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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 18:05:14 UTC

Update Date

2023-02-21 17:23:16 UTC

HMDB ID

HMDB0033371

Secondary Accession Numbers

HMDB33371

Metabolite Identification

Common Name

Citronellyl formate

Description

Citronellyl formate 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 small amount of articles have been published on Citronellyl formate.

Structure

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

HMDB0033371
     RDKit          3D
Citronellyl formate
 33 32  0  0  0  0  0  0  0  0999 V2000
   -3.8238   -0.7363   -0.8946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7507    0.0938   -0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5451    1.4612   -0.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225   -0.3771    0.6795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9337    0.3203    1.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4260   -0.2887    1.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0232   -0.4215    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1902   -1.3455   -0.8936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4030   -0.9090   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5411   -0.2442    0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991    1.0262    0.1512 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3294    2.2334    0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2352    2.3888    0.7861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8078   -1.7814   -0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8481   -0.3487   -0.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7381   -0.6943   -2.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7137    2.2196   -0.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5052    1.5702   -1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2315    1.6890   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2510   -1.3943    1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8899    1.4184    1.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118    0.4345    2.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0552    0.3409    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097   -1.3264    1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8899    0.5839   -0.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4472   -0.8205   -1.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9005   -2.0284   -1.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4286   -1.9914   -0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4210   -2.0189    0.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6397   -0.9917   -1.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4710   -0.8787    0.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5421   -0.2743    1.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8723    3.0912   -0.1926 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
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
M  END

HMDB0033371
     RDKit          3D
Citronellyl formate
 33 32  0  0  0  0  0  0  0  0999 V2000
   -3.8238   -0.7363   -0.8946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7507    0.0938   -0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5451    1.4612   -0.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225   -0.3771    0.6795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9337    0.3203    1.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4260   -0.2887    1.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0232   -0.4215    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1902   -1.3455   -0.8936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4030   -0.9090   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5411   -0.2442    0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991    1.0262    0.1512 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3294    2.2334    0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2352    2.3888    0.7861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8078   -1.7814   -0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8481   -0.3487   -0.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7381   -0.6943   -2.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7137    2.2196   -0.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5052    1.5702   -1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2315    1.6890   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2510   -1.3943    1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8899    1.4184    1.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118    0.4345    2.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0552    0.3409    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097   -1.3264    1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8899    0.5839   -0.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4472   -0.8205   -1.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9005   -2.0284   -1.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4286   -1.9914   -0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4210   -2.0189    0.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6397   -0.9917   -1.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4710   -0.8787    0.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5421   -0.2743    1.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8723    3.0912   -0.1926 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
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  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      -8.057  -0.921   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -5.390  -0.921   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -2.723  -5.541   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.390  -4.001   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -6.724  -3.231   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -4.056  -3.231   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.389  -3.231   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -0.055  -4.001   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       2.612  -4.001   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -6.724  -1.691   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -2.723  -4.001   0.000  0.00  0.00           C+0
HETATM   12  O   UNK     0       3.946  -3.231   0.000  0.00  0.00           O+0
HETATM   13  O   UNK     0       1.278  -3.231   0.000  0.00  0.00           O+0
CONECT    1   10                                                            
CONECT    2   10                                                            
CONECT    3   11                                                            
CONECT    4    5    6                                                       
CONECT    5    4   10                                                       
CONECT    6    4   11                                                       
CONECT    7    8   11                                                       
CONECT    8    7   13                                                       
CONECT    9   12   13                                                       
CONECT   10    1    2    5                                                  
CONECT   11    3    6    7                                                  
CONECT   12    9                                                            
CONECT   13    8    9                                                       
MASTER        0    0    0    0    0    0    0    0   13    0   24    0
END

COMPND    HMDB0033371
HETATM    1  C1  UNL     1      -3.824  -0.736  -0.895  1.00  0.00           C  
HETATM    2  C2  UNL     1      -2.751   0.094  -0.296  1.00  0.00           C  
HETATM    3  C3  UNL     1      -2.545   1.461  -0.846  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.022  -0.377   0.680  1.00  0.00           C  
HETATM    5  C5  UNL     1      -0.934   0.320   1.367  1.00  0.00           C  
HETATM    6  C6  UNL     1       0.426  -0.289   1.343  1.00  0.00           C  
HETATM    7  C7  UNL     1       1.023  -0.421   0.006  1.00  0.00           C  
HETATM    8  C8  UNL     1       0.190  -1.345  -0.894  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.403  -0.909  -0.067  1.00  0.00           C  
HETATM   10  C10 UNL     1       3.541  -0.244   0.545  1.00  0.00           C  
HETATM   11  O1  UNL     1       3.899   1.026   0.151  1.00  0.00           O  
HETATM   12  C11 UNL     1       3.329   2.233   0.240  1.00  0.00           C  
HETATM   13  O2  UNL     1       2.235   2.389   0.786  1.00  0.00           O  
HETATM   14  H1  UNL     1      -3.808  -1.781  -0.532  1.00  0.00           H  
HETATM   15  H2  UNL     1      -4.848  -0.349  -0.622  1.00  0.00           H  
HETATM   16  H3  UNL     1      -3.738  -0.694  -2.004  1.00  0.00           H  
HETATM   17  H4  UNL     1      -2.714   2.220  -0.051  1.00  0.00           H  
HETATM   18  H5  UNL     1      -1.505   1.570  -1.264  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.231   1.689  -1.665  1.00  0.00           H  
HETATM   20  H7  UNL     1      -2.251  -1.394   1.045  1.00  0.00           H  
HETATM   21  H8  UNL     1      -0.890   1.418   1.057  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.312   0.434   2.441  1.00  0.00           H  
HETATM   23  H10 UNL     1       1.055   0.341   2.030  1.00  0.00           H  
HETATM   24  H11 UNL     1       0.410  -1.326   1.814  1.00  0.00           H  
HETATM   25  H12 UNL     1       0.890   0.584  -0.513  1.00  0.00           H  
HETATM   26  H13 UNL     1      -0.447  -0.821  -1.596  1.00  0.00           H  
HETATM   27  H14 UNL     1       0.900  -2.028  -1.445  1.00  0.00           H  
HETATM   28  H15 UNL     1      -0.429  -1.991  -0.248  1.00  0.00           H  
HETATM   29  H16 UNL     1       2.421  -2.019   0.213  1.00  0.00           H  
HETATM   30  H17 UNL     1       2.640  -0.992  -1.186  1.00  0.00           H  
HETATM   31  H18 UNL     1       4.471  -0.879   0.328  1.00  0.00           H  
HETATM   32  H19 UNL     1       3.542  -0.274   1.677  1.00  0.00           H  
HETATM   33  H20 UNL     1       3.872   3.091  -0.193  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    4    4
CONECT    3   17   18   19
CONECT    4    5   20
CONECT    5    6   21   22
CONECT    6    7   23   24
CONECT    7    8    9   25
CONECT    8   26   27   28
CONECT    9   10   29   30
CONECT   10   11   31   32
CONECT   11   12
CONECT   12   13   13   33
END

HMDB0033371
     RDKit          3D
Citronellyl formate
 33 32  0  0  0  0  0  0  0  0999 V2000
   -3.8238   -0.7363   -0.8946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7507    0.0938   -0.2961 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5451    1.4612   -0.8464 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0225   -0.3771    0.6795 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9337    0.3203    1.3666 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4260   -0.2887    1.3428 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0232   -0.4215    0.0057 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1902   -1.3455   -0.8936 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4030   -0.9090   -0.0668 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5411   -0.2442    0.5454 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8991    1.0262    0.1512 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.3294    2.2334    0.2402 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2352    2.3888    0.7861 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8078   -1.7814   -0.5320 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8481   -0.3487   -0.6220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7381   -0.6943   -2.0043 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7137    2.2196   -0.0508 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5052    1.5702   -1.2643 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2315    1.6890   -1.6651 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2510   -1.3943    1.0448 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8899    1.4184    1.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3118    0.4345    2.4408 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0552    0.3409    2.0303 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4097   -1.3264    1.8143 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8899    0.5839   -0.5128 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4472   -0.8205   -1.5956 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9005   -2.0284   -1.4449 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4286   -1.9914   -0.2481 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4210   -2.0189    0.2132 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6397   -0.9917   -1.1857 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4710   -0.8787    0.3277 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5421   -0.2743    1.6771 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8723    3.0912   -0.1926 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
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  3 18  1  0
  3 19  1  0
  4 20  1  0
  5 21  1  0
  5 22  1  0
  6 23  1  0
  6 24  1  0
  7 25  1  0
  8 26  1  0
  8 27  1  0
  8 28  1  0
  9 29  1  0
  9 30  1  0
 10 31  1  0
 10 32  1  0
 12 33  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Citronellyl formic acid	Generator
(+)-3,7-Dimethyloct-6-enyl formate	HMDB
(-)-3,7-Dimethyloct-6-enyl formate	HMDB
(1)-3,7-Dimethyloct-6-enyl formate	HMDB
2, 6-Dimethyl-2-octen-8-yl formate	HMDB
2,6-Dimethyl-2-octen-8-yl formate	HMDB
3,7-Dimethyl-6-octen-1-yl formate	HMDB
3,7-Dimethyl-6-octen-1-yl methanoate	HMDB
3,7-Dimethyl-6-octenyl formate	HMDB
6-Octen-1-ol, 3,7-dimethyl-, 1-formate	HMDB
6-Octen-1-ol, 3,7-dimethyl-, formate	HMDB
Citronellol formate	HMDB
Citronellol formate (6ci)	HMDB
Citronellyl methanoate	HMDB
Citronelyl formate	HMDB
FEMA 2314	HMDB
Formic acid, 3,7-dimethyl-6-octen-1-yl ester	HMDB
Formic acid, citronellyl ester	HMDB

Chemical Formula

C₁₁H₂₀O₂

Average Molecular Weight

184.2753

Monoisotopic Molecular Weight

184.146329884

IUPAC Name

3,7-dimethyloct-6-en-1-yl formate

Traditional Name

citronellyl formate

CAS Registry Number

105-85-1

SMILES

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

InChI Identifier

InChI=1S/C11H20O2/c1-10(2)5-4-6-11(3)7-8-13-9-12/h5,9,11H,4,6-8H2,1-3H3

InChI Key

DZNVIZQPWLDQHI-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

carboxylic ester (CHEBI:31406 )
Acyclic monoterpenoids (C12295 )
Acyclic monoterpenoids (LMPR0102010014 )

Ontology

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0033371)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0033371)

Source

Endogenous

Endogenous (HMDB: HMDB0033371)

Plant

Plant (HMDB: HMDB0033371)

Animal

Animal (HMDB: HMDB0033371)

Exogenous

Food

Food (HMDB: HMDB0033371)

Fruit

Citrus

Citrus (FooDB: FOOD00859)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Exogenous (HMDB: HMDB0033371)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0033371)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0033371)

Lipid metabolism pathway (HMDB: HMDB0033371)

Cellular process

Cell signaling (HMDB: HMDB0033371)

Biochemical process

Lipid transport (HMDB: HMDB0033371)

Role

Biological role

Energy source (HMDB: HMDB0033371)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0033371)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0033371)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	235.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	19.61 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	3.800	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.14 g/L	ALOGPS
logP	3.86	ALOGPS
logP	3.14	ChemAxon
logS	-3.1	ALOGPS
pKa (Strongest Basic)	-6.8	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	7	ChemAxon
Refractivity	55.15 m³·mol⁻¹	ChemAxon
Polarizability	22.24 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]+	144.899	31661259
DarkChem	[M-H]-	140.263	31661259
DeepCCS	[M+H]+	143.134	30932474
DeepCCS	[M-H]-	140.399	30932474
DeepCCS	[M-2H]-	176.687	30932474
DeepCCS	[M+Na]+	152.204	30932474
AllCCS	[M+H]+	146.0	32859911
AllCCS	[M+H-H2O]+	142.2	32859911
AllCCS	[M+NH4]+	149.5	32859911
AllCCS	[M+Na]+	150.5	32859911
AllCCS	[M-H]-	147.5	32859911
AllCCS	[M+Na-2H]-	149.1	32859911
AllCCS	[M+HCOO]-	150.9	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.	7.81 minutes	32390414
Predicted by Siyang on May 30, 2022	15.0499 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.41 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	23.7 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2301.7 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	450.3 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	175.2 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	255.6 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	161.2 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	575.4 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	654.5 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	73.3 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1242.7 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	472.4 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	1220.4 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	407.1 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	382.8 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	344.0 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	392.6 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	8.9 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citronellyl formate	CC(CCOC=O)CCC=C(C)C	1582.9	Standard polar	33892256
Citronellyl formate	CC(CCOC=O)CCC=C(C)C	1244.0	Standard non polar	33892256
Citronellyl formate	CC(CCOC=O)CCC=C(C)C	1327.3	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 formate EI-B (Non-derivatized)	splash10-014i-9100000000-716f863fe49bf99429d8	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Citronellyl formate EI-B (Non-derivatized)	splash10-00lr-9100000000-62cabec8ecf5956214be	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Citronellyl formate EI-B (Non-derivatized)	splash10-014i-9100000000-716f863fe49bf99429d8	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Citronellyl formate EI-B (Non-derivatized)	splash10-00lr-9100000000-62cabec8ecf5956214be	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citronellyl formate GC-MS (Non-derivatized) - 70eV, Positive	splash10-067l-9400000000-77d836f97f08fb4c4776	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citronellyl formate GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citronellyl formate 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 formate 10V, Positive-QTOF	splash10-000i-1900000000-8f1a33518143ec5cf5a0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl formate 20V, Positive-QTOF	splash10-000i-8900000000-d85cb2976e510935416f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl formate 40V, Positive-QTOF	splash10-066r-9100000000-880577b40eb349d5b946	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl formate 10V, Negative-QTOF	splash10-001i-1900000000-4137d9bcef8e50645e75	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl formate 20V, Negative-QTOF	splash10-001l-7900000000-6458a8d8fbf5940091ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl formate 40V, Negative-QTOF	splash10-0006-9300000000-48ea1dc5cad87035e991	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl formate 10V, Negative-QTOF	splash10-053r-2900000000-9ef1292fc21e65068093	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl formate 20V, Negative-QTOF	splash10-0006-9000000000-d948d5d95ae14e701f57	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl formate 40V, Negative-QTOF	splash10-0006-9000000000-20647fba0207a01d7882	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl formate 10V, Positive-QTOF	splash10-001i-9500000000-9c1e960dd6d4a64a24f8	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl formate 20V, Positive-QTOF	splash10-00lr-9000000000-0daad7e74fbe5b09ed38	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl formate 40V, Positive-QTOF	splash10-067l-9000000000-5c73ec0697fcfdc5222d	2021-09-22	Wishart Lab	View Spectrum

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX 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

KNApSAcK ID

Chemspider ID

KEGG Compound ID

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

7778

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1017871

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 formate (HMDB0033371)

MOL for HMDB0033371 (Citronellyl formate)

3D MOL for HMDB0033371 (Citronellyl formate)

3D SDF for HMDB0033371 (Citronellyl formate)

3D-SDF for HMDB0033371 (Citronellyl formate)

PDB for HMDB0033371 (Citronellyl formate)

3D PDB for HMDB0033371 (Citronellyl formate)

SMILES for HMDB0033371 (Citronellyl formate)

INCHI for HMDB0033371 (Citronellyl formate)

Structure for HMDB0033371 (Citronellyl formate)

3D Structure for HMDB0033371 (Citronellyl formate)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra

IR Spectra