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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 19:34:10 UTC

Update Date

2023-02-21 17:24:21 UTC

HMDB ID

HMDB0034671

Secondary Accession Numbers

HMDB34671

Metabolite Identification

Common Name

(E)-5,8-Megastigmadien-4-one

Description

(E)-5,8-Megastigmadien-4-one belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond (E)-5,8-Megastigmadien-4-one has been detected, but not quantified in, fruits. This could make (e)-5,8-megastigmadien-4-one a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on (E)-5,8-Megastigmadien-4-one.

Structure

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

HMDB0034671
     RDKit          3D
(E)-5,8-Megastigmadien-4-one
 34 34  0  0  0  0  0  0  0  0999 V2000
    3.5559   -0.9796   -0.7038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    0.2739    0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3406    0.5578    0.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1739   -0.2961    0.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964    0.1839    0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3516    1.3775   -0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6386    2.4667   -0.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7289    1.6683   -0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1510    2.8689   -0.5587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461    0.6343   -1.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0200   -0.7137   -1.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -0.7757    0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2419   -0.4169    1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7812   -2.1921    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5666   -0.9714   -1.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4724   -1.8773   -0.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8331   -0.9377   -1.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2843    0.9675    0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3564    1.4614    1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4407   -1.1997    0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0332   -0.8195    1.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2317    3.2900   -0.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960    3.0189    0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486    2.1534   -0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8690    0.8198   -2.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6335    0.6462   -0.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3912   -1.0170   -1.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8398   -1.4567   -0.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3038    0.6773    1.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304   -0.9640    2.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2581   -0.7481    1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6684   -2.8482    0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906   -2.4691   -0.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3686   -2.3831    1.4915 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  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
M  END


  Mrv0541 02241217072D          

 14 14  0  0  0  0            999 V2000
    1.0721    0.0829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6596    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6596    1.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004    2.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    1.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421    0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0829    0.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0829   -0.4121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -0.8246    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7421   -1.6496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0004   -2.0621    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4846    0.9896    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846    0.4129    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4846    2.0621    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
  5  6  1  0  0  0  0
  5 14  2  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
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0034671

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C/CC1=C(C)C(=O)CCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O/c1-5-6-7-11-10(2)12(14)8-9-13(11,3)4/h5-6H,7-9H2,1-4H3/b6-5-

> <INCHI_KEY>
CVDHBGKYPTUEAA-WAYWQWQTSA-N

> <FORMULA>
C13H20O

> <MOLECULAR_WEIGHT>
192.2973

> <EXACT_MASS>
192.151415262

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
22.988276970410627

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3-[(2Z)-but-2-en-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

> <ALOGPS_LOGP>
4.30

> <JCHEM_LOGP>
3.683780070000001

> <ALOGPS_LOGS>
-3.13

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.879184435808783

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
61.9231

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3-[(2Z)-but-2-en-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0034671
     RDKit          3D
(E)-5,8-Megastigmadien-4-one
 34 34  0  0  0  0  0  0  0  0999 V2000
    3.5559   -0.9796   -0.7038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    0.2739    0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3406    0.5578    0.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1739   -0.2961    0.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964    0.1839    0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3516    1.3775   -0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6386    2.4667   -0.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7289    1.6683   -0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1510    2.8689   -0.5587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461    0.6343   -1.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0200   -0.7137   -1.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -0.7757    0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2419   -0.4169    1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7812   -2.1921    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5666   -0.9714   -1.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4724   -1.8773   -0.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8331   -0.9377   -1.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2843    0.9675    0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3564    1.4614    1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4407   -1.1997    0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0332   -0.8195    1.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2317    3.2900   -0.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960    3.0189    0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486    2.1534   -0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8690    0.8198   -2.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6335    0.6462   -0.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3912   -1.0170   -1.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8398   -1.4567   -0.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3038    0.6773    1.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304   -0.9640    2.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2581   -0.7481    1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6684   -2.8482    0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906   -2.4691   -0.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3686   -2.3831    1.4915 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  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       2.001   0.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.231   1.539   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.231   3.079   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.001   3.849   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.385   3.079   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.385   1.539   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.155   0.771   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.155  -0.769   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.385  -1.539   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.385  -3.079   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.001  -3.849   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.771   1.847   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.771   0.771   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0      -2.771   3.849   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                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    7   13                                                  
CONECT    7    2    6    8                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10                                                            
CONECT   12    2                                                            
CONECT   13    6                                                            
CONECT   14    5                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0034671
HETATM    1  C1  UNL     1       3.556  -0.980  -0.704  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.466   0.274   0.133  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.341   0.558   0.803  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.174  -0.296   0.767  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.096   0.184   0.277  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.352   1.377  -0.185  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.639   2.467  -0.289  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.729   1.668  -0.637  1.00  0.00           C  
HETATM    9  O1  UNL     1      -2.151   2.869  -0.559  1.00  0.00           O  
HETATM   10  C9  UNL     1      -2.646   0.634  -1.178  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.020  -0.714  -1.013  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.267  -0.776   0.297  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.242  -0.417   1.396  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.781  -2.192   0.490  1.00  0.00           C  
HETATM   15  H1  UNL     1       4.567  -0.971  -1.161  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.472  -1.877  -0.093  1.00  0.00           H  
HETATM   17  H3  UNL     1       2.833  -0.938  -1.543  1.00  0.00           H  
HETATM   18  H4  UNL     1       4.284   0.967   0.218  1.00  0.00           H  
HETATM   19  H5  UNL     1       2.356   1.461   1.388  1.00  0.00           H  
HETATM   20  H6  UNL     1       1.441  -1.200   0.119  1.00  0.00           H  
HETATM   21  H7  UNL     1       1.033  -0.820   1.784  1.00  0.00           H  
HETATM   22  H8  UNL     1       0.232   3.290  -0.961  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.796   3.019   0.669  1.00  0.00           H  
HETATM   24  H10 UNL     1       1.549   2.153  -0.805  1.00  0.00           H  
HETATM   25  H11 UNL     1      -2.869   0.820  -2.244  1.00  0.00           H  
HETATM   26  H12 UNL     1      -3.634   0.646  -0.643  1.00  0.00           H  
HETATM   27  H13 UNL     1      -1.391  -1.017  -1.873  1.00  0.00           H  
HETATM   28  H14 UNL     1      -2.840  -1.457  -0.935  1.00  0.00           H  
HETATM   29  H15 UNL     1      -2.304   0.677   1.544  1.00  0.00           H  
HETATM   30  H16 UNL     1      -2.030  -0.964   2.337  1.00  0.00           H  
HETATM   31  H17 UNL     1      -3.258  -0.748   1.064  1.00  0.00           H  
HETATM   32  H18 UNL     1      -1.668  -2.848   0.378  1.00  0.00           H  
HETATM   33  H19 UNL     1      -0.091  -2.469  -0.332  1.00  0.00           H  
HETATM   34  H20 UNL     1      -0.369  -2.383   1.492  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    3   18
CONECT    3    4   19
CONECT    4    5   20   21
CONECT    5    6    6   12
CONECT    6    7    8
CONECT    7   22   23   24
CONECT    8    9    9   10
CONECT   10   11   25   26
CONECT   11   12   27   28
CONECT   12   13   14
CONECT   13   29   30   31
CONECT   14   32   33   34
END

HMDB0034671
     RDKit          3D
(E)-5,8-Megastigmadien-4-one
 34 34  0  0  0  0  0  0  0  0999 V2000
    3.5559   -0.9796   -0.7038 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4655    0.2739    0.1328 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3406    0.5578    0.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1739   -0.2961    0.7674 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0964    0.1839    0.2773 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3516    1.3775   -0.1853 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6386    2.4667   -0.2888 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7289    1.6683   -0.6371 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1510    2.8689   -0.5587 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6461    0.6343   -1.1776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0200   -0.7137   -1.0132 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2670   -0.7757    0.2971 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2419   -0.4169    1.3960 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7812   -2.1921    0.4903 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5666   -0.9714   -1.1608 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4724   -1.8773   -0.0932 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8331   -0.9377   -1.5426 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2843    0.9675    0.2176 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3564    1.4614    1.3878 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4407   -1.1997    0.1193 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0332   -0.8195    1.7842 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2317    3.2900   -0.9607 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7960    3.0189    0.6689 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5486    2.1534   -0.8052 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8690    0.8198   -2.2445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6335    0.6462   -0.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3912   -1.0170   -1.8733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8398   -1.4567   -0.9353 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3038    0.6773    1.5440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0304   -0.9640    2.3373 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2581   -0.7481    1.0636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6684   -2.8482    0.3781 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0906   -2.4691   -0.3324 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3686   -2.3831    1.4915 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  1  0
  5  6  2  0
  6  7  1  0
  6  8  1  0
  8  9  2  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12  5  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  2 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  7 22  1  0
  7 23  1  0
  7 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₃H₂₀O

Average Molecular Weight

192.2973

Monoisotopic Molecular Weight

192.151415262

IUPAC Name

3-[(2Z)-but-2-en-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

Traditional Name

3-[(2Z)-but-2-en-1-yl]-2,4,4-trimethylcyclohex-2-en-1-one

CAS Registry Number

67401-26-7

SMILES

C\C=C/CC1=C(C)C(=O)CCC1(C)C

InChI Identifier

InChI=1S/C13H20O/c1-5-6-7-11-10(2)12(14)8-9-13(11,3)4/h5-6H,7-9H2,1-4H3/b6-5-

InChI Key

CVDHBGKYPTUEAA-WAYWQWQTSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclohexenones. Cyclohexenones are compounds containing a cylohexenone moiety, which is a six-membered aliphatic ring that carries a ketone and has one endocyclic double bond.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclohexenones

Alternative Parents

Substituents

Cyclohexenone
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0034671)

Source

Exogenous

Food

Food (HMDB: HMDB0034671)

Fruit

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0034671)

Endogenous

Plant

Plant (HMDB: HMDB0034671)

Endogenous (HMDB: HMDB0034671)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0034671)

Role

Biological role

Energy source (HMDB: HMDB0034671)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0034671)

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	7.99 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	4.3	ALOGPS
logP	3.68	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-4.9	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	61.92 m³·mol⁻¹	ChemAxon
Polarizability	22.99 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
DarkChem	[M+H]+	149.703	31661259
DarkChem	[M-H]-	142.864	31661259
DeepCCS	[M+H]+	152.177	30932474
DeepCCS	[M-H]-	149.819	30932474
DeepCCS	[M-2H]-	183.854	30932474
DeepCCS	[M+Na]+	158.611	30932474
AllCCS	[M+H]+	143.3	32859911
AllCCS	[M+H-H2O]+	139.2	32859911
AllCCS	[M+NH4]+	147.1	32859911
AllCCS	[M+Na]+	148.2	32859911
AllCCS	[M-H]-	149.4	32859911
AllCCS	[M+Na-2H]-	150.3	32859911
AllCCS	[M+HCOO]-	151.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022.	7.55 minutes	32390414
Predicted by Siyang on May 30, 2022	17.4086 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	0.99 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.2 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2499.0 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	553.2 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	214.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	333.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	176.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	659.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	695.7 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	67.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1462.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	510.5 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	1301.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	490.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	413.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	385.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	559.8 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	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(E)-5,8-Megastigmadien-4-one	C\C=C/CC1=C(C)C(=O)CCC1(C)C	2030.7	Standard polar	33892256
(E)-5,8-Megastigmadien-4-one	C\C=C/CC1=C(C)C(=O)CCC1(C)C	1506.1	Standard non polar	33892256
(E)-5,8-Megastigmadien-4-one	C\C=C/CC1=C(C)C(=O)CCC1(C)C	1512.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(E)-5,8-Megastigmadien-4-one,1TMS,isomer #1	C/C=C\CC1=C(C)C(O[Si](C)(C)C)=CCC1(C)C	1646.0	Semi standard non polar	33892256
(E)-5,8-Megastigmadien-4-one,1TMS,isomer #1	C/C=C\CC1=C(C)C(O[Si](C)(C)C)=CCC1(C)C	1550.0	Standard non polar	33892256
(E)-5,8-Megastigmadien-4-one,1TBDMS,isomer #1	C/C=C\CC1=C(C)C(O[Si](C)(C)C(C)(C)C)=CCC1(C)C	1857.0	Semi standard non polar	33892256
(E)-5,8-Megastigmadien-4-one,1TBDMS,isomer #1	C/C=C\CC1=C(C)C(O[Si](C)(C)C(C)(C)C)=CCC1(C)C	1737.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-5,8-Megastigmadien-4-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-07fr-4900000000-c30f4e44ba9cb60c8943	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-5,8-Megastigmadien-4-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 - (E)-5,8-Megastigmadien-4-one 10V, Positive-QTOF	splash10-0006-1900000000-44170c6aa62829077c8a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-5,8-Megastigmadien-4-one 20V, Positive-QTOF	splash10-00kf-7900000000-cd7b766981473bd54f9c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-5,8-Megastigmadien-4-one 40V, Positive-QTOF	splash10-0gbc-9100000000-538f5485c5d29797c95c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-5,8-Megastigmadien-4-one 10V, Negative-QTOF	splash10-0006-0900000000-4a2256b79df33f8e587f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-5,8-Megastigmadien-4-one 20V, Negative-QTOF	splash10-0006-0900000000-c09fea300060fb41767d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-5,8-Megastigmadien-4-one 40V, Negative-QTOF	splash10-002f-3900000000-9cbec903fbb2bf375eb6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-5,8-Megastigmadien-4-one 10V, Negative-QTOF	splash10-0006-0900000000-14436e4d9ff8d032db54	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-5,8-Megastigmadien-4-one 20V, Negative-QTOF	splash10-0006-0900000000-b81bd97e6a13f88681e2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-5,8-Megastigmadien-4-one 40V, Negative-QTOF	splash10-03dj-0900000000-746aca2c8255fb0b3af3	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-5,8-Megastigmadien-4-one 10V, Positive-QTOF	splash10-000l-2900000000-f47cdee29ea6699e1f88	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-5,8-Megastigmadien-4-one 20V, Positive-QTOF	splash10-00li-6900000000-4534eda9931e9ce90c4f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-5,8-Megastigmadien-4-one 40V, Positive-QTOF	splash10-014l-9100000000-f50f9f81253ede485a51	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+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB013196

KNApSAcK ID

Not Available

Chemspider ID

20058568

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14109911

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1506381

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for (E)-5,8-Megastigmadien-4-one (HMDB0034671)

MOL for HMDB0034671 ((E)-5,8-Megastigmadien-4-one)

3D MOL for HMDB0034671 ((E)-5,8-Megastigmadien-4-one)

3D SDF for HMDB0034671 ((E)-5,8-Megastigmadien-4-one)

3D-SDF for HMDB0034671 ((E)-5,8-Megastigmadien-4-one)

PDB for HMDB0034671 ((E)-5,8-Megastigmadien-4-one)

3D PDB for HMDB0034671 ((E)-5,8-Megastigmadien-4-one)

SMILES for HMDB0034671 ((E)-5,8-Megastigmadien-4-one)

INCHI for HMDB0034671 ((E)-5,8-Megastigmadien-4-one)

Structure for HMDB0034671 ((E)-5,8-Megastigmadien-4-one)

3D Structure for HMDB0034671 ((E)-5,8-Megastigmadien-4-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra