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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:28:12 UTC

Update Date

2022-03-07 02:55:14 UTC

HMDB ID

HMDB0037228

Secondary Accession Numbers

HMDB37228

Metabolite Identification

Common Name

Citronellyl isobutyrate

Description

Citronellyl isobutyrate belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol. Based on a literature review a significant number of articles have been published on Citronellyl isobutyrate.

Structure

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

HMDB0037228
     RDKit          3D
Citronellyl isobutyrate
 42 41  0  0  0  0  0  0  0  0999 V2000
    3.0502    1.8772   -0.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7837    0.7139   -0.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8768    0.1098   -1.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4829    0.2099    0.9349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4010    0.7935    1.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2796   -0.1114    2.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4858   -0.6642    0.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524   -1.4854    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6357   -1.4770    1.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5566   -2.1120    0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2143   -1.1918   -0.2996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0523   -0.1857    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2146   -0.1167    1.4091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7303    0.7684   -0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6350    0.0393   -1.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6193    1.6646    0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4171    2.1459   -1.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1893    2.7762   -0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9590    1.6756   -0.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5289   -0.8161   -1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7918   -0.0673   -0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1965    0.8027   -1.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0368   -0.6312    1.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8721    1.0952    2.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0449    1.7292    1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6522   -0.9230    2.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5676    0.4759    2.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0699    0.1841    0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7692   -2.4033   -0.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5638   -0.9293   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2628   -1.8714    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1153   -2.3261    2.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1774   -0.8658    2.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3628   -2.6136    1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1266   -2.9353   -0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0131    1.4289   -1.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1267    0.0071   -2.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421   -0.9994   -1.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6342    0.5215   -1.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2946    1.0577    0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3180    2.2222   -0.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0652    2.4269    0.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  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  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
  1 17  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
  7 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
M  END


  Mrv0541 05061309392D          

 16 15  0  0  0  0            999 V2000
   -5.3329    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6184    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5263    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8118    0.6039    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605    2.6664    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1895    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9039    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4750    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0461    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3316    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6184    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8118    1.4289    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7605    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974    1.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0974    2.6664    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.3829    1.4289    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  7  6  1  0  0  0  0
  8  6  1  0  0  0  0
 10  9  1  0  0  0  0
 11  1  1  0  0  0  0
 11  2  1  0  0  0  0
 11  7  2  0  0  0  0
 12  3  1  0  0  0  0
 12  4  1  0  0  0  0
 13  5  1  0  0  0  0
 13  8  1  0  0  0  0
 13  9  1  0  0  0  0
 14 12  1  0  0  0  0
 15 14  2  0  0  0  0
 16 10  1  0  0  0  0
 16 14  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037228

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CCOC(=O)C(C)C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C14H26O2/c1-11(2)7-6-8-13(5)9-10-16-14(15)12(3)4/h7,12-13H,6,8-10H2,1-5H3

> <INCHI_KEY>
ZGPPERKMXSGYRK-UHFFFAOYSA-N

> <FORMULA>
C14H26O2

> <MOLECULAR_WEIGHT>
226.355

> <EXACT_MASS>
226.193280076

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
28.353838863953712

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7-dimethyloct-6-en-1-yl 2-methylpropanoate

> <ALOGPS_LOGP>
4.86

> <JCHEM_LOGP>
4.436702852999998

> <ALOGPS_LOGS>
-4.07

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.065525336092086

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
68.839

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.94e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,7-dimethyloct-6-en-1-yl 2-methylpropanoate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0037228
     RDKit          3D
Citronellyl isobutyrate
 42 41  0  0  0  0  0  0  0  0999 V2000
    3.0502    1.8772   -0.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7837    0.7139   -0.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8768    0.1098   -1.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4829    0.2099    0.9349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4010    0.7935    1.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2796   -0.1114    2.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4858   -0.6642    0.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524   -1.4854    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6357   -1.4770    1.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5566   -2.1120    0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2143   -1.1918   -0.2996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0523   -0.1857    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2146   -0.1167    1.4091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7303    0.7684   -0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6350    0.0393   -1.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6193    1.6646    0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4171    2.1459   -1.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1893    2.7762   -0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9590    1.6756   -0.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5289   -0.8161   -1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7918   -0.0673   -0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1965    0.8027   -1.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0368   -0.6312    1.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8721    1.0952    2.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0449    1.7292    1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6522   -0.9230    2.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5676    0.4759    2.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0699    0.1841    0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7692   -2.4033   -0.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5638   -0.9293   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2628   -1.8714    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1153   -2.3261    2.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1774   -0.8658    2.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3628   -2.6136    1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1266   -2.9353   -0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0131    1.4289   -1.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1267    0.0071   -2.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421   -0.9994   -1.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6342    0.5215   -1.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2946    1.0577    0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3180    2.2222   -0.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0652    2.4269    0.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  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  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
  1 17  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
  7 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  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      -9.955   2.667   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.621   4.977   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       4.716   3.437   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       3.382   1.127   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -3.286   4.977   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -5.954   3.437   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -7.287   2.667   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -4.620   2.667   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -1.953   2.667   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -0.619   3.437   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -8.621   3.437   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       3.382   2.667   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -3.286   3.437   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       2.048   3.437   0.000  0.00  0.00           C+0
HETATM   15  O   UNK     0       2.048   4.977   0.000  0.00  0.00           O+0
HETATM   16  O   UNK     0       0.715   2.667   0.000  0.00  0.00           O+0
CONECT    1   11                                                            
CONECT    2   11                                                            
CONECT    3   12                                                            
CONECT    4   12                                                            
CONECT    5   13                                                            
CONECT    6    7    8                                                       
CONECT    7    6   11                                                       
CONECT    8    6   13                                                       
CONECT    9   10   13                                                       
CONECT   10    9   16                                                       
CONECT   11    1    2    7                                                  
CONECT   12    3    4   14                                                  
CONECT   13    5    8    9                                                  
CONECT   14   12   15   16                                                  
CONECT   15   14                                                            
CONECT   16   10   14                                                       
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0037228
HETATM    1  C1  UNL     1       3.050   1.877  -0.790  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.784   0.714  -0.242  1.00  0.00           C  
HETATM    3  C3  UNL     1       4.877   0.110  -1.038  1.00  0.00           C  
HETATM    4  C4  UNL     1       3.483   0.210   0.935  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.401   0.794   1.743  1.00  0.00           C  
HETATM    6  C6  UNL     1       1.280  -0.111   2.065  1.00  0.00           C  
HETATM    7  C7  UNL     1       0.486  -0.664   0.919  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.352  -1.485   0.005  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.636  -1.477   1.532  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.557  -2.112   0.555  1.00  0.00           C  
HETATM   11  O1  UNL     1      -2.214  -1.192  -0.300  1.00  0.00           O  
HETATM   12  C11 UNL     1      -3.052  -0.186   0.159  1.00  0.00           C  
HETATM   13  O2  UNL     1      -3.215  -0.117   1.409  1.00  0.00           O  
HETATM   14  C12 UNL     1      -3.730   0.768  -0.763  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.635   0.039  -1.739  1.00  0.00           C  
HETATM   16  C14 UNL     1      -4.619   1.665   0.070  1.00  0.00           C  
HETATM   17  H1  UNL     1       3.417   2.146  -1.787  1.00  0.00           H  
HETATM   18  H2  UNL     1       3.189   2.776  -0.134  1.00  0.00           H  
HETATM   19  H3  UNL     1       1.959   1.676  -0.793  1.00  0.00           H  
HETATM   20  H4  UNL     1       4.529  -0.816  -1.551  1.00  0.00           H  
HETATM   21  H5  UNL     1       5.792  -0.067  -0.445  1.00  0.00           H  
HETATM   22  H6  UNL     1       5.197   0.803  -1.870  1.00  0.00           H  
HETATM   23  H7  UNL     1       4.037  -0.631   1.327  1.00  0.00           H  
HETATM   24  H8  UNL     1       2.872   1.095   2.734  1.00  0.00           H  
HETATM   25  H9  UNL     1       2.045   1.729   1.245  1.00  0.00           H  
HETATM   26  H10 UNL     1       1.652  -0.923   2.741  1.00  0.00           H  
HETATM   27  H11 UNL     1       0.568   0.476   2.723  1.00  0.00           H  
HETATM   28  H12 UNL     1       0.070   0.184   0.320  1.00  0.00           H  
HETATM   29  H13 UNL     1       0.769  -2.403  -0.331  1.00  0.00           H  
HETATM   30  H14 UNL     1       1.564  -0.929  -0.940  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.263  -1.871   0.464  1.00  0.00           H  
HETATM   32  H16 UNL     1      -0.115  -2.326   2.068  1.00  0.00           H  
HETATM   33  H17 UNL     1      -1.177  -0.866   2.250  1.00  0.00           H  
HETATM   34  H18 UNL     1      -2.363  -2.614   1.180  1.00  0.00           H  
HETATM   35  H19 UNL     1      -1.127  -2.935  -0.029  1.00  0.00           H  
HETATM   36  H20 UNL     1      -3.013   1.429  -1.286  1.00  0.00           H  
HETATM   37  H21 UNL     1      -4.127   0.007  -2.719  1.00  0.00           H  
HETATM   38  H22 UNL     1      -4.742  -0.999  -1.387  1.00  0.00           H  
HETATM   39  H23 UNL     1      -5.634   0.522  -1.820  1.00  0.00           H  
HETATM   40  H24 UNL     1      -5.295   1.058   0.729  1.00  0.00           H  
HETATM   41  H25 UNL     1      -5.318   2.222  -0.616  1.00  0.00           H  
HETATM   42  H26 UNL     1      -4.065   2.427   0.623  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3    4    4
CONECT    3   20   21   22
CONECT    4    5   23
CONECT    5    6   24   25
CONECT    6    7   26   27
CONECT    7    8    9   28
CONECT    8   29   30   31
CONECT    9   10   32   33
CONECT   10   11   34   35
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   16   36
CONECT   15   37   38   39
CONECT   16   40   41   42
END

HMDB0037228
     RDKit          3D
Citronellyl isobutyrate
 42 41  0  0  0  0  0  0  0  0999 V2000
    3.0502    1.8772   -0.7902 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7837    0.7139   -0.2418 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8768    0.1098   -1.0380 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4829    0.2099    0.9349 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4010    0.7935    1.7434 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2796   -0.1114    2.0648 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4858   -0.6642    0.9189 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3524   -1.4854    0.0054 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6357   -1.4770    1.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5566   -2.1120    0.5546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2143   -1.1918   -0.2996 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0523   -0.1857    0.1586 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2146   -0.1167    1.4091 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7303    0.7684   -0.7632 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6350    0.0393   -1.7391 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6193    1.6646    0.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4171    2.1459   -1.7871 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1893    2.7762   -0.1338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9590    1.6756   -0.7929 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5289   -0.8161   -1.5511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7918   -0.0673   -0.4452 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1965    0.8027   -1.8697 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0368   -0.6312    1.3272 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8721    1.0952    2.7341 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0449    1.7292    1.2447 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6522   -0.9230    2.7415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5676    0.4759    2.7235 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0699    0.1841    0.3202 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7692   -2.4033   -0.3312 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5638   -0.9293   -0.9404 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2628   -1.8714    0.4641 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1153   -2.3261    2.0679 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1774   -0.8658    2.2501 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3628   -2.6136    1.1804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1266   -2.9353   -0.0290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0131    1.4289   -1.2858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1267    0.0071   -2.7192 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7421   -0.9994   -1.3865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6342    0.5215   -1.8202 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2946    1.0577    0.7287 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3180    2.2222   -0.6161 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0652    2.4269    0.6226 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  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  2  0
 12 14  1  0
 14 15  1  0
 14 16  1  0
  1 17  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
  7 28  1  0
  8 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 10 35  1  0
 14 36  1  0
 15 37  1  0
 15 38  1  0
 15 39  1  0
 16 40  1  0
 16 41  1  0
 16 42  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Citronellyl isobutyric acid	Generator
3,7-Dimethyl-6-octen-1-yl 2-methylpropanoate	HMDB
3,7-Dimethyl-6-octen-1-yl isobutyrate	HMDB
3,7-Dimethyl-6-octenyl 2-methylpropanoate	HMDB
3,7-Dimethyl-6-octenyl isobutyrate	HMDB
3,7-Dimethyl-6-octenyl methylpropionate	HMDB
3,7-Dimethyloct-6-enyl isobutyrate	HMDB
Citronellyl 2-methylpropanoate	HMDB
Citronellyl isobutanoate	HMDB
FEMA 2313	HMDB
Isobutyric acid, 3,7-dimethyl-6-octenyl ester	HMDB
Isobutyric acid, 3,7-dimethyl-6-octenyl ester (8ci)	HMDB
Propanoic acid, 2-methyl-, 3,7-dimethyl-6-octen-1-yl ester	HMDB
Propanoic acid, 2-methyl-, 3,7-dimethyl-6-octenyl	HMDB
Propanoic acid, 2-methyl-, 3,7-dimethyl-6-octenyl ester	HMDB

Chemical Formula

C₁₄H₂₆O₂

Average Molecular Weight

226.355

Monoisotopic Molecular Weight

226.193280076

IUPAC Name

3,7-dimethyloct-6-en-1-yl 2-methylpropanoate

Traditional Name

3,7-dimethyloct-6-en-1-yl 2-methylpropanoate

CAS Registry Number

97-89-2

SMILES

CC(CCOC(=O)C(C)C)CCC=C(C)C

InChI Identifier

InChI=1S/C14H26O2/c1-11(2)7-6-8-13(5)9-10-16-14(15)12(3)4/h7,12-13H,6,8-10H2,1-5H3

InChI Key

ZGPPERKMXSGYRK-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty alcohol esters. These are ester derivatives of a fatty alcohol.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty alcohol esters

Direct Parent

Fatty alcohol esters

Alternative Parents

Substituents

Fatty alcohol ester
Monoterpenoid
Acyclic monoterpenoid
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0037228)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037228)

Source

Endogenous

Endogenous (HMDB: HMDB0037228)

Plant

Plant (HMDB: HMDB0037228)

Animal

Animal (HMDB: HMDB0037228)

Exogenous

Food

Food (HMDB: HMDB0037228)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0037228)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037228)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037228)

Lipid metabolism pathway (HMDB: HMDB0037228)

Cellular process

Cell signaling (HMDB: HMDB0037228)

Biochemical process

Lipid transport (HMDB: HMDB0037228)

Role

Biological role

Energy source (HMDB: HMDB0037228)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037228)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037228)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	249.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.68 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.068 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.019 g/L	ALOGPS
logP	4.86	ALOGPS
logP	4.44	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	68.84 m³·mol⁻¹	ChemAxon
Polarizability	28.35 Å³	ChemAxon
Number of Rings	0	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]+	156.048	31661259
DarkChem	[M-H]-	154.274	31661259
DeepCCS	[M+H]+	158.754	30932474
DeepCCS	[M-H]-	156.396	30932474
DeepCCS	[M-2H]-	190.481	30932474
DeepCCS	[M+Na]+	165.402	30932474
AllCCS	[M+H]+	158.4	32859911
AllCCS	[M+H-H2O]+	155.0	32859911
AllCCS	[M+NH4]+	161.5	32859911
AllCCS	[M+Na]+	162.4	32859911
AllCCS	[M-H]-	161.0	32859911
AllCCS	[M+Na-2H]-	162.3	32859911
AllCCS	[M+HCOO]-	163.7	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	9.0 minutes	32390414
Predicted by Siyang on May 30, 2022	19.4778 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.23 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2987.9 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	647.6 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	235.7 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	357.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	200.4 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	812.4 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	892.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	80.6 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1570.2 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	651.6 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	1560.5 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	525.8 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	448.7 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	396.5 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	555.2 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	7.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citronellyl isobutyrate	CC(CCOC(=O)C(C)C)CCC=C(C)C	1752.8	Standard polar	33892256
Citronellyl isobutyrate	CC(CCOC(=O)C(C)C)CCC=C(C)C	1435.3	Standard non polar	33892256
Citronellyl isobutyrate	CC(CCOC(=O)C(C)C)CCC=C(C)C	1475.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Citronellyl isobutyrate EI-B (Non-derivatized)	splash10-00rx-9100000000-a6ccc17946f97bcd2f3d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Citronellyl isobutyrate EI-B (Non-derivatized)	splash10-00rx-9100000000-a6ccc17946f97bcd2f3d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citronellyl isobutyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-10e870fbfc21a4db1efe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citronellyl isobutyrate 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 - Citronellyl isobutyrate 10V, Positive-QTOF	splash10-004i-5690000000-69c546a8c324a6d6e37e	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl isobutyrate 20V, Positive-QTOF	splash10-00dr-9510000000-07d542dc490a0e9765e5	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl isobutyrate 40V, Positive-QTOF	splash10-0603-9000000000-3ab69aa5031b8140ba87	2016-06-20	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl isobutyrate 10V, Negative-QTOF	splash10-004i-3290000000-7091c18a4e3253764342	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl isobutyrate 20V, Negative-QTOF	splash10-000i-9220000000-5e623c4c346bc7fb70d4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl isobutyrate 40V, Negative-QTOF	splash10-000i-9200000000-3d821da99afbfebf8e77	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl isobutyrate 10V, Negative-QTOF	splash10-000i-9120000000-805cbab6fe7ee0962de3	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl isobutyrate 20V, Negative-QTOF	splash10-000i-9000000000-a53fc6e3c901b8f08802	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl isobutyrate 40V, Negative-QTOF	splash10-000i-9000000000-f854ad9a4431e005872a	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl isobutyrate 10V, Positive-QTOF	splash10-001r-9410000000-a258f1427f2cac4f05b8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl isobutyrate 20V, Positive-QTOF	splash10-001i-9100000000-86e34155887f56e5060f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl isobutyrate 40V, Positive-QTOF	splash10-00l6-9000000000-16cc25abbb3617e87956	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

FDB016235

KNApSAcK ID

Not Available

Chemspider ID

54946

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

60985

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1019711

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 Citronellyl isobutyrate (HMDB0037228)

MOL for HMDB0037228 (Citronellyl isobutyrate)

3D MOL for HMDB0037228 (Citronellyl isobutyrate)

3D SDF for HMDB0037228 (Citronellyl isobutyrate)

3D-SDF for HMDB0037228 (Citronellyl isobutyrate)

PDB for HMDB0037228 (Citronellyl isobutyrate)

3D PDB for HMDB0037228 (Citronellyl isobutyrate)

SMILES for HMDB0037228 (Citronellyl isobutyrate)

INCHI for HMDB0037228 (Citronellyl isobutyrate)

Structure for HMDB0037228 (Citronellyl isobutyrate)

3D Structure for HMDB0037228 (Citronellyl isobutyrate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra