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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 21:58:08 UTC

Update Date

2022-03-07 02:55:03 UTC

HMDB ID

HMDB0036792

Secondary Accession Numbers

HMDB0061842
HMDB36792
HMDB61842

Metabolite Identification

Common Name

beta-Caryophyllene

Description

beta-Caryophyllene, also known as caryophyllene or (−)-β-caryophyllene, is a natural bicyclic sesquiterpene that is a constituent of many essential oils including that of Syzygium aromaticum (cloves), Cannabis sativa, rosemary, and hops. It is usually found as a mixture with isocaryophyllene (the cis double bond isomer) and α-humulene (obsolete name: α-caryophyllene), a ring-opened isomer. beta-Caryophyllene is notable for having both a cyclobutane ring and a trans-double bond in a nine-membered ring, both rarities in nature (Wikipedia ). beta-Caryophyllene is a sweet and dry tasting compound that can be found in a number of food items such as allspice, fig, pot marjoram, and roman camomile, which makes beta-caryophyllene a potential biomarker for the consumption of these food products. beta-Caryophyllene can be found in feces and saliva.

Structure

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

HMDB0036792
     RDKit          3D
beta-Caryophyllene
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.7588    3.1873   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1259    2.0532   -0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2669    1.8953   -0.5447 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0691    1.3597    0.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373    0.2061    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6178   -0.9482   -0.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7805   -1.9196   -0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -1.4492   -0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1750   -1.2686    0.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8433   -0.3197   -0.2709 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8269    0.9353    0.5667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3417    0.9693    0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2737   -0.5087    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5460   -1.4417    1.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2183   -0.7576   -1.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2192    4.0160   -0.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7839    3.3694    0.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3717    1.3022   -1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6384    2.9189   -0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6959    2.2502    0.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    1.1981    1.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0123    0.4071    0.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2008   -1.7954   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5809   -1.7113    0.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4398   -2.9536   -0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3703   -2.5376   -0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9661   -0.9999   -1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2788   -2.2787    0.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5999   -0.9687    1.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7556   -0.1847   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5325    0.7511    1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482    1.0783    1.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7594    1.6162   -0.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6023   -1.2454    1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9132   -1.2998    2.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5573   -2.4720    0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4496   -1.8384   -1.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934   -0.4579   -1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1365   -0.1572   -0.9654 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  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 11  2  1  0
 13 10  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  6
 11 31  1  1
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END


  Mrv1652309272007282D          

 17 18  0  0  1  0            999 V2000
   22.7121   -2.5520    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9979   -2.1389    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2831   -2.5509    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4269   -2.1401    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1409   -2.5532    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.1404   -3.3782    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.4256   -3.7901    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   21.2825   -3.3759    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9966   -3.7890    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   22.2452   -4.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.1795   -4.6121    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.9986   -1.3140    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.8545   -3.7912    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.0265   -5.4071    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4500   -4.8208    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.2647   -4.2170    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
   24.1436   -4.2045    0.0000 H   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
  1  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
  3  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9  7  1  0  0  0  0
  9 10  1  0  0  0  0
  7 11  1  0  0  0  0
 10 11  1  0  0  0  0
  2 12  1  0  0  0  0
  6 13  2  0  0  0  0
 10 14  1  0  0  0  0
 10 15  1  0  0  0  0
  9 16  1  1  0  0  0
  7 17  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0036792

> <DATABASE_NAME>
hmdb

> <SMILES>
[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C\CCC2=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1

> <INCHI_KEY>
NPNUFJAVOOONJE-GFUGXAQUSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.646995134834675

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

> <ALOGPS_LOGP>
5.35

> <JCHEM_LOGP>
4.519309391666669

> <ALOGPS_LOGS>
-4.83

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
67.4524

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
caryophyllene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036792
     RDKit          3D
beta-Caryophyllene
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.7588    3.1873   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1259    2.0532   -0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2669    1.8953   -0.5447 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0691    1.3597    0.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373    0.2061    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6178   -0.9482   -0.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7805   -1.9196   -0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -1.4492   -0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1750   -1.2686    0.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8433   -0.3197   -0.2709 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8269    0.9353    0.5667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3417    0.9693    0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2737   -0.5087    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5460   -1.4417    1.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2183   -0.7576   -1.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2192    4.0160   -0.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7839    3.3694    0.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3717    1.3022   -1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6384    2.9189   -0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6959    2.2502    0.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    1.1981    1.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0123    0.4071    0.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2008   -1.7954   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5809   -1.7113    0.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4398   -2.9536   -0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3703   -2.5376   -0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9661   -0.9999   -1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2788   -2.2787    0.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5999   -0.9687    1.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7556   -0.1847   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5325    0.7511    1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482    1.0783    1.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7594    1.6162   -0.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6023   -1.2454    1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9132   -1.2998    2.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5573   -2.4720    0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4496   -1.8384   -1.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934   -0.4579   -1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1365   -0.1572   -0.9654 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  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 11  2  1  0
 13 10  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  6
 11 31  1  1
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
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      42.396  -4.764   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      41.063  -3.993   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      39.728  -4.762   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      43.730  -3.995   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      45.063  -4.766   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      45.062  -6.306   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      43.728  -7.075   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      39.727  -6.302   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      41.060  -7.073   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      41.524  -8.609   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      43.268  -8.609   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      41.064  -2.453   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      46.395  -7.077   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      41.116 -10.093   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      40.040  -8.999   0.000  0.00  0.00           C+0
HETATM   16  H   UNK     0      39.694  -7.872   0.000  0.00  0.00           H+0
HETATM   17  H   UNK     0      45.068  -7.848   0.000  0.00  0.00           H+0
CONECT    1    2    4                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    8                                                       
CONECT    4    1    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7   13                                                  
CONECT    7    6    9   11   17                                             
CONECT    8    3    9                                                       
CONECT    9    8    7   10   16                                             
CONECT   10    9   11   14   15                                             
CONECT   11    7   10                                                       
CONECT   12    2                                                            
CONECT   13    6                                                            
CONECT   14   10                                                            
CONECT   15   10                                                            
CONECT   16    9                                                            
CONECT   17    7                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0036792
HETATM    1  C1  UNL     1      -0.759   3.187  -0.255  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.126   2.053  -0.087  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.267   1.895  -0.545  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.069   1.360   0.610  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.937   0.206   0.285  1.00  0.00           C  
HETATM    6  C6  UNL     1       2.618  -0.948  -0.244  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.780  -1.920  -0.444  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.304  -1.449  -0.679  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.175  -1.269   0.290  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.843  -0.320  -0.271  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.827   0.935   0.567  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.342   0.969   0.526  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.274  -0.509   0.140  1.00  0.00           C  
HETATM   14  C14 UNL     1      -2.546  -1.442   1.262  1.00  0.00           C  
HETATM   15  C15 UNL     1      -3.218  -0.758  -1.018  1.00  0.00           C  
HETATM   16  H1  UNL     1      -0.219   4.016  -0.746  1.00  0.00           H  
HETATM   17  H2  UNL     1      -1.784   3.369   0.060  1.00  0.00           H  
HETATM   18  H3  UNL     1       1.372   1.302  -1.481  1.00  0.00           H  
HETATM   19  H4  UNL     1       1.638   2.919  -0.874  1.00  0.00           H  
HETATM   20  H5  UNL     1       2.696   2.250   0.951  1.00  0.00           H  
HETATM   21  H6  UNL     1       1.438   1.198   1.533  1.00  0.00           H  
HETATM   22  H7  UNL     1       4.012   0.407   0.552  1.00  0.00           H  
HETATM   23  H8  UNL     1       4.201  -1.795  -1.445  1.00  0.00           H  
HETATM   24  H9  UNL     1       4.581  -1.711   0.295  1.00  0.00           H  
HETATM   25  H10 UNL     1       3.440  -2.954  -0.247  1.00  0.00           H  
HETATM   26  H11 UNL     1       1.370  -2.538  -0.943  1.00  0.00           H  
HETATM   27  H12 UNL     1       0.966  -1.000  -1.663  1.00  0.00           H  
HETATM   28  H13 UNL     1      -0.279  -2.279   0.502  1.00  0.00           H  
HETATM   29  H14 UNL     1       0.600  -0.969   1.268  1.00  0.00           H  
HETATM   30  H15 UNL     1      -0.756  -0.185  -1.346  1.00  0.00           H  
HETATM   31  H16 UNL     1      -0.532   0.751   1.633  1.00  0.00           H  
HETATM   32  H17 UNL     1      -2.848   1.078   1.500  1.00  0.00           H  
HETATM   33  H18 UNL     1      -2.759   1.616  -0.253  1.00  0.00           H  
HETATM   34  H19 UNL     1      -3.602  -1.245   1.611  1.00  0.00           H  
HETATM   35  H20 UNL     1      -1.913  -1.300   2.147  1.00  0.00           H  
HETATM   36  H21 UNL     1      -2.557  -2.472   0.874  1.00  0.00           H  
HETATM   37  H22 UNL     1      -3.450  -1.838  -1.136  1.00  0.00           H  
HETATM   38  H23 UNL     1      -2.693  -0.458  -1.964  1.00  0.00           H  
HETATM   39  H24 UNL     1      -4.136  -0.157  -0.965  1.00  0.00           H  
CONECT    1    2    2   16   17
CONECT    2    3   11
CONECT    3    4   18   19
CONECT    4    5   20   21
CONECT    5    6    6   22
CONECT    6    7    8
CONECT    7   23   24   25
CONECT    8    9   26   27
CONECT    9   10   28   29
CONECT   10   11   13   30
CONECT   11   12   31
CONECT   12   13   32   33
CONECT   13   14   15
CONECT   14   34   35   36
CONECT   15   37   38   39
END

HMDB0036792
     RDKit          3D
beta-Caryophyllene
 39 40  0  0  0  0  0  0  0  0999 V2000
   -0.7588    3.1873   -0.2549 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1259    2.0532   -0.0875 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2669    1.8953   -0.5447 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0691    1.3597    0.6103 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9373    0.2061    0.2848 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6178   -0.9482   -0.2437 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7805   -1.9196   -0.4439 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3039   -1.4492   -0.6786 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1750   -1.2686    0.2895 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8433   -0.3197   -0.2709 C   0  0  2  0  0  0  0  0  0  0  0  0
   -0.8269    0.9353    0.5667 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.3417    0.9693    0.5261 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2737   -0.5087    0.1403 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5460   -1.4417    1.2616 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2183   -0.7576   -1.0175 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2192    4.0160   -0.7464 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7839    3.3694    0.0596 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3717    1.3022   -1.4809 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6384    2.9189   -0.8745 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6959    2.2502    0.9508 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4380    1.1981    1.5333 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0123    0.4071    0.5522 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2008   -1.7954   -1.4446 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5809   -1.7113    0.2948 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4398   -2.9536   -0.2471 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3703   -2.5376   -0.9430 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9661   -0.9999   -1.6625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2788   -2.2787    0.5015 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5999   -0.9687    1.2681 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7556   -0.1847   -1.3457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5325    0.7511    1.6334 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8482    1.0783    1.4995 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7594    1.6162   -0.2532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6023   -1.2454    1.6113 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9132   -1.2998    2.1469 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5573   -2.4720    0.8742 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4496   -1.8384   -1.1359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6934   -0.4579   -1.9640 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1365   -0.1572   -0.9654 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  2  0
  6  7  1  0
  6  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 13 15  1  0
 11  2  1  0
 13 10  1  0
  1 16  1  0
  1 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  7 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  6
 11 31  1  1
 12 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(-)-(e)-beta-Caryophyllene	ChEBI
(e)-beta-Caryophyllene	ChEBI
Caryophyllene	ChEBI
trans-(1R,9S)-4,11,11-Trimethyl-8-methylenebicyclo[7.2.0]undec-4-ene	ChEBI
trans-Caryophyllene	ChEBI
(-)-beta-Caryophyllene	Kegg
(-)-(e)-b-Caryophyllene	Generator
(-)-(e)-Β-caryophyllene	Generator
(e)-b-Caryophyllene	Generator
(e)-Β-caryophyllene	Generator
(-)-b-Caryophyllene	Generator
(-)-Β-caryophyllene	Generator
b-Caryophyllene	Generator
Β-caryophyllene	Generator
Caryophyllene, (S-(r,4Z,9S))-isomer	HMDB
Caryophyllene, (R-(r*,4E,9S))-isomer	HMDB
Caryophyllene, (r,4Z,9S)-(+-)-isomer	HMDB
Caryophyllene, (R-(r,4Z,9S))-isomer	HMDB
Caryophyllene, (S-(r,4E,9S))-isomer	HMDB
(-)-(e)-Caryophyllene	HMDB
(-)-e-Caryophyllene	HMDB
(-)-Caryophyllene	HMDB
(-)-trans-Caryophyllene	HMDB
(e)-Caryophyllene	HMDB
Caryophyllene b	HMDB
NSC 11906	HMDB
trans-Β-caryophyllene	HMDB
trans-beta-Caryophyllene	HMDB
Β-caryophyllen	HMDB
beta-Caryophyllen	HMDB
beta-Caryophyllene	HMDB, ChEBI
l-Caryophyllene	PhytoBank
beta-Caryophellene	PhytoBank
β-Caryophellene	PhytoBank

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.357

Monoisotopic Molecular Weight

204.187800773

IUPAC Name

(1R,4E,9S)-4,11,11-trimethyl-8-methylidenebicyclo[7.2.0]undec-4-ene

Traditional Name

caryophyllene

CAS Registry Number

87-44-5

SMILES

[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C\CCC2=C

InChI Identifier

InChI=1S/C15H24/c1-11-6-5-7-12(2)13-10-15(3,4)14(13)9-8-11/h6,13-14H,2,5,7-10H2,1,3-4H3/b11-6+/t13-,14-/m1/s1

InChI Key

NPNUFJAVOOONJE-GFUGXAQUSA-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

Caryophyllane 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

beta-caryophyllene (CHEBI:10357 )
Caryophyllane sesquiterpenoids (C09629 )
Humulenes (C09629 )
Caryophyllane sesquiterpenoids (LMPR0103120001 )

Ontology

Sweet

Disposition

Source

Exogenous

Exogenous (HMDB: HMDB0061842)

Food

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Fruit

Berry

Other fruit

Fig (FooDB: FOOD00081)

Tropical fruit

Citrus

Lemon (FooDB: FOOD00054)
Lime (FooDB: FOOD00053)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)
Pummelo (FooDB: FOOD00055)

Vegetable

Root vegetable

Fruit vegetable

Pepper (FooDB: FOOD00040)
Green bell pepper (FooDB: FOOD00877)
Yellow bell pepper (FooDB: FOOD00878)
Red bell pepper (FooDB: FOOD00880)
Garden tomato (var.) (FooDB: FOOD00173)
Pepper (C. frutescens) (FooDB: FOOD00428)
Orange bell pepper (FooDB: FOOD00879)

Shoot vegetable

American pokeweed (FooDB: FOOD00437)

Leaf vegetable

Rocket salad (ssp.) (FooDB: FOOD00077)

Stalk vegetable

Celery stalks (FooDB: FOOD00215)

Safflower (FooDB: FOOD00042)

Herbs and Spices (FooDB: FOOD00866)

Cereal and cereal product

Cereal

Corn (FooDB: FOOD00205)
Oat (FooDB: FOOD00022)

Nut

Pine nut (FooDB: FOOD00138)

Not Available

EC 1.1.1.21 (aldehyde reductase) inhibitor (HMDB: HMDB0061842)

Industrial application

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	256.00 to 259.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.05 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.300	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.003 g/L	ALOGPS
logP	5.35	ALOGPS
logP	4.52	ChemAxon
logS	-4.8	ALOGPS
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	0	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	0 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	67.45 m³·mol⁻¹	ChemAxon
Polarizability	25.65 Å³	ChemAxon
Number of Rings	2	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]+	148.09	31661259
DarkChem	[M-H]-	147.166	31661259
DeepCCS	[M-2H]-	186.22	30932474
DeepCCS	[M+Na]+	161.292	30932474
AllCCS	[M+H]+	147.3	32859911
AllCCS	[M+H-H2O]+	143.2	32859911
AllCCS	[M+NH4]+	151.0	32859911
AllCCS	[M+Na]+	152.1	32859911
AllCCS	[M-H]-	156.0	32859911
AllCCS	[M+Na-2H]-	156.4	32859911
AllCCS	[M+HCOO]-	157.0	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.	6.75 minutes	32390414
Predicted by Siyang on May 30, 2022	21.4077 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.58 minutes	32390414

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-Caryophyllene	[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C\CCC2=C	1644.0	Standard polar	33892256
beta-Caryophyllene	[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C\CCC2=C	1447.0	Standard non polar	33892256
beta-Caryophyllene	[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C\CCC2=C	1442.3	Semi standard non polar	33892256

Spectra

Biological Properties

Cellular Locations

Extracellular
Membrane

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
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details
Saliva	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Normal	24657864	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Campylobacter jejuni infection	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative Colitis	17314143	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Nonalcoholic fatty liver disease (NAFLD)	23454028	details
Saliva	Detected but not Quantified	Not Quantified	Children (1-13 years old)	Both	Celiac disease	24657864	details

Associated Disorders and Diseases

Disease References

Ulcerative colitis
Garner CE, Smith S, de Lacy Costello B, White P, Spencer R, Probert CS, Ratcliffe NM: Volatile organic compounds from feces and their potential for diagnosis of gastrointestinal disease. FASEB J. 2007 Jun;21(8):1675-88. Epub 2007 Feb 21. [PubMed:17314143 ]
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 ]
Celiac disease
Francavilla R, Ercolini D, Piccolo M, Vannini L, Siragusa S, De Filippis F, De Pasquale I, Di Cagno R, Di Toma M, Gozzi G, Serrazanetti DI, De Angelis M, Gobbetti M: Salivary microbiota and metabolome associated with celiac disease. Appl Environ Microbiol. 2014 Jun;80(11):3416-25. doi: 10.1128/AEM.00362-14. Epub 2014 Mar 21. [PubMed:24657864 ]

Associated OMIM IDs

212750 (Celiac disease)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

BiGG ID

Not Available

Wikipedia Link

Caryophyllene

METLIN ID

Not Available

PubChem Compound

5281515

PDB ID

Not Available

ChEBI ID

10357

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1060851

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Nascimento JC, Barbosa LC, Paula VF, David JM, Fontana R, Silva LA, Franca RS: Chemical composition and antimicrobial activity of essential oils of Ocimum canum Sims. and Ocimum selloi Benth. An Acad Bras Cienc. 2011 Sep;83(3):787-99. [PubMed:21969960 ]
Karim H, Kamel M, Mouna BT, Thouraya C, Brahim M: Essential oil composition of Hypericum triquetrifolium Turra. aerial parts. Ital J Biochem. 2007 Mar;56(1):40-6. [PubMed:17511353 ]
Luo J, Guo X, Feng Y: [Constituents analysis on volatile oil of Pogostemon cablin from different collection time cultivated in Hainan]. Zhong Yao Cai. 2002 Jan;25(1):21-3. [PubMed:12583236 ]
Luo J, Feng Y, Guo X, Li X: [GC-MS analysis of volatile oil of herba Pogostemonis collected from Gaoyao county]. Zhong Yao Cai. 1999 Jan;22(1):25-8. [PubMed:12575058 ]
Bhatia SP, Letizia CS, Api AM: Fragrance material review on beta-caryophyllene alcohol. Food Chem Toxicol. 2008 Nov;46 Suppl 11:S95-6. doi: 10.1016/j.fct.2008.06.030. Epub 2008 Jul 1. [PubMed:18640216 ]
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.
Wikipedia [Link]
Wikipedia [Link]
Wikipedia [Link]
MetaCyc: beta-caryophyllene biosynthesis [Link]
UniProt I6RAQ6 : (-)-beta-caryophyllene synthase [Link]
UniProt J7LJN5 : Beta-caryophyllene synthase [Link]
UniProt Q8SA63 : Beta-caryophyllene synthase [Link]

Showing metabocard for beta-Caryophyllene (HMDB0036792)

MOL for HMDB0036792 (beta-Caryophyllene)

3D MOL for HMDB0036792 (beta-Caryophyllene)

3D SDF for HMDB0036792 (beta-Caryophyllene)

3D-SDF for HMDB0036792 (beta-Caryophyllene)

PDB for HMDB0036792 (beta-Caryophyllene)

3D PDB for HMDB0036792 (beta-Caryophyllene)

SMILES for HMDB0036792 (beta-Caryophyllene)

INCHI for HMDB0036792 (beta-Caryophyllene)

Structure for HMDB0036792 (beta-Caryophyllene)

3D Structure for HMDB0036792 (beta-Caryophyllene)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized