Jump To Section:

Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References XML

Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:03:47 UTC

Update Date

2022-03-07 02:55:06 UTC

HMDB ID

HMDB0036881

Secondary Accession Numbers

HMDB36881

Metabolite Identification

Common Name

Germacrone-13-al

Description

Germacrone-13-al belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups. Based on a literature review a small amount of articles have been published on Germacrone-13-al.

Structure

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

HMDB0036881
     RDKit          3D
Germacrone-13-al
 37 37  0  0  0  0  0  0  0  0999 V2000
    0.2516    3.0747   -1.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2695    2.2342   -0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5216    1.8475   -0.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3012    1.0122    0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5428   -0.3891    0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9264   -1.5054    0.9074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7491   -2.5531    1.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5742   -1.7072    1.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1745   -0.7214    0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991   -0.4097    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3966   -1.2101   -0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7661   -0.6758   -0.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0324   -2.5554   -0.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891   -2.9861   -0.7950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8504    1.0357    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0862    1.3821    0.1739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7911    2.0390    0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2963    4.1066   -1.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744    2.9836   -2.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739    2.7583   -1.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0597    2.1780   -1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3381    1.5142    0.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0712    1.2613    1.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3399   -0.4972   -0.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6514   -0.6560    0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2473   -3.5210    1.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9077   -2.1701    2.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7661   -2.6014    1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482   -2.5098    1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3348   -0.6628   -0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1214    0.1689    0.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7545    0.1035   -1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3501   -0.4776    0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244   -1.5384   -1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7656   -3.2513   -1.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3501    3.0135    0.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930    1.8857    1.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 10 15  1  0
 15 16  2  0
 15 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
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 17 36  1  0
 17 37  1  0
M  END


  Mrv0541 01111301172D          

 17 17  0  0  0  0            999 V2000
   -1.5132    0.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2277    0.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2277   -0.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5132   -0.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987   -0.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987    0.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843    0.8819    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0843   -0.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6302   -0.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6302    0.4694    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7987    1.2944    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3447    0.8819    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5132   -1.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3447   -0.7681    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0591   -0.3556    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3447   -1.5931    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6302   -2.0056    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  2  0  0  0  0
  1  6  2  0  0  0  0
  7  6  1  0  0  0  0
  5  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
  7 10  1  0  0  0  0
  6 11  1  0  0  0  0
 10 12  2  0  0  0  0
  4 13  1  0  0  0  0
  9 14  2  0  0  0  0
 14 15  1  0  0  0  0
 14 16  1  0  0  0  0
 16 17  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0036881

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C(C=O)=C1\C\C=C(C)\CCC=C(C)CC1=O

> <INCHI_IDENTIFIER>
InChI=1S/C15H20O2/c1-11-5-4-6-12(2)9-15(17)14(8-7-11)13(3)10-16/h6-7,10H,4-5,8-9H2,1-3H3/b11-7+,12-6-,14-13+

> <INCHI_KEY>
QYFIJPMUVNMVMC-IJHCSQTGSA-N

> <FORMULA>
C15H20O2

> <MOLECULAR_WEIGHT>
232.3181

> <EXACT_MASS>
232.146329884

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
25.893702999083168

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2-[(1E,3E)-4,8-dimethyl-10-oxocyclodeca-3,7-dien-1-ylidene]propanal

> <ALOGPS_LOGP>
3.05

> <JCHEM_LOGP>
3.143728417

> <ALOGPS_LOGS>
-3.44

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.53562171713191

> <JCHEM_PKA_STRONGEST_BASIC>
-6.185957083337586

> <JCHEM_POLAR_SURFACE_AREA>
34.14

> <JCHEM_REFRACTIVITY>
72.57379999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.38e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-[(1E,3E)-4,8-dimethyl-10-oxocyclodeca-3,7-dien-1-ylidene]propanal

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0036881
     RDKit          3D
Germacrone-13-al
 37 37  0  0  0  0  0  0  0  0999 V2000
    0.2516    3.0747   -1.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2695    2.2342   -0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5216    1.8475   -0.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3012    1.0122    0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5428   -0.3891    0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9264   -1.5054    0.9074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7491   -2.5531    1.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5742   -1.7072    1.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1745   -0.7214    0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991   -0.4097    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3966   -1.2101   -0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7661   -0.6758   -0.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0324   -2.5554   -0.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891   -2.9861   -0.7950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8504    1.0357    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0862    1.3821    0.1739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7911    2.0390    0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2963    4.1066   -1.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744    2.9836   -2.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739    2.7583   -1.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0597    2.1780   -1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3381    1.5142    0.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0712    1.2613    1.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3399   -0.4972   -0.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6514   -0.6560    0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2473   -3.5210    1.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9077   -2.1701    2.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7661   -2.6014    1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482   -2.5098    1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3348   -0.6628   -0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1214    0.1689    0.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7545    0.1035   -1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3501   -0.4776    0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244   -1.5384   -1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7656   -3.2513   -1.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3501    3.0135    0.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930    1.8857    1.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 10 15  1  0
 15 16  2  0
 15 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
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 17 36  1  0
 17 37  1  0
M  END

HEADER    PROTEIN                                 11-JAN-13   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   11-JAN-13         0                                  
HETATM    1  C   UNK     0      -2.825   1.646   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -4.158   0.876   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -4.158  -0.664   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.825  -1.434   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -1.491  -0.664   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -1.491   0.876   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -0.157   1.646   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.157  -1.434   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.176  -0.664   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       1.176   0.876   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -1.491   2.416   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       2.510   1.646   0.000  0.00  0.00           O+0
HETATM   13  C   UNK     0      -2.825  -2.974   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.510  -1.434   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       3.844  -0.664   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       2.510  -2.974   0.000  0.00  0.00           C+0
HETATM   17  O   UNK     0       1.176  -3.744   0.000  0.00  0.00           O+0
CONECT    1    2    6                                                       
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5   13                                                  
CONECT    5    4    8                                                       
CONECT    6    1    7   11                                                  
CONECT    7    6   10                                                       
CONECT    8    5    9                                                       
CONECT    9    8   10   14                                                  
CONECT   10    9    7   12                                                  
CONECT   11    6                                                            
CONECT   12   10                                                            
CONECT   13    4                                                            
CONECT   14    9   15   16                                                  
CONECT   15   14                                                            
CONECT   16   14   17                                                       
CONECT   17   16                                                            
MASTER        0    0    0    0    0    0    0    0   17    0   34    0
END

COMPND    HMDB0036881
HETATM    1  C1  UNL     1       0.252   3.075  -1.584  1.00  0.00           C  
HETATM    2  C2  UNL     1      -0.270   2.234  -0.416  1.00  0.00           C  
HETATM    3  C3  UNL     1      -1.522   1.848  -0.485  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.301   1.012   0.513  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.543  -0.389   0.150  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.926  -1.505   0.907  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.749  -2.553   1.644  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.574  -1.707   1.017  1.00  0.00           C  
HETATM    9  C9  UNL     1       0.175  -0.721   0.323  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.499  -0.410   0.005  1.00  0.00           C  
HETATM   11  C11 UNL     1       2.397  -1.210  -0.531  1.00  0.00           C  
HETATM   12  C12 UNL     1       3.766  -0.676  -0.784  1.00  0.00           C  
HETATM   13  C13 UNL     1       2.032  -2.555  -0.925  1.00  0.00           C  
HETATM   14  O1  UNL     1       0.889  -2.986  -0.795  1.00  0.00           O  
HETATM   15  C14 UNL     1       1.850   1.036   0.259  1.00  0.00           C  
HETATM   16  O2  UNL     1       3.086   1.382   0.174  1.00  0.00           O  
HETATM   17  C15 UNL     1       0.791   2.039   0.599  1.00  0.00           C  
HETATM   18  H1  UNL     1       0.296   4.107  -1.178  1.00  0.00           H  
HETATM   19  H2  UNL     1      -0.374   2.984  -2.462  1.00  0.00           H  
HETATM   20  H3  UNL     1       1.274   2.758  -1.863  1.00  0.00           H  
HETATM   21  H4  UNL     1      -2.060   2.178  -1.391  1.00  0.00           H  
HETATM   22  H5  UNL     1      -3.338   1.514   0.465  1.00  0.00           H  
HETATM   23  H6  UNL     1      -2.071   1.261   1.561  1.00  0.00           H  
HETATM   24  H7  UNL     1      -2.340  -0.497  -0.966  1.00  0.00           H  
HETATM   25  H8  UNL     1      -3.651  -0.656   0.145  1.00  0.00           H  
HETATM   26  H9  UNL     1      -2.247  -3.521   1.644  1.00  0.00           H  
HETATM   27  H10 UNL     1      -2.908  -2.170   2.667  1.00  0.00           H  
HETATM   28  H11 UNL     1      -3.766  -2.601   1.164  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.148  -2.510   1.580  1.00  0.00           H  
HETATM   30  H13 UNL     1      -0.335  -0.663  -0.694  1.00  0.00           H  
HETATM   31  H14 UNL     1      -0.121   0.169   0.998  1.00  0.00           H  
HETATM   32  H15 UNL     1       3.755   0.104  -1.557  1.00  0.00           H  
HETATM   33  H16 UNL     1       4.350  -0.478   0.111  1.00  0.00           H  
HETATM   34  H17 UNL     1       4.324  -1.538  -1.287  1.00  0.00           H  
HETATM   35  H18 UNL     1       2.766  -3.251  -1.358  1.00  0.00           H  
HETATM   36  H19 UNL     1       1.350   3.014   0.710  1.00  0.00           H  
HETATM   37  H20 UNL     1       0.393   1.886   1.639  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   24   25
CONECT    6    7    8    8
CONECT    7   26   27   28
CONECT    8    9   29
CONECT    9   10   30   31
CONECT   10   11   11   15
CONECT   11   12   13
CONECT   12   32   33   34
CONECT   13   14   14   35
CONECT   15   16   16   17
CONECT   17   36   37
END

HMDB0036881
     RDKit          3D
Germacrone-13-al
 37 37  0  0  0  0  0  0  0  0999 V2000
    0.2516    3.0747   -1.5837 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2695    2.2342   -0.4164 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5216    1.8475   -0.4848 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3012    1.0122    0.5131 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5428   -0.3891    0.1504 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9264   -1.5054    0.9074 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7491   -2.5531    1.6442 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5742   -1.7072    1.0174 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1745   -0.7214    0.3230 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4991   -0.4097    0.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3966   -1.2101   -0.5314 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7661   -0.6758   -0.7844 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.0324   -2.5554   -0.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8891   -2.9861   -0.7950 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8504    1.0357    0.2586 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0862    1.3821    0.1739 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.7911    2.0390    0.5988 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2963    4.1066   -1.1775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3744    2.9836   -2.4623 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2739    2.7583   -1.8627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0597    2.1780   -1.3910 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3381    1.5142    0.4648 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0712    1.2613    1.5615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3399   -0.4972   -0.9663 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6514   -0.6560    0.1453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2473   -3.5210    1.6437 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9077   -2.1701    2.6670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7661   -2.6014    1.1638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1482   -2.5098    1.5800 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3348   -0.6628   -0.6943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1214    0.1689    0.9980 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7545    0.1035   -1.5568 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3501   -0.4776    0.1111 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3244   -1.5384   -1.2873 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7656   -3.2513   -1.3575 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3501    3.0135    0.7101 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3930    1.8857    1.6394 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 11 13  1  0
 13 14  2  0
 10 15  1  0
 15 16  2  0
 15 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
  5 24  1  0
  5 25  1  0
  7 26  1  0
  7 27  1  0
  7 28  1  0
  8 29  1  0
  9 30  1  0
  9 31  1  0
 12 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 17 36  1  0
 17 37  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(e,e,e)-2-(4,8-Dimethyl-10-oxo-3,7-cyclodecadien-1-ylidene)-propanal	HMDB

Chemical Formula

C₁₅H₂₀O₂

Average Molecular Weight

232.3181

Monoisotopic Molecular Weight

232.146329884

IUPAC Name

2-[(1E,3E)-4,8-dimethyl-10-oxocyclodeca-3,7-dien-1-ylidene]propanal

Traditional Name

2-[(1E,3E)-4,8-dimethyl-10-oxocyclodeca-3,7-dien-1-ylidene]propanal

CAS Registry Number

129673-85-4

SMILES

C\C(C=O)=C1\C\C=C(C)\CCC=C(C)CC1=O

InChI Identifier

InChI=1S/C15H20O2/c1-11-5-4-6-12(2)9-15(17)14(8-7-11)13(3)10-16/h6-7,10H,4-5,8-9H2,1-3H3/b11-7+,12-6-,14-13+

InChI Key

QYFIJPMUVNMVMC-IJHCSQTGSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as germacrane sesquiterpenoids. These are sesquiterpenoids having the germacrane skeleton, with a structure characterized by a cyclodecane ring substituted with an isopropyl and two methyl groups.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Prenol lipids

Sub Class

Sesquiterpenoids

Direct Parent

Germacrane sesquiterpenoids

Alternative Parents

Substituents

Germacrane sesquiterpenoid
Enal
Alpha,beta-unsaturated aldehyde
Cyclic ketone
Ketone
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aldehyde
Aliphatic homomonocyclic compound

Molecular Framework

Aliphatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0036881)
Cell membrane (HMDB: HMDB0036881)

Cellular substructure

Extracellular (HMDB: HMDB0036881)
Membrane (HMDB: HMDB0036881)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0036881)

Source

Endogenous

Endogenous (HMDB: HMDB0036881)

Plant

Plant (HMDB: HMDB0036881)

Animal

Animal (HMDB: HMDB0036881)

Exogenous

Food

Food (HMDB: HMDB0036881)

Herb and spice

Spice

Turmeric (FooDB: FOOD00068)

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0036881)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0036881)

Cellular process

Cell signaling (HMDB: HMDB0036881)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0036881)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0036881)

Nutrient

Nutrient (HMDB: HMDB0036881)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0036881)

Emulsifier (HMDB: HMDB0036881)

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	1.76 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	0.084 g/L	ALOGPS
logP	3.05	ALOGPS
logP	3.14	ChemAxon
logS	-3.4	ALOGPS
pKa (Strongest Acidic)	16.54	ChemAxon
pKa (Strongest Basic)	-6.2	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	1	ChemAxon
Refractivity	72.57 m³·mol⁻¹	ChemAxon
Polarizability	25.89 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
DeepCCS	[M+H]+	167.757	30932474
DeepCCS	[M-H]-	165.399	30932474
DeepCCS	[M-2H]-	198.285	30932474
DeepCCS	[M+Na]+	173.85	30932474
AllCCS	[M+H]+	154.2	32859911
AllCCS	[M+H-H2O]+	150.2	32859911
AllCCS	[M+NH4]+	157.8	32859911
AllCCS	[M+Na]+	158.8	32859911
AllCCS	[M-H]-	159.3	32859911
AllCCS	[M+Na-2H]-	159.7	32859911
AllCCS	[M+HCOO]-	160.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Germacrone-13-al	C\C(C=O)=C1\C\C=C(C)\CCC=C(C)CC1=O	2500.9	Standard polar	33892256
Germacrone-13-al	C\C(C=O)=C1\C\C=C(C)\CCC=C(C)CC1=O	1891.7	Standard non polar	33892256
Germacrone-13-al	C\C(C=O)=C1\C\C=C(C)\CCC=C(C)CC1=O	1889.2	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Germacrone-13-al,1TMS,isomer #1	CC1=CCC/C(C)=C/C/C(=C(/C)C=O)C(O[Si](C)(C)C)=C1	2157.3	Semi standard non polar	33892256
Germacrone-13-al,1TMS,isomer #1	CC1=CCC/C(C)=C/C/C(=C(/C)C=O)C(O[Si](C)(C)C)=C1	1930.7	Standard non polar	33892256
Germacrone-13-al,1TBDMS,isomer #1	CC1=CCC/C(C)=C/C/C(=C(/C)C=O)C(O[Si](C)(C)C(C)(C)C)=C1	2349.2	Semi standard non polar	33892256
Germacrone-13-al,1TBDMS,isomer #1	CC1=CCC/C(C)=C/C/C(=C(/C)C=O)C(O[Si](C)(C)C(C)(C)C)=C1	2073.5	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Germacrone-13-al GC-MS (Non-derivatized) - 70eV, Positive	splash10-014i-4390000000-3cbf045621f190c8e3c7	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Germacrone-13-al 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 - Germacrone-13-al 10V, Positive-QTOF	splash10-001i-0290000000-751dc628bfc373e22599	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacrone-13-al 20V, Positive-QTOF	splash10-0a6r-9610000000-059c3cd82067083196e8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacrone-13-al 40V, Positive-QTOF	splash10-0uxr-9410000000-c2e43e848a7e98527c51	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacrone-13-al 10V, Negative-QTOF	splash10-001i-1090000000-054729781108667f92c4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacrone-13-al 20V, Negative-QTOF	splash10-057i-4980000000-0dd93c063ca5b380b342	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacrone-13-al 40V, Negative-QTOF	splash10-052f-9520000000-ae4e693969f26dd4ec6c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacrone-13-al 10V, Positive-QTOF	splash10-0159-0190000000-2fbb3413cb4a22c988f1	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacrone-13-al 20V, Positive-QTOF	splash10-0670-0790000000-a40323842dd26018c9f8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacrone-13-al 40V, Positive-QTOF	splash10-0kii-0920000000-3837d8e62890beeb7fd6	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacrone-13-al 10V, Negative-QTOF	splash10-001i-0090000000-f6fb127b617288c4bb8c	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacrone-13-al 20V, Negative-QTOF	splash10-0ue9-0190000000-e7f76730e88b84c747a3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Germacrone-13-al 40V, Negative-QTOF	splash10-00b9-0920000000-ed4365c58a4572aec9bb	2021-09-24	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

FDB015839

KNApSAcK ID

C00011735

Chemspider ID

30777171

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

14633001

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1857791

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 Germacrone-13-al (HMDB0036881)

MOL for HMDB0036881 (Germacrone-13-al)

3D MOL for HMDB0036881 (Germacrone-13-al)

3D SDF for HMDB0036881 (Germacrone-13-al)

3D-SDF for HMDB0036881 (Germacrone-13-al)

PDB for HMDB0036881 (Germacrone-13-al)

3D PDB for HMDB0036881 (Germacrone-13-al)

SMILES for HMDB0036881 (Germacrone-13-al)

INCHI for HMDB0036881 (Germacrone-13-al)

Structure for HMDB0036881 (Germacrone-13-al)

3D Structure for HMDB0036881 (Germacrone-13-al)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra