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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:48:30 UTC

Update Date

2022-03-07 02:53:16 UTC

HMDB ID

HMDB0032209

Secondary Accession Numbers

HMDB32209

Metabolite Identification

Common Name

Citronellyl trans-2-methyl-2-butenoate

Description

Citronellyl trans-2-methyl-2-butenoate 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 trans-2-methyl-2-butenoate.

Structure

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

HMDB0032209
     RDKit          3D
Citronellyl trans-2-methyl-2-butenoate
 43 42  0  0  0  0  0  0  0  0999 V2000
    5.7933   -1.4423    1.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4274   -1.4097    0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9838   -0.4706   -0.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8682    0.6334   -0.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939   -0.5243   -0.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8284   -1.4686   -0.4023 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974    0.4516   -1.5706 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8324    0.5519   -2.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2100    1.1782   -1.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    0.7403    0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6152    0.9588    1.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7504    1.4069    0.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9496    1.0709   -0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1774   -0.4073   -0.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3202   -0.8924    0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3709    0.0004    0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5719   -2.3563    0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8770   -0.5846    1.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9689   -2.3597    1.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5698   -1.2516    0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7418   -2.2041    0.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7733    1.4362    0.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9042    0.3484   -0.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4592    1.0897   -1.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4676   -0.5136   -2.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385    1.1348   -3.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1718    1.2571   -1.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0101    2.3223   -1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6662   -0.3993    0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1824    1.6204    1.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9695    0.0496    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4388    1.5811    0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9205    1.0779    1.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6015    2.5120    0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8179    1.5690    0.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9460    1.4481   -1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4288   -1.0786   -0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9983    0.5819    1.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6724    0.7800    0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2386   -0.5657    1.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5400   -2.5575   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5856   -2.7933    1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008   -2.9052   -0.3669 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
M  END


  Mrv0541 05061306242D          

 17 16  0  0  0  0            999 V2000
    2.8283    0.4934    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0309    1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3164    2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586    2.9684    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8283    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1138    0.9059    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8875    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6020    1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1730    1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7441    1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0296    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3164    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4586    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1138    1.7309    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3993    2.1434    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3993    2.9684    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.6849    1.7309    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  6  1  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 11 10  1  0  0  0  0
 12  2  1  0  0  0  0
 12  3  1  0  0  0  0
 12  8  2  0  0  0  0
 13  4  1  0  0  0  0
 13  9  1  0  0  0  0
 13 10  1  0  0  0  0
 14  5  1  0  0  0  0
 14  6  2  0  0  0  0
 15 14  1  0  0  0  0
 16 15  2  0  0  0  0
 17 11  1  0  0  0  0
 17 15  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0032209

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C(/C)C(=O)OCCC(C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C15H26O2/c1-6-14(5)15(16)17-11-10-13(4)9-7-8-12(2)3/h6,8,13H,7,9-11H2,1-5H3/b14-6+

> <INCHI_KEY>
UCFQYMKLDPWFHZ-MKMNVTDBSA-N

> <FORMULA>
C15H26O2

> <MOLECULAR_WEIGHT>
238.3657

> <EXACT_MASS>
238.193280076

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
29.827314160251646

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
3,7-dimethyloct-6-en-1-yl (2E)-2-methylbut-2-enoate

> <ALOGPS_LOGP>
5.36

> <JCHEM_LOGP>
4.964992551999999

> <ALOGPS_LOGS>
-4.12

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.84247693318821

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
74.3159

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.80e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
3,7-dimethyloct-6-en-1-yl (2E)-2-methylbut-2-enoate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0032209
     RDKit          3D
Citronellyl trans-2-methyl-2-butenoate
 43 42  0  0  0  0  0  0  0  0999 V2000
    5.7933   -1.4423    1.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4274   -1.4097    0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9838   -0.4706   -0.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8682    0.6334   -0.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939   -0.5243   -0.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8284   -1.4686   -0.4023 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974    0.4516   -1.5706 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8324    0.5519   -2.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2100    1.1782   -1.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    0.7403    0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6152    0.9588    1.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7504    1.4069    0.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9496    1.0709   -0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1774   -0.4073   -0.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3202   -0.8924    0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3709    0.0004    0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5719   -2.3563    0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8770   -0.5846    1.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9689   -2.3597    1.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5698   -1.2516    0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7418   -2.2041    0.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7733    1.4362    0.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9042    0.3484   -0.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4592    1.0897   -1.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4676   -0.5136   -2.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385    1.1348   -3.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1718    1.2571   -1.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0101    2.3223   -1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6662   -0.3993    0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1824    1.6204    1.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9695    0.0496    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4388    1.5811    0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9205    1.0779    1.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6015    2.5120    0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8179    1.5690    0.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9460    1.4481   -1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4288   -1.0786   -0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9983    0.5819    1.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6724    0.7800    0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2386   -0.5657    1.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5400   -2.5575   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5856   -2.7933    1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008   -2.9052   -0.3669 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  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       5.279   0.921   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -9.391   3.231   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -8.057   5.541   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -2.723   5.541   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.279   4.001   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       3.946   1.691   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -5.390   4.001   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -6.724   3.231   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -4.056   3.231   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -1.389   3.231   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      -0.055   4.001   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      -8.057   4.001   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      -2.723   4.001   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.946   3.231   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       2.612   4.001   0.000  0.00  0.00           C+0
HETATM   16  O   UNK     0       2.612   5.541   0.000  0.00  0.00           O+0
HETATM   17  O   UNK     0       1.278   3.231   0.000  0.00  0.00           O+0
CONECT    1    6                                                            
CONECT    2   12                                                            
CONECT    3   12                                                            
CONECT    4   13                                                            
CONECT    5   14                                                            
CONECT    6    1   14                                                       
CONECT    7    8    9                                                       
CONECT    8    7   12                                                       
CONECT    9    7   13                                                       
CONECT   10   11   13                                                       
CONECT   11   10   17                                                       
CONECT   12    2    3    8                                                  
CONECT   13    4    9   10                                                  
CONECT   14    5    6   15                                                  
CONECT   15   14   16   17                                                  
CONECT   16   15                                                            
CONECT   17   11   15                                                       
MASTER        0    0    0    0    0    0    0    0   17    0   32    0
END

COMPND    HMDB0032209
HETATM    1  C1  UNL     1       5.793  -1.442   1.127  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.427  -1.410   0.572  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.984  -0.471  -0.223  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.868   0.633  -0.611  1.00  0.00           C  
HETATM    5  C5  UNL     1       2.594  -0.524  -0.730  1.00  0.00           C  
HETATM    6  O1  UNL     1       1.828  -1.469  -0.402  1.00  0.00           O  
HETATM    7  O2  UNL     1       2.097   0.452  -1.571  1.00  0.00           O  
HETATM    8  C6  UNL     1       0.832   0.552  -2.093  1.00  0.00           C  
HETATM    9  C7  UNL     1      -0.210   1.178  -1.262  1.00  0.00           C  
HETATM   10  C8  UNL     1      -0.502   0.740   0.099  1.00  0.00           C  
HETATM   11  C9  UNL     1       0.615   0.959   1.102  1.00  0.00           C  
HETATM   12  C10 UNL     1      -1.750   1.407   0.638  1.00  0.00           C  
HETATM   13  C11 UNL     1      -2.950   1.071  -0.192  1.00  0.00           C  
HETATM   14  C12 UNL     1      -3.177  -0.407  -0.235  1.00  0.00           C  
HETATM   15  C13 UNL     1      -4.320  -0.892   0.224  1.00  0.00           C  
HETATM   16  C14 UNL     1      -5.371   0.000   0.777  1.00  0.00           C  
HETATM   17  C15 UNL     1      -4.572  -2.356   0.192  1.00  0.00           C  
HETATM   18  H1  UNL     1       5.877  -0.585   1.845  1.00  0.00           H  
HETATM   19  H2  UNL     1       5.969  -2.360   1.698  1.00  0.00           H  
HETATM   20  H3  UNL     1       6.570  -1.252   0.354  1.00  0.00           H  
HETATM   21  H4  UNL     1       3.742  -2.204   0.832  1.00  0.00           H  
HETATM   22  H5  UNL     1       4.773   1.436   0.166  1.00  0.00           H  
HETATM   23  H6  UNL     1       5.904   0.348  -0.808  1.00  0.00           H  
HETATM   24  H7  UNL     1       4.459   1.090  -1.556  1.00  0.00           H  
HETATM   25  H8  UNL     1       0.468  -0.514  -2.386  1.00  0.00           H  
HETATM   26  H9  UNL     1       0.839   1.135  -3.079  1.00  0.00           H  
HETATM   27  H10 UNL     1      -1.172   1.257  -1.898  1.00  0.00           H  
HETATM   28  H11 UNL     1       0.010   2.322  -1.172  1.00  0.00           H  
HETATM   29  H12 UNL     1      -0.666  -0.399   0.127  1.00  0.00           H  
HETATM   30  H13 UNL     1       0.182   1.620   1.913  1.00  0.00           H  
HETATM   31  H14 UNL     1       0.969   0.050   1.572  1.00  0.00           H  
HETATM   32  H15 UNL     1       1.439   1.581   0.668  1.00  0.00           H  
HETATM   33  H16 UNL     1      -1.921   1.078   1.706  1.00  0.00           H  
HETATM   34  H17 UNL     1      -1.602   2.512   0.736  1.00  0.00           H  
HETATM   35  H18 UNL     1      -3.818   1.569   0.333  1.00  0.00           H  
HETATM   36  H19 UNL     1      -2.946   1.448  -1.221  1.00  0.00           H  
HETATM   37  H20 UNL     1      -2.429  -1.079  -0.633  1.00  0.00           H  
HETATM   38  H21 UNL     1      -4.998   0.582   1.670  1.00  0.00           H  
HETATM   39  H22 UNL     1      -5.672   0.780   0.024  1.00  0.00           H  
HETATM   40  H23 UNL     1      -6.239  -0.566   1.142  1.00  0.00           H  
HETATM   41  H24 UNL     1      -5.540  -2.557  -0.311  1.00  0.00           H  
HETATM   42  H25 UNL     1      -4.586  -2.793   1.231  1.00  0.00           H  
HETATM   43  H26 UNL     1      -3.801  -2.905  -0.367  1.00  0.00           H  
CONECT    1    2   18   19   20
CONECT    2    3    3   21
CONECT    3    4    5
CONECT    4   22   23   24
CONECT    5    6    6    7
CONECT    7    8
CONECT    8    9   25   26
CONECT    9   10   27   28
CONECT   10   11   12   29
CONECT   11   30   31   32
CONECT   12   13   33   34
CONECT   13   14   35   36
CONECT   14   15   15   37
CONECT   15   16   17
CONECT   16   38   39   40
CONECT   17   41   42   43
END

HMDB0032209
     RDKit          3D
Citronellyl trans-2-methyl-2-butenoate
 43 42  0  0  0  0  0  0  0  0999 V2000
    5.7933   -1.4423    1.1267 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4274   -1.4097    0.5725 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9838   -0.4706   -0.2233 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8682    0.6334   -0.6105 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5939   -0.5243   -0.7299 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8284   -1.4686   -0.4023 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.0974    0.4516   -1.5706 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.8324    0.5519   -2.0927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2100    1.1782   -1.2618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5024    0.7403    0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6152    0.9588    1.1018 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7504    1.4069    0.6384 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9496    1.0709   -0.1917 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1774   -0.4073   -0.2353 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3202   -0.8924    0.2238 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3709    0.0004    0.7768 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5719   -2.3563    0.1920 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8770   -0.5846    1.8449 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9689   -2.3597    1.6980 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5698   -1.2516    0.3542 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7418   -2.2041    0.8321 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7733    1.4362    0.1663 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9042    0.3484   -0.8084 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4592    1.0897   -1.5557 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4676   -0.5136   -2.3858 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8385    1.1348   -3.0788 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1718    1.2571   -1.8976 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0101    2.3223   -1.1717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6662   -0.3993    0.1269 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1824    1.6204    1.9131 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9695    0.0496    1.5716 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4388    1.5811    0.6682 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9205    1.0779    1.7063 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6015    2.5120    0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8179    1.5690    0.3326 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9460    1.4481   -1.2206 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4288   -1.0786   -0.6331 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9983    0.5819    1.6699 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6724    0.7800    0.0240 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2386   -0.5657    1.1419 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5400   -2.5575   -0.3107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5856   -2.7933    1.2312 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8008   -2.9052   -0.3669 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
  3  5  1  0
  5  6  2  0
  5  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 10 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  2  3
 15 16  1  0
 15 17  1  0
  1 18  1  0
  1 19  1  0
  1 20  1  0
  2 21  1  0
  4 22  1  0
  4 23  1  0
  4 24  1  0
  8 25  1  0
  8 26  1  0
  9 27  1  0
  9 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 11 32  1  0
 12 33  1  0
 12 34  1  0
 13 35  1  0
 13 36  1  0
 14 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
 17 41  1  0
 17 42  1  0
 17 43  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Citronellyl trans-2-methyl-2-butenoic acid	Generator
3,7-Dimethyl-6-octenyl (2Z)-2-methyl-2-butenoate	HMDB
3,7-Dimethyl-6-octenyl 2-methylcrotonate	HMDB
Citronellyl tiglate	HMDB
e-Citronellyl tiglate	HMDB

Chemical Formula

C₁₅H₂₆O₂

Average Molecular Weight

238.3657

Monoisotopic Molecular Weight

238.193280076

IUPAC Name

3,7-dimethyloct-6-en-1-yl (2E)-2-methylbut-2-enoate

Traditional Name

3,7-dimethyloct-6-en-1-yl (2E)-2-methylbut-2-enoate

CAS Registry Number

24717-85-9

SMILES

C\C=C(/C)C(=O)OCCC(C)CCC=C(C)C

InChI Identifier

InChI=1S/C15H26O2/c1-6-14(5)15(16)17-11-10-13(4)9-7-8-12(2)3/h6,8,13H,7,9-11H2,1-5H3/b14-6+

InChI Key

UCFQYMKLDPWFHZ-MKMNVTDBSA-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
Fatty acid ester
Alpha,beta-unsaturated carboxylic ester
Enoate ester
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

Cytoplasm (HMDB: HMDB0032209)
Cell membrane (HMDB: HMDB0032209)

Biofluid or Excreta

Urine (HMDB: HMDB0032209)

Cellular substructure

Extracellular (HMDB: HMDB0032209)
Membrane (HMDB: HMDB0032209)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0032209)

Source

Endogenous

Endogenous (HMDB: HMDB0032209)

Animal

Animal (HMDB: HMDB0032209)

Exogenous

Food

Food (HMDB: HMDB0032209)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0032209)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0032209)

Cellular process

Cell signaling (HMDB: HMDB0032209)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0032209)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0032209)

Nutrient

Nutrient (HMDB: HMDB0032209)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0032209)

Emulsifier (HMDB: HMDB0032209)

Physical Properties

State

Not Available

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.018 g/L	ALOGPS
logP	5.36	ALOGPS
logP	4.96	ChemAxon
logS	-4.1	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	8	ChemAxon
Refractivity	74.32 m³·mol⁻¹	ChemAxon
Polarizability	29.83 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]+	159.587	31661259
DarkChem	[M-H]-	158.281	31661259
DeepCCS	[M+H]+	164.235	30932474
DeepCCS	[M-H]-	161.877	30932474
DeepCCS	[M-2H]-	194.857	30932474
DeepCCS	[M+Na]+	170.329	30932474
AllCCS	[M+H]+	162.2	32859911
AllCCS	[M+H-H2O]+	158.9	32859911
AllCCS	[M+NH4]+	165.3	32859911
AllCCS	[M+Na]+	166.2	32859911
AllCCS	[M-H]-	164.3	32859911
AllCCS	[M+Na-2H]-	165.3	32859911
AllCCS	[M+HCOO]-	166.6	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citronellyl trans-2-methyl-2-butenoate	C\C=C(/C)C(=O)OCCC(C)CCC=C(C)C	1945.5	Standard polar	33892256
Citronellyl trans-2-methyl-2-butenoate	C\C=C(/C)C(=O)OCCC(C)CCC=C(C)C	1619.0	Standard non polar	33892256
Citronellyl trans-2-methyl-2-butenoate	C\C=C(/C)C(=O)OCCC(C)CCC=C(C)C	1623.3	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Citronellyl trans-2-methyl-2-butenoate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0bu0-9710000000-6d99a21facc6a4c402e8	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citronellyl trans-2-methyl-2-butenoate 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 trans-2-methyl-2-butenoate 10V, Positive-QTOF	splash10-000i-5690000000-413387ba49788a191622	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl trans-2-methyl-2-butenoate 20V, Positive-QTOF	splash10-053i-9410000000-201d966e343c0afd10f8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl trans-2-methyl-2-butenoate 40V, Positive-QTOF	splash10-0pw9-9000000000-01f55b7390bf35f02d55	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl trans-2-methyl-2-butenoate 10V, Negative-QTOF	splash10-000i-3290000000-177c5ecfc428e7ae8bb6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl trans-2-methyl-2-butenoate 20V, Negative-QTOF	splash10-0002-9110000000-78092628c059ad9ea1c3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl trans-2-methyl-2-butenoate 40V, Negative-QTOF	splash10-0aba-9200000000-ac690f68d08cbae4e66e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl trans-2-methyl-2-butenoate 10V, Negative-QTOF	splash10-0002-9130000000-034c9458cd1dec16e53c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl trans-2-methyl-2-butenoate 20V, Negative-QTOF	splash10-0002-9000000000-436e501ee3e1529c1bc3	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl trans-2-methyl-2-butenoate 40V, Negative-QTOF	splash10-0pb9-9000000000-3e41fae386b53a8b526d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl trans-2-methyl-2-butenoate 10V, Positive-QTOF	splash10-001r-9620000000-c4e25ec6181d7e92067d	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl trans-2-methyl-2-butenoate 20V, Positive-QTOF	splash10-053r-9100000000-a04ff32b8f158fe180f2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl trans-2-methyl-2-butenoate 40V, Positive-QTOF	splash10-0api-9000000000-a64314644e4ffb783e50	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB009194

KNApSAcK ID

Not Available

Chemspider ID

4905187

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6386037

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). EAFUS: Everything Added to Food in the United States.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Citronellyl trans-2-methyl-2-butenoate (HMDB0032209)

MOL for HMDB0032209 (Citronellyl trans-2-methyl-2-butenoate)

3D MOL for HMDB0032209 (Citronellyl trans-2-methyl-2-butenoate)

3D SDF for HMDB0032209 (Citronellyl trans-2-methyl-2-butenoate)

3D-SDF for HMDB0032209 (Citronellyl trans-2-methyl-2-butenoate)

PDB for HMDB0032209 (Citronellyl trans-2-methyl-2-butenoate)

3D PDB for HMDB0032209 (Citronellyl trans-2-methyl-2-butenoate)

SMILES for HMDB0032209 (Citronellyl trans-2-methyl-2-butenoate)

INCHI for HMDB0032209 (Citronellyl trans-2-methyl-2-butenoate)

Structure for HMDB0032209 (Citronellyl trans-2-methyl-2-butenoate)

3D Structure for HMDB0032209 (Citronellyl trans-2-methyl-2-butenoate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra