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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:18:14 UTC

Update Date

2022-03-07 02:55:10 UTC

HMDB ID

HMDB0037061

Secondary Accession Numbers

HMDB37061

Metabolite Identification

Common Name

(+)-4,11-Eudesmadien-3-one

Description

(+)-4,11-Eudesmadien-3-one belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton. Based on a literature review a small amount of articles have been published on (+)-4,11-Eudesmadien-3-one.

Structure

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

HMDB0037061
     RDKit          3D
(+)-4,11-Eudesmadien-3-one
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.2631   -1.2138   -0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8968   -0.0411   -0.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7789    1.1316   -0.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6825    0.1299    0.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505   -1.1860    1.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1731   -1.7082    0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748   -0.8284    0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5805   -1.0023    1.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1132   -1.4080   -0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2968   -0.4954   -0.8036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9839    0.9270   -0.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9339    1.7365   -0.3912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6290    1.3982   -0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2454    2.8083   -0.7650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6903    0.5384   -0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771    1.0323    0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1968   -1.2557   -1.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7172   -2.1368   -0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2272    2.0834   -0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125    1.1087    0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0646    0.9791   -1.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0047    0.6506    1.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5697   -1.1039    2.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8849   -1.9731    1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5329   -1.4105   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0492   -2.7721    0.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2569   -2.0032    2.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7090   -1.0595    1.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2293   -0.1869    2.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6283   -1.6910   -1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703   -2.3527   -0.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6318   -0.5602   -1.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1533   -0.8001   -0.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1157    3.3293   -1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4228    2.7799   -1.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9307    3.2853    0.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6239    2.0022    0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9888    1.2684   -0.9835 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  2  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16  4  1  0
 15  7  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 16 38  1  0
M  END


  Mrv0541 05061309322D          

 16 17  0  0  0  0            999 V2000
    0.0000    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1434   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7145   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724   -0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4289    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    0.0000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    0.8250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013   -0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  5  1  0  0  0  0
  8  6  1  0  0  0  0
 10  1  2  0  0  0  0
 10  2  1  0  0  0  0
 11  3  1  0  0  0  0
 12  5  1  0  0  0  0
 12  9  1  0  0  0  0
 12 10  1  0  0  0  0
 13  9  1  0  0  0  0
 13 11  2  0  0  0  0
 14  6  1  0  0  0  0
 14 11  1  0  0  0  0
 15  4  1  0  0  0  0
 15  7  1  0  0  0  0
 15  8  1  0  0  0  0
 15 13  1  0  0  0  0
 16 14  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037061

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(=C)C1CCC2(C)CCC(=O)C(C)=C2C1

> <INCHI_IDENTIFIER>
InChI=1S/C15H22O/c1-10(2)12-5-7-15(4)8-6-14(16)11(3)13(15)9-12/h12H,1,5-9H2,2-4H3

> <INCHI_KEY>
KUFXJZXMWHNCEH-UHFFFAOYSA-N

> <FORMULA>
C15H22O

> <MOLECULAR_WEIGHT>
218.3346

> <EXACT_MASS>
218.167065326

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
26.255346364935605

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1,4a-dimethyl-7-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one

> <ALOGPS_LOGP>
3.92

> <JCHEM_LOGP>
3.8083682056666674

> <ALOGPS_LOGS>
-3.41

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-4.788972738672884

> <JCHEM_POLAR_SURFACE_AREA>
17.07

> <JCHEM_REFRACTIVITY>
67.87899999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.41e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0037061
     RDKit          3D
(+)-4,11-Eudesmadien-3-one
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.2631   -1.2138   -0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8968   -0.0411   -0.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7789    1.1316   -0.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6825    0.1299    0.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505   -1.1860    1.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1731   -1.7082    0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748   -0.8284    0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5805   -1.0023    1.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1132   -1.4080   -0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2968   -0.4954   -0.8036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9839    0.9270   -0.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9339    1.7365   -0.3912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6290    1.3982   -0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2454    2.8083   -0.7650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6903    0.5384   -0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771    1.0323    0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1968   -1.2557   -1.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7172   -2.1368   -0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2272    2.0834   -0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125    1.1087    0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0646    0.9791   -1.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0047    0.6506    1.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5697   -1.1039    2.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8849   -1.9731    1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5329   -1.4105   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0492   -2.7721    0.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2569   -2.0032    2.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7090   -1.0595    1.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2293   -0.1869    2.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6283   -1.6910   -1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703   -2.3527   -0.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6318   -0.5602   -1.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1533   -0.8001   -0.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1157    3.3293   -1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4228    2.7799   -1.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9307    3.2853    0.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6239    2.0022    0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9888    1.2684   -0.9835 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  2  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16  4  1  0
 15  7  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 16 38  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       0.000   0.000   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       1.334  -2.310   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       6.668  -2.310   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       5.335   3.080   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       2.667   1.540   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.002   1.540   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.001   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       6.668   2.310   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       4.001  -0.770   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.334  -0.770   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       6.668  -0.770   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       2.667   0.000   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       5.335   0.000   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.002   0.000   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335   1.540   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       9.336  -0.770   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4   15                                                            
CONECT    5    7   12                                                       
CONECT    6    8   14                                                       
CONECT    7    5   15                                                       
CONECT    8    6   15                                                       
CONECT    9   12   13                                                       
CONECT   10    1    2   12                                                  
CONECT   11    3   13   14                                                  
CONECT   12    5    9   10                                                  
CONECT   13    9   11   15                                                  
CONECT   14    6   11   16                                                  
CONECT   15    4    7    8   13                                             
CONECT   16   14                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   34    0
END

COMPND    HMDB0037061
HETATM    1  C1  UNL     1       3.263  -1.214  -0.563  1.00  0.00           C  
HETATM    2  C2  UNL     1       2.897  -0.041  -0.114  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.779   1.132  -0.468  1.00  0.00           C  
HETATM    4  C4  UNL     1       1.682   0.130   0.704  1.00  0.00           C  
HETATM    5  C5  UNL     1       1.151  -1.186   1.138  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.173  -1.708   0.112  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.075  -0.828   0.309  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.581  -1.002   1.728  1.00  0.00           C  
HETATM    9  C9  UNL     1      -2.113  -1.408  -0.624  1.00  0.00           C  
HETATM   10  C10 UNL     1      -3.297  -0.495  -0.804  1.00  0.00           C  
HETATM   11  C11 UNL     1      -2.984   0.927  -0.533  1.00  0.00           C  
HETATM   12  O1  UNL     1      -3.934   1.736  -0.391  1.00  0.00           O  
HETATM   13  C12 UNL     1      -1.629   1.398  -0.429  1.00  0.00           C  
HETATM   14  C13 UNL     1      -1.245   2.808  -0.765  1.00  0.00           C  
HETATM   15  C14 UNL     1      -0.690   0.538  -0.016  1.00  0.00           C  
HETATM   16  C15 UNL     1       0.677   1.032   0.078  1.00  0.00           C  
HETATM   17  H1  UNL     1       4.197  -1.256  -1.170  1.00  0.00           H  
HETATM   18  H2  UNL     1       2.717  -2.137  -0.386  1.00  0.00           H  
HETATM   19  H3  UNL     1       3.227   2.083  -0.393  1.00  0.00           H  
HETATM   20  H4  UNL     1       4.713   1.109   0.126  1.00  0.00           H  
HETATM   21  H5  UNL     1       4.065   0.979  -1.529  1.00  0.00           H  
HETATM   22  H6  UNL     1       2.005   0.651   1.673  1.00  0.00           H  
HETATM   23  H7  UNL     1       0.570  -1.104   2.116  1.00  0.00           H  
HETATM   24  H8  UNL     1       1.885  -1.973   1.351  1.00  0.00           H  
HETATM   25  H9  UNL     1       0.533  -1.411  -0.906  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.049  -2.772   0.215  1.00  0.00           H  
HETATM   27  H11 UNL     1      -1.257  -2.003   2.079  1.00  0.00           H  
HETATM   28  H12 UNL     1      -2.709  -1.060   1.721  1.00  0.00           H  
HETATM   29  H13 UNL     1      -1.229  -0.187   2.378  1.00  0.00           H  
HETATM   30  H14 UNL     1      -1.628  -1.691  -1.580  1.00  0.00           H  
HETATM   31  H15 UNL     1      -2.470  -2.353  -0.161  1.00  0.00           H  
HETATM   32  H16 UNL     1      -3.632  -0.560  -1.871  1.00  0.00           H  
HETATM   33  H17 UNL     1      -4.153  -0.800  -0.173  1.00  0.00           H  
HETATM   34  H18 UNL     1      -2.116   3.329  -1.167  1.00  0.00           H  
HETATM   35  H19 UNL     1      -0.423   2.780  -1.527  1.00  0.00           H  
HETATM   36  H20 UNL     1      -0.931   3.285   0.180  1.00  0.00           H  
HETATM   37  H21 UNL     1       0.624   2.002   0.647  1.00  0.00           H  
HETATM   38  H22 UNL     1       0.989   1.268  -0.983  1.00  0.00           H  
CONECT    1    2    2   17   18
CONECT    2    3    4
CONECT    3   19   20   21
CONECT    4    5   16   22
CONECT    5    6   23   24
CONECT    6    7   25   26
CONECT    7    8    9   15
CONECT    8   27   28   29
CONECT    9   10   30   31
CONECT   10   11   32   33
CONECT   11   12   12   13
CONECT   13   14   15   15
CONECT   14   34   35   36
CONECT   15   16
CONECT   16   37   38
END

HMDB0037061
     RDKit          3D
(+)-4,11-Eudesmadien-3-one
 38 39  0  0  0  0  0  0  0  0999 V2000
    3.2631   -1.2138   -0.5633 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8968   -0.0411   -0.1145 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7789    1.1316   -0.4681 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6825    0.1299    0.7044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1505   -1.1860    1.1384 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1731   -1.7082    0.1122 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0748   -0.8284    0.3090 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5805   -1.0023    1.7283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1132   -1.4080   -0.6244 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2968   -0.4954   -0.8036 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9839    0.9270   -0.5326 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9339    1.7365   -0.3912 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6290    1.3982   -0.4290 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2454    2.8083   -0.7650 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6903    0.5384   -0.0164 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6771    1.0323    0.0776 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1968   -1.2557   -1.1704 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7172   -2.1368   -0.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2272    2.0834   -0.3928 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7125    1.1087    0.1261 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0646    0.9791   -1.5292 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0047    0.6506    1.6726 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5697   -1.1039    2.1161 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8849   -1.9731    1.3511 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5329   -1.4105   -0.9057 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0492   -2.7721    0.2146 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2569   -2.0032    2.0789 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7090   -1.0595    1.7212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2293   -0.1869    2.3784 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6283   -1.6910   -1.5799 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4703   -2.3527   -0.1613 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6318   -0.5602   -1.8715 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1533   -0.8001   -0.1730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1157    3.3293   -1.1670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4228    2.7799   -1.5272 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9307    3.2853    0.1802 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6239    2.0022    0.6470 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9888    1.2684   -0.9835 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  2  0
 11 13  1  0
 13 14  1  0
 13 15  2  0
 15 16  1  0
 16  4  1  0
 15  7  1  0
  1 17  1  0
  1 18  1  0
  3 19  1  0
  3 20  1  0
  3 21  1  0
  4 22  1  0
  5 23  1  0
  5 24  1  0
  6 25  1  0
  6 26  1  0
  8 27  1  0
  8 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 10 32  1  0
 10 33  1  0
 14 34  1  0
 14 35  1  0
 14 36  1  0
 16 37  1  0
 16 38  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+)-alpha-Cyperone	HMDB
(4AS-cis)-4,4a,5,6,7,8-hexahydro-1,4a-dimethyl-7-(1-methylethenyl)-2(3H)-naphthalenone	HMDB
Eudesma-4,11-dien-3-one	HMDB

Chemical Formula

C₁₅H₂₂O

Average Molecular Weight

218.3346

Monoisotopic Molecular Weight

218.167065326

IUPAC Name

1,4a-dimethyl-7-(prop-1-en-2-yl)-2,3,4,4a,5,6,7,8-octahydronaphthalen-2-one

Traditional Name

1,4a-dimethyl-7-(prop-1-en-2-yl)-3,4,5,6,7,8-hexahydronaphthalen-2-one

CAS Registry Number

473-08-5

SMILES

CC(=C)C1CCC2(C)CCC(=O)C(C)=C2C1

InChI Identifier

InChI=1S/C15H22O/c1-10(2)12-5-7-15(4)8-6-14(16)11(3)13(15)9-12/h12H,1,5-9H2,2-4H3

InChI Key

KUFXJZXMWHNCEH-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids. These are sesquiterpenoids with a structure based on the eudesmane skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoids

Alternative Parents

Substituents

Eudesmane, isoeudesmane or cycloeudesmane sesquiterpenoid
Cyclohexenone
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic homopolycyclic compound

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037061)

Source

Endogenous

Endogenous (HMDB: HMDB0037061)

Plant

Plant (HMDB: HMDB0037061)

Animal

Animal (HMDB: HMDB0037061)

Exogenous

Food

Food (HMDB: HMDB0037061)

Vegetable

Root vegetable

Root vegetables (FooDB: FOOD00873)

Exogenous (HMDB: HMDB0037061)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037061)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037061)

Lipid metabolism pathway (HMDB: HMDB0037061)

Cellular process

Cell signaling (HMDB: HMDB0037061)

Biochemical process

Lipid transport (HMDB: HMDB0037061)

Role

Biological role

Energy source (HMDB: HMDB0037061)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037061)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	320.40 °C. @ 760.00 mm Hg (est)	The Good Scents Company Information System
Water Solubility	1.84 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.220 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.084 g/L	ALOGPS
logP	3.92	ALOGPS
logP	3.81	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Basic)	-4.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	17.07 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	67.88 m³·mol⁻¹	ChemAxon
Polarizability	26.26 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
DarkChem	[M+H]+	152.594	31661259
DarkChem	[M-H]-	149.211	31661259
DeepCCS	[M+H]+	153.392	30932474
DeepCCS	[M-H]-	151.034	30932474
DeepCCS	[M-2H]-	184.683	30932474
DeepCCS	[M+Na]+	159.619	30932474
AllCCS	[M+H]+	151.2	32859911
AllCCS	[M+H-H2O]+	147.3	32859911
AllCCS	[M+NH4]+	154.8	32859911
AllCCS	[M+Na]+	155.8	32859911
AllCCS	[M-H]-	159.2	32859911
AllCCS	[M+Na-2H]-	159.6	32859911
AllCCS	[M+HCOO]-	160.1	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.	7.96 minutes	32390414
Predicted by Siyang on May 30, 2022	18.1483 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.32 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2330.3 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	616.5 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	225.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	320.3 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	320.6 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	653.3 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	809.1 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	78.8 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1495.6 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	463.4 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	1455.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	492.2 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	423.1 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	414.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	628.2 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	11.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
(+)-4,11-Eudesmadien-3-one	CC(=C)C1CCC2(C)CCC(=O)C(C)=C2C1	2403.5	Standard polar	33892256
(+)-4,11-Eudesmadien-3-one	CC(=C)C1CCC2(C)CCC(=O)C(C)=C2C1	1737.8	Standard non polar	33892256
(+)-4,11-Eudesmadien-3-one	CC(=C)C1CCC2(C)CCC(=O)C(C)=C2C1	1751.4	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
(+)-4,11-Eudesmadien-3-one,1TMS,isomer #1	C=C(C)C1CCC2(C)CC=C(O[Si](C)(C)C)C(C)=C2C1	1882.8	Semi standard non polar	33892256
(+)-4,11-Eudesmadien-3-one,1TMS,isomer #1	C=C(C)C1CCC2(C)CC=C(O[Si](C)(C)C)C(C)=C2C1	1743.4	Standard non polar	33892256
(+)-4,11-Eudesmadien-3-one,1TBDMS,isomer #1	C=C(C)C1CCC2(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)=C2C1	2103.0	Semi standard non polar	33892256
(+)-4,11-Eudesmadien-3-one,1TBDMS,isomer #1	C=C(C)C1CCC2(C)CC=C(O[Si](C)(C)C(C)(C)C)C(C)=C2C1	1924.3	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - (+)-4,11-Eudesmadien-3-one EI-B (Non-derivatized)	splash10-0006-7910000000-df760ddca07d59ed812c	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - (+)-4,11-Eudesmadien-3-one EI-B (Non-derivatized)	splash10-0006-7910000000-df760ddca07d59ed812c	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-4,11-Eudesmadien-3-one GC-MS (Non-derivatized) - 70eV, Positive	splash10-0udu-1910000000-187a975af82ec4d7f588	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - (+)-4,11-Eudesmadien-3-one 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 - (+)-4,11-Eudesmadien-3-one 10V, Positive-QTOF	splash10-014i-0390000000-1c7b5876e297c2ba58b1	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 20V, Positive-QTOF	splash10-0i29-2930000000-14df3115b7817b42780b	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 40V, Positive-QTOF	splash10-0gbc-9700000000-29ed054963831bb24f02	2016-08-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 10V, Negative-QTOF	splash10-014i-0090000000-a146fe81fc0bf2cb8ef6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 20V, Negative-QTOF	splash10-014i-0190000000-2213f64588ca34fc9160	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 40V, Negative-QTOF	splash10-0udi-2940000000-890ebe75f693b7df7251	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 10V, Positive-QTOF	splash10-014i-0980000000-ef0671ce0f33e777c3a9	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 20V, Positive-QTOF	splash10-00kr-2920000000-8cb8c335175fdafdf9da	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 40V, Positive-QTOF	splash10-014i-9300000000-9eab3be47eb1086d6918	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 10V, Negative-QTOF	splash10-014i-0090000000-868e2fb00a2cfbf6c529	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 20V, Negative-QTOF	splash10-014i-0090000000-868e2fb00a2cfbf6c529	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - (+)-4,11-Eudesmadien-3-one 40V, Negative-QTOF	splash10-014i-0890000000-f634f2c34cc81095a09d	2021-09-22	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

FDB016044

KNApSAcK ID

C00012759

Chemspider ID

240707

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

273568

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1441871

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 (+)-4,11-Eudesmadien-3-one (HMDB0037061)

MOL for HMDB0037061 ((+)-4,11-Eudesmadien-3-one)

3D MOL for HMDB0037061 ((+)-4,11-Eudesmadien-3-one)

3D SDF for HMDB0037061 ((+)-4,11-Eudesmadien-3-one)

3D-SDF for HMDB0037061 ((+)-4,11-Eudesmadien-3-one)

PDB for HMDB0037061 ((+)-4,11-Eudesmadien-3-one)

3D PDB for HMDB0037061 ((+)-4,11-Eudesmadien-3-one)

SMILES for HMDB0037061 ((+)-4,11-Eudesmadien-3-one)

INCHI for HMDB0037061 ((+)-4,11-Eudesmadien-3-one)

Structure for HMDB0037061 ((+)-4,11-Eudesmadien-3-one)

3D Structure for HMDB0037061 ((+)-4,11-Eudesmadien-3-one)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra