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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 21:49:59 UTC

Update Date

2022-03-07 02:55:01 UTC

HMDB ID

HMDB0036668

Secondary Accession Numbers

HMDB36668

Metabolite Identification

Common Name

Humulene-8-hydroperoxide

Description

Humulene-8-hydroperoxide 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 Humulene-8-hydroperoxide.

Structure

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

HMDB0036668
     RDKit          3D
Humulene-8-hydroperoxide
 41 41  0  0  0  0  0  0  0  0999 V2000
   -1.1189    3.5553    1.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8761    2.2402    0.3537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696    1.6576   -0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403    0.4450   -0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7024   -0.8866   -0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0035   -1.7871   -0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4758   -0.9283    1.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7332   -1.6262   -1.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483   -1.7985   -0.9596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4971   -1.3072    0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1967   -2.5070    0.4216 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171   -2.8054    1.6784 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5274   -0.3900   -0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9800   -0.8275   -0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4001    0.7967   -0.9090 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0122    1.3246   -1.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4491    1.7659    0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1449    4.0628    1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5109    3.2005    2.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8650    4.1564    0.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9548    2.1753    0.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6881    0.4333   -1.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1760    0.3407   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7660   -2.7839    0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1930   -1.8533   -1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8236   -1.2685    0.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063   -0.9110    1.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9677   -0.0994    1.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1070   -1.9456    1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2258   -2.1154   -1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0626   -2.4043   -1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0232   -1.0594    1.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953   -2.3837    2.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228    0.0216    0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0588   -1.5546    0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2838   -1.2709   -1.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2913    1.3934   -1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4748    0.7554   -1.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2156    2.2832   -1.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8733    1.1939    1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1193    2.7119    0.3873 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
  5  7  1  0
  5  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17  2  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
  6 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
M  END


  Mrv0541 05061309162D          

 17 17  0  0  0  0            999 V2000
    3.9111   -0.5213    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2011   -1.7325    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2680    1.7871    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2279    2.1572    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7385   -0.7312    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5404   -0.9251    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1696   -1.3288    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8761    0.4639    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7281    0.3368    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0086    0.7139    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7510    1.1614    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1092   -0.3275    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3677   -1.1349    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1347   -0.3435    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5424    1.3945    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2270   -0.7769    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6713   -0.1672    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  5  1  0  0  0  0
  7  5  1  0  0  0  0
 10  8  1  0  0  0  0
 11  9  2  0  0  0  0
 12  1  1  0  0  0  0
 12  6  1  0  0  0  0
 12  8  2  0  0  0  0
 13  2  1  0  0  0  0
 13  7  2  0  0  0  0
 14  9  1  0  0  0  0
 14 13  1  0  0  0  0
 15  3  1  0  0  0  0
 15  4  1  0  0  0  0
 15 10  1  0  0  0  0
 15 11  1  0  0  0  0
 17 14  1  0  0  0  0
 17 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036668

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C1=C\CC(C)(C)\C=C\C(OO)\C(C)=C/CC1

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-12-6-5-7-13(2)14(17-16)9-11-15(3,4)10-8-12/h7-9,11,14,16H,5-6,10H2,1-4H3/b11-9+,12-8-,13-7-

> <INCHI_KEY>
MMMUNNUIKCPGAL-RTTFEGKLSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.3499

> <EXACT_MASS>
236.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
27.525008874527494

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z,6Z,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-triene-1-peroxol

> <ALOGPS_LOGP>
5.17

> <JCHEM_LOGP>
4.252710875

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
11.692989254880311

> <JCHEM_PKA_STRONGEST_BASIC>
-4.245286499915367

> <JCHEM_POLAR_SURFACE_AREA>
29.46

> <JCHEM_REFRACTIVITY>
74.26020000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.07e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z,6Z,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-triene-1-peroxol

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036668
     RDKit          3D
Humulene-8-hydroperoxide
 41 41  0  0  0  0  0  0  0  0999 V2000
   -1.1189    3.5553    1.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8761    2.2402    0.3537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696    1.6576   -0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403    0.4450   -0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7024   -0.8866   -0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0035   -1.7871   -0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4758   -0.9283    1.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7332   -1.6262   -1.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483   -1.7985   -0.9596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4971   -1.3072    0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1967   -2.5070    0.4216 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171   -2.8054    1.6784 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5274   -0.3900   -0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9800   -0.8275   -0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4001    0.7967   -0.9090 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0122    1.3246   -1.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4491    1.7659    0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1449    4.0628    1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5109    3.2005    2.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8650    4.1564    0.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9548    2.1753    0.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6881    0.4333   -1.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1760    0.3407   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7660   -2.7839    0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1930   -1.8533   -1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8236   -1.2685    0.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063   -0.9110    1.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9677   -0.0994    1.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1070   -1.9456    1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2258   -2.1154   -1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0626   -2.4043   -1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0232   -1.0594    1.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953   -2.3837    2.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228    0.0216    0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0588   -1.5546    0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2838   -1.2709   -1.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2913    1.3934   -1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4748    0.7554   -1.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2156    2.2832   -1.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8733    1.1939    1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1193    2.7119    0.3873 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
  5  7  1  0
  5  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17  2  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
  6 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  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       7.301  -0.973   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -0.375  -3.234   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.234   3.336   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.292   4.027   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       3.245  -1.365   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       4.742  -1.727   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       2.183  -2.480   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.369   0.866   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.359   0.629   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       3.749   1.333   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       1.402   2.168   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.804  -0.611   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.686  -2.118   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.251  -0.641   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.879   2.603   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0      -2.290  -1.450   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0      -1.253  -0.312   0.000  0.00  0.00           O+0
CONECT    1   12                                                            
CONECT    2   13                                                            
CONECT    3   15                                                            
CONECT    4   15                                                            
CONECT    5    6    7                                                       
CONECT    6    5   12                                                       
CONECT    7    5   13                                                       
CONECT    8   10   12                                                       
CONECT    9   11   14                                                       
CONECT   10    8   15                                                       
CONECT   11    9   15                                                       
CONECT   12    1    6    8                                                  
CONECT   13    2    7   14                                                  
CONECT   14    9   13   17                                                  
CONECT   15    3    4   10   11                                             
CONECT   16   17                                                            
CONECT   17   14   16                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0036668
HETATM    1  C1  UNL     1      -1.119   3.555   1.139  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.876   2.240   0.354  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.970   1.658  -0.046  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.040   0.445  -0.786  1.00  0.00           C  
HETATM    5  C5  UNL     1      -1.702  -0.887  -0.194  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.004  -1.787  -0.268  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.476  -0.928   1.271  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.733  -1.626  -1.048  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.548  -1.799  -0.960  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.497  -1.307   0.044  1.00  0.00           C  
HETATM   11  O1  UNL     1       2.197  -2.507   0.422  1.00  0.00           O  
HETATM   12  O2  UNL     1       2.017  -2.805   1.678  1.00  0.00           O  
HETATM   13  C11 UNL     1       2.527  -0.390  -0.384  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.980  -0.828  -0.215  1.00  0.00           C  
HETATM   15  C13 UNL     1       2.400   0.797  -0.909  1.00  0.00           C  
HETATM   16  C14 UNL     1       1.012   1.325  -1.115  1.00  0.00           C  
HETATM   17  C15 UNL     1       0.449   1.766   0.159  1.00  0.00           C  
HETATM   18  H1  UNL     1      -0.145   4.063   1.284  1.00  0.00           H  
HETATM   19  H2  UNL     1      -1.511   3.201   2.110  1.00  0.00           H  
HETATM   20  H3  UNL     1      -1.865   4.156   0.622  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.955   2.175   0.231  1.00  0.00           H  
HETATM   22  H5  UNL     1      -1.688   0.433  -1.847  1.00  0.00           H  
HETATM   23  H6  UNL     1      -3.176   0.341  -1.053  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.766  -2.784   0.101  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.193  -1.853  -1.355  1.00  0.00           H  
HETATM   26  H9  UNL     1      -3.824  -1.268   0.223  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.506  -0.911   1.775  1.00  0.00           H  
HETATM   28  H11 UNL     1      -0.968  -0.099   1.746  1.00  0.00           H  
HETATM   29  H12 UNL     1      -1.107  -1.946   1.528  1.00  0.00           H  
HETATM   30  H13 UNL     1      -1.226  -2.115  -1.943  1.00  0.00           H  
HETATM   31  H14 UNL     1       1.063  -2.404  -1.752  1.00  0.00           H  
HETATM   32  H15 UNL     1       1.023  -1.059   1.017  1.00  0.00           H  
HETATM   33  H16 UNL     1       1.195  -2.384   2.032  1.00  0.00           H  
HETATM   34  H17 UNL     1       4.623   0.022   0.011  1.00  0.00           H  
HETATM   35  H18 UNL     1       4.059  -1.555   0.618  1.00  0.00           H  
HETATM   36  H19 UNL     1       4.284  -1.271  -1.183  1.00  0.00           H  
HETATM   37  H20 UNL     1       3.291   1.393  -1.191  1.00  0.00           H  
HETATM   38  H21 UNL     1       0.475   0.755  -1.840  1.00  0.00           H  
HETATM   39  H22 UNL     1       1.216   2.283  -1.724  1.00  0.00           H  
HETATM   40  H23 UNL     1       0.873   1.194   1.061  1.00  0.00           H  
HETATM   41  H24 UNL     1       1.119   2.712   0.387  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   17
CONECT    3    4   21
CONECT    4    5   22   23
CONECT    5    6    7    8
CONECT    6   24   25   26
CONECT    7   27   28   29
CONECT    8    9    9   30
CONECT    9   10   31
CONECT   10   11   13   32
CONECT   11   12
CONECT   12   33
CONECT   13   14   15   15
CONECT   14   34   35   36
CONECT   15   16   37
CONECT   16   17   38   39
CONECT   17   40   41
END

HMDB0036668
     RDKit          3D
Humulene-8-hydroperoxide
 41 41  0  0  0  0  0  0  0  0999 V2000
   -1.1189    3.5553    1.1393 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8761    2.2402    0.3537 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9696    1.6576   -0.0458 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0403    0.4450   -0.7864 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7024   -0.8866   -0.1938 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0035   -1.7871   -0.2681 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4758   -0.9283    1.2713 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7332   -1.6262   -1.0480 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5483   -1.7985   -0.9596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4971   -1.3072    0.0443 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1967   -2.5070    0.4216 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0171   -2.8054    1.6784 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5274   -0.3900   -0.3844 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9800   -0.8275   -0.2155 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4001    0.7967   -0.9090 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0122    1.3246   -1.1148 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4491    1.7659    0.1591 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1449    4.0628    1.2839 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5109    3.2005    2.1101 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8650    4.1564    0.6216 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9548    2.1753    0.2311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6881    0.4333   -1.8473 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1760    0.3407   -1.0530 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7660   -2.7839    0.1008 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1930   -1.8533   -1.3549 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8236   -1.2685    0.2232 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5063   -0.9110    1.7746 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9677   -0.0994    1.7460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1070   -1.9456    1.5283 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2258   -2.1154   -1.9432 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0626   -2.4043   -1.7523 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0232   -1.0594    1.0171 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1953   -2.3837    2.0318 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6228    0.0216    0.0110 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0588   -1.5546    0.6185 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2838   -1.2709   -1.1825 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2913    1.3934   -1.1912 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4748    0.7554   -1.8404 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2156    2.2832   -1.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8733    1.1939    1.0607 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1193    2.7119    0.3873 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
  5  7  1  0
  5  8  1  0
  8  9  2  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 10 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16 17  1  0
 17  2  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
  6 24  1  0
  6 25  1  0
  6 26  1  0
  7 27  1  0
  7 28  1  0
  7 29  1  0
  8 30  1  0
  9 31  1  0
 10 32  1  0
 12 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 17 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8-Hydroperoxy-2,6,9-humulatriene	HMDB

Chemical Formula

C₁₅H₂₄O₂

Average Molecular Weight

236.3499

Monoisotopic Molecular Weight

236.177630012

IUPAC Name

(2Z,6Z,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-triene-1-peroxol

Traditional Name

(2Z,6Z,10E)-2,6,9,9-tetramethylcycloundeca-2,6,10-triene-1-peroxol

CAS Registry Number

228565-88-6

SMILES

C\C1=C\CC(C)(C)\C=C\C(OO)\C(C)=C/CC1

InChI Identifier

InChI=1S/C15H24O2/c1-12-6-5-7-13(2)14(17-16)9-11-15(3,4)10-8-12/h7-9,11,14,16H,5-6,10H2,1-4H3/b11-9+,12-8-,13-7-

InChI Key

MMMUNNUIKCPGAL-RTTFEGKLSA-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

Humulane sesquiterpenoid
Sesquiterpenoid
Allylic hydroperoxide
Hydroperoxide
Alkyl hydroperoxide
Peroxol
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036668)

Source

Endogenous

Endogenous (HMDB: HMDB0036668)

Animal

Animal (HMDB: HMDB0036668)

Exogenous

Food

Food (HMDB: HMDB0036668)

Exogenous (HMDB: HMDB0036668)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0036668)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0036668)

Lipid metabolism pathway (HMDB: HMDB0036668)

Cellular process

Cell signaling (HMDB: HMDB0036668)

Biochemical process

Lipid transport (HMDB: HMDB0036668)

Role

Biological role

Energy source (HMDB: HMDB0036668)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036668)

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	0.44 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	0.081 g/L	ALOGPS
logP	5.17	ALOGPS
logP	4.25	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	11.69	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.46 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	74.26 m³·mol⁻¹	ChemAxon
Polarizability	27.53 Å³	ChemAxon
Number of Rings	1	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]+	160.176	31661259
DarkChem	[M-H]-	156.476	31661259
DeepCCS	[M+H]+	164.977	30932474
DeepCCS	[M-H]-	162.619	30932474
DeepCCS	[M-2H]-	195.505	30932474
DeepCCS	[M+Na]+	171.07	30932474
AllCCS	[M+H]+	156.2	32859911
AllCCS	[M+H-H2O]+	152.3	32859911
AllCCS	[M+NH4]+	159.8	32859911
AllCCS	[M+Na]+	160.8	32859911
AllCCS	[M-H]-	161.7	32859911
AllCCS	[M+Na-2H]-	162.1	32859911
AllCCS	[M+HCOO]-	162.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	6.72 minutes	32390414
Predicted by Siyang on May 30, 2022	17.9729 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.06 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2636.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	343.0 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	178.8 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	199.5 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	96.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	511.1 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	439.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	70.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1401.0 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	543.1 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	941.8 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	462.7 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	366.9 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	283.7 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	479.1 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.0 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Humulene-8-hydroperoxide	C\C1=C\CC(C)(C)\C=C\C(OO)\C(C)=C/CC1	2444.1	Standard polar	33892256
Humulene-8-hydroperoxide	C\C1=C\CC(C)(C)\C=C\C(OO)\C(C)=C/CC1	1749.9	Standard non polar	33892256
Humulene-8-hydroperoxide	C\C1=C\CC(C)(C)\C=C\C(OO)\C(C)=C/CC1	1750.1	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 - Humulene-8-hydroperoxide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fe0-1290000000-7d06d5309ade06f5af07	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Humulene-8-hydroperoxide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Humulene-8-hydroperoxide 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 - Humulene-8-hydroperoxide 10V, Positive-QTOF	splash10-000i-0190000000-4954bdb749c927fe8453	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Humulene-8-hydroperoxide 20V, Positive-QTOF	splash10-0f79-3890000000-bd7e50ecd85012d6a2b6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Humulene-8-hydroperoxide 40V, Positive-QTOF	splash10-0uxr-9510000000-1257cf8a9372bb25bbac	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Humulene-8-hydroperoxide 10V, Negative-QTOF	splash10-000i-0090000000-7f2f9e06bb75b7af2f22	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Humulene-8-hydroperoxide 20V, Negative-QTOF	splash10-00kr-0190000000-339151261c0e3860b7c8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Humulene-8-hydroperoxide 40V, Negative-QTOF	splash10-02t9-3940000000-e01d9eab64362cea56a7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Humulene-8-hydroperoxide 10V, Negative-QTOF	splash10-0udr-0090000000-b01dac4c87eb67f0b287	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Humulene-8-hydroperoxide 20V, Negative-QTOF	splash10-0uy0-0090000000-cc02f050f251d638802a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Humulene-8-hydroperoxide 40V, Negative-QTOF	splash10-0uxr-0090000000-8292fd7f905a1e178b2f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Humulene-8-hydroperoxide 10V, Positive-QTOF	splash10-0udi-0090000000-356f4c47dc67101a8626	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Humulene-8-hydroperoxide 20V, Positive-QTOF	splash10-0udi-0090000000-8620a29e035d055304c3	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Humulene-8-hydroperoxide 40V, Positive-QTOF	splash10-0udr-0790000000-f8bb2c85cfd39df68fe4	2021-09-23	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

FDB015596

KNApSAcK ID

Not Available

Chemspider ID

35014189

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

131752029

PDB ID

Not Available

ChEBI ID

173716

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1856331

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 Humulene-8-hydroperoxide (HMDB0036668)

MOL for HMDB0036668 (Humulene-8-hydroperoxide)

3D MOL for HMDB0036668 (Humulene-8-hydroperoxide)

3D SDF for HMDB0036668 (Humulene-8-hydroperoxide)

3D-SDF for HMDB0036668 (Humulene-8-hydroperoxide)

PDB for HMDB0036668 (Humulene-8-hydroperoxide)

3D PDB for HMDB0036668 (Humulene-8-hydroperoxide)

SMILES for HMDB0036668 (Humulene-8-hydroperoxide)

INCHI for HMDB0036668 (Humulene-8-hydroperoxide)

Structure for HMDB0036668 (Humulene-8-hydroperoxide)

3D Structure for HMDB0036668 (Humulene-8-hydroperoxide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra