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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 03:19:48 UTC

Update Date

2023-02-21 17:28:54 UTC

HMDB ID

HMDB0041636

Secondary Accession Numbers

HMDB41636

Metabolite Identification

Common Name

(3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one

Description

(3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR' (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one has been detected, but not quantified in, a few different foods, such as blackberries (Rubus), common grapes (Vitis vinifera), and evergreen blackberries (Rubus laciniatus). This could make (3R,8E)-3-hydroxy-5,8-megastigmadien-7-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one.

Structure

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

HMDB0041636
     RDKit          3D
(3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.8468    1.3179    0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3364    1.0886    0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6861    0.2726   -0.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3732   -0.2187   -0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4675   -1.0930   -1.7532 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0400   -0.1694   -0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4711    0.4997    0.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4285    1.3529    1.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9227    0.4634    1.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8110    0.5468    0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9844   -0.1383    0.2618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1324    0.0291   -1.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0394   -0.9969   -0.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6559   -1.6697   -2.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5689   -2.0398    0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2535    1.6978    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2320    0.2800   -0.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0236    1.9269   -0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151    1.6460    0.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4740   -0.1838   -1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929    2.1867    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2210    0.7690    2.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1427    1.7926    2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0909    1.4123    1.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1594   -0.3321    1.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1197    1.6091   -0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5855    0.3617    0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652   -0.3818   -1.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5969    0.8725   -1.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6416   -2.1300   -2.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2601   -1.0860   -2.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0511   -2.5746   -1.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4393   -3.0411   -0.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9285   -2.0876    0.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6240   -1.9827    0.2928 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
M  END

  Mrv0541 02241223382D          

 15 15  0  0  0  0            999 V2000
   -1.6013    1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0707    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7855   -0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0721   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3573   -0.8247    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3573    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0706    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7854    0.4123    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5002    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5415    1.0445    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573   -1.2370    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5002   -1.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3573    1.2370    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  7  1  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  6 13  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 15  2  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041636

> <DATABASE_NAME>
hmdb

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

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

> <INCHI_KEY>
UPRXEFYRIACHQZ-AATRIKPKSA-N

> <FORMULA>
C13H20O2

> <MOLECULAR_WEIGHT>
208.2967

> <EXACT_MASS>
208.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
24.297641146734748

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E)-1-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-2-en-1-one

> <ALOGPS_LOGP>
2.48

> <JCHEM_LOGP>
2.6568066893333344

> <ALOGPS_LOGS>
-2.22

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.907051693762668

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0896806254919693

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
63.56929999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.25e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E)-1-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0041636
     RDKit          3D
(3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.8468    1.3179    0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3364    1.0886    0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6861    0.2726   -0.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3732   -0.2187   -0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4675   -1.0930   -1.7532 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0400   -0.1694   -0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4711    0.4997    0.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4285    1.3529    1.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9227    0.4634    1.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8110    0.5468    0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9844   -0.1383    0.2618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1324    0.0291   -1.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0394   -0.9969   -0.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6559   -1.6697   -2.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5689   -2.0398    0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2535    1.6978    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2320    0.2800   -0.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0236    1.9269   -0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151    1.6460    0.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4740   -0.1838   -1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929    2.1867    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2210    0.7690    2.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1427    1.7926    2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0909    1.4123    1.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1594   -0.3321    1.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1197    1.6091   -0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5855    0.3617    0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652   -0.3818   -1.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5969    0.8725   -1.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6416   -2.1300   -2.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2601   -1.0860   -2.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0511   -2.5746   -1.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4393   -3.0411   -0.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9285   -2.0876    0.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6240   -1.9827    0.2928 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 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      -2.989   1.950   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.999   0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.333   0.000   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -3.333  -1.539   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.001  -2.309   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.667  -1.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.667   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.998   0.000   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.333   0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.667   0.000   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -1.011   1.950   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.667  -2.309   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -4.667  -2.309   0.000  0.00  0.00           O+0
HETATM   15  O   UNK     0       0.667   2.309   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    7   12                                             
CONECT    3    2    4                                                       
CONECT    4    3    5   14                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    2    6    8                                                  
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    2                                                            
CONECT   13    6                                                            
CONECT   14    4                                                            
CONECT   15    8                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0041636
HETATM    1  C1  UNL     1       4.847   1.318   0.012  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.336   1.089   0.210  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.686   0.273  -0.530  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.373  -0.219  -0.693  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.468  -1.093  -1.753  1.00  0.00           O  
HETATM    6  C5  UNL     1       0.040  -0.169  -0.204  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.471   0.500   0.809  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.428   1.353   1.609  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.923   0.463   1.217  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.811   0.547   0.006  1.00  0.00           C  
HETATM   11  O2  UNL     1      -3.984  -0.138   0.262  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.132   0.029  -1.218  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.039  -0.997  -0.890  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.656  -1.670  -2.145  1.00  0.00           C  
HETATM   15  C13 UNL     1      -1.569  -2.040   0.052  1.00  0.00           C  
HETATM   16  H1  UNL     1       5.254   1.698   0.943  1.00  0.00           H  
HETATM   17  H2  UNL     1       5.232   0.280  -0.176  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.024   1.927  -0.871  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.915   1.646   0.967  1.00  0.00           H  
HETATM   20  H5  UNL     1       3.474  -0.184  -1.299  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.793   2.187   1.026  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.221   0.769   2.096  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.143   1.793   2.489  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.091   1.412   1.777  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.159  -0.332   1.929  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.120   1.609  -0.218  1.00  0.00           H  
HETATM   27  H12 UNL     1      -4.585   0.362   0.864  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.865  -0.382  -1.935  1.00  0.00           H  
HETATM   29  H14 UNL     1      -1.597   0.873  -1.702  1.00  0.00           H  
HETATM   30  H15 UNL     1      -1.642  -2.130  -2.542  1.00  0.00           H  
HETATM   31  H16 UNL     1      -0.260  -1.086  -2.964  1.00  0.00           H  
HETATM   32  H17 UNL     1      -0.051  -2.575  -1.969  1.00  0.00           H  
HETATM   33  H18 UNL     1      -1.439  -3.041  -0.448  1.00  0.00           H  
HETATM   34  H19 UNL     1      -0.929  -2.088   0.960  1.00  0.00           H  
HETATM   35  H20 UNL     1      -2.624  -1.983   0.293  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3   19
CONECT    3    4   20
CONECT    4    5    5    6
CONECT    6    7    7   13
CONECT    7    8    9
CONECT    8   21   22   23
CONECT    9   10   24   25
CONECT   10   11   12   26
CONECT   11   27
CONECT   12   13   28   29
CONECT   13   14   15
CONECT   14   30   31   32
CONECT   15   33   34   35
END

HMDB0041636
     RDKit          3D
(3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.8468    1.3179    0.0115 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3364    1.0886    0.2095 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6861    0.2726   -0.5303 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3732   -0.2187   -0.6928 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4675   -1.0930   -1.7532 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0400   -0.1694   -0.2038 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4711    0.4997    0.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4285    1.3529    1.6086 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9227    0.4634    1.2171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8110    0.5468    0.0065 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9844   -0.1383    0.2618 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1324    0.0291   -1.2180 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0394   -0.9969   -0.8898 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6559   -1.6697   -2.1454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5689   -2.0398    0.0515 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2535    1.6978    0.9435 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2320    0.2800   -0.1755 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0236    1.9269   -0.8707 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9151    1.6460    0.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4740   -0.1838   -1.2987 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929    2.1867    1.0265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2210    0.7690    2.0956 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1427    1.7926    2.4894 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0909    1.4123    1.7767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1594   -0.3321    1.9291 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1197    1.6091   -0.2184 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5855    0.3617    0.8640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8652   -0.3818   -1.9354 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5969    0.8725   -1.7016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6416   -2.1300   -2.5424 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2601   -1.0860   -2.9636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0511   -2.5746   -1.9686 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4393   -3.0411   -0.4479 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9285   -2.0876    0.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6240   -1.9827    0.2928 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  2 19  1  0
  3 20  1  0
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-b-damascone	HMDB
3-Hydroxy-beta-damascone	HMDB

Chemical Formula

C₁₃H₂₀O₂

Average Molecular Weight

208.2967

Monoisotopic Molecular Weight

208.146329884

IUPAC Name

(2E)-1-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-2-en-1-one

Traditional Name

(2E)-1-(4-hydroxy-2,6,6-trimethylcyclohex-1-en-1-yl)but-2-en-1-one

CAS Registry Number

35734-61-3

SMILES

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

InChI Identifier

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

InChI Key

UPRXEFYRIACHQZ-AATRIKPKSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enones

Alternative Parents

Substituents

Enone
Acryloyl-group
Secondary alcohol
Ketone
Organic oxide
Hydrocarbon derivative
Alcohol
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041636)
Cytoplasm (HMDB: HMDB0041636)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041636)

Source

Exogenous

Exogenous (HMDB: HMDB0041636)

Food

Food (HMDB: HMDB0041636)

Plant (HMDB: HMDB0041636)

Process

Not Available

Role

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Emulsifier (HMDB: HMDB0041636)

Biological role

Nutrient (HMDB: HMDB0041636)

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	1.25 g/L	ALOGPS
logP	2.48	ALOGPS
logP	2.66	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	18.91	ChemAxon
pKa (Strongest Basic)	-1.1	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	63.57 m³·mol⁻¹	ChemAxon
Polarizability	24.3 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
DeepCCS	[M+H]+	162.643	30932474
DeepCCS	[M-H]-	160.285	30932474
DeepCCS	[M-2H]-	193.171	30932474
DeepCCS	[M+Na]+	168.736	30932474
AllCCS	[M+H]+	148.9	32859911
AllCCS	[M+H-H2O]+	145.0	32859911
AllCCS	[M+NH4]+	152.5	32859911
AllCCS	[M+Na]+	153.6	32859911
AllCCS	[M-H]-	153.5	32859911
AllCCS	[M+Na-2H]-	154.3	32859911
AllCCS	[M+HCOO]-	155.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one	C\C=C\C(=O)C1=C(C)CC(O)CC1(C)C	2469.5	Standard polar	33892256
(3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one	C\C=C\C(=O)C1=C(C)CC(O)CC1(C)C	1549.0	Standard non polar	33892256
(3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one	C\C=C\C(=O)C1=C(C)CC(O)CC1(C)C	1637.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one,1TMS,isomer #1	C/C=C/C(=O)C1=C(C)CC(O[Si](C)(C)C)CC1(C)C	1670.7	Semi standard non polar	33892256
(3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one,1TBDMS,isomer #1	C/C=C/C(=O)C1=C(C)CC(O[Si](C)(C)C(C)(C)C)CC1(C)C	1931.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-2900000000-0d1f34f7024058f99a27	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one GC-MS (1 TMS) - 70eV, Positive	splash10-030c-9570000000-1aadcd929d1bc0b29e24	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one 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 - (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one 10V, Positive-QTOF	splash10-052f-0950000000-b2ef7c9cf805d700ec04	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one 20V, Positive-QTOF	splash10-05mo-3910000000-f295865a5316eec3c949	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one 40V, Positive-QTOF	splash10-0abm-9500000000-8f7771c27fbfd854750a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one 10V, Negative-QTOF	splash10-0a4i-0390000000-1db45c4005186b8c80f3	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one 20V, Negative-QTOF	splash10-0a4r-3890000000-5bfd4f84a6ebb1a87a2e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one 40V, Negative-QTOF	splash10-00ku-5900000000-5c8586f406b0a71d33a2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one 10V, Negative-QTOF	splash10-000i-0910000000-078d5cb174ea069c9920	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one 20V, Negative-QTOF	splash10-0079-0900000000-36b234393d19ff97cbbb	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one 40V, Negative-QTOF	splash10-00di-3900000000-f9dbc65df8ba744ea602	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one 10V, Positive-QTOF	splash10-0a5i-0930000000-7bec05bbc6d148e2873e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one 20V, Positive-QTOF	splash10-05ai-3910000000-da814e683647d74b1026	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one 40V, Positive-QTOF	splash10-0002-4900000000-b8bbbbccaf4ba2c64d97	2021-09-25	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

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

FDB021865

KNApSAcK ID

Not Available

Chemspider ID

4926545

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6420999

PDB ID

Not Available

ChEBI ID

168043

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

(). Duke, James A. (1992) Handbook of phytochemical constituents of GRAS herbs and other economic plants. Boca Raton, FL. CRC Press.. .

Showing metabocard for (3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one (HMDB0041636)

MOL for HMDB0041636 ((3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one)

3D MOL for HMDB0041636 ((3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one)

3D SDF for HMDB0041636 ((3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one)

3D-SDF for HMDB0041636 ((3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one)

PDB for HMDB0041636 ((3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one)

3D PDB for HMDB0041636 ((3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one)

SMILES for HMDB0041636 ((3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one)

INCHI for HMDB0041636 ((3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one)

Structure for HMDB0041636 ((3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one)

3D Structure for HMDB0041636 ((3R,8E)-3-Hydroxy-5,8-megastigmadien-7-one)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra