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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:59:50 UTC

Update Date

2023-02-21 17:25:29 UTC

HMDB ID

HMDB0036821

Secondary Accession Numbers

HMDB36821

Metabolite Identification

Common Name

3-Hydroxy-beta-ionone

Description

3-Hydroxy-beta-ionone (CAS: 116296-75-4), also known as apo-9-zeaxanthinone (CAS: 50281-38-4), belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. 3-Hydroxy-beta-ionone has been detected, but not quantified in, several different foods, such as green bell peppers, red bell peppers, pepper (C. annuum), Italian sweet red peppers, and orange bell peppers. This could make 3-hydroxy-beta-ionone a potential biomarker for the consumption of these foods. 3-Hydroxy-beta-ionone is found in pulses. 3-Hydroxy-beta-ionone is isolated from Phaseolus vulgaris (kidney bean).

Structure

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

HMDB0036821
     RDKit          3D
3-Hydroxy-beta-ionone
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.5551   -0.9805   -0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5403    0.0823   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9248    1.2748   -0.4185 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316   -0.2656   -0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2438    0.6827   -0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.4899    0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9830    1.5365    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3100    2.8854    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580    1.4762    0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9550    0.2371   -0.1404 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6874    0.3928   -1.4957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2274   -0.9246    0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7501   -0.9038    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4747   -1.6212   -1.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1109   -1.7075    1.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927   -1.3566   -1.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550   -1.7990    0.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5729   -0.6048   -0.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7925   -1.2845   -0.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6025    1.7257   -0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1148    3.6438    0.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    3.0629    1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762    3.0108   -0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8725    2.4096    0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321    1.5094    1.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0219    0.1333    0.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4881    0.8607   -1.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6302   -1.8957    0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048   -0.8832    1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067   -2.5962   -0.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1041   -0.9724   -1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4484   -1.8485   -1.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6452   -1.1161    1.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2804   -2.6941    1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9056   -1.9597    2.0914 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 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
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  6
 11 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
M  END


  Mrv1652307072017432D          

 15 15  0  0  0  0            999 V2000
   -1.7862    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7862   -0.8250    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.0717   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572   -0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3572    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0717    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5006    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5006   -1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3572   -1.2374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7862    1.2374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5878    1.0561    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5455    1.0462    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0717    0.4125    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
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  2 10  1  1  0  0  0
  4 11  1  0  0  0  0
  8 12  2  0  0  0  0
 15 13  1  0  0  0  0
 15 14  1  0  0  0  0
  5 15  1  0  0  0  0
 15  1  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036821

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)\C=C\C1=C(C)C[C@@H](O)CC1(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-6,11,15H,7-8H2,1-4H3/b6-5+/t11-/m1/s1

> <INCHI_KEY>
HFRZSVYKDDZRQY-MVIFTORASA-N

> <FORMULA>
C13H20O2

> <MOLECULAR_WEIGHT>
208.2967

> <EXACT_MASS>
208.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
35

> <JCHEM_AVERAGE_POLARIZABILITY>
24.048416947252342

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.10

> <JCHEM_LOGP>
1.8889051433333337

> <ALOGPS_LOGS>
-2.46

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.705448550238387

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.907213401199783

> <JCHEM_PKA_STRONGEST_BASIC>
-1.0896768165158917

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
63.49159999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
2

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.26e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(3R)-hydroxy-β-ionone

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036821
     RDKit          3D
3-Hydroxy-beta-ionone
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.5551   -0.9805   -0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5403    0.0823   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9248    1.2748   -0.4185 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316   -0.2656   -0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2438    0.6827   -0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.4899    0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9830    1.5365    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3100    2.8854    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580    1.4762    0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9550    0.2371   -0.1404 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6874    0.3928   -1.4957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2274   -0.9246    0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7501   -0.9038    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4747   -1.6212   -1.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1109   -1.7075    1.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927   -1.3566   -1.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550   -1.7990    0.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5729   -0.6048   -0.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7925   -1.2845   -0.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6025    1.7257   -0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1148    3.6438    0.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    3.0629    1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762    3.0108   -0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8725    2.4096    0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321    1.5094    1.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0219    0.1333    0.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4881    0.8607   -1.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6302   -1.8957    0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048   -0.8832    1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067   -2.5962   -0.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1041   -0.9724   -1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4484   -1.8485   -1.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6452   -1.1161    1.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2804   -2.6941    1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9056   -1.9597    2.0914 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 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
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  6
 11 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
M  END

HEADER    PROTEIN                                 07-JUL-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   07-JUL-20         0                                  
HETATM    1  C   UNK     0      -3.334   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -3.334  -1.540   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.001  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -0.667  -1.540   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.667   0.770   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.001   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.334   0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.668   0.000   0.000  0.00  0.00           C+0
HETATM   10  O   UNK     0      -4.668  -2.310   0.000  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.667  -2.310   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.334   2.310   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.964   1.971   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -1.018   1.953   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.001   0.770   0.000  0.00  0.00           C+0
CONECT    1    2   15                                                       
CONECT    2    1    3   10                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   11                                                  
CONECT    5    4    6   15                                                  
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9   12                                                  
CONECT    9    8                                                            
CONECT   10    2                                                            
CONECT   11    4                                                            
CONECT   12    8                                                            
CONECT   13   15                                                            
CONECT   14   15                                                            
CONECT   15   13   14    5    1                                             
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0036821
HETATM    1  C1  UNL     1       4.555  -0.981  -0.566  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.540   0.082  -0.386  1.00  0.00           C  
HETATM    3  O1  UNL     1       3.925   1.275  -0.419  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.132  -0.266  -0.178  1.00  0.00           C  
HETATM    5  C4  UNL     1       1.244   0.683  -0.021  1.00  0.00           C  
HETATM    6  C5  UNL     1      -0.191   0.490   0.195  1.00  0.00           C  
HETATM    7  C6  UNL     1      -0.983   1.537   0.340  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.310   2.885   0.267  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.458   1.476   0.566  1.00  0.00           C  
HETATM   10  C9  UNL     1      -2.955   0.237  -0.140  1.00  0.00           C  
HETATM   11  O2  UNL     1      -2.687   0.393  -1.496  1.00  0.00           O  
HETATM   12  C10 UNL     1      -2.227  -0.925   0.460  1.00  0.00           C  
HETATM   13  C11 UNL     1      -0.750  -0.904   0.249  1.00  0.00           C  
HETATM   14  C12 UNL     1      -0.475  -1.621  -1.087  1.00  0.00           C  
HETATM   15  C13 UNL     1      -0.111  -1.708   1.343  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.493  -1.357  -1.619  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.355  -1.799   0.161  1.00  0.00           H  
HETATM   18  H3  UNL     1       5.573  -0.605  -0.425  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.793  -1.284  -0.149  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.603   1.726  -0.052  1.00  0.00           H  
HETATM   21  H6  UNL     1      -1.115   3.644   0.295  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.356   3.063   1.109  1.00  0.00           H  
HETATM   23  H8  UNL     1       0.176   3.011  -0.734  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.873   2.410   0.094  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.732   1.509   1.624  1.00  0.00           H  
HETATM   26  H11 UNL     1      -4.022   0.133   0.087  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.488   0.861  -1.880  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.630  -1.896   0.104  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.405  -0.883   1.567  1.00  0.00           H  
HETATM   30  H15 UNL     1      -0.007  -2.596  -0.944  1.00  0.00           H  
HETATM   31  H16 UNL     1       0.104  -0.972  -1.773  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.448  -1.848  -1.610  1.00  0.00           H  
HETATM   33  H18 UNL     1       0.645  -1.116   1.912  1.00  0.00           H  
HETATM   34  H19 UNL     1       0.280  -2.694   1.015  1.00  0.00           H  
HETATM   35  H20 UNL     1      -0.906  -1.960   2.091  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    7   13
CONECT    7    8    9
CONECT    8   21   22   23
CONECT    9   10   24   25
CONECT   10   11   12   26
CONECT   11   27
CONECT   12   13   28   29
CONECT   13   14   15
CONECT   14   30   31   32
CONECT   15   33   34   35
END

HMDB0036821
     RDKit          3D
3-Hydroxy-beta-ionone
 35 35  0  0  0  0  0  0  0  0999 V2000
    4.5551   -0.9805   -0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5403    0.0823   -0.3864 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9248    1.2748   -0.4185 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1316   -0.2656   -0.1783 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2438    0.6827   -0.0207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1914    0.4899    0.1949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9830    1.5365    0.3400 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3100    2.8854    0.2673 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4580    1.4762    0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9550    0.2371   -0.1404 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.6874    0.3928   -1.4957 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2274   -0.9246    0.4599 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7501   -0.9038    0.2487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4747   -1.6212   -1.0866 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1109   -1.7075    1.3429 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4927   -1.3566   -1.6192 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3550   -1.7990    0.1609 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5729   -0.6048   -0.4253 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7925   -1.2845   -0.1490 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6025    1.7257   -0.0519 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1148    3.6438    0.2946 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3558    3.0629    1.1094 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1762    3.0108   -0.7338 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8725    2.4096    0.0945 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7321    1.5094    1.6239 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0219    0.1333    0.0871 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4881    0.8607   -1.8803 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6302   -1.8957    0.1041 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4048   -0.8832    1.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0067   -2.5962   -0.9444 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1041   -0.9724   -1.7732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4484   -1.8485   -1.6101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6452   -1.1161    1.9123 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2804   -2.6941    1.0148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9056   -1.9597    2.0914 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  2  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 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
  8 21  1  0
  8 22  1  0
  8 23  1  0
  9 24  1  0
  9 25  1  0
 10 26  1  6
 11 27  1  0
 12 28  1  0
 12 29  1  0
 14 30  1  0
 14 31  1  0
 14 32  1  0
 15 33  1  0
 15 34  1  0
 15 35  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
3-Hydroxy-b-ionone	Generator
3-Hydroxy-β-ionone	Generator
(3E)-4-(4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl)-3-buten-2-one	HMDB
(3E)-4-[(4R)-4-Hydroxy-2,6,6-trimethyl-1-cyclohexen-1-yl]-3-buten-2-one	HMDB
(3R)-3-Hydroxy-beta-ionone	HMDB
(3R)-3-Hydroxy-β-ionone	HMDB
(R)-(-)-3-Hydroxy-beta-ionone	HMDB
(R)-(-)-3-Hydroxy-β-ionone	HMDB
(R)-3-Hydroxy-beta-ionone	HMDB
(R)-3-Hydroxy-β-ionone	HMDB
3beta-Hydroxymegastigma-5,7-dien-9-one	HMDB
3Β-hydroxymegastigma-5,7-dien-9-one	HMDB
Apo-9-zeaxanthinone	HMDB
3-Hydroxy-beta-ionone	HMDB

Chemical Formula

C₁₃H₂₀O₂

Average Molecular Weight

208.2967

Monoisotopic Molecular Weight

208.146329884

IUPAC Name

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

Traditional Name

(3R)-hydroxy-β-ionone

CAS Registry Number

50281-38-4

SMILES

CC(=O)\C=C\C1=C(C)C[C@@H](O)CC1(C)C

InChI Identifier

InChI=1S/C13H20O2/c1-9-7-11(15)8-13(3,4)12(9)6-5-10(2)14/h5-6,11,15H,7-8H2,1-4H3/b6-5+/t11-/m1/s1

InChI Key

HFRZSVYKDDZRQY-MVIFTORASA-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

Sesquiterpenoid
Megastigmane sesquiterpenoid
Cyclofarsesane sesquiterpenoid
Ionone derivative
Acryloyl-group
Enone
Alpha,beta-unsaturated ketone
Secondary alcohol
Ketone
Organic oxygen compound
Organooxygen compound
Alcohol
Carbonyl group
Organic oxide
Hydrocarbon derivative
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

apo carotenoid monoterpenoid (CHEBI:53173 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036821)

Source

Endogenous

Endogenous (HMDB: HMDB0036821)

Plant

Fabaceae (HMDB: HMDB0036821)

Animal

Animal (HMDB: HMDB0036821)

Exogenous

Food

Food (HMDB: HMDB0036821)

Pulse

Bean

Yellow wax bean (FooDB: FOOD00882)
Green bean (FooDB: FOOD00883)

Pulses (FooDB: FOOD00867)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036821)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036821)

Lipid metabolism pathway (HMDB: HMDB0036821)

Cellular process

Cell signaling (HMDB: HMDB0036821)

Biochemical process

Lipid transport (HMDB: HMDB0036821)

Role

Biological role

Energy source (HMDB: HMDB0036821)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036821)

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	0.73 g/L	ALOGPS
logP	2.1	ALOGPS
logP	1.89	ChemAxon
logS	-2.5	ALOGPS
pKa (Strongest Acidic)	18.91	ChemAxon
pKa (Strongest Basic)	-1.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	2	ChemAxon
Refractivity	63.49 m³·mol⁻¹	ChemAxon
Polarizability	24.05 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]+	158.571	30932474
DeepCCS	[M-H]-	156.176	30932474
DeepCCS	[M-2H]-	189.203	30932474
DeepCCS	[M+Na]+	164.484	30932474
AllCCS	[M+H]+	149.0	32859911
AllCCS	[M+H-H2O]+	145.1	32859911
AllCCS	[M+NH4]+	152.6	32859911
AllCCS	[M+Na]+	153.7	32859911
AllCCS	[M-H]-	153.6	32859911
AllCCS	[M+Na-2H]-	154.4	32859911
AllCCS	[M+HCOO]-	155.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-beta-ionone	CC(=O)\C=C\C1=C(C)C[C@@H](O)CC1(C)C	2570.5	Standard polar	33892256
3-Hydroxy-beta-ionone	CC(=O)\C=C\C1=C(C)C[C@@H](O)CC1(C)C	1621.0	Standard non polar	33892256
3-Hydroxy-beta-ionone	CC(=O)\C=C\C1=C(C)C[C@@H](O)CC1(C)C	1683.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
3-Hydroxy-beta-ionone,1TMS,isomer #1	CC(=O)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C)CC1(C)C	1773.8	Semi standard non polar	33892256
3-Hydroxy-beta-ionone,1TMS,isomer #2	C=C(/C=C/C1=C(C)C[C@@H](O)CC1(C)C)O[Si](C)(C)C	1824.9	Semi standard non polar	33892256
3-Hydroxy-beta-ionone,2TMS,isomer #1	C=C(/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C)CC1(C)C)O[Si](C)(C)C	1846.5	Semi standard non polar	33892256
3-Hydroxy-beta-ionone,2TMS,isomer #1	C=C(/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C)CC1(C)C)O[Si](C)(C)C	1942.2	Standard non polar	33892256
3-Hydroxy-beta-ionone,1TBDMS,isomer #1	CC(=O)/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C	2000.0	Semi standard non polar	33892256
3-Hydroxy-beta-ionone,1TBDMS,isomer #2	C=C(/C=C/C1=C(C)C[C@@H](O)CC1(C)C)O[Si](C)(C)C(C)(C)C	2065.8	Semi standard non polar	33892256
3-Hydroxy-beta-ionone,2TBDMS,isomer #1	C=C(/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C)O[Si](C)(C)C(C)(C)C	2313.1	Semi standard non polar	33892256
3-Hydroxy-beta-ionone,2TBDMS,isomer #1	C=C(/C=C/C1=C(C)C[C@@H](O[Si](C)(C)C(C)(C)C)CC1(C)C)O[Si](C)(C)C(C)(C)C	2438.6	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-beta-ionone GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 3-Hydroxy-beta-ionone 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 - 3-Hydroxy-beta-ionone 10V, Positive-QTOF	splash10-052f-0920000000-ca4bc2d8536a477454bd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 20V, Positive-QTOF	splash10-006x-1910000000-0800f9d35f89acbe6784	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 40V, Positive-QTOF	splash10-0kft-6900000000-561c8ee7b8326d943c55	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 10V, Negative-QTOF	splash10-0a4i-0390000000-4dfd440e0b9531f8a757	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 20V, Negative-QTOF	splash10-0a4r-1960000000-fd1b133f482bc7573abe	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 40V, Negative-QTOF	splash10-01ox-2900000000-04eff6259412f3590daf	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 10V, Negative-QTOF	splash10-0a4i-0090000000-43a9bdbf7663e467c30d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 20V, Negative-QTOF	splash10-0a4s-0940000000-e8333249a633e6a768b9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 40V, Negative-QTOF	splash10-0002-1900000000-31fb706dd6e842a6860a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 10V, Positive-QTOF	splash10-0a4r-1930000000-362c8ff12dca214674b5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 20V, Positive-QTOF	splash10-0abc-4900000000-3c361104d4dd0ac028bd	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 3-Hydroxy-beta-ionone 40V, Positive-QTOF	splash10-0006-9800000000-626f2e38ffe2cc811bbe	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+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

Cytoplasm
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

FDB001764

KNApSAcK ID

C00022191

Chemspider ID

9302625

KEGG Compound ID

Not Available

BioCyc ID

CPD-7200

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

11127505

PDB ID

Not Available

ChEBI ID

53173

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 ]
(). 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 3-Hydroxy-beta-ionone (HMDB0036821)

MOL for HMDB0036821 (3-Hydroxy-beta-ionone)

3D MOL for HMDB0036821 (3-Hydroxy-beta-ionone)

3D SDF for HMDB0036821 (3-Hydroxy-beta-ionone)

3D-SDF for HMDB0036821 (3-Hydroxy-beta-ionone)

PDB for HMDB0036821 (3-Hydroxy-beta-ionone)

3D PDB for HMDB0036821 (3-Hydroxy-beta-ionone)

SMILES for HMDB0036821 (3-Hydroxy-beta-ionone)

INCHI for HMDB0036821 (3-Hydroxy-beta-ionone)

Structure for HMDB0036821 (3-Hydroxy-beta-ionone)

3D Structure for HMDB0036821 (3-Hydroxy-beta-ionone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra