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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 20:56:49 UTC

Update Date

2021-09-23 20:56:49 UTC

HMDB ID

HMDB0302822

Secondary Accession Numbers

None

Metabolite Identification

Common Name

(+)-Dehydrovomifoliol

Description

(+)-dehydrovomifoliol, also known as (6s)-6-hydroxy-3-oxo-alpha-ionone, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Thus, (+)-dehydrovomifoliol is considered to be an isoprenoid lipid molecule (+)-dehydrovomifoliol is practically insoluble (in water) and a very weakly acidic compound (based on its pKa). (+)-dehydrovomifoliol can be found in rice, which makes (+)-dehydrovomifoliol a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302822
     RDKit          3D
(+)-Dehydrovomifoliol
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.5758    0.6055   -0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3151    0.5027    0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3244    0.7309    1.8638 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0955    0.1441   -0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9267    0.0281    0.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2679   -0.3421   -0.2144 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1204   -0.7856   -1.5004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0191   -1.4366    0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5472   -2.8192    0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0699   -1.2225    1.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5536    0.1305    1.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5462    0.3601    2.1946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044    1.2758    0.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958    0.8257   -0.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    1.9461   -1.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2580    0.3151   -1.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4862    0.0635   -1.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4132    0.1376    0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7733    1.6799   -0.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433   -0.0439   -1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8740    0.2098    1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1077   -1.7227   -1.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1096   -3.3042   -0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5560   -2.8033    0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7076   -3.4385    1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6034   -2.0334    1.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7342    1.9625    0.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2787    1.8825    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327    2.5453   -0.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1269    2.6012   -1.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3479    1.5669   -1.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9201    0.4842   -2.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2457    0.7521   -1.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3751   -0.7981   -1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 13 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
M  END


  Mrv1533007131513452D          

 18 18  0  0  1  0            999 V2000
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2182    4.0520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    0.6817    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2822    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4663    2.6447    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
    0.0000   -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
   -0.0640    3.2767    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
    0.7145    1.2375    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.8764    3.1335    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2788    2.7880    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4478    2.3998    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  2  0  0  0  0
  9  1  1  0  0  0  0
  9  7  2  0  0  0  0
 10  2  1  0  0  0  0
 10  5  1  0  0  0  0
 11  7  1  0  0  0  0
 11  8  1  0  0  0  0
 12  3  1  0  0  0  0
 12  4  1  0  0  0  0
 12  8  1  0  0  0  0
 13  6  1  1  0  0  0
 13  9  1  0  0  0  0
 13 12  1  0  0  0  0
 14 10  2  0  0  0  0
 15 11  2  0  0  0  0
 13 16  1  6  0  0  0
 17  5  1  0  0  0  0
 18  6  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302822

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(=C(\[H])[C@@]1(O)C(C)=CC(=O)CC1(C)C)C(C)=O

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,16H,8H2,1-4H3/b6-5+/t13-/m1/s1

> <INCHI_KEY>
JJRYPZMXNLLZFH-URWSZGRFSA-N

> <FORMULA>
C13H18O3

> <MOLECULAR_WEIGHT>
222.284

> <EXACT_MASS>
222.12559444

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
34

> <JCHEM_AVERAGE_POLARIZABILITY>
24.15398104375082

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4S)-4-hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one

> <ALOGPS_LOGP>
1.41

> <JCHEM_LOGP>
1.6523240710000004

> <ALOGPS_LOGS>
-2.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.034527167005127

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.372685613937566

> <JCHEM_PKA_STRONGEST_BASIC>
-3.5105853036630945

> <JCHEM_POLAR_SURFACE_AREA>
54.370000000000005

> <JCHEM_REFRACTIVITY>
63.926899999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.53e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dehydrovomifoliol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0302822
     RDKit          3D
(+)-Dehydrovomifoliol
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.5758    0.6055   -0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3151    0.5027    0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3244    0.7309    1.8638 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0955    0.1441   -0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9267    0.0281    0.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2679   -0.3421   -0.2144 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1204   -0.7856   -1.5004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0191   -1.4366    0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5472   -2.8192    0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0699   -1.2225    1.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5536    0.1305    1.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5462    0.3601    2.1946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044    1.2758    0.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958    0.8257   -0.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    1.9461   -1.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2580    0.3151   -1.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4862    0.0635   -1.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4132    0.1376    0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7733    1.6799   -0.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433   -0.0439   -1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8740    0.2098    1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1077   -1.7227   -1.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1096   -3.3042   -0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5560   -2.8033    0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7076   -3.4385    1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6034   -2.0334    1.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7342    1.9625    0.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2787    1.8825    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327    2.5453   -0.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1269    2.6012   -1.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3479    1.5669   -1.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9201    0.4842   -2.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2457    0.7521   -1.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3751   -0.7981   -1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 13 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
M  END

HEADER    PROTEIN                                 13-JUL-15   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-JUL-15         0                                  
HETATM    1  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.407   7.564   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.517   1.273   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.527   2.987   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.870   4.937   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000  -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      -0.119   6.117   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -1.636   5.849   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       1.334  -2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       2.324   3.490   0.000  0.00  0.00           O+0
HETATM   17  H   UNK     0       2.387   5.204   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0      -0.836   4.480   0.000  0.00  0.00           H+0
CONECT    1    9                                                            
CONECT    2   10                                                            
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5    6   10   17                                                  
CONECT    6    5   13   18                                                  
CONECT    7    9   11                                                       
CONECT    8   11   12                                                       
CONECT    9    1    7   13                                                  
CONECT   10    2    5   14                                                  
CONECT   11    7    8   15                                                  
CONECT   12    3    4    8   13                                             
CONECT   13    6    9   12   16                                             
CONECT   14   10                                                            
CONECT   15   11                                                            
CONECT   16   13                                                            
CONECT   17    5                                                            
CONECT   18    6                                                            
MASTER        0    0    0    0    0    0    0    0   18    0   36    0
END

COMPND    HMDB0302822
HETATM    1  C1  UNL     1       4.576   0.606  -0.154  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.315   0.503   0.620  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.324   0.731   1.864  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.096   0.144  -0.054  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.927   0.028   0.550  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.268  -0.342  -0.214  1.00  0.00           C  
HETATM    7  O2  UNL     1       0.120  -0.786  -1.500  1.00  0.00           O  
HETATM    8  C6  UNL     1      -1.019  -1.437   0.472  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.547  -2.819   0.277  1.00  0.00           C  
HETATM   10  C8  UNL     1      -2.070  -1.222   1.234  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.554   0.131   1.441  1.00  0.00           C  
HETATM   12  O3  UNL     1      -3.546   0.360   2.195  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.904   1.276   0.782  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.196   0.826  -0.462  1.00  0.00           C  
HETATM   15  C12 UNL     1      -0.413   1.946  -1.095  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.258   0.315  -1.444  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.486   0.063  -1.127  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.413   0.138   0.410  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.773   1.680  -0.387  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.143  -0.044  -1.138  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.874   0.210   1.604  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.108  -1.723  -1.649  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.110  -3.304  -0.538  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.556  -2.803   0.071  1.00  0.00           H  
HETATM   25  H9  UNL     1      -0.708  -3.439   1.193  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.603  -2.033   1.725  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.734   1.963   0.441  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.279   1.883   1.455  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.033   2.545  -0.265  1.00  0.00           H  
HETATM   30  H14 UNL     1      -1.127   2.601  -1.656  1.00  0.00           H  
HETATM   31  H15 UNL     1       0.348   1.567  -1.789  1.00  0.00           H  
HETATM   32  H16 UNL     1      -1.920   0.484  -2.471  1.00  0.00           H  
HETATM   33  H17 UNL     1      -3.246   0.752  -1.218  1.00  0.00           H  
HETATM   34  H18 UNL     1      -2.375  -0.798  -1.336  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3    4
CONECT    4    5    5   20
CONECT    5    6   21
CONECT    6    7    8   14
CONECT    7   22
CONECT    8    9   10   10
CONECT    9   23   24   25
CONECT   10   11   26
CONECT   11   12   12   13
CONECT   13   14   27   28
CONECT   14   15   16
CONECT   15   29   30   31
CONECT   16   32   33   34
END

HMDB0302822
     RDKit          3D
(+)-Dehydrovomifoliol
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.5758    0.6055   -0.1543 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3151    0.5027    0.6204 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3244    0.7309    1.8638 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0955    0.1441   -0.0542 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9267    0.0281    0.5505 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2679   -0.3421   -0.2144 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.1204   -0.7856   -1.5004 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0191   -1.4366    0.4722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5472   -2.8192    0.2769 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0699   -1.2225    1.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5536    0.1305    1.4413 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5462    0.3601    2.1946 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9044    1.2758    0.7821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1958    0.8257   -0.4621 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4133    1.9461   -1.0949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2580    0.3151   -1.4443 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4862    0.0635   -1.1267 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4132    0.1376    0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7733    1.6799   -0.3867 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1433   -0.0439   -1.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8740    0.2098    1.6042 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1077   -1.7227   -1.6493 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1096   -3.3042   -0.5378 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5560   -2.8033    0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7076   -3.4385    1.1929 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6034   -2.0334    1.7252 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7342    1.9625    0.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2787    1.8825    1.4551 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0327    2.5453   -0.2646 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1269    2.6012   -1.6563 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3479    1.5669   -1.7892 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9201    0.4842   -2.4711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2457    0.7521   -1.2182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3751   -0.7981   -1.3359 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  6
  6  8  1  0
  8  9  1  0
  8 10  2  0
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 14  6  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  4 20  1  0
  5 21  1  0
  7 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 13 27  1  0
 13 28  1  0
 15 29  1  0
 15 30  1  0
 15 31  1  0
 16 32  1  0
 16 33  1  0
 16 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(4S)-4-Hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-enyl]cyclohex-2-en-1-one	ChEBI
(6R)-6-Hydroxy-3-oxo-alpha-ionone	ChEBI
(6S)-6-Hydroxy-3-oxo-alpha-ionone	ChEBI
Dehydrovomifoliol	ChEBI
(6R)-6-Hydroxy-3-oxo-a-ionone	Generator
(6R)-6-Hydroxy-3-oxo-α-ionone	Generator
(6S)-6-Hydroxy-3-oxo-a-ionone	Generator
(6S)-6-Hydroxy-3-oxo-α-ionone	Generator

Chemical Formula

C₁₃H₁₈O₃

Average Molecular Weight

222.284

Monoisotopic Molecular Weight

222.12559444

IUPAC Name

(4S)-4-hydroxy-3,5,5-trimethyl-4-[(1E)-3-oxobut-1-en-1-yl]cyclohex-2-en-1-one

Traditional Name

dehydrovomifoliol

CAS Registry Number

Not Available

SMILES

[H]\C(=C(\[H])[C@@]1(O)C(C)=CC(=O)CC1(C)C)C(C)=O

InChI Identifier

InChI=1S/C13H18O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,16H,8H2,1-4H3/b6-5+/t13-/m1/s1

InChI Key

JJRYPZMXNLLZFH-URWSZGRFSA-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
Megastigmane sesquiterpenoid
Cyclofarsesane sesquiterpenoid
Ionone derivative
Cyclohexenone
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Tertiary alcohol
Ketone
Cyclic ketone
Organic oxide
Organic oxygen compound
Organooxygen compound
Alcohol
Hydrocarbon derivative
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

dehydrovomifoliol (CHEBI:4372 )
Cyclofarnesane sesquiterpenoids (C02533 )
Cyclofarnesane sesquiterpenoids (LMPR0103050009 )

Ontology

Not Available

Cereal and cereal product

Cereal

Rice (FooDB: FOOD00125)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
logP	1.41	ALOGPS
logP	1.65	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	13.37	ChemAxon
pKa (Strongest Basic)	-3.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	54.37 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.93 m³·mol⁻¹	ChemAxon
Polarizability	24.15 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
AllCCS	[M+H]+	150.474	32859911
AllCCS	[M+H-H2O]+	146.677	32859911
AllCCS	[M+Na]+	155.021	32859911
AllCCS	[M+NH4]+	154.004	32859911
AllCCS	[M-H]-	155.073	32859911
AllCCS	[M+Na-2H]-	155.77	32859911
AllCCS	[M+HCOO]-	156.637	32859911
DeepCCS	[M+H]+	153.993	30932474
DeepCCS	[M-H]-	151.597	30932474
DeepCCS	[M-2H]-	185.553	30932474
DeepCCS	[M+Na]+	160.289	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(+)-Dehydrovomifoliol,2TMS,isomer #1	CC(=O)/C=C/[C@@]1(O[Si](C)(C)C)C(C)=CC(O[Si](C)(C)C)=CC1(C)C	1903.3	Semi standard non polar	33892256
(+)-Dehydrovomifoliol,2TMS,isomer #1	CC(=O)/C=C/[C@@]1(O[Si](C)(C)C)C(C)=CC(O[Si](C)(C)C)=CC1(C)C	1830.9	Standard non polar	33892256
(+)-Dehydrovomifoliol,2TMS,isomer #1	CC(=O)/C=C/[C@@]1(O[Si](C)(C)C)C(C)=CC(O[Si](C)(C)C)=CC1(C)C	2093.0	Standard polar	33892256
(+)-Dehydrovomifoliol,2TMS,isomer #2	C=C(/C=C/[C@@]1(O[Si](C)(C)C)C(C)=CC(=O)CC1(C)C)O[Si](C)(C)C	1978.6	Semi standard non polar	33892256
(+)-Dehydrovomifoliol,2TMS,isomer #2	C=C(/C=C/[C@@]1(O[Si](C)(C)C)C(C)=CC(=O)CC1(C)C)O[Si](C)(C)C	1898.7	Standard non polar	33892256
(+)-Dehydrovomifoliol,2TMS,isomer #2	C=C(/C=C/[C@@]1(O[Si](C)(C)C)C(C)=CC(=O)CC1(C)C)O[Si](C)(C)C	2039.9	Standard polar	33892256
(+)-Dehydrovomifoliol,2TMS,isomer #3	C=C(/C=C/[C@@]1(O)C(C)=CC(O[Si](C)(C)C)=CC1(C)C)O[Si](C)(C)C	1910.6	Semi standard non polar	33892256
(+)-Dehydrovomifoliol,2TMS,isomer #3	C=C(/C=C/[C@@]1(O)C(C)=CC(O[Si](C)(C)C)=CC1(C)C)O[Si](C)(C)C	1912.4	Standard non polar	33892256
(+)-Dehydrovomifoliol,2TMS,isomer #3	C=C(/C=C/[C@@]1(O)C(C)=CC(O[Si](C)(C)C)=CC1(C)C)O[Si](C)(C)C	2305.3	Standard polar	33892256
(+)-Dehydrovomifoliol,3TMS,isomer #1	C=C(/C=C/[C@@]1(O[Si](C)(C)C)C(C)=CC(O[Si](C)(C)C)=CC1(C)C)O[Si](C)(C)C	1936.6	Semi standard non polar	33892256
(+)-Dehydrovomifoliol,3TMS,isomer #1	C=C(/C=C/[C@@]1(O[Si](C)(C)C)C(C)=CC(O[Si](C)(C)C)=CC1(C)C)O[Si](C)(C)C	1979.6	Standard non polar	33892256
(+)-Dehydrovomifoliol,3TMS,isomer #1	C=C(/C=C/[C@@]1(O[Si](C)(C)C)C(C)=CC(O[Si](C)(C)C)=CC1(C)C)O[Si](C)(C)C	2085.0	Standard polar	33892256
(+)-Dehydrovomifoliol,2TBDMS,isomer #1	CC(=O)/C=C/[C@@]1(O[Si](C)(C)C(C)(C)C)C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C	2361.5	Semi standard non polar	33892256
(+)-Dehydrovomifoliol,2TBDMS,isomer #1	CC(=O)/C=C/[C@@]1(O[Si](C)(C)C(C)(C)C)C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C	2303.0	Standard non polar	33892256
(+)-Dehydrovomifoliol,2TBDMS,isomer #1	CC(=O)/C=C/[C@@]1(O[Si](C)(C)C(C)(C)C)C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C	2310.4	Standard polar	33892256
(+)-Dehydrovomifoliol,2TBDMS,isomer #2	C=C(/C=C/[C@@]1(O[Si](C)(C)C(C)(C)C)C(C)=CC(=O)CC1(C)C)O[Si](C)(C)C(C)(C)C	2468.6	Semi standard non polar	33892256
(+)-Dehydrovomifoliol,2TBDMS,isomer #2	C=C(/C=C/[C@@]1(O[Si](C)(C)C(C)(C)C)C(C)=CC(=O)CC1(C)C)O[Si](C)(C)C(C)(C)C	2376.9	Standard non polar	33892256
(+)-Dehydrovomifoliol,2TBDMS,isomer #2	C=C(/C=C/[C@@]1(O[Si](C)(C)C(C)(C)C)C(C)=CC(=O)CC1(C)C)O[Si](C)(C)C(C)(C)C	2267.5	Standard polar	33892256
(+)-Dehydrovomifoliol,2TBDMS,isomer #3	C=C(/C=C/[C@@]1(O)C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C)O[Si](C)(C)C(C)(C)C	2389.9	Semi standard non polar	33892256
(+)-Dehydrovomifoliol,2TBDMS,isomer #3	C=C(/C=C/[C@@]1(O)C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C)O[Si](C)(C)C(C)(C)C	2374.6	Standard non polar	33892256
(+)-Dehydrovomifoliol,2TBDMS,isomer #3	C=C(/C=C/[C@@]1(O)C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C)O[Si](C)(C)C(C)(C)C	2532.9	Standard polar	33892256
(+)-Dehydrovomifoliol,3TBDMS,isomer #1	C=C(/C=C/[C@@]1(O[Si](C)(C)C(C)(C)C)C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C)O[Si](C)(C)C(C)(C)C	2627.8	Semi standard non polar	33892256
(+)-Dehydrovomifoliol,3TBDMS,isomer #1	C=C(/C=C/[C@@]1(O[Si](C)(C)C(C)(C)C)C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C)O[Si](C)(C)C(C)(C)C	2622.4	Standard non polar	33892256
(+)-Dehydrovomifoliol,3TBDMS,isomer #1	C=C(/C=C/[C@@]1(O[Si](C)(C)C(C)(C)C)C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C)O[Si](C)(C)C(C)(C)C	2361.0	Standard polar	33892256

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dehydrovomifoliol 10V, Positive-QTOF	splash10-0ab9-1390000000-4e60e0949700e5a7866c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dehydrovomifoliol 20V, Positive-QTOF	splash10-0a4r-6960000000-13f3c7a12fb342f032ba	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dehydrovomifoliol 40V, Positive-QTOF	splash10-0a4u-9400000000-e6f96a4aba3f87be5d0f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dehydrovomifoliol 10V, Negative-QTOF	splash10-00di-1290000000-532cf596c2cdb0015193	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dehydrovomifoliol 20V, Negative-QTOF	splash10-00di-3590000000-de4cf83db1750d791a7a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dehydrovomifoliol 40V, Negative-QTOF	splash10-0zg0-9720000000-35064bd3d2f1d6e41fb0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dehydrovomifoliol 10V, Positive-QTOF	splash10-0a4i-0490000000-654708f6f22dc249fdd8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dehydrovomifoliol 20V, Positive-QTOF	splash10-052u-7930000000-c75cc836c4e99d9cb5b8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dehydrovomifoliol 40V, Positive-QTOF	splash10-0006-9200000000-386e524a1645cf2f1b7a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dehydrovomifoliol 10V, Negative-QTOF	splash10-00di-0690000000-ed548d7a227093275795	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dehydrovomifoliol 20V, Negative-QTOF	splash10-0udi-0900000000-5a5f74386d1c4a0f34f0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-Dehydrovomifoliol 40V, Negative-QTOF	splash10-0f79-3930000000-6051e849c6c0c241b22f	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB006379

KNApSAcK ID

Not Available

Chemspider ID

599941

KEGG Compound ID

C02533

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

688492

PDB ID

Not Available

ChEBI ID

4372

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for (+)-Dehydrovomifoliol (HMDB0302822)

MOL for HMDB0302822 ((+)-Dehydrovomifoliol)

3D MOL for HMDB0302822 ((+)-Dehydrovomifoliol)

3D SDF for HMDB0302822 ((+)-Dehydrovomifoliol)

3D-SDF for HMDB0302822 ((+)-Dehydrovomifoliol)

PDB for HMDB0302822 ((+)-Dehydrovomifoliol)

3D PDB for HMDB0302822 ((+)-Dehydrovomifoliol)

SMILES for HMDB0302822 ((+)-Dehydrovomifoliol)

INCHI for HMDB0302822 ((+)-Dehydrovomifoliol)

Structure for HMDB0302822 ((+)-Dehydrovomifoliol)

3D Structure for HMDB0302822 ((+)-Dehydrovomifoliol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra