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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2014-10-08 15:54:21 UTC

Update Date

2022-03-07 03:17:46 UTC

HMDB ID

HMDB0061779

Secondary Accession Numbers

HMDB61779

Metabolite Identification

Common Name

Isocaryophyllene

Description

Isocaryophyllene, also known as Gamma-caryophyllene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, isocaryophyllene is considered to be an isoprenoid lipid molecule. Isocaryophyllene is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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

HMDB0061779
     RDKit          3D
Isocaryophyllene
 39 40  0  0  0  0  0  0  0  0999 V2000
    0.9486    3.3240   -0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3800    2.1990   -0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8847    2.2345    0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9373    1.5281   -0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4781    0.4264    0.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3612   -0.8529    0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9522   -1.8464    1.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659   -1.2549   -1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1904   -1.1985   -1.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -0.2888   -0.0654 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0682    0.9315   -0.6436 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2193    0.7372    0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8535   -0.7329    0.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9256   -1.4411    1.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6149   -1.4211   -0.7616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8739    3.3527   -1.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709    4.2803   -0.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813    3.2963    0.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7199    1.7843    1.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5596    1.2224   -1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7782    2.2343   -0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0001    0.7155    1.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4672   -1.8516    2.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0349   -1.6762    1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8765   -2.8837    0.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1143   -0.6550   -1.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9521   -2.3163   -1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2563   -2.2253   -0.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1692   -0.9019   -2.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1103   -0.0827    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3670    0.8669   -1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0185    1.2311    1.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1891    0.9838   -0.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9351   -1.8637    1.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249   -0.7872    2.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292   -2.3181    1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2972   -2.4700   -0.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6039   -0.8214   -1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6797   -1.4585   -0.4418 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  1
 11 31  1  6
 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


  Mrv1652304022019462D          

 17 18  0  0  0  0            999 V2000
    0.9899   -0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0990   -0.6708    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2422    0.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8297    0.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0545    1.1382    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7206    0.8560    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1331    0.1415    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2509    1.4880    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3579   -1.2011    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.3579   -2.0261    0.0000 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.4670   -2.0261    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4670   -1.2011    0.0000 C   0  0  2  0  0  0  0  0  0  0  0  0
   -1.8135   -1.0833    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2147   -1.5498    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4870   -2.8410    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1601   -2.2187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1056   -1.5498    0.0000 H   0  0  0  0  0  0  0  0  0  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  2  0  0  0  0
  6  7  1  0  0  0  0
  1  7  1  0  0  0  0
  6  8  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
  9 12  1  0  0  0  0
  1  9  1  0  0  0  0
 12  2  1  0  0  0  0
  2 13  2  0  0  0  0
 10 15  1  6  0  0  0
 10 16  1  1  0  0  0
 12 14  1  1  0  0  0
  9 17  1  6  0  0  0
M  END
> <DATABASE_ID>
HMDB0061779

> <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-FLFDDASRSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
25.995274071404452

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1R,4Z,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>
67.45239999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.01e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
isocaryophyllene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0061779
     RDKit          3D
Isocaryophyllene
 39 40  0  0  0  0  0  0  0  0999 V2000
    0.9486    3.3240   -0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3800    2.1990   -0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8847    2.2345    0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9373    1.5281   -0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4781    0.4264    0.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3612   -0.8529    0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9522   -1.8464    1.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659   -1.2549   -1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1904   -1.1985   -1.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -0.2888   -0.0654 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0682    0.9315   -0.6436 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2193    0.7372    0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8535   -0.7329    0.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9256   -1.4411    1.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6149   -1.4211   -0.7616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8739    3.3527   -1.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709    4.2803   -0.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813    3.2963    0.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7199    1.7843    1.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5596    1.2224   -1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7782    2.2343   -0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0001    0.7155    1.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4672   -1.8516    2.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0349   -1.6762    1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8765   -2.8837    0.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1143   -0.6550   -1.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9521   -2.3163   -1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2563   -2.2253   -0.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1692   -0.9019   -2.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1103   -0.0827    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3670    0.8669   -1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0185    1.2311    1.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1891    0.9838   -0.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9351   -1.8637    1.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249   -0.7872    2.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292   -2.3181    1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2972   -2.4700   -0.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6039   -0.8214   -1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6797   -1.4585   -0.4418 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  1
 11 31  1  6
 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                                 02-APR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   02-APR-20         0                                  
HETATM    1  C   UNK     0       1.848  -1.252   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.051  -1.252   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.319   0.264   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -1.549   1.598   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -0.102   2.125   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       1.345   1.598   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.115   0.264   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.335   2.778   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       0.668  -2.242   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       0.668  -3.782   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.872  -3.782   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -0.872  -2.242   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.385  -2.022   0.000  0.00  0.00           C+0
HETATM   14  H   UNK     0      -2.267  -2.893   0.000  0.00  0.00           H+0
HETATM   15  C   UNK     0       0.909  -5.303   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.166  -4.142   0.000  0.00  0.00           C+0
HETATM   17  H   UNK     0       2.064  -2.893   0.000  0.00  0.00           H+0
CONECT    1    7    9                                                       
CONECT    2    3   12   13                                                  
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8                                                  
CONECT    7    6    1                                                       
CONECT    8    6                                                            
CONECT    9   10   12    1   17                                             
CONECT   10    9   11   15   16                                             
CONECT   11   10   12                                                       
CONECT   12   11    9    2   14                                             
CONECT   13    2                                                            
CONECT   14   12                                                            
CONECT   15   10                                                            
CONECT   16   10                                                            
CONECT   17    9                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0061779
HETATM    1  C1  UNL     1       0.949   3.324  -0.735  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.380   2.199  -0.318  1.00  0.00           C  
HETATM    3  C3  UNL     1      -0.885   2.235   0.436  1.00  0.00           C  
HETATM    4  C4  UNL     1      -1.937   1.528  -0.385  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.478   0.426   0.446  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.361  -0.853   0.143  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.952  -1.846   1.068  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.666  -1.255  -1.075  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.190  -1.198  -1.044  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.439  -0.289  -0.065  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.068   0.932  -0.644  1.00  0.00           C  
HETATM   12  C12 UNL     1       2.219   0.737   0.351  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.853  -0.733   0.333  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.926  -1.441   1.645  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.615  -1.421  -0.762  1.00  0.00           C  
HETATM   16  H1  UNL     1       1.874   3.353  -1.291  1.00  0.00           H  
HETATM   17  H2  UNL     1       0.471   4.280  -0.514  1.00  0.00           H  
HETATM   18  H3  UNL     1      -1.181   3.296   0.618  1.00  0.00           H  
HETATM   19  H4  UNL     1      -0.720   1.784   1.425  1.00  0.00           H  
HETATM   20  H5  UNL     1      -1.560   1.222  -1.358  1.00  0.00           H  
HETATM   21  H6  UNL     1      -2.778   2.234  -0.565  1.00  0.00           H  
HETATM   22  H7  UNL     1      -3.000   0.715   1.358  1.00  0.00           H  
HETATM   23  H8  UNL     1      -2.467  -1.852   2.066  1.00  0.00           H  
HETATM   24  H9  UNL     1      -4.035  -1.676   1.245  1.00  0.00           H  
HETATM   25  H10 UNL     1      -2.877  -2.884   0.643  1.00  0.00           H  
HETATM   26  H11 UNL     1      -2.114  -0.655  -1.924  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.952  -2.316  -1.347  1.00  0.00           H  
HETATM   28  H13 UNL     1       0.256  -2.225  -0.897  1.00  0.00           H  
HETATM   29  H14 UNL     1       0.169  -0.902  -2.072  1.00  0.00           H  
HETATM   30  H15 UNL     1      -0.110  -0.083   0.882  1.00  0.00           H  
HETATM   31  H16 UNL     1       1.367   0.867  -1.695  1.00  0.00           H  
HETATM   32  H17 UNL     1       2.019   1.231   1.323  1.00  0.00           H  
HETATM   33  H18 UNL     1       3.189   0.984  -0.101  1.00  0.00           H  
HETATM   34  H19 UNL     1       2.935  -1.864   1.754  1.00  0.00           H  
HETATM   35  H20 UNL     1       1.725  -0.787   2.513  1.00  0.00           H  
HETATM   36  H21 UNL     1       1.229  -2.318   1.603  1.00  0.00           H  
HETATM   37  H22 UNL     1       2.297  -2.470  -0.920  1.00  0.00           H  
HETATM   38  H23 UNL     1       2.604  -0.821  -1.697  1.00  0.00           H  
HETATM   39  H24 UNL     1       3.680  -1.458  -0.442  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

HMDB0061779
     RDKit          3D
Isocaryophyllene
 39 40  0  0  0  0  0  0  0  0999 V2000
    0.9486    3.3240   -0.7352 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3800    2.1990   -0.3182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8847    2.2345    0.4360 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9373    1.5281   -0.3847 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4781    0.4264    0.4460 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3612   -0.8529    0.1427 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9522   -1.8464    1.0680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6659   -1.2549   -1.0754 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1904   -1.1985   -1.0439 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4392   -0.2888   -0.0654 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0682    0.9315   -0.6436 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2193    0.7372    0.3507 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8535   -0.7329    0.3332 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9256   -1.4411    1.6446 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6149   -1.4211   -0.7616 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8739    3.3527   -1.2907 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4709    4.2803   -0.5145 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1813    3.2963    0.6182 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7199    1.7843    1.4250 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5596    1.2224   -1.3580 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7782    2.2343   -0.5647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0001    0.7155    1.3582 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4672   -1.8516    2.0661 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0349   -1.6762    1.2450 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8765   -2.8837    0.6429 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1143   -0.6550   -1.9235 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9521   -2.3163   -1.3474 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2563   -2.2253   -0.8968 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1692   -0.9019   -2.0723 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1103   -0.0827    0.8818 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3670    0.8669   -1.6953 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0185    1.2311    1.3231 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1891    0.9838   -0.1010 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9351   -1.8637    1.7545 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7249   -0.7872    2.5125 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2292   -2.3181    1.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2972   -2.4700   -0.9197 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6039   -0.8214   -1.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6797   -1.4585   -0.4418 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  1
 11 31  1  6
 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
Gamma-Caryophyllene	HMDB
g-Caryophyllene	HMDB
Γ-caryophyllene	HMDB
Caryophyllene, (r,4Z,9S)-(+-)-isomer	HMDB
Caryophyllene	HMDB
Caryophyllene, (R-(r*,4E,9S))-isomer	HMDB
Caryophyllene, (R-(r,4Z,9S))-isomer	HMDB
Caryophyllene, (S-(r,4E,9S))-isomer	HMDB
Caryophyllene, (S-(r,4Z,9S))-isomer	HMDB

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.357

Monoisotopic Molecular Weight

204.187800773

IUPAC Name

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

Traditional Name

isocaryophyllene

CAS Registry Number

118-65-0

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-FLFDDASRSA-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

sesquiterpenoid (CHEBI:5993 )
Caryophyllane sesquiterpenoids (C09691 )
Humulenes (C09691 )
Caryophyllane sesquiterpenoids (LMPR0103120002 )

Ontology

Not Available

Non-excretory biofluid

Saliva (PMID: 24421258)

Source

Exogenous

Food

Milk and milk product

Unfermented milk

Milk (Cow) (FooDB: FOOD00618)

Herb and spice

Spice

Cloves (FooDB: FOOD00179)

Process

Not Available

Role

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	0.003 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	26 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]+	148.062	31661259
DarkChem	[M-H]-	147.799	31661259
DeepCCS	[M-2H]-	187.396	30932474
DeepCCS	[M+Na]+	162.467	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 Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Isocaryophyllene	[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C/CCC2=C	1644.0	Standard polar	33892256
Isocaryophyllene	[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C/CCC2=C	1447.0	Standard non polar	33892256
Isocaryophyllene	[H][C@]12CC(C)(C)[C@]1([H])CC\C(C)=C/CCC2=C	1442.3	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 - Isocaryophyllene GC-MS (Non-derivatized) - 70eV, Positive	splash10-0002-2900000000-666e65f6b538d4a0eeea	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Isocaryophyllene 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 - Isocaryophyllene 10V, Positive-QTOF	splash10-0a4i-0290000000-de2a6b536bb38d3c2951	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocaryophyllene 20V, Positive-QTOF	splash10-0a4i-3950000000-6dc317c917393691dfef	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocaryophyllene 40V, Positive-QTOF	splash10-0f7a-6900000000-5f5ee8e9f24e0511e186	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocaryophyllene 10V, Negative-QTOF	splash10-0udi-0090000000-d6c31402204fa765cbc0	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocaryophyllene 20V, Negative-QTOF	splash10-0udi-0290000000-48307d26c19d0c84ce74	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocaryophyllene 40V, Negative-QTOF	splash10-002r-2900000000-741197d2390e8d4bc104	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocaryophyllene 10V, Positive-QTOF	splash10-0a4i-0190000000-18da8cef0774773a4664	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocaryophyllene 20V, Positive-QTOF	splash10-0a4j-7930000000-0de14671750170215e53	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocaryophyllene 40V, Positive-QTOF	splash10-0a4m-9400000000-c0fc2f9446fefc882918	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocaryophyllene 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocaryophyllene 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Isocaryophyllene 40V, Negative-QTOF	splash10-0udi-0980000000-9f708eefb54c5860f003	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

Biospecimen Locations

Saliva

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Not Specified	Normal	24421258	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

C00012474

Chemspider ID

Not Available

KEGG Compound ID

C09691

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5281522

PDB ID

Not Available

ChEBI ID

5993

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Jelen HH, Mirocha CJ, Wasowicz E, Kaminski E: Production of volatile sesquiterpenes by Fusarium sambucinum strains with different abilities to synthesize trichothecenes. Appl Environ Microbiol. 1995 Nov;61(11):3815-20. [PubMed:8526491 ]
Demirci B, Baser KH, Ozek T, Demirci F: Betulenols from Betula species. Planta Med. 2000 Jun;66(5):490-3. [PubMed:10909279 ]
Hernandez T, Canales M, Avila JG, Garcia AM, Martinez A, Caballero J, de Vivar AR, Lira R: Composition and antibacterial activity of essential oil of Lantana achyranthifolia Desf. (Verbenaceae). J Ethnopharmacol. 2005 Jan 15;96(3):551-4. [PubMed:15619577 ]
Ricci D, Fraternale D, Giamperi L, Bucchini A, Epifano F, Burini G, Curini M: Chemical composition, antimicrobial and antioxidant activity of the essential oil of Teucrium marum (Lamiaceae). J Ethnopharmacol. 2005 Apr 8;98(1-2):195-200. [PubMed:15763383 ]
Sabulal B, Dan M, J AJ, Kurup R, Pradeep NS, Valsamma RK, George V: Caryophyllene-rich rhizome oil of Zingiber nimmonii from South India: Chemical characterization and antimicrobial activity. Phytochemistry. 2006 Nov;67(22):2469-73. Epub 2006 Sep 14. [PubMed:16973189 ]
Legault J, Pichette A: Potentiating effect of beta-caryophyllene on anticancer activity of alpha-humulene, isocaryophyllene and paclitaxel. J Pharm Pharmacol. 2007 Dec;59(12):1643-7. [PubMed:18053325 ]
Ashitani T, Borg-Karlson AK, Fujita K, Nagahama S: Reaction mechanism of direct episulfidation of caryophyllene and humulene. Nat Prod Res. 2008 Apr 15;22(6):495-8. doi: 10.1080/14786410701591903. [PubMed:18415856 ]
Sousa EO, Silva NF, Rodrigues FF, Campos AR, Lima SG, Costa JG: Chemical composition and resistance-modifying effect of the essential oil of Lantana camara Linn. Pharmacogn Mag. 2010 Apr;6(22):79-82. doi: 10.4103/0973-1296.62890. Epub 2010 May 5. [PubMed:20668570 ]
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.
Qinghe Zhang, Armenek Margaryan, Rodney G. Schneidmiller, 'METHODS FOR REPELLING INSECTS USING SESQUITERPENE HYDROCARBONS AND THEIR DERIVATIVES.' U.S. Patent US20100166896, issued July 01, 2010. [Link]
Qinghe Zhang, Armenek Margaryan, Rodney G. Schneidmiller, 'Methods for repelling insects using sesquiterpene hydrocarbons and their derivatives.' U.S. Patent US08057829, issued November 15, 2011. [Link]

Showing metabocard for Isocaryophyllene (HMDB0061779)

MOL for HMDB0061779 (Isocaryophyllene)

3D MOL for HMDB0061779 (Isocaryophyllene)

3D SDF for HMDB0061779 (Isocaryophyllene)

3D-SDF for HMDB0061779 (Isocaryophyllene)

PDB for HMDB0061779 (Isocaryophyllene)

3D PDB for HMDB0061779 (Isocaryophyllene)

SMILES for HMDB0061779 (Isocaryophyllene)

INCHI for HMDB0061779 (Isocaryophyllene)

Structure for HMDB0061779 (Isocaryophyllene)

3D Structure for HMDB0061779 (Isocaryophyllene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra