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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-11 17:41:30 UTC

Update Date

2022-03-07 02:52:51 UTC

HMDB ID

HMDB0031184

Secondary Accession Numbers

HMDB31184

Metabolite Identification

Common Name

N-Isobutyl-2,4,8,10,12-tetradecapentaenamide

Description

N-Isobutyl-2,4,8,10,12-tetradecapentaenamide belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage. Thus, N-isobutyl-2,4,8,10,12-tetradecapentaenamide is considered to be a fatty amide. Based on a literature review a small amount of articles have been published on N-Isobutyl-2,4,8,10,12-tetradecapentaenamide.

Structure

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

HMDB0031184
     RDKit          3D
N-Isobutyl-2,4,8,10,12-tetradecapentaenamide
 47 46  0  0  0  0  0  0  0  0999 V2000
   10.0184    1.1943   -0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5638    1.2053   -0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7570    0.3454   -0.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3208    0.3196   -0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5139   -0.5348   -1.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0597   -0.5137   -0.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2461   -1.3702   -1.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7691   -1.3622   -1.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3983   -0.2646   -0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0750   -0.3011    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8515    0.7216   -0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2908    0.6784   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0684    1.7047   -0.3172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4969    1.6958   -0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1815    2.7356   -0.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2234    0.5978    0.3845 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6459    0.6150    0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1746   -0.6793    1.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8772   -1.8518    0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6025   -0.9838    2.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3440    2.1457   -0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5370    1.0211    0.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2602    0.3625   -1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1355    1.9318    0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
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    3.6490   -2.0937   -2.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1841   -1.2648   -2.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5355   -2.3518   -0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6914    0.7222   -0.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8954   -0.4500    0.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5584   -1.1930    0.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4082    1.6148   -0.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7248   -0.2483    0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5362    2.5796   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7170   -0.2716    0.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9813    1.4263    1.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1086    0.7473   -0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2769   -0.5925    1.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8119   -1.5616   -0.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7067   -2.5770    0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9523   -2.3469    0.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2635   -0.6293    3.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6013   -0.4691    2.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv0541 02241216432D          

 20 19  0  0  0  0            999 V2000
   -5.0038    0.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2890    0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -2.8593    0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1445    0.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4296    0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7148    0.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0000    0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.7148    0.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4296    0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1445    0.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8593    0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5740    0.4992    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2890    0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0038    0.4992    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.2890    1.7374    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.0038   -0.3271    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4199   -0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4199   -1.7374    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5934   -0.9111    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0031184

> <DATABASE_NAME>
hmdb

> <SMILES>
C\C=C\C=C\C=C\CC\C=C\C=C\C(=O)NCC(C)C

> <INCHI_IDENTIFIER>
InChI=1S/C18H27NO/c1-4-5-6-7-8-9-10-11-12-13-14-15-18(20)19-16-17(2)3/h4-9,12-15,17H,10-11,16H2,1-3H3,(H,19,20)/b5-4+,7-6+,9-8+,13-12+,15-14+

> <INCHI_KEY>
KVUKDCFEXVWYBN-FMBIJHKPSA-N

> <FORMULA>
C18H27NO

> <MOLECULAR_WEIGHT>
273.4131

> <EXACT_MASS>
273.209264491

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
35.493439901871966

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(2E,4E,8E,10E,12E)-N-(2-methylpropyl)tetradeca-2,4,8,10,12-pentaenamide

> <ALOGPS_LOGP>
5.30

> <JCHEM_LOGP>
4.578618938666667

> <ALOGPS_LOGS>
-5.28

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.35418549683771

> <JCHEM_PKA_STRONGEST_BASIC>
2.245613940279428

> <JCHEM_POLAR_SURFACE_AREA>
29.1

> <JCHEM_REFRACTIVITY>
93.9044

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.44e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(2E,4E,8E,10E,12E)-N-(2-methylpropyl)tetradeca-2,4,8,10,12-pentaenamide

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0031184
     RDKit          3D
N-Isobutyl-2,4,8,10,12-tetradecapentaenamide
 47 46  0  0  0  0  0  0  0  0999 V2000
   10.0184    1.1943   -0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5638    1.2053   -0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7570    0.3454   -0.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3208    0.3196   -0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5139   -0.5348   -1.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0597   -0.5137   -0.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2461   -1.3702   -1.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7691   -1.3622   -1.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3983   -0.2646   -0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0750   -0.3011    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8515    0.7216   -0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2908    0.6784   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0684    1.7047   -0.3172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4969    1.6958   -0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1815    2.7356   -0.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2234    0.5978    0.3845 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6459    0.6150    0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1746   -0.6793    1.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8772   -1.8518    0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6025   -0.9838    2.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3440    2.1457   -0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5370    1.0211    0.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2602    0.3625   -1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1355    1.9318    0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1950   -0.3746   -1.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8712    1.0392    0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9450   -1.2569   -1.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6312    0.2101   -0.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6490   -2.0937   -2.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1841   -1.2648   -2.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.4082    1.6148   -0.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7248   -0.2483    0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5362    2.5796   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7170   -0.2716    0.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.2769   -0.5925    1.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.7067   -2.5770    0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9523   -2.3469    0.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2635   -0.6293    3.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6013   -0.4691    2.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3869   -2.0542    2.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
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 20 46  1  0
 20 47  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      -9.340   0.932   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      -8.006   1.701   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      -6.672   0.932   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      -5.337   1.701   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      -4.003   0.932   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      -2.669   1.701   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      -1.334   0.932   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       0.000   1.701   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       1.334   0.932   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       2.669   1.701   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       4.003   0.932   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       5.337   1.701   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       6.671   0.932   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       8.006   1.701   0.000  0.00  0.00           C+0
HETATM   15  N   UNK     0       9.340   0.932   0.000  0.00  0.00           N+0
HETATM   16  O   UNK     0       8.006   3.243   0.000  0.00  0.00           O+0
HETATM   17  C   UNK     0       9.340  -0.611   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       8.250  -1.701   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       8.250  -3.243   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       6.708  -1.701   0.000  0.00  0.00           C+0
CONECT    1    2                                                            
CONECT    2    1    3                                                       
CONECT    3    2    4                                                       
CONECT    4    3    5                                                       
CONECT    5    4    6                                                       
CONECT    6    5    7                                                       
CONECT    7    6    8                                                       
CONECT    8    7    9                                                       
CONECT    9    8   10                                                       
CONECT   10    9   11                                                       
CONECT   11   10   12                                                       
CONECT   12   11   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13   15   16                                                  
CONECT   15   14   17                                                       
CONECT   16   14                                                            
CONECT   17   15   18                                                       
CONECT   18   17   19   20                                                  
CONECT   19   18                                                            
CONECT   20   18                                                            
MASTER        0    0    0    0    0    0    0    0   20    0   38    0
END

COMPND    HMDB0031184
HETATM    1  C1  UNL     1      10.018   1.194  -0.335  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.564   1.205  -0.091  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.757   0.345  -0.680  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.321   0.320  -0.470  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.514  -0.535  -1.055  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.060  -0.514  -0.803  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.246  -1.370  -1.388  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.769  -1.362  -1.143  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.398  -0.265  -0.166  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.075  -0.301   0.042  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.851   0.722  -0.240  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.291   0.678  -0.033  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.068   1.705  -0.317  1.00  0.00           C  
HETATM   14  C14 UNL     1      -4.497   1.696  -0.125  1.00  0.00           C  
HETATM   15  O1  UNL     1      -5.181   2.736  -0.426  1.00  0.00           O  
HETATM   16  N1  UNL     1      -5.223   0.598   0.384  1.00  0.00           N  
HETATM   17  C15 UNL     1      -6.646   0.615   0.567  1.00  0.00           C  
HETATM   18  C16 UNL     1      -7.175  -0.679   1.123  1.00  0.00           C  
HETATM   19  C17 UNL     1      -6.877  -1.852   0.224  1.00  0.00           C  
HETATM   20  C18 UNL     1      -6.602  -0.984   2.492  1.00  0.00           C  
HETATM   21  H1  UNL     1      10.344   2.146  -0.778  1.00  0.00           H  
HETATM   22  H2  UNL     1      10.537   1.021   0.613  1.00  0.00           H  
HETATM   23  H3  UNL     1      10.260   0.362  -1.057  1.00  0.00           H  
HETATM   24  H4  UNL     1       8.135   1.932   0.586  1.00  0.00           H  
HETATM   25  H5  UNL     1       8.195  -0.375  -1.353  1.00  0.00           H  
HETATM   26  H6  UNL     1       5.871   1.039   0.204  1.00  0.00           H  
HETATM   27  H7  UNL     1       5.945  -1.257  -1.730  1.00  0.00           H  
HETATM   28  H8  UNL     1       3.631   0.210  -0.128  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.649  -2.094  -2.059  1.00  0.00           H  
HETATM   30  H10 UNL     1       1.184  -1.265  -2.060  1.00  0.00           H  
HETATM   31  H11 UNL     1       1.536  -2.352  -0.698  1.00  0.00           H  
HETATM   32  H12 UNL     1       1.691   0.722  -0.534  1.00  0.00           H  
HETATM   33  H13 UNL     1       1.895  -0.450   0.792  1.00  0.00           H  
HETATM   34  H14 UNL     1      -0.558  -1.193   0.442  1.00  0.00           H  
HETATM   35  H15 UNL     1      -0.408   1.615  -0.634  1.00  0.00           H  
HETATM   36  H16 UNL     1      -2.725  -0.248   0.373  1.00  0.00           H  
HETATM   37  H17 UNL     1      -2.536   2.580  -0.717  1.00  0.00           H  
HETATM   38  H18 UNL     1      -4.717  -0.272   0.644  1.00  0.00           H  
HETATM   39  H19 UNL     1      -6.981   1.426   1.262  1.00  0.00           H  
HETATM   40  H20 UNL     1      -7.109   0.747  -0.434  1.00  0.00           H  
HETATM   41  H21 UNL     1      -8.277  -0.592   1.206  1.00  0.00           H  
HETATM   42  H22 UNL     1      -6.812  -1.562  -0.843  1.00  0.00           H  
HETATM   43  H23 UNL     1      -7.707  -2.577   0.311  1.00  0.00           H  
HETATM   44  H24 UNL     1      -5.952  -2.347   0.594  1.00  0.00           H  
HETATM   45  H25 UNL     1      -7.264  -0.629   3.282  1.00  0.00           H  
HETATM   46  H26 UNL     1      -5.601  -0.469   2.523  1.00  0.00           H  
HETATM   47  H27 UNL     1      -6.387  -2.054   2.633  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3    3   24
CONECT    3    4   25
CONECT    4    5    5   26
CONECT    5    6   27
CONECT    6    7    7   28
CONECT    7    8   29
CONECT    8    9   30   31
CONECT    9   10   32   33
CONECT   10   11   11   34
CONECT   11   12   35
CONECT   12   13   13   36
CONECT   13   14   37
CONECT   14   15   15   16
CONECT   16   17   38
CONECT   17   18   39   40
CONECT   18   19   20   41
CONECT   19   42   43   44
CONECT   20   45   46   47
END

HMDB0031184
     RDKit          3D
N-Isobutyl-2,4,8,10,12-tetradecapentaenamide
 47 46  0  0  0  0  0  0  0  0999 V2000
   10.0184    1.1943   -0.3350 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.5638    1.2053   -0.0911 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7570    0.3454   -0.6805 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3208    0.3196   -0.4704 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5139   -0.5348   -1.0552 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0597   -0.5137   -0.8029 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2461   -1.3702   -1.3884 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7691   -1.3622   -1.1433 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3983   -0.2646   -0.1657 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0750   -0.3011    0.0425 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8515    0.7216   -0.2397 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2908    0.6784   -0.0334 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0684    1.7047   -0.3172 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4969    1.6958   -0.1250 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1815    2.7356   -0.4259 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2234    0.5978    0.3845 N   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6459    0.6150    0.5666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1746   -0.6793    1.1234 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8772   -1.8518    0.2239 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6025   -0.9838    2.4921 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3440    2.1457   -0.7777 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5370    1.0211    0.6131 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2602    0.3625   -1.0570 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1355    1.9318    0.5860 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1950   -0.3746   -1.3530 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8712    1.0392    0.2043 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9450   -1.2569   -1.7295 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6312    0.2101   -0.1276 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6490   -2.0937   -2.0590 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1841   -1.2648   -2.0598 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5355   -2.3518   -0.6984 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6914    0.7222   -0.5344 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8954   -0.4500    0.7917 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5584   -1.1930    0.4417 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4082    1.6148   -0.6343 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7248   -0.2483    0.3730 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5362    2.5796   -0.7169 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7170   -0.2716    0.6444 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9813    1.4263    1.2623 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1086    0.7473   -0.4336 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2769   -0.5925    1.2060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8119   -1.5616   -0.8434 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7067   -2.5770    0.3111 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9523   -2.3469    0.5943 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2635   -0.6293    3.2818 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6013   -0.4691    2.5226 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3869   -2.0542    2.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
 10 11  2  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  2  0
 14 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 18 20  1  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  3 25  1  0
  4 26  1  0
  5 27  1  0
  6 28  1  0
  7 29  1  0
  8 30  1  0
  8 31  1  0
  9 32  1  0
  9 33  1  0
 10 34  1  0
 11 35  1  0
 12 36  1  0
 13 37  1  0
 16 38  1  0
 17 39  1  0
 17 40  1  0
 18 41  1  0
 19 42  1  0
 19 43  1  0
 19 44  1  0
 20 45  1  0
 20 46  1  0
 20 47  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
g-Sanshool	HMDB

Chemical Formula

C₁₈H₂₇NO

Average Molecular Weight

273.4131

Monoisotopic Molecular Weight

273.209264491

IUPAC Name

(2E,4E,8E,10E,12E)-N-(2-methylpropyl)tetradeca-2,4,8,10,12-pentaenamide

Traditional Name

(2E,4E,8E,10E,12E)-N-(2-methylpropyl)tetradeca-2,4,8,10,12-pentaenamide

CAS Registry Number

78886-65-4

SMILES

C\C=C\C=C\C=C\CC\C=C\C=C\C(=O)NCC(C)C

InChI Identifier

InChI=1S/C18H27NO/c1-4-5-6-7-8-9-10-11-12-13-14-15-18(20)19-16-17(2)3/h4-9,12-15,17H,10-11,16H2,1-3H3,(H,19,20)/b5-4+,7-6+,9-8+,13-12+,15-14+

InChI Key

KVUKDCFEXVWYBN-FMBIJHKPSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acyl amines. N-acyl amines are compounds containing a fatty acid moiety linked to an amine group through an ester linkage.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

N-acyl amines

Alternative Parents

Substituents

N-acyl-amine
Secondary carboxylic acid amide
Carboxamide group
Carboxylic acid derivative
Organic nitrogen compound
Organic oxygen compound
Organopnictogen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Organonitrogen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cytoplasm (HMDB: HMDB0031184)
Cell membrane (HMDB: HMDB0031184)

Biofluid or Excreta

Urine (HMDB: HMDB0031184)

Cellular substructure

Extracellular (HMDB: HMDB0031184)
Membrane (HMDB: HMDB0031184)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0031184)

Source

Endogenous

Endogenous (HMDB: HMDB0031184)

Plant

Plant (HMDB: HMDB0031184)

Animal

Animal (HMDB: HMDB0031184)

Exogenous

Food

Food (HMDB: HMDB0031184)

Herb and spice

Herbs and Spices (FooDB: FOOD00866)

Process

Naturally occurring process

Biological process

Chemical reaction

Lipid peroxidation (HMDB: HMDB0031184)

Biochemical process

Fatty acid metabolism (HMDB: HMDB0031184)

Cellular process

Cell signaling (HMDB: HMDB0031184)

Biochemical pathway

Lipid metabolism pathway (HMDB: HMDB0031184)

Role

Biological role

Membrane stabilizer (HMDB: HMDB0031184)

Nutrient

Nutrient (HMDB: HMDB0031184)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0031184)

Emulsifier (HMDB: HMDB0031184)

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	88 - 89 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0014 g/L	ALOGPS
logP	5.3	ALOGPS
logP	4.58	ChemAxon
logS	-5.3	ALOGPS
pKa (Strongest Acidic)	16.35	ChemAxon
pKa (Strongest Basic)	2.25	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	93.9 m³·mol⁻¹	ChemAxon
Polarizability	35.49 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
DeepCCS	[M+H]+	172.301	30932474
DeepCCS	[M-H]-	169.943	30932474
DeepCCS	[M-2H]-	202.829	30932474
DeepCCS	[M+Na]+	178.394	30932474
AllCCS	[M+H]+	172.7	32859911
AllCCS	[M+H-H2O]+	169.4	32859911
AllCCS	[M+NH4]+	175.7	32859911
AllCCS	[M+Na]+	176.6	32859911
AllCCS	[M-H]-	172.2	32859911
AllCCS	[M+Na-2H]-	173.2	32859911
AllCCS	[M+HCOO]-	174.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
N-Isobutyl-2,4,8,10,12-tetradecapentaenamide	C\C=C\C=C\C=C\CC\C=C\C=C\C(=O)NCC(C)C	3430.0	Standard polar	33892256
N-Isobutyl-2,4,8,10,12-tetradecapentaenamide	C\C=C\C=C\C=C\CC\C=C\C=C\C(=O)NCC(C)C	2279.2	Standard non polar	33892256
N-Isobutyl-2,4,8,10,12-tetradecapentaenamide	C\C=C\C=C\C=C\CC\C=C\C=C\C(=O)NCC(C)C	2498.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
N-Isobutyl-2,4,8,10,12-tetradecapentaenamide,1TMS,isomer #1	C/C=C/C=C/C=C/CC/C=C/C=C/C(=O)N(CC(C)C)[Si](C)(C)C	2389.8	Semi standard non polar	33892256
N-Isobutyl-2,4,8,10,12-tetradecapentaenamide,1TMS,isomer #1	C/C=C/C=C/C=C/CC/C=C/C=C/C(=O)N(CC(C)C)[Si](C)(C)C	2564.1	Standard non polar	33892256
N-Isobutyl-2,4,8,10,12-tetradecapentaenamide,1TBDMS,isomer #1	C/C=C/C=C/C=C/CC/C=C/C=C/C(=O)N(CC(C)C)[Si](C)(C)C(C)(C)C	2587.8	Semi standard non polar	33892256
N-Isobutyl-2,4,8,10,12-tetradecapentaenamide,1TBDMS,isomer #1	C/C=C/C=C/C=C/CC/C=C/C=C/C(=O)N(CC(C)C)[Si](C)(C)C(C)(C)C	2730.0	Standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - N-Isobutyl-2,4,8,10,12-tetradecapentaenamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0a4i-6950000000-0727b5a358351fcb8442	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Isobutyl-2,4,8,10,12-tetradecapentaenamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - N-Isobutyl-2,4,8,10,12-tetradecapentaenamide 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 - N-Isobutyl-2,4,8,10,12-tetradecapentaenamide 10V, Negative-QTOF	splash10-00di-0090000000-ec7cca8f3a30403efd86	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Isobutyl-2,4,8,10,12-tetradecapentaenamide 20V, Negative-QTOF	splash10-00di-4690000000-512363cddac8e7a76bae	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Isobutyl-2,4,8,10,12-tetradecapentaenamide 40V, Negative-QTOF	splash10-00dl-9610000000-62acf4fe7c61338aa9fd	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Isobutyl-2,4,8,10,12-tetradecapentaenamide 10V, Negative-QTOF	splash10-00di-0390000000-aca37aa4bfb04b4d4236	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Isobutyl-2,4,8,10,12-tetradecapentaenamide 20V, Negative-QTOF	splash10-00di-2970000000-315b83660c1cddf75132	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Isobutyl-2,4,8,10,12-tetradecapentaenamide 40V, Negative-QTOF	splash10-014i-6900000000-79835fe9c67f1694c5e8	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Isobutyl-2,4,8,10,12-tetradecapentaenamide 10V, Positive-QTOF	splash10-00di-9030000000-aaff8a67cbd39b4115b4	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Isobutyl-2,4,8,10,12-tetradecapentaenamide 20V, Positive-QTOF	splash10-00di-9000000000-e2934d2bfd0a792a9f60	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Isobutyl-2,4,8,10,12-tetradecapentaenamide 40V, Positive-QTOF	splash10-0ab9-9100000000-921d722ebf9ced984cd9	2016-08-02	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Isobutyl-2,4,8,10,12-tetradecapentaenamide 10V, Positive-QTOF	splash10-00di-4690000000-c3db78701fe88dfa2b8a	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Isobutyl-2,4,8,10,12-tetradecapentaenamide 20V, Positive-QTOF	splash10-0ab9-9110000000-9ecca852880d90639495	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - N-Isobutyl-2,4,8,10,12-tetradecapentaenamide 40V, Positive-QTOF	splash10-05mo-9300000000-d2ce3cf2418365f6d96e	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

FDB003203

KNApSAcK ID

C00039254

Chemspider ID

4477068

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5318518

PDB ID

Not Available

ChEBI ID

Not Available

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
(). 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 N-Isobutyl-2,4,8,10,12-tetradecapentaenamide (HMDB0031184)

MOL for HMDB0031184 (N-Isobutyl-2,4,8,10,12-tetradecapentaenamide)

3D MOL for HMDB0031184 (N-Isobutyl-2,4,8,10,12-tetradecapentaenamide)

3D SDF for HMDB0031184 (N-Isobutyl-2,4,8,10,12-tetradecapentaenamide)

3D-SDF for HMDB0031184 (N-Isobutyl-2,4,8,10,12-tetradecapentaenamide)

PDB for HMDB0031184 (N-Isobutyl-2,4,8,10,12-tetradecapentaenamide)

3D PDB for HMDB0031184 (N-Isobutyl-2,4,8,10,12-tetradecapentaenamide)

SMILES for HMDB0031184 (N-Isobutyl-2,4,8,10,12-tetradecapentaenamide)

INCHI for HMDB0031184 (N-Isobutyl-2,4,8,10,12-tetradecapentaenamide)

Structure for HMDB0031184 (N-Isobutyl-2,4,8,10,12-tetradecapentaenamide)

3D Structure for HMDB0031184 (N-Isobutyl-2,4,8,10,12-tetradecapentaenamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra