MiMeDB: Showing metabocard for (-)-(E)-beta-caryophyllene (MMDBc0054012)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2022-06-05 22:32:52 UTC

Update Date

2024-10-07 00:33:09 UTC

Metabolite ID

MMDBc0054012

Metabolite Identification

Common Name

(-)-(E)-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>
MMDBc0054012

> <DATABASE_NAME>
MIME

> <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

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

Molecular Formula

C₁₅H₂₄

Average Mass

204.357

Monoisotopic Mass

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

Not Available

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 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted 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

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum - GC-EI-Q (Non-derivatized)	splash10-0006-9600000000-f461c075128fda03909d	2020-07-08	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2900000000-666e65f6b538d4a0eeea	2017-07-27	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0290000000-de2a6b536bb38d3c2951	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-3950000000-6dc317c917393691dfef	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0f7a-6900000000-5f5ee8e9f24e0511e186	2016-06-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-d6c31402204fa765cbc0	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0290000000-48307d26c19d0c84ce74	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-002r-2900000000-741197d2390e8d4bc104	2016-08-03	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0980000000-9f708eefb54c5860f003	2021-09-21	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0190000000-18da8cef0774773a4664	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4j-7930000000-0de14671750170215e53	2021-09-25	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a4m-9400000000-c0fc2f9446fefc882918	2021-09-25	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9600000000-0eeaa207a8899311023d	2015-03-01	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)		2022-08-17	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces
Saliva

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Actinobacteria	1
Eukaryota/Fungi	Ascomycota	1	Human feces

Exposure Sources

Source Type	Activity	Data Source	Reference
Cosmetics	Not Available	U.S. Environmental Protection Agency	CompTox
Domestics	Not Available	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Age	Sex	Health Condition	Data Source	Reference
Human Saliva	Detected but not Quantified	Adult (>18 years old)	Not Specified	Normal	HMDB	24421258
Human Saliva	Detected but not Quantified	Children (1-13 years old)	Both	Normal	HMDB	24657864
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	17314143
Human Feces	Detected but not Quantified	Adult (>18 years old)	Both	Normal	HMDB	23454028

External Links

HMDB ID

HMDB0036792

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

References

Synthesis Reference

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. doi: 10.1038/35036052. [PubMed:11413487 ]
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 ]
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 ]
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. doi: 10.1194/jlr.R600022-JLR200. 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. doi: 10.1194/jlr.R700005-JLR200. Epub 2007 Mar 20. [PubMed:17374880 ]
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 ]
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 ]
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 ]
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. doi: 10.1590/s0001-37652011005000019. [PubMed:21969960 ]
Yannai, Shmuel (2004). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. 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 (-)-(E)-beta-caryophyllene (MMDBc0054012)

MOL for #<Metabolite:0x00007fdb5220a050>

3D MOL for #<Metabolite:0x00007fdb5220a050>

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3D-SDF for #<Metabolite:0x00007fdb5220a050>

PDB for #<Metabolite:0x00007fdb5220a050>

3D PDB for #<Metabolite:0x00007fdb5220a050>

SMILES for #<Metabolite:0x00007fdb5220a050>

INCHI for #<Metabolite:0x00007fdb5220a050>

Structure for #<Metabolite:0x00007fdb5220a050>

3D Structure for #<Metabolite:0x00007fdb5220a050>