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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2011-07-06 11:32:41 UTC

Update Date

2022-03-07 02:51:34 UTC

HMDB ID

HMDB0013648

Secondary Accession Numbers

HMDB13648

Metabolite Identification

Common Name

Palmitoleoylethanolamde

Description

Palmitoleoylethanolamde (POEA), belongs to the class of organic compounds known as N-acylethanolamines. N-Acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine. Thus, palmitoleoylethanolamde is considered to be a fatty amide lipid molecule. Palmitoleoylethanolamde is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral. During abstinence, young adults with a history of alcohol binge drinking had elevated plasma levels of monounsaturated and polyunsaturatedacylethanolamides, specifically oleoylethanolamide (OEA), palmitoleoylethanolamide (POEA), arachidonoylethanolamide (AEA), and dihomo-gamma-linolenoylethanolamide (DGLEA). Changes in these lipids positively correlated with mRNA upregulation of inflammatory markers in peripheral blood mononuclear cells (PBMCs), such as toll-like receptors (TLR4), pro-inflammatory cytokines/chemokines, and cyclooxygenase-2 (PMID: 29178411 ).

Structure

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

HMDB0013648
     RDKit          3D
Palmitoleoylethanolamde
 56 55  0  0  0  0  0  0  0  0999 V2000
   -6.9066    2.5017   -0.8048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7146    1.2651   -0.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2603    0.0391   -0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9682   -0.5741   -0.6500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7872    0.3209   -0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5643   -0.5690   -0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3945    0.2686   -0.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3781    0.0110    0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3760   -1.1835    1.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3947   -2.2525    0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0525   -2.0697    1.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7214   -1.1692    0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2275   -1.0723    0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4819   -0.5317    1.7725 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9493   -0.3983    2.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5519    0.5623    1.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8164    1.2359    0.3099 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9557    0.7048    1.0788 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5852    1.6315    0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.9651    2.2464   -2.0423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3507    2.7462   -1.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -7.2729    0.1484    0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
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M  END


  Mrv1652303262018272D          

 21 20  0  0  0  0            999 V2000
10014.478110016.8181    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.193510016.4058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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  2  4  1  0  0  0  0
  3  5  1  0  0  0  0
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 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013648

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCC\C=C/CCCCCCCC(=O)NCCO

> <INCHI_IDENTIFIER>
InChI=1S/C18H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)19-16-17-20/h7-8,20H,2-6,9-17H2,1H3,(H,19,21)/b8-7-

> <INCHI_KEY>
WFRLANWAASSSFV-FPLPWBNLSA-N

> <FORMULA>
C18H35NO2

> <MOLECULAR_WEIGHT>
297.476

> <EXACT_MASS>
297.266779369

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
38.493366616866986

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z)-N-(2-hydroxyethyl)hexadec-9-enamide

> <ALOGPS_LOGP>
6.07

> <JCHEM_LOGP>
4.621292561

> <ALOGPS_LOGS>
-5.63

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.47384261938588

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.469626555316175

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3086129187290516

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
91.2114

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
7.02e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
palmitoleoyl-EA

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013648
     RDKit          3D
Palmitoleoylethanolamde
 56 55  0  0  0  0  0  0  0  0999 V2000
   -6.9066    2.5017   -0.8048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7146    1.2651   -0.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2603    0.0391   -0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9682   -0.5741   -0.6500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7872    0.3209   -0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5643   -0.5690   -0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3945    0.2686   -0.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3781    0.0110    0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
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    8.9009    1.9709   -2.2238 H   0  0  0  0  0  0  0  0  0  0  0  0
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 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
M  END

HEADER    PROTEIN                                 26-MAR-20   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   26-MAR-20         0                                  
HETATM    1  C   UNK     0    8693.6928698.060   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8695.0288697.291   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8692.3578697.291   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8696.3598698.060   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8691.0268698.060   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8697.6948697.291   0.000  0.00  0.00           C+0
HETATM    7  N   UNK     0    8689.6908697.291   0.000  0.00  0.00           N+0
HETATM    8  O   UNK     0    8691.0268699.599   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0    8699.0288698.060   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8688.3598698.060   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8700.3628697.291   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8687.0248697.291   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8701.6958698.060   0.000  0.00  0.00           C+0
HETATM   14  O   UNK     0    8685.6858698.060   0.000  0.00  0.00           O+0
HETATM   15  C   UNK     0    8703.2368698.060   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8704.5698697.291   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8705.9038698.060   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8707.2388697.291   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0    8708.5718698.060   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0    8709.9058697.291   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8711.2438698.060   0.000  0.00  0.00           C+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7    8                                                  
CONECT    6    4    9                                                       
CONECT    7    5   10                                                       
CONECT    8    5                                                            
CONECT    9    6   11                                                       
CONECT   10    7   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12                                                            
CONECT   15   13   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   18                                                       
CONECT   18   17   19                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20                                                            
MASTER        0    0    0    0    0    0    0    0   21    0   40    0
END

COMPND    HMDB0013648
HETATM    1  C1  UNL     1      -6.907   2.502  -0.805  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.715   1.265  -0.963  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.260   0.039  -0.283  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.968  -0.574  -0.650  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.787   0.321  -0.433  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.564  -0.569  -0.832  1.00  0.00           C  
HETATM    7  C7  UNL     1      -2.394   0.269  -0.633  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.378   0.011   0.201  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.376  -1.183   1.007  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.395  -2.252   0.888  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.053  -2.070   1.122  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.721  -1.169   0.166  1.00  0.00           C  
HETATM   13  C13 UNL     1       3.228  -1.072   0.406  1.00  0.00           C  
HETATM   14  C14 UNL     1       3.482  -0.532   1.772  1.00  0.00           C  
HETATM   15  C15 UNL     1       4.949  -0.398   2.014  1.00  0.00           C  
HETATM   16  C16 UNL     1       5.552   0.562   1.082  1.00  0.00           C  
HETATM   17  O1  UNL     1       4.816   1.236   0.310  1.00  0.00           O  
HETATM   18  N1  UNL     1       6.956   0.705   1.079  1.00  0.00           N  
HETATM   19  C17 UNL     1       7.585   1.632   0.180  1.00  0.00           C  
HETATM   20  C18 UNL     1       7.314   1.295  -1.247  1.00  0.00           C  
HETATM   21  O2  UNL     1       7.965   2.246  -2.042  1.00  0.00           O  
HETATM   22  H1  UNL     1      -6.351   2.746  -1.730  1.00  0.00           H  
HETATM   23  H2  UNL     1      -6.277   2.484   0.107  1.00  0.00           H  
HETATM   24  H3  UNL     1      -7.613   3.408  -0.710  1.00  0.00           H  
HETATM   25  H4  UNL     1      -7.851   1.024  -2.054  1.00  0.00           H  
HETATM   26  H5  UNL     1      -8.769   1.492  -0.620  1.00  0.00           H  
HETATM   27  H6  UNL     1      -8.044  -0.782  -0.440  1.00  0.00           H  
HETATM   28  H7  UNL     1      -7.273   0.148   0.846  1.00  0.00           H  
HETATM   29  H8  UNL     1      -5.956  -0.967  -1.707  1.00  0.00           H  
HETATM   30  H9  UNL     1      -5.860  -1.522  -0.037  1.00  0.00           H  
HETATM   31  H10 UNL     1      -4.656   0.503   0.643  1.00  0.00           H  
HETATM   32  H11 UNL     1      -4.765   1.212  -1.077  1.00  0.00           H  
HETATM   33  H12 UNL     1      -3.717  -0.739  -1.930  1.00  0.00           H  
HETATM   34  H13 UNL     1      -3.687  -1.462  -0.244  1.00  0.00           H  
HETATM   35  H14 UNL     1      -2.329   1.196  -1.213  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.574   0.782   0.267  1.00  0.00           H  
HETATM   37  H16 UNL     1      -1.203  -0.768   2.099  1.00  0.00           H  
HETATM   38  H17 UNL     1      -2.432  -1.595   1.174  1.00  0.00           H  
HETATM   39  H18 UNL     1      -0.701  -3.060   1.663  1.00  0.00           H  
HETATM   40  H19 UNL     1      -0.461  -2.787  -0.127  1.00  0.00           H  
HETATM   41  H20 UNL     1       1.201  -1.745   2.203  1.00  0.00           H  
HETATM   42  H21 UNL     1       1.526  -3.103   1.038  1.00  0.00           H  
HETATM   43  H22 UNL     1       1.282  -0.181   0.124  1.00  0.00           H  
HETATM   44  H23 UNL     1       1.581  -1.620  -0.860  1.00  0.00           H  
HETATM   45  H24 UNL     1       3.663  -0.520  -0.433  1.00  0.00           H  
HETATM   46  H25 UNL     1       3.611  -2.130   0.297  1.00  0.00           H  
HETATM   47  H26 UNL     1       2.983   0.471   1.845  1.00  0.00           H  
HETATM   48  H27 UNL     1       3.024  -1.228   2.516  1.00  0.00           H  
HETATM   49  H28 UNL     1       5.107  -0.123   3.082  1.00  0.00           H  
HETATM   50  H29 UNL     1       5.392  -1.424   1.889  1.00  0.00           H  
HETATM   51  H30 UNL     1       7.534   0.139   1.727  1.00  0.00           H  
HETATM   52  H31 UNL     1       7.196   2.664   0.408  1.00  0.00           H  
HETATM   53  H32 UNL     1       8.687   1.682   0.397  1.00  0.00           H  
HETATM   54  H33 UNL     1       7.701   0.272  -1.447  1.00  0.00           H  
HETATM   55  H34 UNL     1       6.253   1.303  -1.475  1.00  0.00           H  
HETATM   56  H35 UNL     1       8.901   1.971  -2.224  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   31   32
CONECT    6    7   33   34
CONECT    7    8    8   35
CONECT    8    9   36
CONECT    9   10   37   38
CONECT   10   11   39   40
CONECT   11   12   41   42
CONECT   12   13   43   44
CONECT   13   14   45   46
CONECT   14   15   47   48
CONECT   15   16   49   50
CONECT   16   17   17   18
CONECT   18   19   51
CONECT   19   20   52   53
CONECT   20   21   54   55
CONECT   21   56
END

HMDB0013648
     RDKit          3D
Palmitoleoylethanolamde
 56 55  0  0  0  0  0  0  0  0999 V2000
   -6.9066    2.5017   -0.8048 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.7146    1.2651   -0.9630 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2603    0.0391   -0.2831 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9682   -0.5741   -0.6500 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7872    0.3209   -0.4328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5643   -0.5690   -0.8315 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3945    0.2686   -0.6332 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3781    0.0110    0.2008 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3760   -1.1835    1.0068 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3947   -2.2525    0.8878 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0525   -2.0697    1.1216 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7214   -1.1692    0.1663 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2275   -1.0723    0.4060 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4819   -0.5317    1.7725 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9493   -0.3983    2.0137 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5519    0.5623    1.0820 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8164    1.2359    0.3099 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.9557    0.7048    1.0788 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.5852    1.6315    0.1801 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3136    1.2949   -1.2474 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9651    2.2464   -2.0423 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3507    2.7462   -1.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.2765    2.4836    0.1072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6128    3.4076   -0.7102 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8507    1.0238   -2.0543 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7694    1.4921   -0.6201 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0440   -0.7823   -0.4396 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2729    0.1484    0.8457 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.9564   -0.9673   -1.7075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8596   -1.5223   -0.0371 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6560    0.5030    0.6431 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7653    1.2117   -1.0768 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7168   -0.7388   -1.9305 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6875   -1.4620   -0.2441 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3288    1.1955   -1.2130 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5737    0.7819    0.2667 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2035   -0.7684    2.0990 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4321   -1.5950    1.1741 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7006   -3.0595    1.6632 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4609   -2.7875   -0.1265 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2010   -1.7453    2.2028 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5259   -3.1034    1.0379 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2825   -0.1808    0.1241 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5805   -1.6199   -0.8598 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6632   -0.5201   -0.4333 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6113   -2.1301    0.2971 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9828    0.4707    1.8446 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0241   -1.2280    2.5164 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1068   -0.1229    3.0815 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3916   -1.4236    1.8894 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5344    0.1388    1.7271 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.1962    2.6640    0.4081 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6866    1.6819    0.3972 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7009    0.2721   -1.4474 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2532    1.3029   -1.4752 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.9009    1.9709   -2.2238 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  1  0
  5  6  1  0
  6  7  1  0
  7  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  2  0
 16 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 10 40  1  0
 11 41  1  0
 11 42  1  0
 12 43  1  0
 12 44  1  0
 13 45  1  0
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 15 50  1  0
 18 51  1  0
 19 52  1  0
 19 53  1  0
 20 54  1  0
 20 55  1  0
 21 56  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(Z)-Hexadec-9-enoyl ethanolamide	ChEBI
N-(2-Hydroxyethyl)palmitoleylamide	ChEBI
N-(9Z-Hexadecenoyl) ethanolamine	ChEBI
N-(9Z-Hexadecenoyl)-ethanolamine	ChEBI
Palmitoleoyl-ea	ChEBI
POEA	ChEBI
Polyoxyethyleneamine	MeSH
N-(9Z-Hexadecenoyl)-ethanolamide	HMDB
Palmitoleoyl-ethanolamide	HMDB
Palmitoleoyl-ethanolamine	HMDB
(9Z)-N-(2-Hydroxyethyl)-9-hexadecenamide	HMDB
Palmitoleoyl ethanolamide	HMDB

Chemical Formula

C₁₈H₃₅NO₂

Average Molecular Weight

297.476

Monoisotopic Molecular Weight

297.266779369

IUPAC Name

(9Z)-N-(2-hydroxyethyl)hexadec-9-enamide

Traditional Name

palmitoleoyl-EA

CAS Registry Number

94421-67-7

SMILES

CCCCCC\C=C/CCCCCCCC(=O)NCCO

InChI Identifier

InChI=1S/C18H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-18(21)19-16-17-20/h7-8,20H,2-6,9-17H2,1H3,(H,19,21)/b8-7-

InChI Key

WFRLANWAASSSFV-FPLPWBNLSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as n-acylethanolamines. N-acylethanolamines are compounds containing an N-acyethanolamine moiety, which is characterized by an acyl group is linked to the nitrogen atom of ethanolamine.

Kingdom

Organic compounds

Super Class

Organic nitrogen compounds

Class

Organonitrogen compounds

Sub Class

Amines

Direct Parent

N-acylethanolamines

Alternative Parents

Substituents

N-acylethanolamine
Fatty amide
N-acyl-amine
Fatty acyl
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Alcohol
Organooxygen compound
Primary alcohol
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organic oxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

N-(monounsaturated fatty acyl)ethanolamine (CHEBI:71465 )
N-(long-chain-acyl)ethanolamine (CHEBI:71465 )
endocannabinoid (CHEBI:71465 )
N-acyl ethanolamines (endocannabinoids) (LMFA08040043 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0013648)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 29178411)

Cellular substructure

Extracellular (HMDB: HMDB0013648)
Membrane (HMDB: HMDB0013648)

Source

Endogenous

Endogenous (HMDB: HMDB0013648)

Exogenous

Food

Food (HMDB: HMDB0013648)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0013648)

Role

Biological role

Energy source (HMDB: HMDB0013648)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013648)

Emulsifier (HMDB: HMDB0013648)

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0007 g/L	ALOGPS
logP	6.07	ALOGPS
logP	4.62	ChemAxon
logS	-5.6	ALOGPS
pKa (Strongest Acidic)	15.47	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	91.21 m³·mol⁻¹	ChemAxon
Polarizability	38.49 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	179.154	31661259
DarkChem	[M-H]-	181.187	31661259
DeepCCS	[M+H]+	181.62	30932474
DeepCCS	[M-H]-	178.98	30932474
DeepCCS	[M-2H]-	213.726	30932474
DeepCCS	[M+Na]+	190.016	30932474
AllCCS	[M+H]+	181.0	32859911
AllCCS	[M+H-H2O]+	178.1	32859911
AllCCS	[M+NH4]+	183.6	32859911
AllCCS	[M+Na]+	184.4	32859911
AllCCS	[M-H]-	181.0	32859911
AllCCS	[M+Na-2H]-	182.6	32859911
AllCCS	[M+HCOO]-	184.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Palmitoleoylethanolamde	CCCCCC\C=C/CCCCCCCC(=O)NCCO	2919.9	Standard polar	33892256
Palmitoleoylethanolamde	CCCCCC\C=C/CCCCCCCC(=O)NCCO	2326.2	Standard non polar	33892256
Palmitoleoylethanolamde	CCCCCC\C=C/CCCCCCCC(=O)NCCO	2487.3	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Palmitoleoylethanolamde,1TMS,isomer #1	CCCCCC/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C	2518.0	Semi standard non polar	33892256
Palmitoleoylethanolamde,1TMS,isomer #2	CCCCCC/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C	2477.9	Semi standard non polar	33892256
Palmitoleoylethanolamde,2TMS,isomer #1	CCCCCC/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2520.2	Semi standard non polar	33892256
Palmitoleoylethanolamde,2TMS,isomer #1	CCCCCC/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2558.9	Standard non polar	33892256
Palmitoleoylethanolamde,2TMS,isomer #1	CCCCCC/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2515.8	Standard polar	33892256
Palmitoleoylethanolamde,1TBDMS,isomer #1	CCCCCC/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C(C)(C)C	2735.1	Semi standard non polar	33892256
Palmitoleoylethanolamde,1TBDMS,isomer #2	CCCCCC/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C	2692.9	Semi standard non polar	33892256
Palmitoleoylethanolamde,2TBDMS,isomer #1	CCCCCC/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2978.4	Semi standard non polar	33892256
Palmitoleoylethanolamde,2TBDMS,isomer #1	CCCCCC/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2895.9	Standard non polar	33892256
Palmitoleoylethanolamde,2TBDMS,isomer #1	CCCCCC/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2713.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Palmitoleoylethanolamde GC-MS (Non-derivatized) - 70eV, Positive	splash10-006t-9850000000-dca871694e1453ee1290	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Palmitoleoylethanolamde GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-9432000000-461ac4f924d74371dcfa	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Palmitoleoylethanolamde GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Palmitoleoylethanolamde 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleoylethanolamde 10V, Positive-QTOF	splash10-0002-0090000000-431ef9175cd6e2c98ac5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleoylethanolamde 20V, Positive-QTOF	splash10-001j-3090000000-fd112625084534fd104f	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Palmitoleoylethanolamde 40V, Positive-QTOF	splash10-001i-9000000000-c67f4ac6eb06f01e12ff	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleoylethanolamde 10V, Positive-QTOF	splash10-01ot-3090000000-d6769586b97d92aec922	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleoylethanolamde 20V, Positive-QTOF	splash10-03dl-9130000000-e2b3de7dda39a1a2b8e7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleoylethanolamde 40V, Positive-QTOF	splash10-01ox-9310000000-3a6ec9ee35e9c5b6fcb5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleoylethanolamde 10V, Negative-QTOF	splash10-0002-0090000000-2bc9024817a3bec1dab5	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleoylethanolamde 20V, Negative-QTOF	splash10-01r2-4090000000-29e8051940c6da6e4f7f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleoylethanolamde 40V, Negative-QTOF	splash10-0006-9010000000-5d6e43f9124267c45344	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleoylethanolamde 10V, Positive-QTOF	splash10-01ot-9080000000-d5b6efef796a3944fdee	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleoylethanolamde 20V, Positive-QTOF	splash10-03dl-9000000000-580ee14b795a28da936b	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleoylethanolamde 40V, Positive-QTOF	splash10-01ox-9000000000-0796fb6e81f9d4eed35f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleoylethanolamde 10V, Negative-QTOF	splash10-0002-0090000000-69f5cee9787e872ffdd7	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleoylethanolamde 20V, Negative-QTOF	splash10-0002-3190000000-42b64e70a801d7da5829	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Palmitoleoylethanolamde 40V, Negative-QTOF	splash10-059f-9110000000-ab8fbfe293d1e35072db	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29178411	details

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

FDB029618

KNApSAcK ID

Not Available

Chemspider ID

8011589

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

9835868

PDB ID

Not Available

ChEBI ID

71465

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

Syed SK, Bui HH, Beavers LS, Farb TB, Ficorilli J, Chesterfield AK, Kuo MS, Bokvist K, Barrett DG, Efanov AM: Regulation of GPR119 receptor activity with endocannabinoid-like lipids. Am J Physiol Endocrinol Metab. 2012 Dec 15;303(12):E1469-78. doi: 10.1152/ajpendo.00269.2012. Epub 2012 Oct 16. [PubMed:23074242 ]
Anton M, Rodriguez-Gonzalez A, Rodriguez-Rojo IC, Pastor A, Correas A, Serrano A, Ballesta A, Alen F, Gomez de Heras R, de la Torre R, Rodriguez de Fonseca F, Orio L: Increased plasma oleoylethanolamide and palmitoleoylethanolamide levels correlate with inflammatory changes in alcohol binge drinkers: the case of HMGB1 in women. Addict Biol. 2018 Nov;23(6):1242-1250. doi: 10.1111/adb.12580. Epub 2017 Nov 27. [PubMed:29178411 ]

Showing metabocard for Palmitoleoylethanolamde (HMDB0013648)

MOL for HMDB0013648 (Palmitoleoylethanolamde)

3D MOL for HMDB0013648 (Palmitoleoylethanolamde)

3D SDF for HMDB0013648 (Palmitoleoylethanolamde)

3D-SDF for HMDB0013648 (Palmitoleoylethanolamde)

PDB for HMDB0013648 (Palmitoleoylethanolamde)

3D PDB for HMDB0013648 (Palmitoleoylethanolamde)

SMILES for HMDB0013648 (Palmitoleoylethanolamde)

INCHI for HMDB0013648 (Palmitoleoylethanolamde)

Structure for HMDB0013648 (Palmitoleoylethanolamde)

3D Structure for HMDB0013648 (Palmitoleoylethanolamde)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra