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Showing metabocard for Hydroxycaryophyllene (HMDB0302633)

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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2021-09-23 19:17:20 UTC
Update Date2021-09-23 19:17:20 UTC
HMDB IDHMDB0302633
Secondary Accession NumbersNone
Metabolite Identification
Common NameHydroxycaryophyllene
DescriptionHydroxycaryophyllene 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
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MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0302633 (Hydroxycaryophyllene)


  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
Download

3D MOL for HMDB0302633 (Hydroxycaryophyllene)

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
Download

3D SDF for HMDB0302633 (Hydroxycaryophyllene)


  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

$$$$
Download

3D-SDF for HMDB0302633 (Hydroxycaryophyllene)

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
Download

PDB for HMDB0302633 (Hydroxycaryophyllene)

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
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3D PDB for HMDB0302633 (Hydroxycaryophyllene)

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
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SMILES for HMDB0302633 (Hydroxycaryophyllene)

CC12CCC3C(CC3(C)CO)C(=C)CCC1O2
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INCHI for HMDB0302633 (Hydroxycaryophyllene)

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
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View in JSmolView Stereo Labels
SynonymsNot Available
Chemical FormulaC15H24O2
Average Molecular Weight236.3499
Monoisotopic Molecular Weight236.177630012
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 NumberNot 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 KeyXLKXIWMHACWINL-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassSesquiterpenoids
Direct ParentSesquiterpenoids
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 FrameworkAliphatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Physiological effectNot Available
Disposition
Source
ProcessNot Available
RoleNot Available
Physical Properties
StateNot Available
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
logP2.3ALOGPS
logP2.34ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)18.17ChemAxon
pKa (Strongest Basic)-1.4ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area32.76 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity67.99 m³·mol⁻¹ChemAxon
Polarizability27.35 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
AllCCS[M+H]+157.32932859911
AllCCS[M+H-H2O]+153.66532859911
AllCCS[M+Na]+161.71432859911
AllCCS[M+NH4]+160.73432859911
AllCCS[M-H]-162.932859911
AllCCS[M+Na-2H]-163.11632859911
AllCCS[M+HCOO]-163.46432859911
DeepCCS[M-2H]-188.79830932474
DeepCCS[M+Na]+163.73330932474

Predicted Retention Times

Underivatized

Chromatographic MethodRetention TimeReference
Predicted by Siyang on May 30, 202213.2168 minutes33406817
Predicted by Siyang using ReTip algorithm on June 8, 20221.91 minutes32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid2264.7 seconds40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid327.8 seconds40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid175.0 seconds40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid172.6 seconds40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid191.2 seconds40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid609.7 seconds40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid656.8 seconds40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)79.7 seconds40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid1074.1 seconds40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid361.4 seconds40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid1288.7 seconds40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid441.7 seconds40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid371.4 seconds40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate360.3 seconds40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA400.8 seconds40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water35.3 seconds40023050

Predicted Kovats Retention Indices

Not Available
Spectra

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxycaryophyllene 10V, Positive-QTOFsplash10-00kr-0090000000-56ce7a5cc9e1ba0178e82016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxycaryophyllene 20V, Positive-QTOFsplash10-014i-1290000000-a0ad45c22a14937333ee2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxycaryophyllene 40V, Positive-QTOFsplash10-0pb9-9710000000-2cb6fa8b8aa80ec7004c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxycaryophyllene 10V, Negative-QTOFsplash10-000i-0090000000-7f492fec2d6fd6cd93732016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxycaryophyllene 20V, Negative-QTOFsplash10-05n0-0090000000-d1bd8e64de2b0ba6fc7d2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxycaryophyllene 40V, Negative-QTOFsplash10-0550-4930000000-82d2d49450f8cf5626632016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxycaryophyllene 10V, Positive-QTOFsplash10-014i-0190000000-154988cb0b2c859d7dc92021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxycaryophyllene 20V, Positive-QTOFsplash10-016r-6970000000-3de64ae6487cfaef49b82021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxycaryophyllene 40V, Positive-QTOFsplash10-0006-7900000000-3219d1815647e0a5ca112021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxycaryophyllene 10V, Negative-QTOFsplash10-000i-0090000000-e02951d35fc2f04357332021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxycaryophyllene 20V, Negative-QTOFsplash10-000i-0090000000-fbefaa77cb94df960d662021-10-21Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Hydroxycaryophyllene 40V, Negative-QTOFsplash10-07ci-0290000000-aaa563a1667c939b6b252021-10-21Wishart LabView Spectrum
Biological Properties
Cellular LocationsNot Available
Biospecimen LocationsNot Available
Tissue LocationsNot Available
Pathways
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID137227
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNot Available
METLIN IDNot Available
PubChem Compound155791
PDB IDNot Available
ChEBI IDNot Available
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available