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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-24 01:56:11 UTC

Update Date

2021-09-24 01:56:11 UTC

HMDB ID

HMDB0303443

Secondary Accession Numbers

None

Metabolite Identification

Common Name

3,5-Dihydroxy-6,7-megastigmadien-9-one

Description

3,5-dihydroxy-6,7-megastigmadien-9-one is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. 3,5-dihydroxy-6,7-megastigmadien-9-one is slightly soluble (in water) and a very weakly acidic compound (based on its pKa). 3,5-dihydroxy-6,7-megastigmadien-9-one can be found in common grape, which makes 3,5-dihydroxy-6,7-megastigmadien-9-one a potential biomarker for the consumption of this food product.

Structure

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

HMDB0303443
     RDKit          3D
3,5-Dihydroxy-6,7-megastigmadien-9-one
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.2510    0.0548   -1.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071   -0.7540   -0.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8416   -1.8131   -1.2831 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6254   -0.4021    0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3352   -0.1608    0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0396    0.0581    0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7879   -1.1149    0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8986   -1.9324   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2612   -2.0724    1.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1653   -0.6897    0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6298    0.4911    0.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9080    0.8275    0.6372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7474    1.6885    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058    1.4267    0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0943    1.7943   -1.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4451    2.3756    0.7762 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7826    0.6590   -2.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8408    0.6625   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9815   -0.6156   -1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0243   -0.2927    1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0931   -1.8874   -1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6739   -1.5268   -1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2139   -2.9697   -0.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1181   -2.5847    2.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4282   -2.8086    1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3314   -1.4769    2.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9120   -1.5093    0.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0885   -0.3813    2.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7274    0.2445   -0.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8737    1.2700    1.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7941    1.9235    1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1058    2.5509   -0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262    0.8963   -2.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9397    2.4440   -1.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8521    2.3614   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1926    3.2636    0.3735 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  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
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
 16 36  1  0
M  END

  Mrv0541 02241214382D          

 16 16  0  0  0  0            999 V2000
   -1.0726   -0.9591    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5012   -0.9591    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0726    0.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6020    1.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5419    1.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4550   -0.4036    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.0711    1.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3574    0.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3576    0.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3576   -0.5465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0758   -1.3220    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.6910    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5012    1.1034    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862   -0.1341    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 12  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  5 11  1  0  0  0  0
  8 12  1  0  0  0  0
  9 10  2  0  0  0  0
  9 14  1  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
 14 15  1  0  0  0  0
 14 16  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0303443

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
QMXLZUOHZGYGDY-UHFFFAOYSA-N

> <FORMULA>
C13H20O3

> <MOLECULAR_WEIGHT>
224.2961

> <EXACT_MASS>
224.141244506

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_AVERAGE_POLARIZABILITY>
24.657716497461777

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)but-3-en-2-one

> <ALOGPS_LOGP>
1.55

> <JCHEM_LOGP>
0.7767904559999997

> <ALOGPS_LOGS>
-2.30

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
15.263725075318526

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.007504388621555

> <JCHEM_PKA_STRONGEST_BASIC>
-2.743137723333313

> <JCHEM_POLAR_SURFACE_AREA>
57.53

> <JCHEM_REFRACTIVITY>
63.883799999999994

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.13e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)but-3-en-2-one

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0303443
     RDKit          3D
3,5-Dihydroxy-6,7-megastigmadien-9-one
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.2510    0.0548   -1.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071   -0.7540   -0.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8416   -1.8131   -1.2831 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6254   -0.4021    0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3352   -0.1608    0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0396    0.0581    0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7879   -1.1149    0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8986   -1.9324   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2612   -2.0724    1.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1653   -0.6897    0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6298    0.4911    0.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9080    0.8275    0.6372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7474    1.6885    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058    1.4267    0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0943    1.7943   -1.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4451    2.3756    0.7762 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7826    0.6590   -2.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8408    0.6625   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9815   -0.6156   -1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0243   -0.2927    1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0931   -1.8874   -1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6739   -1.5268   -1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2139   -2.9697   -0.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1181   -2.5847    2.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4282   -2.8086    1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3314   -1.4769    2.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9120   -1.5093    0.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0885   -0.3813    2.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7274    0.2445   -0.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8737    1.2700    1.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7941    1.9235    1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1058    2.5509   -0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262    0.8963   -2.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9397    2.4440   -1.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8521    2.3614   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1926    3.2636    0.3735 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  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
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 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      -2.002  -1.790   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.334  -1.020   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -4.669  -1.790   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      -3.334   0.520   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.002   1.290   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.990   2.468   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.012   2.468   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0       0.849  -0.753   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0       1.999   2.060   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.667   1.290   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.668   0.520   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.668  -1.020   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.141  -2.468   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.334   1.290   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       4.669   2.060   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       3.334  -0.250   0.000  0.00  0.00           O+0
CONECT    1    2   12                                                       
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6    7   11                                             
CONECT    6    5                                                            
CONECT    7    5                                                            
CONECT    8   12                                                            
CONECT    9   10   14                                                       
CONECT   10    9   11                                                       
CONECT   11    5   10   12                                                  
CONECT   12    1    8   11   13                                             
CONECT   13   12                                                            
CONECT   14    9   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0303443
HETATM    1  C1  UNL     1       4.251   0.055  -1.421  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.207  -0.754  -0.710  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.842  -1.813  -1.283  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.625  -0.402   0.537  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.335  -0.161   0.502  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.040   0.058   0.357  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.788  -1.115   0.529  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.899  -1.932  -0.754  1.00  0.00           C  
HETATM    9  C8  UNL     1      -0.261  -2.072   1.593  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.165  -0.690   0.989  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.630   0.491   0.184  1.00  0.00           C  
HETATM   12  O2  UNL     1      -3.908   0.827   0.637  1.00  0.00           O  
HETATM   13  C11 UNL     1      -1.747   1.689   0.432  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.306   1.427   0.051  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.094   1.794  -1.416  1.00  0.00           C  
HETATM   16  O3  UNL     1       0.445   2.376   0.776  1.00  0.00           O  
HETATM   17  H1  UNL     1       3.783   0.659  -2.209  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.841   0.663  -0.700  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.981  -0.616  -1.929  1.00  0.00           H  
HETATM   20  H4  UNL     1       3.024  -0.293   1.503  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.093  -1.887  -1.234  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.674  -1.527  -1.428  1.00  0.00           H  
HETATM   23  H7  UNL     1      -1.214  -2.970  -0.500  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.118  -2.585   2.095  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.428  -2.809   1.141  1.00  0.00           H  
HETATM   26  H10 UNL     1       0.331  -1.477   2.316  1.00  0.00           H  
HETATM   27  H11 UNL     1      -2.912  -1.509   0.845  1.00  0.00           H  
HETATM   28  H12 UNL     1      -2.088  -0.381   2.052  1.00  0.00           H  
HETATM   29  H13 UNL     1      -2.727   0.245  -0.884  1.00  0.00           H  
HETATM   30  H14 UNL     1      -3.874   1.270   1.525  1.00  0.00           H  
HETATM   31  H15 UNL     1      -1.794   1.923   1.517  1.00  0.00           H  
HETATM   32  H16 UNL     1      -2.106   2.551  -0.141  1.00  0.00           H  
HETATM   33  H17 UNL     1      -0.026   0.896  -2.056  1.00  0.00           H  
HETATM   34  H18 UNL     1      -0.940   2.444  -1.726  1.00  0.00           H  
HETATM   35  H19 UNL     1       0.852   2.361  -1.562  1.00  0.00           H  
HETATM   36  H20 UNL     1       0.193   3.264   0.374  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    3    4
CONECT    4    5    5   20
CONECT    5    6    6
CONECT    6    7   14
CONECT    7    8    9   10
CONECT    8   21   22   23
CONECT    9   24   25   26
CONECT   10   11   27   28
CONECT   11   12   13   29
CONECT   12   30
CONECT   13   14   31   32
CONECT   14   15   16
CONECT   15   33   34   35
CONECT   16   36
END

HMDB0303443
     RDKit          3D
3,5-Dihydroxy-6,7-megastigmadien-9-one
 36 36  0  0  0  0  0  0  0  0999 V2000
    4.2510    0.0548   -1.4213 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2071   -0.7540   -0.7101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8416   -1.8131   -1.2831 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6254   -0.4021    0.5365 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3352   -0.1608    0.5016 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0396    0.0581    0.3567 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7879   -1.1149    0.5287 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8986   -1.9324   -0.7537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2612   -2.0724    1.5925 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1653   -0.6897    0.9895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6298    0.4911    0.1839 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9080    0.8275    0.6372 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7474    1.6885    0.4323 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3058    1.4267    0.0514 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0943    1.7943   -1.4156 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4451    2.3756    0.7762 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7826    0.6590   -2.2094 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8408    0.6625   -0.7003 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.9815   -0.6156   -1.9287 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0243   -0.2927    1.5026 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0931   -1.8874   -1.2341 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6739   -1.5268   -1.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2139   -2.9697   -0.5001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1181   -2.5847    2.0953 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4282   -2.8086    1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3314   -1.4769    2.3160 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9120   -1.5093    0.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0885   -0.3813    2.0524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7274    0.2445   -0.8845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8737    1.2700    1.5253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7941    1.9235    1.5169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1058    2.5509   -0.1410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0262    0.8963   -2.0560 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9397    2.4440   -1.7262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8521    2.3614   -1.5622 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1926    3.2636    0.3735 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  2  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  7 10  1  0
 10 11  1  0
 11 12  1  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
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
  9 26  1  0
 10 27  1  0
 10 28  1  0
 11 29  1  0
 12 30  1  0
 13 31  1  0
 13 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

Not Available

Chemical Formula

C₁₃H₂₀O₃

Average Molecular Weight

224.2961

Monoisotopic Molecular Weight

224.141244506

IUPAC Name

4-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)but-3-en-2-one

Traditional Name

4-(2,4-dihydroxy-2,6,6-trimethylcyclohexylidene)but-3-en-2-one

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

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

InChI Key

QMXLZUOHZGYGDY-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
Tertiary alcohol
Enone
Cyclic alcohol
Acryloyl-group
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

a 9-apo-carotenone (CPD-7201 )

Ontology

Not Available

Exogenous (HMDB: HMDB0303443)

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	1.55	ALOGPS
logP	0.78	ChemAxon
logS	-2.3	ALOGPS
pKa (Strongest Acidic)	14.01	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	1	ChemAxon
Refractivity	63.88 m³·mol⁻¹	ChemAxon
Polarizability	24.66 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]+	152.601	32859911
AllCCS	[M+H-H2O]+	148.855	32859911
AllCCS	[M+Na]+	157.086	32859911
AllCCS	[M+NH4]+	156.084	32859911
AllCCS	[M-H]-	156.402	32859911
AllCCS	[M+Na-2H]-	157.187	32859911
AllCCS	[M+HCOO]-	158.152	32859911
DeepCCS	[M+H]+	159.855	30932474
DeepCCS	[M-H]-	157.497	30932474
DeepCCS	[M-2H]-	190.729	30932474
DeepCCS	[M+Na]+	165.949	30932474

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3,5-Dihydroxy-6,7-megastigmadien-9-one,3TMS,isomer #1	C=C(C=C=C1C(C)(C)CC(O[Si](C)(C)C)CC1(C)O[Si](C)(C)C)O[Si](C)(C)C	1937.5	Semi standard non polar	33892256
3,5-Dihydroxy-6,7-megastigmadien-9-one,3TMS,isomer #1	C=C(C=C=C1C(C)(C)CC(O[Si](C)(C)C)CC1(C)O[Si](C)(C)C)O[Si](C)(C)C	1992.4	Standard non polar	33892256
3,5-Dihydroxy-6,7-megastigmadien-9-one,3TMS,isomer #1	C=C(C=C=C1C(C)(C)CC(O[Si](C)(C)C)CC1(C)O[Si](C)(C)C)O[Si](C)(C)C	2035.1	Standard polar	33892256
3,5-Dihydroxy-6,7-megastigmadien-9-one,3TBDMS,isomer #1	C=C(C=C=C1C(C)(C)CC(O[Si](C)(C)C(C)(C)C)CC1(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2576.7	Semi standard non polar	33892256
3,5-Dihydroxy-6,7-megastigmadien-9-one,3TBDMS,isomer #1	C=C(C=C=C1C(C)(C)CC(O[Si](C)(C)C(C)(C)C)CC1(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2642.0	Standard non polar	33892256
3,5-Dihydroxy-6,7-megastigmadien-9-one,3TBDMS,isomer #1	C=C(C=C=C1C(C)(C)CC(O[Si](C)(C)C(C)(C)C)CC1(C)O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2354.3	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 - 3,5-Dihydroxy-6,7-megastigmadien-9-one 10V, Positive-QTOF	splash10-0a4r-0690000000-dda81bfe8d29cc5c1798	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-megastigmadien-9-one 20V, Positive-QTOF	splash10-052r-2950000000-ac5e6503dfcea85e193e	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-megastigmadien-9-one 40V, Positive-QTOF	splash10-00kr-6900000000-e061bd15cf375cd6108c	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-megastigmadien-9-one 10V, Negative-QTOF	splash10-05fr-0290000000-74e212913d7f58a8d272	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-megastigmadien-9-one 20V, Negative-QTOF	splash10-0ab9-1390000000-a81267d4e99e45a8437c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-megastigmadien-9-one 40V, Negative-QTOF	splash10-0a4i-5920000000-2e8c8a8cccc6a1d6ea38	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-megastigmadien-9-one 10V, Positive-QTOF	splash10-05r0-0970000000-012ce98499b8ce2fbcee	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-megastigmadien-9-one 20V, Positive-QTOF	splash10-0540-8910000000-293b78e5cfd6b511e5e0	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-megastigmadien-9-one 40V, Positive-QTOF	splash10-00ec-9600000000-80b51699173b46cdae11	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-megastigmadien-9-one 10V, Negative-QTOF	splash10-00di-0190000000-5155d9dec1b13cc21d24	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-megastigmadien-9-one 20V, Negative-QTOF	splash10-0a4i-1920000000-c358e54804d58e8277c1	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3,5-Dihydroxy-6,7-megastigmadien-9-one 40V, Negative-QTOF	splash10-0bt9-1910000000-394d7d5eb093c8aca429	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

FDB013523

KNApSAcK ID

Not Available

Chemspider ID

8395638

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10220146

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 3,5-Dihydroxy-6,7-megastigmadien-9-one (HMDB0303443)

MOL for HMDB0303443 (3,5-Dihydroxy-6,7-megastigmadien-9-one)

3D MOL for HMDB0303443 (3,5-Dihydroxy-6,7-megastigmadien-9-one)

3D SDF for HMDB0303443 (3,5-Dihydroxy-6,7-megastigmadien-9-one)

3D-SDF for HMDB0303443 (3,5-Dihydroxy-6,7-megastigmadien-9-one)

PDB for HMDB0303443 (3,5-Dihydroxy-6,7-megastigmadien-9-one)

3D PDB for HMDB0303443 (3,5-Dihydroxy-6,7-megastigmadien-9-one)

SMILES for HMDB0303443 (3,5-Dihydroxy-6,7-megastigmadien-9-one)

INCHI for HMDB0303443 (3,5-Dihydroxy-6,7-megastigmadien-9-one)

Structure for HMDB0303443 (3,5-Dihydroxy-6,7-megastigmadien-9-one)

3D Structure for HMDB0303443 (3,5-Dihydroxy-6,7-megastigmadien-9-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

MS/MS Spectra