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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 02:53:59 UTC

Update Date

2021-09-24 02:53:59 UTC

HMDB ID

HMDB0303570

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Vomifoliol

Description

Vomifoliol, also known as (+/-)-6-hydroxy-3-oxo-alpha-ionol, is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Vomifoliol is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). Vomifoliol is a fruity tasting compound found in common grape, which makes vomifoliol a potential biomarker for the consumption of this food product.

Structure

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

HMDB0303570
     RDKit          3D
Vomifoliol
 36 36  0  0  0  0  0  0  0  0999 V2000
   -0.8392    2.7996    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678    1.3778   -0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4281    1.1929   -1.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5769   -0.1500   -2.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9041   -0.3309   -3.2999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342   -1.3055   -1.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3413   -0.9245    0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9190   -2.1149    1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7894   -0.6246    0.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5607    0.3136    0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0115    0.7316    1.8266 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8849    0.1256    0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6541    0.2441   -0.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1304    0.0645   -0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5552   -0.9728    0.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7023    1.3083   -0.1267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4494    2.9010    1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1619    3.5218   -0.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292    2.9123    0.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7062    2.0248   -2.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004   -2.0041   -1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4379   -1.8869   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4503   -3.0032    0.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1891   -2.2757    1.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2694   -2.0263    2.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8570   -0.1499    1.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1726    0.1151   -0.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4323   -1.5170    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995    1.3353    2.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4009   -0.1152    1.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1540    0.4832   -1.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4478   -0.2581   -1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -0.6468    1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6541   -1.1007    0.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0174   -1.9117    0.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7204    1.8676   -0.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 10  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  6 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
M  END

  Mrv0541 02241219482D          

 16 16  0  0  0  0            999 V2000
   -1.7847    0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7847   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5002   -1.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0704   -1.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563   -0.8249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591   -1.2377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6002    1.0464    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0704    0.4135    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5380    1.0450    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3563    0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3577    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0719    0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860    0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002    0.0006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7860    1.2377    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591   -0.4120    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  8  1  0  0  0  0
  2  3  2  0  0  0  0
  2  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 16  1  0  0  0  0
 11 12  2  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303570

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(O)\C=C\C1(O)C(C)=CC(=O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,10,14,16H,8H2,1-4H3/b6-5+

> <INCHI_KEY>
KPQMCAKZRXOZLB-AATRIKPKSA-N

> <FORMULA>
C13H20O3

> <MOLECULAR_WEIGHT>
224.2961

> <EXACT_MASS>
224.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.787406125510618

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-hydroxy-4-[(1E)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one

> <ALOGPS_LOGP>
1.24

> <JCHEM_LOGP>
1.4189990350000001

> <ALOGPS_LOGS>
-1.97

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.318580056729672

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.40300283457503

> <JCHEM_PKA_STRONGEST_BASIC>
-2.6687152382363992

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
64.9272

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.43e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
vomifoliol

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303570
     RDKit          3D
Vomifoliol
 36 36  0  0  0  0  0  0  0  0999 V2000
   -0.8392    2.7996    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678    1.3778   -0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4281    1.1929   -1.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5769   -0.1500   -2.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9041   -0.3309   -3.2999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342   -1.3055   -1.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3413   -0.9245    0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9190   -2.1149    1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7894   -0.6246    0.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5607    0.3136    0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0115    0.7316    1.8266 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8849    0.1256    0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6541    0.2441   -0.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1304    0.0645   -0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5552   -0.9728    0.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7023    1.3083   -0.1267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4494    2.9010    1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1619    3.5218   -0.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292    2.9123    0.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7062    2.0248   -2.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004   -2.0041   -1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4379   -1.8869   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4503   -3.0032    0.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1891   -2.2757    1.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2694   -2.0263    2.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8570   -0.1499    1.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1726    0.1151   -0.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4323   -1.5170    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995    1.3353    2.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4009   -0.1152    1.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1540    0.4832   -1.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4478   -0.2581   -1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -0.6468    1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6541   -1.1007    0.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0174   -1.9117    0.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7204    1.8676   -0.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 10  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  6 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  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      -3.331   0.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.331  -1.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.667  -2.310   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.998  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.665  -1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.670  -2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.987   1.953   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.998   0.772   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.004   1.951   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.665   0.001   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.668   0.769   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.001   0.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.334   0.769   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.667   0.001   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       3.334   2.310   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.670  -0.769   0.000  0.00  0.00           O+0
CONECT    1    2    8                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6   10                                                  
CONECT    6    5                                                            
CONECT    7    8                                                            
CONECT    8    1    7    9   10                                             
CONECT    9    8                                                            
CONECT   10    5    8   11   16                                             
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
CONECT   16   10                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0303570
HETATM    1  C1  UNL     1      -0.839   2.800   0.082  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.968   1.378  -0.392  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.428   1.193  -1.596  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.577  -0.150  -2.114  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.904  -0.331  -3.300  1.00  0.00           O  
HETATM    6  C5  UNL     1      -1.334  -1.306  -1.212  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.341  -0.924   0.235  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.919  -2.115   1.053  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.789  -0.625   0.618  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.561   0.314   0.549  1.00  0.00           C  
HETATM   11  O2  UNL     1      -1.011   0.732   1.827  1.00  0.00           O  
HETATM   12  C10 UNL     1       0.885   0.126   0.647  1.00  0.00           C  
HETATM   13  C11 UNL     1       1.654   0.244  -0.431  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.130   0.064  -0.395  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.555  -0.973   0.605  1.00  0.00           C  
HETATM   16  O3  UNL     1       3.702   1.308  -0.127  1.00  0.00           O  
HETATM   17  H1  UNL     1      -1.449   2.901   1.018  1.00  0.00           H  
HETATM   18  H2  UNL     1      -1.162   3.522  -0.671  1.00  0.00           H  
HETATM   19  H3  UNL     1       0.229   2.912   0.376  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.706   2.025  -2.229  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.200  -2.004  -1.373  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.438  -1.887  -1.515  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.450  -3.003   0.623  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.189  -2.276   1.014  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.269  -2.026   2.108  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.857  -0.150   1.619  1.00  0.00           H  
HETATM   27  H11 UNL     1      -3.173   0.115  -0.116  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.432  -1.517   0.530  1.00  0.00           H  
HETATM   29  H13 UNL     1      -0.299   1.335   2.186  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.401  -0.115   1.579  1.00  0.00           H  
HETATM   31  H15 UNL     1       1.154   0.483  -1.364  1.00  0.00           H  
HETATM   32  H16 UNL     1       3.448  -0.258  -1.389  1.00  0.00           H  
HETATM   33  H17 UNL     1       3.369  -0.647   1.651  1.00  0.00           H  
HETATM   34  H18 UNL     1       4.654  -1.101   0.497  1.00  0.00           H  
HETATM   35  H19 UNL     1       3.017  -1.912   0.365  1.00  0.00           H  
HETATM   36  H20 UNL     1       3.720   1.868  -0.961  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3   10
CONECT    3    4   20
CONECT    4    5    5    6
CONECT    6    7   21   22
CONECT    7    8    9   10
CONECT    8   23   24   25
CONECT    9   26   27   28
CONECT   10   11   12
CONECT   11   29
CONECT   12   13   13   30
CONECT   13   14   31
CONECT   14   15   16   32
CONECT   15   33   34   35
CONECT   16   36
END

HMDB0303570
     RDKit          3D
Vomifoliol
 36 36  0  0  0  0  0  0  0  0999 V2000
   -0.8392    2.7996    0.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9678    1.3778   -0.3920 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4281    1.1929   -1.5958 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5769   -0.1500   -2.1138 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9041   -0.3309   -3.2999 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3342   -1.3055   -1.2119 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3413   -0.9245    0.2349 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9190   -2.1149    1.0534 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7894   -0.6246    0.6178 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5607    0.3136    0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0115    0.7316    1.8266 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8849    0.1256    0.6466 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6541    0.2441   -0.4308 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1304    0.0645   -0.3947 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5552   -0.9728    0.6047 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7023    1.3083   -0.1267 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4494    2.9010    1.0183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1619    3.5218   -0.6711 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2292    2.9123    0.3761 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7062    2.0248   -2.2286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2004   -2.0041   -1.3729 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4379   -1.8869   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4503   -3.0032    0.6230 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1891   -2.2757    1.0138 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2694   -2.0263    2.1077 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8570   -0.1499    1.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1726    0.1151   -0.1164 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4323   -1.5170    0.5304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2995    1.3353    2.1861 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4009   -0.1152    1.5790 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1540    0.4832   -1.3636 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4478   -0.2581   -1.3885 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3691   -0.6468    1.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6541   -1.1007    0.4970 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0174   -1.9117    0.3653 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7204    1.8676   -0.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 10  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  6 21  1  0
  6 22  1  0
  8 23  1  0
  8 24  1  0
  8 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+/-)-6-hydroxy-3-oxo-alpha-ionol	ChEBI
(+/-)-6-hydroxy-3-oxo-a-ionol	Generator
(+/-)-6-hydroxy-3-oxo-α-ionol	Generator

Chemical Formula

C₁₃H₂₀O₃

Average Molecular Weight

224.2961

Monoisotopic Molecular Weight

224.141244506

IUPAC Name

4-hydroxy-4-[(1E)-3-hydroxybut-1-en-1-yl]-3,5,5-trimethylcyclohex-2-en-1-one

Traditional Name

vomifoliol

CAS Registry Number

Not Available

SMILES

CC(O)\C=C\C1(O)C(C)=CC(=O)CC1(C)C

InChI Identifier

InChI=1S/C13H20O3/c1-9-7-11(15)8-12(3,4)13(9,16)6-5-10(2)14/h5-7,10,14,16H,8H2,1-4H3/b6-5+

InChI Key

KPQMCAKZRXOZLB-AATRIKPKSA-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
Cyclofarsesane sesquiterpenoid
Megastigmane sesquiterpenoid
Ionone derivative
Cyclohexenone
Tertiary alcohol
Ketone
Secondary alcohol
Cyclic ketone
Alcohol
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organic oxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

fenchane monoterpenoid (CHEBI:28258 )

Ontology

Physiological effect

Organoleptic effect

Odor

Fruity

Disposition

Source

Exogenous

Exogenous (HMDB: HMDB0303570)

Food

Fruit

Berry

Common grape (FooDB: FOOD00204)

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	1.24	ALOGPS
logP	1.42	ChemAxon
logS	-2	ALOGPS
pKa (Strongest Acidic)	13.4	ChemAxon
pKa (Strongest Basic)	-2.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	57.53 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	64.93 m³·mol⁻¹	ChemAxon
Polarizability	24.79 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]+	152.564	32859911
AllCCS	[M+H-H2O]+	148.778	32859911
AllCCS	[M+Na]+	157.098	32859911
AllCCS	[M+NH4]+	156.084	32859911
AllCCS	[M-H]-	156.195	32859911
AllCCS	[M+Na-2H]-	156.971	32859911
AllCCS	[M+HCOO]-	157.927	32859911
DeepCCS	[M+H]+	159.151	30932474
DeepCCS	[M-H]-	156.755	30932474
DeepCCS	[M-2H]-	189.701	30932474
DeepCCS	[M+Na]+	165.115	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Vomifoliol,3TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)(C)C1(/C=C/C(C)O[Si](C)(C)C)O[Si](C)(C)C	1910.1	Semi standard non polar	33892256
Vomifoliol,3TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)(C)C1(/C=C/C(C)O[Si](C)(C)C)O[Si](C)(C)C	1958.6	Standard non polar	33892256
Vomifoliol,3TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)(C)C1(/C=C/C(C)O[Si](C)(C)C)O[Si](C)(C)C	2038.6	Standard polar	33892256
Vomifoliol,3TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C1(/C=C/C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2602.7	Semi standard non polar	33892256
Vomifoliol,3TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C1(/C=C/C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2589.7	Standard non polar	33892256
Vomifoliol,3TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C1(/C=C/C(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2319.3	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 - Vomifoliol 10V, Positive-QTOF	splash10-0a4i-1290000000-7605c7a6e9c95681e7e0	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vomifoliol 20V, Positive-QTOF	splash10-0a4r-6940000000-4afb0a1b0e2f552a476e	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vomifoliol 40V, Positive-QTOF	splash10-0a4r-9300000000-a3e23e3aa33fc7dc28e6	2019-02-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vomifoliol 10V, Negative-QTOF	splash10-00di-0290000000-d66ee0a3b03f94ba960f	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vomifoliol 20V, Negative-QTOF	splash10-05fr-2290000000-76c959bbc2d98521ffe1	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vomifoliol 40V, Negative-QTOF	splash10-0k9i-9810000000-27d3420b9d1cc7ea64af	2019-02-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vomifoliol 10V, Positive-QTOF	splash10-0a70-0980000000-2ebd3ec8948a8222407e	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vomifoliol 20V, Positive-QTOF	splash10-0a4i-7930000000-a3c1df3373d362cc523d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vomifoliol 40V, Positive-QTOF	splash10-059x-9200000000-447bb5645c4c98e1baab	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vomifoliol 10V, Negative-QTOF	splash10-0fmi-0970000000-4a92efd55a33f5edca8b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vomifoliol 20V, Negative-QTOF	splash10-0udi-0900000000-2951434f9e08e5e0e801	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Vomifoliol 40V, Negative-QTOF	splash10-0m0i-1920000000-fe2aae318254611b3e62	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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

28258

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 Vomifoliol (HMDB0303570)

MOL for HMDB0303570 (Vomifoliol)

3D MOL for HMDB0303570 (Vomifoliol)

3D SDF for HMDB0303570 (Vomifoliol)

3D-SDF for HMDB0303570 (Vomifoliol)

PDB for HMDB0303570 (Vomifoliol)

3D PDB for HMDB0303570 (Vomifoliol)

SMILES for HMDB0303570 (Vomifoliol)

INCHI for HMDB0303570 (Vomifoliol)

Structure for HMDB0303570 (Vomifoliol)

3D Structure for HMDB0303570 (Vomifoliol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra