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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 22:56:21 UTC

Update Date

2021-09-23 22:56:21 UTC

HMDB ID

HMDB0303053

Secondary Accession Numbers

None

Metabolite Identification

Common Name

9-Hydroxymegastigma-4,6,7-trien-3-one

Description

9-hydroxymegastigma-4,6,7-trien-3-one is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. 9-hydroxymegastigma-4,6,7-trien-3-one is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). 9-hydroxymegastigma-4,6,7-trien-3-one can be found in common grape, which makes 9-hydroxymegastigma-4,6,7-trien-3-one a potential biomarker for the consumption of this food product.

Structure

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

HMDB0303053
     RDKit          3D
9-Hydroxymegastigma-4,6,7-trien-3-one
 33 33  0  0  0  0  0  0  0  0999 V2000
    0.0685    2.8373    0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505    1.6031    0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7461    1.5774    1.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5113    0.3445    1.7098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0524    0.0154    2.7922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6499   -0.5211    0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726   -0.7904   -0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5618   -1.0560   -1.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6578   -2.0154    0.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5153    0.4299   -0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5614    0.4605   -0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6730    0.4778   -1.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8383   -0.0151   -0.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5758   -0.9464    0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7571   -0.5887   -1.6577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3417    3.4309   -0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1311    3.4028    1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0840    2.5102    0.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9801    2.4449    2.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1043   -1.4983    0.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3142    0.0025   -0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1139   -1.9971   -1.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145   -0.1647   -1.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554   -1.0597   -2.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4640   -2.8064    0.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0834   -2.4176   -0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1792   -1.8906    1.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650    0.8510   -2.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3821    0.8800   -0.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5188   -0.9997    0.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7977   -0.5899    1.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4276   -1.9822   -0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4212    0.0710   -1.9719 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  2  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
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
M  END

  Mrv0541 02241212582D          

 15 15  0  0  0  0            999 V2000
   -3.7714    0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4859   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4859   -1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7714   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0570   -1.0902    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0570   -0.2652    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3548    0.7307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3589    0.8618    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3425   -1.5027    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3425    0.1473    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6280    0.5598    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6280    1.3849    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9136    1.7973    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2004   -1.5027    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3425    1.7974    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  7  1  0  0  0  0
  1  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  2  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
  3 14  2  0  0  0  0
 12 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303053

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C13H18O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5,7,10,14H,8H2,1-4H3

> <INCHI_KEY>
ZYHHDRRWYJNBAN-UHFFFAOYSA-N

> <FORMULA>
C13H18O2

> <MOLECULAR_WEIGHT>
206.2808

> <EXACT_MASS>
206.13067982

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
23.487360917186265

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(3-hydroxybut-1-en-1-ylidene)-3,5,5-trimethylcyclohex-2-en-1-one

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.0151793876666675

> <ALOGPS_LOGS>
-2.61

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.247715793776482

> <JCHEM_PKA_STRONGEST_BASIC>
-2.2530491118021665

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
63.121199999999995

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.08e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(3-hydroxybut-1-en-1-ylidene)-3,5,5-trimethylcyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0303053
     RDKit          3D
9-Hydroxymegastigma-4,6,7-trien-3-one
 33 33  0  0  0  0  0  0  0  0999 V2000
    0.0685    2.8373    0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505    1.6031    0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7461    1.5774    1.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5113    0.3445    1.7098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0524    0.0154    2.7922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6499   -0.5211    0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726   -0.7904   -0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5618   -1.0560   -1.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6578   -2.0154    0.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5153    0.4299   -0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5614    0.4605   -0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6730    0.4778   -1.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8383   -0.0151   -0.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5758   -0.9464    0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7571   -0.5887   -1.6577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3417    3.4309   -0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1311    3.4028    1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0840    2.5102    0.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9801    2.4449    2.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1043   -1.4983    0.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3142    0.0025   -0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1139   -1.9971   -1.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145   -0.1647   -1.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554   -1.0597   -2.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4640   -2.8064    0.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0834   -2.4176   -0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1792   -1.8906    1.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650    0.8510   -2.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3821    0.8800   -0.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5188   -0.9997    0.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7977   -0.5899    1.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4276   -1.9822   -0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4212    0.0710   -1.9719 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  2  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
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  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      -7.040   0.275   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.374  -0.495   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.374  -2.035   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -7.040  -2.805   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -5.706  -2.035   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.706  -0.495   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -8.129   1.364   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.270   1.609   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.373  -2.805   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.373   0.275   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.039   1.045   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.039   2.585   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.705   3.355   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -9.707  -2.805   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0      -4.373   3.355   0.000  0.00  0.00           O+0
CONECT    1    2    6    7    8                                             
CONECT    2    1    3                                                       
CONECT    3    2    4   14                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6    9                                                  
CONECT    6    1    5   10                                                  
CONECT    7    1                                                            
CONECT    8    1                                                            
CONECT    9    5                                                            
CONECT   10    6   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   15                                                  
CONECT   13   12                                                            
CONECT   14    3                                                            
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0303053
HETATM    1  C1  UNL     1       0.068   2.837   0.620  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.750   1.603   0.751  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.746   1.577   1.626  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.511   0.345   1.710  1.00  0.00           C  
HETATM    5  O1  UNL     1      -3.052   0.015   2.792  1.00  0.00           O  
HETATM    6  C5  UNL     1      -2.650  -0.521   0.513  1.00  0.00           C  
HETATM    7  C6  UNL     1      -1.273  -0.790  -0.110  1.00  0.00           C  
HETATM    8  C7  UNL     1      -1.562  -1.056  -1.595  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.658  -2.015   0.449  1.00  0.00           C  
HETATM   10  C9  UNL     1      -0.515   0.430  -0.026  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.561   0.460  -0.786  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.673   0.478  -1.470  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.838  -0.015  -0.765  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.576  -0.946   0.353  1.00  0.00           C  
HETATM   15  O2  UNL     1       3.757  -0.589  -1.658  1.00  0.00           O  
HETATM   16  H1  UNL     1      -0.342   3.431  -0.226  1.00  0.00           H  
HETATM   17  H2  UNL     1       0.131   3.403   1.561  1.00  0.00           H  
HETATM   18  H3  UNL     1       1.084   2.510   0.309  1.00  0.00           H  
HETATM   19  H4  UNL     1      -1.980   2.445   2.256  1.00  0.00           H  
HETATM   20  H5  UNL     1      -3.104  -1.498   0.783  1.00  0.00           H  
HETATM   21  H6  UNL     1      -3.314   0.002  -0.206  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.114  -1.997  -1.737  1.00  0.00           H  
HETATM   23  H8  UNL     1      -2.115  -0.165  -1.954  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.555  -1.060  -2.085  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.464  -2.806   0.495  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.083  -2.418  -0.273  1.00  0.00           H  
HETATM   27  H12 UNL     1      -0.179  -1.891   1.428  1.00  0.00           H  
HETATM   28  H13 UNL     1       1.565   0.851  -2.445  1.00  0.00           H  
HETATM   29  H14 UNL     1       3.382   0.880  -0.339  1.00  0.00           H  
HETATM   30  H15 UNL     1       3.519  -1.000   0.977  1.00  0.00           H  
HETATM   31  H16 UNL     1       1.798  -0.590   1.036  1.00  0.00           H  
HETATM   32  H17 UNL     1       2.428  -1.982  -0.013  1.00  0.00           H  
HETATM   33  H18 UNL     1       4.421   0.071  -1.972  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   11
CONECT   11   12   12
CONECT   12   13   28
CONECT   13   14   15   29
CONECT   14   30   31   32
CONECT   15   33
END

HMDB0303053
     RDKit          3D
9-Hydroxymegastigma-4,6,7-trien-3-one
 33 33  0  0  0  0  0  0  0  0999 V2000
    0.0685    2.8373    0.6201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7505    1.6031    0.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7461    1.5774    1.6259 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5113    0.3445    1.7098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0524    0.0154    2.7922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6499   -0.5211    0.5134 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2726   -0.7904   -0.1100 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5618   -1.0560   -1.5948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6578   -2.0154    0.4487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5153    0.4299   -0.0260 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5614    0.4605   -0.7856 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6730    0.4778   -1.4701 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8383   -0.0151   -0.7654 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5758   -0.9464    0.3532 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7571   -0.5887   -1.6577 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3417    3.4309   -0.2255 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1311    3.4028    1.5607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0840    2.5102    0.3086 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9801    2.4449    2.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1043   -1.4983    0.7831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3142    0.0025   -0.2064 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1139   -1.9971   -1.7367 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1145   -0.1647   -1.9535 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554   -1.0597   -2.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4640   -2.8064    0.4948 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0834   -2.4176   -0.2728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1792   -1.8906    1.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5650    0.8510   -2.4454 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3821    0.8800   -0.3390 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5188   -0.9997    0.9767 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7977   -0.5899    1.0360 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4276   -1.9822   -0.0126 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4212    0.0710   -1.9719 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  2  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
 12 28  1  0
 13 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₁₈O₂

Average Molecular Weight

206.2808

Monoisotopic Molecular Weight

206.13067982

IUPAC Name

4-(3-hydroxybut-1-en-1-ylidene)-3,5,5-trimethylcyclohex-2-en-1-one

Traditional Name

4-(3-hydroxybut-1-en-1-ylidene)-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/C13H18O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5,7,10,14H,8H2,1-4H3

InChI Key

ZYHHDRRWYJNBAN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Megastigmane sesquiterpenoid
Sesquiterpenoid
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

Not Available

Exogenous (HMDB: HMDB0303053)

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	2.17	ALOGPS
logP	2.02	ChemAxon
logS	-2.6	ALOGPS
pKa (Strongest Acidic)	16.25	ChemAxon
pKa (Strongest Basic)	-2.3	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	1	ChemAxon
Refractivity	63.12 m³·mol⁻¹	ChemAxon
Polarizability	23.49 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]+	147.48	32859911
AllCCS	[M+H-H2O]+	143.524	32859911
AllCCS	[M+Na]+	152.222	32859911
AllCCS	[M+NH4]+	151.162	32859911
AllCCS	[M-H]-	152.009	32859911
AllCCS	[M+Na-2H]-	152.789	32859911
AllCCS	[M+HCOO]-	153.743	32859911
DeepCCS	[M+H]+	155.38	30932474
DeepCCS	[M-H]-	152.989	30932474
DeepCCS	[M-2H]-	186.153	30932474
DeepCCS	[M+Na]+	161.44	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
9-Hydroxymegastigma-4,6,7-trien-3-one,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)(C)C1=C=CC(C)O[Si](C)(C)C	1869.5	Semi standard non polar	33892256
9-Hydroxymegastigma-4,6,7-trien-3-one,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)(C)C1=C=CC(C)O[Si](C)(C)C	1899.2	Standard non polar	33892256
9-Hydroxymegastigma-4,6,7-trien-3-one,2TMS,isomer #1	CC1=CC(O[Si](C)(C)C)=CC(C)(C)C1=C=CC(C)O[Si](C)(C)C	2020.7	Standard polar	33892256
9-Hydroxymegastigma-4,6,7-trien-3-one,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C1=C=CC(C)O[Si](C)(C)C(C)(C)C	2315.0	Semi standard non polar	33892256
9-Hydroxymegastigma-4,6,7-trien-3-one,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C1=C=CC(C)O[Si](C)(C)C(C)(C)C	2385.9	Standard non polar	33892256
9-Hydroxymegastigma-4,6,7-trien-3-one,2TBDMS,isomer #1	CC1=CC(O[Si](C)(C)C(C)(C)C)=CC(C)(C)C1=C=CC(C)O[Si](C)(C)C(C)(C)C	2255.2	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 - 9-Hydroxymegastigma-4,6,7-trien-3-one 10V, Positive-QTOF	splash10-000i-0920000000-ec39a1baa38759fc23bf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxymegastigma-4,6,7-trien-3-one 20V, Positive-QTOF	splash10-000i-3910000000-972e547e7bde9c4d24f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxymegastigma-4,6,7-trien-3-one 40V, Positive-QTOF	splash10-0aba-5900000000-febbe6d14b7dd9ef253e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxymegastigma-4,6,7-trien-3-one 10V, Negative-QTOF	splash10-0a4i-0590000000-9b92308b21d7c8b091a9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxymegastigma-4,6,7-trien-3-one 20V, Negative-QTOF	splash10-0a4r-1970000000-93a3fcf6919fb9b5bf98	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxymegastigma-4,6,7-trien-3-one 40V, Negative-QTOF	splash10-0079-2900000000-7acdb78c181b61ccd151	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxymegastigma-4,6,7-trien-3-one 10V, Positive-QTOF	splash10-000i-0920000000-797d3decee636a060d78	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxymegastigma-4,6,7-trien-3-one 20V, Positive-QTOF	splash10-007a-4900000000-a43a833fa59b11f1c23d	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxymegastigma-4,6,7-trien-3-one 40V, Positive-QTOF	splash10-0230-7900000000-3afe828fd2eb6e74c620	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxymegastigma-4,6,7-trien-3-one 10V, Negative-QTOF	splash10-0a4i-0190000000-9251ab2cb3c011b880e9	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxymegastigma-4,6,7-trien-3-one 20V, Negative-QTOF	splash10-01p9-0900000000-b7d8d30be42415488dbd	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 9-Hydroxymegastigma-4,6,7-trien-3-one 40V, Negative-QTOF	splash10-0002-1900000000-c5e3a09430bd546551c9	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

FDB007534

KNApSAcK ID

Not Available

Chemspider ID

57500936

KEGG Compound ID

Not Available

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

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 9-Hydroxymegastigma-4,6,7-trien-3-one (HMDB0303053)

MOL for HMDB0303053 (9-Hydroxymegastigma-4,6,7-trien-3-one)

3D MOL for HMDB0303053 (9-Hydroxymegastigma-4,6,7-trien-3-one)

3D SDF for HMDB0303053 (9-Hydroxymegastigma-4,6,7-trien-3-one)

3D-SDF for HMDB0303053 (9-Hydroxymegastigma-4,6,7-trien-3-one)

PDB for HMDB0303053 (9-Hydroxymegastigma-4,6,7-trien-3-one)

3D PDB for HMDB0303053 (9-Hydroxymegastigma-4,6,7-trien-3-one)

SMILES for HMDB0303053 (9-Hydroxymegastigma-4,6,7-trien-3-one)

INCHI for HMDB0303053 (9-Hydroxymegastigma-4,6,7-trien-3-one)

Structure for HMDB0303053 (9-Hydroxymegastigma-4,6,7-trien-3-one)

3D Structure for HMDB0303053 (9-Hydroxymegastigma-4,6,7-trien-3-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra