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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:59:43 UTC

Update Date

2022-03-07 02:55:04 UTC

HMDB ID

HMDB0036819

Secondary Accession Numbers

HMDB36819

Metabolite Identification

Common Name

Dehydrovomifoliol

Description

Dehydrovomifoliol 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 Dehydrovomifoliol.

Structure

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

HMDB0036819
     RDKit          3D
Dehydrovomifoliol
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.0268   -1.0460   -1.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1976   -0.6293    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7546   -0.5783    1.2531 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7975   -0.3054   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0035    0.0745    0.9056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980    0.4161    0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9096    0.6943    2.0476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6937    1.5908   -0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835    2.4577   -0.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9828    1.8594   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9661    0.9806    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0858    1.4146    0.8115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6578   -0.4518    0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2392   -0.7335    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2554   -0.7427   -1.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7472   -2.0574    0.7009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5958   -0.7129   -1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0571   -0.6067   -0.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1724   -2.1440   -0.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3340   -0.3555   -1.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878    0.1181    1.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2322    1.0670    2.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1515    2.3822   -1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0865    3.5476   -0.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3236    2.2829   -0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3558    2.6879   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3953   -1.1301    0.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5777   -0.5321    1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2971   -0.9517   -1.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6419   -1.5810   -1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9716    0.2166   -1.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819   -2.7837    0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0267   -2.4237   -0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3096   -2.0245    1.7199 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  0
  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


  Mrv0541 02241217432D          

 16 16  0  0  0  0            999 V2000
   -1.7848    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7848   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5004   -1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706   -1.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3564   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591   -1.2378    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6004    1.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0706    0.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5380    1.0466    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3564    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591    0.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0720    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.4136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5004    0.0007    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.2378    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3591   -0.4122    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  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036819

> <DATABASE_NAME>
hmdb

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

> <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+

> <INCHI_KEY>
JJRYPZMXNLLZFH-AATRIKPKSA-N

> <FORMULA>
C13H18O3

> <MOLECULAR_WEIGHT>
222.2802

> <EXACT_MASS>
222.125594442

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.11749053754903

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
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>
6-hydroxy-3-oxo-α-ionone

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0036819
     RDKit          3D
Dehydrovomifoliol
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.0268   -1.0460   -1.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1976   -0.6293    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7546   -0.5783    1.2531 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7975   -0.3054   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0035    0.0745    0.9056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980    0.4161    0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9096    0.6943    2.0476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6937    1.5908   -0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835    2.4577   -0.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9828    1.8594   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9661    0.9806    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0858    1.4146    0.8115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6578   -0.4518    0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2392   -0.7335    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2554   -0.7427   -1.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7472   -2.0574    0.7009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5958   -0.7129   -1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0571   -0.6067   -0.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1724   -2.1440   -0.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3340   -0.3555   -1.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878    0.1181    1.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2322    1.0670    2.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1515    2.3822   -1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0865    3.5476   -0.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3236    2.2829   -0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3558    2.6879   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3953   -1.1301    0.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5777   -0.5321    1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2971   -0.9517   -1.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6419   -1.5810   -1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9716    0.2166   -1.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819   -2.7837    0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0267   -2.4237   -0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3096   -2.0245    1.7199 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  0
  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                                 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      -3.332   0.001   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.332  -1.540   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.667  -2.311   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -1.998  -2.311   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  -2.311   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.987   1.954   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   1.954   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       0.670   0.772   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   0.772   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   2.311   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    HMDB0036819
HETATM    1  C1  UNL     1       4.027  -1.046  -1.020  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.198  -0.629   0.134  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.755  -0.578   1.253  1.00  0.00           O  
HETATM    4  C3  UNL     1       1.797  -0.305  -0.091  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.003   0.075   0.906  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.398   0.416   0.780  1.00  0.00           C  
HETATM    7  O2  UNL     1      -0.910   0.694   2.048  1.00  0.00           O  
HETATM    8  C6  UNL     1      -0.694   1.591  -0.065  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.283   2.458  -0.725  1.00  0.00           C  
HETATM   10  C8  UNL     1      -1.983   1.859  -0.219  1.00  0.00           C  
HETATM   11  C9  UNL     1      -2.966   0.981   0.450  1.00  0.00           C  
HETATM   12  O3  UNL     1      -4.086   1.415   0.811  1.00  0.00           O  
HETATM   13  C10 UNL     1      -2.658  -0.452   0.717  1.00  0.00           C  
HETATM   14  C11 UNL     1      -1.239  -0.734   0.209  1.00  0.00           C  
HETATM   15  C12 UNL     1      -1.255  -0.743  -1.281  1.00  0.00           C  
HETATM   16  C13 UNL     1      -0.747  -2.057   0.701  1.00  0.00           C  
HETATM   17  H1  UNL     1       3.596  -0.713  -1.993  1.00  0.00           H  
HETATM   18  H2  UNL     1       5.057  -0.607  -0.986  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.172  -2.144  -0.972  1.00  0.00           H  
HETATM   20  H4  UNL     1       1.334  -0.356  -1.067  1.00  0.00           H  
HETATM   21  H5  UNL     1       1.488   0.118   1.872  1.00  0.00           H  
HETATM   22  H6  UNL     1      -0.232   1.067   2.664  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.152   2.382  -1.833  1.00  0.00           H  
HETATM   24  H8  UNL     1       0.087   3.548  -0.499  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.324   2.283  -0.409  1.00  0.00           H  
HETATM   26  H10 UNL     1      -2.356   2.688  -0.810  1.00  0.00           H  
HETATM   27  H11 UNL     1      -3.395  -1.130   0.295  1.00  0.00           H  
HETATM   28  H12 UNL     1      -2.578  -0.532   1.840  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.297  -0.952  -1.623  1.00  0.00           H  
HETATM   30  H14 UNL     1      -0.642  -1.581  -1.658  1.00  0.00           H  
HETATM   31  H15 UNL     1      -0.972   0.217  -1.752  1.00  0.00           H  
HETATM   32  H16 UNL     1      -1.582  -2.784   0.627  1.00  0.00           H  
HETATM   33  H17 UNL     1       0.027  -2.424  -0.024  1.00  0.00           H  
HETATM   34  H18 UNL     1      -0.310  -2.025   1.720  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

HMDB0036819
     RDKit          3D
Dehydrovomifoliol
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.0268   -1.0460   -1.0203 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1976   -0.6293    0.1341 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7546   -0.5783    1.2531 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.7975   -0.3054   -0.0905 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0035    0.0745    0.9056 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3980    0.4161    0.7798 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9096    0.6943    2.0476 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6937    1.5908   -0.0646 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2835    2.4577   -0.7251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9828    1.8594   -0.2194 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9661    0.9806    0.4498 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0858    1.4146    0.8115 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6578   -0.4518    0.7166 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2392   -0.7335    0.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2554   -0.7427   -1.2806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7472   -2.0574    0.7009 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5958   -0.7129   -1.9934 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0571   -0.6067   -0.9855 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1724   -2.1440   -0.9721 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3340   -0.3555   -1.0668 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4878    0.1181    1.8722 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2322    1.0670    2.6639 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1515    2.3822   -1.8334 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0865    3.5476   -0.4994 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3236    2.2829   -0.4089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3558    2.6879   -0.8097 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3953   -1.1301    0.2947 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5777   -0.5321    1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2971   -0.9517   -1.6232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6419   -1.5810   -1.6575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9716    0.2166   -1.7517 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5819   -2.7837    0.6273 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0267   -2.4237   -0.0238 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3096   -2.0245    1.7199 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  0
  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
(+/-)-6-hydroxy-3-oxo-alpha-ionone	ChEBI
(6Rs)-6-Hydroxy-9-apo-epsilon-carotene-3,9-dione	ChEBI
6-Hydroxy-3-oxo-alpha-ionone	ChEBI
(+/-)-6-hydroxy-3-oxo-a-ionone	Generator
(+/-)-6-hydroxy-3-oxo-α-ionone	Generator
6-Hydroxy-3-oxo-a-ionone	Generator
6-Hydroxy-3-oxo-α-ionone	Generator
(6R)-6-Hydroxy-3-oxo-alpha-ionone	HMDB
(6S)-6-Hydroxy-3-oxo-alpha-ionone	HMDB
(6S)-Dehydrovomifoliol	HMDB
6-Hydroxy-4,7-megastigmadiene-3,9-dione	HMDB

Chemical Formula

C₁₃H₁₈O₃

Average Molecular Weight

222.2802

Monoisotopic Molecular Weight

222.125594442

IUPAC Name

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

Traditional Name

6-hydroxy-3-oxo-α-ionone

CAS Registry Number

15764-81-5

SMILES

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

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+

InChI Key

JJRYPZMXNLLZFH-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
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

enone (CHEBI:18429 )
fenchane monoterpenoid (CHEBI:18429 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036819)

Source

Endogenous

Endogenous (HMDB: HMDB0036819)

Plant

Plant (HMDB: HMDB0036819)
Poaceae (HMDB: HMDB0036819)

Animal

Animal (HMDB: HMDB0036819)

Exogenous

Food

Food (HMDB: HMDB0036819)

Cereal and cereal product

Cereal product

Breakfast cereal (FooDB: FOOD00270)

Cereals and cereal products (FooDB: FOOD00858)

Tea

Fruit

Berry

Common grape (FooDB: FOOD00204)

Exogenous (HMDB: HMDB0036819)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036819)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036819)

Lipid metabolism pathway (HMDB: HMDB0036819)

Cellular process

Cell signaling (HMDB: HMDB0036819)

Biochemical process

Lipid transport (HMDB: HMDB0036819)

Role

Biological role

Energy source (HMDB: HMDB0036819)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036819)

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
Water Solubility	0.55 g/L	ALOGPS
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	24.12 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
DeepCCS	[M+H]+	157.792	30932474
DeepCCS	[M-H]-	155.396	30932474
DeepCCS	[M-2H]-	188.536	30932474
DeepCCS	[M+Na]+	163.704	30932474
AllCCS	[M+H]+	150.3	32859911
AllCCS	[M+H-H2O]+	146.5	32859911
AllCCS	[M+NH4]+	153.9	32859911
AllCCS	[M+Na]+	154.9	32859911
AllCCS	[M-H]-	155.1	32859911
AllCCS	[M+Na-2H]-	155.8	32859911
AllCCS	[M+HCOO]-	156.6	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.	4.54 minutes	32390414
Predicted by Siyang on May 30, 2022	10.5276 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.4 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	1793.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	251.9 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	131.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	157.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	56.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	404.9 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	415.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	62.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	771.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	315.6 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	1179.9 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	246.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	269.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	289.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	241.2 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	11.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dehydrovomifoliol	CC(=O)\C=C\C1(O)C(C)=CC(=O)CC1(C)C	3128.8	Standard polar	33892256
Dehydrovomifoliol	CC(=O)\C=C\C1(O)C(C)=CC(=O)CC1(C)C	1726.3	Standard non polar	33892256
Dehydrovomifoliol	CC(=O)\C=C\C1(O)C(C)=CC(=O)CC1(C)C	1808.6	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dehydrovomifoliol,1TMS,isomer #1	CC(=O)/C=C/C1(O[Si](C)(C)C)C(C)=CC(=O)CC1(C)C	1936.8	Semi standard non polar	33892256
Dehydrovomifoliol,1TMS,isomer #2	CC(=O)/C=C/C1(O)C(C)=CC(O[Si](C)(C)C)=CC1(C)C	1890.3	Semi standard non polar	33892256
Dehydrovomifoliol,1TMS,isomer #3	C=C(/C=C/C1(O)C(C)=CC(=O)CC1(C)C)O[Si](C)(C)C	1936.4	Semi standard non polar	33892256
Dehydrovomifoliol,2TMS,isomer #1	CC(=O)/C=C/C1(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/C1(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 #2	C=C(/C=C/C1(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/C1(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 #3	C=C(/C=C/C1(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/C1(O)C(C)=CC(O[Si](C)(C)C)=CC1(C)C)O[Si](C)(C)C	1912.4	Standard non polar	33892256
Dehydrovomifoliol,3TMS,isomer #1	C=C(/C=C/C1(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/C1(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,1TBDMS,isomer #1	CC(=O)/C=C/C1(O[Si](C)(C)C(C)(C)C)C(C)=CC(=O)CC1(C)C	2188.8	Semi standard non polar	33892256
Dehydrovomifoliol,1TBDMS,isomer #2	CC(=O)/C=C/C1(O)C(C)=CC(O[Si](C)(C)C(C)(C)C)=CC1(C)C	2142.9	Semi standard non polar	33892256
Dehydrovomifoliol,1TBDMS,isomer #3	C=C(/C=C/C1(O)C(C)=CC(=O)CC1(C)C)O[Si](C)(C)C(C)(C)C	2180.3	Semi standard non polar	33892256
Dehydrovomifoliol,2TBDMS,isomer #1	CC(=O)/C=C/C1(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/C1(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 #2	C=C(/C=C/C1(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/C1(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 #3	C=C(/C=C/C1(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/C1(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,3TBDMS,isomer #1	C=C(/C=C/C1(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/C1(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

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrovomifoliol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0gei-9710000000-71dac861fd9b65e2d18c	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrovomifoliol GC-MS (1 TMS) - 70eV, Positive	splash10-0fb9-8190000000-ff7f8fb97adf44d08e88	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dehydrovomifoliol 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 - 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, Negative-QTOF	splash10-00di-0690000000-6bd57ffcd2aa5ffca0ca	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrovomifoliol 20V, Negative-QTOF	splash10-0udi-0900000000-f4626d35adcb87052b67	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrovomifoliol 40V, Negative-QTOF	splash10-000i-2930000000-0fe242cb038d9fc55cf1	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrovomifoliol 10V, Positive-QTOF	splash10-0a4i-0490000000-04e09a17500bf5e22c21	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrovomifoliol 20V, Positive-QTOF	splash10-0a4u-8940000000-0a2f05b6a7456fd9b0e6	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dehydrovomifoliol 40V, Positive-QTOF	splash10-052f-9100000000-692a72f493ddf04fe18f	2021-09-25	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

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

5280662

PDB ID

Not Available

ChEBI ID

18429

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
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Showing metabocard for Dehydrovomifoliol (HMDB0036819)

MOL for HMDB0036819 (Dehydrovomifoliol)

3D MOL for HMDB0036819 (Dehydrovomifoliol)

3D SDF for HMDB0036819 (Dehydrovomifoliol)

3D-SDF for HMDB0036819 (Dehydrovomifoliol)

PDB for HMDB0036819 (Dehydrovomifoliol)

3D PDB for HMDB0036819 (Dehydrovomifoliol)

SMILES for HMDB0036819 (Dehydrovomifoliol)

INCHI for HMDB0036819 (Dehydrovomifoliol)

Structure for HMDB0036819 (Dehydrovomifoliol)

3D Structure for HMDB0036819 (Dehydrovomifoliol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra