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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 22:28:18 UTC

Update Date

2022-03-07 02:55:14 UTC

HMDB ID

HMDB0037230

Secondary Accession Numbers

HMDB37230

Metabolite Identification

Common Name

Citronellyl alpha-toluate

Description

Citronellyl alpha-toluate, also known as citronellyl a-toluic acid, 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 alpha-toluate.

Structure

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

HMDB0037230
     RDKit          3D
Citronellyl alpha-toluate
 46 46  0  0  0  0  0  0  0  0999 V2000
   -7.0248   -1.0235   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8024   -0.1705   -0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8472    1.2774   -0.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6723   -0.7133    0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4524    0.1366    0.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3727   -0.2902   -0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1380    0.6017   -0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5507    0.5429    1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592    0.2410   -1.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758    1.0651   -1.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8986    0.9725   -0.2958 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603   -0.1671    0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4312   -1.2133   -0.5630 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4258   -0.1905    1.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8204   -0.3663    0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3797   -1.6024    0.5751 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6621   -1.7152    0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4294   -0.6093   -0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8480    0.6290   -0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5746    0.7540    0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3966   -1.2534    0.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7009   -1.9395   -0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8049   -0.4695   -0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7018    1.8887    0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8125    1.5556   -0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0612    1.5624   -1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6415   -1.7681    0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7512    1.1847    0.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1311    0.0147    1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1221   -1.3549   -0.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7543   -0.1475   -1.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5131    1.6534   -0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0572   -0.4629    1.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3152    0.6920    1.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2497    1.3095    1.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6777    0.2556   -2.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410   -0.8470   -1.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8244    2.1722   -1.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6326    0.7917   -2.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3620    0.7227    1.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2130   -1.0622    1.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8177   -2.5112    0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0986   -2.7011   -0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4400   -0.6837   -0.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4411    1.5073   -0.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1346    1.7317    0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
M  END

  Mrv0541 05061309392D          

 20 20  0  0  0  0            999 V2000
    2.1434    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    6.1875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7171    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    3.3000    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5724    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2868    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0026    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    3.7125    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7158    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4302    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5737    4.9500    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8579    5.7750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0013    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2881    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    4.5375    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8592    3.7125    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.1447    4.9500    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  1  0  0  0  0
 15  1  1  0  0  0  0
 15  2  1  0  0  0  0
 15  8  2  0  0  0  0
 16  3  1  0  0  0  0
 16  9  1  0  0  0  0
 16 12  1  0  0  0  0
 17 10  2  0  0  0  0
 17 11  1  0  0  0  0
 17 14  1  0  0  0  0
 18 14  1  0  0  0  0
 19 18  2  0  0  0  0
 20 13  1  0  0  0  0
 20 18  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0037230

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(CCOC(=O)CC1=CC=CC=C1)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C18H26O2/c1-15(2)8-7-9-16(3)12-13-20-18(19)14-17-10-5-4-6-11-17/h4-6,8,10-11,16H,7,9,12-14H2,1-3H3

> <INCHI_KEY>
CVJBFMVLVJZZMM-UHFFFAOYSA-N

> <FORMULA>
C18H26O2

> <MOLECULAR_WEIGHT>
274.3978

> <EXACT_MASS>
274.193280076

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
33.36195251020977

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
5.76

> <JCHEM_LOGP>
5.027520547333332

> <ALOGPS_LOGS>
-5.15

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.086224916693465

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
84.3595

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
1.94e-03 g/l

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

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0037230
     RDKit          3D
Citronellyl alpha-toluate
 46 46  0  0  0  0  0  0  0  0999 V2000
   -7.0248   -1.0235   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8024   -0.1705   -0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8472    1.2774   -0.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6723   -0.7133    0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4524    0.1366    0.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3727   -0.2902   -0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1380    0.6017   -0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5507    0.5429    1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592    0.2410   -1.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758    1.0651   -1.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8986    0.9725   -0.2958 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603   -0.1671    0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4312   -1.2133   -0.5630 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4258   -0.1905    1.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8204   -0.3663    0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3797   -1.6024    0.5751 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6621   -1.7152    0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4294   -0.6093   -0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8480    0.6290   -0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5746    0.7540    0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3966   -1.2534    0.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7009   -1.9395   -0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8049   -0.4695   -0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7018    1.8887    0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8125    1.5556   -0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0612    1.5624   -1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6415   -1.7681    0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7512    1.1847    0.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1311    0.0147    1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1221   -1.3549   -0.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7543   -0.1475   -1.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5131    1.6534   -0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0572   -0.4629    1.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3152    0.6920    1.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2497    1.3095    1.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6777    0.2556   -2.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410   -0.8470   -1.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8244    2.1722   -1.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6326    0.7917   -2.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3620    0.7227    1.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2130   -1.0622    1.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8177   -2.5112    0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0986   -2.7011   -0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4400   -0.6837   -0.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4411    1.5073   -0.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1346    1.7317    0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  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       4.001  11.550   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       6.668  11.550   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       9.336   6.930   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      20.005   6.930   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      20.005   8.470   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.672   6.160   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       6.668   8.470   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.335   9.240   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       8.002   9.240   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      18.672   9.240   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      17.338   6.930   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      10.669   9.240   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      12.003   8.470   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      16.004   9.240   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       5.335  10.780   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       9.336   8.470   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      17.338   8.470   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.671   8.470   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      14.671   6.930   0.000  0.00  0.00           O+0
HETATM   20  O   UNK     0      13.337   9.240   0.000  0.00  0.00           O+0
CONECT    1   15                                                            
CONECT    2   15                                                            
CONECT    3   16                                                            
CONECT    4    5    6                                                       
CONECT    5    4   10                                                       
CONECT    6    4   11                                                       
CONECT    7    8    9                                                       
CONECT    8    7   15                                                       
CONECT    9    7   16                                                       
CONECT   10    5   17                                                       
CONECT   11    6   17                                                       
CONECT   12   13   16                                                       
CONECT   13   12   20                                                       
CONECT   14   17   18                                                       
CONECT   15    1    2    8                                                  
CONECT   16    3    9   12                                                  
CONECT   17   10   11   14                                                  
CONECT   18   14   19   20                                                  
CONECT   19   18                                                            
CONECT   20   13   18                                                       
MASTER        0    0    0    0    0    0    0    0   20    0   40    0
END

COMPND    HMDB0037230
HETATM    1  C1  UNL     1      -7.025  -1.024  -0.172  1.00  0.00           C  
HETATM    2  C2  UNL     1      -5.802  -0.170  -0.031  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.847   1.277  -0.342  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.672  -0.713   0.364  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.452   0.137   0.507  1.00  0.00           C  
HETATM    6  C6  UNL     1      -2.373  -0.290  -0.439  1.00  0.00           C  
HETATM    7  C7  UNL     1      -1.138   0.602  -0.325  1.00  0.00           C  
HETATM    8  C8  UNL     1      -0.551   0.543   1.041  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.159   0.241  -1.398  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.076   1.065  -1.415  1.00  0.00           C  
HETATM   11  O1  UNL     1       1.899   0.973  -0.296  1.00  0.00           O  
HETATM   12  C11 UNL     1       2.560  -0.167   0.106  1.00  0.00           C  
HETATM   13  O2  UNL     1       2.431  -1.213  -0.563  1.00  0.00           O  
HETATM   14  C12 UNL     1       3.426  -0.191   1.305  1.00  0.00           C  
HETATM   15  C13 UNL     1       4.820  -0.366   0.773  1.00  0.00           C  
HETATM   16  C14 UNL     1       5.380  -1.602   0.575  1.00  0.00           C  
HETATM   17  C15 UNL     1       6.662  -1.715   0.065  1.00  0.00           C  
HETATM   18  C16 UNL     1       7.429  -0.609  -0.264  1.00  0.00           C  
HETATM   19  C17 UNL     1       6.848   0.629  -0.057  1.00  0.00           C  
HETATM   20  C18 UNL     1       5.575   0.754   0.450  1.00  0.00           C  
HETATM   21  H1  UNL     1      -7.397  -1.253   0.844  1.00  0.00           H  
HETATM   22  H2  UNL     1      -6.701  -1.940  -0.727  1.00  0.00           H  
HETATM   23  H3  UNL     1      -7.805  -0.469  -0.753  1.00  0.00           H  
HETATM   24  H4  UNL     1      -5.702   1.889   0.551  1.00  0.00           H  
HETATM   25  H5  UNL     1      -6.813   1.556  -0.825  1.00  0.00           H  
HETATM   26  H6  UNL     1      -5.061   1.562  -1.100  1.00  0.00           H  
HETATM   27  H7  UNL     1      -4.641  -1.768   0.582  1.00  0.00           H  
HETATM   28  H8  UNL     1      -3.751   1.185   0.393  1.00  0.00           H  
HETATM   29  H9  UNL     1      -3.131   0.015   1.575  1.00  0.00           H  
HETATM   30  H10 UNL     1      -2.122  -1.355  -0.331  1.00  0.00           H  
HETATM   31  H11 UNL     1      -2.754  -0.148  -1.469  1.00  0.00           H  
HETATM   32  H12 UNL     1      -1.513   1.653  -0.525  1.00  0.00           H  
HETATM   33  H13 UNL     1      -0.057  -0.463   1.165  1.00  0.00           H  
HETATM   34  H14 UNL     1      -1.315   0.692   1.846  1.00  0.00           H  
HETATM   35  H15 UNL     1       0.250   1.309   1.136  1.00  0.00           H  
HETATM   36  H16 UNL     1      -0.678   0.256  -2.406  1.00  0.00           H  
HETATM   37  H17 UNL     1       0.141  -0.847  -1.307  1.00  0.00           H  
HETATM   38  H18 UNL     1       0.824   2.172  -1.516  1.00  0.00           H  
HETATM   39  H19 UNL     1       1.633   0.792  -2.364  1.00  0.00           H  
HETATM   40  H20 UNL     1       3.362   0.723   1.922  1.00  0.00           H  
HETATM   41  H21 UNL     1       3.213  -1.062   1.952  1.00  0.00           H  
HETATM   42  H22 UNL     1       4.818  -2.511   0.817  1.00  0.00           H  
HETATM   43  H23 UNL     1       7.099  -2.701  -0.093  1.00  0.00           H  
HETATM   44  H24 UNL     1       8.440  -0.684  -0.671  1.00  0.00           H  
HETATM   45  H25 UNL     1       7.441   1.507  -0.312  1.00  0.00           H  
HETATM   46  H26 UNL     1       5.135   1.732   0.605  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    4    4
CONECT    3   24   25   26
CONECT    4    5   27
CONECT    5    6   28   29
CONECT    6    7   30   31
CONECT    7    8    9   32
CONECT    8   33   34   35
CONECT    9   10   36   37
CONECT   10   11   38   39
CONECT   11   12
CONECT   12   13   13   14
CONECT   14   15   40   41
CONECT   15   16   16   20
CONECT   16   17   42
CONECT   17   18   18   43
CONECT   18   19   44
CONECT   19   20   20   45
CONECT   20   46
END

HMDB0037230
     RDKit          3D
Citronellyl alpha-toluate
 46 46  0  0  0  0  0  0  0  0999 V2000
   -7.0248   -1.0235   -0.1717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8024   -0.1705   -0.0311 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8472    1.2774   -0.3423 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6723   -0.7133    0.3643 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4524    0.1366    0.5066 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3727   -0.2902   -0.4389 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1380    0.6017   -0.3251 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5507    0.5429    1.0406 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1592    0.2410   -1.3977 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758    1.0651   -1.4147 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8986    0.9725   -0.2958 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.5603   -0.1671    0.1065 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4312   -1.2133   -0.5630 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.4258   -0.1905    1.3051 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8204   -0.3663    0.7735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3797   -1.6024    0.5751 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6621   -1.7152    0.0650 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4294   -0.6093   -0.2644 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8480    0.6290   -0.0567 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5746    0.7540    0.4496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3966   -1.2534    0.8439 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7009   -1.9395   -0.7270 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8049   -0.4695   -0.7532 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7018    1.8887    0.5512 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8125    1.5556   -0.8247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0612    1.5624   -1.0998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6415   -1.7681    0.5820 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7512    1.1847    0.3925 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1311    0.0147    1.5748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1221   -1.3549   -0.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7543   -0.1475   -1.4688 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5131    1.6534   -0.5247 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0572   -0.4629    1.1654 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3152    0.6920    1.8461 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2497    1.3095    1.1362 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6777    0.2556   -2.4063 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1410   -0.8470   -1.3069 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8244    2.1722   -1.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6326    0.7917   -2.3641 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3620    0.7227    1.9219 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2130   -1.0622    1.9521 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8177   -2.5112    0.8168 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0986   -2.7011   -0.0925 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4400   -0.6837   -0.6710 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4411    1.5073   -0.3121 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1346    1.7317    0.6055 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  2  4  2  3
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  7  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 12 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 15  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  3 24  1  0
  3 25  1  0
  3 26  1  0
  4 27  1  0
  5 28  1  0
  5 29  1  0
  6 30  1  0
  6 31  1  0
  7 32  1  0
  8 33  1  0
  8 34  1  0
  8 35  1  0
  9 36  1  0
  9 37  1  0
 10 38  1  0
 10 39  1  0
 14 40  1  0
 14 41  1  0
 16 42  1  0
 17 43  1  0
 18 44  1  0
 19 45  1  0
 20 46  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Citronellyl a-toluate	Generator
Citronellyl a-toluic acid	Generator
Citronellyl alpha-toluic acid	Generator
Citronellyl α-toluate	Generator
Citronellyl α-toluic acid	Generator
3,7-Dimethyl-6-octen-1-yl phenylacetate	HMDB
3,7-Dimethyl-6-octenyl benzeneacetate	HMDB
3,7-Dimethyl-6-octenyl phenylacetate	HMDB
Acetic acid, phenyl-, 3,7-dimethyl-6-octenyl ester	HMDB
Benzeneacetic acid, 3,7-dimethyl-6-octen-1-yl ester	HMDB
Benzeneacetic acid, 3,7-dimethyl-6-octenyl ester	HMDB
Citronellyl phenylacetate	HMDB
e 2157	HMDB
FEMA 2315	HMDB

Chemical Formula

C₁₈H₂₆O₂

Average Molecular Weight

274.3978

Monoisotopic Molecular Weight

274.193280076

IUPAC Name

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

Traditional Name

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

CAS Registry Number

139-70-8

SMILES

CC(CCOC(=O)CC1=CC=CC=C1)CCC=C(C)C

InChI Identifier

InChI=1S/C18H26O2/c1-15(2)8-7-9-16(3)12-13-20-18(19)14-17-10-5-4-6-11-17/h4-6,8,10-11,16H,7,9,12-14H2,1-3H3

InChI Key

CVJBFMVLVJZZMM-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
Monocyclic monoterpenoid
Aromatic monoterpenoid
Benzenoid
Monocyclic benzene moiety
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
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: HMDB0037230)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0037230)

Source

Endogenous

Endogenous (HMDB: HMDB0037230)

Animal

Animal (HMDB: HMDB0037230)

Exogenous

Food

Food (HMDB: HMDB0037230)

Exogenous (HMDB: HMDB0037230)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid Peroxidation (HMDB: HMDB0037230)

Biochemical pathway

Metabolic pathway

Fatty Acid Metabolism (HMDB: HMDB0037230)

Lipid metabolism pathway (HMDB: HMDB0037230)

Cellular process

Cell signaling (HMDB: HMDB0037230)

Biochemical process

Lipid transport (HMDB: HMDB0037230)

Role

Biological role

Energy source (HMDB: HMDB0037230)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0037230)

Food and nutrition

Food additive

Flavoring agent

Flavoring Agent (HMDB: HMDB0037230)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	342.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.076 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	5.840 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0019 g/L	ALOGPS
logP	5.76	ALOGPS
logP	5.03	ChemAxon
logS	-5.2	ALOGPS
pKa (Strongest Basic)	-7.1	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	26.3 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	84.36 m³·mol⁻¹	ChemAxon
Polarizability	33.36 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	No	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]+	168.97	31661259
DarkChem	[M-H]-	166.702	31661259
DeepCCS	[M+H]+	168.856	30932474
DeepCCS	[M-H]-	166.498	30932474
DeepCCS	[M-2H]-	199.384	30932474
DeepCCS	[M+Na]+	174.949	30932474
AllCCS	[M+H]+	169.7	32859911
AllCCS	[M+H-H2O]+	166.5	32859911
AllCCS	[M+NH4]+	172.7	32859911
AllCCS	[M+Na]+	173.5	32859911
AllCCS	[M-H]-	174.3	32859911
AllCCS	[M+Na-2H]-	174.7	32859911
AllCCS	[M+HCOO]-	175.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Citronellyl alpha-toluate	CC(CCOC(=O)CC1=CC=CC=C1)CCC=C(C)C	2466.6	Standard polar	33892256
Citronellyl alpha-toluate	CC(CCOC(=O)CC1=CC=CC=C1)CCC=C(C)C	1867.6	Standard non polar	33892256
Citronellyl alpha-toluate	CC(CCOC(=O)CC1=CC=CC=C1)CCC=C(C)C	1990.6	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 alpha-toluate GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9200000000-073702b258e1adfe291b	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Citronellyl alpha-toluate 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 alpha-toluate 10V, Positive-QTOF	splash10-004i-2790000000-b80b9ebf5d1e9988ae87	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 20V, Positive-QTOF	splash10-014r-5910000000-59459f13b0171cad74f2	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 40V, Positive-QTOF	splash10-014l-9200000000-d3285050c4c3bcf49baf	2016-06-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 10V, Negative-QTOF	splash10-00xr-1960000000-3cc848e5dff32cce0761	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 20V, Negative-QTOF	splash10-00kr-1910000000-91f60ec045db0c03d31e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 40V, Negative-QTOF	splash10-014u-5900000000-dbca8249a000b0f9eecc	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 10V, Negative-QTOF	splash10-00di-0190000000-f2c2f8f406e6a5f92302	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 20V, Negative-QTOF	splash10-006x-9650000000-e1f54325e46d4d355368	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 40V, Negative-QTOF	splash10-0006-9300000000-088064f5b4177c2b53fc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 10V, Positive-QTOF	splash10-00o9-9740000000-a67826ffcf76a8757933	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 20V, Positive-QTOF	splash10-014l-9500000000-29d93ea0e54c4efc5f29	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Citronellyl alpha-toluate 40V, Positive-QTOF	splash10-0006-9200000000-f9e0b64e0f46a9afadfd	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

FDB016237

KNApSAcK ID

Not Available

Chemspider ID

8437

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

8767

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1020951

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.. .
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Showing metabocard for Citronellyl alpha-toluate (HMDB0037230)

MOL for HMDB0037230 (Citronellyl alpha-toluate)

3D MOL for HMDB0037230 (Citronellyl alpha-toluate)

3D SDF for HMDB0037230 (Citronellyl alpha-toluate)

3D-SDF for HMDB0037230 (Citronellyl alpha-toluate)

PDB for HMDB0037230 (Citronellyl alpha-toluate)

3D PDB for HMDB0037230 (Citronellyl alpha-toluate)

SMILES for HMDB0037230 (Citronellyl alpha-toluate)

INCHI for HMDB0037230 (Citronellyl alpha-toluate)

Structure for HMDB0037230 (Citronellyl alpha-toluate)

3D Structure for HMDB0037230 (Citronellyl alpha-toluate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra