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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:28:26 UTC

Update Date

2022-03-07 02:55:40 UTC

HMDB ID

HMDB0038193

Secondary Accession Numbers

HMDB38193

Metabolite Identification

Common Name

Isoshyobunone

Description

Isoshyobunone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on Isoshyobunone.

Structure

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

HMDB0038193
     RDKit          3D
Isoshyobunone
 40 40  0  0  0  0  0  0  0  0999 V2000
   -3.1059    1.6655   -1.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2172    0.6934   -1.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2508    0.6742   -0.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6904    1.4572    0.6212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0851    1.3132   -1.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9137    1.5149    0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4251    0.1620    0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8839    0.1246    0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5342    1.2916    1.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6026   -1.1131    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6211   -0.9078    0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0645   -2.0341   -0.0927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8179   -0.6902   -0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6744   -1.6677   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2066   -3.0412    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1005   -1.5377   -0.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1707    2.4805   -1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8479    1.7234   -2.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2023   -0.0702   -2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4722    2.5535    0.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7924    1.4050    0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2701    1.0849    1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5912    0.5414   -1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881    2.2542   -1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3936    2.0798    0.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7672    2.1685   -0.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460    0.1959    1.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9997    0.3186   -0.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9586    1.5932    2.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5418    0.9911    1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7222    2.1262    0.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4486   -0.9189    1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9840   -1.8884    1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0832   -1.5620   -0.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0764   -3.7152    0.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6912   -3.4815   -0.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5652   -3.0119    1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5831   -0.5954   -0.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3361   -1.8622   -1.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7069   -2.3152    0.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
 13  3  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END


  Mrv0541 05061310172D          

 16 16  0  0  0  0            999 V2000
    0.4663    2.6447    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    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
    1.4289    0.8250    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
   -0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    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
    0.0000    0.0000    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
   -0.7145   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  1  2  0  0  0  0
  9  8  1  0  0  0  0
 10  2  1  0  0  0  0
 10  3  1  0  0  0  0
 11  4  1  0  0  0  0
 11  5  1  0  0  0  0
 12  8  1  0  0  0  0
 12 10  1  0  0  0  0
 13 11  2  0  0  0  0
 14 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15  6  1  0  0  0  0
 15  7  1  0  0  0  0
 15  9  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038193

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1CCC(C)(C=C)C(=C(C)C)C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-7-15(6)9-8-12(10(2)3)14(16)13(15)11(4)5/h7,10,12H,1,8-9H2,2-6H3

> <INCHI_KEY>
YMIHAYABXZORPU-UHFFFAOYSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.3505

> <EXACT_MASS>
220.18271539

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.885886122119008

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-ethenyl-3-methyl-6-(propan-2-yl)-2-(propan-2-ylidene)cyclohexan-1-one

> <ALOGPS_LOGP>
4.59

> <JCHEM_LOGP>
4.5717191150000005

> <ALOGPS_LOGS>
-4.24

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.911748837789196

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
69.9737

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.26e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-ethenyl-6-isopropyl-3-methyl-2-(propan-2-ylidene)cyclohexan-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0038193
     RDKit          3D
Isoshyobunone
 40 40  0  0  0  0  0  0  0  0999 V2000
   -3.1059    1.6655   -1.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2172    0.6934   -1.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2508    0.6742   -0.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6904    1.4572    0.6212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0851    1.3132   -1.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9137    1.5149    0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4251    0.1620    0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8839    0.1246    0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5342    1.2916    1.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6026   -1.1131    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6211   -0.9078    0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0645   -2.0341   -0.0927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8179   -0.6902   -0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6744   -1.6677   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2066   -3.0412    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1005   -1.5377   -0.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1707    2.4805   -1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8479    1.7234   -2.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2023   -0.0702   -2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4722    2.5535    0.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7924    1.4050    0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2701    1.0849    1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5912    0.5414   -1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881    2.2542   -1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3936    2.0798    0.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7672    2.1685   -0.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460    0.1959    1.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9997    0.3186   -0.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9586    1.5932    2.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5418    0.9911    1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7222    2.1262    0.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4486   -0.9189    1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9840   -1.8884    1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0832   -1.5620   -0.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0764   -3.7152    0.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6912   -3.4815   -0.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5652   -3.0119    1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5831   -0.5954   -0.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3361   -1.8622   -1.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7069   -2.3152    0.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
 13  3  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  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       0.870   4.937   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.334   3.850   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.667   1.540   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      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -1.334  -0.770   0.000  0.00  0.00           O+0
CONECT    1    7                                                            
CONECT    2   10                                                            
CONECT    3   10                                                            
CONECT    4   11                                                            
CONECT    5   11                                                            
CONECT    6   15                                                            
CONECT    7    1   15                                                       
CONECT    8    9   12                                                       
CONECT    9    8   15                                                       
CONECT   10    2    3   12                                                  
CONECT   11    4    5   13                                                  
CONECT   12    8   10   14                                                  
CONECT   13   11   14   15                                                  
CONECT   14   12   13   16                                                  
CONECT   15    6    7    9   13                                             
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0038193
HETATM    1  C1  UNL     1      -3.106   1.665  -1.784  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.217   0.693  -1.702  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.251   0.674  -0.595  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.690   1.457   0.621  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.085   1.313  -1.070  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.914   1.515   0.174  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.425   0.162   0.695  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.884   0.125   0.385  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.534   1.292   1.103  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.603  -1.113   0.787  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.621  -0.908   0.144  1.00  0.00           C  
HETATM   12  O1  UNL     1       1.065  -2.034  -0.093  1.00  0.00           O  
HETATM   13  C12 UNL     1      -0.818  -0.690  -0.173  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.674  -1.668  -0.087  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.207  -3.041   0.345  1.00  0.00           C  
HETATM   16  C15 UNL     1      -3.101  -1.538  -0.390  1.00  0.00           C  
HETATM   17  H1  UNL     1      -3.171   2.480  -1.061  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.848   1.723  -2.591  1.00  0.00           H  
HETATM   19  H3  UNL     1      -2.202  -0.070  -2.452  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.472   2.553   0.439  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.792   1.405   0.716  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.270   1.085   1.558  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.591   0.541  -1.695  1.00  0.00           H  
HETATM   24  H8  UNL     1      -0.088   2.254  -1.582  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.394   2.080   0.942  1.00  0.00           H  
HETATM   26  H10 UNL     1       1.767   2.168  -0.154  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.246   0.196   1.800  1.00  0.00           H  
HETATM   28  H12 UNL     1       3.000   0.319  -0.703  1.00  0.00           H  
HETATM   29  H13 UNL     1       2.959   1.593   2.003  1.00  0.00           H  
HETATM   30  H14 UNL     1       4.542   0.991   1.490  1.00  0.00           H  
HETATM   31  H15 UNL     1       3.722   2.126   0.414  1.00  0.00           H  
HETATM   32  H16 UNL     1       4.449  -0.919   1.508  1.00  0.00           H  
HETATM   33  H17 UNL     1       2.984  -1.888   1.252  1.00  0.00           H  
HETATM   34  H18 UNL     1       4.083  -1.562  -0.107  1.00  0.00           H  
HETATM   35  H19 UNL     1      -2.076  -3.715   0.535  1.00  0.00           H  
HETATM   36  H20 UNL     1      -0.691  -3.482  -0.531  1.00  0.00           H  
HETATM   37  H21 UNL     1      -0.565  -3.012   1.223  1.00  0.00           H  
HETATM   38  H22 UNL     1      -3.583  -0.595  -0.115  1.00  0.00           H  
HETATM   39  H23 UNL     1      -3.336  -1.862  -1.451  1.00  0.00           H  
HETATM   40  H24 UNL     1      -3.707  -2.315   0.202  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3   19
CONECT    3    4    5   13
CONECT    4   20   21   22
CONECT    5    6   23   24
CONECT    6    7   25   26
CONECT    7    8   11   27
CONECT    8    9   10   28
CONECT    9   29   30   31
CONECT   10   32   33   34
CONECT   11   12   12   13
CONECT   13   14   14
CONECT   14   15   16
CONECT   15   35   36   37
CONECT   16   38   39   40
END

HMDB0038193
     RDKit          3D
Isoshyobunone
 40 40  0  0  0  0  0  0  0  0999 V2000
   -3.1059    1.6655   -1.7841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2172    0.6934   -1.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2508    0.6742   -0.5954 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6904    1.4572    0.6212 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0851    1.3132   -1.0700 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9137    1.5149    0.1738 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4251    0.1620    0.6952 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8839    0.1246    0.3853 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5342    1.2916    1.1027 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6026   -1.1131    0.7870 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6211   -0.9078    0.1436 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0645   -2.0341   -0.0927 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8179   -0.6902   -0.1729 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6744   -1.6677   -0.0870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2066   -3.0412    0.3451 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1005   -1.5377   -0.3896 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1707    2.4805   -1.0605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8479    1.7234   -2.5914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2023   -0.0702   -2.4518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4722    2.5535    0.4392 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7924    1.4050    0.7156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2701    1.0849    1.5583 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5912    0.5414   -1.6946 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0881    2.2542   -1.5816 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3936    2.0798    0.9415 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7672    2.1685   -0.1542 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2460    0.1959    1.8000 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9997    0.3186   -0.7026 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9586    1.5932    2.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5418    0.9911    1.4901 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7222    2.1262    0.4138 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4486   -0.9189    1.5077 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9840   -1.8884    1.2517 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0832   -1.5620   -0.1070 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0764   -3.7152    0.5346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6912   -3.4815   -0.5311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5652   -3.0119    1.2235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5831   -0.5954   -0.1151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3361   -1.8622   -1.4510 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7069   -2.3152    0.2022 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  3  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  7 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
 13  3  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  4 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 10 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
iso-Shyobunone	HMDB

Chemical Formula

C₁₅H₂₄O

Average Molecular Weight

220.3505

Monoisotopic Molecular Weight

220.18271539

IUPAC Name

3-ethenyl-3-methyl-6-(propan-2-yl)-2-(propan-2-ylidene)cyclohexan-1-one

Traditional Name

3-ethenyl-6-isopropyl-3-methyl-2-(propan-2-ylidene)cyclohexan-1-one

CAS Registry Number

21698-46-4

SMILES

CC(C)C1CCC(C)(C=C)C(=C(C)C)C1=O

InChI Identifier

InChI=1S/C15H24O/c1-7-15(6)9-8-12(10(2)3)14(16)13(15)11(4)5/h7,10,12H,1,8-9H2,2-6H3

InChI Key

YMIHAYABXZORPU-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
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Membrane (HMDB: HMDB0038193)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038193)

Source

Endogenous

Endogenous (HMDB: HMDB0038193)

Plant

Plant (HMDB: HMDB0038193)

Animal

Animal (HMDB: HMDB0038193)

Exogenous

Food

Food (HMDB: HMDB0038193)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0038193)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0038193)

Cellular process

Cell signaling (HMDB: HMDB0038193)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0038193)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0038193)

Nutrient

Nutrient (HMDB: HMDB0038193)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038193)

Emulsifier (HMDB: HMDB0038193)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	289.00 to 290.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.95 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.084 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.013 g/L	ALOGPS
logP	4.59	ALOGPS
logP	4.57	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-4.9	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	2	ChemAxon
Refractivity	69.97 m³·mol⁻¹	ChemAxon
Polarizability	26.89 Å³	ChemAxon
Number of Rings	1	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]+	152.429	31661259
DarkChem	[M-H]-	149.305	31661259
DeepCCS	[M+H]+	156.966	30932474
DeepCCS	[M-H]-	154.608	30932474
DeepCCS	[M-2H]-	188.52	30932474
DeepCCS	[M+Na]+	163.66	30932474
AllCCS	[M+H]+	150.6	32859911
AllCCS	[M+H-H2O]+	146.8	32859911
AllCCS	[M+NH4]+	154.1	32859911
AllCCS	[M+Na]+	155.1	32859911
AllCCS	[M-H]-	159.5	32859911
AllCCS	[M+Na-2H]-	160.3	32859911
AllCCS	[M+HCOO]-	161.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isoshyobunone	CC(C)C1CCC(C)(C=C)C(=C(C)C)C1=O	1916.3	Standard polar	33892256
Isoshyobunone	CC(C)C1CCC(C)(C=C)C(=C(C)C)C1=O	1450.5	Standard non polar	33892256
Isoshyobunone	CC(C)C1CCC(C)(C=C)C(=C(C)C)C1=O	1540.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Isoshyobunone,1TMS,isomer #1	C=CC1(C)CCC(C(C)C)=C(O[Si](C)(C)C)C1=C(C)C	1603.4	Semi standard non polar	33892256
Isoshyobunone,1TMS,isomer #1	C=CC1(C)CCC(C(C)C)=C(O[Si](C)(C)C)C1=C(C)C	1628.3	Standard non polar	33892256
Isoshyobunone,1TBDMS,isomer #1	C=CC1(C)CCC(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C1=C(C)C	1812.2	Semi standard non polar	33892256
Isoshyobunone,1TBDMS,isomer #1	C=CC1(C)CCC(C(C)C)=C(O[Si](C)(C)C(C)(C)C)C1=C(C)C	1865.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Isoshyobunone GC-MS (Non-derivatized) - 70eV, Positive	splash10-056u-9840000000-0b0c62f9e114210bee39	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoshyobunone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isoshyobunone 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 - Isoshyobunone 10V, Positive-QTOF	splash10-00di-2590000000-dcb5bd2d3adfb26564f1	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoshyobunone 20V, Positive-QTOF	splash10-057i-6920000000-879cd1de6c285d5c2601	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoshyobunone 40V, Positive-QTOF	splash10-0pvi-9100000000-00bd0aff8cb3924cfc31	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoshyobunone 10V, Negative-QTOF	splash10-014i-0090000000-fb53c60f3c02ccb82d4d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoshyobunone 20V, Negative-QTOF	splash10-016r-0790000000-b1821558c376daddb9a2	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoshyobunone 40V, Negative-QTOF	splash10-117i-5920000000-e5fba62c185e5d730fe4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoshyobunone 10V, Negative-QTOF	splash10-014i-0090000000-4af4c4ee1c4acef7e18b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoshyobunone 20V, Negative-QTOF	splash10-014i-0690000000-8518ba79dc593baef7fa	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoshyobunone 40V, Negative-QTOF	splash10-0fwi-2940000000-7603b66247a3e77ee402	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoshyobunone 10V, Positive-QTOF	splash10-00di-0190000000-3a015085bf7fadece0ba	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoshyobunone 20V, Positive-QTOF	splash10-00kv-5920000000-22653fcd3a1395123f4c	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isoshyobunone 40V, Positive-QTOF	splash10-05n3-9800000000-550d22ce2dd3dbec325c	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

FDB017432

KNApSAcK ID

C00012007

Chemspider ID

35014531

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

12304470

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1590151

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 Isoshyobunone (HMDB0038193)

MOL for HMDB0038193 (Isoshyobunone)

3D MOL for HMDB0038193 (Isoshyobunone)

3D SDF for HMDB0038193 (Isoshyobunone)

3D-SDF for HMDB0038193 (Isoshyobunone)

PDB for HMDB0038193 (Isoshyobunone)

3D PDB for HMDB0038193 (Isoshyobunone)

SMILES for HMDB0038193 (Isoshyobunone)

INCHI for HMDB0038193 (Isoshyobunone)

Structure for HMDB0038193 (Isoshyobunone)

3D Structure for HMDB0038193 (Isoshyobunone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra