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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2013-03-07 21:36:15 UTC

Update Date

2021-09-14 15:45:23 UTC

HMDB ID

HMDB0059910

Secondary Accession Numbers

HMDB59910

Metabolite Identification

Common Name

(E)-Calamene

Description

Calamene is a metabolite of plant Turnera diffusa. Turnera diffusa (Damiana, Mexican holly, Old Woman's Broom) is a small shrub of the family Tuneraceae. T. diffusa is native to both Central and South America and now commercially cultivated in Bolivia and Mexico. The leaf includes volatile oils (1,8-cineole, p-cymene, alpha- and beta-pinene, thymol, alpha-copaene, and calamene); luteolin; tannins, flavonoids (arbutin, acacetin, apigenin and pinocembrin), beta-sitosterol, damianin, and the cyanogenic glycoside tetraphyllin B. (www.globinmed.com)

Structure

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

HMDB0059910
     RDKit          3D
(E)-Calamene
 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.5041    3.7770   -0.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5204    2.3304   -0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6667    1.5525   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6231    0.1986   -0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4308   -0.3470    0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596    0.3923    0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3371    1.7274   -0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9541   -0.2932    0.6742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2278    0.4524    0.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641   -0.4524    0.9629 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5311    0.7441   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1068   -1.6634    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865   -2.3323   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982   -1.7834    0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5790   -2.5509    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9186    4.0025   -1.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1433    4.3094    0.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5565    4.0785   -0.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5844    2.0149   -0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5319   -0.3859   -0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5540    2.3025   -0.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745   -0.4828    1.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3250    1.3758    1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4096   -1.3969    0.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128   -0.5239    2.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3018    0.1298    0.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6235    0.8538   -1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765    1.7075   -1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370   -0.0189   -1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6403   -2.3514    0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7260   -1.6354   -0.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568   -2.0855   -1.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1469   -3.4293   -0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451   -1.8174    1.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4360   -2.0924    0.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4195   -3.5430    0.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7204   -2.7636   -0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  7  2  1  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  7 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
M  END


  Mrv0541 02241221002D          

 15 16  0  0  0  0            999 V2000
   -0.7145   -0.4125    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   -1.6500    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
    0.7145   -0.4125    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    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289   -1.6500    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
    0.7145   -2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -2.8875    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
   -1.4289   -1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  2  3  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  2  0  0  0  0
  1  6  1  0  0  0  0
  5  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  4 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 11 13  1  0  0  0  0
  7 14  1  0  0  0  0
  2 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059910

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)C1CCC(C)C2=CC=C(C)C=C12

> <INCHI_IDENTIFIER>
InChI=1S/C15H22/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5,7,9-10,12-13H,6,8H2,1-4H3

> <INCHI_KEY>
PGTJIOWQJWHTJJ-UHFFFAOYSA-N

> <FORMULA>
C15H22

> <MOLECULAR_WEIGHT>
202.3352

> <EXACT_MASS>
202.172150704

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_AVERAGE_POLARIZABILITY>
25.69360042899453

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,6-dimethyl-4-(propan-2-yl)-1,2,3,4-tetrahydronaphthalene

> <ALOGPS_LOGP>
5.60

> <JCHEM_LOGP>
5.244547365333334

> <ALOGPS_LOGS>
-6.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0

> <JCHEM_REFRACTIVITY>
66.8282

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.57e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4-isopropyl-1,6-dimethyl-1,2,3,4-tetrahydronaphthalene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0059910
     RDKit          3D
(E)-Calamene
 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.5041    3.7770   -0.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5204    2.3304   -0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6667    1.5525   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6231    0.1986   -0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4308   -0.3470    0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596    0.3923    0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3371    1.7274   -0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9541   -0.2932    0.6742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2278    0.4524    0.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641   -0.4524    0.9629 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5311    0.7441   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1068   -1.6634    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865   -2.3323   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982   -1.7834    0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5790   -2.5509    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9186    4.0025   -1.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1433    4.3094    0.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5565    4.0785   -0.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5844    2.0149   -0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5319   -0.3859   -0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5540    2.3025   -0.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745   -0.4828    1.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3250    1.3758    1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4096   -1.3969    0.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128   -0.5239    2.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3018    0.1298    0.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6235    0.8538   -1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765    1.7075   -1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370   -0.0189   -1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6403   -2.3514    0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7260   -1.6354   -0.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568   -2.0855   -1.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1469   -3.4293   -0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451   -1.8174    1.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4360   -2.0924    0.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4195   -3.5430    0.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7204   -2.7636   -0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  7  2  1  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  7 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -1.334  -0.770   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       0.000  -3.080   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.334  -0.770   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   0.000   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -2.310   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.667  -3.080   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       2.667  -4.620   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.334  -5.390   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       4.001  -5.390   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -2.667  -3.080   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1    3   15                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5   10                                                  
CONECT    5    4    6    7                                                  
CONECT    6    5    1                                                       
CONECT    7    5    8   14                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    4   11                                                  
CONECT   11   10   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    7                                                            
CONECT   15    2                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   32    0
END

COMPND    HMDB0059910
HETATM    1  C1  UNL     1      -1.504   3.777  -0.775  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.520   2.330  -0.440  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.667   1.553  -0.491  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.623   0.199  -0.166  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.431  -0.347   0.203  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.260   0.392   0.268  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.337   1.727  -0.060  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.954  -0.293   0.674  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.228   0.452   0.469  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.364  -0.452   0.963  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.531   0.744  -0.975  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.107  -1.663   0.050  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.187  -2.332  -0.295  1.00  0.00           C  
HETATM   14  C14 UNL     1      -1.298  -1.783   0.565  1.00  0.00           C  
HETATM   15  C15 UNL     1      -2.579  -2.551   0.411  1.00  0.00           C  
HETATM   16  H1  UNL     1      -0.919   4.002  -1.685  1.00  0.00           H  
HETATM   17  H2  UNL     1      -1.143   4.309   0.125  1.00  0.00           H  
HETATM   18  H3  UNL     1      -2.556   4.078  -0.955  1.00  0.00           H  
HETATM   19  H4  UNL     1      -3.584   2.015  -0.785  1.00  0.00           H  
HETATM   20  H5  UNL     1      -3.532  -0.386  -0.213  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.554   2.302  -0.014  1.00  0.00           H  
HETATM   22  H7  UNL     1       0.874  -0.483   1.786  1.00  0.00           H  
HETATM   23  H8  UNL     1       2.325   1.376   1.048  1.00  0.00           H  
HETATM   24  H9  UNL     1       3.410  -1.397   0.424  1.00  0.00           H  
HETATM   25  H10 UNL     1       3.313  -0.524   2.054  1.00  0.00           H  
HETATM   26  H11 UNL     1       4.302   0.130   0.736  1.00  0.00           H  
HETATM   27  H12 UNL     1       1.623   0.854  -1.600  1.00  0.00           H  
HETATM   28  H13 UNL     1       3.076   1.708  -1.051  1.00  0.00           H  
HETATM   29  H14 UNL     1       3.237  -0.019  -1.414  1.00  0.00           H  
HETATM   30  H15 UNL     1       1.640  -2.351   0.771  1.00  0.00           H  
HETATM   31  H16 UNL     1       1.726  -1.635  -0.869  1.00  0.00           H  
HETATM   32  H17 UNL     1      -0.457  -2.086  -1.361  1.00  0.00           H  
HETATM   33  H18 UNL     1      -0.147  -3.429  -0.141  1.00  0.00           H  
HETATM   34  H19 UNL     1      -0.945  -1.817   1.617  1.00  0.00           H  
HETATM   35  H20 UNL     1      -3.436  -2.092   0.895  1.00  0.00           H  
HETATM   36  H21 UNL     1      -2.419  -3.543   0.896  1.00  0.00           H  
HETATM   37  H22 UNL     1      -2.720  -2.764  -0.667  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3    7
CONECT    3    4   19
CONECT    4    5    5   20
CONECT    5    6   14
CONECT    6    7    7    8
CONECT    7   21
CONECT    8    9   12   22
CONECT    9   10   11   23
CONECT   10   24   25   26
CONECT   11   27   28   29
CONECT   12   13   30   31
CONECT   13   14   32   33
CONECT   14   15   34
CONECT   15   35   36   37
END

HMDB0059910
     RDKit          3D
(E)-Calamene
 37 38  0  0  0  0  0  0  0  0999 V2000
   -1.5041    3.7770   -0.7748 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5204    2.3304   -0.4402 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6667    1.5525   -0.4907 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6231    0.1986   -0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4308   -0.3470    0.2032 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596    0.3923    0.2678 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3371    1.7274   -0.0597 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9541   -0.2932    0.6742 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2278    0.4524    0.4689 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.3641   -0.4524    0.9629 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5311    0.7441   -0.9746 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1068   -1.6634    0.0503 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1865   -2.3323   -0.2949 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2982   -1.7834    0.5647 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5790   -2.5509    0.4111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9186    4.0025   -1.6849 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1433    4.3094    0.1254 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5565    4.0785   -0.9547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5844    2.0149   -0.7846 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5319   -0.3859   -0.2134 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5540    2.3025   -0.0135 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8745   -0.4828    1.7863 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3250    1.3758    1.0475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4096   -1.3969    0.4237 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3128   -0.5239    2.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3018    0.1298    0.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6235    0.8538   -1.6001 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0765    1.7075   -1.0512 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2370   -0.0189   -1.4144 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6403   -2.3514    0.7707 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7260   -1.6354   -0.8688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4568   -2.0855   -1.3610 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1469   -3.4293   -0.1408 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9451   -1.8174    1.6169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4360   -2.0924    0.8954 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4195   -3.5430    0.8958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7204   -2.7636   -0.6667 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
  9 11  1  0
  8 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
  7  2  1  0
 14  5  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  7 21  1  0
  8 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
 11 27  1  0
 11 28  1  0
 11 29  1  0
 12 30  1  0
 12 31  1  0
 13 32  1  0
 13 33  1  0
 14 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
1,6-Dimethyl-4-isopropyltetralin	HMDB
1,6-Dimethyl-4-propan-2-yl-1,2,3,4-tetrahydronaphthalene	HMDB
Calamenene	MeSH
(7R,10R)-Calamenene	MeSH

Chemical Formula

C₁₅H₂₂

Average Molecular Weight

202.3352

Monoisotopic Molecular Weight

202.172150704

IUPAC Name

1,6-dimethyl-4-(propan-2-yl)-1,2,3,4-tetrahydronaphthalene

Traditional Name

4-isopropyl-1,6-dimethyl-1,2,3,4-tetrahydronaphthalene

CAS Registry Number

1406-50-4

SMILES

CC(C)C1CCC(C)C2=CC=C(C)C=C12

InChI Identifier

InChI=1S/C15H22/c1-10(2)13-8-6-12(4)14-7-5-11(3)9-15(13)14/h5,7,9-10,12-13H,6,8H2,1-4H3

InChI Key

PGTJIOWQJWHTJJ-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

Sesquiterpenoid
Cadinane sesquiterpenoid
Tetralin
Benzenoid
Aromatic hydrocarbon
Polycyclic hydrocarbon
Unsaturated hydrocarbon
Hydrocarbon
Aromatic homopolycyclic compound

Molecular Framework

Aromatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (PMID: 24023812)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0059910)

Source

Endogenous

Endogenous (HMDB: HMDB0059910)

Animal

Animal (HMDB: HMDB0059910)

Exogenous

Food

Food (HMDB: HMDB0059910)

Grape (FooDB: FOOD00369)

Tropical fruit

Guava (FooDB: FOOD00150)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0059910)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0059910)

Lipid metabolism pathway (HMDB: HMDB0059910)

Cellular process

Cell signaling (HMDB: HMDB0059910)

Biochemical process

Lipid transport (HMDB: HMDB0059910)

Role

Biological role

Energy source (HMDB: HMDB0059910)

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	0.00016 g/L	ALOGPS
logP	5.6	ALOGPS
logP	5.24	ChemAxon
logS	-6.1	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	66.83 m³·mol⁻¹	ChemAxon
Polarizability	25.69 Å³	ChemAxon
Number of Rings	2	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]+	148.389	31661259
DarkChem	[M-H]-	143.85	31661259
DeepCCS	[M-2H]-	184.459	30932474
DeepCCS	[M+Na]+	159.997	30932474
AllCCS	[M+H]+	144.3	32859911
AllCCS	[M+H-H2O]+	140.2	32859911
AllCCS	[M+NH4]+	148.2	32859911
AllCCS	[M+Na]+	149.3	32859911
AllCCS	[M-H]-	154.9	32859911
AllCCS	[M+Na-2H]-	155.2	32859911
AllCCS	[M+HCOO]-	155.7	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.	8.36 minutes	32390414
Predicted by Siyang on May 30, 2022	21.0477 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.78 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2421.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	754.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	281.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	469.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	437.5 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	986.0 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	882.4 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	149.2 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1829.1 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	689.4 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1915.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	638.0 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	477.4 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	493.1 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	541.8 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
(E)-Calamene	CC(C)C1CCC(C)C2=CC=C(C)C=C12	1766.1	Standard polar	33892256
(E)-Calamene	CC(C)C1CCC(C)C2=CC=C(C)C=C12	1489.5	Standard non polar	33892256
(E)-Calamene	CC(C)C1CCC(C)C2=CC=C(C)C=C12	1520.7	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 - (E)-Calamene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-1900000000-e2eb7825acd61ff8730a	2017-09-20	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (E)-Calamene 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 - (E)-Calamene 10V, Positive-QTOF	splash10-0udi-0290000000-3833d3353a63006060a0	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Calamene 20V, Positive-QTOF	splash10-0pba-5920000000-aeba5b60d7356802a8ca	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Calamene 40V, Positive-QTOF	splash10-0670-9700000000-812a7722433301fdc32d	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Calamene 10V, Negative-QTOF	splash10-0udi-0090000000-54b3223e470f6dfbf6d1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Calamene 20V, Negative-QTOF	splash10-0udi-0090000000-137b222230d90faadf01	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Calamene 40V, Negative-QTOF	splash10-0kg9-0910000000-daf126c6cab0a4419b5d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Calamene 10V, Positive-QTOF	splash10-0udi-0690000000-465d1e62b91a23dd1b22	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Calamene 20V, Positive-QTOF	splash10-0006-9620000000-2a3ae08008386dead200	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Calamene 40V, Positive-QTOF	splash10-0006-9200000000-9676c61135ebdcd2e09e	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Calamene 10V, Negative-QTOF	splash10-0udi-0090000000-0b1ac00c3b3c6c0a73b9	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Calamene 20V, Negative-QTOF	splash10-0udi-0090000000-e36b31b780642666a763	2021-10-12	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (E)-Calamene 40V, Negative-QTOF	splash10-052f-0900000000-c435c46e2d5fabf5807c	2021-10-12	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Membrane (predicted from logP)

Biospecimen Locations

Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24023812	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

FDB003841

KNApSAcK ID

Not Available

Chemspider ID

9807

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

10224

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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

Showing metabocard for (E)-Calamene (HMDB0059910)

MOL for HMDB0059910 ((E)-Calamene)

3D MOL for HMDB0059910 ((E)-Calamene)

3D SDF for HMDB0059910 ((E)-Calamene)

3D-SDF for HMDB0059910 ((E)-Calamene)

PDB for HMDB0059910 ((E)-Calamene)

3D PDB for HMDB0059910 ((E)-Calamene)

SMILES for HMDB0059910 ((E)-Calamene)

INCHI for HMDB0059910 ((E)-Calamene)

Structure for HMDB0059910 ((E)-Calamene)

3D Structure for HMDB0059910 ((E)-Calamene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra