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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 21:36:30 UTC

Update Date

2022-03-07 02:54:56 UTC

HMDB ID

HMDB0036467

Secondary Accession Numbers

HMDB36467

Metabolite Identification

Common Name

alpha-Humulene

Description

alpha-Humulene, also known as alpha-caryophyllene, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Thus, alpha-humulene is considered to be an isoprenoid lipid molecule. alpha-Humulene is found in allspice. alpha-Humulene is a constituent of many essential oils including hops (Humulus lupulus) and cloves (Syzygium aromaticum).

Structure

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

HMDB0036467
     RDKit          3D
alpha-Humulene
 39 39  0  0  0  0  0  0  0  0999 V2000
    3.4463   -2.4271   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3202   -1.4243   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5989   -0.2120   -0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556    0.9392   -0.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1648    1.4845    0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0962    2.2391    0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0206    3.5522    1.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2390    1.9999   -0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7752    0.9496   -0.8473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8839   -0.4325   -0.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7795   -0.5709    1.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3544   -0.9027   -0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794   -1.3531   -1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0382   -1.9603   -0.9282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9603   -1.9693    0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1992   -2.2383   -0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0909   -3.4539   -0.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9675   -2.3712    0.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6475    0.0488   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8663    0.7145   -1.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.7917   -1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1630    0.7029    1.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0136    2.1567    1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549    4.2362    0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0064    3.9134    1.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5013    3.3228    2.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9965    2.8347    0.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3253    0.8629   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8544    1.2382   -1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708    0.0579    1.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7656   -1.6507    1.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7916   -0.2346    1.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5237   -0.7016   -1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0357   -0.4076    0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3085   -1.9904   -0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5720   -1.5212   -2.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4051   -2.6145   -1.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0635   -3.0675    0.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667   -1.5415    1.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15  2  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
M  END

  Mrv1652309272007342D          

 15 15  0  0  0  0            999 V2000
   -0.4158    1.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6704    0.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3974    0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4288   -0.7611    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4314   -0.7555    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7305   -1.1916    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0011   -0.8062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6653    0.4494    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7298   -1.1957    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7298   -2.0172    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3983    0.0661    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1098    0.4769    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2329    1.3524    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4429    2.0636    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4148    1.2367    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
 11  2  2  0  0  0  0
  8  3  2  0  0  0  0
  3  4  1  0  0  0  0
  4  9  1  0  0  0  0
 11  5  1  0  0  0  0
  6  5  1  0  0  0  0
  6  7  1  0  0  0  0
  9  7  2  0  0  0  0
  9 10  1  0  0  0  0
 11 12  1  0  0  0  0
 13 15  1  0  0  0  0
 15 14  1  0  0  0  0
 15  8  1  0  0  0  0
  1 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036467

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C1=C/CC(C)(C)\C=C\C\C(C)=C\CC1

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

> <INCHI_KEY>
FAMPSKZZVDUYOS-HRGUGZIWSA-N

> <FORMULA>
C15H24

> <MOLECULAR_WEIGHT>
204.357

> <EXACT_MASS>
204.187800773

> <JCHEM_ACCEPTOR_COUNT>
0

> <JCHEM_ATOM_COUNT>
39

> <JCHEM_AVERAGE_POLARIZABILITY>
21.080161832984516

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(1E,4E,8E)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene

> <ALOGPS_LOGP>
6.07

> <JCHEM_LOGP>
4.8782791046666665

> <ALOGPS_LOGS>
-4.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_POLAR_SURFACE_AREA>
0.0

> <JCHEM_REFRACTIVITY>
71.54849999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.08e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
humulene

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036467
     RDKit          3D
alpha-Humulene
 39 39  0  0  0  0  0  0  0  0999 V2000
    3.4463   -2.4271   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3202   -1.4243   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5989   -0.2120   -0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556    0.9392   -0.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1648    1.4845    0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0962    2.2391    0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0206    3.5522    1.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2390    1.9999   -0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7752    0.9496   -0.8473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8839   -0.4325   -0.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7795   -0.5709    1.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3544   -0.9027   -0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794   -1.3531   -1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0382   -1.9603   -0.9282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9603   -1.9693    0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1992   -2.2383   -0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0909   -3.4539   -0.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9675   -2.3712    0.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6475    0.0488   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8663    0.7145   -1.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.7917   -1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1630    0.7029    1.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0136    2.1567    1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549    4.2362    0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0064    3.9134    1.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5013    3.3228    2.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9965    2.8347    0.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3253    0.8629   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8544    1.2382   -1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708    0.0579    1.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7656   -1.6507    1.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7916   -0.2346    1.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5237   -0.7016   -1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0357   -0.4076    0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3085   -1.9904   -0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5720   -1.5212   -2.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4051   -2.6145   -1.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0635   -3.0675    0.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667   -1.5415    1.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15  2  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 14 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      -0.776   2.309   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.251   0.847   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       2.608   0.115   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667  -1.421   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -2.672  -1.410   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.364  -2.224   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.002  -1.505   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       1.242   0.839   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.362  -2.232   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.362  -3.765   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.610   0.123   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -3.938   0.890   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.301   2.525   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.827   3.852   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.774   2.309   0.000  0.00  0.00           C+0
CONECT    1    2   15                                                       
CONECT    2    1   11                                                       
CONECT    3    8    4                                                       
CONECT    4    3    9                                                       
CONECT    5   11    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    9                                                       
CONECT    8    3   15                                                       
CONECT    9    4    7   10                                                  
CONECT   10    9                                                            
CONECT   11    2    5   12                                                  
CONECT   12   11                                                            
CONECT   13   15                                                            
CONECT   14   15                                                            
CONECT   15   13   14    8    1                                             
MASTER        0    0    0    0    0    0    0    0   15    0   30    0
END

COMPND    HMDB0036467
HETATM    1  C1  UNL     1       3.446  -2.427  -0.039  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.320  -1.424  -0.138  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.599  -0.212  -0.516  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.656   0.939  -0.685  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.165   1.485   0.601  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.096   2.239   0.569  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.021   3.552   1.410  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.239   2.000  -0.012  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.775   0.950  -0.847  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.884  -0.433  -0.307  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.780  -0.571   1.169  1.00  0.00           C  
HETATM   12  C12 UNL     1      -3.354  -0.903  -0.600  1.00  0.00           C  
HETATM   13  C13 UNL     1      -1.079  -1.353  -1.130  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.038  -1.960  -0.928  1.00  0.00           C  
HETATM   15  C15 UNL     1       0.960  -1.969   0.223  1.00  0.00           C  
HETATM   16  H1  UNL     1       4.199  -2.238  -0.847  1.00  0.00           H  
HETATM   17  H2  UNL     1       3.091  -3.454  -0.188  1.00  0.00           H  
HETATM   18  H3  UNL     1       3.968  -2.371   0.915  1.00  0.00           H  
HETATM   19  H4  UNL     1       3.647   0.049  -0.750  1.00  0.00           H  
HETATM   20  H5  UNL     1       0.866   0.714  -1.415  1.00  0.00           H  
HETATM   21  H6  UNL     1       2.214   1.792  -1.190  1.00  0.00           H  
HETATM   22  H7  UNL     1       1.163   0.703   1.397  1.00  0.00           H  
HETATM   23  H8  UNL     1       2.014   2.157   1.000  1.00  0.00           H  
HETATM   24  H9  UNL     1       0.555   4.236   0.743  1.00  0.00           H  
HETATM   25  H10 UNL     1      -1.006   3.913   1.620  1.00  0.00           H  
HETATM   26  H11 UNL     1       0.501   3.323   2.360  1.00  0.00           H  
HETATM   27  H12 UNL     1      -1.997   2.835   0.200  1.00  0.00           H  
HETATM   28  H13 UNL     1      -1.325   0.863  -1.886  1.00  0.00           H  
HETATM   29  H14 UNL     1      -2.854   1.238  -1.159  1.00  0.00           H  
HETATM   30  H15 UNL     1      -1.071   0.058   1.690  1.00  0.00           H  
HETATM   31  H16 UNL     1      -1.766  -1.651   1.419  1.00  0.00           H  
HETATM   32  H17 UNL     1      -2.792  -0.235   1.587  1.00  0.00           H  
HETATM   33  H18 UNL     1      -3.524  -0.702  -1.664  1.00  0.00           H  
HETATM   34  H19 UNL     1      -4.036  -0.408   0.091  1.00  0.00           H  
HETATM   35  H20 UNL     1      -3.308  -1.990  -0.460  1.00  0.00           H  
HETATM   36  H21 UNL     1      -1.572  -1.521  -2.136  1.00  0.00           H  
HETATM   37  H22 UNL     1       0.405  -2.614  -1.770  1.00  0.00           H  
HETATM   38  H23 UNL     1       1.063  -3.068   0.519  1.00  0.00           H  
HETATM   39  H24 UNL     1       0.567  -1.541   1.157  1.00  0.00           H  
CONECT    1    2   16   17   18
CONECT    2    3    3   15
CONECT    3    4   19
CONECT    4    5   20   21
CONECT    5    6   22   23
CONECT    6    7    8    8
CONECT    7   24   25   26
CONECT    8    9   27
CONECT    9   10   28   29
CONECT   10   11   12   13
CONECT   11   30   31   32
CONECT   12   33   34   35
CONECT   13   14   14   36
CONECT   14   15   37
CONECT   15   38   39
END

HMDB0036467
     RDKit          3D
alpha-Humulene
 39 39  0  0  0  0  0  0  0  0999 V2000
    3.4463   -2.4271   -0.0390 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3202   -1.4243   -0.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5989   -0.2120   -0.5158 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6556    0.9392   -0.6845 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1648    1.4845    0.6005 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0962    2.2391    0.5692 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0206    3.5522    1.4102 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2390    1.9999   -0.0118 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7752    0.9496   -0.8473 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8839   -0.4325   -0.3067 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7795   -0.5709    1.1688 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3544   -0.9027   -0.6002 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0794   -1.3531   -1.1303 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0382   -1.9603   -0.9282 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9603   -1.9693    0.2225 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1992   -2.2383   -0.8474 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0909   -3.4539   -0.1882 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.9675   -2.3712    0.9153 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6475    0.0488   -0.7502 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8663    0.7145   -1.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2136    1.7917   -1.1899 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1630    0.7029    1.3967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0136    2.1567    1.0002 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549    4.2362    0.7434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0064    3.9134    1.6195 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5013    3.3228    2.3598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9965    2.8347    0.2000 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3253    0.8629   -1.8855 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8544    1.2382   -1.1592 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0708    0.0579    1.6896 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7656   -1.6507    1.4185 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7916   -0.2346    1.5870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5237   -0.7016   -1.6642 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0357   -0.4076    0.0909 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3085   -1.9904   -0.4598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5720   -1.5212   -2.1360 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4051   -2.6145   -1.7704 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0635   -3.0675    0.5191 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5667   -1.5415    1.1567 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 10 13  1  0
 13 14  2  0
 14 15  1  0
 15  2  1  0
  1 16  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  4 20  1  0
  4 21  1  0
  5 22  1  0
  5 23  1  0
  7 24  1  0
  7 25  1  0
  7 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 12 35  1  0
 13 36  1  0
 14 37  1  0
 15 38  1  0
 15 39  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(1E,4E,8E)-2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene	ChEBI
(e,e,e)-2,6,6,9-Tetramethyl-1,4,8-cycloundecatriene	ChEBI
alpha-Caryophyllene	ChEBI
Humulene	ChEBI
a-Caryophyllene	Generator
Α-caryophyllene	Generator
a-Humulene	Generator
Α-humulene	Generator
(1E,4E,8E)-a-Humulene	HMDB
(1E,4E,8E)-Α-humulene	HMDB
(±)-alpha-humulene	HMDB
(±)-α-humulene	HMDB
alpha-Humulene	ChEBI

Chemical Formula

C₁₅H₂₄

Average Molecular Weight

204.357

Monoisotopic Molecular Weight

204.187800773

IUPAC Name

(1E,4E,8E)-2,6,6,9-tetramethylcycloundeca-1,4,8-triene

Traditional Name

humulene

CAS Registry Number

6753-98-6

SMILES

C\C1=C/CC(C)(C)\C=C\C\C(C)=C\CC1

InChI Identifier

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

InChI Key

FAMPSKZZVDUYOS-HRGUGZIWSA-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

Humulane sesquiterpenoid
Sesquiterpenoid
Branched unsaturated hydrocarbon
Cyclic olefin
Unsaturated aliphatic hydrocarbon
Unsaturated hydrocarbon
Olefin
Hydrocarbon
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

alpha-humulene (CHEBI:5768 )
Humulane sesquiterpenoids (C09684 )
Humulenes (C09684 )
Humulane sesquiterpenoids (LMPR0103110001 )

Ontology

Cellular substructure

Excreta

Biofluid or Excreta

Feces (PMID: 17314143)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036467)

Source

Endogenous

Endogenous (HMDB: HMDB0036467)

Plant

Plant (HMDB: HMDB0036467)

Animal

Animal (HMDB: HMDB0036467)

Exogenous

Food

Food (HMDB: HMDB0036467)

Beverage

Fermented beverage

Beer (FooDB: FOOD00268)

Vegetable

Root vegetable

Carrot (FooDB: FOOD00245)
Wild carrot (FooDB: FOOD00072)

Fruit vegetable

Garden tomato (var.) (FooDB: FOOD00173)

Stalk vegetable

Celery stalks (FooDB: FOOD00215)

Cottonseed (FooDB: FOOD00341)
Safflower (FooDB: FOOD00042)

Herbs and Spices (FooDB: FOOD00866)

Gourd

Cucumber (FooDB: FOOD00065)

Fruit

Berry

Blackcurrant (FooDB: FOOD00155)

Tropical fruit

Citrus

Lemon (FooDB: FOOD00054)
Sweet orange (FooDB: FOOD00057)
Mandarin orange (Clementine, Tangerine) (FooDB: FOOD00056)

Exogenous (HMDB: HMDB0036467)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036467)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036467)

Lipid metabolism pathway (HMDB: HMDB0036467)

Cellular process

Cell signaling (HMDB: HMDB0036467)

Biochemical process

Lipid transport (HMDB: HMDB0036467)

Role

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	< 25 °C	Not Available
Boiling Point	99.00 to 100.00 °C. @ 3.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.014 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.592 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.011 g/L	ALOGPS
logP	6.07	ALOGPS
logP	4.88	ChemAxon
logS	-4.3	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	71.55 m³·mol⁻¹	ChemAxon
Polarizability	21.08 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	160.712	30932474
DeepCCS	[M-H]-	158.354	30932474
DeepCCS	[M-2H]-	191.308	30932474
DeepCCS	[M+Na]+	166.806	30932474
AllCCS	[M+H]+	144.1	32859911
AllCCS	[M+H-H2O]+	140.0	32859911
AllCCS	[M+NH4]+	148.0	32859911
AllCCS	[M+Na]+	149.1	32859911
AllCCS	[M-H]-	153.4	32859911
AllCCS	[M+Na-2H]-	154.0	32859911
AllCCS	[M+HCOO]-	154.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
alpha-Humulene	C\C1=C/CC(C)(C)\C=C\C\C(C)=C\CC1	1747.4	Standard polar	33892256
alpha-Humulene	C\C1=C/CC(C)(C)\C=C\C\C(C)=C\CC1	1464.1	Standard non polar	33892256
alpha-Humulene	C\C1=C/CC(C)(C)\C=C\C\C(C)=C\CC1	1451.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Humulene GC-MS (Non-derivatized) - 70eV, Positive	splash10-000i-0920000000-6a79f6794db42ee36f8b	2017-07-27	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Humulene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - alpha-Humulene GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0006-9300000000-28c84729e712b8966f10	2015-03-01	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Humulene 10V, Positive-QTOF	splash10-0a4i-0290000000-d1375940e9b7ed7922b4	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Humulene 20V, Positive-QTOF	splash10-0a4i-2930000000-cdb29a58477970796a70	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Humulene 40V, Positive-QTOF	splash10-00kr-4900000000-788e8bfc0021846819ae	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Humulene 10V, Negative-QTOF	splash10-0udi-0090000000-8ecbabe7146ad2762752	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Humulene 20V, Negative-QTOF	splash10-0udi-0390000000-984bd28446d79854bd71	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Humulene 40V, Negative-QTOF	splash10-01ri-1900000000-139cbaab33ea7f90de6c	2017-06-28	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Humulene 10V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Humulene 20V, Negative-QTOF	splash10-0udi-0090000000-7ccf03fa1149a1e9f55f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Humulene 40V, Negative-QTOF	splash10-0f79-0930000000-3fa88d27850dde91abb9	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Humulene 10V, Positive-QTOF	splash10-0a4i-0090000000-c084f3d998cc56a199d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Humulene 20V, Positive-QTOF	splash10-0a4i-0090000000-c084f3d998cc56a199d6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - alpha-Humulene 40V, Positive-QTOF	splash10-0079-0910000000-09f78ba2b16bf7aadb82	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Feces

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	23454028	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	17314143	details

Abnormal Concentrations

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

Associated OMIM IDs

None

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

Humulene

METLIN ID

Not Available

PubChem Compound

5281520

PDB ID

Not Available

ChEBI ID

5768

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1027221

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Chaves JS, Leal PC, Pianowisky L, Calixto JB: Pharmacokinetics and tissue distribution of the sesquiterpene alpha-humulene in mice. Planta Med. 2008 Nov;74(14):1678-83. doi: 10.1055/s-0028-1088307. Epub 2008 Oct 24. [PubMed:18951339 ]
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.

Showing metabocard for alpha-Humulene (HMDB0036467)

MOL for HMDB0036467 (alpha-Humulene)

3D MOL for HMDB0036467 (alpha-Humulene)

3D SDF for HMDB0036467 (alpha-Humulene)

3D-SDF for HMDB0036467 (alpha-Humulene)

PDB for HMDB0036467 (alpha-Humulene)

3D PDB for HMDB0036467 (alpha-Humulene)

SMILES for HMDB0036467 (alpha-Humulene)

INCHI for HMDB0036467 (alpha-Humulene)

Structure for HMDB0036467 (alpha-Humulene)

3D Structure for HMDB0036467 (alpha-Humulene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra