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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:46:29 UTC

Update Date

2023-02-21 17:24:53 UTC

HMDB ID

HMDB0035753

Secondary Accession Numbers

HMDB35753

Metabolite Identification

Common Name

(R)-(E)-4,7-Megastigmadien-9-one

Description

(R)-(E)-4,7-Megastigmadien-9-one belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on (R)-(E)-4,7-Megastigmadien-9-one.

Structure

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

HMDB0035753
     RDKit          3D
(R)-(E)-4,7-Megastigmadien-9-one
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.7621    0.0789   -0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4610    0.5250    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539    1.4207    1.3434 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238   -0.0386    0.0222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0288    0.3209    0.4713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1756   -0.3128   -0.0471 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9520   -1.0498    0.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4645   -1.3030    2.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1570   -1.4857    0.6085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7352   -1.2880   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1004   -0.1896   -1.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1401    0.6492   -0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705    1.5364   -1.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8731    1.4986    0.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8129    0.2689   -1.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6219    0.4894    0.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7817   -1.0456    0.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466   -0.8269   -0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985    1.0926    1.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879   -1.0671   -0.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8366   -2.3182    2.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8767   -0.5991    3.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362   -1.3118    2.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7590   -2.0330    1.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8308   -1.1706   -0.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5732   -2.2458   -1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9293    0.4597   -1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5550   -0.5663   -2.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0686    2.4632   -1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625    1.0503   -1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9889    1.7832   -2.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854    1.5663    1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9839    2.5433   -0.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219    1.1053    0.3594 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  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  5 19  1  0
  6 20  1  6
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 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 02241215342D          

 14 14  0  0  0  0            999 V2000
   -1.3259   -2.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0404   -2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0404   -3.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3259   -3.7714    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6114   -3.3589    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6114   -2.5339    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.1030   -2.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8175   -2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5320   -2.1214    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2465   -2.5339    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5320   -1.2964    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394   -1.3245    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9134   -1.4069    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1031   -3.7714    0.0000 C   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
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  6  7  1  1  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  9 11  2  0  0  0  0
  1 12  1  0  0  0  0
  1 13  1  0  0  0  0
  5 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035753

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)\C=C\[C@H]1C(C)=CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,12H,5,9H2,1-4H3/b8-7+/t12-/m0/s1

> <INCHI_KEY>
UZFLPKAIBPNNCA-GUOLPTJISA-N

> <FORMULA>
C13H20O

> <MOLECULAR_WEIGHT>
192.2973

> <EXACT_MASS>
192.151415262

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
23.07775356512076

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-4-[(1R)-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one

> <ALOGPS_LOGP>
4.14

> <JCHEM_LOGP>
3.3192814949999994

> <ALOGPS_LOGS>
-3.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.830428760239922

> <JCHEM_PKA_STRONGEST_BASIC>
-4.904326214789516

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
62.088699999999996

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.96e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3E)-4-[(1R)-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0035753
     RDKit          3D
(R)-(E)-4,7-Megastigmadien-9-one
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.7621    0.0789   -0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4610    0.5250    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539    1.4207    1.3434 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238   -0.0386    0.0222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0288    0.3209    0.4713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1756   -0.3128   -0.0471 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9520   -1.0498    0.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4645   -1.3030    2.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1570   -1.4857    0.6085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7352   -1.2880   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1004   -0.1896   -1.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1401    0.6492   -0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705    1.5364   -1.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8731    1.4986    0.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8129    0.2689   -1.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6219    0.4894    0.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7817   -1.0456    0.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466   -0.8269   -0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985    1.0926    1.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879   -1.0671   -0.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8366   -2.3182    2.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8767   -0.5991    3.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362   -1.3118    2.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7590   -2.0330    1.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8308   -1.1706   -0.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5732   -2.2458   -1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9293    0.4597   -1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5550   -0.5663   -2.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0686    2.4632   -1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625    1.0503   -1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9889    1.7832   -2.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854    1.5663    1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9839    2.5433   -0.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219    1.1053    0.3594 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  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  5 19  1  0
  6 20  1  6
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 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      -2.475  -3.960   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.809  -4.730   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.809  -6.270   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.475  -7.040   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.141  -6.270   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.141  -4.730   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       0.192  -3.960   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.526  -4.730   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.860  -3.960   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.193  -4.730   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       2.860  -2.420   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -2.874  -2.472   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.705  -2.626   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.192  -7.040   0.000  0.00  0.00           C+0
CONECT    1    2    6   12   13                                             
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    5    1    7                                                  
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10   11                                                  
CONECT   10    9                                                            
CONECT   11    9                                                            
CONECT   12    1                                                            
CONECT   13    1                                                            
CONECT   14    5                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0035753
HETATM    1  C1  UNL     1       4.762   0.079  -0.073  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.461   0.525   0.470  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.454   1.421   1.343  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.224  -0.039   0.022  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.029   0.321   0.471  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.176  -0.313  -0.047  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.952  -1.050   0.991  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.465  -1.303   2.356  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.157  -1.486   0.609  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.735  -1.288  -0.721  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.100  -0.190  -1.521  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.140   0.649  -0.705  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.370   1.536  -1.645  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.873   1.499   0.292  1.00  0.00           C  
HETATM   15  H1  UNL     1       4.813   0.269  -1.175  1.00  0.00           H  
HETATM   16  H2  UNL     1       5.622   0.489   0.456  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.782  -1.046   0.017  1.00  0.00           H  
HETATM   18  H4  UNL     1       2.247  -0.827  -0.748  1.00  0.00           H  
HETATM   19  H5  UNL     1       0.999   1.093   1.226  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.088  -1.067  -0.824  1.00  0.00           H  
HETATM   21  H7  UNL     1      -0.837  -2.318   2.657  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.877  -0.599   3.107  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.636  -1.312   2.442  1.00  0.00           H  
HETATM   24  H10 UNL     1      -2.759  -2.033   1.345  1.00  0.00           H  
HETATM   25  H11 UNL     1      -3.831  -1.171  -0.622  1.00  0.00           H  
HETATM   26  H12 UNL     1      -2.573  -2.246  -1.297  1.00  0.00           H  
HETATM   27  H13 UNL     1      -2.929   0.460  -1.907  1.00  0.00           H  
HETATM   28  H14 UNL     1      -1.555  -0.566  -2.407  1.00  0.00           H  
HETATM   29  H15 UNL     1      -0.069   2.463  -1.100  1.00  0.00           H  
HETATM   30  H16 UNL     1       0.562   1.050  -1.987  1.00  0.00           H  
HETATM   31  H17 UNL     1      -0.989   1.783  -2.538  1.00  0.00           H  
HETATM   32  H18 UNL     1      -1.385   1.566   1.270  1.00  0.00           H  
HETATM   33  H19 UNL     1      -1.984   2.543  -0.116  1.00  0.00           H  
HETATM   34  H20 UNL     1      -2.922   1.105   0.359  1.00  0.00           H  
CONECT    1    2   15   16   17
CONECT    2    3    3    4
CONECT    4    5    5   18
CONECT    5    6   19
CONECT    6    7   12   20
CONECT    7    8    9    9
CONECT    8   21   22   23
CONECT    9   10   24
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

HMDB0035753
     RDKit          3D
(R)-(E)-4,7-Megastigmadien-9-one
 34 34  0  0  0  0  0  0  0  0999 V2000
    4.7621    0.0789   -0.0727 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4610    0.5250    0.4696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4539    1.4207    1.3434 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2238   -0.0386    0.0222 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0288    0.3209    0.4713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1756   -0.3128   -0.0471 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.9520   -1.0498    0.9912 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4645   -1.3030    2.3560 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1570   -1.4857    0.6085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7352   -1.2880   -0.7215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1004   -0.1896   -1.5207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1401    0.6492   -0.7052 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3705    1.5364   -1.6454 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8731    1.4986    0.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8129    0.2689   -1.1747 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6219    0.4894    0.4558 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7817   -1.0456    0.0165 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2466   -0.8269   -0.7482 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9985    1.0926    1.2262 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0879   -1.0671   -0.8239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8366   -2.3182    2.6574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8767   -0.5991    3.1068 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6362   -1.3118    2.4419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7590   -2.0330    1.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8308   -1.1706   -0.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5732   -2.2458   -1.2968 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9293    0.4597   -1.9073 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5550   -0.5663   -2.4074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0686    2.4632   -1.0999 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5625    1.0503   -1.9869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9889    1.7832   -2.5384 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3854    1.5663    1.2697 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9839    2.5433   -0.1156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9219    1.1053    0.3594 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  1  0
  6  7  1  0
  7  8  1  0
  7  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 12 14  1  0
 12  6  1  0
  1 15  1  0
  1 16  1  0
  1 17  1  0
  4 18  1  0
  5 19  1  0
  6 20  1  6
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 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

Value	Source
(+)-(6R)-alpha-Ionone	HMDB
(+)-alpha-Ionone	HMDB
(R)-(+)-alpha-Ionone	HMDB
(R)-alpha-Ionone	HMDB
(R-(e))-4-(2,6,6-Trimethyl-2-cyclohexen-1-yl)-3-buten-2-one	HMDB
3-Buten-2-one, 4-(2,6,6-trimethyl-2-cyclohexen-1-yl)-, (R)-(+)- (8ci)	HMDB
4-[(1R)-2,6,6-Trimethyl-2-cyclohexen-1-yl]-(3E)-3-buten-2-one	HMDB
Parmone	HMDB

Chemical Formula

C₁₃H₂₀O

Average Molecular Weight

192.2973

Monoisotopic Molecular Weight

192.151415262

IUPAC Name

(3E)-4-[(1R)-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one

Traditional Name

(3E)-4-[(1R)-2,6,6-trimethylcyclohex-2-en-1-yl]but-3-en-2-one

CAS Registry Number

24190-29-2

SMILES

CC(=O)\C=C\[C@H]1C(C)=CCCC1(C)C

InChI Identifier

InChI=1S/C13H20O/c1-10-6-5-9-13(3,4)12(10)8-7-11(2)14/h6-8,12H,5,9H2,1-4H3/b8-7+/t12-/m0/s1

InChI Key

UZFLPKAIBPNNCA-GUOLPTJISA-N

Chemical Taxonomy

Description

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

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Sesquiterpenoids

Alternative Parents

Substituents

Cyclofarsesane sesquiterpenoid
Megastigmane sesquiterpenoid
Sesquiterpenoid
Ionone derivative
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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: HMDB0035753)

Source

Endogenous

Endogenous (HMDB: HMDB0035753)

Animal

Animal (HMDB: HMDB0035753)

Exogenous

Food

Food (HMDB: HMDB0035753)

Exogenous (HMDB: HMDB0035753)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035753)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035753)

Lipid metabolism pathway (HMDB: HMDB0035753)

Cellular process

Cell signaling (HMDB: HMDB0035753)

Biochemical process

Lipid transport (HMDB: HMDB0035753)

Role

Biological role

Energy source (HMDB: HMDB0035753)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035753)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0035753)

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	24.67 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	0.05 g/L	ALOGPS
logP	4.14	ALOGPS
logP	3.32	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Acidic)	19.83	ChemAxon
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	62.09 m³·mol⁻¹	ChemAxon
Polarizability	23.08 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]+	151.038	30932474
DeepCCS	[M-H]-	148.642	30932474
DeepCCS	[M-2H]-	181.735	30932474
DeepCCS	[M+Na]+	156.95	30932474
AllCCS	[M+H]+	143.0	32859911
AllCCS	[M+H-H2O]+	138.9	32859911
AllCCS	[M+NH4]+	146.8	32859911
AllCCS	[M+Na]+	147.9	32859911
AllCCS	[M-H]-	149.7	32859911
AllCCS	[M+Na-2H]-	150.7	32859911
AllCCS	[M+HCOO]-	151.8	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 √ó 2.1 mm; 1.7 Œºmparticle diameter). Predicted by Afia on May 17, 2022.	7.04 minutes	32390414
Predicted by Siyang on May 30, 2022	17.5998 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.08 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2396.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	572.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	214.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	340.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	169.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	641.4 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	672.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	80.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1494.5 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	507.9 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	1311.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	548.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	381.2 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	392.9 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	554.9 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	8.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(R)-(E)-4,7-Megastigmadien-9-one	CC(=O)\C=C\[C@H]1C(C)=CCCC1(C)C	1813.0	Standard polar	33892256
(R)-(E)-4,7-Megastigmadien-9-one	CC(=O)\C=C\[C@H]1C(C)=CCCC1(C)C	1419.6	Standard non polar	33892256
(R)-(E)-4,7-Megastigmadien-9-one	CC(=O)\C=C\[C@H]1C(C)=CCCC1(C)C	1424.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(R)-(E)-4,7-Megastigmadien-9-one,1TMS,isomer #1	C=C(/C=C/[C@H]1C(C)=CCCC1(C)C)O[Si](C)(C)C	1602.3	Semi standard non polar	33892256
(R)-(E)-4,7-Megastigmadien-9-one,1TMS,isomer #1	C=C(/C=C/[C@H]1C(C)=CCCC1(C)C)O[Si](C)(C)C	1632.0	Standard non polar	33892256
(R)-(E)-4,7-Megastigmadien-9-one,1TBDMS,isomer #1	C=C(/C=C/[C@H]1C(C)=CCCC1(C)C)O[Si](C)(C)C(C)(C)C	1839.8	Semi standard non polar	33892256
(R)-(E)-4,7-Megastigmadien-9-one,1TBDMS,isomer #1	C=C(/C=C/[C@H]1C(C)=CCCC1(C)C)O[Si](C)(C)C(C)(C)C	1867.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one EI-B (Non-derivatized)	splash10-0006-9600000000-f52514927b7c7e5bd79a	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one EI-B (Non-derivatized)	splash10-0006-9600000000-93c21f85616fb52a6763	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one EI-B (Non-derivatized)	splash10-0076-6900000000-0d604eb8b56437636516	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one EI-B (Non-derivatized)	splash10-0006-9600000000-f52514927b7c7e5bd79a	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one EI-B (Non-derivatized)	splash10-0006-9600000000-93c21f85616fb52a6763	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one EI-B (Non-derivatized)	splash10-0076-6900000000-0d604eb8b56437636516	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fia-4900000000-9e9a8dc88676517f4055	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-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 - (R)-(E)-4,7-Megastigmadien-9-one 10V, Positive-QTOF	splash10-002f-0900000000-0d1ee7a07c25e0eb379a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 20V, Positive-QTOF	splash10-004u-3900000000-122599cd5a3606da3858	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 40V, Positive-QTOF	splash10-014i-9400000000-5525adff7c75947a3830	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 10V, Negative-QTOF	splash10-0006-0900000000-86ad4191ecec06d667eb	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 20V, Negative-QTOF	splash10-0006-0900000000-81ca79f706995e1f2313	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 40V, Negative-QTOF	splash10-0aed-2900000000-e754146e5b21f942f91e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 10V, Negative-QTOF	splash10-0006-0900000000-14436e4d9ff8d032db54	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 20V, Negative-QTOF	splash10-00di-0900000000-7cd7cf4235cb00fbc0b5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 40V, Negative-QTOF	splash10-0kmj-3900000000-b5da866d6db21994e86c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 10V, Positive-QTOF	splash10-006x-0900000000-dca766c12d151f3d74b1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 20V, Positive-QTOF	splash10-05fu-8900000000-26ead371c8e940e8859e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (R)-(E)-4,7-Megastigmadien-9-one 40V, Positive-QTOF	splash10-05mo-9600000000-ad142c26c199a3741a02	2021-09-24	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

FDB014487

KNApSAcK ID

Not Available

Chemspider ID

4594306

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5498521

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1445651

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (R)-(E)-4,7-Megastigmadien-9-one (HMDB0035753)

MOL for HMDB0035753 ((R)-(E)-4,7-Megastigmadien-9-one)

3D MOL for HMDB0035753 ((R)-(E)-4,7-Megastigmadien-9-one)

3D SDF for HMDB0035753 ((R)-(E)-4,7-Megastigmadien-9-one)

3D-SDF for HMDB0035753 ((R)-(E)-4,7-Megastigmadien-9-one)

PDB for HMDB0035753 ((R)-(E)-4,7-Megastigmadien-9-one)

3D PDB for HMDB0035753 ((R)-(E)-4,7-Megastigmadien-9-one)

SMILES for HMDB0035753 ((R)-(E)-4,7-Megastigmadien-9-one)

INCHI for HMDB0035753 ((R)-(E)-4,7-Megastigmadien-9-one)

Structure for HMDB0035753 ((R)-(E)-4,7-Megastigmadien-9-one)

3D Structure for HMDB0035753 ((R)-(E)-4,7-Megastigmadien-9-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra