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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 20:38:32 UTC

Update Date

2022-03-07 02:54:34 UTC

HMDB ID

HMDB0035631

Secondary Accession Numbers

HMDB35631

Metabolite Identification

Common Name

alpha-Irone

Description

alpha-Irone, also known as 6-methyl-a-ionone or α-iron, 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 alpha-Irone.

Structure

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

HMDB0035631
     RDKit          3D
alpha-Irone
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.5967   -0.4363   -1.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6498    0.3440   -0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0936    1.3829    0.1445 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540   -0.0264   -0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4420    0.6983    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0430    0.4772    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6816    1.7147    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0228    2.9254   -0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9868    1.7064    0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7441    0.5548    0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473   -0.7387    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809   -1.7838    0.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6449   -0.6823    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9118   -0.5956   -1.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0088   -2.0210    0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0995    0.2369   -1.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1013   -1.2391   -1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4203   -0.8643   -0.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8226   -0.8994   -0.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8743    1.6010    0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853    0.4623    1.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2478    3.5954    0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5311    3.4223   -0.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.6488   -0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5422    2.5929    0.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7015    0.4987    0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0805    0.7833    1.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8680   -1.1245    1.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2751   -2.6385   -0.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4779   -1.3116   -0.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5833   -2.2012    0.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9842   -1.6524   -1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8951   -0.1333   -1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1207   -0.0521   -1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2087   -2.6248   -0.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666   -1.9228    1.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7084   -2.6967    1.1464 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
 11 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
  4 19  1  0
  5 20  1  0
  6 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 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 05061308362D          

 15 15  0  0  0  0            999 V2000
   -0.7145   -0.4125    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
   -2.8579    0.8250    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
    0.1842    1.8695    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
    1.4289    0.0000    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
    0.0000    0.0000    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
   -2.1434    1.2375    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
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  9  8  2  0  0  0  0
 10  1  1  0  0  0  0
 10  6  2  0  0  0  0
 11  2  1  0  0  0  0
 11  7  1  0  0  0  0
 12  3  1  0  0  0  0
 12  8  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14  4  1  0  0  0  0
 14  5  1  0  0  0  0
 14 11  1  0  0  0  0
 14 13  1  0  0  0  0
 15 12  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0035631

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CC=C(C)C(\C=C\C(C)=O)C1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C14H22O/c1-10-6-7-11(2)14(4,5)13(10)9-8-12(3)15/h6,8-9,11,13H,7H2,1-5H3/b9-8+

> <INCHI_KEY>
JZQOJFLIJNRDHK-CMDGGOBGSA-N

> <FORMULA>
C14H22O

> <MOLECULAR_WEIGHT>
206.3239

> <EXACT_MASS>
206.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
25.21769969479232

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3E)-4-(2,5,6,6-tetramethylcyclohex-2-en-1-yl)but-3-en-2-one

> <ALOGPS_LOGP>
4.37

> <JCHEM_LOGP>
3.606300591333333

> <ALOGPS_LOGS>
-3.94

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.830479446571594

> <JCHEM_PKA_STRONGEST_BASIC>
-4.9062405241313165

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
66.6373

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
2.36e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
α-iron

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0035631
     RDKit          3D
alpha-Irone
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.5967   -0.4363   -1.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6498    0.3440   -0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0936    1.3829    0.1445 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540   -0.0264   -0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4420    0.6983    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0430    0.4772    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6816    1.7147    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0228    2.9254   -0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9868    1.7064    0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7441    0.5548    0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473   -0.7387    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809   -1.7838    0.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6449   -0.6823    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9118   -0.5956   -1.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0088   -2.0210    0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0995    0.2369   -1.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1013   -1.2391   -1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4203   -0.8643   -0.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8226   -0.8994   -0.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8743    1.6010    0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853    0.4623    1.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2478    3.5954    0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5311    3.4223   -0.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.6488   -0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5422    2.5929    0.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7015    0.4987    0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0805    0.7833    1.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8680   -1.1245    1.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2751   -2.6385   -0.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4779   -1.3116   -0.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5833   -2.2012    0.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9842   -1.6524   -1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8951   -0.1333   -1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1207   -0.0521   -1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2087   -2.6248   -0.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666   -1.9228    1.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7084   -2.6967    1.1464 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
 11 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
  4 19  1  0
  5 20  1  0
  6 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 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      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.335   1.540   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.324   3.490   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.344   3.490   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -4.001   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000   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      -4.001   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   10                                                       
CONECT    7    6   11                                                       
CONECT    8    9   12                                                       
CONECT    9    8   13                                                       
CONECT   10    1    6   13                                                  
CONECT   11    2    7   14                                                  
CONECT   12    3    8   15                                                  
CONECT   13    9   10   14                                                  
CONECT   14    4    5   11   13                                             
CONECT   15   12                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0035631
HETATM    1  C1  UNL     1       4.597  -0.436  -1.235  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.650   0.344  -0.417  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.094   1.383   0.144  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.254  -0.026  -0.233  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.442   0.698   0.506  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.043   0.477   0.792  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.682   1.715   0.343  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.023   2.925  -0.163  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.987   1.706   0.407  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.744   0.555   0.892  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.047  -0.739   0.867  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.881  -1.784   0.165  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.645  -0.682   0.234  1.00  0.00           C  
HETATM   14  C13 UNL     1      -0.912  -0.596  -1.261  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.009  -2.021   0.569  1.00  0.00           C  
HETATM   16  H1  UNL     1       5.099   0.237  -1.963  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.101  -1.239  -1.819  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.420  -0.864  -0.595  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.823  -0.899  -0.689  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.874   1.601   0.979  1.00  0.00           H  
HETATM   21  H6  UNL     1      -0.085   0.462   1.913  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.248   3.595   0.688  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.531   3.422  -0.983  1.00  0.00           H  
HETATM   24  H9  UNL     1       1.016   2.649  -0.600  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.542   2.593   0.087  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.701   0.499   0.309  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.080   0.783   1.945  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.868  -1.125   1.907  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.275  -2.639  -0.209  1.00  0.00           H  
HETATM   30  H15 UNL     1      -3.478  -1.312  -0.651  1.00  0.00           H  
HETATM   31  H16 UNL     1      -3.583  -2.201   0.915  1.00  0.00           H  
HETATM   32  H17 UNL     1      -0.984  -1.652  -1.618  1.00  0.00           H  
HETATM   33  H18 UNL     1      -1.895  -0.133  -1.460  1.00  0.00           H  
HETATM   34  H19 UNL     1      -0.121  -0.052  -1.805  1.00  0.00           H  
HETATM   35  H20 UNL     1       0.209  -2.625  -0.351  1.00  0.00           H  
HETATM   36  H21 UNL     1       0.867  -1.923   1.244  1.00  0.00           H  
HETATM   37  H22 UNL     1      -0.708  -2.697   1.146  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    4
CONECT    4    5    5   19
CONECT    5    6   20
CONECT    6    7   13   21
CONECT    7    8    9    9
CONECT    8   22   23   24
CONECT    9   10   25
CONECT   10   11   26   27
CONECT   11   12   13   28
CONECT   12   29   30   31
CONECT   13   14   15
CONECT   14   32   33   34
CONECT   15   35   36   37
END

HMDB0035631
     RDKit          3D
alpha-Irone
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.5967   -0.4363   -1.2350 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6498    0.3440   -0.4166 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0936    1.3829    0.1445 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2540   -0.0264   -0.2329 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4420    0.6983    0.5062 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0430    0.4772    0.7917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6816    1.7147    0.3425 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0228    2.9254   -0.1630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9868    1.7064    0.4068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7441    0.5548    0.8918 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0473   -0.7387    0.8668 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8809   -1.7838    0.1649 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6449   -0.6823    0.2337 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9118   -0.5956   -1.2615 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0088   -2.0210    0.5690 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0995    0.2369   -1.9628 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1013   -1.2391   -1.8192 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4203   -0.8643   -0.5949 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8226   -0.8994   -0.6891 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8743    1.6010    0.9788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0853    0.4623    1.9133 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2478    3.5954    0.6884 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5311    3.4223   -0.9826 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0164    2.6488   -0.5998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5422    2.5929    0.0868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7015    0.4987    0.3092 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0805    0.7833    1.9446 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8680   -1.1245    1.9066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2751   -2.6385   -0.2089 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4779   -1.3116   -0.6508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5833   -2.2012    0.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9842   -1.6524   -1.6180 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8951   -0.1333   -1.4605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1207   -0.0521   -1.8048 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2087   -2.6248   -0.3505 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8666   -1.9228    1.2437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7084   -2.6967    1.1464 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
 11 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
  4 19  1  0
  5 20  1  0
  6 21  1  0
  8 22  1  0
  8 23  1  0
  8 24  1  0
  9 25  1  0
 10 26  1  0
 10 27  1  0
 11 28  1  0
 12 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
6-Methyl-alpha-ionone	ChEBI
alpha-Iron	ChEBI
Methyl alpha-ionone	ChEBI
Methyl-alpha-ionone	ChEBI
6-Methyl-a-ionone	Generator
6-Methyl-α-ionone	Generator
a-Iron	Generator
Α-iron	Generator
Methyl a-ionone	Generator
Methyl α-ionone	Generator
Methyl-a-ionone	Generator
Methyl-α-ionone	Generator
a-Irone	Generator
Α-irone	Generator
4-(2,5,6,6-Tetramethyl-2-cyclo-hexen-1-yl)-3-buten-2-one	HMDB
4-(2,5,6,6-Tetramethyl-2-cyclohexen-1-yl)-3-buten-2-one	HMDB
4-(2,5,6,6-Tetramethyl-2-cyclohexen-1-yl)-3-buten-2-one, 9ci	HMDB
4-(2,5,6,6-Tetramethylcyclohex-2-enyl)but-3-en-2-one	HMDB
6-Methyl ionone	HMDB
6-Methyl-alpha -ionone	HMDB
alpha -Irone	HMDB
alpha -Methyl-ionone	HMDB
alpha 6-Methyl--ionone	HMDB
alpha-Cyclocitrylidenebutanone	HMDB
alpha-Cyclocitrylidenemethyl ethyl ketone	HMDB
alpha-Inone, methyl- (6ci)	HMDB
cis-2,6-cis-(2(1),2(2))-alpha-Ionone	HMDB
FEMA 2597	HMDB
Ionone 6-methyl, alpha	HMDB
Irone	HMDB
Methyl-alpha -ionone	HMDB
Methyl-alpha-inone	HMDB

Chemical Formula

C₁₄H₂₂O

Average Molecular Weight

206.3239

Monoisotopic Molecular Weight

206.167065326

IUPAC Name

(3E)-4-(2,5,6,6-tetramethylcyclohex-2-en-1-yl)but-3-en-2-one

Traditional Name

α-iron

CAS Registry Number

79-69-6

SMILES

CC1CC=C(C)C(\C=C\C(C)=O)C1(C)C

InChI Identifier

InChI=1S/C14H22O/c1-10-6-7-11(2)14(4,5)13(10)9-8-12(3)15/h6,8-9,11,13H,7H2,1-5H3/b9-8+

InChI Key

JZQOJFLIJNRDHK-CMDGGOBGSA-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

enone (CHEBI:10284 )
methyl ketone (CHEBI:10284 )

Ontology

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0035631)

Source

Endogenous

Endogenous (HMDB: HMDB0035631)

Animal

Animal (HMDB: HMDB0035631)

Exogenous

Food

Food (HMDB: HMDB0035631)

Exogenous (HMDB: HMDB0035631)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0035631)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0035631)

Lipid metabolism pathway (HMDB: HMDB0035631)

Cellular process

Cell signaling (HMDB: HMDB0035631)

Biochemical process

Lipid transport (HMDB: HMDB0035631)

Role

Biological role

Energy source (HMDB: HMDB0035631)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0035631)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0035631)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	110.00 to 112.00 °C. @ 3.00 mm Hg	The Good Scents Company Information System
Water Solubility	110 mg/L @ 20 °C (exp)	The Good Scents Company Information System
LogP	4.354 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.024 g/L	ALOGPS
logP	4.37	ALOGPS
logP	3.61	ChemAxon
logS	-3.9	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	66.64 m³·mol⁻¹	ChemAxon
Polarizability	25.22 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]+	160.444	30932474
DeepCCS	[M-H]-	158.086	30932474
DeepCCS	[M-2H]-	191.002	30932474
DeepCCS	[M+Na]+	166.537	30932474
AllCCS	[M+H]+	146.6	32859911
AllCCS	[M+H-H2O]+	142.6	32859911
AllCCS	[M+NH4]+	150.2	32859911
AllCCS	[M+Na]+	151.3	32859911
AllCCS	[M-H]-	154.9	32859911
AllCCS	[M+Na-2H]-	155.8	32859911
AllCCS	[M+HCOO]-	156.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Irone	CC1CC=C(C)C(\C=C\C(C)=O)C1(C)C	1893.6	Standard polar	33892256
alpha-Irone	CC1CC=C(C)C(\C=C\C(C)=O)C1(C)C	1483.9	Standard non polar	33892256
alpha-Irone	CC1CC=C(C)C(\C=C\C(C)=O)C1(C)C	1530.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
alpha-Irone,1TMS,isomer #1	C=C(/C=C/C1C(C)=CCC(C)C1(C)C)O[Si](C)(C)C	1697.2	Semi standard non polar	33892256
alpha-Irone,1TMS,isomer #1	C=C(/C=C/C1C(C)=CCC(C)C1(C)C)O[Si](C)(C)C	1689.2	Standard non polar	33892256
alpha-Irone,1TBDMS,isomer #1	C=C(/C=C/C1C(C)=CCC(C)C1(C)C)O[Si](C)(C)C(C)(C)C	1942.2	Semi standard non polar	33892256
alpha-Irone,1TBDMS,isomer #1	C=C(/C=C/C1C(C)=CCC(C)C1(C)C)O[Si](C)(C)C(C)(C)C	1930.9	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Irone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-3900000000-b4a715b98f10ee9cec48	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Irone 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 - alpha-Irone 10V, Positive-QTOF	splash10-0a4r-0950000000-70fd0f0822b39f0c8143	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Irone 20V, Positive-QTOF	splash10-000b-4910000000-e34040151d7830394e0a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Irone 40V, Positive-QTOF	splash10-014i-9500000000-39043a12d53e0892753b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Irone 10V, Negative-QTOF	splash10-0a4i-0290000000-8c80db8fb62c55703146	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Irone 20V, Negative-QTOF	splash10-0a4i-1790000000-2fbdf8062ade1ea9e56b	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Irone 40V, Negative-QTOF	splash10-000i-2900000000-69279f9e831387c30def	2016-08-04	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Irone 10V, Negative-QTOF	splash10-0a4i-0090000000-3601d41603fac89c511d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Irone 20V, Negative-QTOF	splash10-08g1-0930000000-65aa652057f35fd0bd34	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Irone 40V, Negative-QTOF	splash10-0apj-2910000000-9d2cfc1547118383cb26	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Irone 10V, Positive-QTOF	splash10-053i-1920000000-ea38e53cb8217c61eb1a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Irone 20V, Positive-QTOF	splash10-05o9-3900000000-ab74961732052d20ebb8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Irone 40V, Positive-QTOF	splash10-052f-9400000000-6dc44e6945fdbed5ed98	2021-09-24	Wishart 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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Irone

METLIN ID

Not Available

PubChem Compound

5371002

PDB ID

Not Available

ChEBI ID

10284

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1006691

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 alpha-Irone (HMDB0035631)

MOL for HMDB0035631 (alpha-Irone)

3D MOL for HMDB0035631 (alpha-Irone)

3D SDF for HMDB0035631 (alpha-Irone)

3D-SDF for HMDB0035631 (alpha-Irone)

PDB for HMDB0035631 (alpha-Irone)

3D PDB for HMDB0035631 (alpha-Irone)

SMILES for HMDB0035631 (alpha-Irone)

INCHI for HMDB0035631 (alpha-Irone)

Structure for HMDB0035631 (alpha-Irone)

3D Structure for HMDB0035631 (alpha-Irone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra