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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:45:07 UTC

Update Date

2023-02-21 17:21:17 UTC

HMDB ID

HMDB0031737

Secondary Accession Numbers

HMDB31737

Metabolite Identification

Common Name

delta-Methylionone

Description

delta-Methylionone, also known as δ-methylionone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a significant number of articles have been published on delta-Methylionone.

Structure

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

HMDB0031737
     RDKit          3D
delta-Methylionone
 37 37  0  0  0  0  0  0  0  0999 V2000
    3.9798    1.0827    0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5405   -0.2305   -0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3652   -1.0701   -0.6545 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932   -0.5653   -0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8047   -1.9556   -0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1918    0.2546    0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2311    0.2084    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7880    1.2962    0.7549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1254    2.3861    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1859    1.5183    1.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1440    0.5732    0.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5388   -0.0552   -0.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1776   -0.7434   -0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4967   -1.9058    0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8093   -1.2921   -1.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4564    1.9201   -0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0674    1.1784    0.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7347    1.1125    1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6938   -2.6076   -0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7685   -2.0692   -1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0002   -2.3536   -0.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6860    1.2205    0.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8215    2.0351    2.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4841    3.1938    1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5702    2.8631    0.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3330    1.5745    2.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096    2.5635    0.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0433    1.1322    0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4944   -0.1604    1.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3306    0.6392   -1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2005   -0.8542   -1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8680   -1.8914    1.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3404   -2.8379   -0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5894   -1.9242    0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6409   -2.3823   -1.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7408   -1.1771   -2.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0526   -0.6767   -2.2815 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  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
M  END

  Mrv0541 05061306062D          

 15 15  0  0  0  0            999 V2000
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1842    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2448    1.8695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
 10  1  1  0  0  0  0
 10  7  1  0  0  0  0
 11  2  1  0  0  0  0
 11  9  2  0  0  0  0
 12  3  1  0  0  0  0
 12 11  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  2  0  0  0  0
 14  4  1  0  0  0  0
 14  5  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0031737

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)C(\C)=C\C1=C(C)CCCC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C14H22O/c1-10-7-6-8-14(4,5)13(10)9-11(2)12(3)15/h9H,6-8H2,1-5H3/b11-9+

> <INCHI_KEY>
NSSHGPBKKVJJMM-PKNBQFBNSA-N

> <FORMULA>
C14H22O

> <MOLECULAR_WEIGHT>
206.3239

> <EXACT_MASS>
206.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
25.380668242561473

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
4.49

> <JCHEM_LOGP>
3.6711741596666667

> <ALOGPS_LOGS>
-3.37

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.57830785288312

> <JCHEM_PKA_STRONGEST_BASIC>
-4.628482468177543

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
66.1792

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.80e-02 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0031737
     RDKit          3D
delta-Methylionone
 37 37  0  0  0  0  0  0  0  0999 V2000
    3.9798    1.0827    0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5405   -0.2305   -0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3652   -1.0701   -0.6545 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932   -0.5653   -0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8047   -1.9556   -0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1918    0.2546    0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2311    0.2084    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7880    1.2962    0.7549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1254    2.3861    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1859    1.5183    1.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1440    0.5732    0.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5388   -0.0552   -0.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1776   -0.7434   -0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4967   -1.9058    0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8093   -1.2921   -1.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4564    1.9201   -0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0674    1.1784    0.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7347    1.1125    1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6938   -2.6076   -0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7685   -2.0692   -1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0002   -2.3536   -0.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6860    1.2205    0.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8215    2.0351    2.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4841    3.1938    1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5702    2.8631    0.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3330    1.5745    2.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096    2.5635    0.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0433    1.1322    0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4944   -0.1604    1.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3306    0.6392   -1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2005   -0.8542   -1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8680   -1.8914    1.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3404   -2.8379   -0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5894   -1.9242    0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6409   -2.3823   -1.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7408   -1.1771   -2.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0526   -0.6767   -2.2815 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  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       6.668   3.850   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   14                                                            
CONECT    5   14                                                            
CONECT    6    7    8                                                       
CONECT    7    6   10                                                       
CONECT    8    6   14                                                       
CONECT    9   11   13                                                       
CONECT   10    1    7   13                                                  
CONECT   11    2    9   12                                                  
CONECT   12    3   11   15                                                  
CONECT   13    9   10   14                                                  
CONECT   14    4    5    8   13                                             
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0031737
HETATM    1  C1  UNL     1       3.980   1.083   0.237  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.541  -0.231  -0.262  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.365  -1.070  -0.654  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.093  -0.565  -0.301  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.805  -1.956  -0.658  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.192   0.255   0.087  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.231   0.208   0.146  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.788   1.296   0.755  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.125   2.386   1.269  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.186   1.518   1.055  1.00  0.00           C  
HETATM   11  C10 UNL     1      -3.144   0.573   0.403  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.539  -0.055  -0.782  1.00  0.00           C  
HETATM   13  C12 UNL     1      -1.178  -0.743  -0.440  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.497  -1.906   0.475  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.809  -1.292  -1.802  1.00  0.00           C  
HETATM   16  H1  UNL     1       3.456   1.920  -0.290  1.00  0.00           H  
HETATM   17  H2  UNL     1       5.067   1.178   0.082  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.735   1.113   1.329  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.694  -2.608  -0.270  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.768  -2.069  -1.732  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.000  -2.354  -0.046  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.686   1.221   0.441  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.821   2.035   2.030  1.00  0.00           H  
HETATM   24  H9  UNL     1      -0.484   3.194   1.771  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.570   2.863   0.379  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.333   1.575   2.151  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.410   2.563   0.672  1.00  0.00           H  
HETATM   28  H13 UNL     1      -4.043   1.132   0.073  1.00  0.00           H  
HETATM   29  H14 UNL     1      -3.494  -0.160   1.152  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.331   0.639  -1.611  1.00  0.00           H  
HETATM   31  H16 UNL     1      -3.201  -0.854  -1.160  1.00  0.00           H  
HETATM   32  H17 UNL     1      -0.868  -1.891   1.389  1.00  0.00           H  
HETATM   33  H18 UNL     1      -1.340  -2.838  -0.102  1.00  0.00           H  
HETATM   34  H19 UNL     1      -2.589  -1.924   0.733  1.00  0.00           H  
HETATM   35  H20 UNL     1      -0.641  -2.382  -1.767  1.00  0.00           H  
HETATM   36  H21 UNL     1      -1.741  -1.177  -2.469  1.00  0.00           H  
HETATM   37  H22 UNL     1      -0.053  -0.677  -2.282  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    4
CONECT    4    5    6    6
CONECT    5   19   20   21
CONECT    6    7   22
CONECT    7    8    8   13
CONECT    8    9   10
CONECT    9   23   24   25
CONECT   10   11   26   27
CONECT   11   12   28   29
CONECT   12   13   30   31
CONECT   13   14   15
CONECT   14   32   33   34
CONECT   15   35   36   37
END

HMDB0031737
     RDKit          3D
delta-Methylionone
 37 37  0  0  0  0  0  0  0  0999 V2000
    3.9798    1.0827    0.2366 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5405   -0.2305   -0.2622 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3652   -1.0701   -0.6545 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0932   -0.5653   -0.3007 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8047   -1.9556   -0.6582 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1918    0.2546    0.0871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2311    0.2084    0.1459 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7880    1.2962    0.7549 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1254    2.3861    1.2686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1859    1.5183    1.0555 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1440    0.5732    0.4034 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5388   -0.0552   -0.7817 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1776   -0.7434   -0.4405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4967   -1.9058    0.4745 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8093   -1.2921   -1.8021 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4564    1.9201   -0.2903 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0674    1.1784    0.0820 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7347    1.1125    1.3291 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6938   -2.6076   -0.2698 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7685   -2.0692   -1.7320 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0002   -2.3536   -0.0456 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6860    1.2205    0.4406 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8215    2.0351    2.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4841    3.1938    1.7712 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5702    2.8631    0.3792 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3330    1.5745    2.1514 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4096    2.5635    0.6716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0433    1.1322    0.0727 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4944   -0.1604    1.1521 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3306    0.6392   -1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2005   -0.8542   -1.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8680   -1.8914    1.3890 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3404   -2.8379   -0.1017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5894   -1.9242    0.7326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6409   -2.3823   -1.7674 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7408   -1.1771   -2.4689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0526   -0.6767   -2.2815 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  1  0
  4  6  2  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  8 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 13  7  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  5 19  1  0
  5 20  1  0
  5 21  1  0
  6 22  1  0
  9 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Δ-methylionone	Generator
3-Methyl-b-ionone	HMDB
4-(2,6, 6-Trimethyl-1-cyclohexenyl)-3-methyl-3-buten-2-one	HMDB
4-(2,6,6-Trimethyl-1-cyclohexenyl)-3-methyl-3-buten-2-one	HMDB
b-iso-Methylionone	HMDB
D-Methylionone	HMDB
delta-Iraldeine	HMDB
FEMA 2713	HMDB
Isomethyl-beta-ionone	HMDB
Methyl-delta-ionone	HMDB

Chemical Formula

C₁₄H₂₂O

Average Molecular Weight

206.3239

Monoisotopic Molecular Weight

206.167065326

IUPAC Name

(3E)-3-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one

Traditional Name

(3E)-3-methyl-4-(2,6,6-trimethylcyclohex-1-en-1-yl)but-3-en-2-one

CAS Registry Number

79-89-0

SMILES

CC(=O)C(\C)=C\C1=C(C)CCCC1(C)C

InChI Identifier

InChI=1S/C14H22O/c1-10-7-6-8-14(4,5)13(10)9-11(2)12(3)15/h9H,6-8H2,1-5H3/b11-9+

InChI Key

NSSHGPBKKVJJMM-PKNBQFBNSA-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-branched alpha,beta-unsaturated-ketone
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

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031737)

Source

Endogenous

Endogenous (HMDB: HMDB0031737)

Animal

Animal (HMDB: HMDB0031737)

Exogenous

Food

Food (HMDB: HMDB0031737)

Exogenous (HMDB: HMDB0031737)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0031737)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0031737)

Lipid metabolism pathway (HMDB: HMDB0031737)

Cellular process

Cell signaling (HMDB: HMDB0031737)

Biochemical process

Lipid transport (HMDB: HMDB0031737)

Role

Biological role

Energy source (HMDB: HMDB0031737)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031737)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0031737)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	62.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Boiling Point	301.28 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	2.31 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.008 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.088 g/L	ALOGPS
logP	4.49	ALOGPS
logP	3.67	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	19.58	ChemAxon
pKa (Strongest Basic)	-4.6	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	66.18 m³·mol⁻¹	ChemAxon
Polarizability	25.38 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]+	159.661	30932474
DeepCCS	[M-H]-	157.303	30932474
DeepCCS	[M-2H]-	190.297	30932474
DeepCCS	[M+Na]+	165.754	30932474
AllCCS	[M+H]+	147.3	32859911
AllCCS	[M+H-H2O]+	143.4	32859911
AllCCS	[M+NH4]+	150.9	32859911
AllCCS	[M+Na]+	152.0	32859911
AllCCS	[M-H]-	155.2	32859911
AllCCS	[M+Na-2H]-	156.2	32859911
AllCCS	[M+HCOO]-	157.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
delta-Methylionone	CC(=O)C(\C)=C\C1=C(C)CCCC1(C)C	1820.4	Standard polar	33892256
delta-Methylionone	CC(=O)C(\C)=C\C1=C(C)CCCC1(C)C	1538.9	Standard non polar	33892256
delta-Methylionone	CC(=O)C(\C)=C\C1=C(C)CCCC1(C)C	1506.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
delta-Methylionone,1TMS,isomer #1	C=C(O[Si](C)(C)C)/C(C)=C/C1=C(C)CCCC1(C)C	1644.1	Semi standard non polar	33892256
delta-Methylionone,1TMS,isomer #1	C=C(O[Si](C)(C)C)/C(C)=C/C1=C(C)CCCC1(C)C	1681.4	Standard non polar	33892256
delta-Methylionone,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)/C(C)=C/C1=C(C)CCCC1(C)C	1860.3	Semi standard non polar	33892256
delta-Methylionone,1TBDMS,isomer #1	C=C(O[Si](C)(C)C(C)(C)C)/C(C)=C/C1=C(C)CCCC1(C)C	1906.1	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - delta-Methylionone GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ox-2900000000-591f5c40bdcd447ac6eb	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - delta-Methylionone 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 - delta-Methylionone 10V, Positive-QTOF	splash10-0a4i-3980000000-03e8a62eda77589e1b8e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Methylionone 20V, Positive-QTOF	splash10-05n0-6910000000-036ff3133945a2d00159	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Methylionone 40V, Positive-QTOF	splash10-1003-9300000000-8d04eebaeb88fb42999f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Methylionone 10V, Negative-QTOF	splash10-0a4i-0190000000-ceafb1926e4e5978a746	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Methylionone 20V, Negative-QTOF	splash10-0bt9-2890000000-bf7cbeb1e62dc5ec9d75	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Methylionone 40V, Negative-QTOF	splash10-02ga-4900000000-f7957e4beda95b179909	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Methylionone 10V, Positive-QTOF	splash10-000i-1910000000-728c239e8cf3697cabff	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Methylionone 20V, Positive-QTOF	splash10-0600-7900000000-66cbf6ef9b7f29e5928e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Methylionone 40V, Positive-QTOF	splash10-0006-9300000000-52196c794798dcaf6467	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Methylionone 10V, Negative-QTOF	splash10-0a4i-0490000000-626a1896cc5089dca358	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Methylionone 20V, Negative-QTOF	splash10-0a4i-0790000000-56276d7995cc937849ef	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - delta-Methylionone 40V, Negative-QTOF	splash10-0kuf-7910000000-32dfec568909b7404628	2021-09-23	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

FDB008405

KNApSAcK ID

Not Available

Chemspider ID

4522526

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5372195

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1045331

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 delta-Methylionone (HMDB0031737)

MOL for HMDB0031737 (delta-Methylionone)

3D MOL for HMDB0031737 (delta-Methylionone)

3D SDF for HMDB0031737 (delta-Methylionone)

3D-SDF for HMDB0031737 (delta-Methylionone)

PDB for HMDB0031737 (delta-Methylionone)

3D PDB for HMDB0031737 (delta-Methylionone)

SMILES for HMDB0031737 (delta-Methylionone)

INCHI for HMDB0031737 (delta-Methylionone)

Structure for HMDB0031737 (delta-Methylionone)

3D Structure for HMDB0031737 (delta-Methylionone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra