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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:18:32 UTC

Update Date

2022-03-07 02:55:10 UTC

HMDB ID

HMDB0037066

Secondary Accession Numbers

HMDB37066

Metabolite Identification

Common Name

beta-Caryophyllene alcohol

Description

beta-Caryophyllene alcohol, also known as caryolan-1-ol, belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ). beta-Caryophyllene alcohol is an earthy, moss, and spicy tasting compound. beta-Caryophyllene alcohol has been detected, but not quantified in, several different foods, such as citrus, fruits, herbs and spices, and pepper (spice). This could make beta-caryophyllene alcohol a potential biomarker for the consumption of these foods. Based on a literature review a small amount of articles have been published on beta-Caryophyllene alcohol.

Structure

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

HMDB0037066
     RDKit          3D
beta-Caryophyllene alcohol
 42 44  0  0  0  0  0  0  0  0999 V2000
   -2.6265    0.5254    1.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9172    0.4970    0.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8099    0.0715   -0.7440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6631   -1.3067   -1.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2331   -1.8065   -1.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4144   -0.7719   -0.8937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7218    0.3342   -1.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9389   -0.6815    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0208   -0.6977   -0.8684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8645   -1.2710    0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4901    0.1157    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8359    0.2774   -0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5381    0.4927    1.7934 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3379    0.7200   -0.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4379    1.4769    0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0176    1.6653    0.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8663    0.9733    2.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4879    1.2145    1.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8728   -0.4979    2.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9621    0.8633   -1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8546    0.0584   -0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1784   -1.3458   -2.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859   -2.0661   -0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0811   -2.7773   -1.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0439   -1.9795   -2.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4550    0.0502   -2.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6023   -1.5439    0.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287   -0.5673    1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4581   -0.9535   -1.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -1.7057    1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6870   -1.9621   -0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5242   -0.4973    0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8099    0.2936   -1.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2433    1.2511    0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5374    1.5974    1.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5531    0.1687    2.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8138   -0.0309    2.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7652    1.2808   -1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756    1.2768    1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8369    2.5522    0.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3125    2.3869    0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2916    2.3196   -0.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
  8  2  1  0
 14  9  1  0
 16  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END


  Mrv0541 02241219562D          

 16 18  0  0  0  0            999 V2000
    0.2056    1.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2056    0.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6178    0.4535    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1128   -0.2056    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9478   -0.9478    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2056   -1.3599    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6178   -2.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4535   -1.8549    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2778   -1.6078    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4428   -0.7828    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2056   -0.7006    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7835   -0.1236    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4428    0.4535    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5357    2.1028    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6178    1.2785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4428    1.3607    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 15  1  0  0  0  0
  2  3  1  0  0  0  0
  2 12  1  0  0  0  0
  3  4  1  0  0  0  0
  3 15  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
  6  8  1  0  0  0  0
  6 11  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 12  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037066

> <DATABASE_NAME>
hmdb

> <SMILES>
CC1(C)CC2C1CCC1(C)CCCC2(O)C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O/c1-13(2)9-12-11(13)5-8-14(3)6-4-7-15(12,16)10-14/h11-12,16H,4-10H2,1-3H3

> <INCHI_KEY>
FUQAYSQLAOJBBC-UHFFFAOYSA-N

> <FORMULA>
C15H26O

> <MOLECULAR_WEIGHT>
222.3663

> <EXACT_MASS>
222.198365454

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.428381521558425

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecan-1-ol

> <ALOGPS_LOGP>
3.52

> <JCHEM_LOGP>
3.427033741333333

> <ALOGPS_LOGS>
-4.38

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-0.18952770320995593

> <JCHEM_POLAR_SURFACE_AREA>
20.23

> <JCHEM_REFRACTIVITY>
66.50189999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.33e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecan-1-ol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0037066
     RDKit          3D
beta-Caryophyllene alcohol
 42 44  0  0  0  0  0  0  0  0999 V2000
   -2.6265    0.5254    1.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9172    0.4970    0.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8099    0.0715   -0.7440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6631   -1.3067   -1.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2331   -1.8065   -1.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4144   -0.7719   -0.8937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7218    0.3342   -1.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9389   -0.6815    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0208   -0.6977   -0.8684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8645   -1.2710    0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4901    0.1157    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8359    0.2774   -0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5381    0.4927    1.7934 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3379    0.7200   -0.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4379    1.4769    0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0176    1.6653    0.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8663    0.9733    2.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4879    1.2145    1.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8728   -0.4979    2.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9621    0.8633   -1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8546    0.0584   -0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1784   -1.3458   -2.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859   -2.0661   -0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0811   -2.7773   -1.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0439   -1.9795   -2.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4550    0.0502   -2.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6023   -1.5439    0.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287   -0.5673    1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4581   -0.9535   -1.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -1.7057    1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6870   -1.9621   -0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5242   -0.4973    0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8099    0.2936   -1.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2433    1.2511    0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5374    1.5974    1.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5531    0.1687    2.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8138   -0.0309    2.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7652    1.2808   -1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756    1.2768    1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8369    2.5522    0.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3125    2.3869    0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2916    2.3196   -0.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
  8  2  1  0
 14  9  1  0
 16  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       0.384   2.387   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       0.384   0.847   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -1.153   0.847   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.077  -0.384   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.769  -1.769   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -0.384  -2.538   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.153  -3.925   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.847  -3.462   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.385  -3.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.693  -1.461   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       0.384  -1.308   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       1.463  -0.231   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0       2.693   0.847   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -1.000   3.925   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.153   2.387   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      -2.693   2.540   0.000  0.00  0.00           C+0
CONECT    1    2   15                                                       
CONECT    2    1    3   12                                                  
CONECT    3    2    4   15                                                  
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7    8   11                                             
CONECT    7    6                                                            
CONECT    8    6    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   12                                                       
CONECT   11    6   12                                                       
CONECT   12    2   10   11   13                                             
CONECT   13   12                                                            
CONECT   14   15                                                            
CONECT   15    1    3   14   16                                             
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0037066
HETATM    1  C1  UNL     1      -2.626   0.525   1.733  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.917   0.497   0.372  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.810   0.072  -0.744  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.663  -1.307  -1.279  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.233  -1.807  -1.545  1.00  0.00           C  
HETATM    6  C6  UNL     1      -0.414  -0.772  -0.894  1.00  0.00           C  
HETATM    7  O1  UNL     1      -0.722   0.334  -1.742  1.00  0.00           O  
HETATM    8  C7  UNL     1      -0.939  -0.682   0.499  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.021  -0.698  -0.868  1.00  0.00           C  
HETATM   10  C9  UNL     1       1.864  -1.271   0.189  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.490   0.116   0.351  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.836   0.277  -0.295  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.538   0.493   1.793  1.00  0.00           C  
HETATM   14  C13 UNL     1       1.338   0.720  -0.446  1.00  0.00           C  
HETATM   15  C14 UNL     1       0.438   1.477   0.366  1.00  0.00           C  
HETATM   16  C15 UNL     1      -1.018   1.665   0.147  1.00  0.00           C  
HETATM   17  H1  UNL     1      -1.866   0.973   2.434  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.488   1.215   1.687  1.00  0.00           H  
HETATM   19  H3  UNL     1      -2.873  -0.498   2.029  1.00  0.00           H  
HETATM   20  H4  UNL     1      -2.962   0.863  -1.538  1.00  0.00           H  
HETATM   21  H5  UNL     1      -3.855   0.058  -0.280  1.00  0.00           H  
HETATM   22  H6  UNL     1      -3.178  -1.346  -2.257  1.00  0.00           H  
HETATM   23  H7  UNL     1      -3.186  -2.066  -0.631  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.081  -2.777  -1.015  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.044  -1.980  -2.603  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.455   0.050  -2.629  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.602  -1.544   0.806  1.00  0.00           H  
HETATM   28  H12 UNL     1      -0.229  -0.567   1.298  1.00  0.00           H  
HETATM   29  H13 UNL     1       1.458  -0.953  -1.883  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.436  -1.706   1.083  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.687  -1.962  -0.167  1.00  0.00           H  
HETATM   32  H16 UNL     1       4.524  -0.497   0.099  1.00  0.00           H  
HETATM   33  H17 UNL     1       3.810   0.294  -1.393  1.00  0.00           H  
HETATM   34  H18 UNL     1       4.243   1.251   0.039  1.00  0.00           H  
HETATM   35  H19 UNL     1       2.537   1.597   1.929  1.00  0.00           H  
HETATM   36  H20 UNL     1       3.553   0.169   2.171  1.00  0.00           H  
HETATM   37  H21 UNL     1       1.814  -0.031   2.436  1.00  0.00           H  
HETATM   38  H22 UNL     1       1.765   1.281  -1.324  1.00  0.00           H  
HETATM   39  H23 UNL     1       0.576   1.277   1.478  1.00  0.00           H  
HETATM   40  H24 UNL     1       0.837   2.552   0.336  1.00  0.00           H  
HETATM   41  H25 UNL     1      -1.312   2.387   0.987  1.00  0.00           H  
HETATM   42  H26 UNL     1      -1.292   2.320  -0.733  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    8   16
CONECT    3    4   20   21
CONECT    4    5   22   23
CONECT    5    6   24   25
CONECT    6    7    8    9
CONECT    7   26
CONECT    8   27   28
CONECT    9   10   14   29
CONECT   10   11   30   31
CONECT   11   12   13   14
CONECT   12   32   33   34
CONECT   13   35   36   37
CONECT   14   15   38
CONECT   15   16   39   40
CONECT   16   41   42
END

HMDB0037066
     RDKit          3D
beta-Caryophyllene alcohol
 42 44  0  0  0  0  0  0  0  0999 V2000
   -2.6265    0.5254    1.7333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9172    0.4970    0.3722 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8099    0.0715   -0.7440 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6631   -1.3067   -1.2787 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2331   -1.8065   -1.5448 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4144   -0.7719   -0.8937 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7218    0.3342   -1.7415 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9389   -0.6815    0.4988 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0208   -0.6977   -0.8684 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8645   -1.2710    0.1893 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4901    0.1157    0.3511 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8359    0.2774   -0.2948 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5381    0.4927    1.7934 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3379    0.7200   -0.4457 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4379    1.4769    0.3663 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0176    1.6653    0.1472 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8663    0.9733    2.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4879    1.2145    1.6867 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8728   -0.4979    2.0289 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9621    0.8633   -1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8546    0.0584   -0.2801 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1784   -1.3458   -2.2574 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1859   -2.0661   -0.6305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0811   -2.7773   -1.0151 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0439   -1.9795   -2.6026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4550    0.0502   -2.6286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6023   -1.5439    0.8062 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2287   -0.5673    1.2982 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4581   -0.9535   -1.8828 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4358   -1.7057    1.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6870   -1.9621   -0.1668 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5242   -0.4973    0.0994 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8099    0.2936   -1.3926 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2433    1.2511    0.0393 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5374    1.5974    1.9292 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5531    0.1687    2.1711 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8138   -0.0309    2.4358 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7652    1.2808   -1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5756    1.2768    1.4779 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8369    2.5522    0.3358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3125    2.3869    0.9872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2916    2.3196   -0.7328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  6  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
 11 14  1  0
 14 15  1  0
 15 16  1  0
  8  2  1  0
 14  9  1  0
 16  2  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  7 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 13 37  1  0
 14 38  1  0
 15 39  1  0
 15 40  1  0
 16 41  1  0
 16 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
b-Caryophyllene alcohol	Generator
Β-caryophyllene alcohol	Generator
4,4,8-Trimethyltricyclo(6.3.1.02,5)dodecan-1-ol	MeSH
Caryolan-1-ol	MeSH
4,4,8-Trimethyl-tricyclo(6.3.1.02,5)dodecan-1-ol	HMDB
4,4,8-trimethyltricyclo[6.3.1.02,5]Dodecan-1-ol, 9ci	HMDB
Caryophyllenol	HMDB
beta-Caryophyllene alcohol	MeSH

Chemical Formula

C₁₅H₂₆O

Average Molecular Weight

222.3663

Monoisotopic Molecular Weight

222.198365454

IUPAC Name

4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecan-1-ol

Traditional Name

4,4,8-trimethyltricyclo[6.3.1.0²,⁵]dodecan-1-ol

CAS Registry Number

472-97-9

SMILES

CC1(C)CC2C1CCC1(C)CCCC2(O)C1

InChI Identifier

InChI=1S/C15H26O/c1-13(2)9-12-11(13)5-8-14(3)6-4-7-15(12,16)10-14/h11-12,16H,4-10H2,1-3H3

InChI Key

FUQAYSQLAOJBBC-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as tertiary alcohols. Tertiary alcohols are compounds in which a hydroxy group, -OH, is attached to a saturated carbon atom R3COH (R not H ).

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Alcohols and polyols

Direct Parent

Tertiary alcohols

Alternative Parents

Substituents

Tertiary alcohol
Cyclic alcohol
Hydrocarbon derivative
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

a sesquiterpenoid (CPD-13787 )

Ontology

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037066)

Source

Endogenous

Endogenous (HMDB: HMDB0037066)

Plant

Plant (HMDB: HMDB0037066)

Exogenous

Food

Food (HMDB: HMDB0037066)

Herb and spice

Spice

Pepper (Spice) (FooDB: FOOD00139)

Herbs and Spices (FooDB: FOOD00866)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Fruits (FooDB: FOOD00871)

Exogenous (HMDB: HMDB0037066)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0037066)

Role

Biological role

Energy source (HMDB: HMDB0037066)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037066)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037066)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	94 - 96 °C	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	0.0093 g/L	ALOGPS
logP	3.52	ALOGPS
logP	3.43	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Basic)	-0.19	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	20.23 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.5 m³·mol⁻¹	ChemAxon
Polarizability	27.43 Å³	ChemAxon
Number of Rings	3	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]+	151.976	31661259
DarkChem	[M-H]-	149.61	31661259
DeepCCS	[M+H]+	157.008	30932474
DeepCCS	[M-H]-	154.65	30932474
DeepCCS	[M-2H]-	189.105	30932474
DeepCCS	[M+Na]+	164.294	30932474
AllCCS	[M+H]+	154.2	32859911
AllCCS	[M+H-H2O]+	150.6	32859911
AllCCS	[M+NH4]+	157.7	32859911
AllCCS	[M+Na]+	158.6	32859911
AllCCS	[M-H]-	161.6	32859911
AllCCS	[M+Na-2H]-	162.0	32859911
AllCCS	[M+HCOO]-	162.5	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	5.81 minutes	32390414
Predicted by Siyang on May 30, 2022	16.4335 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.26 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2294.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	482.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	200.3 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	233.8 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	437.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	751.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	728.6 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	92.0 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1338.3 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	432.9 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	1446.2 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	526.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	402.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	422.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	559.0 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.8 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
beta-Caryophyllene alcohol	CC1(C)CC2C1CCC1(C)CCCC2(O)C1	2195.4	Standard polar	33892256
beta-Caryophyllene alcohol	CC1(C)CC2C1CCC1(C)CCCC2(O)C1	1629.6	Standard non polar	33892256
beta-Caryophyllene alcohol	CC1(C)CC2C1CCC1(C)CCCC2(O)C1	1634.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
beta-Caryophyllene alcohol,1TMS,isomer #1	CC12CCCC(O[Si](C)(C)C)(C1)C1CC(C)(C)C1CC2	1763.1	Semi standard non polar	33892256
beta-Caryophyllene alcohol,1TBDMS,isomer #1	CC12CCCC(O[Si](C)(C)C(C)(C)C)(C1)C1CC(C)(C)C1CC2	2010.7	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 - beta-Caryophyllene alcohol GC-MS (Non-derivatized) - 70eV, Positive	splash10-06tf-3920000000-b68753a0c64ca8112abc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Caryophyllene alcohol GC-MS (1 TMS) - 70eV, Positive	splash10-0v7r-5290000000-2abb69265dc4b41e9d83	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - beta-Caryophyllene alcohol 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 - beta-Caryophyllene alcohol 10V, Positive-QTOF	splash10-0ab9-0090000000-f722d04da4e967382a9b	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 20V, Positive-QTOF	splash10-0ab9-1290000000-68742d2f6dacdd03ba4c	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 40V, Positive-QTOF	splash10-054x-8910000000-6d5494cbf7239c6a6288	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 10V, Negative-QTOF	splash10-00di-0090000000-df53e329d8b4cb321660	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 20V, Negative-QTOF	splash10-00di-0090000000-78f3f8caa5d303c302f1	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 40V, Negative-QTOF	splash10-0a4i-3950000000-68721e6a300ef023c3c0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 10V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 20V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 40V, Negative-QTOF	splash10-00di-0090000000-ab61d8a2af41e6ed2e49	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 10V, Positive-QTOF	splash10-00di-1290000000-b8ad223195b98618f733	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 20V, Positive-QTOF	splash10-0ac0-9660000000-c0162b1be56a39c1cd11	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - beta-Caryophyllene alcohol 40V, Positive-QTOF	splash10-00l6-9100000000-768051f4547352e86ab4	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

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

FDB016050

KNApSAcK ID

C00021969

Chemspider ID

55073

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

61125

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1014751

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for beta-Caryophyllene alcohol (HMDB0037066)

MOL for HMDB0037066 (beta-Caryophyllene alcohol)

3D MOL for HMDB0037066 (beta-Caryophyllene alcohol)

3D SDF for HMDB0037066 (beta-Caryophyllene alcohol)

3D-SDF for HMDB0037066 (beta-Caryophyllene alcohol)

PDB for HMDB0037066 (beta-Caryophyllene alcohol)

3D PDB for HMDB0037066 (beta-Caryophyllene alcohol)

SMILES for HMDB0037066 (beta-Caryophyllene alcohol)

INCHI for HMDB0037066 (beta-Caryophyllene alcohol)

Structure for HMDB0037066 (beta-Caryophyllene alcohol)

3D Structure for HMDB0037066 (beta-Caryophyllene alcohol)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra