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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-08 15:55:27 UTC

Update Date

2022-03-07 03:17:47 UTC

HMDB ID

HMDB0061831

Secondary Accession Numbers

HMDB61831

Metabolite Identification

Common Name

(Z)-alpha-Irone

Description

(Z)-alpha-Irone, also known as (Z)-a-irone, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units (Z)-alpha-Irone is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0061831
     RDKit          3D
(Z)-alpha-Irone
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.3465   -1.1067    0.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9904   -0.6116    0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9052   -0.4620   -0.9815 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0071   -0.3864    1.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8031    0.0338    1.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570    0.3425   -0.2933 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1855    1.7733   -0.3878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6547    2.8017   -1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410    2.1235    0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2084    1.1432    0.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1653   -0.2168    0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4407   -1.2326    1.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9656   -0.5330   -0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2312   -0.3420   -2.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554   -1.9842   -0.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5087   -0.8297    1.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1563   -0.6100    0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4486   -2.1827    0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2721   -0.5806    2.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1333    0.1680    1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9332    0.1592   -1.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.2166   -0.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    2.3414   -1.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0694    3.6421   -1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6459    3.1775    0.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2632    1.5462    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0542    1.1268    1.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0543   -0.3196   -0.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5412   -1.1376    1.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9228   -1.0087    2.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3192   -2.2751    0.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1256   -0.9199   -2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3873    0.7548   -2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3108   -0.6373   -2.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3051   -2.2202    0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -2.6095   -0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3333   -2.1444   -1.0858 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  6
  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 10081412312D          

 19 19  0  0  1  0            999 V2000
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    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
   -0.2822    1.6002    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8125    0.6817    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
   -1.4289    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
    0.7145   -0.4125    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
   -1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.0000    0.0000 C   0  0  2  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 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1434   -0.4125    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145   -1.2375    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    1.6500    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    0.4125    0.0000 H   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  1  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
 16  8  1  0  0  0  0
 17  9  1  0  0  0  0
 18 11  1  0  0  0  0
 13 19  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0061831

> <DATABASE_NAME>
hmdb

> <SMILES>
[H]\C(=C(/[H])[C@]1([H])C(C)=CCC([H])(C)C1(C)C)C(C)=O

> <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-/t11?,13-/m1/s1

> <INCHI_KEY>
JZQOJFLIJNRDHK-HWELFCKPSA-N

> <FORMULA>
C14H22O

> <MOLECULAR_WEIGHT>
206.3239

> <EXACT_MASS>
206.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
25.0545196180278

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(3Z)-4-[(1R)-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>
(3Z)-4-[(1R)-2,5,6,6-tetramethylcyclohex-2-en-1-yl]but-3-en-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0061831
     RDKit          3D
(Z)-alpha-Irone
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.3465   -1.1067    0.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9904   -0.6116    0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9052   -0.4620   -0.9815 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0071   -0.3864    1.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8031    0.0338    1.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570    0.3425   -0.2933 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1855    1.7733   -0.3878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6547    2.8017   -1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410    2.1235    0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2084    1.1432    0.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1653   -0.2168    0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4407   -1.2326    1.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9656   -0.5330   -0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2312   -0.3420   -2.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554   -1.9842   -0.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5087   -0.8297    1.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1563   -0.6100    0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4486   -2.1827    0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2721   -0.5806    2.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1333    0.1680    1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9332    0.1592   -1.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.2166   -0.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    2.3414   -1.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0694    3.6421   -1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6459    3.1775    0.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2632    1.5462    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0542    1.1268    1.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0543   -0.3196   -0.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5412   -1.1376    1.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9228   -1.0087    2.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3192   -2.2751    0.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1256   -0.9199   -2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3873    0.7548   -2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3108   -0.6373   -2.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3051   -2.2202    0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -2.6095   -0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3333   -2.1444   -1.0858 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  6
  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                                 08-OCT-14   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   08-OCT-14         0                                  
HETATM    1  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.334   2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.527   2.987   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.517   1.273   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       2.667  -0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -2.667   0.000   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -2.667   1.540   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.000  -0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0      -4.001   2.310   0.000  0.00  0.00           O+0
HETATM   16  H   UNK     0      -4.001  -0.770   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0      -1.334  -2.310   0.000  0.00  0.00           H+0
HETATM   18  H   UNK     0       2.667   3.080   0.000  0.00  0.00           H+0
HETATM   19  H   UNK     0      -1.334   0.770   0.000  0.00  0.00           H+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   16                                                  
CONECT    9    8   13   17                                                  
CONECT   10    1    6   13                                                  
CONECT   11    2    7   14   18                                             
CONECT   12    3    8   15                                                  
CONECT   13    9   10   14   19                                             
CONECT   14    4    5   11   13                                             
CONECT   15   12                                                            
CONECT   16    8                                                            
CONECT   17    9                                                            
CONECT   18   11                                                            
CONECT   19   13                                                            
MASTER        0    0    0    0    0    0    0    0   19    0   38    0
END

COMPND    HMDB0061831
HETATM    1  C1  UNL     1       4.346  -1.107   0.709  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.990  -0.612   0.239  1.00  0.00           C  
HETATM    3  O1  UNL     1       2.905  -0.462  -0.981  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.007  -0.386   1.244  1.00  0.00           C  
HETATM    5  C4  UNL     1       0.803   0.034   1.011  1.00  0.00           C  
HETATM    6  C5  UNL     1       0.257   0.342  -0.293  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.185   1.773  -0.388  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.655   2.802  -1.059  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.341   2.123   0.135  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.208   1.143   0.809  1.00  0.00           C  
HETATM   11  C10 UNL     1      -2.165  -0.217   0.203  1.00  0.00           C  
HETATM   12  C11 UNL     1      -2.441  -1.233   1.306  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.966  -0.533  -0.604  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.231  -0.342  -2.095  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.555  -1.984  -0.428  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.509  -0.830   1.770  1.00  0.00           H  
HETATM   17  H2  UNL     1       5.156  -0.610   0.129  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.449  -2.183   0.554  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.272  -0.581   2.325  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.133   0.168   1.901  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.933   0.159  -1.131  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.429   3.217  -0.354  1.00  0.00           H  
HETATM   23  H8  UNL     1       1.151   2.341  -1.953  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.069   3.642  -1.426  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.646   3.177   0.055  1.00  0.00           H  
HETATM   26  H11 UNL     1      -3.263   1.546   0.728  1.00  0.00           H  
HETATM   27  H12 UNL     1      -2.054   1.127   1.929  1.00  0.00           H  
HETATM   28  H13 UNL     1      -3.054  -0.320  -0.491  1.00  0.00           H  
HETATM   29  H14 UNL     1      -3.541  -1.138   1.544  1.00  0.00           H  
HETATM   30  H15 UNL     1      -1.923  -1.009   2.243  1.00  0.00           H  
HETATM   31  H16 UNL     1      -2.319  -2.275   0.951  1.00  0.00           H  
HETATM   32  H17 UNL     1      -2.126  -0.920  -2.420  1.00  0.00           H  
HETATM   33  H18 UNL     1      -1.387   0.755  -2.254  1.00  0.00           H  
HETATM   34  H19 UNL     1      -0.311  -0.637  -2.626  1.00  0.00           H  
HETATM   35  H20 UNL     1      -0.305  -2.220   0.633  1.00  0.00           H  
HETATM   36  H21 UNL     1      -1.377  -2.610  -0.827  1.00  0.00           H  
HETATM   37  H22 UNL     1       0.333  -2.144  -1.086  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

HMDB0061831
     RDKit          3D
(Z)-alpha-Irone
 37 37  0  0  0  0  0  0  0  0999 V2000
    4.3465   -1.1067    0.7088 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9904   -0.6116    0.2395 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9052   -0.4620   -0.9815 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0071   -0.3864    1.2440 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8031    0.0338    1.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2570    0.3425   -0.2933 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.1855    1.7733   -0.3878 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6547    2.8017   -1.0590 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3410    2.1235    0.1346 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2084    1.1432    0.8088 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1653   -0.2168    0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4407   -1.2326    1.3061 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9656   -0.5330   -0.6045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2312   -0.3420   -2.0948 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5554   -1.9842   -0.4276 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5087   -0.8297    1.7703 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1563   -0.6100    0.1289 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4486   -2.1827    0.5536 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2721   -0.5806    2.3250 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1333    0.1680    1.9012 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9332    0.1592   -1.1310 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    3.2166   -0.3543 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1514    2.3414   -1.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0694    3.6421   -1.4256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6459    3.1775    0.0547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2632    1.5462    0.7280 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0542    1.1268    1.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0543   -0.3196   -0.4914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5412   -1.1376    1.5438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9228   -1.0087    2.2426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3192   -2.2751    0.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1256   -0.9199   -2.4200 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3873    0.7548   -2.2539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3108   -0.6373   -2.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3051   -2.2202    0.6326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3766   -2.6095   -0.8271 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3333   -2.1444   -1.0858 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  6
  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
(Z)-a-Irone	Generator
(Z)-Α-irone	Generator

Chemical Formula

C₁₄H₂₂O

Average Molecular Weight

206.3239

Monoisotopic Molecular Weight

206.167065326

IUPAC Name

(3Z)-4-[(1R)-2,5,6,6-tetramethylcyclohex-2-en-1-yl]but-3-en-2-one

Traditional Name

(3Z)-4-[(1R)-2,5,6,6-tetramethylcyclohex-2-en-1-yl]but-3-en-2-one

CAS Registry Number

Not Available

SMILES

[H]\C(=C(/[H])[C@]1([H])C(C)=CCC([H])(C)C1(C)C)C(C)=O

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-/t11?,13-/m1/s1

InChI Key

JZQOJFLIJNRDHK-HWELFCKPSA-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

Non-excretory biofluid

Biofluid or Excreta

Saliva (PMID: 20809147)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	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	25.05 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]+	158.569	30932474
DeepCCS	[M-H]-	156.173	30932474
DeepCCS	[M-2H]-	190.331	30932474
DeepCCS	[M+Na]+	165.192	30932474
AllCCS	[M+H]+	147.1	32859911
AllCCS	[M+H-H2O]+	143.3	32859911
AllCCS	[M+NH4]+	150.7	32859911
AllCCS	[M+Na]+	151.8	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
(Z)-alpha-Irone	[H]\C(=C(/[H])[C@]1([H])C(C)=CCC([H])(C)C1(C)C)C(C)=O	1852.8	Standard polar	33892256
(Z)-alpha-Irone	[H]\C(=C(/[H])[C@]1([H])C(C)=CCC([H])(C)C1(C)C)C(C)=O	1468.0	Standard non polar	33892256
(Z)-alpha-Irone	[H]\C(=C(/[H])[C@]1([H])C(C)=CCC([H])(C)C1(C)C)C(C)=O	1434.8	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(Z)-alpha-Irone,1TMS,isomer #1	C=C(/C=C\[C@@H]1C(C)=CCC(C)C1(C)C)O[Si](C)(C)C	1692.2	Semi standard non polar	33892256
(Z)-alpha-Irone,1TMS,isomer #1	C=C(/C=C\[C@@H]1C(C)=CCC(C)C1(C)C)O[Si](C)(C)C	1696.5	Standard non polar	33892256
(Z)-alpha-Irone,1TMS,isomer #1	C=C(/C=C\[C@@H]1C(C)=CCC(C)C1(C)C)O[Si](C)(C)C	1787.4	Standard polar	33892256
(Z)-alpha-Irone,1TBDMS,isomer #1	C=C(/C=C\[C@@H]1C(C)=CCC(C)C1(C)C)O[Si](C)(C)C(C)(C)C	1940.1	Semi standard non polar	33892256
(Z)-alpha-Irone,1TBDMS,isomer #1	C=C(/C=C\[C@@H]1C(C)=CCC(C)C1(C)C)O[Si](C)(C)C(C)(C)C	1935.6	Standard non polar	33892256
(Z)-alpha-Irone,1TBDMS,isomer #1	C=C(/C=C\[C@@H]1C(C)=CCC(C)C1(C)C)O[Si](C)(C)C(C)(C)C	1938.8	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-alpha-Irone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-3900000000-9f4f8e34a1ee56baab10	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (Z)-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 - (Z)-alpha-Irone 10V, Positive-QTOF	splash10-0a4r-0950000000-aec8b0ec94473f9c5ea0	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Irone 20V, Positive-QTOF	splash10-053j-5910000000-a74c9e71541561f7a7d9	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Irone 40V, Positive-QTOF	splash10-015i-9400000000-773d22584c2e905f81d8	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Irone 10V, Negative-QTOF	splash10-0a4i-0290000000-e1b45e096e5b021b1a15	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Irone 20V, Negative-QTOF	splash10-0a4i-0590000000-3c8d8aa87fba256bde72	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Irone 40V, Negative-QTOF	splash10-000i-2900000000-7956c55daf1fbade4761	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Irone 10V, Positive-QTOF	splash10-05ai-2920000000-67db384a7786a9920ab3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Irone 20V, Positive-QTOF	splash10-001i-6900000000-827197fb96300d4789f1	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Irone 40V, Positive-QTOF	splash10-055f-9400000000-cf5896e468ccacf37177	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Irone 10V, Negative-QTOF	splash10-0a4i-0090000000-2d8ac504a1490d38e7ad	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Irone 20V, Negative-QTOF	splash10-000i-0940000000-5293c8f859fd8b7cea4d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (Z)-alpha-Irone 40V, Negative-QTOF	splash10-07i2-0910000000-5673c009b9d9c7e1bab5	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	20809147	details

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6431140

PDB ID

Not Available

ChEBI ID

88618

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (Z)-alpha-Irone (HMDB0061831)

MOL for HMDB0061831 ((Z)-alpha-Irone)

3D MOL for HMDB0061831 ((Z)-alpha-Irone)

3D SDF for HMDB0061831 ((Z)-alpha-Irone)

3D-SDF for HMDB0061831 ((Z)-alpha-Irone)

PDB for HMDB0061831 ((Z)-alpha-Irone)

3D PDB for HMDB0061831 ((Z)-alpha-Irone)

SMILES for HMDB0061831 ((Z)-alpha-Irone)

INCHI for HMDB0061831 ((Z)-alpha-Irone)

Structure for HMDB0061831 ((Z)-alpha-Irone)

3D Structure for HMDB0061831 ((Z)-alpha-Irone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra