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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:18:39 UTC

Update Date

2022-03-07 02:55:10 UTC

HMDB ID

HMDB0037068

Secondary Accession Numbers

HMDB37068

Metabolite Identification

Common Name

Curlone

Description

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

Structure

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

HMDB0037068
     RDKit          3D
Curlone
 38 38  0  0  0  0  0  0  0  0999 V2000
    4.2867    2.2712    0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4521    1.2507    0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6684    0.2341   -0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7128   -0.6174   -0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4128   -0.4796   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5061   -1.6267   -0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164   -2.9581    0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8681   -1.5411    0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6391   -0.3850   -0.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1849    0.4307   -1.2020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0003   -0.1704    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7863    0.8078   -0.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1668    0.9568    0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3119    1.8037   -1.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7940   -0.2982    1.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311    1.1302    1.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1151    2.3935   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1453    3.0223    1.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6432    0.2150   -1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571   -1.3641   -1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9946    0.4821   -0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4163   -1.7016   -1.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3024   -3.7082   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9016   -3.2387   -0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4650   -2.9575    1.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4274   -2.4481   -0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9517   -1.6379    1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4250   -0.8705    0.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6513   -0.0359    0.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0858    1.3961    1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7945    1.5860   -0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1184    2.5554   -1.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    1.3255   -2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4215    2.3628   -0.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9459   -0.3658    2.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -0.9699    1.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5376    1.8304    1.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6610    1.3204    2.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  5 15  1  0
 15 16  1  0
 16  2  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
M  END


  Mrv0541 05061309332D          

 16 16  0  0  0  0            999 V2000
   -1.4289    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7145    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    2.0625    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  2  0  0  0  0
  8  6  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  9  2  0  0  0  0
 12  3  2  0  0  0  0
 12  5  1  0  0  0  0
 12  6  1  0  0  0  0
 13  4  1  0  0  0  0
 13 10  1  0  0  0  0
 14  7  1  0  0  0  0
 14  8  1  0  0  0  0
 14 13  1  0  0  0  0
 15  9  1  0  0  0  0
 15 10  1  0  0  0  0
 16 15  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037068

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CC(=O)C=C(C)C)C1CCC(=C)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O/c1-11(2)9-15(16)10-13(4)14-7-5-12(3)6-8-14/h5,7,9,13-14H,3,6,8,10H2,1-2,4H3

> <INCHI_KEY>
JIJQKFPGBBEJNF-UHFFFAOYSA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.3346

> <EXACT_MASS>
218.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.49357820934124

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-6-(4-methylidenecyclohex-2-en-1-yl)hept-2-en-4-one

> <ALOGPS_LOGP>
4.08

> <JCHEM_LOGP>
4.103712172333333

> <ALOGPS_LOGS>
-4.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.360883999458349

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
71.1676

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.56e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-6-(4-methylidenecyclohex-2-en-1-yl)hept-2-en-4-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0037068
     RDKit          3D
Curlone
 38 38  0  0  0  0  0  0  0  0999 V2000
    4.2867    2.2712    0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4521    1.2507    0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6684    0.2341   -0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7128   -0.6174   -0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4128   -0.4796   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5061   -1.6267   -0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164   -2.9581    0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8681   -1.5411    0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6391   -0.3850   -0.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1849    0.4307   -1.2020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0003   -0.1704    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7863    0.8078   -0.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1668    0.9568    0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3119    1.8037   -1.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7940   -0.2982    1.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311    1.1302    1.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1151    2.3935   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1453    3.0223    1.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6432    0.2150   -1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571   -1.3641   -1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9946    0.4821   -0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4163   -1.7016   -1.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3024   -3.7082   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9016   -3.2387   -0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4650   -2.9575    1.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4274   -2.4481   -0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9517   -1.6379    1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4250   -0.8705    0.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6513   -0.0359    0.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0858    1.3961    1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7945    1.5860   -0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1184    2.5554   -1.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    1.3255   -2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4215    2.3628   -0.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9459   -0.3658    2.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -0.9699    1.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5376    1.8304    1.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6610    1.3204    2.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  5 15  1  0
 15 16  1  0
 16  2  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0      -2.667   9.240   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.000   9.240   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.540   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.334   6.930   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.000   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.334   8.470   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       1.334   3.850   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       1.334   2.310   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.000   6.160   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       1.334   6.930   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   13                                                            
CONECT    5    7   12                                                       
CONECT    6    8   12                                                       
CONECT    7    5   14                                                       
CONECT    8    6   14                                                       
CONECT    9   11   15                                                       
CONECT   10   13   15                                                       
CONECT   11    1    2    9                                                  
CONECT   12    3    5    6                                                  
CONECT   13    4   10   14                                                  
CONECT   14    7    8   13                                                  
CONECT   15    9   10   16                                                  
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   32    0
END

COMPND    HMDB0037068
HETATM    1  C1  UNL     1       4.287   2.271   0.591  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.452   1.251   0.530  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.668   0.234  -0.518  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.713  -0.617  -0.853  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.413  -0.480  -0.104  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.506  -1.627  -0.375  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.116  -2.958   0.036  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.868  -1.541   0.158  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.639  -0.385  -0.369  1.00  0.00           C  
HETATM   10  O1  UNL     1      -1.185   0.431  -1.202  1.00  0.00           O  
HETATM   11  C10 UNL     1      -3.000  -0.170   0.098  1.00  0.00           C  
HETATM   12  C11 UNL     1      -3.786   0.808  -0.287  1.00  0.00           C  
HETATM   13  C12 UNL     1      -5.167   0.957   0.238  1.00  0.00           C  
HETATM   14  C13 UNL     1      -3.312   1.804  -1.270  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.794  -0.298   1.334  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.331   1.130   1.488  1.00  0.00           C  
HETATM   17  H1  UNL     1       5.115   2.393  -0.089  1.00  0.00           H  
HETATM   18  H2  UNL     1       4.145   3.022   1.348  1.00  0.00           H  
HETATM   19  H3  UNL     1       4.643   0.215  -1.002  1.00  0.00           H  
HETATM   20  H4  UNL     1       2.857  -1.364  -1.616  1.00  0.00           H  
HETATM   21  H5  UNL     1       0.995   0.482  -0.457  1.00  0.00           H  
HETATM   22  H6  UNL     1       0.416  -1.702  -1.501  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.302  -3.708  -0.071  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.902  -3.239  -0.691  1.00  0.00           H  
HETATM   25  H9  UNL     1       1.465  -2.957   1.084  1.00  0.00           H  
HETATM   26  H10 UNL     1      -1.427  -2.448  -0.231  1.00  0.00           H  
HETATM   27  H11 UNL     1      -0.952  -1.638   1.257  1.00  0.00           H  
HETATM   28  H12 UNL     1      -3.425  -0.870   0.830  1.00  0.00           H  
HETATM   29  H13 UNL     1      -5.651  -0.036   0.371  1.00  0.00           H  
HETATM   30  H14 UNL     1      -5.086   1.396   1.254  1.00  0.00           H  
HETATM   31  H15 UNL     1      -5.795   1.586  -0.408  1.00  0.00           H  
HETATM   32  H16 UNL     1      -4.118   2.555  -1.499  1.00  0.00           H  
HETATM   33  H17 UNL     1      -3.049   1.326  -2.234  1.00  0.00           H  
HETATM   34  H18 UNL     1      -2.421   2.363  -0.914  1.00  0.00           H  
HETATM   35  H19 UNL     1       0.946  -0.366   2.035  1.00  0.00           H  
HETATM   36  H20 UNL     1       2.617  -0.970   1.653  1.00  0.00           H  
HETATM   37  H21 UNL     1       1.538   1.830   1.166  1.00  0.00           H  
HETATM   38  H22 UNL     1       2.661   1.320   2.529  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3   16
CONECT    3    4    4   19
CONECT    4    5   20
CONECT    5    6   15   21
CONECT    6    7    8   22
CONECT    7   23   24   25
CONECT    8    9   26   27
CONECT    9   10   10   11
CONECT   11   12   12   28
CONECT   12   13   14
CONECT   13   29   30   31
CONECT   14   32   33   34
CONECT   15   16   35   36
CONECT   16   37   38
END

HMDB0037068
     RDKit          3D
Curlone
 38 38  0  0  0  0  0  0  0  0999 V2000
    4.2867    2.2712    0.5906 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4521    1.2507    0.5301 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6684    0.2341   -0.5183 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7128   -0.6174   -0.8532 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4128   -0.4796   -0.1038 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5061   -1.6267   -0.3750 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1164   -2.9581    0.0363 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8681   -1.5411    0.1577 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6391   -0.3850   -0.3686 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1849    0.4307   -1.2020 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0003   -0.1704    0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7863    0.8078   -0.2870 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1668    0.9568    0.2383 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3119    1.8037   -1.2695 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7940   -0.2982    1.3338 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3311    1.1302    1.4877 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1151    2.3935   -0.0894 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1453    3.0223    1.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6432    0.2150   -1.0022 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8571   -1.3641   -1.6163 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9946    0.4821   -0.4566 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4163   -1.7016   -1.5013 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3024   -3.7082   -0.0711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9016   -3.2387   -0.6912 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4650   -2.9575    1.0843 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4274   -2.4481   -0.2310 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9517   -1.6379    1.2575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4250   -0.8705    0.8304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6513   -0.0359    0.3711 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0858    1.3961    1.2543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7945    1.5860   -0.4078 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1184    2.5554   -1.4991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0493    1.3255   -2.2344 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4215    2.3628   -0.9139 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9459   -0.3658    2.0354 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6167   -0.9699    1.6535 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5376    1.8304    1.1656 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6610    1.3204    2.5287 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  2  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  2  0
  9 11  1  0
 11 12  2  3
 12 13  1  0
 12 14  1  0
  5 15  1  0
 15 16  1  0
 16  2  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  6 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
 11 28  1  0
 13 29  1  0
 13 30  1  0
 13 31  1  0
 14 32  1  0
 14 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 16 37  1  0
 16 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,3(15),10-Bisabolatrien-9-one	HMDB
b-Turmerone	HMDB
beta-Turmerone	HMDB, MeSH
[S-(R,r)]-2-methyl-6-(4-methylene-2-cyclohexen-1-yl)-2-hepten-4-one	HMDB

Chemical Formula

C₁₅H₂₂O

Average Molecular Weight

218.3346

Monoisotopic Molecular Weight

218.167065326

IUPAC Name

2-methyl-6-(4-methylidenecyclohex-2-en-1-yl)hept-2-en-4-one

Traditional Name

2-methyl-6-(4-methylidenecyclohex-2-en-1-yl)hept-2-en-4-one

CAS Registry Number

87440-60-6

SMILES

CC(CC(=O)C=C(C)C)C1CCC(=C)C=C1

InChI Identifier

InChI=1S/C15H22O/c1-11(2)9-15(16)10-13(4)14-7-5-12(3)6-8-14/h5,7,9,13-14H,3,6,8,10H2,1-2,4H3

InChI Key

JIJQKFPGBBEJNF-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
Alpha,beta-unsaturated ketone
Enone
Acryloyl-group
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0037068)
Cell membrane (HMDB: HMDB0037068)

Cellular substructure

Extracellular (HMDB: HMDB0037068)
Membrane (HMDB: HMDB0037068)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037068)

Source

Endogenous

Endogenous (HMDB: HMDB0037068)

Plant

Plant (HMDB: HMDB0037068)

Animal

Animal (HMDB: HMDB0037068)

Exogenous

Food

Food (HMDB: HMDB0037068)

Herb and spice

Spice

Turmeric (FooDB: FOOD00068)

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0037068)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0037068)

Cellular process

Cell signaling (HMDB: HMDB0037068)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0037068)

cyclooxygenase 2 inhibitor (HMDB: HMDB0037068)
iNOS inhibitor (HMDB: HMDB0037068)

Nutrient

Nutrient (HMDB: HMDB0037068)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037068)

Emulsifier (HMDB: HMDB0037068)

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	1.19 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	4.08	ALOGPS
logP	4.1	ChemAxon
logS	-4.2	ALOGPS
pKa (Strongest Basic)	-4.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	71.17 m³·mol⁻¹	ChemAxon
Polarizability	26.49 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	153.825	31661259
DarkChem	[M-H]-	152.623	31661259
DeepCCS	[M+H]+	157.158	30932474
DeepCCS	[M-H]-	154.8	30932474
DeepCCS	[M-2H]-	187.827	30932474
DeepCCS	[M+Na]+	163.251	30932474
AllCCS	[M+H]+	152.8	32859911
AllCCS	[M+H-H2O]+	148.9	32859911
AllCCS	[M+NH4]+	156.4	32859911
AllCCS	[M+Na]+	157.4	32859911
AllCCS	[M-H]-	158.8	32859911
AllCCS	[M+Na-2H]-	159.5	32859911
AllCCS	[M+HCOO]-	160.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Curlone	CC(CC(=O)C=C(C)C)C1CCC(=C)C=C1	2330.2	Standard polar	33892256
Curlone	CC(CC(=O)C=C(C)C)C1CCC(=C)C=C1	1655.6	Standard non polar	33892256
Curlone	CC(CC(=O)C=C(C)C)C1CCC(=C)C=C1	1659.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Curlone,1TMS,isomer #1	C=C1C=CC(C(C)C=C(C=C(C)C)O[Si](C)(C)C)CC1	1891.6	Semi standard non polar	33892256
Curlone,1TMS,isomer #1	C=C1C=CC(C(C)C=C(C=C(C)C)O[Si](C)(C)C)CC1	1746.3	Standard non polar	33892256
Curlone,1TBDMS,isomer #1	C=C1C=CC(C(C)C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C)CC1	2105.7	Semi standard non polar	33892256
Curlone,1TBDMS,isomer #1	C=C1C=CC(C(C)C=C(C=C(C)C)O[Si](C)(C)C(C)(C)C)CC1	1986.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Curlone GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9210000000-b2197b6f1a746a9e50a7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Curlone 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 - Curlone 10V, Positive-QTOF	splash10-014i-1390000000-06976808be91360fa26f	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curlone 20V, Positive-QTOF	splash10-00m3-8930000000-b3cbb70705fc5b1e4b98	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curlone 40V, Positive-QTOF	splash10-0zir-9200000000-c69249db7bf30f834362	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curlone 10V, Negative-QTOF	splash10-014i-1190000000-ddce2d4b78c32fc7888c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curlone 20V, Negative-QTOF	splash10-066r-9570000000-383af50a796757dd53e6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curlone 40V, Negative-QTOF	splash10-0a4i-9400000000-b9f98bb7b7a39369de54	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curlone 10V, Positive-QTOF	splash10-00di-6900000000-91e5d5362ffdcc195202	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curlone 20V, Positive-QTOF	splash10-000x-9500000000-0f2d03fed0080994ed56	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curlone 40V, Positive-QTOF	splash10-0006-9100000000-771c6ffd66f137da4ef8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curlone 10V, Negative-QTOF	splash10-014i-0090000000-868e2fb00a2cfbf6c529	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curlone 20V, Negative-QTOF	splash10-0159-4940000000-a8b06f9c9198eae9dcaf	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Curlone 40V, Negative-QTOF	splash10-014i-9730000000-6fdc3a3050cbcf0e5b2f	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB016052

KNApSAcK ID

C00011640

Chemspider ID

170035

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

196216

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1859061

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Curlone (HMDB0037068)

MOL for HMDB0037068 (Curlone)

3D MOL for HMDB0037068 (Curlone)

3D SDF for HMDB0037068 (Curlone)

3D-SDF for HMDB0037068 (Curlone)

PDB for HMDB0037068 (Curlone)

3D PDB for HMDB0037068 (Curlone)

SMILES for HMDB0037068 (Curlone)

INCHI for HMDB0037068 (Curlone)

Structure for HMDB0037068 (Curlone)

3D Structure for HMDB0037068 (Curlone)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra