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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-11 21:57:57 UTC

Update Date

2022-09-22 18:34:26 UTC

HMDB ID

HMDB0036789

Secondary Accession Numbers

HMDB36789

Metabolite Identification

Common Name

Caryophyllene alpha-oxide

Description

Caryophyllene alpha-oxide, also known as beta-caryophyllene epoxide, belongs to the class of organic compounds known as sesquiterpenoids. These are terpenes with three consecutive isoprene units. Based on a literature review a small amount of articles have been published on Caryophyllene alpha-oxide.

Structure

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

HMDB0036789
     RDKit          3D
Caryophyllene alpha-oxide
 40 42  0  0  0  0  0  0  0  0999 V2000
    0.3327    3.1413   -0.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0887    2.0840    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2934    1.9314    0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1317    1.2565   -0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9621    0.1735    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072   -0.3165    1.4458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4511   -1.1278    0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4726   -2.2658    0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1907   -1.5269   -0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0579   -1.2128    0.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753   -0.2439   -0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0753    1.0683    0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4169    1.1390   -0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3903   -0.3992   -0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8632   -0.8970    1.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0767   -0.9414   -1.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4182    3.8761   -0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3152    3.2990   -1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6900    2.9368    0.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014    1.3376    1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8011    2.0672   -0.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5349    0.9174   -1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0595    0.3625    0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779   -2.8894    1.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4859   -1.8698    0.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5508   -2.8351   -0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1252   -1.0772   -1.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565   -2.6388   -0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6672   -2.1100    0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596   -0.8242    1.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6348   -0.0993   -1.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1734    0.8267    1.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2419    1.5060    0.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3704    1.5623   -1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0018   -1.0353    1.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106   -1.8632    1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5709   -0.1502    1.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1518   -0.6218   -1.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6653   -0.5005   -2.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0896   -2.0390   -1.4455 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
 12  2  1  0
  7  5  1  0
 14 11  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END

  Mrv0541 05061309202D          

 16 18  0  0  0  0            999 V2000
    4.4562    1.0467    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8458   -1.3842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8972   -2.0635    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7241   -1.8557    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1544    0.6831    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3822    0.3928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5916   -1.6518    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7666   -1.6605    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.1666   -0.4356    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9326    0.4091    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3526   -0.3009    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2179   -1.1149    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9773   -0.3260    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0319   -1.2496    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1291   -1.1369    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3509   -0.8629    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  7  1  0  0  0  0
 10  1  2  0  0  0  0
 10  5  1  0  0  0  0
 11  9  1  0  0  0  0
 11 10  1  0  0  0  0
 12  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13  6  1  0  0  0  0
 14  2  1  0  0  0  0
 14  3  1  0  0  0  0
 14  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15  4  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  1  0  0  0  0
 16 13  1  0  0  0  0
 16 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036789

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3

> <INCHI_KEY>
NVEQFIOZRFFVFW-UHFFFAOYSA-N

> <FORMULA>
C15H24O

> <MOLECULAR_WEIGHT>
220.3505

> <EXACT_MASS>
220.18271539

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.42185064834615

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecane

> <ALOGPS_LOGP>
3.49

> <JCHEM_LOGP>
3.6185278833333334

> <ALOGPS_LOGS>
-4.50

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
3

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.224447799898045

> <JCHEM_POLAR_SURFACE_AREA>
12.53

> <JCHEM_REFRACTIVITY>
66.2129

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
6.96e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
caryophyllene oxide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036789
     RDKit          3D
Caryophyllene alpha-oxide
 40 42  0  0  0  0  0  0  0  0999 V2000
    0.3327    3.1413   -0.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0887    2.0840    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2934    1.9314    0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1317    1.2565   -0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9621    0.1735    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072   -0.3165    1.4458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4511   -1.1278    0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4726   -2.2658    0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1907   -1.5269   -0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0579   -1.2128    0.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753   -0.2439   -0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0753    1.0683    0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4169    1.1390   -0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3903   -0.3992   -0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8632   -0.8970    1.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0767   -0.9414   -1.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4182    3.8761   -0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3152    3.2990   -1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6900    2.9368    0.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014    1.3376    1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8011    2.0672   -0.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5349    0.9174   -1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0595    0.3625    0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779   -2.8894    1.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4859   -1.8698    0.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5508   -2.8351   -0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1252   -1.0772   -1.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565   -2.6388   -0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6672   -2.1100    0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596   -0.8242    1.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6348   -0.0993   -1.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1734    0.8267    1.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2419    1.5060    0.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3704    1.5623   -1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0018   -1.0353    1.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106   -1.8632    1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5709   -0.1502    1.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1518   -0.6218   -1.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6653   -0.5005   -2.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0896   -2.0390   -1.4455 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
 12  2  1  0
  7  5  1  0
 14 11  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END

HEADER    PROTEIN                                 06-MAY-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   06-MAY-13         0                                  
HETATM    1  C   UNK     0       8.318   1.954   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.912  -2.584   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.141  -3.852   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.218  -3.464   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.888   1.275   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.447   0.733   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.704  -3.083   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.164  -3.100   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       9.644  -0.813   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       7.341   0.764   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       8.125  -0.562   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.873  -2.081   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.691  -0.609   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       9.393  -2.333   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.974  -2.122   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.522  -1.611   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    6   10                                                       
CONECT    6    5   13                                                       
CONECT    7    8   12                                                       
CONECT    8    7   15                                                       
CONECT    9   11   14                                                       
CONECT   10    1    5   11                                                  
CONECT   11    9   10   12                                                  
CONECT   12    7   11   14                                                  
CONECT   13    6   15   16                                                  
CONECT   14    2    3    9   12                                             
CONECT   15    4    8   13   16                                             
CONECT   16   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   36    0
END

COMPND    HMDB0036789
HETATM    1  C1  UNL     1       0.333   3.141  -0.675  1.00  0.00           C  
HETATM    2  C2  UNL     1       0.089   2.084   0.091  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.293   1.931   0.633  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.132   1.256  -0.428  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.962   0.173   0.160  1.00  0.00           C  
HETATM    6  O1  UNL     1      -2.407  -0.317   1.446  1.00  0.00           O  
HETATM    7  C6  UNL     1      -2.451  -1.128   0.304  1.00  0.00           C  
HETATM    8  C7  UNL     1      -3.473  -2.266   0.461  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.191  -1.527  -0.381  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.058  -1.213   0.430  1.00  0.00           C  
HETATM   11  C10 UNL     1       0.875  -0.244  -0.339  1.00  0.00           C  
HETATM   12  C11 UNL     1       1.075   1.068   0.435  1.00  0.00           C  
HETATM   13  C12 UNL     1       2.417   1.139  -0.239  1.00  0.00           C  
HETATM   14  C13 UNL     1       2.390  -0.399  -0.215  1.00  0.00           C  
HETATM   15  C14 UNL     1       2.863  -0.897   1.111  1.00  0.00           C  
HETATM   16  C15 UNL     1       3.077  -0.941  -1.418  1.00  0.00           C  
HETATM   17  H1  UNL     1      -0.418   3.876  -0.911  1.00  0.00           H  
HETATM   18  H2  UNL     1       1.315   3.299  -1.092  1.00  0.00           H  
HETATM   19  H3  UNL     1      -1.690   2.937   0.915  1.00  0.00           H  
HETATM   20  H4  UNL     1      -1.301   1.338   1.571  1.00  0.00           H  
HETATM   21  H5  UNL     1      -2.801   2.067  -0.843  1.00  0.00           H  
HETATM   22  H6  UNL     1      -1.535   0.917  -1.299  1.00  0.00           H  
HETATM   23  H7  UNL     1      -4.059   0.363   0.220  1.00  0.00           H  
HETATM   24  H8  UNL     1      -3.178  -2.889   1.314  1.00  0.00           H  
HETATM   25  H9  UNL     1      -4.486  -1.870   0.661  1.00  0.00           H  
HETATM   26  H10 UNL     1      -3.551  -2.835  -0.494  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.125  -1.077  -1.415  1.00  0.00           H  
HETATM   28  H12 UNL     1      -1.156  -2.639  -0.580  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.667  -2.110   0.635  1.00  0.00           H  
HETATM   30  H14 UNL     1      -0.260  -0.824   1.427  1.00  0.00           H  
HETATM   31  H15 UNL     1       0.635  -0.099  -1.410  1.00  0.00           H  
HETATM   32  H16 UNL     1       1.173   0.827   1.513  1.00  0.00           H  
HETATM   33  H17 UNL     1       3.242   1.506   0.407  1.00  0.00           H  
HETATM   34  H18 UNL     1       2.370   1.562  -1.241  1.00  0.00           H  
HETATM   35  H19 UNL     1       2.002  -1.035   1.807  1.00  0.00           H  
HETATM   36  H20 UNL     1       3.411  -1.863   1.031  1.00  0.00           H  
HETATM   37  H21 UNL     1       3.571  -0.150   1.545  1.00  0.00           H  
HETATM   38  H22 UNL     1       4.152  -0.622  -1.364  1.00  0.00           H  
HETATM   39  H23 UNL     1       2.665  -0.501  -2.325  1.00  0.00           H  
HETATM   40  H24 UNL     1       3.090  -2.039  -1.445  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3   12
CONECT    3    4   19   20
CONECT    4    5   21   22
CONECT    5    6    7   23
CONECT    6    7
CONECT    7    8    9
CONECT    8   24   25   26
CONECT    9   10   27   28
CONECT   10   11   29   30
CONECT   11   12   14   31
CONECT   12   13   32
CONECT   13   14   33   34
CONECT   14   15   16
CONECT   15   35   36   37
CONECT   16   38   39   40
END

HMDB0036789
     RDKit          3D
Caryophyllene alpha-oxide
 40 42  0  0  0  0  0  0  0  0999 V2000
    0.3327    3.1413   -0.6747 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0887    2.0840    0.0906 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2934    1.9314    0.6330 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1317    1.2565   -0.4277 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9621    0.1735    0.1600 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4072   -0.3165    1.4458 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4511   -1.1278    0.3045 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4726   -2.2658    0.4606 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1907   -1.5269   -0.3807 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0579   -1.2128    0.4297 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8753   -0.2439   -0.3390 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0753    1.0683    0.4346 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4169    1.1390   -0.2387 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3903   -0.3992   -0.2149 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8632   -0.8970    1.1106 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0767   -0.9414   -1.4185 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4182    3.8761   -0.9115 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3152    3.2990   -1.0921 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6900    2.9368    0.9148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3014    1.3376    1.5710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8011    2.0672   -0.8431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5349    0.9174   -1.2992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0595    0.3625    0.2201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1779   -2.8894    1.3136 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4859   -1.8698    0.6613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5508   -2.8351   -0.4939 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1252   -1.0772   -1.4148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1565   -2.6388   -0.5798 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6672   -2.1100    0.6346 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2596   -0.8242    1.4267 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6348   -0.0993   -1.4105 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1734    0.8267    1.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2419    1.5060    0.4066 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3704    1.5623   -1.2410 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0018   -1.0353    1.8065 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4106   -1.8632    1.0312 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5709   -0.1502    1.5454 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1518   -0.6218   -1.3643 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6653   -0.5005   -2.3248 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0896   -2.0390   -1.4455 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
 12  2  1  0
  7  5  1  0
 14 11  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  4 21  1  0
  4 22  1  0
  5 23  1  0
  8 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 10 30  1  0
 11 31  1  0
 12 32  1  0
 13 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Caryophyllene a-oxide	Generator
Caryophyllene α-oxide	Generator
(-)-beta-Caryophyllene epoxide	HMDB
(-)-Epoxydihydrocaryophyllene	HMDB
beta-Caryophyllene epoxide	HMDB
beta-Caryophyllene oxide	HMDB
Caryophylene oxide	HMDB
Caryophyllene epoxide	HMDB
Caryophyllene oxyde	HMDB
Caryophyllene oxide	HMDB

Chemical Formula

C₁₅H₂₄O

Average Molecular Weight

220.3505

Monoisotopic Molecular Weight

220.18271539

IUPAC Name

4,12,12-trimethyl-9-methylidene-5-oxatricyclo[8.2.0.0⁴,⁶]dodecane

Traditional Name

caryophyllene oxide

CAS Registry Number

1139-30-6

SMILES

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

InChI Identifier

InChI=1S/C15H24O/c1-10-5-6-13-15(4,16-13)8-7-12-11(10)9-14(12,2)3/h11-13H,1,5-9H2,2-4H3

InChI Key

NVEQFIOZRFFVFW-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
Organooxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0036789)
Membrane (HMDB: HMDB0036789)

Source

Exogenous

Exogenous (HMDB: HMDB0036789)

Cottonseed (FooDB: FOOD00341)

Herb

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Endogenous (HMDB: HMDB0036789)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	63.5 - 64 °C	Not Available
Boiling Point	279.68 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	2.21 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.429 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.007 g/L	ALOGPS
logP	3.49	ALOGPS
logP	3.62	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	12.53 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	66.21 m³·mol⁻¹	ChemAxon
Polarizability	26.42 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]+	153.805	31661259
DarkChem	[M-H]-	149.986	31661259
DeepCCS	[M-2H]-	188.584	30932474
DeepCCS	[M+Na]+	163.811	30932474
AllCCS	[M+H]+	152.8	32859911
AllCCS	[M+H-H2O]+	149.0	32859911
AllCCS	[M+NH4]+	156.4	32859911
AllCCS	[M+Na]+	157.4	32859911
AllCCS	[M-H]-	160.8	32859911
AllCCS	[M+Na-2H]-	161.0	32859911
AllCCS	[M+HCOO]-	161.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Caryophyllene alpha-oxide	CC12CCC3C(CC3(C)C)C(=C)CCC1O2	2035.5	Standard polar	33892256
Caryophyllene alpha-oxide	CC12CCC3C(CC3(C)C)C(=C)CCC1O2	1550.9	Standard non polar	33892256
Caryophyllene alpha-oxide	CC12CCC3C(CC3(C)C)C(=C)CCC1O2	1584.4	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 - Caryophyllene alpha-oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-03di-2920000000-d2a03a5c7a66db83ceba	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Caryophyllene alpha-oxide 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 - Caryophyllene alpha-oxide 10V, Positive-QTOF	splash10-00di-0090000000-f8f0be1391f197a799e1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 20V, Positive-QTOF	splash10-0fk9-2490000000-fa2d7bb36e26ed264487	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 40V, Positive-QTOF	splash10-0pb9-9400000000-abbf14c22de1acb12c5a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 10V, Positive-QTOF	splash10-00di-0090000000-f8f0be1391f197a799e1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 20V, Positive-QTOF	splash10-0fk9-2490000000-fa2d7bb36e26ed264487	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 40V, Positive-QTOF	splash10-0pb9-9400000000-abbf14c22de1acb12c5a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 10V, Positive-QTOF	splash10-00di-0090000000-f8f0be1391f197a799e1	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 20V, Positive-QTOF	splash10-0fk9-2490000000-fa2d7bb36e26ed264487	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 40V, Positive-QTOF	splash10-0pb9-9400000000-abbf14c22de1acb12c5a	2015-04-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 10V, Negative-QTOF	splash10-014i-0090000000-0c846f045345079a830d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 20V, Negative-QTOF	splash10-014i-1190000000-c8390951524f03b71269	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 40V, Negative-QTOF	splash10-0pdi-8930000000-6906b65254e00eb83985	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 10V, Negative-QTOF	splash10-014i-0090000000-0c846f045345079a830d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 20V, Negative-QTOF	splash10-014i-1190000000-c8390951524f03b71269	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 40V, Negative-QTOF	splash10-0pdi-8930000000-6906b65254e00eb83985	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 10V, Negative-QTOF	splash10-014i-0090000000-0c846f045345079a830d	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 20V, Negative-QTOF	splash10-014i-1190000000-c8390951524f03b71269	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 40V, Negative-QTOF	splash10-0pdi-8930000000-6906b65254e00eb83985	2015-04-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 10V, Positive-QTOF	splash10-0fk9-0190000000-86d27f80d48351d7768e	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 20V, Positive-QTOF	splash10-0a4i-9760000000-2b1f639fb3d3df83de23	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 40V, Positive-QTOF	splash10-06r7-9500000000-f6be54a6f8d006ed9548	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 10V, Negative-QTOF	splash10-014i-0090000000-4af4c4ee1c4acef7e18b	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 20V, Negative-QTOF	splash10-014i-0090000000-d46df74fb0403a6b84f0	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Caryophyllene alpha-oxide 40V, Negative-QTOF	splash10-014i-0090000000-554eee2e2df3c86c8810	2021-09-23	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details
Urine	Detected but not Quantified	Not Quantified	Not Specified	Not Specified	Cancer patients undergoing total body irradiation	31424920	details

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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14350

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1023631

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 Caryophyllene alpha-oxide (HMDB0036789)

MOL for HMDB0036789 (Caryophyllene alpha-oxide)

3D MOL for HMDB0036789 (Caryophyllene alpha-oxide)

3D SDF for HMDB0036789 (Caryophyllene alpha-oxide)

3D-SDF for HMDB0036789 (Caryophyllene alpha-oxide)

PDB for HMDB0036789 (Caryophyllene alpha-oxide)

3D PDB for HMDB0036789 (Caryophyllene alpha-oxide)

SMILES for HMDB0036789 (Caryophyllene alpha-oxide)

INCHI for HMDB0036789 (Caryophyllene alpha-oxide)

Structure for HMDB0036789 (Caryophyllene alpha-oxide)

3D Structure for HMDB0036789 (Caryophyllene alpha-oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra