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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-08 15:55:52 UTC

Update Date

2022-03-07 03:17:48 UTC

HMDB ID

HMDB0061851

Secondary Accession Numbers

HMDB61851

Metabolite Identification

Common Name

alpha-Copaene

Description

alpha-Copaene, also known as aglaiene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. alpha-Copaene is possibly neutral. alpha-Copaene is a spice and woody tasting compound that can be found in several food items such as lime, mandarin orange (clementine, tangerine), safflower, and summer savoury, which makes alpha-copaene a potential biomarker for the consumption of these food products. alpha-Copaene can be found in feces and saliva.

Structure

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

HMDB0061851
     RDKit          3D
alpha-Copaene
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.1750   -1.7885    0.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1269   -1.0606    0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1039   -1.0113   -1.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2838    0.0744   -1.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3474    0.6653   -0.7800 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2211   -0.4659    0.0320 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3519   -0.0925    0.9243 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7071   -0.4684    0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7608   -1.9652    0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1406    0.2667   -0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2770    1.3353    1.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0771    1.9451    1.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0431    1.1184    0.4717 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3661    1.7637    0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0664   -0.3620    0.8696 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5110   -1.0893    1.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0394   -2.0371    0.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7895   -2.7016    1.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6382   -1.7039   -1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9662    0.8100   -2.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6490   -0.3109   -2.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3460    1.3565   -1.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3687   -1.4187   -0.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2144   -0.7253    1.8539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4389   -0.2343    1.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5535   -2.1960   -0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8228   -2.3048    0.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1396   -2.5135    0.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2620    0.3979   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7243    1.2739   -0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037   -0.3435   -1.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5563    1.4158    2.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0677    1.9551    0.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5581    2.2162    2.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0381    2.9197    0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4044    2.7697    0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1138    1.1442    0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7053    1.9278   -0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9299   -0.5623    1.9268 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15  2  1  0
 13  5  1  0
 15  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  6
  6 23  1  6
  7 24  1  1
  8 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  1
M  END


  Mrv1652309272007322D          

 15 17  0  0  0  0            999 V2000
   -2.5588    1.2580    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.6870    0.4484    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -2.0499   -0.0674    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.2846    0.2262    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.1564    1.0359    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7935    1.5518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1094    0.4879    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9095    0.2351    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9992   -0.0958    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2263    0.0770    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.2000    1.7773    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2237    1.3049    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6434   -0.2929    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1268    0.0028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7725   -1.1078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  6  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  1  6  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  3 10  1  1  0  0  0
  1 11  1  0  0  0  0
  7 12  1  0  0  0  0
  4 13  1  1  0  0  0
 13 14  1  0  0  0  0
 13 15  1  0  0  0  0
  2  7  1  1  0  0  0
 10  1  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0061851

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(C)[C@@H]1CC[C@]2(C)[C@H]3CC=C(C)[C@@H]2[C@@H]13

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h5,9,11-14H,6-8H2,1-4H3/t11-,12-,13-,14+,15+/m0/s1

> <INCHI_KEY>
VLXDPFLIRFYIME-BTFPBAQTSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
26.171244674258247

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,2S,6S,7S,8S)-1,3-dimethyl-8-(propan-2-yl)tricyclo[4.4.0.0^{2,7}]dec-3-ene

> <ALOGPS_LOGP>
3.75

> <JCHEM_LOGP>
4.0881301626666655

> <ALOGPS_LOGS>
-5.05

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
65.7679

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.81e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,2S,6S,7S,8S)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0^{2,7}]dec-3-ene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0061851
     RDKit          3D
alpha-Copaene
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.1750   -1.7885    0.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1269   -1.0606    0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1039   -1.0113   -1.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2838    0.0744   -1.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3474    0.6653   -0.7800 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2211   -0.4659    0.0320 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3519   -0.0925    0.9243 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7071   -0.4684    0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7608   -1.9652    0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1406    0.2667   -0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2770    1.3353    1.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0771    1.9451    1.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0431    1.1184    0.4717 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3661    1.7637    0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0664   -0.3620    0.8696 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5110   -1.0893    1.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0394   -2.0371    0.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7895   -2.7016    1.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6382   -1.7039   -1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9662    0.8100   -2.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6490   -0.3109   -2.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3460    1.3565   -1.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3687   -1.4187   -0.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2144   -0.7253    1.8539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4389   -0.2343    1.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5535   -2.1960   -0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8228   -2.3048    0.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1396   -2.5135    0.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2620    0.3979   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7243    1.2739   -0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037   -0.3435   -1.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5563    1.4158    2.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0677    1.9551    0.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5581    2.2162    2.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0381    2.9197    0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4044    2.7697    0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1138    1.1442    0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7053    1.9278   -0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9299   -0.5623    1.9268 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15  2  1  0
 13  5  1  0
 15  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  6
  6 23  1  6
  7 24  1  1
  8 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  1
M  END

HEADER    PROTEIN                                 27-SEP-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-SEP-20         0                                  
HETATM    1  C   UNK     0      -4.776   2.348   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.016   0.837   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -3.827  -0.126   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.398   0.422   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.159   1.934   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -3.348   2.897   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.671   0.911   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -9.164   0.439   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -7.465  -0.179   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.022   0.144   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -5.973   3.318   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -7.884   2.436   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -1.201  -0.547   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.237   0.005   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.442  -2.068   0.000  0.00  0.00           C+0
CONECT    1    2    6   11   10                                             
CONECT    2    1    3    7                                                  
CONECT    3    2    4   10                                                  
CONECT    4    3    5   13                                                  
CONECT    5    4    6                                                       
CONECT    6    5    1                                                       
CONECT    7    8   12    2                                                  
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9    3    1                                                  
CONECT   11    1                                                            
CONECT   12    7                                                            
CONECT   13    4   14   15                                                  
CONECT   14   13                                                            
CONECT   15   13                                                            
MASTER        0    0    0    0    0    0    0    0   15    0   34    0
END

COMPND    HMDB0061851
HETATM    1  C1  UNL     1       3.175  -1.789   0.904  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.127  -1.061   0.144  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.104  -1.011  -1.190  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.284   0.074  -1.796  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.347   0.665  -0.780  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.221  -0.466   0.032  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.352  -0.092   0.924  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.707  -0.468   0.405  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.761  -1.965   0.219  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.141   0.267  -0.805  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.277   1.335   1.414  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.077   1.945   1.270  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.043   1.118   0.472  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.366   1.764   0.331  1.00  0.00           C  
HETATM   15  C15 UNL     1       1.066  -0.362   0.870  1.00  0.00           C  
HETATM   16  H1  UNL     1       3.511  -1.089   1.720  1.00  0.00           H  
HETATM   17  H2  UNL     1       4.039  -2.037   0.254  1.00  0.00           H  
HETATM   18  H3  UNL     1       2.790  -2.702   1.378  1.00  0.00           H  
HETATM   19  H4  UNL     1       2.638  -1.704  -1.811  1.00  0.00           H  
HETATM   20  H5  UNL     1       1.966   0.810  -2.247  1.00  0.00           H  
HETATM   21  H6  UNL     1       0.649  -0.311  -2.632  1.00  0.00           H  
HETATM   22  H7  UNL     1      -0.346   1.357  -1.241  1.00  0.00           H  
HETATM   23  H8  UNL     1      -0.369  -1.419  -0.464  1.00  0.00           H  
HETATM   24  H9  UNL     1      -1.214  -0.725   1.854  1.00  0.00           H  
HETATM   25  H10 UNL     1      -3.439  -0.234   1.228  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.554  -2.196  -0.850  1.00  0.00           H  
HETATM   27  H12 UNL     1      -3.823  -2.305   0.390  1.00  0.00           H  
HETATM   28  H13 UNL     1      -2.140  -2.513   0.927  1.00  0.00           H  
HETATM   29  H14 UNL     1      -4.262   0.398  -0.842  1.00  0.00           H  
HETATM   30  H15 UNL     1      -2.724   1.274  -0.930  1.00  0.00           H  
HETATM   31  H16 UNL     1      -2.904  -0.343  -1.722  1.00  0.00           H  
HETATM   32  H17 UNL     1      -1.556   1.416   2.506  1.00  0.00           H  
HETATM   33  H18 UNL     1      -2.068   1.955   0.897  1.00  0.00           H  
HETATM   34  H19 UNL     1       0.558   2.216   2.235  1.00  0.00           H  
HETATM   35  H20 UNL     1      -0.038   2.920   0.712  1.00  0.00           H  
HETATM   36  H21 UNL     1       2.404   2.770   0.836  1.00  0.00           H  
HETATM   37  H22 UNL     1       3.114   1.144   0.907  1.00  0.00           H  
HETATM   38  H23 UNL     1       2.705   1.928  -0.696  1.00  0.00           H  
HETATM   39  H24 UNL     1       0.930  -0.562   1.927  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3   15
CONECT    3    4   19
CONECT    4    5   20   21
CONECT    5    6   13   22
CONECT    6    7   15   23
CONECT    7    8   11   24
CONECT    8    9   10   25
CONECT    9   26   27   28
CONECT   10   29   30   31
CONECT   11   12   32   33
CONECT   12   13   34   35
CONECT   13   14   15
CONECT   14   36   37   38
CONECT   15   39
END

HMDB0061851
     RDKit          3D
alpha-Copaene
 39 41  0  0  0  0  0  0  0  0999 V2000
    3.1750   -1.7885    0.9042 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1269   -1.0606    0.1438 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1039   -1.0113   -1.1899 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2838    0.0744   -1.7959 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3474    0.6653   -0.7800 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.2211   -0.4659    0.0320 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.3519   -0.0925    0.9243 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.7071   -0.4684    0.4048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7608   -1.9652    0.2193 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1406    0.2667   -0.8049 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2770    1.3353    1.4137 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0771    1.9451    1.2702 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0431    1.1184    0.4717 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.3661    1.7637    0.3308 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0664   -0.3620    0.8696 C   0  0  2  0  0  0  0  0  0  0  0  0
    3.5110   -1.0893    1.7205 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0394   -2.0371    0.2541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7895   -2.7016    1.3778 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6382   -1.7039   -1.8108 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9662    0.8100   -2.2468 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6490   -0.3109   -2.6316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3460    1.3565   -1.2412 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3687   -1.4187   -0.4645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2144   -0.7253    1.8539 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4389   -0.2343    1.2278 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5535   -2.1960   -0.8496 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8228   -2.3048    0.3897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1396   -2.5135    0.9271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2620    0.3979   -0.8422 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7243    1.2739   -0.9302 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9037   -0.3435   -1.7221 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5563    1.4158    2.5057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0677    1.9551    0.8970 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5581    2.2162    2.2347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0381    2.9197    0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4044    2.7697    0.8357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1138    1.1442    0.9069 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7053    1.9278   -0.6963 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9299   -0.5623    1.9268 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  8 10  1  0
  7 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  6
 13 15  1  0
 15  2  1  0
 13  5  1  0
 15  6  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  6
  6 23  1  6
  7 24  1  1
  8 25  1  0
  9 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 11 33  1  0
 12 34  1  0
 12 35  1  0
 14 36  1  0
 14 37  1  0
 14 38  1  0
 15 39  1  1
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-Copaene	Generator
Α-copaene	Generator
(-)-Copaene	HMDB
(-)-alpha-Copaene	HMDB
(-)-Α-copaene	HMDB
(1R,2S,6S,7S,8S)-(-)-8-Isopropyl-1,3-dimethyltricyclo[4.4.0.02,7]dec-3-ene	HMDB
(1R,2S,6S,7S,8S)-1,3-Dimethyl-8-(1-methylethyl)tricyclo[4.4.0.02,7]dec-3-ene	HMDB
Aglaiene	HMDB
Copaene	HMDB
alpha-Copanene	HMDB
Α-copanene	HMDB
alpha-Copaene	HMDB

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.357

Monoisotopic Molecular Weight

204.187800773

IUPAC Name

(1R,2S,6S,7S,8S)-1,3-dimethyl-8-(propan-2-yl)tricyclo[4.4.0.0^{2,7}]dec-3-ene

Traditional Name

(1R,2S,6S,7S,8S)-8-isopropyl-1,3-dimethyltricyclo[4.4.0.0^{2,7}]dec-3-ene

CAS Registry Number

3856-25-5

SMILES

CC(C)[C@@H]1CC[C@]2(C)[C@H]3CC=C(C)[C@@H]2[C@@H]13

InChI Identifier

InChI=1S/C15H24/c1-9(2)11-7-8-15(4)12-6-5-10(3)14(15)13(11)12/h5,9,11-14H,6-8H2,1-4H3/t11-,12-,13-,14+,15+/m0/s1

InChI Key

VLXDPFLIRFYIME-BTFPBAQTSA-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

Copaane sesquiterpenoid
Sesquiterpenoid
Branched unsaturated hydrocarbon
Polycyclic hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

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	0.0018 g/L	ALOGPS
logP	3.75	ALOGPS
logP	4.09	ChemAxon
logS	-5	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	65.77 m³·mol⁻¹	ChemAxon
Polarizability	26.17 Å³	ChemAxon
Number of Rings	3	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
DeepCCS	[M-2H]-	190.843	30932474
DeepCCS	[M+Na]+	165.92	30932474
AllCCS	[M+H]+	147.1	32859911
AllCCS	[M+H-H2O]+	143.2	32859911
AllCCS	[M+NH4]+	150.7	32859911
AllCCS	[M+Na]+	151.8	32859911
AllCCS	[M-H]-	158.3	32859911
AllCCS	[M+Na-2H]-	158.7	32859911
AllCCS	[M+HCOO]-	159.2	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.	6.11 minutes	32390414
Predicted by Siyang on May 30, 2022	19.3511 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.1 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2596.2 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	693.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	244.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	363.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	407.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	763.5 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	862.8 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	104.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1465.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	530.6 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	1506.7 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	505.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	459.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	455.3 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	614.0 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	8.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Copaene	CC(C)[C@@H]1CC[C@]2(C)[C@H]3CC=C(C)[C@@H]2[C@@H]13	1625.0	Standard polar	33892256
alpha-Copaene	CC(C)[C@@H]1CC[C@]2(C)[C@H]3CC=C(C)[C@@H]2[C@@H]13	1435.3	Standard non polar	33892256
alpha-Copaene	CC(C)[C@@H]1CC[C@]2(C)[C@H]3CC=C(C)[C@@H]2[C@@H]13	1422.3	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-Copaene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Copaene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Copaene 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Copaene 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Copaene 40V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Copaene 10V, Positive-QTOF	splash10-0a4i-0090000000-c084f3d998cc56a199d6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Copaene 20V, Positive-QTOF	splash10-0a4i-0090000000-3c4675614578d86c565d	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Copaene 40V, Positive-QTOF	splash10-0btd-6920000000-b4a877b11b4c0fff3460	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Feces
Saliva

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
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	23454028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	24260553	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	24130822	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	26806034	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Diarrhea-predominant IBS	23516449	details
Feces	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Autism	24130822	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Crohns disease	26806034	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	26806034	details

Associated Disorders and Diseases

Disease References

Nonalcoholic fatty liver disease
Raman M, Ahmed I, Gillevet PM, Probert CS, Ratcliffe NM, Smith S, Greenwood R, Sikaroodi M, Lam V, Crotty P, Bailey J, Myers RP, Rioux KP: Fecal microbiome and volatile organic compound metabolome in obese humans with nonalcoholic fatty liver disease. Clin Gastroenterol Hepatol. 2013 Jul;11(7):868-75.e1-3. doi: 10.1016/j.cgh.2013.02.015. Epub 2013 Feb 27. [PubMed:23454028 ]
Diarrhoea predominant irritable bowel syndrome
Ahmed I, Greenwood R, Costello Bde L, Ratcliffe NM, Probert CS: An investigation of fecal volatile organic metabolites in irritable bowel syndrome. PLoS One. 2013;8(3):e58204. doi: 10.1371/journal.pone.0058204. Epub 2013 Mar 13. [PubMed:23516449 ]
Autism
De Angelis M, Piccolo M, Vannini L, Siragusa S, De Giacomo A, Serrazzanetti DI, Cristofori F, Guerzoni ME, Gobbetti M, Francavilla R: Fecal microbiota and metabolome of children with autism and pervasive developmental disorder not otherwise specified. PLoS One. 2013 Oct 9;8(10):e76993. doi: 10.1371/journal.pone.0076993. eCollection 2013. [PubMed:24130822 ]
Crohn's disease
Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]
Ulcerative colitis
Ahmed I, Greenwood R, Costello B, Ratcliffe N, Probert CS: Investigation of faecal volatile organic metabolites as novel diagnostic biomarkers in inflammatory bowel disease. Aliment Pharmacol Ther. 2016 Mar;43(5):596-611. doi: 10.1111/apt.13522. Epub 2016 Jan 25. [PubMed:26806034 ]

Associated OMIM IDs

209850 (Autism)
266600 (Crohn's disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Copaene

METLIN ID

Not Available

PubChem Compound

12303902

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1053841

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Schreier P, Drawert F, Junker A: [Sesquiterpene hydrocarbons from grapes (author's transl)]. Z Lebensm Unters Forsch. 1976;160(3):271-4. [PubMed:983335 ]
Senatore F, Arnold NA, Piozzi F: Chemical composition of the essential oil of Salvia multicaulis Vahl. var. simplicifolia Boiss. growing wild in Lebanon. J Chromatogr A. 2004 Oct 15;1052(1-2):237-40. [PubMed:15527145 ]
Estell RE, Fredrickson EL, Anderson DM, Remmenga MD: Effects of gamma-terpinene, terpinolene, alpha-copaene, and alpha-terpinene on consumption of alfalfa pellets by sheep. J Anim Sci. 2005 Aug;83(8):1967-71. [PubMed:16024718 ]
Chaverri C, Ciccio JF: Essential oil of trees of the genus Ocotea (Lauraceae) in Costa Rica. I. Ocotea brenesii. Rev Biol Trop. 2005 Sep-Dec;53(3-4):431-6. [PubMed:17354452 ]
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.
Wikipedia [Link]
UniProt B9S9Z3 : Alpha-copaene synthase [Link]
UniProt Q4U3F6 : Alpha-copaene synthase [Link]

Showing metabocard for alpha-Copaene (HMDB0061851)

MOL for HMDB0061851 (alpha-Copaene)

3D MOL for HMDB0061851 (alpha-Copaene)

3D SDF for HMDB0061851 (alpha-Copaene)

3D-SDF for HMDB0061851 (alpha-Copaene)

PDB for HMDB0061851 (alpha-Copaene)

3D PDB for HMDB0061851 (alpha-Copaene)

SMILES for HMDB0061851 (alpha-Copaene)

INCHI for HMDB0061851 (alpha-Copaene)

Structure for HMDB0061851 (alpha-Copaene)

3D Structure for HMDB0061851 (alpha-Copaene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra