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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2021-09-23 19:17:20 UTC

Update Date

2021-09-23 19:17:20 UTC

HMDB ID

HMDB0302633

Secondary Accession Numbers

None

Metabolite Identification

Common Name

Hydroxycaryophyllene

Description

Hydroxycaryophyllene is a member of the class of compounds known as sesquiterpenoids. Sesquiterpenoids are terpenes with three consecutive isoprene units. Hydroxycaryophyllene is practically insoluble (in water) and an extremely weak acidic compound (based on its pKa). Hydroxycaryophyllene can be found in fig, which makes hydroxycaryophyllene a potential biomarker for the consumption of this food product.

Structure

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

HMDB0302633
     RDKit          3D
Hydroxycaryophyllene
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.8758    3.1048    0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1707    2.0680   -0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2796    2.1108    0.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1197    1.1270   -0.6899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0311    0.3393    0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6540   -0.7291   -0.5699 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6587   -0.9296    0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4233   -1.7084    1.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3851   -1.5102    0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1361   -0.7637    0.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6970   -0.3830   -0.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617    1.0223   -0.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3160    0.9210   -0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833   -0.6006   -0.5199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8374   -1.2135   -1.7246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6853   -1.2420    0.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071   -0.5618    1.8922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4412    3.9375    0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452    3.1301   -0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7129    3.1304   -0.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4724    2.0948    1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5255    0.4393   -1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8193    1.6108   -1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7982    0.9260    0.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2259   -1.0516    2.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8690   -2.5860    1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7623   -2.0014    2.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685   -2.5889    0.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3593   -1.5804   -1.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4592   -1.5393    1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3459    0.0078    1.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3598   -0.9741   -1.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9222    1.2247   -2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0703    1.2576   -1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4496    1.2629    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5850   -0.5154   -2.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3087   -2.1905   -1.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0391   -1.4195   -2.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3312   -2.2786    0.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8080   -1.2602    0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1930   -0.0872    2.2635 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  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 12  2  1  0
  7  5  1  0
 14 11  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
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
M  END

  Mrv0541 02241221402D          

 17 19  0  0  0  0            999 V2000
    0.8002    0.1423    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2052   -0.5765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8427   -0.0529    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6677   -0.0616    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2940   -0.5985    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4287   -1.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2427   -1.2778    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1080   -0.4638    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8680   -0.1429    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1670    0.3590    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4839    0.8216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.0087   -2.1226    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5323   -2.7601    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2305   -2.3965    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4583   -2.1062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0534   -1.3874    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4270   -0.8505    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
  6 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
  2 16  1  0  0  0  0
 16 17  1  0  0  0  0
  2 17  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0302633

> <DATABASE_NAME>
hmdb

> <SMILES>
CC12CCC3C(CC3(C)CO)C(=C)CCC1O2

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-10-4-5-13-15(3,17-13)7-6-12-11(10)8-14(12,2)9-16/h11-13,16H,1,4-9H2,2-3H3

> <INCHI_KEY>
XLKXIWMHACWINL-UHFFFAOYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.3499

> <EXACT_MASS>
236.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.346795532487

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}methanol

> <ALOGPS_LOGP>
2.30

> <JCHEM_LOGP>
2.3377567266666666

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
18.16628022543005

> <JCHEM_PKA_STRONGEST_BASIC>
-1.4131978016769473

> <JCHEM_POLAR_SURFACE_AREA>
32.76

> <JCHEM_REFRACTIVITY>
67.9876

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.23e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}methanol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0302633
     RDKit          3D
Hydroxycaryophyllene
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.8758    3.1048    0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1707    2.0680   -0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2796    2.1108    0.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1197    1.1270   -0.6899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0311    0.3393    0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6540   -0.7291   -0.5699 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6587   -0.9296    0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4233   -1.7084    1.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3851   -1.5102    0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1361   -0.7637    0.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6970   -0.3830   -0.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617    1.0223   -0.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3160    0.9210   -0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833   -0.6006   -0.5199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8374   -1.2135   -1.7246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6853   -1.2420    0.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071   -0.5618    1.8922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4412    3.9375    0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452    3.1301   -0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7129    3.1304   -0.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4724    2.0948    1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5255    0.4393   -1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8193    1.6108   -1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7982    0.9260    0.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2259   -1.0516    2.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8690   -2.5860    1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7623   -2.0014    2.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685   -2.5889    0.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3593   -1.5804   -1.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4592   -1.5393    1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3459    0.0078    1.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3598   -0.9741   -1.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9222    1.2247   -2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0703    1.2576   -1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4496    1.2629    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5850   -0.5154   -2.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3087   -2.1905   -1.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0391   -1.4195   -2.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3312   -2.2786    0.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8080   -1.2602    0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1930   -0.0872    2.2635 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  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 12  2  1  0
  7  5  1  0
 14 11  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
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  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       1.494   0.266   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       2.250  -1.076   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.440  -0.099   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       4.980  -0.115   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       6.149  -1.117   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       6.400  -2.637   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       7.920  -2.385   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       7.668  -0.866   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.087  -0.267   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.778   0.670   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0       6.503   1.534   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0       5.616  -3.962   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.594  -5.152   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.164  -4.473   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.722  -3.932   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       1.966  -2.590   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       0.797  -1.588   0.000  0.00  0.00           O+0
CONECT    1    2                                                            
CONECT    2    1    3   16   17                                             
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6    8                                                  
CONECT    6    5    7   12                                                  
CONECT    7    6    8                                                       
CONECT    8    7    5    9   10                                             
CONECT    9    8                                                            
CONECT   10    8   11                                                       
CONECT   11   10                                                            
CONECT   12    6   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15    2   17                                                  
CONECT   17   16    2                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   38    0
END

COMPND    HMDB0302633
HETATM    1  C1  UNL     1      -0.876   3.105   0.179  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.171   2.068  -0.265  1.00  0.00           C  
HETATM    3  C3  UNL     1       1.280   2.111   0.043  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.120   1.127  -0.690  1.00  0.00           C  
HETATM    5  C5  UNL     1       3.031   0.339   0.221  1.00  0.00           C  
HETATM    6  O1  UNL     1       3.654  -0.729  -0.570  1.00  0.00           O  
HETATM    7  C6  UNL     1       2.659  -0.930   0.546  1.00  0.00           C  
HETATM    8  C7  UNL     1       3.423  -1.708   1.623  1.00  0.00           C  
HETATM    9  C8  UNL     1       1.385  -1.510   0.051  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.136  -0.764   0.514  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.697  -0.383  -0.643  1.00  0.00           C  
HETATM   12  C11 UNL     1      -0.862   1.022  -0.997  1.00  0.00           C  
HETATM   13  C12 UNL     1      -2.316   0.921  -0.499  1.00  0.00           C  
HETATM   14  C13 UNL     1      -2.183  -0.601  -0.520  1.00  0.00           C  
HETATM   15  C14 UNL     1      -2.837  -1.213  -1.725  1.00  0.00           C  
HETATM   16  C15 UNL     1      -2.685  -1.242   0.735  1.00  0.00           C  
HETATM   17  O2  UNL     1      -2.407  -0.562   1.892  1.00  0.00           O  
HETATM   18  H1  UNL     1      -0.441   3.937   0.732  1.00  0.00           H  
HETATM   19  H2  UNL     1      -1.945   3.130  -0.021  1.00  0.00           H  
HETATM   20  H3  UNL     1       1.713   3.130  -0.223  1.00  0.00           H  
HETATM   21  H4  UNL     1       1.472   2.095   1.161  1.00  0.00           H  
HETATM   22  H5  UNL     1       1.525   0.439  -1.286  1.00  0.00           H  
HETATM   23  H6  UNL     1       2.819   1.611  -1.439  1.00  0.00           H  
HETATM   24  H7  UNL     1       3.798   0.926   0.734  1.00  0.00           H  
HETATM   25  H8  UNL     1       4.226  -1.052   2.023  1.00  0.00           H  
HETATM   26  H9  UNL     1       3.869  -2.586   1.097  1.00  0.00           H  
HETATM   27  H10 UNL     1       2.762  -2.001   2.446  1.00  0.00           H  
HETATM   28  H11 UNL     1       1.369  -2.589   0.366  1.00  0.00           H  
HETATM   29  H12 UNL     1       1.359  -1.580  -1.078  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.459  -1.539   1.089  1.00  0.00           H  
HETATM   31  H14 UNL     1       0.346   0.008   1.252  1.00  0.00           H  
HETATM   32  H15 UNL     1      -0.360  -0.974  -1.555  1.00  0.00           H  
HETATM   33  H16 UNL     1      -0.922   1.225  -2.107  1.00  0.00           H  
HETATM   34  H17 UNL     1      -3.070   1.258  -1.203  1.00  0.00           H  
HETATM   35  H18 UNL     1      -2.450   1.263   0.555  1.00  0.00           H  
HETATM   36  H19 UNL     1      -3.585  -0.515  -2.155  1.00  0.00           H  
HETATM   37  H20 UNL     1      -3.309  -2.190  -1.496  1.00  0.00           H  
HETATM   38  H21 UNL     1      -2.039  -1.419  -2.485  1.00  0.00           H  
HETATM   39  H22 UNL     1      -2.331  -2.279   0.796  1.00  0.00           H  
HETATM   40  H23 UNL     1      -3.808  -1.260   0.637  1.00  0.00           H  
HETATM   41  H24 UNL     1      -3.193  -0.087   2.264  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3   12
CONECT    3    4   20   21
CONECT    4    5   22   23
CONECT    5    6    7   24
CONECT    6    7
CONECT    7    8    9
CONECT    8   25   26   27
CONECT    9   10   28   29
CONECT   10   11   30   31
CONECT   11   12   14   32
CONECT   12   13   33
CONECT   13   14   34   35
CONECT   14   15   16
CONECT   15   36   37   38
CONECT   16   17   39   40
CONECT   17   41
END

HMDB0302633
     RDKit          3D
Hydroxycaryophyllene
 41 43  0  0  0  0  0  0  0  0999 V2000
   -0.8758    3.1048    0.1789 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1707    2.0680   -0.2648 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2796    2.1108    0.0435 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1197    1.1270   -0.6899 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0311    0.3393    0.2207 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6540   -0.7291   -0.5699 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.6587   -0.9296    0.5464 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4233   -1.7084    1.6227 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3851   -1.5102    0.0513 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1361   -0.7637    0.5139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6970   -0.3830   -0.6431 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8617    1.0223   -0.9967 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3160    0.9210   -0.4994 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1833   -0.6006   -0.5199 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8374   -1.2135   -1.7246 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6853   -1.2420    0.7347 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4071   -0.5618    1.8922 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4412    3.9375    0.7318 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9452    3.1301   -0.0210 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7129    3.1304   -0.2226 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4724    2.0948    1.1606 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5255    0.4393   -1.2864 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8193    1.6108   -1.4395 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7982    0.9260    0.7344 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2259   -1.0516    2.0230 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8690   -2.5860    1.0967 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7623   -2.0014    2.4458 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3685   -2.5889    0.3664 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3593   -1.5804   -1.0779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4592   -1.5393    1.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3459    0.0078    1.2522 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3598   -0.9741   -1.5547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9222    1.2247   -2.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0703    1.2576   -1.2033 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4496    1.2629    0.5551 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5850   -0.5154   -2.1549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3087   -2.1905   -1.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0391   -1.4195   -2.4845 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3312   -2.2786    0.7958 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8080   -1.2602    0.6374 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1930   -0.0872    2.2635 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  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 14 16  1  0
 16 17  1  0
 12  2  1  0
  7  5  1  0
 14 11  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
  8 25  1  0
  8 26  1  0
  8 27  1  0
  9 28  1  0
  9 29  1  0
 10 30  1  0
 10 31  1  0
 11 32  1  0
 12 33  1  0
 13 34  1  0
 13 35  1  0
 15 36  1  0
 15 37  1  0
 15 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Not Available

Chemical Formula

C₁₅H₂₄O₂

Average Molecular Weight

236.3499

Monoisotopic Molecular Weight

236.177630012

IUPAC Name

{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}methanol

Traditional Name

{4,12-dimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecan-12-yl}methanol

CAS Registry Number

Not Available

SMILES

CC12CCC3C(CC3(C)CO)C(=C)CCC1O2

InChI Identifier

InChI=1S/C15H24O2/c1-10-4-5-13-15(3,17-13)7-6-12-11(10)8-14(12,2)9-16/h11-13,16H,1,4-9H2,2-3H3

InChI Key

XLKXIWMHACWINL-UHFFFAOYSA-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
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxygen compound
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Alcohol
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Not Available

Exogenous (HMDB: HMDB0302633)

Food

Fruit

Other fruit

Fig (FooDB: FOOD00081)

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
logP	2.3	ALOGPS
logP	2.34	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	18.17	ChemAxon
pKa (Strongest Basic)	-1.4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.76 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.99 m³·mol⁻¹	ChemAxon
Polarizability	27.35 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
AllCCS	[M+H]+	157.329	32859911
AllCCS	[M+H-H2O]+	153.665	32859911
AllCCS	[M+Na]+	161.714	32859911
AllCCS	[M+NH4]+	160.734	32859911
AllCCS	[M-H]-	162.9	32859911
AllCCS	[M+Na-2H]-	163.116	32859911
AllCCS	[M+HCOO]-	163.464	32859911
DeepCCS	[M-2H]-	188.798	30932474
DeepCCS	[M+Na]+	163.733	30932474

Predicted Kovats Retention Indices

Not Available

Spectra

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycaryophyllene 10V, Positive-QTOF	splash10-00kr-0090000000-56ce7a5cc9e1ba0178e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycaryophyllene 20V, Positive-QTOF	splash10-014i-1290000000-a0ad45c22a14937333ee	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycaryophyllene 40V, Positive-QTOF	splash10-0pb9-9710000000-2cb6fa8b8aa80ec7004c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycaryophyllene 10V, Negative-QTOF	splash10-000i-0090000000-7f492fec2d6fd6cd9373	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycaryophyllene 20V, Negative-QTOF	splash10-05n0-0090000000-d1bd8e64de2b0ba6fc7d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycaryophyllene 40V, Negative-QTOF	splash10-0550-4930000000-82d2d49450f8cf562663	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycaryophyllene 10V, Positive-QTOF	splash10-014i-0190000000-154988cb0b2c859d7dc9	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycaryophyllene 20V, Positive-QTOF	splash10-016r-6970000000-3de64ae6487cfaef49b8	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycaryophyllene 40V, Positive-QTOF	splash10-0006-7900000000-3219d1815647e0a5ca11	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycaryophyllene 10V, Negative-QTOF	splash10-000i-0090000000-e02951d35fc2f0435733	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycaryophyllene 20V, Negative-QTOF	splash10-000i-0090000000-fbefaa77cb94df960d66	2021-10-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Hydroxycaryophyllene 40V, Negative-QTOF	splash10-07ci-0290000000-aaa563a1667c939b6b25	2021-10-21	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Not Available

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

Not Available

KNApSAcK ID

Not Available

Chemspider ID

137227

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

155791

PDB ID

Not Available

ChEBI ID

Not Available

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

Not Available

Showing metabocard for Hydroxycaryophyllene (HMDB0302633)

MOL for HMDB0302633 (Hydroxycaryophyllene)

3D MOL for HMDB0302633 (Hydroxycaryophyllene)

3D SDF for HMDB0302633 (Hydroxycaryophyllene)

3D-SDF for HMDB0302633 (Hydroxycaryophyllene)

PDB for HMDB0302633 (Hydroxycaryophyllene)

3D PDB for HMDB0302633 (Hydroxycaryophyllene)

SMILES for HMDB0302633 (Hydroxycaryophyllene)

INCHI for HMDB0302633 (Hydroxycaryophyllene)

Structure for HMDB0302633 (Hydroxycaryophyllene)

3D Structure for HMDB0302633 (Hydroxycaryophyllene)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

MS/MS Spectra