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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:44:05 UTC

Update Date

2022-03-07 02:53:55 UTC

HMDB ID

HMDB0033960

Secondary Accession Numbers

HMDB33960

Metabolite Identification

Common Name

Curcumenol

Description

Curcumenol belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively. Curcumenol is an extremely weak basic (essentially neutral) compound (based on its pKa).

Structure

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

HMDB0033960
     RDKit          3D
Curcumenol
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.2294    2.8843    0.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8818    1.6876   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1734    1.6908   -1.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8057    0.3938   -1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5881    0.4643   -2.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1481   -0.6325   -1.5359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7123   -0.7014   -0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4058   -0.6203    0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5226   -0.0883   -0.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8073   -0.0701    0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3163   -0.6035    1.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7578    0.4932   -0.8552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5779   -1.8622   -0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5743   -2.2065   -1.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3520   -1.3637    1.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3323    0.1605    1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6830    0.4587   -0.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4274    3.2003    1.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4056    3.7213   -0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1397    2.7516    1.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6052    2.6260   -1.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5478    1.3833   -2.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6558   -1.6438    1.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1899    0.0722    1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864   -1.7242    1.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4077   -0.4471    1.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7907   -0.1883    2.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9166   -0.2931   -1.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7023    0.7226   -0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    1.4162   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9923   -2.7682    0.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1209   -2.3527   -2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4330   -1.5019   -1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0237   -3.1974   -0.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3570   -1.7764    1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7403   -1.6365    2.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8501    0.6285    2.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4141    0.4689    1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3651    0.4544   -1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
  9  4  1  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
M  END


  Mrv0541 02241208342D          

 17 19  0  0  0  0            999 V2000
    1.6619    0.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3115   -0.0875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7489   -0.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2245   -1.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249   -1.1364    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5249   -0.2616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2616   -0.3498    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3497    0.6108    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5238    0.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4867    1.9240    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6989    1.5737    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0865    2.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5238   -2.1863    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3486   -1.3996    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9612   -0.7860    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9612    0.0864    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7489    0.2616    0.0000 O   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
  2  6  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  5 14  1  0  0  0  0
  6  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7 16  1  0  0  0  0
  8  9  1  0  0  0  0
  9 11  2  0  0  0  0
  9 16  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  2  0  0  0  0
 15 16  1  0  0  0  0
 16 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033960

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1CCC2C(C)=CC3(O)OC12CC3=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h7,11-12,16H,5-6,8H2,1-4H3

> <INCHI_KEY>
ISFMXVMWEWLJGJ-UHFFFAOYSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.334

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.219032823604312

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol

> <ALOGPS_LOGP>
2.52

> <JCHEM_LOGP>
3.1425060316666666

> <ALOGPS_LOGS>
-2.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.085590991152896

> <JCHEM_PKA_STRONGEST_BASIC>
-4.435632702004688

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
69.17859999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.71e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0033960
     RDKit          3D
Curcumenol
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.2294    2.8843    0.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8818    1.6876   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1734    1.6908   -1.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8057    0.3938   -1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5881    0.4643   -2.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1481   -0.6325   -1.5359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7123   -0.7014   -0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4058   -0.6203    0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5226   -0.0883   -0.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8073   -0.0701    0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3163   -0.6035    1.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7578    0.4932   -0.8552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5779   -1.8622   -0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5743   -2.2065   -1.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3520   -1.3637    1.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3323    0.1605    1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6830    0.4587   -0.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4274    3.2003    1.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4056    3.7213   -0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1397    2.7516    1.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6052    2.6260   -1.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5478    1.3833   -2.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6558   -1.6438    1.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1899    0.0722    1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864   -1.7242    1.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4077   -0.4471    1.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7907   -0.1883    2.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9166   -0.2931   -1.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7023    0.7226   -0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    1.4162   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9923   -2.7682    0.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1209   -2.3527   -2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4330   -1.5019   -1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0237   -3.1974   -0.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3570   -1.7764    1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7403   -1.6365    2.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8501    0.6285    2.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4141    0.4689    1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3651    0.4544   -1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
  9  4  1  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       3.102   1.140   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.448  -0.163   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.265  -1.467   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.286  -2.613   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.980  -2.121   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.980  -0.488   0.000  0.00  0.00           C+0
HETATM    7  O   UNK     0      -0.488  -0.653   0.000  0.00  0.00           O+0
HETATM    8  C   UNK     0       0.653   1.140   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -0.978   1.467   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.775   3.592   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.305   2.938   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.161   4.081   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -0.978  -4.081   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.651  -2.613   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.794  -1.467   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -1.794   0.161   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0      -3.265   0.488   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3    6                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6   14                                                  
CONECT    6    2    5    7    8                                             
CONECT    7    6   16                                                       
CONECT    8    6    9                                                       
CONECT    9    8   11   16                                                  
CONECT   10   11                                                            
CONECT   11    9   10   12                                                  
CONECT   12   11                                                            
CONECT   13   14                                                            
CONECT   14    5   13   15                                                  
CONECT   15   14   16                                                       
CONECT   16    7    9   15   17                                             
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0033960
HETATM    1  C1  UNL     1      -1.229   2.884   0.560  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.882   1.688  -0.222  1.00  0.00           C  
HETATM    3  C3  UNL     1       0.173   1.691  -1.010  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.806   0.394  -1.378  1.00  0.00           C  
HETATM    5  O1  UNL     1       1.588   0.464  -2.496  1.00  0.00           O  
HETATM    6  O2  UNL     1      -0.148  -0.632  -1.536  1.00  0.00           O  
HETATM    7  C5  UNL     1      -0.712  -0.701  -0.300  1.00  0.00           C  
HETATM    8  C6  UNL     1       0.406  -0.620   0.710  1.00  0.00           C  
HETATM    9  C7  UNL     1       1.523  -0.088  -0.160  1.00  0.00           C  
HETATM   10  C8  UNL     1       2.807  -0.070   0.121  1.00  0.00           C  
HETATM   11  C9  UNL     1       3.316  -0.604   1.398  1.00  0.00           C  
HETATM   12  C10 UNL     1       3.758   0.493  -0.855  1.00  0.00           C  
HETATM   13  C11 UNL     1      -1.578  -1.862  -0.004  1.00  0.00           C  
HETATM   14  C12 UNL     1      -2.574  -2.207  -1.057  1.00  0.00           C  
HETATM   15  C13 UNL     1      -2.352  -1.364   1.224  1.00  0.00           C  
HETATM   16  C14 UNL     1      -2.332   0.160   1.135  1.00  0.00           C  
HETATM   17  C15 UNL     1      -1.683   0.459  -0.161  1.00  0.00           C  
HETATM   18  H1  UNL     1      -0.427   3.200   1.258  1.00  0.00           H  
HETATM   19  H2  UNL     1      -1.406   3.721  -0.156  1.00  0.00           H  
HETATM   20  H3  UNL     1      -2.140   2.752   1.166  1.00  0.00           H  
HETATM   21  H4  UNL     1       0.605   2.626  -1.405  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.548   1.383  -2.896  1.00  0.00           H  
HETATM   23  H6  UNL     1       0.656  -1.644   1.017  1.00  0.00           H  
HETATM   24  H7  UNL     1       0.190   0.072   1.533  1.00  0.00           H  
HETATM   25  H8  UNL     1       3.186  -1.724   1.347  1.00  0.00           H  
HETATM   26  H9  UNL     1       4.408  -0.447   1.497  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.791  -0.188   2.284  1.00  0.00           H  
HETATM   28  H11 UNL     1       3.917  -0.293  -1.637  1.00  0.00           H  
HETATM   29  H12 UNL     1       4.702   0.723  -0.355  1.00  0.00           H  
HETATM   30  H13 UNL     1       3.381   1.416  -1.343  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.992  -2.768   0.244  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.121  -2.353  -2.059  1.00  0.00           H  
HETATM   33  H16 UNL     1      -3.433  -1.502  -1.094  1.00  0.00           H  
HETATM   34  H17 UNL     1      -3.024  -3.197  -0.780  1.00  0.00           H  
HETATM   35  H18 UNL     1      -3.357  -1.776   1.265  1.00  0.00           H  
HETATM   36  H19 UNL     1      -1.740  -1.636   2.114  1.00  0.00           H  
HETATM   37  H20 UNL     1      -1.850   0.629   2.001  1.00  0.00           H  
HETATM   38  H21 UNL     1      -3.414   0.469   1.063  1.00  0.00           H  
HETATM   39  H22 UNL     1      -2.365   0.454  -1.031  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   17
CONECT    3    4   21
CONECT    4    5    6    9
CONECT    5   22
CONECT    6    7
CONECT    7    8   13   17
CONECT    8    9   23   24
CONECT    9   10   10
CONECT   10   11   12
CONECT   11   25   26   27
CONECT   12   28   29   30
CONECT   13   14   15   31
CONECT   14   32   33   34
CONECT   15   16   35   36
CONECT   16   17   37   38
CONECT   17   39
END

HMDB0033960
     RDKit          3D
Curcumenol
 39 41  0  0  0  0  0  0  0  0999 V2000
   -1.2294    2.8843    0.5600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8818    1.6876   -0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1734    1.6908   -1.0096 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8057    0.3938   -1.3785 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5881    0.4643   -2.4956 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1481   -0.6325   -1.5359 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7123   -0.7014   -0.3003 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4058   -0.6203    0.7100 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5226   -0.0883   -0.1602 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8073   -0.0701    0.1212 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3163   -0.6035    1.3981 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7578    0.4932   -0.8552 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5779   -1.8622   -0.0041 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5743   -2.2065   -1.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3520   -1.3637    1.2242 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3323    0.1605    1.1351 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6830    0.4587   -0.1610 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4274    3.2003    1.2576 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4056    3.7213   -0.1564 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1397    2.7516    1.1658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6052    2.6260   -1.4055 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5478    1.3833   -2.8964 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6558   -1.6438    1.0168 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1899    0.0722    1.5327 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1864   -1.7242    1.3473 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4077   -0.4471    1.4974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7907   -0.1883    2.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9166   -0.2931   -1.6366 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7023    0.7226   -0.3555 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3810    1.4162   -1.3426 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9923   -2.7682    0.2440 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1209   -2.3527   -2.0587 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4330   -1.5019   -1.0943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0237   -3.1974   -0.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3570   -1.7764    1.2648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7403   -1.6365    2.1143 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8501    0.6285    2.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4141    0.4689    1.0628 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3651    0.4544   -1.0308 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  2  3
 10 11  1  0
 10 12  1  0
  7 13  1  0
 13 14  1  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 17  2  1  0
  9  4  1  0
 17  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  5 22  1  0
  8 23  1  0
  8 24  1  0
 11 25  1  0
 11 26  1  0
 11 27  1  0
 12 28  1  0
 12 29  1  0
 12 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
 17 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₂O₂

Average Molecular Weight

234.334

Monoisotopic Molecular Weight

234.161979948

IUPAC Name

2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol

Traditional Name

2,6-dimethyl-9-(propan-2-ylidene)-11-oxatricyclo[6.2.1.0¹,⁵]undec-6-en-8-ol

CAS Registry Number

19431-84-6

SMILES

CC1CCC2C(C)=CC3(O)OC12CC3=C(C)C

InChI Identifier

InChI=1S/C15H22O2/c1-9(2)13-8-14-11(4)5-6-12(14)10(3)7-15(13,16)17-14/h7,11-12,16H,5-6,8H2,1-4H3

InChI Key

ISFMXVMWEWLJGJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as guaianes. These are sesquiterpenoids with a structure based on the guaiane skeleton. Guaiane is a bicyclic compound consisting of a decahydroazulene moiety, substituted with two methyl groups and a 1-methylethyl group at the 1-, 4-, and 7-position, respectively.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Guaianes

Alternative Parents

Substituents

Guaiane sesquiterpenoid
Pyran
Tetrahydrofuran
Hemiacetal
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

sesquiterpenoid (CHEBI:80811 )

Ontology

Cellular substructure

Membrane (HMDB: HMDB0033960)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033960)

Source

Endogenous

Endogenous (HMDB: HMDB0033960)

Animal

Animal (HMDB: HMDB0033960)

Exogenous

Food

Food (HMDB: HMDB0033960)

Herb and spice

Spice

Turmeric (FooDB: FOOD00068)

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0033960)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0033960)

Cellular process

Cell signaling (HMDB: HMDB0033960)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0033960)

Role

Biological role

Nutrient

Nutrient (HMDB: HMDB0033960)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	118.5 - 119.5 °C	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	0.37 g/L	ALOGPS
logP	2.52	ALOGPS
logP	3.14	ChemAxon
logS	-2.8	ALOGPS
pKa (Strongest Acidic)	11.09	ChemAxon
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	69.18 m³·mol⁻¹	ChemAxon
Polarizability	27.22 Å³	ChemAxon
Number of Rings	3	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
DarkChem	[M+H]+	155.551	31661259
DarkChem	[M-H]-	153.018	31661259
DeepCCS	[M-2H]-	190.189	30932474
DeepCCS	[M+Na]+	165.755	30932474
AllCCS	[M+H]+	154.2	32859911
AllCCS	[M+H-H2O]+	150.5	32859911
AllCCS	[M+NH4]+	157.7	32859911
AllCCS	[M+Na]+	158.7	32859911
AllCCS	[M-H]-	162.8	32859911
AllCCS	[M+Na-2H]-	162.8	32859911
AllCCS	[M+HCOO]-	163.0	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Curcumenol	CC1CCC2C(C)=CC3(O)OC12CC3=C(C)C	2338.7	Standard polar	33892256
Curcumenol	CC1CCC2C(C)=CC3(O)OC12CC3=C(C)C	1677.0	Standard non polar	33892256
Curcumenol	CC1CCC2C(C)=CC3(O)OC12CC3=C(C)C	1724.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Curcumenol,1TMS,isomer #1	CC1=CC2(O[Si](C)(C)C)OC3(CC2=C(C)C)C(C)CCC13	1852.4	Semi standard non polar	33892256
Curcumenol,1TBDMS,isomer #1	CC1=CC2(O[Si](C)(C)C(C)(C)C)OC3(CC2=C(C)C)C(C)CCC13	2088.1	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Curcumenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0aou-9440000000-e43956bf41f6498b449a	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curcumenol GC-MS (1 TMS) - 70eV, Positive	splash10-0076-9050000000-879a9a23f1d2143b1e1d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curcumenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curcumenol 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 - Curcumenol 10V, Positive-QTOF	splash10-000i-2090000000-8a393c5e1133ac6f20ea	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenol 20V, Positive-QTOF	splash10-052r-9260000000-d82e83fa115ee49ff5ec	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenol 40V, Positive-QTOF	splash10-0q29-9000000000-77b123c5fbb8bfa48e39	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenol 10V, Negative-QTOF	splash10-001i-0090000000-d40a2859b19caf02e499	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenol 20V, Negative-QTOF	splash10-001i-0190000000-904d70234ea8fcec1c80	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenol 40V, Negative-QTOF	splash10-00n3-0900000000-99b7491eebb2a2fa07c5	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenol 10V, Positive-QTOF	splash10-000i-0090000000-2f85d9144addaa938e0f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenol 20V, Positive-QTOF	splash10-000i-0190000000-10595d1d1a9e73b11825	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenol 40V, Positive-QTOF	splash10-00ko-9850000000-1acddc47818c6337a8de	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenol 10V, Negative-QTOF	splash10-001i-0090000000-9087f47ed0ae51229a17	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenol 20V, Negative-QTOF	splash10-001i-0090000000-9087f47ed0ae51229a17	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenol 40V, Negative-QTOF	splash10-014i-0920000000-465d3e6e618121a07869	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

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

Not Available

METLIN ID

Not Available

PubChem Compound

387977

PDB ID

Not Available

ChEBI ID

80811

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 Curcumenol (HMDB0033960)

MOL for HMDB0033960 (Curcumenol)

3D MOL for HMDB0033960 (Curcumenol)

3D SDF for HMDB0033960 (Curcumenol)

3D-SDF for HMDB0033960 (Curcumenol)

PDB for HMDB0033960 (Curcumenol)

3D PDB for HMDB0033960 (Curcumenol)

SMILES for HMDB0033960 (Curcumenol)

INCHI for HMDB0033960 (Curcumenol)

Structure for HMDB0033960 (Curcumenol)

3D Structure for HMDB0033960 (Curcumenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra