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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-08 15:55:36 UTC

Update Date

2022-03-07 03:17:47 UTC

HMDB ID

HMDB0061838

Secondary Accession Numbers

HMDB61838

Metabolite Identification

Common Name

(-)-alpha-Curcumene

Description

(-)-alpha-Curcumene, also known as (R)-curcumene or L-α-curcumene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units (-)-alpha-Curcumene is possibly neutral.

Structure

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

HMDB0061838
     RDKit          3D
(-)-alpha-Curcumene
 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.9113    0.6135    1.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9283    0.1727    0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0957    0.6805   -1.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9276   -0.6545    0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9349   -1.1048   -0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5768   -0.6465    0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5327   -1.0333   -0.8173 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3860   -0.4668   -2.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8021   -0.5152   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    0.8605   -0.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0690    1.3884    0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1059    0.5536    0.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3357    1.1663    1.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9675   -0.8064    0.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8243   -1.3699    0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0699   -0.1746    2.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8568    0.8847    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4763    1.5032    1.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0229    1.2761   -1.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1574   -0.1969   -1.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2629    1.3671   -1.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8641   -0.9868    1.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0000   -2.2139   -0.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2101   -0.6331   -1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3877   -1.1288    1.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6138    0.4341    0.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6036   -2.1390   -0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5842   -1.2664   -2.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.3267   -2.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -0.0550   -2.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1267    1.5500   -0.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1789    2.4708    0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6776    1.9228    0.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0180    1.7056    2.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1149    0.4330    1.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7797   -1.4606    0.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7363   -2.4570   -0.0077 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  6
  8 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
M  END


  Mrv1652301212022263D          

 15 15  0  0  0  0            999 V2000
   -3.9416   -0.5029   -1.4605 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3914    1.3259    0.2690 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7124    1.9657   -0.8218 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7426   -2.0688    2.2282 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2335   -0.6391   -0.6933 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1655    0.2983   -0.0418 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6182   -1.6225    0.2497 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6247    1.8076    0.5660 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3464   -0.1251   -0.5622 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5477    1.1234    1.0853 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2640   -0.8107   -0.0396 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4419    0.3889   -0.3763 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5462    1.2067   -0.2654 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1787   -0.9576    1.3502 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.3430   -0.2104    0.7913 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 12  1  0  0  0  0
  2 12  1  0  0  0  0
  3 13  1  0  0  0  0
  4 14  1  0  0  0  0
  5  6  1  0  0  0  0
  5  7  1  0  0  0  0
  6 12  2  3  0  0  0
  7 14  1  0  0  0  0
  8 10  2  0  0  0  0
  8 13  1  0  0  0  0
  9 11  1  0  0  0  0
  9 13  2  0  0  0  0
 10 15  1  0  0  0  0
 11 15  2  0  0  0  0
 14 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0061838

> <DATABASE_NAME>
hmdb

> <SMILES>
C[C@H](CCC=C(C)C)C1=CC=C(C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-11,14H,5,7H2,1-4H3/t14-/m1/s1

> <INCHI_KEY>
VMYXUZSZMNBRCN-CQSZACIVSA-N

> <FORMULA>
C15H22

> <MOLECULAR_WEIGHT>
202.3352

> <EXACT_MASS>
202.172150704

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
25.81751184034264

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-4-[(2R)-6-methylhept-5-en-2-yl]benzene

> <ALOGPS_LOGP>
6.15

> <JCHEM_LOGP>
5.391390631

> <ALOGPS_LOGS>
-5.31

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
69.0926

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
9.91e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(-)-α-curcumene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0061838
     RDKit          3D
(-)-alpha-Curcumene
 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.9113    0.6135    1.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9283    0.1727    0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0957    0.6805   -1.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9276   -0.6545    0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9349   -1.1048   -0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5768   -0.6465    0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5327   -1.0333   -0.8173 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3860   -0.4668   -2.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8021   -0.5152   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    0.8605   -0.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0690    1.3884    0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1059    0.5536    0.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3357    1.1663    1.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9675   -0.8064    0.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8243   -1.3699    0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0699   -0.1746    2.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8568    0.8847    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4763    1.5032    1.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0229    1.2761   -1.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1574   -0.1969   -1.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2629    1.3671   -1.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8641   -0.9868    1.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0000   -2.2139   -0.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2101   -0.6331   -1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3877   -1.1288    1.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6138    0.4341    0.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6036   -2.1390   -0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5842   -1.2664   -2.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.3267   -2.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -0.0550   -2.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1267    1.5500   -0.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1789    2.4708    0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6776    1.9228    0.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0180    1.7056    2.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1149    0.4330    1.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7797   -1.4606    0.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7363   -2.4570   -0.0077 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  6
  8 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
M  END

HEADER    PROTEIN                                 21-JAN-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JAN-20         0                                  
HETATM    1  C   UNK     0      -3.942  -0.503  -1.460  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.391   1.326   0.269  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.712   1.966  -0.822  0.00  0.00           C+0
HETATM    4  C   UNK     0       0.743  -2.069   2.228  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.234  -0.639  -0.693  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.166   0.298  -0.042  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.618  -1.623   0.250  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.625   1.808   0.566  0.00  0.00           C+0
HETATM    9  C   UNK     0       3.346  -0.125  -0.562  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.548   1.123   1.085  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.264  -0.811  -0.040  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.442   0.389  -0.376  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.546   1.207  -0.265  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.179  -0.958   1.350  0.00  0.00           C+0
HETATM   15  C   UNK     0       1.343  -0.210   0.791  0.00  0.00           C+0
CONECT    1   12                                                            
CONECT    2   12                                                            
CONECT    3   13                                                            
CONECT    4   14                                                            
CONECT    5    6    7                                                       
CONECT    6    5   12                                                       
CONECT    7    5   14                                                       
CONECT    8   10   13                                                       
CONECT    9   11   13                                                       
CONECT   10    8   15                                                       
CONECT   11    9   15                                                       
CONECT   12    1    2    6                                                  
CONECT   13    3    8    9                                                  
CONECT   14    4    7   15                                                  
CONECT   15   10   11   14                                                  
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0061838
HETATM    1  C1  UNL     1      -4.911   0.614   1.356  1.00  0.00           C  
HETATM    2  C2  UNL     1      -3.928   0.173   0.332  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.096   0.680  -1.054  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.928  -0.655   0.654  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.935  -1.105  -0.362  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.577  -0.646   0.115  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.533  -1.033  -0.817  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.386  -0.467  -2.199  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.802  -0.515  -0.245  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.912   0.860  -0.090  1.00  0.00           C  
HETATM   11  C11 UNL     1       3.069   1.388   0.436  1.00  0.00           C  
HETATM   12  C12 UNL     1       4.106   0.554   0.803  1.00  0.00           C  
HETATM   13  C13 UNL     1       5.336   1.166   1.367  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.967  -0.806   0.638  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.824  -1.370   0.115  1.00  0.00           C  
HETATM   16  H1  UNL     1      -5.070  -0.175   2.132  1.00  0.00           H  
HETATM   17  H2  UNL     1      -5.857   0.885   0.869  1.00  0.00           H  
HETATM   18  H3  UNL     1      -4.476   1.503   1.892  1.00  0.00           H  
HETATM   19  H4  UNL     1      -5.023   1.276  -1.122  1.00  0.00           H  
HETATM   20  H5  UNL     1      -4.157  -0.197  -1.730  1.00  0.00           H  
HETATM   21  H6  UNL     1      -3.263   1.367  -1.344  1.00  0.00           H  
HETATM   22  H7  UNL     1      -2.864  -0.987   1.683  1.00  0.00           H  
HETATM   23  H8  UNL     1      -2.000  -2.214  -0.428  1.00  0.00           H  
HETATM   24  H9  UNL     1      -2.210  -0.633  -1.318  1.00  0.00           H  
HETATM   25  H10 UNL     1      -0.388  -1.129   1.085  1.00  0.00           H  
HETATM   26  H11 UNL     1      -0.614   0.434   0.259  1.00  0.00           H  
HETATM   27  H12 UNL     1       0.604  -2.139  -0.875  1.00  0.00           H  
HETATM   28  H13 UNL     1       0.584  -1.266  -2.960  1.00  0.00           H  
HETATM   29  H14 UNL     1       1.139   0.327  -2.400  1.00  0.00           H  
HETATM   30  H15 UNL     1      -0.597  -0.055  -2.425  1.00  0.00           H  
HETATM   31  H16 UNL     1       1.127   1.550  -0.365  1.00  0.00           H  
HETATM   32  H17 UNL     1       3.179   2.471   0.567  1.00  0.00           H  
HETATM   33  H18 UNL     1       5.678   1.923   0.642  1.00  0.00           H  
HETATM   34  H19 UNL     1       5.018   1.706   2.294  1.00  0.00           H  
HETATM   35  H20 UNL     1       6.115   0.433   1.577  1.00  0.00           H  
HETATM   36  H21 UNL     1       4.780  -1.461   0.926  1.00  0.00           H  
HETATM   37  H22 UNL     1       2.736  -2.457  -0.008  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    4    4
CONECT    3   19   20   21
CONECT    4    5   22
CONECT    5    6   23   24
CONECT    6    7   25   26
CONECT    7    8    9   27
CONECT    8   28   29   30
CONECT    9   10   10   15
CONECT   10   11   31
CONECT   11   12   12   32
CONECT   12   13   14
CONECT   13   33   34   35
CONECT   14   15   15   36
CONECT   15   37
END

HMDB0061838
     RDKit          3D
(-)-alpha-Curcumene
 37 37  0  0  0  0  0  0  0  0999 V2000
   -4.9113    0.6135    1.3561 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9283    0.1727    0.3318 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0957    0.6805   -1.0539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9276   -0.6545    0.6538 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9349   -1.1048   -0.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5768   -0.6465    0.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5327   -1.0333   -0.8173 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3860   -0.4668   -2.1986 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8021   -0.5152   -0.2451 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9121    0.8605   -0.0903 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0690    1.3884    0.4355 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1059    0.5536    0.8035 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3357    1.1663    1.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9675   -0.8064    0.6381 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8243   -1.3699    0.1151 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0699   -0.1746    2.1325 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8568    0.8847    0.8689 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4763    1.5032    1.8922 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0229    1.2761   -1.1222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1574   -0.1969   -1.7296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2629    1.3671   -1.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8641   -0.9868    1.6825 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0000   -2.2139   -0.4284 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2101   -0.6331   -1.3179 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3877   -1.1288    1.0849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6138    0.4341    0.2588 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6036   -2.1390   -0.8752 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5842   -1.2664   -2.9601 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1387    0.3267   -2.4001 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5972   -0.0550   -2.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1267    1.5500   -0.3645 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1789    2.4708    0.5671 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6776    1.9228    0.6416 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0180    1.7056    2.2941 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1149    0.4330    1.5774 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7797   -1.4606    0.9262 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7363   -2.4570   -0.0077 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
  7  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  2  0
 12 13  1  0
 12 14  1  0
 14 15  2  0
 15  9  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  6
  8 28  1  0
  8 29  1  0
  8 30  1  0
 10 31  1  0
 11 32  1  0
 13 33  1  0
 13 34  1  0
 13 35  1  0
 14 36  1  0
 15 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(R)-(-)-alpha-Curcumene	ChEBI
(R)-(-)-Curcumene	ChEBI
(R)-Curcumene	ChEBI
4-[(1R)-1,5-Dimethylhex-4-enyl]-1-methylbenzene	ChEBI
L-alpha-Curcumene	ChEBI
(R)-1-(1,5-Dimethyl-4-hexenyl)-4-methylbenzene	Kegg
(R)-(-)-a-Curcumene	Generator
(R)-(-)-Α-curcumene	Generator
L-a-Curcumene	Generator
L-Α-curcumene	Generator
(-)-a-Curcumene	Generator
(-)-Α-curcumene	Generator
(R)-Isomer OF alpha-curcumene	HMDB
1-(1,5-Dimethyl-4-hexenyl)-4-methylbenzene	HMDB
2-Methyl-6-p-tolyl-2-heptene	HMDB
alpha-Curcumene	HMDB
(S)-Isomer OF alpha-curcumene	HMDB
Ar-curcumene	HMDB

Chemical Formula

C₁₅H₂₂

Average Molecular Weight

202.3352

Monoisotopic Molecular Weight

202.172150704

IUPAC Name

1-methyl-4-[(2R)-6-methylhept-5-en-2-yl]benzene

Traditional Name

(-)-α-curcumene

CAS Registry Number

4176-17-4

SMILES

[H][C@@](C)(CCC=C(C)C)C1=CC=C(C)C=C1

InChI Identifier

InChI=1S/C15H22/c1-12(2)6-5-7-14(4)15-10-8-13(3)9-11-15/h6,8-11,14H,5,7H2,1-4H3/t14-/m1/s1

InChI Key

VMYXUZSZMNBRCN-CQSZACIVSA-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

Bisabolane sesquiterpenoid
Sesquiterpenoid
P-cymene
Toluene
Benzenoid
Monocyclic benzene moiety
Aromatic hydrocarbon
Branched unsaturated hydrocarbon
Cyclic olefin
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

alpha-curcumene (CHEBI:10225 )
Bisabolane sesquiterpenoids (C09649 )
Sesquiterpenoids (C15) (C09649 )

Ontology

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.00099 g/L	ALOGPS
logP	6.15	ALOGPS
logP	5.39	ChemAxon
logS	-5.3	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	69.09 m³·mol⁻¹	ChemAxon
Polarizability	25.82 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	150.629	31661259
DarkChem	[M-H]-	149.907	31661259
DeepCCS	[M+H]+	160.331	30932474
DeepCCS	[M-H]-	157.935	30932474
DeepCCS	[M-2H]-	191.16	30932474
DeepCCS	[M+Na]+	166.243	30932474
AllCCS	[M+H]+	146.3	32859911
AllCCS	[M+H-H2O]+	142.2	32859911
AllCCS	[M+NH4]+	150.1	32859911
AllCCS	[M+Na]+	151.2	32859911
AllCCS	[M-H]-	152.2	32859911
AllCCS	[M+Na-2H]-	152.7	32859911
AllCCS	[M+HCOO]-	153.3	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.	9.35 minutes	32390414
Predicted by Siyang on May 30, 2022	20.799 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.59 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2703.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	725.8 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	280.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	456.9 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	391.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	896.0 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	832.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	105.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1841.4 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	748.0 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	1647.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	625.3 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	513.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	474.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	507.1 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	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(-)-alpha-Curcumene	[H][C@@](C)(CCC=C(C)C)C1=CC=C(C)C=C1	1925.6	Standard polar	33892256
(-)-alpha-Curcumene	[H][C@@](C)(CCC=C(C)C)C1=CC=C(C)C=C1	1487.0	Standard non polar	33892256
(-)-alpha-Curcumene	[H][C@@](C)(CCC=C(C)C)C1=CC=C(C)C=C1	1498.9	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 - (-)-alpha-Curcumene GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-4900000000-75e61317c346feecec2e	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (-)-alpha-Curcumene 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 - (-)-alpha-Curcumene 10V, Positive-QTOF	splash10-0udi-0290000000-9e5665300d38ccc6c380	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 20V, Positive-QTOF	splash10-100r-9840000000-d684318a257bbd05693f	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 40V, Positive-QTOF	splash10-066r-9400000000-671ed7e91a8152a3dedd	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 10V, Negative-QTOF	splash10-0udi-0090000000-49907b25f88bc4223ff5	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 20V, Negative-QTOF	splash10-0udi-0090000000-78accdf5fb04e051742c	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 40V, Negative-QTOF	splash10-0ldr-3910000000-0e04f561e347dce60ba2	2017-10-06	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 10V, Positive-QTOF	splash10-014l-7910000000-070594523adb5fcf2590	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 20V, Positive-QTOF	splash10-00kf-9300000000-875e64f2a9577f75db09	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 40V, Positive-QTOF	splash10-0006-9400000000-8fa08e9b4d33a2cfb93e	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 10V, Negative-QTOF	splash10-0udi-0090000000-0b1ac00c3b3c6c0a73b9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 20V, Negative-QTOF	splash10-0udi-0290000000-a1f573a51214364e1f18	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (-)-alpha-Curcumene 40V, Negative-QTOF	splash10-0007-6900000000-b097197b38fa1f21c6f1	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB001674

KNApSAcK ID

C00011617

Chemspider ID

Not Available

KEGG Compound ID

C09649

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

442360

PDB ID

Not Available

ChEBI ID

10225

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

Lenfeld J, Motl O, Trka A: Anti-inflammatory activity of extracts from Conyza canadensis. Pharmazie. 1986 Apr;41(4):268-9. [PubMed:3725873 ]
D'Armas HT, Mootoo BS, Reynolds WF: An unusual sesquiterpene derivative from the Caribbean gorgonian Pseudopterogorgia rigida. J Nat Prod. 2000 Nov;63(11):1593-5. [PubMed:11087620 ]
Schwob I, Bessiere JM, Dherbomez M, Viano J: Composition and antimicrobial activity of the essential oil of Hypericum coris. Fitoterapia. 2002 Oct;73(6):511-3. [PubMed:12385876 ]
Antonious GF, Kochhar TS: Zingiberene and curcumene in wild tomato. J Environ Sci Health B. 2003 Jul;38(4):489-500. [PubMed:12856930 ]
Zhang A, RajanBabu TV: Chiral benzyl centers through asymmetric catalysis. a three-step synthesis of (R)-(-)-alpha-curcumene via asymmetric hydrovinylation. Org Lett. 2004 Sep 2;6(18):3159-61. [PubMed:15330612 ]
Takigawa H, Kubota H, Sonohara H, Okuda M, Tanaka S, Fujikura Y, Ito S: Novel Allylic Oxidation of alpha-Cedrene to sec-Cedrenol by a Rhodococcus Strain. Appl Environ Microbiol. 1993 May;59(5):1336-41. [PubMed:16348930 ]
Mathela CS, Padalia RC, Chanotiya CS: Kanokonyl acetate-rich Indian valerian from northwestern Himalaya. Nat Prod Commun. 2009 Sep;4(9):1253-6. [PubMed:19831039 ]
Takigawa H, Sugiyama M, Shibuya Y: C(35)-terpenes from Bacillus subtilis KSM 6-10. J Nat Prod. 2010 Feb 26;73(2):204-7. doi: 10.1021/np900705q. [PubMed:20085287 ]
Joshi RK: Chemical composition of the essential oil of Lepidagathis fasciculata from Bondla forest of Goa, India. Nat Prod Commun. 2013 Aug;8(8):1163-4. [PubMed:24079194 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for (-)-alpha-Curcumene (HMDB0061838)

MOL for HMDB0061838 ((-)-alpha-Curcumene)

3D MOL for HMDB0061838 ((-)-alpha-Curcumene)

3D SDF for HMDB0061838 ((-)-alpha-Curcumene)

3D-SDF for HMDB0061838 ((-)-alpha-Curcumene)

PDB for HMDB0061838 ((-)-alpha-Curcumene)

3D PDB for HMDB0061838 ((-)-alpha-Curcumene)

SMILES for HMDB0061838 ((-)-alpha-Curcumene)

INCHI for HMDB0061838 ((-)-alpha-Curcumene)

Structure for HMDB0061838 ((-)-alpha-Curcumene)

3D Structure for HMDB0061838 ((-)-alpha-Curcumene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra