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Showing metabocard for Camphene (HMDB0059839)

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Record Information
Version5.0
StatusDetected but not Quantified
Creation Date2013-03-07 21:32:21 UTC
Update Date2021-09-14 15:45:25 UTC
HMDB IDHMDB0059839
Secondary Accession Numbers
  • HMDB59839
Metabolite Identification
Common NameCamphene
DescriptionCamphene, also known as 2,2-dimethyl-3-methylenebicyclo[2.2.1]heptane or 2,2-dimethyl-3-methylenenorbornane, is a member of the class of compounds known as bicyclic monoterpenoids. Bicyclic monoterpenoids are monoterpenoids containing exactly 2 rings, which are fused to each other. Monoterpenoids are terpenes that contain 10 carbon atoms and are comprised of two isoprene units. The biosynthesis of monoterpenes is known to occur mainly through the methyl-erythritol-phosphate (MEP) pathway in plastids (PMID:7640522 ). Geranyl diphosphate (GPP) is a key intermediate in the biosynthesis of cyclic monoterpenes. GPP undergoes several cyclization reactions to yield a diverse number of cyclic arrangements. Camphene is nearly insoluble in water but very soluble in common organic solvents. It volatilizes readily at room temperature and has a pungent smell. It exists as a flammable, white solid that has a minty, citrus, eucalyptus odor. It is produced industrially by catalytic isomerization of the more common alpha-pinene. Camphene is used in the preparation of fragrances and in food additives for flavouring. In the mid-19th century it was used as a fuel for lamps, but this was limited by its explosiveness. Camphene exists in all eukaryotes, ranging from yeast to plants to humans. Camphene can be found in a number of food items such as dill, carrots, caraway, hyssop, lemon, orange, nutmeg seed, parsley, sage, thyme, turmeric and fennel, which makes camphene a potential biomarker for the consumption of these food products. It is a minor constituent of many essential oils such as turpentine, cypress oil, camphor oil, citronella oil, neroli, ginger oil, and valerian. Camphene is one of several monoterpenes that are found in cannabis plants (PMID:6991645 ).
Structure
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0059839 (Camphene)

camphene
  Mrv1652305271900052D          

 10 11  0  0  0  0            999 V2000
    0.2522   -2.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1351   -2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6764   -1.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106   -1.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6411   -2.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9362   -1.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1407   -0.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004   -1.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1135   -0.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
Download

3D MOL for HMDB0059839 (Camphene)

HMDB0059839
     RDKit          3D
Camphene
 26 27  0  0  0  0  0  0  0  0999 V2000
   -0.3016    1.4991    1.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0025    0.5043    0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2873   -0.2134    0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1282    0.4573   -0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1926    0.2775   -1.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1814   -0.7448   -1.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9378   -1.4962    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8757   -0.0881   -0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7614   -1.1037    0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6652    0.9380   -0.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4262    1.8400    2.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2781    1.9745    1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7797   -0.3906    1.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785   -0.0942   -0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2637    1.5064    0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7178    1.2605   -1.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7762    0.0070   -2.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083   -1.3790   -1.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361   -1.9867   -0.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2794   -2.1475    0.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8358   -2.0598   -0.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4557   -1.3580    1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835   -0.6376    0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547    1.8851   -1.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8940    0.4971   -1.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6684    1.0527   -0.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
  8  2  1  0
  7  3  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
M  END
Download

3D SDF for HMDB0059839 (Camphene)

camphene
  Mrv1652305271900052D          

 10 11  0  0  0  0            999 V2000
    0.2522   -2.8768    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1351   -2.0602    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6764   -1.9114    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9106   -1.6699    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6411   -2.0402    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9362   -1.4148    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1407   -0.9495    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9807   -0.1341    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5004   -1.3997    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1135   -0.8486    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  4  8  1  0  0  0  0
  7  9  1  0  0  0  0
  2  9  1  0  0  0  0
  9 10  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0059839

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)C2CCC(C2)C1=C

> <INCHI_IDENTIFIER>
InChI=1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3

> <INCHI_KEY>
CRPUJAZIXJMDBK-UHFFFAOYSA-N

> <FORMULA>
C10H16

> <MOLECULAR_WEIGHT>
136.238

> <EXACT_MASS>
136.125200515

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
26

> <JCHEM_AVERAGE_POLARIZABILITY>
16.951074738158884

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2,2-dimethyl-3-methylidenebicyclo[2.2.1]heptane

> <ALOGPS_LOGP>
4.56

> <JCHEM_LOGP>
2.859595116666666

> <ALOGPS_LOGS>
-3.34

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
43.6498

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.21e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
camphene

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0059839 (Camphene)

HMDB0059839
     RDKit          3D
Camphene
 26 27  0  0  0  0  0  0  0  0999 V2000
   -0.3016    1.4991    1.7814 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0025    0.5043    0.9315 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2873   -0.2134    0.8762 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1282    0.4573   -0.1943 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1926    0.2775   -1.4024 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1814   -0.7448   -1.0104 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9378   -1.4962    0.1008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8757   -0.0881   -0.1207 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7614   -1.1037    0.5361 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6652    0.9380   -0.8745 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4262    1.8400    2.5040 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2781    1.9745    1.7546 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7797   -0.3906    1.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0785   -0.0942   -0.3614 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2637    1.5064    0.0677 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7178    1.2605   -1.5548 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7762    0.0070   -2.3034 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2083   -1.3790   -1.7726 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8361   -1.9867   -0.2950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2794   -2.1475    0.6749 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8358   -2.0598   -0.0309 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4557   -1.3580    1.5732 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7835   -0.6376    0.6356 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1547    1.8851   -1.0387 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8940    0.4971   -1.8882 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6684    1.0527   -0.3919 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  8 10  1  0
  8  2  1  0
  7  3  1  0
  1 11  1  0
  1 12  1  0
  3 13  1  0
  4 14  1  0
  4 15  1  0
  5 16  1  0
  5 17  1  0
  6 18  1  0
  7 19  1  0
  7 20  1  0
  9 21  1  0
  9 22  1  0
  9 23  1  0
 10 24  1  0
 10 25  1  0
 10 26  1  0
M  END
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PDB for HMDB0059839 (Camphene)

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: camphene                                          
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0       0.471  -5.370   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.252  -3.846   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.263  -3.568   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.700  -3.117   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.063  -3.808   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.614  -2.641   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.129  -1.772   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.831  -0.250   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.934  -2.613   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.212  -1.584   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4    9                                             
CONECT    3    2                                                            
CONECT    4    2    5    8                                                  
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7    4                                                       
CONECT    9    7    2   10                                                  
CONECT   10    9                                                            
MASTER        0    0    0    0    0    0    0    0   10    0   22    0
END
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3D PDB for HMDB0059839 (Camphene)

COMPND    HMDB0059839
HETATM    1  C1  UNL     1      -0.302   1.499   1.781  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.003   0.504   0.931  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.287  -0.213   0.876  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.128   0.457  -0.194  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.193   0.277  -1.402  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.181  -0.745  -1.010  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.938  -1.496   0.101  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.876  -0.088  -0.121  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.761  -1.104   0.536  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.665   0.938  -0.874  1.00  0.00           C  
HETATM   11  H1  UNL     1       0.426   1.840   2.504  1.00  0.00           H  
HETATM   12  H2  UNL     1      -1.278   1.975   1.755  1.00  0.00           H  
HETATM   13  H3  UNL     1       1.780  -0.391   1.803  1.00  0.00           H  
HETATM   14  H4  UNL     1       3.079  -0.094  -0.361  1.00  0.00           H  
HETATM   15  H5  UNL     1       2.264   1.506   0.068  1.00  0.00           H  
HETATM   16  H6  UNL     1       0.718   1.261  -1.555  1.00  0.00           H  
HETATM   17  H7  UNL     1       1.776   0.007  -2.303  1.00  0.00           H  
HETATM   18  H8  UNL     1      -0.208  -1.379  -1.773  1.00  0.00           H  
HETATM   19  H9  UNL     1       1.836  -1.987  -0.295  1.00  0.00           H  
HETATM   20  H10 UNL     1       0.279  -2.148   0.675  1.00  0.00           H  
HETATM   21  H11 UNL     1      -1.836  -2.060  -0.031  1.00  0.00           H  
HETATM   22  H12 UNL     1      -1.456  -1.358   1.573  1.00  0.00           H  
HETATM   23  H13 UNL     1      -2.784  -0.638   0.636  1.00  0.00           H  
HETATM   24  H14 UNL     1      -1.155   1.885  -1.039  1.00  0.00           H  
HETATM   25  H15 UNL     1      -1.894   0.497  -1.888  1.00  0.00           H  
HETATM   26  H16 UNL     1      -2.668   1.053  -0.392  1.00  0.00           H  
CONECT    1    2    2   11   12
CONECT    2    3    8
CONECT    3    4    7   13
CONECT    4    5   14   15
CONECT    5    6   16   17
CONECT    6    7    8   18
CONECT    7   19   20
CONECT    8    9   10
CONECT    9   21   22   23
CONECT   10   24   25   26
END
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SMILES for HMDB0059839 (Camphene)

CC1(C)C2CCC(C2)C1=C
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INCHI for HMDB0059839 (Camphene)

InChI=1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3
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View in JSmolView Stereo Labels
Synonyms
ValueSource
2,2-Dimethyl-3-methylenebicyclo[2.2.1]heptaneChEBI
2,2-Dimethyl-3-methylenenorbornaneChEBI
3,3-Dimethyl-2-methylenenorbornaneChEBI
3,3-Dimethyl-2-methylenenorcamphaneChEBI
CompheneChEBI
3,3-Dimethyl-2-methylidenebicyclo[2.2.1]heptaneHMDB
Chemical FormulaC10H16
Average Molecular Weight136.238
Monoisotopic Molecular Weight136.125200515
IUPAC Name2,2-dimethyl-3-methylidenebicyclo[2.2.1]heptane
Traditional Namecamphene
CAS Registry Number79-92-5
SMILES
CC1(C)C2CCC(C2)C1=C
InChI Identifier
InChI=1S/C10H16/c1-7-8-4-5-9(6-8)10(7,2)3/h8-9H,1,4-6H2,2-3H3
InChI KeyCRPUJAZIXJMDBK-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassMonoterpenoids
Direct ParentBicyclic monoterpenoids
Alternative Parents
Substituents
  • Bicyclic monoterpenoid
  • Branched unsaturated hydrocarbon
  • Polycyclic hydrocarbon
  • Cyclic olefin
  • Unsaturated aliphatic hydrocarbon
  • Unsaturated hydrocarbon
  • Olefin
  • Hydrocarbon
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
Ontology
Physiological effect
Organoleptic effect
Disposition
Biological locationRoute of exposureSource
Process
Naturally occurring process
Role
Industrial applicationBiological role
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Baker130.63230932474
[M+H]+Not Available130.632http://allccs.zhulab.cn/database/detail?ID=AllCCS00001980
Predicted Molecular Properties
Predicted Chromatographic Properties
Spectra
Biological Properties
Cellular Locations
  • Membrane (predicted from logP)
Biospecimen Locations
  • Feces
  • Saliva
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Normal		 details
SalivaDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Not SpecifiedNormal details
Abnormal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
FecesDetected but not QuantifiedNot QuantifiedAdult (>18 years old)Both
Nonalcoholic fatty liver disease (NAFLD)		 details
Associated Disorders and Diseases
Disease References
Nonalcoholic fatty liver disease
  1. 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 ]
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDFDB009065
KNApSAcK IDC00003029
Chemspider ID6364
KEGG Compound IDC06076
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCamphene
METLIN IDNot Available
PubChem Compound6616
PDB IDNot Available
ChEBI ID3830
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
  2. 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 ]
  3. 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 ]
  4. 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 ]
  5. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]
  6. McGarvey DJ, Croteau R: Terpenoid metabolism. Plant Cell. 1995 Jul;7(7):1015-26. doi: 10.1105/tpc.7.7.1015. [PubMed:7640522 ]
  7. Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.