Hmdb loader

Showing metabocard for alpha-Curcumene (HMDB0059878)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-03-07 21:34:33 UTC
Update Date2022-03-07 03:17:37 UTC
HMDB IDHMDB0059878
Secondary Accession Numbers
  • HMDB59878
Metabolite Identification
Common Namealpha-Curcumene
Descriptionalpha-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
Data?1563865986
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0059878 (alpha-Curcumene)

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
Download

3D MOL for HMDB0059878 (alpha-Curcumene)

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
Download

3D SDF for HMDB0059878 (alpha-Curcumene)

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

$$$$
Download

3D-SDF for HMDB0059878 (alpha-Curcumene)

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
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PDB for HMDB0059878 (alpha-Curcumene)

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
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3D PDB for HMDB0059878 (alpha-Curcumene)

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
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SMILES for HMDB0059878 (alpha-Curcumene)

CC(CCC=C(C)C)C1=CC=C(C)C=C1
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INCHI for HMDB0059878 (alpha-Curcumene)

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
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View in JSmolView Stereo Labels
Synonyms
ValueSource
1-(1,5-Dimethyl-4-hexenyl)-4-methylbenzeneChEBI
2-Methyl-6-p-tolyl-2-hepteneChEBI
Ar-curcumeneChEBI
Aromatic curcumeneChEBI
Aryl-curcumeneChEBI
CurcumeneChEBI
a-CurcumeneGenerator
Α-curcumeneGenerator
(S)-Isomer OF alpha-curcumeneHMDB
(R)-Isomer OF alpha-curcumeneHMDB
Chemical FormulaC15H22
Average Molecular Weight202.341
Monoisotopic Molecular Weight202.172150708
IUPAC Name1-methyl-4-(6-methylhept-5-en-2-yl)benzene
Traditional Namecurcumene
CAS Registry NumberNot 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 KeyVMYXUZSZMNBRCN-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
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 FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Not AvailableNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.00099 g/LALOGPS
logP6.15ALOGPS
logP5.39ChemAxon
logS-5.3ALOGPS
Physiological Charge0ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count4ChemAxon
Refractivity69.09 m³·mol⁻¹ChemAxon
Polarizability26.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveNoChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+151.02131661259
DarkChem[M-H]-147.64831661259
DeepCCS[M+H]+153.3330932474
DeepCCS[M-H]-150.97230932474
DeepCCS[M-2H]-185.81630932474
DeepCCS[M+Na]+160.830932474
AllCCS[M+H]+146.332859911
AllCCS[M+H-H2O]+142.232859911
AllCCS[M+NH4]+150.132859911
AllCCS[M+Na]+151.232859911
AllCCS[M-H]-152.232859911
AllCCS[M+Na-2H]-152.732859911
AllCCS[M+HCOO]-153.332859911

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
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 minutes32390414
Predicted by Siyang on May 30, 202220.799 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.59 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2703.4 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid725.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid280.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid456.9 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid391.5 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid896.0 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid832.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)105.3 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1841.4 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid748.0 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1647.3 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid625.3 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid513.8 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate474.2 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA507.1 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water7.9 seconds40023050

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
alpha-CurcumeneCC(CCC=C(C)C)C1=CC=C(C)C=C11889.7Standard polar33892256
alpha-CurcumeneCC(CCC=C(C)C)C1=CC=C(C)C=C11471.5Standard non polar33892256
alpha-CurcumeneCC(CCC=C(C)C)C1=CC=C(C)C=C11466.5Semi standard non polar33892256
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDCPD-11391
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound92139
PDB IDNot Available
ChEBI ID62757
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. 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 ]
  6. 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 ]
  7. 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 ]
  8. 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 ]
  9. 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 ]
  10. 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 ]
  11. 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 ]
  12. 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 ]
  13. 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 ]
  14. 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 ]
  15. 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 ]
  16. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  17. 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 ]
  18. 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 ]
  19. 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 ]
  20. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.