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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:53:38 UTC

Update Date

2022-03-07 02:53:35 UTC

HMDB ID

HMDB0033083

Secondary Accession Numbers

HMDB33083

Metabolite Identification

Common Name

(4S)-Dihydrocurcumenone

Description

(4S)-Dihydrocurcumenone 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 (4S)-Dihydrocurcumenone.

Structure

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

HMDB0033083
     RDKit          3D
(4S)-Dihydrocurcumenone
 41 42  0  0  0  0  0  0  0  0999 V2000
   -4.0213    1.4165   -1.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7571    0.4853    0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7526    0.4263    1.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885   -0.2737    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433   -0.2536   -0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3326    0.0403   -0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929   -0.9092   -0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2134   -0.4445   -0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5782    0.5442   -1.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0176    0.9684   -1.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9743   -0.1738   -1.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1438    1.5918    0.0958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0454   -0.8460    0.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6427   -0.3049    2.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0856   -1.8812    1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4066   -1.1935    1.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2481   -1.3759    2.1475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0847    1.7027   -1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7822    0.9504   -2.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4177    2.3473   -0.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2274   -0.5590    1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444    0.7243    2.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5968    1.1460    1.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6157   -1.2786   -1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8184    0.5301   -1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1386    1.1259   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6245   -1.8419   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867   -1.3207   -0.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4094    0.0307    0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4777    0.0757   -2.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9302    1.4359   -1.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2378    1.7456   -1.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6334   -1.0160   -1.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9566    0.1826   -1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2119   -0.5876   -0.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8680    2.2681   -0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8470    0.7788    2.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513   -0.3920    3.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5712   -0.8506    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -2.3518    2.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1256   -2.6625    0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 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  2  0
 16  4  1  0
 13  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
M  END


  Mrv0541 05061306542D          

 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  1  0  0  0  0
 17 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0033083

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-9(2)11-7-13-12(6-5-10(3)16)15(13,4)8-14(11)17/h10,12-13,16H,5-8H2,1-4H3

> <INCHI_KEY>
OQZCUYXRSFWCJU-UHFFFAOYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.3499

> <EXACT_MASS>
236.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.32276687704385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
2.24

> <JCHEM_LOGP>
2.691341759666667

> <ALOGPS_LOGS>
-3.16

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
17.60900782917093

> <JCHEM_PKA_STRONGEST_BASIC>
-1.6569503700662418

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
69.848

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.64e-01 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0033083
     RDKit          3D
(4S)-Dihydrocurcumenone
 41 42  0  0  0  0  0  0  0  0999 V2000
   -4.0213    1.4165   -1.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7571    0.4853    0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7526    0.4263    1.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885   -0.2737    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433   -0.2536   -0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3326    0.0403   -0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929   -0.9092   -0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2134   -0.4445   -0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5782    0.5442   -1.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0176    0.9684   -1.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9743   -0.1738   -1.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1438    1.5918    0.0958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0454   -0.8460    0.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6427   -0.3049    2.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0856   -1.8812    1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4066   -1.1935    1.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2481   -1.3759    2.1475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0847    1.7027   -1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7822    0.9504   -2.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4177    2.3473   -0.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2274   -0.5590    1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444    0.7243    2.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5968    1.1460    1.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6157   -1.2786   -1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8184    0.5301   -1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1386    1.1259   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6245   -1.8419   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867   -1.3207   -0.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4094    0.0307    0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4777    0.0757   -2.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9302    1.4359   -1.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2378    1.7456   -1.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6334   -1.0160   -1.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9566    0.1826   -1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2119   -0.5876   -0.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8680    2.2681   -0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8470    0.7788    2.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513   -0.3920    3.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5712   -0.8506    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -2.3518    2.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1256   -2.6625    0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 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  2  0
 16  4  1  0
 13  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  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    HMDB0033083
HETATM    1  C1  UNL     1      -4.021   1.417  -1.049  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.757   0.485   0.081  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.753   0.426   1.179  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.688  -0.274   0.138  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.643  -0.254  -0.949  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.333   0.040  -0.241  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.793  -0.909  -0.324  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.213  -0.444  -0.221  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.578   0.544  -1.309  1.00  0.00           C  
HETATM   10  C10 UNL     1       4.018   0.968  -1.145  1.00  0.00           C  
HETATM   11  C11 UNL     1       4.974  -0.174  -1.233  1.00  0.00           C  
HETATM   12  O1  UNL     1       4.144   1.592   0.096  1.00  0.00           O  
HETATM   13  C12 UNL     1      -0.045  -0.846   0.903  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.643  -0.305   2.145  1.00  0.00           C  
HETATM   15  C14 UNL     1      -1.086  -1.881   1.187  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.407  -1.193   1.233  1.00  0.00           C  
HETATM   17  O2  UNL     1      -3.248  -1.376   2.148  1.00  0.00           O  
HETATM   18  H1  UNL     1      -5.085   1.703  -1.063  1.00  0.00           H  
HETATM   19  H2  UNL     1      -3.782   0.950  -2.031  1.00  0.00           H  
HETATM   20  H3  UNL     1      -3.418   2.347  -0.967  1.00  0.00           H  
HETATM   21  H4  UNL     1      -5.227  -0.559   1.244  1.00  0.00           H  
HETATM   22  H5  UNL     1      -4.244   0.724   2.131  1.00  0.00           H  
HETATM   23  H6  UNL     1      -5.597   1.146   1.000  1.00  0.00           H  
HETATM   24  H7  UNL     1      -1.616  -1.279  -1.378  1.00  0.00           H  
HETATM   25  H8  UNL     1      -1.818   0.530  -1.682  1.00  0.00           H  
HETATM   26  H9  UNL     1      -0.139   1.126  -0.066  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.625  -1.842  -0.937  1.00  0.00           H  
HETATM   28  H11 UNL     1       2.887  -1.321  -0.324  1.00  0.00           H  
HETATM   29  H12 UNL     1       2.409   0.031   0.747  1.00  0.00           H  
HETATM   30  H13 UNL     1       2.478   0.076  -2.320  1.00  0.00           H  
HETATM   31  H14 UNL     1       1.930   1.436  -1.285  1.00  0.00           H  
HETATM   32  H15 UNL     1       4.238   1.746  -1.933  1.00  0.00           H  
HETATM   33  H16 UNL     1       4.633  -1.016  -1.854  1.00  0.00           H  
HETATM   34  H17 UNL     1       5.957   0.183  -1.643  1.00  0.00           H  
HETATM   35  H18 UNL     1       5.212  -0.588  -0.218  1.00  0.00           H  
HETATM   36  H19 UNL     1       4.868   2.268  -0.000  1.00  0.00           H  
HETATM   37  H20 UNL     1       0.847   0.779   2.022  1.00  0.00           H  
HETATM   38  H21 UNL     1      -0.051  -0.392   3.005  1.00  0.00           H  
HETATM   39  H22 UNL     1       1.571  -0.851   2.386  1.00  0.00           H  
HETATM   40  H23 UNL     1      -0.934  -2.352   2.158  1.00  0.00           H  
HETATM   41  H24 UNL     1      -1.126  -2.663   0.371  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    4    4
CONECT    3   21   22   23
CONECT    4    5   16
CONECT    5    6   24   25
CONECT    6    7   13   26
CONECT    7    8   13   27
CONECT    8    9   28   29
CONECT    9   10   30   31
CONECT   10   11   12   32
CONECT   11   33   34   35
CONECT   12   36
CONECT   13   14   15
CONECT   14   37   38   39
CONECT   15   16   40   41
CONECT   16   17   17
END

HMDB0033083
     RDKit          3D
(4S)-Dihydrocurcumenone
 41 42  0  0  0  0  0  0  0  0999 V2000
   -4.0213    1.4165   -1.0495 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7571    0.4853    0.0808 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7526    0.4263    1.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6885   -0.2737    0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6433   -0.2536   -0.9494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3326    0.0403   -0.2412 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7929   -0.9092   -0.3237 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2134   -0.4445   -0.2211 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5782    0.5442   -1.3092 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0176    0.9684   -1.1453 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9743   -0.1738   -1.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1438    1.5918    0.0958 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0454   -0.8460    0.9026 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6427   -0.3049    2.1452 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0856   -1.8812    1.1871 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4066   -1.1935    1.2326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2481   -1.3759    2.1475 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0847    1.7027   -1.0633 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7822    0.9504   -2.0306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4177    2.3473   -0.9673 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2274   -0.5590    1.2439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2444    0.7243    2.1314 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5968    1.1460    1.0004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6157   -1.2786   -1.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8184    0.5301   -1.6823 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1386    1.1259   -0.0660 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6245   -1.8419   -0.9374 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8867   -1.3207   -0.3235 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4094    0.0307    0.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4777    0.0757   -2.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9302    1.4359   -1.2847 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2378    1.7456   -1.9330 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6334   -1.0160   -1.8535 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9566    0.1826   -1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2119   -0.5876   -0.2180 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8680    2.2681   -0.0001 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8470    0.7788    2.0216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0513   -0.3920    3.0047 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5712   -0.8506    2.3864 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9336   -2.3518    2.1583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1256   -2.6625    0.3712 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 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  2  0
 16  4  1  0
 13  6  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  3 21  1  0
  3 22  1  0
  3 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  7 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 11 33  1  0
 11 34  1  0
 11 35  1  0
 12 36  1  0
 14 37  1  0
 14 38  1  0
 14 39  1  0
 15 40  1  0
 15 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
4S-Dihydrocurcumenone	HMDB

Chemical Formula

C₁₅H₂₄O₂

Average Molecular Weight

236.3499

Monoisotopic Molecular Weight

236.177630012

IUPAC Name

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

Traditional Name

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

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C15H24O2/c1-9(2)11-7-13-12(6-5-10(3)16)15(13,4)8-14(11)17/h10,12-13,16H,5-8H2,1-4H3

InChI Key

OQZCUYXRSFWCJU-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
Secondary alcohol
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033083)

Source

Endogenous

Endogenous (HMDB: HMDB0033083)

Animal

Animal (HMDB: HMDB0033083)

Exogenous

Food

Food (HMDB: HMDB0033083)

Exogenous (HMDB: HMDB0033083)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0033083)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0033083)

Lipid metabolism pathway (HMDB: HMDB0033083)

Cellular process

Cell signaling (HMDB: HMDB0033083)

Biochemical process

Lipid transport (HMDB: HMDB0033083)

Role

Biological role

Energy source (HMDB: HMDB0033083)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033083)

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	0.16 g/L	ALOGPS
logP	2.24	ALOGPS
logP	2.69	ChemAxon
logS	-3.2	ALOGPS
pKa (Strongest Acidic)	17.61	ChemAxon
pKa (Strongest Basic)	-1.7	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	3	ChemAxon
Refractivity	69.85 m³·mol⁻¹	ChemAxon
Polarizability	28.32 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]+	157.129	31661259
DarkChem	[M-H]-	154.555	31661259
DeepCCS	[M-2H]-	191.153	30932474
DeepCCS	[M+Na]+	166.777	30932474
AllCCS	[M+H]+	157.4	32859911
AllCCS	[M+H-H2O]+	153.8	32859911
AllCCS	[M+NH4]+	160.7	32859911
AllCCS	[M+Na]+	161.6	32859911
AllCCS	[M-H]-	165.1	32859911
AllCCS	[M+Na-2H]-	165.7	32859911
AllCCS	[M+HCOO]-	166.4	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.2 minutes	32390414
Predicted by Siyang on May 30, 2022	13.6339 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.19 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	25.8 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2301.8 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	358.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	174.1 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	168.2 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	163.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	524.9 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	653.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	66.4 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1016.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	422.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1284.0 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	317.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	377.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	245.8 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	386.2 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	11.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(4S)-Dihydrocurcumenone	CC(O)CCC1C2CC(=C(C)C)C(=O)CC12C	2670.7	Standard polar	33892256
(4S)-Dihydrocurcumenone	CC(O)CCC1C2CC(=C(C)C)C(=O)CC12C	1866.8	Standard non polar	33892256
(4S)-Dihydrocurcumenone	CC(O)CCC1C2CC(=C(C)C)C(=O)CC12C	1887.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(4S)-Dihydrocurcumenone,1TMS,isomer #1	CC(C)=C1CC2C(CCC(C)O[Si](C)(C)C)C2(C)CC1=O	2021.5	Semi standard non polar	33892256
(4S)-Dihydrocurcumenone,1TMS,isomer #2	CC(C)=C1CC2C(CCC(C)O)C2(C)C=C1O[Si](C)(C)C	1925.0	Semi standard non polar	33892256
(4S)-Dihydrocurcumenone,2TMS,isomer #1	CC(C)=C1CC2C(CCC(C)O[Si](C)(C)C)C2(C)C=C1O[Si](C)(C)C	1956.5	Semi standard non polar	33892256
(4S)-Dihydrocurcumenone,2TMS,isomer #1	CC(C)=C1CC2C(CCC(C)O[Si](C)(C)C)C2(C)C=C1O[Si](C)(C)C	2064.4	Standard non polar	33892256
(4S)-Dihydrocurcumenone,1TBDMS,isomer #1	CC(C)=C1CC2C(CCC(C)O[Si](C)(C)C(C)(C)C)C2(C)CC1=O	2273.7	Semi standard non polar	33892256
(4S)-Dihydrocurcumenone,1TBDMS,isomer #2	CC(C)=C1CC2C(CCC(C)O)C2(C)C=C1O[Si](C)(C)C(C)(C)C	2155.5	Semi standard non polar	33892256
(4S)-Dihydrocurcumenone,2TBDMS,isomer #1	CC(C)=C1CC2C(CCC(C)O[Si](C)(C)C(C)(C)C)C2(C)C=C1O[Si](C)(C)C(C)(C)C	2403.1	Semi standard non polar	33892256
(4S)-Dihydrocurcumenone,2TBDMS,isomer #1	CC(C)=C1CC2C(CCC(C)O[Si](C)(C)C(C)(C)C)C2(C)C=C1O[Si](C)(C)C(C)(C)C	2447.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - (4S)-Dihydrocurcumenone GC-MS (Non-derivatized) - 70eV, Positive	splash10-00r2-6940000000-96f823f6966fb71168f9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4S)-Dihydrocurcumenone GC-MS (1 TMS) - 70eV, Positive	splash10-00kp-8970000000-8fa7792d436d8f6a2892	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (4S)-Dihydrocurcumenone 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 - (4S)-Dihydrocurcumenone 10V, Positive-QTOF	splash10-014i-0190000000-0ace64eaaed598ea9b68	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S)-Dihydrocurcumenone 20V, Positive-QTOF	splash10-016r-4960000000-1ad669587b5d57450d28	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S)-Dihydrocurcumenone 40V, Positive-QTOF	splash10-0gbi-6910000000-f9d7aa91ce48d90e4658	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S)-Dihydrocurcumenone 10V, Negative-QTOF	splash10-000i-0190000000-525a62becfe5397bef3a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S)-Dihydrocurcumenone 20V, Negative-QTOF	splash10-00kr-1390000000-7253087b55179217fa43	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S)-Dihydrocurcumenone 40V, Negative-QTOF	splash10-0ar3-7960000000-539a0d467d15cc3013b1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S)-Dihydrocurcumenone 10V, Negative-QTOF	splash10-000i-0090000000-c0031dc201eac6b6350a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S)-Dihydrocurcumenone 20V, Negative-QTOF	splash10-000i-0090000000-6249a7cf55e6136bb53e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S)-Dihydrocurcumenone 40V, Negative-QTOF	splash10-00b9-0920000000-0c0393d2d780a2de5c56	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S)-Dihydrocurcumenone 10V, Positive-QTOF	splash10-014r-1590000000-1d1c72c8b4dd8deed7b2	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S)-Dihydrocurcumenone 20V, Positive-QTOF	splash10-0cdu-4910000000-83b7567a6cdea4ce9fc9	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (4S)-Dihydrocurcumenone 40V, Positive-QTOF	splash10-05mo-9300000000-cb62af6225d6acbe62b0	2021-09-25	Wishart 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

FDB011078

KNApSAcK ID

C00029543

Chemspider ID

35013544

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

78178011

PDB ID

Not Available

ChEBI ID

173705

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 (4S)-Dihydrocurcumenone (HMDB0033083)

MOL for HMDB0033083 ((4S)-Dihydrocurcumenone)

3D MOL for HMDB0033083 ((4S)-Dihydrocurcumenone)

3D SDF for HMDB0033083 ((4S)-Dihydrocurcumenone)

3D-SDF for HMDB0033083 ((4S)-Dihydrocurcumenone)

PDB for HMDB0033083 ((4S)-Dihydrocurcumenone)

3D PDB for HMDB0033083 ((4S)-Dihydrocurcumenone)

SMILES for HMDB0033083 ((4S)-Dihydrocurcumenone)

INCHI for HMDB0033083 ((4S)-Dihydrocurcumenone)

Structure for HMDB0033083 ((4S)-Dihydrocurcumenone)

3D Structure for HMDB0033083 ((4S)-Dihydrocurcumenone)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra