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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:57:59 UTC

Update Date

2022-03-07 02:53:38 UTC

HMDB ID

HMDB0033253

Secondary Accession Numbers

HMDB33253

Metabolite Identification

Common Name

Curcumenone

Description

Curcumenone belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on Curcumenone.

Structure

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

HMDB0033253
     RDKit          3D
Curcumenone
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.1643    1.3865    0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9782    1.2164    0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1088    1.2562    2.1986 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6570    1.0001    0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4883   -0.4661   -0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1507   -0.5557   -0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0231   -0.1645    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9257    0.8387   -0.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2752    0.1673   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3175    0.6739    0.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6254   -0.0170    0.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2596    1.9603    1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962   -1.0776   -1.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3997   -1.6275   -1.3470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921   -1.6468   -1.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0738   -1.4767   -0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3087   -2.7606    0.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6740    0.3978    0.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8530    2.1570    0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8453    1.7265   -0.9256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9018    1.2571    1.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4522    1.6635   -0.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5984   -1.1105    0.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3294   -0.7235   -0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1252   -0.0565   -1.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2368   -0.1460    1.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6814    1.1082   -1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9191    1.7327    0.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3968    0.5072    0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4929   -1.0391    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0421   -0.0482   -0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3847    1.9850    1.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2226    2.2014    1.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0319    2.8004    0.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0640   -2.7058   -1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6868   -1.0829   -2.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2529   -3.5931   -0.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5224   -2.9283    1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140   -2.8097    0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  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
  9 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16  6  1  0
 16  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
M  END


  Mrv0541 05061307012D          

 17 18  0  0  0  0            999 V2000
    3.3342    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7132   -0.1914    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0638    2.3645    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4757    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0632    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1908    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3007    0.5230    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2382    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4763    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9053    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4763    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7132    1.2375    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6197    2.0625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  9  1  1  0  0  0  0
  9  2  1  0  0  0  0
 10  3  1  0  0  0  0
 10  5  1  0  0  0  0
 11  7  1  0  0  0  0
 11  9  2  0  0  0  0
 12  6  1  0  0  0  0
 13  7  1  0  0  0  0
 13 12  1  0  0  0  0
 14  8  1  0  0  0  0
 14 11  1  0  0  0  0
 15  4  1  0  0  0  0
 15  8  1  0  0  0  0
 15 12  1  0  0  0  0
 15 13  1  0  0  0  0
 16 10  2  0  0  0  0
 17 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033253

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)CCC1C2CC(=C(C)C)C(=O)CC12C

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-9(2)11-7-13-12(6-5-10(3)16)15(13,4)8-14(11)17/h12-13H,5-8H2,1-4H3

> <INCHI_KEY>
HUZJLWLCLJEXEL-UHFFFAOYSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.334

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.569597538826372

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-7-(3-oxobutyl)-4-(propan-2-ylidene)bicyclo[4.1.0]heptan-3-one

> <ALOGPS_LOGP>
3.04

> <JCHEM_LOGP>
2.7208291093333337

> <ALOGPS_LOGS>
-3.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.639785188411256

> <JCHEM_PKA_STRONGEST_BASIC>
-4.468567003705912

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
68.71699999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.15e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-methyl-7-(3-oxobutyl)-4-(propan-2-ylidene)bicyclo[4.1.0]heptan-3-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0033253
     RDKit          3D
Curcumenone
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.1643    1.3865    0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9782    1.2164    0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1088    1.2562    2.1986 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6570    1.0001    0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4883   -0.4661   -0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1507   -0.5557   -0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0231   -0.1645    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9257    0.8387   -0.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2752    0.1673   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3175    0.6739    0.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6254   -0.0170    0.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2596    1.9603    1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962   -1.0776   -1.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3997   -1.6275   -1.3470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921   -1.6468   -1.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0738   -1.4767   -0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3087   -2.7606    0.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6740    0.3978    0.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8530    2.1570    0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8453    1.7265   -0.9256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9018    1.2571    1.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4522    1.6635   -0.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5984   -1.1105    0.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3294   -0.7235   -0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1252   -0.0565   -1.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2368   -0.1460    1.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6814    1.1082   -1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9191    1.7327    0.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3968    0.5072    0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4929   -1.0391    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0421   -0.0482   -0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3847    1.9850    1.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2226    2.2014    1.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0319    2.8004    0.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0640   -2.7058   -1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6868   -1.0829   -2.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2529   -3.5931   -0.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5224   -2.9283    1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140   -2.8097    0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  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
  9 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16  6  1  0
 16  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  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       6.224   1.540   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.890  -0.770   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -5.065  -0.357   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.119   4.414   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.755   0.976   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.985   2.310   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.223   0.770   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.223   3.850   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.890   0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -4.295   0.976   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       3.557   1.540   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.445   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.889   1.540   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.557   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.889   3.080   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -5.065   2.310   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       4.890   3.850   0.000  0.00  0.00           O+0
CONECT    1    9                                                            
CONECT    2    9                                                            
CONECT    3   10                                                            
CONECT    4   15                                                            
CONECT    5    6   10                                                       
CONECT    6    5   12                                                       
CONECT    7   11   13                                                       
CONECT    8   14   15                                                       
CONECT    9    1    2   11                                                  
CONECT   10    3    5   16                                                  
CONECT   11    7    9   14                                                  
CONECT   12    6   13   15                                                  
CONECT   13    7   12   15                                                  
CONECT   14    8   11   17                                                  
CONECT   15    4    8   12   13                                             
CONECT   16   10                                                            
CONECT   17   14                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0033253
HETATM    1  C1  UNL     1       5.164   1.386   0.101  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.978   1.216   0.979  1.00  0.00           C  
HETATM    3  O1  UNL     1       4.109   1.256   2.199  1.00  0.00           O  
HETATM    4  C3  UNL     1       2.657   1.000   0.332  1.00  0.00           C  
HETATM    5  C4  UNL     1       2.488  -0.466  -0.099  1.00  0.00           C  
HETATM    6  C5  UNL     1       1.151  -0.556  -0.734  1.00  0.00           C  
HETATM    7  C6  UNL     1       0.023  -0.164   0.241  1.00  0.00           C  
HETATM    8  C7  UNL     1      -0.926   0.839  -0.302  1.00  0.00           C  
HETATM    9  C8  UNL     1      -2.275   0.167  -0.340  1.00  0.00           C  
HETATM   10  C9  UNL     1      -3.317   0.674   0.251  1.00  0.00           C  
HETATM   11  C10 UNL     1      -4.625  -0.017   0.185  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.260   1.960   1.019  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.296  -1.078  -1.080  1.00  0.00           C  
HETATM   14  O2  UNL     1      -3.400  -1.627  -1.347  1.00  0.00           O  
HETATM   15  C13 UNL     1      -0.992  -1.647  -1.491  1.00  0.00           C  
HETATM   16  C14 UNL     1       0.074  -1.477  -0.411  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.309  -2.761   0.359  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.674   0.398   0.066  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.853   2.157   0.492  1.00  0.00           H  
HETATM   20  H3  UNL     1       4.845   1.727  -0.926  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.902   1.257   1.109  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.452   1.663  -0.513  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.598  -1.110   0.793  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.329  -0.723  -0.785  1.00  0.00           H  
HETATM   25  H8  UNL     1       1.125  -0.057  -1.747  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.237  -0.146   1.314  1.00  0.00           H  
HETATM   27  H10 UNL     1      -0.681   1.108  -1.367  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.919   1.733   0.331  1.00  0.00           H  
HETATM   29  H12 UNL     1      -5.397   0.507   0.820  1.00  0.00           H  
HETATM   30  H13 UNL     1      -4.493  -1.039   0.594  1.00  0.00           H  
HETATM   31  H14 UNL     1      -5.042  -0.048  -0.859  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.385   1.985   1.721  1.00  0.00           H  
HETATM   33  H16 UNL     1      -4.223   2.201   1.497  1.00  0.00           H  
HETATM   34  H17 UNL     1      -3.032   2.800   0.299  1.00  0.00           H  
HETATM   35  H18 UNL     1      -1.064  -2.706  -1.792  1.00  0.00           H  
HETATM   36  H19 UNL     1      -0.687  -1.083  -2.421  1.00  0.00           H  
HETATM   37  H20 UNL     1       0.253  -3.593  -0.376  1.00  0.00           H  
HETATM   38  H21 UNL     1      -0.522  -2.928   1.085  1.00  0.00           H  
HETATM   39  H22 UNL     1       1.314  -2.810   0.807  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3    4
CONECT    4    5   21   22
CONECT    5    6   23   24
CONECT    6    7   16   25
CONECT    7    8   16   26
CONECT    8    9   27   28
CONECT    9   10   10   13
CONECT   10   11   12
CONECT   11   29   30   31
CONECT   12   32   33   34
CONECT   13   14   14   15
CONECT   15   16   35   36
CONECT   16   17
CONECT   17   37   38   39
END

HMDB0033253
     RDKit          3D
Curcumenone
 39 40  0  0  0  0  0  0  0  0999 V2000
    5.1643    1.3865    0.1006 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9782    1.2164    0.9787 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1088    1.2562    2.1986 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6570    1.0001    0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4883   -0.4661   -0.0990 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1507   -0.5557   -0.7340 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0231   -0.1645    0.2414 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9257    0.8387   -0.3016 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2752    0.1673   -0.3405 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3175    0.6739    0.2506 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6254   -0.0170    0.1846 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2596    1.9603    1.0190 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2962   -1.0776   -1.0804 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3997   -1.6275   -1.3470 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9921   -1.6468   -1.4910 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0738   -1.4767   -0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3087   -2.7606    0.3594 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6740    0.3978    0.0656 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8530    2.1570    0.4915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8453    1.7265   -0.9256 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9018    1.2571    1.1089 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4522    1.6635   -0.5130 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5984   -1.1105    0.7931 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3294   -0.7235   -0.7855 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1252   -0.0565   -1.7475 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2368   -0.1460    1.3142 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6814    1.1082   -1.3669 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9191    1.7327    0.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3968    0.5072    0.8204 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4929   -1.0391    0.5936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0421   -0.0482   -0.8594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3847    1.9850    1.7207 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2226    2.2014    1.4967 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0319    2.8004    0.2994 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0640   -2.7058   -1.7923 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6868   -1.0829   -2.4211 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2529   -3.5931   -0.3758 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5224   -2.9283    1.0845 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3140   -2.8097    0.8070 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  2  4  1  0
  4  5  1  0
  5  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
  9 13  1  0
 13 14  2  0
 13 15  1  0
 15 16  1  0
 16 17  1  0
 16  6  1  0
 16  7  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
 11 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 15 35  1  0
 15 36  1  0
 17 37  1  0
 17 38  1  0
 17 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Curcumenone	MeSH

Chemical Formula

C₁₅H₂₂O₂

Average Molecular Weight

234.334

Monoisotopic Molecular Weight

234.161979948

IUPAC Name

1-methyl-7-(3-oxobutyl)-4-(propan-2-ylidene)bicyclo[4.1.0]heptan-3-one

Traditional Name

1-methyl-7-(3-oxobutyl)-4-(propan-2-ylidene)bicyclo[4.1.0]heptan-3-one

CAS Registry Number

100347-96-4

SMILES

CC(=O)CCC1C2CC(=C(C)C)C(=O)CC12C

InChI Identifier

InChI=1S/C15H22O2/c1-9(2)11-7-13-12(6-5-10(3)16)15(13,4)8-14(11)17/h12-13H,5-8H2,1-4H3

InChI Key

HUZJLWLCLJEXEL-UHFFFAOYSA-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

Carabrane sesquiterpenoid
Sesquiterpenoid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0033253)
Cell membrane (HMDB: HMDB0033253)

Cellular substructure

Extracellular (HMDB: HMDB0033253)
Membrane (HMDB: HMDB0033253)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033253)

Source

Endogenous

Endogenous (HMDB: HMDB0033253)

Plant

Plant (HMDB: HMDB0033253)

Animal

Animal (HMDB: HMDB0033253)

Exogenous

Food

Food (HMDB: HMDB0033253)

Herb and spice

Spice

Turmeric (FooDB: FOOD00068)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0033253)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0033253)

Cellular process

Cell signaling (HMDB: HMDB0033253)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0033253)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0033253)

Nutrient

Nutrient (HMDB: HMDB0033253)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033253)

Emulsifier (HMDB: HMDB0033253)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	343.67 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	42.83 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	1.043 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.12 g/L	ALOGPS
logP	3.04	ALOGPS
logP	2.72	ChemAxon
logS	-3.3	ALOGPS
pKa (Strongest Acidic)	19.64	ChemAxon
pKa (Strongest Basic)	-4.5	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	3	ChemAxon
Refractivity	68.72 m³·mol⁻¹	ChemAxon
Polarizability	27.57 Å³	ChemAxon
Number of Rings	2	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]+	155.442	31661259
DarkChem	[M-H]-	154.378	31661259
DeepCCS	[M-2H]-	189.69	30932474
DeepCCS	[M+Na]+	164.65	30932474
AllCCS	[M+H]+	155.3	32859911
AllCCS	[M+H-H2O]+	151.7	32859911
AllCCS	[M+NH4]+	158.6	32859911
AllCCS	[M+Na]+	159.6	32859911
AllCCS	[M-H]-	164.1	32859911
AllCCS	[M+Na-2H]-	164.5	32859911
AllCCS	[M+HCOO]-	165.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Curcumenone	CC(=O)CCC1C2CC(=C(C)C)C(=O)CC12C	2411.1	Standard polar	33892256
Curcumenone	CC(=O)CCC1C2CC(=C(C)C)C(=O)CC12C	1875.7	Standard non polar	33892256
Curcumenone	CC(=O)CCC1C2CC(=C(C)C)C(=O)CC12C	1830.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Curcumenone,1TMS,isomer #1	CC(=CCC1C2CC(=C(C)C)C(=O)CC12C)O[Si](C)(C)C	2068.2	Semi standard non polar	33892256
Curcumenone,1TMS,isomer #1	CC(=CCC1C2CC(=C(C)C)C(=O)CC12C)O[Si](C)(C)C	1972.9	Standard non polar	33892256
Curcumenone,1TMS,isomer #2	CC(=O)CCC1C2CC(=C(C)C)C(O[Si](C)(C)C)=CC12C	1917.4	Semi standard non polar	33892256
Curcumenone,1TMS,isomer #2	CC(=O)CCC1C2CC(=C(C)C)C(O[Si](C)(C)C)=CC12C	1885.5	Standard non polar	33892256
Curcumenone,1TMS,isomer #3	C=C(CCC1C2CC(=C(C)C)C(=O)CC12C)O[Si](C)(C)C	2007.8	Semi standard non polar	33892256
Curcumenone,1TMS,isomer #3	C=C(CCC1C2CC(=C(C)C)C(=O)CC12C)O[Si](C)(C)C	1970.9	Standard non polar	33892256
Curcumenone,2TMS,isomer #1	CC(=CCC1C2CC(=C(C)C)C(O[Si](C)(C)C)=CC12C)O[Si](C)(C)C	2016.4	Semi standard non polar	33892256
Curcumenone,2TMS,isomer #1	CC(=CCC1C2CC(=C(C)C)C(O[Si](C)(C)C)=CC12C)O[Si](C)(C)C	2030.2	Standard non polar	33892256
Curcumenone,2TMS,isomer #2	C=C(CCC1C2CC(=C(C)C)C(O[Si](C)(C)C)=CC12C)O[Si](C)(C)C	1920.5	Semi standard non polar	33892256
Curcumenone,2TMS,isomer #2	C=C(CCC1C2CC(=C(C)C)C(O[Si](C)(C)C)=CC12C)O[Si](C)(C)C	2038.1	Standard non polar	33892256
Curcumenone,1TBDMS,isomer #1	CC(=CCC1C2CC(=C(C)C)C(=O)CC12C)O[Si](C)(C)C(C)(C)C	2308.8	Semi standard non polar	33892256
Curcumenone,1TBDMS,isomer #1	CC(=CCC1C2CC(=C(C)C)C(=O)CC12C)O[Si](C)(C)C(C)(C)C	2219.7	Standard non polar	33892256
Curcumenone,1TBDMS,isomer #2	CC(=O)CCC1C2CC(=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC12C	2151.7	Semi standard non polar	33892256
Curcumenone,1TBDMS,isomer #2	CC(=O)CCC1C2CC(=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC12C	2081.1	Standard non polar	33892256
Curcumenone,1TBDMS,isomer #3	C=C(CCC1C2CC(=C(C)C)C(=O)CC12C)O[Si](C)(C)C(C)(C)C	2256.9	Semi standard non polar	33892256
Curcumenone,1TBDMS,isomer #3	C=C(CCC1C2CC(=C(C)C)C(=O)CC12C)O[Si](C)(C)C(C)(C)C	2206.8	Standard non polar	33892256
Curcumenone,2TBDMS,isomer #1	CC(=CCC1C2CC(=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC12C)O[Si](C)(C)C(C)(C)C	2466.4	Semi standard non polar	33892256
Curcumenone,2TBDMS,isomer #1	CC(=CCC1C2CC(=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC12C)O[Si](C)(C)C(C)(C)C	2442.4	Standard non polar	33892256
Curcumenone,2TBDMS,isomer #2	C=C(CCC1C2CC(=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC12C)O[Si](C)(C)C(C)(C)C	2358.6	Semi standard non polar	33892256
Curcumenone,2TBDMS,isomer #2	C=C(CCC1C2CC(=C(C)C)C(O[Si](C)(C)C(C)(C)C)=CC12C)O[Si](C)(C)C(C)(C)C	2413.8	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Curcumenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-7920000000-7521392b1f7bd3d3a13b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curcumenone 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 - Curcumenone 10V, Positive-QTOF	splash10-00kr-0290000000-44231713c7604901ad6e	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenone 20V, Positive-QTOF	splash10-0170-3930000000-21621f417134ecc8a075	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenone 40V, Positive-QTOF	splash10-0159-7900000000-ebb5437275fc9ee202a5	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenone 10V, Negative-QTOF	splash10-001i-0090000000-cc1c2bfa5613282075f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenone 20V, Negative-QTOF	splash10-001i-4390000000-2c1883d4f4dc1f59ae00	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenone 40V, Negative-QTOF	splash10-0a4i-9320000000-2a8c666d152a109c0284	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenone 10V, Positive-QTOF	splash10-02ti-0950000000-2b38c731d12eef403947	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenone 20V, Positive-QTOF	splash10-0296-7900000000-9b02057600bf2fb4b97b	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenone 40V, Positive-QTOF	splash10-0006-9200000000-9e6d00d0883ea72de036	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenone 10V, Negative-QTOF	splash10-001i-0090000000-9087f47ed0ae51229a17	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenone 20V, Negative-QTOF	splash10-001i-1490000000-66cee83414f465b42ca5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curcumenone 40V, Negative-QTOF	splash10-0ab9-1910000000-7cbd10787baf61ef72ea	2021-09-25	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

Not Available

METLIN ID

Not Available

PubChem Compound

14632994

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1620311

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 Curcumenone (HMDB0033253)

MOL for HMDB0033253 (Curcumenone)

3D MOL for HMDB0033253 (Curcumenone)

3D SDF for HMDB0033253 (Curcumenone)

3D-SDF for HMDB0033253 (Curcumenone)

PDB for HMDB0033253 (Curcumenone)

3D PDB for HMDB0033253 (Curcumenone)

SMILES for HMDB0033253 (Curcumenone)

INCHI for HMDB0033253 (Curcumenone)

Structure for HMDB0033253 (Curcumenone)

3D Structure for HMDB0033253 (Curcumenone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra