.4019 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.5270    2.4365   -0.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5104    1.2844    0.1398 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2267    0.1723   -0.8157 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1730   -0.7631   -1.1462 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1352   -1.0908   -0.2131 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7361   -1.3866    1.1488 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9995   -1.9225   -0.6780 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2155   -1.1470   -1.0965 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6970   -0.1624   -0.0942 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5361   -0.9192    1.6747 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9006    0.6847    2.0790 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8589   -0.7404    2.2380 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0722   -0.7377   -0.5345 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7311   -0.9114   -1.7960 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8674   -2.0265   -0.3673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4054    2.0664    0.6200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8955    1.5749   -1.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6299    1.4323   -1.6473 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6241    2.7781   -1.1081 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8597    3.2687    0.5977 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5428    1.6232    0.1700 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2714    0.8948    1.1727 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5616    0.4548   -1.6607 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0038   -1.4033    1.9550 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5803   -0.6622    1.3282 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2627   -2.3793    1.0283 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2492   -2.6257   -1.4959 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6780   -2.5795    0.1819 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0574   -0.6976   -2.1206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0322   -1.9089   -1.2674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1551   -0.3120    0.8802 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 14 15  1  0
 15 16  1  0
 16  2  1  0
 16  5  1  0
 12 10  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  4 24  1  0
  5 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 13 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 14 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-Kobusone	HMDB
6,7-Epoxy-15-nor-3-caryophyllanone	HMDB
Caryophyllene keto epoxide	HMDB

Chemical Formula

C₁₄H₂₂O₂

Average Molecular Weight

222.3233

Monoisotopic Molecular Weight

222.161979948

IUPAC Name

4,12,12-trimethyl-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-9-one

Traditional Name

4,12,12-trimethyl-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-9-one

CAS Registry Number

24173-71-5

SMILES

CC12CCC3C(CC3(C)C)C(=O)CCC1O2

InChI Identifier

InChI=1S/C14H22O2/c1-13(2)8-9-10(13)6-7-14(3)12(16-14)5-4-11(9)15/h9-10,12H,4-8H2,1-3H3

InChI Key

UETZJEZFLKASPR-UHFFFAOYSA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Ketones

Alternative Parents

Substituents

Ketone
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036790)

Source

Endogenous

Endogenous (HMDB: HMDB0036790)

Plant

Plant (HMDB: HMDB0036790)

Exogenous

Food

Food (HMDB: HMDB0036790)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Exogenous (HMDB: HMDB0036790)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036790)

Role

Biological role

Energy source (HMDB: HMDB0036790)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036790)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	60 - 61 °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	0.1 g/L	ALOGPS
logP	2.5	ALOGPS
logP	2.76	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	18.5	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	62.55 m³·mol⁻¹	ChemAxon
Polarizability	25.45 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]+	153.32	31661259
DarkChem	[M-H]-	148.757	31661259
DeepCCS	[M-2H]-	186.878	30932474
DeepCCS	[M+Na]+	162.369	30932474
AllCCS	[M+H]+	152.4	32859911
AllCCS	[M+H-H2O]+	148.6	32859911
AllCCS	[M+NH4]+	155.9	32859911
AllCCS	[M+Na]+	156.9	32859911
AllCCS	[M-H]-	159.4	32859911
AllCCS	[M+Na-2H]-	159.6	32859911
AllCCS	[M+HCOO]-	159.9	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.67 minutes	32390414
Predicted by Siyang on May 30, 2022	14.644 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.07 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2370.6 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	422.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	184.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	197.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	228.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	694.5 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	709.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	69.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1161.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	372.0 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1318.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	444.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	377.0 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	377.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	458.7 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	24.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Kobusone	CC12CCC3C(CC3(C)C)C(=O)CCC1O2	2382.5	Standard polar	33892256
Kobusone	CC12CCC3C(CC3(C)C)C(=O)CCC1O2	1618.8	Standard non polar	33892256
Kobusone	CC12CCC3C(CC3(C)C)C(=O)CCC1O2	1725.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Kobusone,1TMS,isomer #1	CC1(C)CC2=C(O[Si](C)(C)C)CCC3OC3(C)CCC21	1844.0	Semi standard non polar	33892256
Kobusone,1TMS,isomer #1	CC1(C)CC2=C(O[Si](C)(C)C)CCC3OC3(C)CCC21	1798.2	Standard non polar	33892256
Kobusone,1TMS,isomer #2	CC1(C)CC2C(O[Si](C)(C)C)=CCC3OC3(C)CCC21	1776.8	Semi standard non polar	33892256
Kobusone,1TMS,isomer #2	CC1(C)CC2C(O[Si](C)(C)C)=CCC3OC3(C)CCC21	1735.9	Standard non polar	33892256
Kobusone,1TBDMS,isomer #1	CC1(C)CC2=C(O[Si](C)(C)C(C)(C)C)CCC3OC3(C)CCC21	2081.5	Semi standard non polar	33892256
Kobusone,1TBDMS,isomer #1	CC1(C)CC2=C(O[Si](C)(C)C(C)(C)C)CCC3OC3(C)CCC21	2013.9	Standard non polar	33892256
Kobusone,1TBDMS,isomer #2	CC1(C)CC2C(O[Si](C)(C)C(C)(C)C)=CCC3OC3(C)CCC21	2000.5	Semi standard non polar	33892256
Kobusone,1TBDMS,isomer #2	CC1(C)CC2C(O[Si](C)(C)C(C)(C)C)=CCC3OC3(C)CCC21	1890.4	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Kobusone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aou-9740000000-2af7e6e26aaccb11d53e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Kobusone 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 - Kobusone 10V, Positive-QTOF	splash10-00di-0090000000-e7eb46754d84a1f001ea	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kobusone 20V, Positive-QTOF	splash10-0ab9-3490000000-46f0fc3ab8643fae1fa5	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kobusone 40V, Positive-QTOF	splash10-0a4j-9300000000-b0698cdabc77a1cff6c8	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kobusone 10V, Negative-QTOF	splash10-00di-0090000000-709b2376e5d479d781b8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kobusone 20V, Negative-QTOF	splash10-00di-1190000000-a9dbc119142ad669504a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kobusone 40V, Negative-QTOF	splash10-052f-9400000000-d1a72bb410e20ed08d16	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kobusone 10V, Positive-QTOF	splash10-00di-0090000000-26b9efbf9f84855d0305	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kobusone 20V, Positive-QTOF	splash10-0a4i-9460000000-6860eaf0f81013354564	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kobusone 40V, Positive-QTOF	splash10-052f-9210000000-a89beaf32ac32c6b19df	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kobusone 10V, Negative-QTOF	splash10-00di-0090000000-277654a816c7fdb457aa	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kobusone 20V, Negative-QTOF	splash10-00di-0090000000-2ea64cb0d1e6b009cf73	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Kobusone 40V, Negative-QTOF	splash10-0gi0-0090000000-dd17b4d6ab8567d67b59	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
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

FDB015734

KNApSAcK ID

C00012492

Chemspider ID

2683359

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

3440569

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1857211

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Kobusone (HMDB0036790)

MOL for HMDB0036790 (Kobusone)

3D MOL for HMDB0036790 (Kobusone)

3D SDF for HMDB0036790 (Kobusone)

3D-SDF for HMDB0036790 (Kobusone)

PDB for HMDB0036790 (Kobusone)

3D PDB for HMDB0036790 (Kobusone)

SMILES for HMDB0036790 (Kobusone)

INCHI for HMDB0036790 (Kobusone)

Structure for HMDB0036790 (Kobusone)

3D Structure for HMDB0036790 (Kobusone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra