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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-03-07 21:34:33 UTC

Update Date

2022-03-07 03:17:37 UTC

HMDB ID

HMDB0059878

Secondary Accession Numbers

HMDB59878

Metabolite Identification

Common Name

alpha-Curcumene

Description

alpha-Curcumene, also known as ar-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

HMDB0059878
     RDKit          3D
alpha-Curcumene
 37 37  0  0  0  0  0  0  0  0999 V2000
    3.9362    0.8879   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6002   -0.0178    0.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3141    0.2198    1.7578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7209   -0.9775    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0425   -1.1682   -0.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5382   -1.1924   -0.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0281    0.0545   -0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2937    1.2304   -1.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4702    0.0284   -0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4090   -0.1668   -1.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7523   -0.1850   -0.7915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2283   -0.0031    0.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6604   -0.0170    0.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3016    0.1932    1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9560    0.2058    1.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2377    0.2467   -1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0890    1.5484   -0.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8547    1.5053   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9266   -0.4993    2.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4063    0.0031    1.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960    1.2764    2.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4869   -1.6410    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3901   -0.4818   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3636   -2.2023   -1.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2982   -2.0745   -0.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1446   -1.4715   -1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4859    0.2323    0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6633    1.6002   -1.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7338    2.0771   -0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9291    0.8958   -2.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0366   -0.3069   -2.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4792   -0.3391   -1.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1554    0.9564    0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7700   -0.3352    1.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1520   -0.7795    0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6724    0.3328    2.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2535    0.3643    2.0275 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  0
  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

Curcumene-alpha
  Mrv1652304022019372D          

 15 15  0  0  0  0            999 V2000
   15.0079   -6.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0079   -7.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2934   -6.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2934   -8.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5789   -6.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5789   -7.5890    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8644   -8.0015    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7224   -6.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4368   -6.7640    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7224   -5.5265    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1561   -6.3515    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8693   -6.7661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5850   -6.3557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.2983   -6.7702    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.5874   -5.5307    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  1  2  0  0  0  0
  4  2  2  0  0  0  0
  5  3  1  0  0  0  0
  6  4  1  0  0  0  0
  6  5  2  0  0  0  0
  6  7  1  0  0  0  0
  1  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059878

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(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

> <INCHI_KEY>
VMYXUZSZMNBRCN-UHFFFAOYSA-N

> <FORMULA>
C15H22

> <MOLECULAR_WEIGHT>
202.341

> <EXACT_MASS>
202.172150708

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
37

> <JCHEM_AVERAGE_POLARIZABILITY>
26.167009029782385

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-methyl-4-(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>
curcumene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0059878
     RDKit          3D
alpha-Curcumene
 37 37  0  0  0  0  0  0  0  0999 V2000
    3.9362    0.8879   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6002   -0.0178    0.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3141    0.2198    1.7578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7209   -0.9775    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0425   -1.1682   -0.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5382   -1.1924   -0.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0281    0.0545   -0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2937    1.2304   -1.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4702    0.0284   -0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4090   -0.1668   -1.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7523   -0.1850   -0.7915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2283   -0.0031    0.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6604   -0.0170    0.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3016    0.1932    1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9560    0.2058    1.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2377    0.2467   -1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0890    1.5484   -0.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8547    1.5053   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9266   -0.4993    2.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4063    0.0031    1.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960    1.2764    2.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4869   -1.6410    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3901   -0.4818   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3636   -2.2023   -1.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2982   -2.0745   -0.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1446   -1.4715   -1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4859    0.2323    0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6633    1.6002   -1.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7338    2.0771   -0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9291    0.8958   -2.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0366   -0.3069   -2.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4792   -0.3391   -1.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1554    0.9564    0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7700   -0.3352    1.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1520   -0.7795    0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6724    0.3328    2.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2535    0.3643    2.0275 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  0
  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                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: Curcumene-alpha                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  C   UNK     0      28.015 -12.626   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.015 -14.166   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      26.681 -11.856   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      26.681 -14.936   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      25.347 -12.626   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      25.347 -14.166   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      24.014 -14.936   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      29.348 -11.856   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      30.682 -12.626   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      29.348 -10.316   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      32.025 -11.856   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      33.356 -12.630   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      34.692 -11.864   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      36.023 -12.638   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      34.696 -10.324   0.000  0.00  0.00           C+0
CONECT    1    2    3    8                                                  
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    6                                                       
CONECT    6    4    5    7                                                  
CONECT    7    6                                                            
CONECT    8    1    9   10                                                  
CONECT    9    8   11                                                       
CONECT   10    8                                                            
CONECT   11    9   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0059878
HETATM    1  C1  UNL     1       3.936   0.888  -0.661  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.600  -0.018   0.453  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.314   0.220   1.758  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.721  -0.977   0.303  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.042  -1.168  -0.998  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.538  -1.192  -0.865  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.028   0.055  -0.308  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.294   1.230  -1.208  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.470   0.028  -0.068  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.409  -0.167  -1.055  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.752  -0.185  -0.792  1.00  0.00           C  
HETATM   12  C12 UNL     1      -4.228  -0.003   0.510  1.00  0.00           C  
HETATM   13  C13 UNL     1      -5.660  -0.017   0.826  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.302   0.193   1.509  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.956   0.206   1.209  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.238   0.247  -1.535  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.089   1.548  -0.873  1.00  0.00           H  
HETATM   18  H3  UNL     1       4.855   1.505  -0.411  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.927  -0.499   2.479  1.00  0.00           H  
HETATM   20  H5  UNL     1       5.406   0.003   1.620  1.00  0.00           H  
HETATM   21  H6  UNL     1       4.196   1.276   2.073  1.00  0.00           H  
HETATM   22  H7  UNL     1       2.487  -1.641   1.142  1.00  0.00           H  
HETATM   23  H8  UNL     1       2.390  -0.482  -1.773  1.00  0.00           H  
HETATM   24  H9  UNL     1       2.364  -2.202  -1.335  1.00  0.00           H  
HETATM   25  H10 UNL     1       0.298  -2.074  -0.207  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.145  -1.471  -1.862  1.00  0.00           H  
HETATM   27  H12 UNL     1       0.486   0.232   0.690  1.00  0.00           H  
HETATM   28  H13 UNL     1      -0.663   1.600  -1.624  1.00  0.00           H  
HETATM   29  H14 UNL     1       0.734   2.077  -0.646  1.00  0.00           H  
HETATM   30  H15 UNL     1       0.929   0.896  -2.049  1.00  0.00           H  
HETATM   31  H16 UNL     1      -2.037  -0.307  -2.059  1.00  0.00           H  
HETATM   32  H17 UNL     1      -4.479  -0.339  -1.575  1.00  0.00           H  
HETATM   33  H18 UNL     1      -6.155   0.956   0.722  1.00  0.00           H  
HETATM   34  H19 UNL     1      -5.770  -0.335   1.884  1.00  0.00           H  
HETATM   35  H20 UNL     1      -6.152  -0.780   0.185  1.00  0.00           H  
HETATM   36  H21 UNL     1      -3.672   0.333   2.509  1.00  0.00           H  
HETATM   37  H22 UNL     1      -1.253   0.364   2.028  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

HMDB0059878
     RDKit          3D
alpha-Curcumene
 37 37  0  0  0  0  0  0  0  0999 V2000
    3.9362    0.8879   -0.6614 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6002   -0.0178    0.4534 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3141    0.2198    1.7578 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7209   -0.9775    0.3028 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0425   -1.1682   -0.9983 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5382   -1.1924   -0.8647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0281    0.0545   -0.3078 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2937    1.2304   -1.2078 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4702    0.0284   -0.0676 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4090   -0.1668   -1.0549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7523   -0.1850   -0.7915 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2283   -0.0031    0.5103 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6604   -0.0170    0.8264 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3016    0.1932    1.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9560    0.2058    1.2089 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2377    0.2467   -1.5351 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0890    1.5484   -0.8735 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8547    1.5053   -0.4106 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9266   -0.4993    2.4794 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4063    0.0031    1.6197 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1960    1.2764    2.0734 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4869   -1.6410    1.1424 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3901   -0.4818   -1.7727 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3636   -2.2023   -1.3347 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2982   -2.0745   -0.2067 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1446   -1.4715   -1.8620 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4859    0.2323    0.6905 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6633    1.6002   -1.6242 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7338    2.0771   -0.6456 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9291    0.8958   -2.0486 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0366   -0.3069   -2.0592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4792   -0.3391   -1.5751 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1554    0.9564    0.7224 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7700   -0.3352    1.8836 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1520   -0.7795    0.1854 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6724    0.3328    2.5094 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2535    0.3643    2.0275 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  0
  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
1-(1,5-Dimethyl-4-hexenyl)-4-methylbenzene	ChEBI
2-Methyl-6-p-tolyl-2-heptene	ChEBI
Ar-curcumene	ChEBI
Aromatic curcumene	ChEBI
Aryl-curcumene	ChEBI
Curcumene	ChEBI
a-Curcumene	Generator
Α-curcumene	Generator
(S)-Isomer OF alpha-curcumene	HMDB
(R)-Isomer OF alpha-curcumene	HMDB

Chemical Formula

C₁₅H₂₂

Average Molecular Weight

202.341

Monoisotopic Molecular Weight

202.172150708

IUPAC Name

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

Traditional Name

curcumene

CAS Registry Number

Not Available

SMILES

CC(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

InChI Key

VMYXUZSZMNBRCN-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

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

sesquiterpene (CHEBI:62757 )
a sesquiterpenoid (CPD-11391 )

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	26.17 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]+	151.021	31661259
DarkChem	[M-H]-	147.648	31661259
DeepCCS	[M+H]+	153.33	30932474
DeepCCS	[M-H]-	150.972	30932474
DeepCCS	[M-2H]-	185.816	30932474
DeepCCS	[M+Na]+	160.8	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 Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Curcumene	CC(CCC=C(C)C)C1=CC=C(C)C=C1	1889.7	Standard polar	33892256
alpha-Curcumene	CC(CCC=C(C)C)C1=CC=C(C)C=C1	1471.5	Standard non polar	33892256
alpha-Curcumene	CC(CCC=C(C)C)C1=CC=C(C)C=C1	1466.5	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-4900000000-02de9aa588ac8b953932	2016-09-22	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
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	Mass Spectrum (Electron Ionization)	splash10-067l-6900000000-5adc5ed56d3450aebc61	2015-03-01	Not Available	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-1390000000-266c956bab292ff3d48f	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Curcumene 20V, Positive-QTOF	splash10-0uyi-5940000000-13708122d7e2946ab589	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Curcumene 40V, Positive-QTOF	splash10-014i-9600000000-8069c29cdaa20b53c057	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Curcumene 10V, Negative-QTOF	splash10-0udi-0090000000-705074079b3b227e8179	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Curcumene 20V, Negative-QTOF	splash10-0udi-0190000000-189af3990d1c9d3163cc	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Curcumene 40V, Negative-QTOF	splash10-0ldr-4910000000-7bf2915fe0383c8edf0d	2016-09-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Curcumene 10V, Positive-QTOF	splash10-014l-8910000000-59d05b6be264b168f53f	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Curcumene 20V, Positive-QTOF	splash10-00kf-9300000000-d00dad7d95d26e8476aa	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Curcumene 40V, Positive-QTOF	splash10-00kf-9400000000-fea80cf888f289c0c363	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Curcumene 10V, Negative-QTOF	splash10-0udi-0090000000-0b1ac00c3b3c6c0a73b9	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Curcumene 20V, Negative-QTOF	splash10-0udi-0290000000-77743b81a0809cd73978	2021-10-11	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Curcumene 40V, Negative-QTOF	splash10-00kf-9700000000-dcc11611bd47e375b87a	2021-10-11	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

CPD-11391

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

92139

PDB ID

Not Available

ChEBI ID

62757

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

Haider SZ, Andola HC, Mohan M: Constituents of Artemisia gmelinii Weber ex Stechm. from Uttarakhand Himalaya: A Source of Artemisia Ketone. Indian J Pharm Sci. 2012 May;74(3):265-7. doi: 10.4103/0250-474X.106074. [PubMed:23439844 ]
Sato T, Hoshino H, Yoshida S, Nakajima M, Hoshino T: Bifunctional triterpene/sesquarterpene cyclase: tetraprenyl-beta-curcumene cyclase is also squalene cyclase in Bacillus megaterium. J Am Chem Soc. 2011 Nov 9;133(44):17540-3. doi: 10.1021/ja2060319. Epub 2011 Oct 13. [PubMed:21981578 ]
Afoulous S, Ferhout H, Raoelison EG, Valentin A, Moukarzel B, Couderc F, Bouajila J: Helichrysum gymnocephalum essential oil: chemical composition and cytotoxic, antimalarial and antioxidant activities, attribution of the activity origin by correlations. Molecules. 2011 Sep 29;16(10):8273-91. doi: 10.3390/molecules16108273. [PubMed:21959299 ]
Chu SS, Liu ZL, Du SS, Deng ZW: Chemical composition and insecticidal activity against Sitophilus zeamais of the essential oils derived from Artemisia giraldii and Artemisia subdigitata. Molecules. 2012 Jun 13;17(6):7255-65. doi: 10.3390/molecules17067255. [PubMed:22695231 ]
Du ZT, Zheng S, Chen G, Lv D: A short synthesis of bisabolane sesquiterpenes. Molecules. 2011 Sep 19;16(9):8053-61. doi: 10.3390/molecules16098053. [PubMed:21931286 ]
Sato T, Yoshida S, Hoshino H, Tanno M, Nakajima M, Hoshino T: Sesquarterpenes (C35 terpenes) biosynthesized via the cyclization of a linear C35 isoprenoid by a tetraprenyl-beta-curcumene synthase and a tetraprenyl-beta-curcumene cyclase: identification of a new terpene cyclase. J Am Chem Soc. 2011 Jun 29;133(25):9734-7. doi: 10.1021/ja203779h. Epub 2011 Jun 7. [PubMed:21627333 ]
Podlogar JA, Verspohl EJ: Antiinflammatory effects of ginger and some of its components in human bronchial epithelial (BEAS-2B) cells. Phytother Res. 2012 Mar;26(3):333-6. doi: 10.1002/ptr.3558. Epub 2011 Jun 23. [PubMed:21698672 ]
Caroprese Araque JF, Parra Garces MI, Arrieta Prieto D, Stashenko E: [Microscopic anatomy and volatile secondary metabolites at three stages of development of the inflorescences of Lantana camara (Verbenaceae)]. Rev Biol Trop. 2011 Mar;59(1):473-86. [PubMed:21516661 ]
Weston RJ, Smith GJ: Sesquiterpenes from the inner bark of the silver birch and the paper birch. Nat Prod Commun. 2012 Feb;7(2):145-8. [PubMed:22474938 ]
Bleeker PM, Diergaarde PJ, Ament K, Schutz S, Johne B, Dijkink J, Hiemstra H, de Gelder R, de Both MT, Sabelis MW, Haring MA, Schuurink RC: Tomato-produced 7-epizingiberene and R-curcumene act as repellents to whiteflies. Phytochemistry. 2011 Jan;72(1):68-73. doi: 10.1016/j.phytochem.2010.10.014. Epub 2010 Nov 11. [PubMed:21074818 ]
Liu ZL, He Q, Chu SS, Wang CF, Du SS, Deng ZW: Essential oil composition and larvicidal activity of Saussurea lappa roots against the mosquito Aedes albopictus (Diptera: Culicidae). Parasitol Res. 2012 Jun;110(6):2125-30. doi: 10.1007/s00436-011-2738-0. Epub 2011 Dec 14. [PubMed:22167373 ]
Lin J, Dou J, Xu J, Aisa HA: Chemical composition, antimicrobial and antitumor activities of the essential oils and crude extracts of Euphorbia macrorrhiza. Molecules. 2012 May 3;17(5):5030-9. doi: 10.3390/molecules17055030. [PubMed:22555293 ]
Afewerki S, Breistein P, Pirttila K, Deiana L, Dziedzic P, Ibrahem I, Cordova A: Catalytic enantioselective beta-alkylation of alpha,beta-unsaturated aldehydes by combination of transition-metal- and aminocatalysis: total synthesis of bisabolane sesquiterpenes. Chemistry. 2011 Aug 1;17(32):8784-8. doi: 10.1002/chem.201100756. Epub 2011 Jul 5. [PubMed:21732445 ]
Fujiwara M, Marumoto S, Yagi N, Miyazawa M: Biotransformation of turmerones by Aspergillus niger. J Nat Prod. 2011 Jan 28;74(1):86-9. doi: 10.1021/np100416v. Epub 2010 Dec 28. [PubMed:21189039 ]
Ali NA, Wursterb M, Denkert A, Arnold N, Fadail I, Al-Didamony G, Lindequist U, Wessjohann L, Setzer WN: Chemical composition, antimicrobial, antioxidant and cytotoxic activity of essential oils of Plectranthus cylindraceus and Meriandra benghalensis from Yemen. Nat Prod Commun. 2012 Aug;7(8):1099-102. [PubMed:22978239 ]
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 ]
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Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for alpha-Curcumene (HMDB0059878)

MOL for HMDB0059878 (alpha-Curcumene)

3D MOL for HMDB0059878 (alpha-Curcumene)

3D SDF for HMDB0059878 (alpha-Curcumene)

3D-SDF for HMDB0059878 (alpha-Curcumene)

PDB for HMDB0059878 (alpha-Curcumene)

3D PDB for HMDB0059878 (alpha-Curcumene)

SMILES for HMDB0059878 (alpha-Curcumene)

INCHI for HMDB0059878 (alpha-Curcumene)

Structure for HMDB0059878 (alpha-Curcumene)

3D Structure for HMDB0059878 (alpha-Curcumene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra