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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-12 00:18:14 UTC

Update Date

2022-03-07 02:56:00 UTC

HMDB ID

HMDB0038957

Secondary Accession Numbers

HMDB38957

Metabolite Identification

Common Name

Citronellyl cinnamate

Description

Citronellyl cinnamate 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 cinnamate.

Structure

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

HMDB0038957
     RDKit          3D
Citronellyl cinnamate
 47 47  0  0  0  0  0  0  0  0999 V2000
   -6.2267   -1.2521   -2.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3143   -0.7096   -1.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7538    0.5909   -0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3299   -1.4771   -0.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3031   -1.2880    0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2645    0.0378    0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1810    0.1487    1.7381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2661    1.5559    2.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205   -0.1732    1.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2224   -0.0540    2.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5186   -0.3386    1.8614 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2283    0.3230    0.8742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471    1.2742    0.3000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5790   -0.0297    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1848    0.6476   -0.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5158    0.4017   -0.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3290   -0.5927   -0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6262   -0.8042   -0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1231   -0.0122   -1.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3215    0.9878   -2.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0505    1.1857   -1.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6184   -0.4032   -3.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6119   -1.9101   -3.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0416   -1.7927   -1.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5968    0.9567   -1.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0166    1.3985   -0.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2684    0.5338    0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869   -2.4509   -1.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3942   -2.0874    0.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3247   -1.5589   -0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1964    0.2821    1.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9903    0.8172   -0.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4062   -0.5451    2.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6809    2.2781    1.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0324    1.5923    3.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3359    1.8965    2.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5223    0.4217    0.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8400   -1.2548    0.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1086    0.9547    2.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0151   -0.7707    3.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0843   -0.8465    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6138    1.4680   -0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9509   -1.2307    0.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2230   -1.5833   -0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1313   -0.1920   -2.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7239    1.6057   -3.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4572    1.9992   -2.3821 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  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 14 41  1  0
 15 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
M  END

  Mrv0541 05061310452D          

 21 21  0  0  0  0            999 V2000
    6.4302    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    0.4125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    2.8875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7184    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0039    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5749    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8605    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    2.4750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.2894    1.6500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    1.2375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1460    0.4125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   11.4315    1.6500    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  5  4  2  0  0  0  0
  6  4  1  0  0  0  0
  8  7  1  0  0  0  0
  9  7  1  0  0  0  0
 10  5  1  0  0  0  0
 11  6  2  0  0  0  0
 13 12  2  0  0  0  0
 15 14  1  0  0  0  0
 16  1  1  0  0  0  0
 16  2  1  0  0  0  0
 16  8  2  0  0  0  0
 17  3  1  0  0  0  0
 17  9  1  0  0  0  0
 17 14  1  0  0  0  0
 18 10  2  0  0  0  0
 18 11  1  0  0  0  0
 18 12  1  0  0  0  0
 19 13  1  0  0  0  0
 20 19  2  0  0  0  0
 21 15  1  0  0  0  0
 21 19  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038957

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CCOC(=O)\C=C\C1=CC=CC=C1)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C19H26O2/c1-16(2)8-7-9-17(3)14-15-21-19(20)13-12-18-10-5-4-6-11-18/h4-6,8,10-13,17H,7,9,14-15H2,1-3H3/b13-12+

> <INCHI_KEY>
KMXKQELDKDGFRN-OUKQBFOZSA-N

> <FORMULA>
C19H26O2

> <MOLECULAR_WEIGHT>
286.4085

> <EXACT_MASS>
286.193280076

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
34.98308205961775

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

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

> <ALOGPS_LOGP>
5.74

> <JCHEM_LOGP>
5.785946035333333

> <ALOGPS_LOGS>
-5.39

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-6.808969809053324

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
90.05379999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.16e-03 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0038957
     RDKit          3D
Citronellyl cinnamate
 47 47  0  0  0  0  0  0  0  0999 V2000
   -6.2267   -1.2521   -2.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3143   -0.7096   -1.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7538    0.5909   -0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3299   -1.4771   -0.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3031   -1.2880    0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2645    0.0378    0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1810    0.1487    1.7381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2661    1.5559    2.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205   -0.1732    1.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2224   -0.0540    2.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5186   -0.3386    1.8614 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2283    0.3230    0.8742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471    1.2742    0.3000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5790   -0.0297    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1848    0.6476   -0.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5158    0.4017   -0.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3290   -0.5927   -0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6262   -0.8042   -0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1231   -0.0122   -1.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3215    0.9878   -2.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0505    1.1857   -1.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6184   -0.4032   -3.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6119   -1.9101   -3.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0416   -1.7927   -1.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5968    0.9567   -1.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0166    1.3985   -0.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2684    0.5338    0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869   -2.4509   -1.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3942   -2.0874    0.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3247   -1.5589   -0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1964    0.2821    1.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9903    0.8172   -0.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4062   -0.5451    2.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6809    2.2781    1.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0324    1.5923    3.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3359    1.8965    2.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5223    0.4217    0.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8400   -1.2548    0.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1086    0.9547    2.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0151   -0.7707    3.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0843   -0.8465    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6138    1.4680   -0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9509   -1.2307    0.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2230   -1.5833   -0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1313   -0.1920   -2.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7239    1.6057   -3.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4572    1.9992   -2.3821 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  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 14 41  1  0
 15 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  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      12.003   5.390   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      14.671   5.390   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      17.338   0.770   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      29.341   4.620   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.007   5.390   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      29.341   3.080   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      14.671   2.310   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      13.337   3.080   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      16.004   3.080   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      26.674   4.620   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.007   2.310   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.340   2.310   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.006   3.080   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      18.672   3.080   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      20.005   2.310   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.337   4.620   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.338   2.310   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      26.674   3.080   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      22.673   2.310   0.000  0.00  0.00           C+0
HETATM   20  O   UNK     0      22.673   0.770   0.000  0.00  0.00           O+0
HETATM   21  O   UNK     0      21.339   3.080   0.000  0.00  0.00           O+0
CONECT    1   16                                                            
CONECT    2   16                                                            
CONECT    3   17                                                            
CONECT    4    5    6                                                       
CONECT    5    4   10                                                       
CONECT    6    4   11                                                       
CONECT    7    8    9                                                       
CONECT    8    7   16                                                       
CONECT    9    7   17                                                       
CONECT   10    5   18                                                       
CONECT   11    6   18                                                       
CONECT   12   13   18                                                       
CONECT   13   12   19                                                       
CONECT   14   15   17                                                       
CONECT   15   14   21                                                       
CONECT   16    1    2    8                                                  
CONECT   17    3    9   14                                                  
CONECT   18   10   11   12                                                  
CONECT   19   13   20   21                                                  
CONECT   20   19                                                            
CONECT   21   15   19                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   42    0
END

COMPND    HMDB0038957
HETATM    1  C1  UNL     1      -6.227  -1.252  -2.451  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.314  -0.710  -1.314  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.754   0.591  -0.800  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.330  -1.477  -0.970  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.303  -1.288   0.031  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.265   0.038   0.661  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.181   0.149   1.738  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.266   1.556   2.288  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.821  -0.173   1.201  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.222  -0.054   2.281  1.00  0.00           C  
HETATM   11  O1  UNL     1       1.519  -0.339   1.861  1.00  0.00           O  
HETATM   12  C11 UNL     1       2.228   0.323   0.874  1.00  0.00           C  
HETATM   13  O2  UNL     1       1.647   1.274   0.300  1.00  0.00           O  
HETATM   14  C12 UNL     1       3.579  -0.030   0.488  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.185   0.648  -0.459  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.516   0.402  -0.934  1.00  0.00           C  
HETATM   17  C15 UNL     1       6.329  -0.593  -0.442  1.00  0.00           C  
HETATM   18  C16 UNL     1       7.626  -0.804  -0.931  1.00  0.00           C  
HETATM   19  C17 UNL     1       8.123  -0.012  -1.927  1.00  0.00           C  
HETATM   20  C18 UNL     1       7.322   0.988  -2.429  1.00  0.00           C  
HETATM   21  C19 UNL     1       6.051   1.186  -1.942  1.00  0.00           C  
HETATM   22  H1  UNL     1      -6.618  -0.403  -3.037  1.00  0.00           H  
HETATM   23  H2  UNL     1      -5.612  -1.910  -3.073  1.00  0.00           H  
HETATM   24  H3  UNL     1      -7.042  -1.793  -1.934  1.00  0.00           H  
HETATM   25  H4  UNL     1      -6.597   0.957  -1.487  1.00  0.00           H  
HETATM   26  H5  UNL     1      -5.017   1.398  -0.784  1.00  0.00           H  
HETATM   27  H6  UNL     1      -6.268   0.534   0.197  1.00  0.00           H  
HETATM   28  H7  UNL     1      -4.287  -2.451  -1.564  1.00  0.00           H  
HETATM   29  H8  UNL     1      -3.394  -2.087   0.836  1.00  0.00           H  
HETATM   30  H9  UNL     1      -2.325  -1.559  -0.472  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.196   0.282   1.163  1.00  0.00           H  
HETATM   32  H11 UNL     1      -2.990   0.817  -0.087  1.00  0.00           H  
HETATM   33  H12 UNL     1      -2.406  -0.545   2.573  1.00  0.00           H  
HETATM   34  H13 UNL     1      -1.681   2.278   1.704  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.032   1.592   3.377  1.00  0.00           H  
HETATM   36  H15 UNL     1      -3.336   1.897   2.211  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.522   0.422   0.341  1.00  0.00           H  
HETATM   38  H17 UNL     1      -0.840  -1.255   0.881  1.00  0.00           H  
HETATM   39  H18 UNL     1       0.109   0.955   2.729  1.00  0.00           H  
HETATM   40  H19 UNL     1      -0.015  -0.771   3.111  1.00  0.00           H  
HETATM   41  H20 UNL     1       4.084  -0.846   0.978  1.00  0.00           H  
HETATM   42  H21 UNL     1       3.614   1.468  -0.917  1.00  0.00           H  
HETATM   43  H22 UNL     1       5.951  -1.231   0.348  1.00  0.00           H  
HETATM   44  H23 UNL     1       8.223  -1.583  -0.525  1.00  0.00           H  
HETATM   45  H24 UNL     1       9.131  -0.192  -2.292  1.00  0.00           H  
HETATM   46  H25 UNL     1       7.724   1.606  -3.214  1.00  0.00           H  
HETATM   47  H26 UNL     1       5.457   1.999  -2.382  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3    4    4
CONECT    3   25   26   27
CONECT    4    5   28
CONECT    5    6   29   30
CONECT    6    7   31   32
CONECT    7    8    9   33
CONECT    8   34   35   36
CONECT    9   10   37   38
CONECT   10   11   39   40
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   15   41
CONECT   15   16   42
CONECT   16   17   17   21
CONECT   17   18   43
CONECT   18   19   19   44
CONECT   19   20   45
CONECT   20   21   21   46
CONECT   21   47
END

HMDB0038957
     RDKit          3D
Citronellyl cinnamate
 47 47  0  0  0  0  0  0  0  0999 V2000
   -6.2267   -1.2521   -2.4509 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3143   -0.7096   -1.3144 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7538    0.5909   -0.7998 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3299   -1.4771   -0.9695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3031   -1.2880    0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2645    0.0378    0.6612 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1810    0.1487    1.7381 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2661    1.5559    2.2880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8205   -0.1732    1.2011 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2224   -0.0540    2.2813 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5186   -0.3386    1.8614 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.2283    0.3230    0.8742 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6471    1.2742    0.3000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.5790   -0.0297    0.4879 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1848    0.6476   -0.4590 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5158    0.4017   -0.9338 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3290   -0.5927   -0.4423 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6262   -0.8042   -0.9310 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1231   -0.0122   -1.9266 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3215    0.9878   -2.4295 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0505    1.1857   -1.9419 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6184   -0.4032   -3.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6119   -1.9101   -3.0733 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0416   -1.7927   -1.9340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5968    0.9567   -1.4872 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0166    1.3985   -0.7840 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2684    0.5338    0.1974 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2869   -2.4509   -1.5636 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3942   -2.0874    0.8359 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3247   -1.5589   -0.4719 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1964    0.2821    1.1627 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9903    0.8172   -0.0869 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4062   -0.5451    2.5728 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6809    2.2781    1.7035 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0324    1.5923    3.3773 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3359    1.8965    2.2107 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5223    0.4217    0.3411 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8400   -1.2548    0.8805 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1086    0.9547    2.7294 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0151   -0.7707    3.1113 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0843   -0.8465    0.9776 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6138    1.4680   -0.9174 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9509   -1.2307    0.3480 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.2230   -1.5833   -0.5246 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.1313   -0.1920   -2.2922 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7239    1.6057   -3.2139 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4572    1.9992   -2.3821 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  2  0
 15 16  1  0
 16 17  2  0
 17 18  1  0
 18 19  2  0
 19 20  1  0
 20 21  2  0
 21 16  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  3 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  5 29  1  0
  5 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  8 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 14 41  1  0
 15 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
 21 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Citronellyl cinnamic acid	Generator
2-Propenoic acid, 3-phenyl-, 3,7-dimethyl-6-octenyl ester	HMDB

Chemical Formula

C₁₉H₂₆O₂

Average Molecular Weight

286.4085

Monoisotopic Molecular Weight

286.193280076

IUPAC Name

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

Traditional Name

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

CAS Registry Number

10482-79-8

SMILES

CC(CCOC(=O)\C=C\C1=CC=CC=C1)CCC=C(C)C

InChI Identifier

InChI=1S/C19H26O2/c1-16(2)8-7-9-17(3)14-15-21-19(20)13-12-18-10-5-4-6-11-18/h4-6,8,10-13,17H,7,9,14-15H2,1-3H3/b13-12+

InChI Key

KMXKQELDKDGFRN-OUKQBFOZSA-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

Cinnamic acid or derivatives
Fatty alcohol ester
Cinnamic acid ester
Aromatic monoterpenoid
Monocyclic monoterpenoid
Monoterpenoid
Styrene
Fatty acid ester
Monocyclic benzene moiety
Benzenoid
Alpha,beta-unsaturated carboxylic ester
Enoate ester
Carboxylic acid ester
Carboxylic acid derivative
Monocarboxylic acid or derivatives
Organic oxygen compound
Hydrocarbon derivative
Carbonyl group
Organic oxide
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

Not Available

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Excreta

Biofluid or Excreta

Urine (HMDB: HMDB0038957)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0038957)

Source

Endogenous

Endogenous (HMDB: HMDB0038957)

Animal

Animal (HMDB: HMDB0038957)

Exogenous

Food

Food (HMDB: HMDB0038957)

Exogenous (HMDB: HMDB0038957)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0038957)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0038957)

Lipid metabolism pathway (HMDB: HMDB0038957)

Cellular process

Cell signaling (HMDB: HMDB0038957)

Biochemical process

Lipid transport (HMDB: HMDB0038957)

Role

Biological role

Energy source (HMDB: HMDB0038957)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0038957)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	380.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.038 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	6.387 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0012 g/L	ALOGPS
logP	5.74	ALOGPS
logP	5.79	ChemAxon
logS	-5.4	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	9	ChemAxon
Refractivity	90.05 m³·mol⁻¹	ChemAxon
Polarizability	34.98 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	173.624	31661259
DarkChem	[M-H]-	170.825	31661259
DeepCCS	[M+H]+	171.359	30932474
DeepCCS	[M-H]-	169.001	30932474
DeepCCS	[M-2H]-	201.887	30932474
DeepCCS	[M+Na]+	177.453	30932474
AllCCS	[M+H]+	173.1	32859911
AllCCS	[M+H-H2O]+	170.0	32859911
AllCCS	[M+NH4]+	176.0	32859911
AllCCS	[M+Na]+	176.8	32859911
AllCCS	[M-H]-	177.4	32859911
AllCCS	[M+Na-2H]-	177.7	32859911
AllCCS	[M+HCOO]-	178.2	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citronellyl cinnamate	CC(CCOC(=O)\C=C\C1=CC=CC=C1)CCC=C(C)C	2766.7	Standard polar	33892256
Citronellyl cinnamate	CC(CCOC(=O)\C=C\C1=CC=CC=C1)CCC=C(C)C	2122.8	Standard non polar	33892256
Citronellyl cinnamate	CC(CCOC(=O)\C=C\C1=CC=CC=C1)CCC=C(C)C	2214.2	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 cinnamate GC-MS (Non-derivatized) - 70eV, Positive	splash10-001i-4900000000-76f7f61f5d8383f44f4f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citronellyl cinnamate 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 cinnamate 10V, Positive-QTOF	splash10-000i-1790000000-f1e80207f949ca278efa	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl cinnamate 20V, Positive-QTOF	splash10-001r-4910000000-da65e0872d1a93042c35	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl cinnamate 40V, Positive-QTOF	splash10-0ldl-9400000000-0f4f0594372193d97fb8	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl cinnamate 10V, Negative-QTOF	splash10-002r-0960000000-5a09328aafbbf46029b4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl cinnamate 20V, Negative-QTOF	splash10-002k-0900000000-ebfaf5ba0364e2bc4367	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl cinnamate 40V, Negative-QTOF	splash10-004i-1900000000-9afcacdd72c5a3971b6c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl cinnamate 10V, Positive-QTOF	splash10-0019-3890000000-efb19010187fd305c288	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl cinnamate 20V, Positive-QTOF	splash10-001i-6910000000-867c0e6fc529edef32da	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl cinnamate 40V, Positive-QTOF	splash10-0ue9-8900000000-b40d6f4e32ea5027cfc5	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl cinnamate 10V, Negative-QTOF	splash10-000i-0090000000-0f24c1e7ed8a9b47b39f	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl cinnamate 20V, Negative-QTOF	splash10-0udi-2930000000-7c0274468614b4bc53fc	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl cinnamate 40V, Negative-QTOF	splash10-0ufr-7900000000-5efa528297e2e857c438	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

FDB018440

KNApSAcK ID

Not Available

Chemspider ID

4942248

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

6437720

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1015801

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 ]
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Showing metabocard for Citronellyl cinnamate (HMDB0038957)

MOL for HMDB0038957 (Citronellyl cinnamate)

3D MOL for HMDB0038957 (Citronellyl cinnamate)

3D SDF for HMDB0038957 (Citronellyl cinnamate)

3D-SDF for HMDB0038957 (Citronellyl cinnamate)

PDB for HMDB0038957 (Citronellyl cinnamate)

3D PDB for HMDB0038957 (Citronellyl cinnamate)

SMILES for HMDB0038957 (Citronellyl cinnamate)

INCHI for HMDB0038957 (Citronellyl cinnamate)

Structure for HMDB0038957 (Citronellyl cinnamate)

3D Structure for HMDB0038957 (Citronellyl cinnamate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra