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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 23:32:41 UTC

Update Date

2022-03-07 02:55:41 UTC

HMDB ID

HMDB0038259

Secondary Accession Numbers

HMDB38259

Metabolite Identification

Common Name

Neryl butyrate

Description

Geranyl butyrate is found in citrus. Geranyl butyrate is found in citrus peel oils, kumquat peel oil, celery leaves/stalks, tomato, yellow passion fruit, lavender oil and other essential oils. Geranyl butyrate is a flavouring agent.

Structure

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

HMDB0038259
     RDKit          3D
Neryl butyrate
 40 39  0  0  0  0  0  0  0  0999 V2000
   -3.8386   -2.1794   -0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3020   -0.9645   -1.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3301    0.2739   -0.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9854    0.6017   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9846   -0.0949   -0.3276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8625    1.6994    0.7314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6682    2.1351    1.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500    2.4303    0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5342    1.8588    0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4720    2.2865   -0.8959 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0193    0.8709    1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3499   -0.4941    0.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4014   -0.5790   -0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5522   -1.2145   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7932   -1.8537    1.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5932   -1.2843   -1.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6948   -2.8608   -0.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662   -1.9870    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2077   -2.8031   -1.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7273   -0.7923   -2.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3539   -1.1453   -1.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6321    1.1296   -1.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0418    0.1432    0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4114    1.4000    2.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9516    3.0912    1.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8556    3.2056   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3573    3.4050   -1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110    2.0611   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1957    1.8580   -1.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3904    0.7177    2.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9995    1.2501    1.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4554   -1.0306    0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7343   -1.0768    1.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2828   -0.1455   -1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0290   -2.6216    1.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7256   -1.0785    1.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7946   -2.3442    1.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5608   -0.9901   -0.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6547   -2.2935   -1.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.5846   -2.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END

  Mrv0541 02241215192D          

 16 15  0  0  0  0            999 V2000
    2.1436    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1436    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8573    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4286    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7150    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150    1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286    0.6187    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -0.2062    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -0.6187    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1436   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8573   -1.8563    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4286   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7150   -1.4437    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000   -1.8563    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
  2  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  7  9  2  0  0  0  0
  9 10  1  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 12 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0038259

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCC(=O)OC\C=C(\C)CCC=C(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C14H24O2/c1-5-7-14(15)16-11-10-13(4)9-6-8-12(2)3/h8,10H,5-7,9,11H2,1-4H3/b13-10-

> <INCHI_KEY>
ZSBOMYJPSRFZAL-RAXLEYEMSA-N

> <FORMULA>
C14H24O2

> <MOLECULAR_WEIGHT>
224.3392

> <EXACT_MASS>
224.177630012

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
27.627011299804128

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
0

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2Z)-3,7-dimethylocta-2,6-dien-1-yl butanoate

> <ALOGPS_LOGP>
5.07

> <JCHEM_LOGP>
4.088613218333333

> <ALOGPS_LOGS>
-3.58

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_BASIC>
-7.043254283144128

> <JCHEM_POLAR_SURFACE_AREA>
26.3

> <JCHEM_REFRACTIVITY>
69.56150000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
8

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.97e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2Z)-3,7-dimethylocta-2,6-dien-1-yl butanoate

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0038259
     RDKit          3D
Neryl butyrate
 40 39  0  0  0  0  0  0  0  0999 V2000
   -3.8386   -2.1794   -0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3020   -0.9645   -1.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3301    0.2739   -0.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9854    0.6017   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9846   -0.0949   -0.3276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8625    1.6994    0.7314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6682    2.1351    1.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500    2.4303    0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5342    1.8588    0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4720    2.2865   -0.8959 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0193    0.8709    1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3499   -0.4941    0.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4014   -0.5790   -0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5522   -1.2145   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7932   -1.8537    1.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5932   -1.2843   -1.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6948   -2.8608   -0.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662   -1.9870    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2077   -2.8031   -1.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7273   -0.7923   -2.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3539   -1.1453   -1.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6321    1.1296   -1.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0418    0.1432    0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4114    1.4000    2.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9516    3.0912    1.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8556    3.2056   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3573    3.4050   -1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110    2.0611   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1957    1.8580   -1.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3904    0.7177    2.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9995    1.2501    1.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4554   -1.0306    0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7343   -1.0768    1.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2828   -0.1455   -1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0290   -2.6216    1.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7256   -1.0785    1.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7946   -2.3442    1.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5608   -0.9901   -0.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6547   -2.2935   -1.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.5846   -2.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END

HEADER    PROTEIN                                 24-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   24-FEB-12         0                                  
HETATM    1  C   UNK     0       4.001   3.465   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       4.001   1.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0       5.334   1.155   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       2.667   1.155   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       1.335   1.925   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       0.000   1.155   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.335   1.925   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.335   3.465   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      -2.667   1.155   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      -2.667  -0.385   0.000  0.00  0.00           C+0
HETATM   11  O   UNK     0      -4.001  -1.155   0.000  0.00  0.00           O+0
HETATM   12  C   UNK     0      -4.001  -2.695   0.000  0.00  0.00           C+0
HETATM   13  O   UNK     0      -5.334  -3.465   0.000  0.00  0.00           O+0
HETATM   14  C   UNK     0      -2.667  -3.465   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      -1.335  -2.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.000  -3.465   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3    4                                                  
CONECT    3    2                                                            
CONECT    4    2    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8    9                                                  
CONECT    8    7                                                            
CONECT    9    7   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13   14                                                  
CONECT   13   12                                                            
CONECT   14   12   15                                                       
CONECT   15   14   16                                                       
CONECT   16   15                                                            
MASTER        0    0    0    0    0    0    0    0   16    0   30    0
END

COMPND    HMDB0038259
HETATM    1  C1  UNL     1      -3.839  -2.179  -0.747  1.00  0.00           C  
HETATM    2  C2  UNL     1      -4.302  -0.964  -1.477  1.00  0.00           C  
HETATM    3  C3  UNL     1      -4.330   0.274  -0.612  1.00  0.00           C  
HETATM    4  C4  UNL     1      -2.985   0.602  -0.069  1.00  0.00           C  
HETATM    5  O1  UNL     1      -1.985  -0.095  -0.328  1.00  0.00           O  
HETATM    6  O2  UNL     1      -2.862   1.699   0.731  1.00  0.00           O  
HETATM    7  C5  UNL     1      -1.668   2.135   1.317  1.00  0.00           C  
HETATM    8  C6  UNL     1      -0.650   2.430   0.313  1.00  0.00           C  
HETATM    9  C7  UNL     1       0.534   1.859   0.215  1.00  0.00           C  
HETATM   10  C8  UNL     1       1.472   2.286  -0.896  1.00  0.00           C  
HETATM   11  C9  UNL     1       1.019   0.871   1.161  1.00  0.00           C  
HETATM   12  C10 UNL     1       1.350  -0.494   0.659  1.00  0.00           C  
HETATM   13  C11 UNL     1       2.401  -0.579  -0.370  1.00  0.00           C  
HETATM   14  C12 UNL     1       3.552  -1.214  -0.153  1.00  0.00           C  
HETATM   15  C13 UNL     1       3.793  -1.854   1.146  1.00  0.00           C  
HETATM   16  C14 UNL     1       4.593  -1.284  -1.206  1.00  0.00           C  
HETATM   17  H1  UNL     1      -4.695  -2.861  -0.480  1.00  0.00           H  
HETATM   18  H2  UNL     1      -3.266  -1.987   0.167  1.00  0.00           H  
HETATM   19  H3  UNL     1      -3.208  -2.803  -1.444  1.00  0.00           H  
HETATM   20  H4  UNL     1      -3.727  -0.792  -2.408  1.00  0.00           H  
HETATM   21  H5  UNL     1      -5.354  -1.145  -1.799  1.00  0.00           H  
HETATM   22  H6  UNL     1      -4.632   1.130  -1.244  1.00  0.00           H  
HETATM   23  H7  UNL     1      -5.042   0.143   0.212  1.00  0.00           H  
HETATM   24  H8  UNL     1      -1.411   1.400   2.085  1.00  0.00           H  
HETATM   25  H9  UNL     1      -1.952   3.091   1.864  1.00  0.00           H  
HETATM   26  H10 UNL     1      -0.856   3.206  -0.460  1.00  0.00           H  
HETATM   27  H11 UNL     1       1.357   3.405  -1.038  1.00  0.00           H  
HETATM   28  H12 UNL     1       2.511   2.061  -0.623  1.00  0.00           H  
HETATM   29  H13 UNL     1       1.196   1.858  -1.862  1.00  0.00           H  
HETATM   30  H14 UNL     1       0.390   0.718   2.072  1.00  0.00           H  
HETATM   31  H15 UNL     1       2.000   1.250   1.643  1.00  0.00           H  
HETATM   32  H16 UNL     1       0.455  -1.031   0.255  1.00  0.00           H  
HETATM   33  H17 UNL     1       1.734  -1.077   1.558  1.00  0.00           H  
HETATM   34  H18 UNL     1       2.283  -0.146  -1.357  1.00  0.00           H  
HETATM   35  H19 UNL     1       3.029  -2.622   1.336  1.00  0.00           H  
HETATM   36  H20 UNL     1       3.726  -1.079   1.943  1.00  0.00           H  
HETATM   37  H21 UNL     1       4.795  -2.344   1.167  1.00  0.00           H  
HETATM   38  H22 UNL     1       5.561  -0.990  -0.716  1.00  0.00           H  
HETATM   39  H23 UNL     1       4.655  -2.293  -1.652  1.00  0.00           H  
HETATM   40  H24 UNL     1       4.357  -0.585  -2.057  1.00  0.00           H  
CONECT    1    2   17   18   19
CONECT    2    3   20   21
CONECT    3    4   22   23
CONECT    4    5    5    6
CONECT    6    7
CONECT    7    8   24   25
CONECT    8    9    9   26
CONECT    9   10   11
CONECT   10   27   28   29
CONECT   11   12   30   31
CONECT   12   13   32   33
CONECT   13   14   14   34
CONECT   14   15   16
CONECT   15   35   36   37
CONECT   16   38   39   40
END

HMDB0038259
     RDKit          3D
Neryl butyrate
 40 39  0  0  0  0  0  0  0  0999 V2000
   -3.8386   -2.1794   -0.7466 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3020   -0.9645   -1.4767 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3301    0.2739   -0.6117 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9854    0.6017   -0.0694 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9846   -0.0949   -0.3276 O   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8625    1.6994    0.7314 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6682    2.1351    1.3171 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6500    2.4303    0.3132 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5342    1.8588    0.2152 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4720    2.2865   -0.8959 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0193    0.8709    1.1611 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3499   -0.4941    0.6594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.4014   -0.5790   -0.3696 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5522   -1.2145   -0.1525 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7932   -1.8537    1.1462 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5932   -1.2843   -1.2059 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6948   -2.8608   -0.4804 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2662   -1.9870    0.1665 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2077   -2.8031   -1.4438 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7273   -0.7923   -2.4075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3539   -1.1453   -1.7992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6321    1.1296   -1.2444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0418    0.1432    0.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4114    1.4000    2.0852 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9516    3.0912    1.8639 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8556    3.2056   -0.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3573    3.4050   -1.0384 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5110    2.0611   -0.6225 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1957    1.8580   -1.8624 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3904    0.7177    2.0725 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9995    1.2501    1.6434 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4554   -1.0306    0.2554 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7343   -1.0768    1.5578 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.2828   -0.1455   -1.3570 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0290   -2.6216    1.3357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7256   -1.0785    1.9431 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7946   -2.3442    1.1671 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5608   -0.9901   -0.7158 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6547   -2.2935   -1.6524 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.3570   -0.5846   -2.0573 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  2  0
  4  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  2  0
  9 10  1  0
  9 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  2  3
 14 15  1  0
 14 16  1  0
  1 17  1  0
  1 18  1  0
  1 19  1  0
  2 20  1  0
  2 21  1  0
  3 22  1  0
  3 23  1  0
  7 24  1  0
  7 25  1  0
  8 26  1  0
 10 27  1  0
 10 28  1  0
 10 29  1  0
 11 30  1  0
 11 31  1  0
 12 32  1  0
 12 33  1  0
 13 34  1  0
 15 35  1  0
 15 36  1  0
 15 37  1  0
 16 38  1  0
 16 39  1  0
 16 40  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Neryl butyric acid	Generator
(Z)-3,7-Dimethyl-2,6-octadienyl butanoate	HMDB
(Z)-3,7-Dimethyl-2,6-octadienyl butyrate	HMDB
3,7-Dimethyl-2,6-octadienyl ester(Z)-butanoic acid	HMDB
3,7-Dimethyl-2,6-octadienyl ester(Z)-butyric acid	HMDB
3,7-Dimethyl-2,6-octadienyl esterz)-butanoic acid	HMDB
Butanoic acid, (2Z)-3,7-dimethyl-2,6-octadien-1-yl ester	HMDB
Butanoic acid, (2Z)-3,7-dimethyl-2,6-octadienyl ester	HMDB
cis-3,7-Dimethyl-2,6-octadienyl butanoate	HMDB
FEMA 2774	HMDB
Neryl butanoate	HMDB
Nonyl N-butyrate	HMDB
(Z)-3,7-Dimethyl-2,6-octadienyl butyric acid	Generator
Geranyl butyric acid	Generator

Chemical Formula

C₁₄H₂₄O₂

Average Molecular Weight

224.3392

Monoisotopic Molecular Weight

224.177630012

IUPAC Name

(2Z)-3,7-dimethylocta-2,6-dien-1-yl butanoate

Traditional Name

(2Z)-3,7-dimethylocta-2,6-dien-1-yl butanoate

CAS Registry Number

999-40-6

SMILES

CCCC(=O)OC\C=C(\C)CCC=C(C)C

InChI Identifier

InChI=1S/C14H24O2/c1-5-7-14(15)16-11-10-13(4)9-6-8-12(2)3/h8,10H,5-7,9,11H2,1-4H3/b13-10-

InChI Key

ZSBOMYJPSRFZAL-RAXLEYEMSA-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
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

Wax monoesters (LMFA07010626 )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0038259)
Membrane (HMDB: HMDB0038259)

Source

Endogenous

Endogenous (HMDB: HMDB0038259)

Exogenous

Exogenous (HMDB: HMDB0038259)

Process

Not Available

Role

Not Available

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	239.00 to 240.00 °C. @ 760.00 mm Hg	The Good Scents Company Information System
Water Solubility	0.71 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	4.923 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.06 g/L	ALOGPS
logP	5.07	ALOGPS
logP	4.09	ChemAxon
logS	-3.6	ALOGPS
pKa (Strongest Basic)	-7	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	69.56 m³·mol⁻¹	ChemAxon
Polarizability	27.63 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]+	154.085	31661259
DarkChem	[M-H]-	154.016	31661259
DeepCCS	[M+H]+	156.604	30932474
DeepCCS	[M-H]-	154.246	30932474
DeepCCS	[M-2H]-	187.718	30932474
DeepCCS	[M+Na]+	162.811	30932474
AllCCS	[M+H]+	159.4	32859911
AllCCS	[M+H-H2O]+	156.0	32859911
AllCCS	[M+NH4]+	162.6	32859911
AllCCS	[M+Na]+	163.5	32859911
AllCCS	[M-H]-	159.8	32859911
AllCCS	[M+Na-2H]-	160.9	32859911
AllCCS	[M+HCOO]-	162.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Neryl butyrate	CCCC(=O)OC\C=C(\C)CCC=C(C)C	1852.8	Standard polar	33892256
Neryl butyrate	CCCC(=O)OC\C=C(\C)CCC=C(C)C	1503.9	Standard non polar	33892256
Neryl butyrate	CCCC(=O)OC\C=C(\C)CCC=C(C)C	1584.4	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Neryl butyrate EI-B (Non-derivatized)	splash10-014l-9100000000-0bc04e3a6c520f0cfadd	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Neryl butyrate EI-B (Non-derivatized)	splash10-014l-9100000000-0bc04e3a6c520f0cfadd	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neryl butyrate GC-MS (Non-derivatized) - 70eV, Positive	splash10-060c-9700000000-f17b16d0d76dc338c089	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Neryl butyrate 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 - Neryl butyrate 10V, Positive-QTOF	splash10-004r-5960000000-5b753b26564fadc84dd6	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neryl butyrate 20V, Positive-QTOF	splash10-0079-9600000000-9746fc341340ae0eca4f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neryl butyrate 40V, Positive-QTOF	splash10-0gbc-9100000000-40e406f728e794d88c52	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neryl butyrate 10V, Negative-QTOF	splash10-00y0-9470000000-302dfcd1a756ed78a4d9	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neryl butyrate 20V, Negative-QTOF	splash10-00kr-9200000000-50eeec28209003ce0bdd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neryl butyrate 40V, Negative-QTOF	splash10-00ko-9300000000-a79607bd760573fee44b	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neryl butyrate 10V, Positive-QTOF	splash10-001i-9400000000-b75572ea773801a9bb22	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neryl butyrate 20V, Positive-QTOF	splash10-001i-9100000000-8e70f8f7070d443f5535	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neryl butyrate 40V, Positive-QTOF	splash10-0006-9100000000-1ee9f7115b0d598da89a	2021-09-21	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neryl butyrate 10V, Negative-QTOF	splash10-00dr-8290000000-194292342db985cc328a	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neryl butyrate 20V, Negative-QTOF	splash10-000i-9100000000-b6a318fb443d044e2e0e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Neryl butyrate 40V, Negative-QTOF	splash10-014i-9000000000-9f2867696f737c8488c7	2021-09-25	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

FDB018005

KNApSAcK ID

Not Available

Chemspider ID

4509113

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5352162

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1033141

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Neryl butyrate (HMDB0038259)

MOL for HMDB0038259 (Neryl butyrate)

3D MOL for HMDB0038259 (Neryl butyrate)

3D SDF for HMDB0038259 (Neryl butyrate)

3D-SDF for HMDB0038259 (Neryl butyrate)

PDB for HMDB0038259 (Neryl butyrate)

3D PDB for HMDB0038259 (Neryl butyrate)

SMILES for HMDB0038259 (Neryl butyrate)

INCHI for HMDB0038259 (Neryl butyrate)

Structure for HMDB0038259 (Neryl butyrate)

3D Structure for HMDB0038259 (Neryl butyrate)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

GC-MS Spectra

MS/MS Spectra