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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:36:27 UTC

Update Date

2022-03-07 02:54:56 UTC

HMDB ID

HMDB0036466

Secondary Accession Numbers

HMDB36466

Metabolite Identification

Common Name

Zerumbone oxide

Description

Zerumbone oxide belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety. Zerumbone oxide has been detected, but not quantified in, herbs and spices. This could make zerumbone oxide a potential biomarker for the consumption of these foods. Based on a literature review very few articles have been published on Zerumbone oxide.

Structure

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

HMDB0036466
     RDKit          3D
Zerumbone oxide
 39 40  0  0  0  0  0  0  0  0999 V2000
    3.1639    0.6523    1.9619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4343    0.0985    0.7323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0010    1.0974    0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532    0.8577   -1.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1850    1.8662   -1.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2303    1.5779   -1.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0514    2.6989   -2.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313    1.6162    0.1492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9909    0.6134   -0.6823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6982   -0.8178   -0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0222   -1.4393    0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9920   -2.4798    1.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6175   -0.6244    1.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0534   -2.3087   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3328   -2.2050   -0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3102   -1.3104    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4052   -1.9227    0.9435 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1331    1.0641    1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5356    1.4061    2.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3650   -0.1219    2.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    2.1677    0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0410    1.1414   -2.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0458   -0.1603   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5003    2.7373   -0.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3929    2.4202   -2.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0949    2.3692   -2.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9149    3.6199   -1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5020    2.8350   -3.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1424    0.7373   -0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6211   -1.4614   -0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1655   -1.0361   -1.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9019   -1.9508    1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1318   -3.3171    0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5001   -2.8270    2.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777   -1.1284    2.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3969   -0.6890    2.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2863    0.4069    1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4841   -3.1297   -0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8027   -3.0536   -0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  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  2  0
 15 16  1  0
 16 17  2  0
 16  2  1  0
  9  6  1  0
  1 18  1  0
  1 19  1  0
  1 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
  7 27  1  0
  7 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
M  END


  Mrv0541 05061309092D          

 17 18  0  0  0  0            999 V2000
    4.5726   -3.0979    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6914    0.5944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7026    0.1032    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5931   -2.7322    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5278   -2.3343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1636   -2.8600    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4040   -1.1538    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7546   -2.6221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2833   -0.3377    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0878   -0.9315    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9368   -2.5722    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0741   -1.7587    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2561   -1.2829    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4698   -0.2003    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1188   -2.0964    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8534   -1.4878    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4830   -1.5707    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  8  5  1  0  0  0  0
  9  7  2  0  0  0  0
 11  1  1  0  0  0  0
 11  6  2  0  0  0  0
 12  7  1  0  0  0  0
 12 11  1  0  0  0  0
 13 10  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 10  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 12  2  0  0  0  0
 17 13  1  0  0  0  0
 17 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036466

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C1=C\CCC2(C)OC2CC(C)(C)\C=C\C1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O2/c1-11-6-5-8-15(4)13(17-15)10-14(2,3)9-7-12(11)16/h6-7,9,13H,5,8,10H2,1-4H3/b9-7+,11-6-

> <INCHI_KEY>
UXYYOHOTPOQJPD-MHLOZHTBSA-N

> <FORMULA>
C15H22O2

> <MOLECULAR_WEIGHT>
234.334

> <EXACT_MASS>
234.161979948

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
26.970566602385176

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(4Z,7E)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one

> <ALOGPS_LOGP>
3.58

> <JCHEM_LOGP>
3.6699593813333324

> <ALOGPS_LOGS>
-3.81

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.007930960006638

> <JCHEM_POLAR_SURFACE_AREA>
29.6

> <JCHEM_REFRACTIVITY>
70.9789

> <JCHEM_ROTATABLE_BOND_COUNT>
0

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.62e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(4Z,7E)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036466
     RDKit          3D
Zerumbone oxide
 39 40  0  0  0  0  0  0  0  0999 V2000
    3.1639    0.6523    1.9619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4343    0.0985    0.7323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0010    1.0974    0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532    0.8577   -1.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1850    1.8662   -1.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2303    1.5779   -1.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0514    2.6989   -2.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313    1.6162    0.1492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9909    0.6134   -0.6823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6982   -0.8178   -0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0222   -1.4393    0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9920   -2.4798    1.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6175   -0.6244    1.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0534   -2.3087   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3328   -2.2050   -0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3102   -1.3104    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4052   -1.9227    0.9435 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1331    1.0641    1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5356    1.4061    2.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3650   -0.1219    2.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    2.1677    0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0410    1.1414   -2.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0458   -0.1603   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5003    2.7373   -0.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3929    2.4202   -2.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0949    2.3692   -2.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9149    3.6199   -1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5020    2.8350   -3.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1424    0.7373   -0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6211   -1.4614   -0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1655   -1.0361   -1.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9019   -1.9508    1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1318   -3.3171    0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5001   -2.8270    2.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777   -1.1284    2.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3969   -0.6890    2.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2863    0.4069    1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4841   -3.1297   -0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8027   -3.0536   -0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  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  2  0
 15 16  1  0
 16 17  2  0
 16  2  1  0
  9  6  1  0
  1 18  1  0
  1 19  1  0
  1 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
  7 27  1  0
  7 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
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       8.536  -5.783   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       5.024   1.110   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       3.178   0.193   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       1.107  -5.100   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       4.719  -4.357   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       5.905  -5.339   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.354  -2.154   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       3.275  -4.895   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       6.129  -0.630   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.897  -1.739   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       7.349  -4.801   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       7.605  -3.283   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       2.345  -2.395   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       4.610  -0.374   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.088  -3.913   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.060  -2.777   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       0.902  -2.932   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   14                                                            
CONECT    3   14                                                            
CONECT    4   15                                                            
CONECT    5    6    8                                                       
CONECT    6    5   11                                                       
CONECT    7    9   12                                                       
CONECT    8    5   15                                                       
CONECT    9    7   14                                                       
CONECT   10   13   14                                                       
CONECT   11    1    6   12                                                  
CONECT   12    7   11   16                                                  
CONECT   13   10   15   17                                                  
CONECT   14    2    3    9   10                                             
CONECT   15    4    8   13   17                                             
CONECT   16   12                                                            
CONECT   17   13   15                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   36    0
END

COMPND    HMDB0036466
HETATM    1  C1  UNL     1       3.164   0.652   1.962  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.434   0.099   0.732  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.001   1.097   0.005  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.253   0.858  -1.252  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.185   1.866  -1.333  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.230   1.578  -1.321  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.051   2.699  -2.053  1.00  0.00           C  
HETATM    8  O1  UNL     1      -1.631   1.616   0.149  1.00  0.00           O  
HETATM    9  C8  UNL     1      -1.991   0.613  -0.682  1.00  0.00           C  
HETATM   10  C9  UNL     1      -1.698  -0.818  -0.615  1.00  0.00           C  
HETATM   11  C10 UNL     1      -1.022  -1.439   0.549  1.00  0.00           C  
HETATM   12  C11 UNL     1      -1.992  -2.480   1.200  1.00  0.00           C  
HETATM   13  C12 UNL     1      -0.618  -0.624   1.690  1.00  0.00           C  
HETATM   14  C13 UNL     1       0.053  -2.309  -0.067  1.00  0.00           C  
HETATM   15  C14 UNL     1       1.333  -2.205  -0.047  1.00  0.00           C  
HETATM   16  C15 UNL     1       2.310  -1.310   0.509  1.00  0.00           C  
HETATM   17  O2  UNL     1       3.405  -1.923   0.943  1.00  0.00           O  
HETATM   18  H1  UNL     1       4.133   1.064   1.615  1.00  0.00           H  
HETATM   19  H2  UNL     1       2.536   1.406   2.438  1.00  0.00           H  
HETATM   20  H3  UNL     1       3.365  -0.122   2.697  1.00  0.00           H  
HETATM   21  H4  UNL     1       2.143   2.168   0.232  1.00  0.00           H  
HETATM   22  H5  UNL     1       2.041   1.141  -2.055  1.00  0.00           H  
HETATM   23  H6  UNL     1       1.046  -0.160  -1.515  1.00  0.00           H  
HETATM   24  H7  UNL     1       0.500   2.737  -0.655  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.393   2.420  -2.329  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.095   2.369  -2.151  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.915   3.620  -1.462  1.00  0.00           H  
HETATM   28  H11 UNL     1      -1.502   2.835  -3.002  1.00  0.00           H  
HETATM   29  H12 UNL     1      -3.142   0.737  -0.831  1.00  0.00           H  
HETATM   30  H13 UNL     1      -2.621  -1.461  -0.815  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.165  -1.036  -1.600  1.00  0.00           H  
HETATM   32  H15 UNL     1      -2.902  -1.951   1.480  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.132  -3.317   0.487  1.00  0.00           H  
HETATM   34  H17 UNL     1      -1.500  -2.827   2.141  1.00  0.00           H  
HETATM   35  H18 UNL     1       0.278  -1.128   2.178  1.00  0.00           H  
HETATM   36  H19 UNL     1      -1.397  -0.689   2.492  1.00  0.00           H  
HETATM   37  H20 UNL     1      -0.286   0.407   1.527  1.00  0.00           H  
HETATM   38  H21 UNL     1      -0.484  -3.130  -0.610  1.00  0.00           H  
HETATM   39  H22 UNL     1       1.803  -3.054  -0.633  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   16
CONECT    3    4   21
CONECT    4    5   22   23
CONECT    5    6   24   25
CONECT    6    7    8    9
CONECT    7   26   27   28
CONECT    8    9
CONECT    9   10   29
CONECT   10   11   30   31
CONECT   11   12   13   14
CONECT   12   32   33   34
CONECT   13   35   36   37
CONECT   14   15   15   38
CONECT   15   16   39
CONECT   16   17   17
END

HMDB0036466
     RDKit          3D
Zerumbone oxide
 39 40  0  0  0  0  0  0  0  0999 V2000
    3.1639    0.6523    1.9619 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4343    0.0985    0.7323 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0010    1.0974    0.0055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2532    0.8577   -1.2523 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1850    1.8662   -1.3326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2303    1.5779   -1.3206 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0514    2.6989   -2.0525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6313    1.6162    0.1492 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9909    0.6134   -0.6823 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6982   -0.8178   -0.6149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0222   -1.4393    0.5494 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9920   -2.4798    1.2000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6175   -0.6244    1.6897 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0534   -2.3087   -0.0673 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3328   -2.2050   -0.0475 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3102   -1.3104    0.5085 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4052   -1.9227    0.9435 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.1331    1.0641    1.6149 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5356    1.4061    2.4383 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3650   -0.1219    2.6974 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1427    2.1677    0.2317 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0410    1.1414   -2.0552 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0458   -0.1603   -1.5147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5003    2.7373   -0.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3929    2.4202   -2.3287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0949    2.3692   -2.1508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9149    3.6199   -1.4624 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5020    2.8350   -3.0018 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1424    0.7373   -0.8312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6211   -1.4614   -0.8148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1655   -1.0361   -1.6004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9019   -1.9508    1.4798 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1318   -3.3171    0.4874 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5001   -2.8270    2.1415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2777   -1.1284    2.1779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3969   -0.6890    2.4924 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2863    0.4069    1.5274 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4841   -3.1297   -0.6102 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8027   -3.0536   -0.6332 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  1  0
  8  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  2  0
 15 16  1  0
 16 17  2  0
 16  2  1  0
  9  6  1  0
  1 18  1  0
  1 19  1  0
  1 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
  7 27  1  0
  7 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
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,3-Epoxy-6,9-humuladien-8-one	HMDB

Chemical Formula

C₁₅H₂₂O₂

Average Molecular Weight

234.334

Monoisotopic Molecular Weight

234.161979948

IUPAC Name

(4Z,7E)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one

Traditional Name

(4Z,7E)-1,5,9,9-tetramethyl-12-oxabicyclo[9.1.0]dodeca-4,7-dien-6-one

CAS Registry Number

22471-70-1

SMILES

C\C1=C\CCC2(C)OC2CC(C)(C)\C=C\C1=O

InChI Identifier

InChI=1S/C15H22O2/c1-11-6-5-8-15(4)13(17-15)10-14(2,3)9-7-12(11)16/h6-7,9,13H,5,8,10H2,1-4H3/b9-7+,11-6-

InChI Key

UXYYOHOTPOQJPD-MHLOZHTBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as cyclic ketones. These are organic compounds containing a ketone that is conjugated to a cyclic moiety.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Cyclic ketones

Alternative Parents

Substituents

Cyclic ketone
Oxacycle
Organoheterocyclic compound
Ether
Oxirane
Dialkyl ether
Organic oxide
Hydrocarbon derivative
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0036466)

Cellular substructure

Extracellular (HMDB: HMDB0036466)
Membrane (HMDB: HMDB0036466)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036466)

Source

Endogenous

Endogenous (HMDB: HMDB0036466)

Plant

Plant (HMDB: HMDB0036466)

Exogenous

Food

Food (HMDB: HMDB0036466)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0036466)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036466)

Nutrient

Nutrient (HMDB: HMDB0036466)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036466)

Emulsifier (HMDB: HMDB0036466)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	100 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	16.53 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.036 g/L	ALOGPS
logP	3.58	ALOGPS
logP	3.67	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Basic)	-4	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	29.6 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	70.98 m³·mol⁻¹	ChemAxon
Polarizability	26.97 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	158.748	30932474
DeepCCS	[M-H]-	156.39	30932474
DeepCCS	[M-2H]-	189.321	30932474
DeepCCS	[M+Na]+	164.842	30932474
AllCCS	[M+H]+	154.9	32859911
AllCCS	[M+H-H2O]+	151.0	32859911
AllCCS	[M+NH4]+	158.5	32859911
AllCCS	[M+Na]+	159.5	32859911
AllCCS	[M-H]-	161.9	32859911
AllCCS	[M+Na-2H]-	162.2	32859911
AllCCS	[M+HCOO]-	162.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Zerumbone oxide	C\C1=C\CCC2(C)OC2CC(C)(C)\C=C\C1=O	2426.0	Standard polar	33892256
Zerumbone oxide	C\C1=C\CCC2(C)OC2CC(C)(C)\C=C\C1=O	1784.8	Standard non polar	33892256
Zerumbone oxide	C\C1=C\CCC2(C)OC2CC(C)(C)\C=C\C1=O	1836.3	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 - Zerumbone oxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-0090000000-e06da1027e912fa046fc	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zerumbone oxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Zerumbone 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 - Zerumbone oxide 10V, Positive-QTOF	splash10-000i-0190000000-bb209aeca758a3111b0f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zerumbone oxide 20V, Positive-QTOF	splash10-014r-3490000000-f123ea0b12e7d4a65343	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zerumbone oxide 40V, Positive-QTOF	splash10-0ldi-9100000000-de56c25476eed599158d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zerumbone oxide 10V, Negative-QTOF	splash10-001i-0090000000-bb9019f3ad084eb261df	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zerumbone oxide 20V, Negative-QTOF	splash10-001i-0190000000-16bbe26e95e35e20887f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zerumbone oxide 40V, Negative-QTOF	splash10-0670-9410000000-ce8489489d427d0b8d55	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zerumbone oxide 10V, Negative-QTOF	splash10-001i-0090000000-9087f47ed0ae51229a17	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zerumbone oxide 20V, Negative-QTOF	splash10-001i-0090000000-60a43b0a01aedb78d2e2	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zerumbone oxide 40V, Negative-QTOF	splash10-02u0-0190000000-a8740ae05524cfb1cb74	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zerumbone oxide 10V, Positive-QTOF	splash10-00kr-0090000000-7bfda56ba04dcffa4154	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zerumbone oxide 20V, Positive-QTOF	splash10-014j-0590000000-8a8688099d78c88fa421	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Zerumbone oxide 40V, Positive-QTOF	splash10-0fr2-0590000000-c2b6ab190b2940d32104	2021-09-25	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

FDB015359

KNApSAcK ID

C00012468

Chemspider ID

4576298

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5463724

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1855361

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 Zerumbone oxide (HMDB0036466)

MOL for HMDB0036466 (Zerumbone oxide)

3D MOL for HMDB0036466 (Zerumbone oxide)

3D SDF for HMDB0036466 (Zerumbone oxide)

3D-SDF for HMDB0036466 (Zerumbone oxide)

PDB for HMDB0036466 (Zerumbone oxide)

3D PDB for HMDB0036466 (Zerumbone oxide)

SMILES for HMDB0036466 (Zerumbone oxide)

INCHI for HMDB0036466 (Zerumbone oxide)

Structure for HMDB0036466 (Zerumbone oxide)

3D Structure for HMDB0036466 (Zerumbone oxide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra