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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 04:46:11 UTC

Update Date

2021-09-24 04:46:11 UTC

HMDB ID

HMDB0303805

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3-Oxo-alpha-ionol

Description

3-oxo-alpha-ionol is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. 3-oxo-alpha-ionol is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). 3-oxo-alpha-ionol is a spice tasting compound found in common grape, which makes 3-oxo-alpha-ionol a potential biomarker for the consumption of this food product. 3-oxo-alpha-ionol may be a unique S.cerevisiae (yeast) metabolite.

Structure

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

HMDB0303805
     RDKit          3D
3-Oxo-alpha-ionol
 35 35  0  0  0  0  0  0  0  0999 V2000
   -0.0438    1.1743    2.6469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6836    0.9749    1.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3069    1.9893    0.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9147    1.7273   -0.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8392    2.6223   -1.4761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5713    0.4178   -0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6381   -0.6720   -0.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0064   -1.2570   -1.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5481   -1.8136    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184   -0.3277    0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7839   -0.6149    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7825    0.2351    0.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1639   -0.0283   -0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4394    0.6320   -1.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4560   -1.3704   -0.2966 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5191    2.0994    2.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6356    0.3192    2.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858    1.1554    3.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3276    2.9476    1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8881    0.2348   -1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4591    0.4015   -0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1308   -0.6357   -1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7270   -1.2179   -2.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7207   -2.3138   -1.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5508   -1.7487   -0.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1218   -2.7934   -0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6532   -1.6754    1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7118   -1.0946    1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9505   -1.5497   -0.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5916    1.1627    0.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8623    0.4101    0.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8406    1.6733   -1.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5351    0.6685   -2.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1995    0.0540   -2.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4872   -1.7860    0.6059 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
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 10  2  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  6 20  1  0
  6 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
M  END


  Mrv0541 02241221572D          

 15 15  0  0  0  0            999 V2000
   -1.7754    0.0495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7906   -0.7754    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0826   -1.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3608   -0.8001    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3457   -1.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5110   -1.1756    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3457    0.0247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3746    0.4234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0812   -0.0014    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8030    0.4000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8181    1.2249    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110   -0.0247    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5733    1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0537    0.4495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5120    1.0722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 14  1  0  0  0  0
  2  3  1  0  0  0  0
  2  6  2  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7 14  1  0  0  0  0
  8  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 10 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303805

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(O)\C=C\C1C(C)=CC(=O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-7,10,12,14H,8H2,1-4H3/b6-5+

> <INCHI_KEY>
MDCGEAGEQVMWPE-AATRIKPKSA-N

> <FORMULA>
C13H20O2

> <MOLECULAR_WEIGHT>
208.2967

> <EXACT_MASS>
208.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.866725822263454

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.14

> <JCHEM_LOGP>
2.26648388

> <ALOGPS_LOGS>
-2.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.91142445950752

> <JCHEM_PKA_STRONGEST_BASIC>
-1.9621191530641804

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
63.707100000000004

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.10e-01 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0303805
     RDKit          3D
3-Oxo-alpha-ionol
 35 35  0  0  0  0  0  0  0  0999 V2000
   -0.0438    1.1743    2.6469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6836    0.9749    1.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3069    1.9893    0.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9147    1.7273   -0.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8392    2.6223   -1.4761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5713    0.4178   -0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6381   -0.6720   -0.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0064   -1.2570   -1.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5481   -1.8136    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184   -0.3277    0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7839   -0.6149    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7825    0.2351    0.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1639   -0.0283   -0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4394    0.6320   -1.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4560   -1.3704   -0.2966 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5191    2.0994    2.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6356    0.3192    2.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858    1.1554    3.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3276    2.9476    1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8881    0.2348   -1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4591    0.4015   -0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1308   -0.6357   -1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7270   -1.2179   -2.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7207   -2.3138   -1.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5508   -1.7487   -0.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1218   -2.7934   -0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6532   -1.6754    1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7118   -1.0946    1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9505   -1.5497   -0.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5916    1.1627    0.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8623    0.4101    0.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8406    1.6733   -1.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5351    0.6685   -2.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1995    0.0540   -2.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4872   -1.7860    0.6059 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
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 10  2  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  6 20  1  0
  6 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  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      -3.314   0.092   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.342  -1.447   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.021  -2.241   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.673  -1.494   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.645  -2.286   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      -4.687  -2.194   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      -0.645   0.046   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.699   0.790   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.018  -0.003   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.366   0.747   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.394   2.286   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       4.687  -0.046   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.937   2.035   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.967   0.839   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -0.956   2.001   0.000  0.00  0.00           C+0
CONECT    1    2   14                                                       
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5    7                                                  
CONECT    5    4                                                            
CONECT    6    2                                                            
CONECT    7    4    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11   12                                                  
CONECT   11   10                                                            
CONECT   12   10                                                            
CONECT   13   14                                                            
CONECT   14    1    7   13   15                                             
CONECT   15   14                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0303805
HETATM    1  C1  UNL     1      -0.044   1.174   2.647  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.684   0.975   1.317  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.307   1.989   0.699  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.915   1.727  -0.599  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.839   2.622  -1.476  1.00  0.00           O  
HETATM    6  C5  UNL     1      -2.571   0.418  -0.764  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.638  -0.672  -0.343  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.006  -1.257  -1.619  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.548  -1.814   0.160  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.618  -0.328   0.670  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.784  -0.615   0.158  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.783   0.235   0.301  1.00  0.00           C  
HETATM   13  C12 UNL     1       3.164  -0.028  -0.193  1.00  0.00           C  
HETATM   14  C13 UNL     1       3.439   0.632  -1.506  1.00  0.00           C  
HETATM   15  O2  UNL     1       3.456  -1.370  -0.297  1.00  0.00           O  
HETATM   16  H1  UNL     1       0.519   2.099   2.725  1.00  0.00           H  
HETATM   17  H2  UNL     1       0.636   0.319   2.821  1.00  0.00           H  
HETATM   18  H3  UNL     1      -0.786   1.155   3.469  1.00  0.00           H  
HETATM   19  H4  UNL     1      -1.328   2.948   1.175  1.00  0.00           H  
HETATM   20  H5  UNL     1      -2.888   0.235  -1.817  1.00  0.00           H  
HETATM   21  H6  UNL     1      -3.459   0.401  -0.080  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.131  -0.636  -1.903  1.00  0.00           H  
HETATM   23  H8  UNL     1      -1.727  -1.218  -2.461  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.721  -2.314  -1.451  1.00  0.00           H  
HETATM   25  H10 UNL     1      -3.551  -1.749  -0.311  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.122  -2.793  -0.110  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.653  -1.675   1.260  1.00  0.00           H  
HETATM   28  H13 UNL     1      -0.712  -1.095   1.506  1.00  0.00           H  
HETATM   29  H14 UNL     1       0.951  -1.550  -0.335  1.00  0.00           H  
HETATM   30  H15 UNL     1       1.592   1.163   0.796  1.00  0.00           H  
HETATM   31  H16 UNL     1       3.862   0.410   0.558  1.00  0.00           H  
HETATM   32  H17 UNL     1       3.841   1.673  -1.360  1.00  0.00           H  
HETATM   33  H18 UNL     1       2.535   0.668  -2.166  1.00  0.00           H  
HETATM   34  H19 UNL     1       4.199   0.054  -2.073  1.00  0.00           H  
HETATM   35  H20 UNL     1       3.487  -1.786   0.606  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3   10
CONECT    3    4   19
CONECT    4    5    5    6
CONECT    6    7   20   21
CONECT    7    8    9   10
CONECT    8   22   23   24
CONECT    9   25   26   27
CONECT   10   11   28
CONECT   11   12   12   29
CONECT   12   13   30
CONECT   13   14   15   31
CONECT   14   32   33   34
CONECT   15   35
END

HMDB0303805
     RDKit          3D
3-Oxo-alpha-ionol
 35 35  0  0  0  0  0  0  0  0999 V2000
   -0.0438    1.1743    2.6469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6836    0.9749    1.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3069    1.9893    0.6988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9147    1.7273   -0.5994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8392    2.6223   -1.4761 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5713    0.4178   -0.7645 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6381   -0.6720   -0.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0064   -1.2570   -1.6189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5481   -1.8136    0.1598 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6184   -0.3277    0.6697 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7839   -0.6149    0.1583 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7825    0.2351    0.3008 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1639   -0.0283   -0.1934 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4394    0.6320   -1.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4560   -1.3704   -0.2966 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.5191    2.0994    2.7254 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6356    0.3192    2.8209 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7858    1.1554    3.4686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3276    2.9476    1.1751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8881    0.2348   -1.8174 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4591    0.4015   -0.0803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1308   -0.6357   -1.9031 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7270   -1.2179   -2.4612 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7207   -2.3138   -1.4514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5508   -1.7487   -0.3115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1218   -2.7934   -0.1104 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6532   -1.6754    1.2596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7118   -1.0946    1.5056 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9505   -1.5497   -0.3351 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5916    1.1627    0.7956 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8623    0.4101    0.5585 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8406    1.6733   -1.3602 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5351    0.6685   -2.1657 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1995    0.0540   -2.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4872   -1.7860    0.6059 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
 11 12  2  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 10  2  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  6 20  1  0
  6 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
  9 26  1  0
  9 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-oxo-a-Ionol	Generator
3-oxo-Α-ionol	Generator

Chemical Formula

C₁₃H₂₀O₂

Average Molecular Weight

208.2967

Monoisotopic Molecular Weight

208.146329884

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

CC(O)\C=C\C1C(C)=CC(=O)CC1(C)C

InChI Identifier

InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-7,10,12,14H,8H2,1-4H3/b6-5+

InChI Key

MDCGEAGEQVMWPE-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

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

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Exogenous (HMDB: HMDB0303805)

Not Available

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	2.14	ALOGPS
logP	2.27	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	16.91	ChemAxon
pKa (Strongest Basic)	-2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.71 m³·mol⁻¹	ChemAxon
Polarizability	23.87 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
AllCCS	[M+H]+	148.602	32859911
AllCCS	[M+H-H2O]+	144.69	32859911
AllCCS	[M+Na]+	153.289	32859911
AllCCS	[M+NH4]+	152.241	32859911
AllCCS	[M-H]-	153.4	32859911
AllCCS	[M+Na-2H]-	154.264	32859911
AllCCS	[M+HCOO]-	155.311	32859911
DeepCCS	[M+H]+	154.181	30932474
DeepCCS	[M-H]-	151.786	30932474
DeepCCS	[M-2H]-	184.922	30932474
DeepCCS	[M+Na]+	160.094	30932474

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Predicted by Siyang on May 30, 2022	11.7925 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.38 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2056.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	290.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	143.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	164.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	85.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	407.0 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	405.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	62.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	953.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	381.5 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	1097.1 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	319.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	313.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	263.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	295.1 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	7.8 seconds	40023050

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Oxo-alpha-ionol,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)(C)C1/C=C/C(C)O[Si](C)(C)C	1789.3	Semi standard non polar	33892256
3-Oxo-alpha-ionol,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)(C)C1/C=C/C(C)O[Si](C)(C)C	1788.6	Standard non polar	33892256
3-Oxo-alpha-ionol,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)(C)C1/C=C/C(C)O[Si](C)(C)C	1978.4	Standard polar	33892256
3-Oxo-alpha-ionol,2TBDMS,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	2240.7	Semi standard non polar	33892256
3-Oxo-alpha-ionol,2TBDMS,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	2255.6	Standard non polar	33892256
3-Oxo-alpha-ionol,2TBDMS,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	2210.3	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Oxo-alpha-ionol GC-MS (Non-derivatized) - 70eV, Positive	splash10-014l-6900000000-175ed8e8e900e68622a8	2016-09-22	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 - 3-Oxo-alpha-ionol 10V, Positive-QTOF	splash10-0006-0920000000-e28db426c476498cb016	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-ionol 20V, Positive-QTOF	splash10-0006-2910000000-f6f0342c3271b58e2297	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-ionol 40V, Positive-QTOF	splash10-05fr-5900000000-d9246d5b91f9921a98ad	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-ionol 10V, Negative-QTOF	splash10-0a4i-0390000000-2bb483ac3840a1da1c87	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-ionol 20V, Negative-QTOF	splash10-0a4r-1980000000-49bfac00968f2c20a928	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-ionol 40V, Negative-QTOF	splash10-05g3-3900000000-2dc31331233702d75f51	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-ionol 10V, Positive-QTOF	splash10-05bf-0920000000-8d8e372877b113a5e4e3	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-ionol 20V, Positive-QTOF	splash10-001i-4900000000-9239880d66792714b68a	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-ionol 40V, Positive-QTOF	splash10-002b-6900000000-47292d29c4724121a75b	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-ionol 10V, Negative-QTOF	splash10-0a4i-0090000000-43a9bdbf7663e467c30d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-ionol 20V, Negative-QTOF	splash10-000i-0910000000-4d272d0d821e030fd7ba	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Oxo-alpha-ionol 40V, Negative-QTOF	splash10-01p2-1900000000-cca33764e7d01a23d9d8	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

FDB021721

KNApSAcK ID

C00029328

Chemspider ID

4520951

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5370052

PDB ID

Not Available

ChEBI ID

Not Available

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 3-Oxo-alpha-ionol (HMDB0303805)

MOL for HMDB0303805 (3-Oxo-alpha-ionol)

3D MOL for HMDB0303805 (3-Oxo-alpha-ionol)

3D SDF for HMDB0303805 (3-Oxo-alpha-ionol)

3D-SDF for HMDB0303805 (3-Oxo-alpha-ionol)

PDB for HMDB0303805 (3-Oxo-alpha-ionol)

3D PDB for HMDB0303805 (3-Oxo-alpha-ionol)

SMILES for HMDB0303805 (3-Oxo-alpha-ionol)

INCHI for HMDB0303805 (3-Oxo-alpha-ionol)

Structure for HMDB0303805 (3-Oxo-alpha-ionol)

3D Structure for HMDB0303805 (3-Oxo-alpha-ionol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra