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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:51:10 UTC

Update Date

2022-03-07 02:53:26 UTC

HMDB ID

HMDB0032681

Secondary Accession Numbers

HMDB32681

Metabolite Identification

Common Name

10alpha-4,5-Seco-11-eudesmene-4,5-dione

Description

10alpha-4,5-Seco-11-eudesmene-4,5-dione belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes. Based on a literature review a small amount of articles have been published on 10alpha-4,5-Seco-11-eudesmene-4,5-dione.

Structure

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

HMDB0032681
     RDKit          3D
10alpha-4,5-Seco-11-eudesmene-4,5-dione
 41 41  0  0  0  0  0  0  0  0999 V2000
    5.1567   -0.5065   -0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8346   -0.5251   -0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455   -1.5513   -1.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9984    0.4351    0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3217    1.4498   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9935    1.0742   -0.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003    0.7152    0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1972    1.9306    1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2536    0.3293   -0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4084   -0.0647    0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5733   -0.4105   -0.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7716   -0.8166    0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0174   -1.1948   -0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6784   -0.8222    1.4383 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6856   -0.3946    0.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0844   -1.4358    1.1065 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0703   -0.2927    1.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6151    0.2273    0.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7998   -1.1765   -0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1770   -1.7385   -0.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3770   -1.2235   -2.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8415   -2.4827   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083    0.9915    1.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1826    2.3975    0.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9837    1.7132   -1.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    0.2437   -1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549    1.9562   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7128    2.1414    1.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4665    2.7683    0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0157    1.7640    1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5324    1.2132   -1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9837   -0.4639   -1.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1702   -1.0105    0.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6996    0.6591    1.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8117    0.4111   -1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3025   -1.2880   -1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8842   -0.7347    0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9725   -0.8477   -1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0967   -2.3057   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0251    0.1720    2.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4972   -1.3059    1.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  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
 12 14  2  0
  7 15  1  0
 15 16  2  0
 15 17  1  0
 17  4  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 17 40  1  0
 17 41  1  0
M  END

  Mrv0541 02241207482D          

 17 17  0  0  0  0            999 V2000
   -1.4259    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4259   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7123   -0.6188    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7123    1.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7136   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4259   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4259    0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7136    1.0299    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1411   -1.4439    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8562   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    1.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1411   -0.6188    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8562   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1411   -1.4439    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  6  1  0  0  0  0
  2 11  1  0  0  0  0
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  4  7  1  0  0  0  0
  5  6  1  0  0  0  0
  5 10  1  0  0  0  0
  5 14  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  8 15  1  0  0  0  0
  9 10  1  0  0  0  0
 11 12  2  0  0  0  0
 11 13  1  0  0  0  0
 15 16  1  0  0  0  0
 15 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032681

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=O)CCCC1(C)CCC(CC1=O)C(C)=C

> <INCHI_IDENTIFIER>
InChI=1S/C15H24O2/c1-11(2)13-7-9-15(4,14(17)10-13)8-5-6-12(3)16/h13H,1,5-10H2,2-4H3

> <INCHI_KEY>
FCPUGTGXHMJFQH-UHFFFAOYSA-N

> <FORMULA>
C15H24O2

> <MOLECULAR_WEIGHT>
236.3499

> <EXACT_MASS>
236.177630012

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
28.113116543125763

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-methyl-2-(4-oxopentyl)-5-(prop-1-en-2-yl)cyclohexan-1-one

> <ALOGPS_LOGP>
3.00

> <JCHEM_LOGP>
3.601245644333333

> <ALOGPS_LOGS>
-3.77

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
19.64304187457009

> <JCHEM_PKA_STRONGEST_BASIC>
-7.062372522480789

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
69.8181

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
4.06e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-methyl-2-(4-oxopentyl)-5-(prop-1-en-2-yl)cyclohexan-1-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0032681
     RDKit          3D
10alpha-4,5-Seco-11-eudesmene-4,5-dione
 41 41  0  0  0  0  0  0  0  0999 V2000
    5.1567   -0.5065   -0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8346   -0.5251   -0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455   -1.5513   -1.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9984    0.4351    0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3217    1.4498   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9935    1.0742   -0.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003    0.7152    0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1972    1.9306    1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2536    0.3293   -0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4084   -0.0647    0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5733   -0.4105   -0.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7716   -0.8166    0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0174   -1.1948   -0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6784   -0.8222    1.4383 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6856   -0.3946    0.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0844   -1.4358    1.1065 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0703   -0.2927    1.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6151    0.2273    0.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7998   -1.1765   -0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1770   -1.7385   -0.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3770   -1.2235   -2.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8415   -2.4827   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083    0.9915    1.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1826    2.3975    0.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9837    1.7132   -1.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    0.2437   -1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549    1.9562   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7128    2.1414    1.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4665    2.7683    0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0157    1.7640    1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5324    1.2132   -1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9837   -0.4639   -1.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1702   -1.0105    0.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6996    0.6591    1.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8117    0.4111   -1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3025   -1.2880   -1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8842   -0.7347    0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9725   -0.8477   -1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0967   -2.3057   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0251    0.1720    2.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4972   -1.3059    1.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  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
 12 14  2  0
  7 15  1  0
 15 16  2  0
 15 17  1  0
 17  4  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 17 40  1  0
 17 41  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0      -2.662   1.155   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -2.662  -0.385   0.000  0.00  0.00           C+0
HETATM    3  O   UNK     0      -1.330  -1.155   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0       0.000  -0.385   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       0.000   1.155   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.330   1.922   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       1.332  -1.155   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       2.662  -0.385   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.662   1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.332   1.922   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -3.997  -1.155   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0      -3.997  -2.695   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -5.332  -0.385   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       0.000   2.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.997  -1.155   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       5.332  -0.385   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       3.997  -2.695   0.000  0.00  0.00           C+0
CONECT    1    2    6                                                       
CONECT    2    1   11                                                       
CONECT    3    4                                                            
CONECT    4    3    5    7                                                  
CONECT    5    4    6   10   14                                             
CONECT    6    1    5                                                       
CONECT    7    4    8                                                       
CONECT    8    7    9   15                                                  
CONECT    9    8   10                                                       
CONECT   10    5    9                                                       
CONECT   11    2   12   13                                                  
CONECT   12   11                                                            
CONECT   13   11                                                            
CONECT   14    5                                                            
CONECT   15    8   16   17                                                  
CONECT   16   15                                                            
CONECT   17   15                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0032681
HETATM    1  C1  UNL     1       5.157  -0.507  -0.215  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.835  -0.525  -0.287  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.245  -1.551  -1.187  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.998   0.435   0.496  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.322   1.450  -0.366  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.994   1.074  -0.903  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.000   0.715   0.219  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.197   1.931   1.085  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.254   0.329  -0.484  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.408  -0.065   0.365  1.00  0.00           C  
HETATM   11  C11 UNL     1      -3.573  -0.410  -0.572  1.00  0.00           C  
HETATM   12  C12 UNL     1      -4.772  -0.817   0.220  1.00  0.00           C  
HETATM   13  C13 UNL     1      -6.017  -1.195  -0.474  1.00  0.00           C  
HETATM   14  O1  UNL     1      -4.678  -0.822   1.438  1.00  0.00           O  
HETATM   15  C14 UNL     1       0.686  -0.395   0.931  1.00  0.00           C  
HETATM   16  O2  UNL     1       0.084  -1.436   1.107  1.00  0.00           O  
HETATM   17  C15 UNL     1       2.070  -0.293   1.436  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.615   0.227   0.430  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.800  -1.176  -0.758  1.00  0.00           H  
HETATM   20  H3  UNL     1       2.177  -1.739  -0.997  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.377  -1.223  -2.237  1.00  0.00           H  
HETATM   22  H5  UNL     1       3.842  -2.483  -1.063  1.00  0.00           H  
HETATM   23  H6  UNL     1       3.708   0.991   1.148  1.00  0.00           H  
HETATM   24  H7  UNL     1       2.183   2.397   0.235  1.00  0.00           H  
HETATM   25  H8  UNL     1       2.984   1.713  -1.189  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.970   0.244  -1.601  1.00  0.00           H  
HETATM   27  H10 UNL     1       0.555   1.956  -1.400  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.713   2.141   1.671  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.466   2.768   0.445  1.00  0.00           H  
HETATM   30  H13 UNL     1      -1.016   1.764   1.802  1.00  0.00           H  
HETATM   31  H14 UNL     1      -1.532   1.213  -1.131  1.00  0.00           H  
HETATM   32  H15 UNL     1      -0.984  -0.464  -1.226  1.00  0.00           H  
HETATM   33  H16 UNL     1      -2.170  -1.011   0.889  1.00  0.00           H  
HETATM   34  H17 UNL     1      -2.700   0.659   1.120  1.00  0.00           H  
HETATM   35  H18 UNL     1      -3.812   0.411  -1.254  1.00  0.00           H  
HETATM   36  H19 UNL     1      -3.302  -1.288  -1.194  1.00  0.00           H  
HETATM   37  H20 UNL     1      -6.884  -0.735   0.027  1.00  0.00           H  
HETATM   38  H21 UNL     1      -5.973  -0.848  -1.522  1.00  0.00           H  
HETATM   39  H22 UNL     1      -6.097  -2.306  -0.453  1.00  0.00           H  
HETATM   40  H23 UNL     1       2.025   0.172   2.443  1.00  0.00           H  
HETATM   41  H24 UNL     1       2.497  -1.306   1.584  1.00  0.00           H  
CONECT    1    2    2   18   19
CONECT    2    3    4
CONECT    3   20   21   22
CONECT    4    5   17   23
CONECT    5    6   24   25
CONECT    6    7   26   27
CONECT    7    8    9   15
CONECT    8   28   29   30
CONECT    9   10   31   32
CONECT   10   11   33   34
CONECT   11   12   35   36
CONECT   12   13   14   14
CONECT   13   37   38   39
CONECT   15   16   16   17
CONECT   17   40   41
END

HMDB0032681
     RDKit          3D
10alpha-4,5-Seco-11-eudesmene-4,5-dione
 41 41  0  0  0  0  0  0  0  0999 V2000
    5.1567   -0.5065   -0.2146 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8346   -0.5251   -0.2871 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2455   -1.5513   -1.1868 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9984    0.4351    0.4957 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3217    1.4498   -0.3660 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9935    1.0742   -0.9029 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0003    0.7152    0.2195 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1972    1.9306    1.0849 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2536    0.3293   -0.4836 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4084   -0.0647    0.3653 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5733   -0.4105   -0.5718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7716   -0.8166    0.2198 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0174   -1.1948   -0.4741 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6784   -0.8222    1.4383 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6856   -0.3946    0.9306 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0844   -1.4358    1.1065 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0703   -0.2927    1.4363 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6151    0.2273    0.4303 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7998   -1.1765   -0.7579 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1770   -1.7385   -0.9972 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3770   -1.2235   -2.2368 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8415   -2.4827   -1.0625 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7083    0.9915    1.1478 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1826    2.3975    0.2351 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9837    1.7132   -1.1892 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9697    0.2437   -1.6009 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5549    1.9562   -1.3997 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7128    2.1414    1.6707 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4665    2.7683    0.4445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0157    1.7640    1.8016 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5324    1.2132   -1.1311 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9837   -0.4639   -1.2263 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1702   -1.0105    0.8891 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6996    0.6591    1.1196 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8117    0.4111   -1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3025   -1.2880   -1.1938 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8842   -0.7347    0.0271 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9725   -0.8477   -1.5222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0967   -2.3057   -0.4531 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0251    0.1720    2.4434 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4972   -1.3059    1.5842 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  3
  2  3  1  0
  2  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
 12 14  2  0
  7 15  1  0
 15 16  2  0
 15 17  1  0
 17  4  1  0
  1 18  1  0
  1 19  1  0
  3 20  1  0
  3 21  1  0
  3 22  1  0
  4 23  1  0
  5 24  1  0
  5 25  1  0
  6 26  1  0
  6 27  1  0
  8 28  1  0
  8 29  1  0
  8 30  1  0
  9 31  1  0
  9 32  1  0
 10 33  1  0
 10 34  1  0
 11 35  1  0
 11 36  1  0
 13 37  1  0
 13 38  1  0
 13 39  1  0
 17 40  1  0
 17 41  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
10a-4,5-Seco-11-eudesmene-4,5-dione	Generator
10Α-4,5-seco-11-eudesmene-4,5-dione	Generator

Chemical Formula

C₁₅H₂₄O₂

Average Molecular Weight

236.3499

Monoisotopic Molecular Weight

236.177630012

IUPAC Name

2-methyl-2-(4-oxopentyl)-5-(prop-1-en-2-yl)cyclohexan-1-one

Traditional Name

2-methyl-2-(4-oxopentyl)-5-(prop-1-en-2-yl)cyclohexan-1-one

CAS Registry Number

210106-14-2

SMILES

CC(=O)CCCC1(C)CCC(CC1=O)C(C)=C

InChI Identifier

InChI=1S/C15H24O2/c1-11(2)13-7-9-15(4,14(17)10-13)8-5-6-12(3)16/h13H,1,5-10H2,2-4H3

InChI Key

FCPUGTGXHMJFQH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as menthane monoterpenoids. These are monoterpenoids with a structure based on the o-, m-, or p-menthane backbone. P-menthane consists of the cyclohexane ring with a methyl group and a (2-methyl)-propyl group at the 1 and 4 ring position, respectively. The o- and m- menthanes are much rarer, and presumably arise by alkyl migration of p-menthanes.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Monoterpenoids

Direct Parent

Menthane monoterpenoids

Alternative Parents

Substituents

P-menthane monoterpenoid
Monocyclic monoterpenoid
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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: HMDB0032681)

Source

Exogenous

Food

Food (HMDB: HMDB0032681)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Exogenous (HMDB: HMDB0032681)

Endogenous

Plant

Plant (HMDB: HMDB0032681)

Animal

Animal (HMDB: HMDB0032681)

Endogenous (HMDB: HMDB0032681)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0032681)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0032681)

Lipid metabolism pathway (HMDB: HMDB0032681)

Cellular process

Cell signaling (HMDB: HMDB0032681)

Biochemical process

Lipid transport (HMDB: HMDB0032681)

Role

Biological role

Energy source (HMDB: HMDB0032681)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032681)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.041 g/L	ALOGPS
logP	3	ALOGPS
logP	3.6	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	19.64	ChemAxon
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	34.14 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	69.82 m³·mol⁻¹	ChemAxon
Polarizability	28.11 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]+	157.642	31661259
DarkChem	[M-H]-	154.222	31661259
DeepCCS	[M+H]+	158.798	30932474
DeepCCS	[M-H]-	156.44	30932474
DeepCCS	[M-2H]-	190.129	30932474
DeepCCS	[M+Na]+	165.069	30932474
AllCCS	[M+H]+	159.1	32859911
AllCCS	[M+H-H2O]+	155.5	32859911
AllCCS	[M+NH4]+	162.4	32859911
AllCCS	[M+Na]+	163.4	32859911
AllCCS	[M-H]-	164.2	32859911
AllCCS	[M+Na-2H]-	165.0	32859911
AllCCS	[M+HCOO]-	166.1	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
10alpha-4,5-Seco-11-eudesmene-4,5-dione	CC(=O)CCCC1(C)CCC(CC1=O)C(C)=C	2321.2	Standard polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione	CC(=O)CCCC1(C)CCC(CC1=O)C(C)=C	1696.9	Standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione	CC(=O)CCCC1(C)CCC(CC1=O)C(C)=C	1814.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TMS,isomer #1	C=C(C)C1CCC(C)(CCC=C(C)O[Si](C)(C)C)C(=O)C1	1922.4	Semi standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TMS,isomer #1	C=C(C)C1CCC(C)(CCC=C(C)O[Si](C)(C)C)C(=O)C1	1883.8	Standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TMS,isomer #2	C=C(C)C1C=C(O[Si](C)(C)C)C(C)(CCCC(C)=O)CC1	1818.2	Semi standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TMS,isomer #2	C=C(C)C1C=C(O[Si](C)(C)C)C(C)(CCCC(C)=O)CC1	1798.9	Standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TMS,isomer #3	C=C(CCCC1(C)CCC(C(=C)C)CC1=O)O[Si](C)(C)C	1881.0	Semi standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TMS,isomer #3	C=C(CCCC1(C)CCC(C(=C)C)CC1=O)O[Si](C)(C)C	1901.4	Standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,2TMS,isomer #1	C=C(C)C1C=C(O[Si](C)(C)C)C(C)(CCC=C(C)O[Si](C)(C)C)CC1	1916.5	Semi standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,2TMS,isomer #1	C=C(C)C1C=C(O[Si](C)(C)C)C(C)(CCC=C(C)O[Si](C)(C)C)CC1	1914.5	Standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,2TMS,isomer #2	C=C(CCCC1(C)CCC(C(=C)C)C=C1O[Si](C)(C)C)O[Si](C)(C)C	1872.9	Semi standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,2TMS,isomer #2	C=C(CCCC1(C)CCC(C(=C)C)C=C1O[Si](C)(C)C)O[Si](C)(C)C	1954.5	Standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TBDMS,isomer #1	C=C(C)C1CCC(C)(CCC=C(C)O[Si](C)(C)C(C)(C)C)C(=O)C1	2177.7	Semi standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TBDMS,isomer #1	C=C(C)C1CCC(C)(CCC=C(C)O[Si](C)(C)C(C)(C)C)C(=O)C1	2115.9	Standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TBDMS,isomer #2	C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)(CCCC(C)=O)CC1	2062.3	Semi standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TBDMS,isomer #2	C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)(CCCC(C)=O)CC1	1943.3	Standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TBDMS,isomer #3	C=C(CCCC1(C)CCC(C(=C)C)CC1=O)O[Si](C)(C)C(C)(C)C	2132.3	Semi standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,1TBDMS,isomer #3	C=C(CCCC1(C)CCC(C(=C)C)CC1=O)O[Si](C)(C)C(C)(C)C	2128.8	Standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,2TBDMS,isomer #1	C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)(CCC=C(C)O[Si](C)(C)C(C)(C)C)CC1	2426.9	Semi standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,2TBDMS,isomer #1	C=C(C)C1C=C(O[Si](C)(C)C(C)(C)C)C(C)(CCC=C(C)O[Si](C)(C)C(C)(C)C)CC1	2239.6	Standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,2TBDMS,isomer #2	C=C(CCCC1(C)CCC(C(=C)C)C=C1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2358.9	Semi standard non polar	33892256
10alpha-4,5-Seco-11-eudesmene-4,5-dione,2TBDMS,isomer #2	C=C(CCCC1(C)CCC(C(=C)C)C=C1O[Si](C)(C)C(C)(C)C)O[Si](C)(C)C(C)(C)C	2252.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9410000000-d965b99e47f46bd79d77	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 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 - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 10V, Positive-QTOF	splash10-00kr-1290000000-6c31e3291e760794d6e7	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 20V, Positive-QTOF	splash10-014i-6940000000-dcca84c66429ebb47c1c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 40V, Positive-QTOF	splash10-0fr7-9100000000-94889a337c289272bfde	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 10V, Negative-QTOF	splash10-000i-0090000000-ac11b5bf352850cba2c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 20V, Negative-QTOF	splash10-000i-2290000000-3a314be6ddd7bfeb4723	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 40V, Negative-QTOF	splash10-0aor-8920000000-c298e4b02ac636d4f290	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 10V, Positive-QTOF	splash10-014r-0890000000-5a310ebb42a7a531bfc3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 20V, Positive-QTOF	splash10-00kr-5930000000-50205d0d53d6441907fe	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 40V, Positive-QTOF	splash10-052f-9800000000-9aaf2694ce0e54dcda8b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 10V, Negative-QTOF	splash10-000i-0090000000-c0031dc201eac6b6350a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 20V, Negative-QTOF	splash10-0f7a-1980000000-3c747b90e87c3742cbf6	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10alpha-4,5-Seco-11-eudesmene-4,5-dione 40V, Negative-QTOF	splash10-0002-1900000000-3b039498ed7b890a14a7	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

FDB010637

KNApSAcK ID

Not Available

Chemspider ID

35013466

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

85204671

PDB ID

Not Available

ChEBI ID

173704

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

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 10alpha-4,5-Seco-11-eudesmene-4,5-dione (HMDB0032681)

MOL for HMDB0032681 (10alpha-4,5-Seco-11-eudesmene-4,5-dione)

3D MOL for HMDB0032681 (10alpha-4,5-Seco-11-eudesmene-4,5-dione)

3D SDF for HMDB0032681 (10alpha-4,5-Seco-11-eudesmene-4,5-dione)

3D-SDF for HMDB0032681 (10alpha-4,5-Seco-11-eudesmene-4,5-dione)

PDB for HMDB0032681 (10alpha-4,5-Seco-11-eudesmene-4,5-dione)

3D PDB for HMDB0032681 (10alpha-4,5-Seco-11-eudesmene-4,5-dione)

SMILES for HMDB0032681 (10alpha-4,5-Seco-11-eudesmene-4,5-dione)

INCHI for HMDB0032681 (10alpha-4,5-Seco-11-eudesmene-4,5-dione)

Structure for HMDB0032681 (10alpha-4,5-Seco-11-eudesmene-4,5-dione)

3D Structure for HMDB0032681 (10alpha-4,5-Seco-11-eudesmene-4,5-dione)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra