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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 14:17:37 UTC

Update Date

2022-03-07 02:49:13 UTC

HMDB ID

HMDB0002117

Secondary Accession Numbers

HMDB02117

Metabolite Identification

Common Name

Oleamide

Description

Oleamide is an amide of the fatty acid oleic acid. It is an endogenous substance: it occurs naturally in the body of animals. It accumulates in the cerebrospinal fluid during sleep deprivation and induces sleep in animals. It is being studied as a potential medical treatment for mood and sleep disorders, and cannabinoid-regulated depression. The mechanism of action of oleamide's sleep inducing effects is an area of current research. It is likely that oleamide interacts with multiple neurotransmitter systems. Oleamide is structurally related to the endogenous cannabinoid anandamide, and has the ability to bind to the CB1 receptor as a full agonist.

Structure

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

HMDB0002117
     RDKit          3D
Oleamide
 55 54  0  0  0  0  0  0  0  0999 V2000
    6.7161   -2.6240   -0.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4782   -1.7023   -0.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5424   -0.9400   -1.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4182   -0.0120   -1.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1948    1.1371   -1.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9349    0.9763    0.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7492    0.1294    0.7239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4401    0.6541    0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0745    1.9805    0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0064    2.2753    1.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0221    1.3299    1.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3983    1.6366    1.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3228    0.5567    1.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7275    0.7396    1.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8051    0.6999   -0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3113   -0.5895   -0.8664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0909   -1.7624   -0.3744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5186   -1.7333   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3208   -2.8066   -0.2055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0420   -0.8307   -1.3899 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5470   -2.0387   -0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4690   -3.4910   -1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0001   -2.8593    0.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4342   -1.1406    0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5813   -2.3897   -0.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5495   -0.4439   -1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5009   -1.7150   -2.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4497    0.3676   -3.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4802   -0.6817   -1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1261    1.8046   -1.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3844    1.8257   -1.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5814    2.0423    0.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8080    0.8464    1.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316    0.0728    1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8468   -0.8965    0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5663    0.6647   -0.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6737   -0.0900    0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7600    2.8502    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1980    3.3408    1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7807    0.3039    1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1280    1.3399    2.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3288    1.5475    0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171    2.6176    1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3219    0.6148    2.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9745   -0.4547    1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3429   -0.0869    1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1612    1.7101    1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8402    0.9706   -0.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1755    1.5106   -0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3206   -0.5785   -1.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2278   -0.6881   -0.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6730   -2.6786   -0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9201   -1.8582    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8123   -3.4254   -0.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4500   -3.0156    0.7939 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  1  0
  8  9  1  0
  9 10  2  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  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 19 54  1  0
 19 55  1  0
M  END


  Mrv0541 02231219222D          

 20 19  0  0  0  0            999 V2000
    6.5776  -11.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4026  -11.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8151  -12.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6401  -12.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0526  -13.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8776  -13.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.2901  -14.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.1151  -14.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5276  -14.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.3526  -14.7610    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7651  -14.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.5901  -14.0465    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.0026  -13.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8276  -13.3321    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.2401  -12.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0651  -12.6175    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4776  -11.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3026  -11.9031    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.7151  -12.6175    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.7151  -11.1886    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  1  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  1  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  1  0  0  0  0
 20 18  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0002117

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCCCCC\C=C/CCCCCCCC(N)=O

> <INCHI_IDENTIFIER>
InChI=1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9-

> <INCHI_KEY>
FATBGEAMYMYZAF-KTKRTIGZSA-N

> <FORMULA>
C18H35NO

> <MOLECULAR_WEIGHT>
281.4766

> <EXACT_MASS>
281.271864747

> <JCHEM_ACCEPTOR_COUNT>
1

> <JCHEM_AVERAGE_POLARIZABILITY>
37.43753172718946

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(9Z)-octadec-9-enamide

> <ALOGPS_LOGP>
7.19

> <JCHEM_LOGP>
5.976855837333334

> <ALOGPS_LOGS>
-6.59

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
16.920466133717532

> <JCHEM_PKA_STRONGEST_BASIC>
-0.5790839094389891

> <JCHEM_POLAR_SURFACE_AREA>
43.09

> <JCHEM_REFRACTIVITY>
89.22439999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.31e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oleamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002117
     RDKit          3D
Oleamide
 55 54  0  0  0  0  0  0  0  0999 V2000
    6.7161   -2.6240   -0.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4782   -1.7023   -0.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5424   -0.9400   -1.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4182   -0.0120   -1.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1948    1.1371   -1.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9349    0.9763    0.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7492    0.1294    0.7239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4401    0.6541    0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0745    1.9805    0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0064    2.2753    1.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0221    1.3299    1.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3983    1.6366    1.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3228    0.5567    1.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7275    0.7396    1.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8051    0.6999   -0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3113   -0.5895   -0.8664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0909   -1.7624   -0.3744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5186   -1.7333   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3208   -2.8066   -0.2055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0420   -0.8307   -1.3899 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5470   -2.0387   -0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4690   -3.4910   -1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0001   -2.8593    0.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4342   -1.1406    0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5813   -2.3897   -0.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5495   -0.4439   -1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5009   -1.7150   -2.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4497    0.3676   -3.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4802   -0.6817   -1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1261    1.8046   -1.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3844    1.8257   -1.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5814    2.0423    0.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8080    0.8464    1.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316    0.0728    1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8468   -0.8965    0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5663    0.6647   -0.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6737   -0.0900    0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7600    2.8502    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1980    3.3408    1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7807    0.3039    1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1280    1.3399    2.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3288    1.5475    0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171    2.6176    1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3219    0.6148    2.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9745   -0.4547    1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3429   -0.0869    1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1612    1.7101    1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8402    0.9706   -0.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1755    1.5106   -0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3206   -0.5785   -1.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2278   -0.6881   -0.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6730   -2.6786   -0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9201   -1.8582    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8123   -3.4254   -0.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4500   -3.0156    0.7939 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  1  0
  8  9  1  0
  9 10  2  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  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 19 54  1  0
 19 55  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  C   UNK     0      12.278 -22.219   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      13.818 -22.219   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      14.588 -23.553   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      16.128 -23.553   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      16.898 -24.887   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      18.438 -24.887   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      19.208 -26.220   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      20.748 -26.220   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      21.518 -27.554   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      23.058 -27.554   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.828 -26.220   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      25.368 -26.220   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      26.138 -24.887   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.678 -24.887   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.448 -23.553   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.988 -23.553   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.758 -22.219   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.298 -22.219   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0      33.068 -23.553   0.000  0.00  0.00           N+0
HETATM   20  O   UNK     0      33.068 -20.885   0.000  0.00  0.00           O+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                                                       
CONECT   15   14   16                                                       
CONECT   16   15   17                                                       
CONECT   17   16   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    HMDB0002117
HETATM    1  C1  UNL     1       6.716  -2.624  -0.474  1.00  0.00           C  
HETATM    2  C2  UNL     1       5.478  -1.702  -0.476  1.00  0.00           C  
HETATM    3  C3  UNL     1       5.542  -0.940  -1.751  1.00  0.00           C  
HETATM    4  C4  UNL     1       4.418  -0.012  -1.948  1.00  0.00           C  
HETATM    5  C5  UNL     1       4.195   1.137  -1.074  1.00  0.00           C  
HETATM    6  C6  UNL     1       3.935   0.976   0.373  1.00  0.00           C  
HETATM    7  C7  UNL     1       2.749   0.129   0.724  1.00  0.00           C  
HETATM    8  C8  UNL     1       1.440   0.654   0.177  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.075   1.981   0.637  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.006   2.275   1.311  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.022   1.330   1.714  1.00  0.00           C  
HETATM   12  C12 UNL     1      -2.398   1.637   1.147  1.00  0.00           C  
HETATM   13  C13 UNL     1      -3.323   0.557   1.667  1.00  0.00           C  
HETATM   14  C14 UNL     1      -4.728   0.740   1.186  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.805   0.700  -0.305  1.00  0.00           C  
HETATM   16  C16 UNL     1      -4.311  -0.590  -0.866  1.00  0.00           C  
HETATM   17  C17 UNL     1      -5.091  -1.762  -0.374  1.00  0.00           C  
HETATM   18  C18 UNL     1      -6.519  -1.733  -0.706  1.00  0.00           C  
HETATM   19  N1  UNL     1      -7.321  -2.807  -0.206  1.00  0.00           N  
HETATM   20  O1  UNL     1      -7.042  -0.831  -1.390  1.00  0.00           O  
HETATM   21  H1  UNL     1       7.547  -2.039  -0.942  1.00  0.00           H  
HETATM   22  H2  UNL     1       6.469  -3.491  -1.094  1.00  0.00           H  
HETATM   23  H3  UNL     1       7.000  -2.859   0.551  1.00  0.00           H  
HETATM   24  H4  UNL     1       5.434  -1.141   0.447  1.00  0.00           H  
HETATM   25  H5  UNL     1       4.581  -2.390  -0.541  1.00  0.00           H  
HETATM   26  H6  UNL     1       6.549  -0.444  -1.885  1.00  0.00           H  
HETATM   27  H7  UNL     1       5.501  -1.715  -2.582  1.00  0.00           H  
HETATM   28  H8  UNL     1       4.450   0.368  -3.030  1.00  0.00           H  
HETATM   29  H9  UNL     1       3.480  -0.682  -1.984  1.00  0.00           H  
HETATM   30  H10 UNL     1       5.126   1.805  -1.170  1.00  0.00           H  
HETATM   31  H11 UNL     1       3.384   1.826  -1.496  1.00  0.00           H  
HETATM   32  H12 UNL     1       3.581   2.042   0.719  1.00  0.00           H  
HETATM   33  H13 UNL     1       4.808   0.846   1.031  1.00  0.00           H  
HETATM   34  H14 UNL     1       2.632   0.073   1.822  1.00  0.00           H  
HETATM   35  H15 UNL     1       2.847  -0.897   0.320  1.00  0.00           H  
HETATM   36  H16 UNL     1       1.566   0.665  -0.953  1.00  0.00           H  
HETATM   37  H17 UNL     1       0.674  -0.090   0.392  1.00  0.00           H  
HETATM   38  H18 UNL     1       1.760   2.850   0.406  1.00  0.00           H  
HETATM   39  H19 UNL     1      -0.198   3.341   1.621  1.00  0.00           H  
HETATM   40  H20 UNL     1      -0.781   0.304   1.441  1.00  0.00           H  
HETATM   41  H21 UNL     1      -1.128   1.340   2.847  1.00  0.00           H  
HETATM   42  H22 UNL     1      -2.329   1.548   0.052  1.00  0.00           H  
HETATM   43  H23 UNL     1      -2.717   2.618   1.515  1.00  0.00           H  
HETATM   44  H24 UNL     1      -3.322   0.615   2.794  1.00  0.00           H  
HETATM   45  H25 UNL     1      -2.974  -0.455   1.407  1.00  0.00           H  
HETATM   46  H26 UNL     1      -5.343  -0.087   1.594  1.00  0.00           H  
HETATM   47  H27 UNL     1      -5.161   1.710   1.538  1.00  0.00           H  
HETATM   48  H28 UNL     1      -5.840   0.971  -0.592  1.00  0.00           H  
HETATM   49  H29 UNL     1      -4.176   1.511  -0.781  1.00  0.00           H  
HETATM   50  H30 UNL     1      -4.321  -0.579  -1.986  1.00  0.00           H  
HETATM   51  H31 UNL     1      -3.228  -0.688  -0.606  1.00  0.00           H  
HETATM   52  H32 UNL     1      -4.673  -2.679  -0.856  1.00  0.00           H  
HETATM   53  H33 UNL     1      -4.920  -1.858   0.729  1.00  0.00           H  
HETATM   54  H34 UNL     1      -7.812  -3.425  -0.887  1.00  0.00           H  
HETATM   55  H35 UNL     1      -7.450  -3.016   0.794  1.00  0.00           H  
CONECT    1    2   21   22   23
CONECT    2    3   24   25
CONECT    3    4   26   27
CONECT    4    5   28   29
CONECT    5    6   30   31
CONECT    6    7   32   33
CONECT    7    8   34   35
CONECT    8    9   36   37
CONECT    9   10   10   38
CONECT   10   11   39
CONECT   11   12   40   41
CONECT   12   13   42   43
CONECT   13   14   44   45
CONECT   14   15   46   47
CONECT   15   16   48   49
CONECT   16   17   50   51
CONECT   17   18   52   53
CONECT   18   19   20   20
CONECT   19   54   55
END

HMDB0002117
     RDKit          3D
Oleamide
 55 54  0  0  0  0  0  0  0  0999 V2000
    6.7161   -2.6240   -0.4735 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4782   -1.7023   -0.4759 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5424   -0.9400   -1.7514 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4182   -0.0120   -1.9482 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1948    1.1371   -1.0744 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.9349    0.9763    0.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7492    0.1294    0.7239 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4401    0.6541    0.1771 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0745    1.9805    0.6372 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0064    2.2753    1.3110 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0221    1.3299    1.7137 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3983    1.6366    1.1474 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3228    0.5567    1.6675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7275    0.7396    1.1856 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8051    0.6999   -0.3053 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3113   -0.5895   -0.8664 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0909   -1.7624   -0.3744 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5186   -1.7333   -0.7058 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3208   -2.8066   -0.2055 N   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0420   -0.8307   -1.3899 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.5470   -2.0387   -0.9422 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4690   -3.4910   -1.0944 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.0001   -2.8593    0.5508 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.4342   -1.1406    0.4466 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5813   -2.3897   -0.5413 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.5495   -0.4439   -1.8851 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5009   -1.7150   -2.5817 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4497    0.3676   -3.0299 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4802   -0.6817   -1.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1261    1.8046   -1.1695 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3844    1.8257   -1.4955 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5814    2.0423    0.7191 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8080    0.8464    1.0305 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6316    0.0728    1.8219 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8468   -0.8965    0.3196 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5663    0.6647   -0.9532 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6737   -0.0900    0.3918 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7600    2.8502    0.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1980    3.3408    1.6214 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7807    0.3039    1.4414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1280    1.3399    2.8468 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3288    1.5475    0.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7171    2.6176    1.5148 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3219    0.6148    2.7936 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9745   -0.4547    1.4072 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3429   -0.0869    1.5941 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1612    1.7101    1.5383 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8402    0.9706   -0.5919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1755    1.5106   -0.7813 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3206   -0.5785   -1.9857 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2278   -0.6881   -0.6065 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6730   -2.6786   -0.8557 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9201   -1.8582    0.7290 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8123   -3.4254   -0.8865 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4500   -3.0156    0.7939 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  1  0
  8  9  1  0
  9 10  2  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  1  0
 17 18  1  0
 18 19  1  0
 18 20  2  0
  1 21  1  0
  1 22  1  0
  1 23  1  0
  2 24  1  0
  2 25  1  0
  3 26  1  0
  3 27  1  0
  4 28  1  0
  4 29  1  0
  5 30  1  0
  5 31  1  0
  6 32  1  0
  6 33  1  0
  7 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 12 43  1  0
 13 44  1  0
 13 45  1  0
 14 46  1  0
 14 47  1  0
 15 48  1  0
 15 49  1  0
 16 50  1  0
 16 51  1  0
 17 52  1  0
 17 53  1  0
 19 54  1  0
 19 55  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(9Z)-9-Octadecenamide	ChEBI
(9Z)-Octadecenamide	ChEBI
(Z)-9-Octadecenamide	ChEBI
(Z)-Octadec-9-enoic acid amide	ChEBI
9-Octadecenamide	ChEBI
9Z-Octadecenamide	ChEBI
cis-9,10-Octadecenoamide	ChEBI
Oleic acid amide	ChEBI
Oleyl amide	ChEBI
Oleylamide	ChEBI
(Z)-Octadec-9-enoate amide	Generator
Oleate amide	Generator
(9Z)-Octadec-9-enamide	HMDB
(cis)-9-Octadecenoate	HMDB
(cis)-9-Octadecenoic acid	HMDB
(cis)-9-Octadecenoic acid amide	HMDB
14C-Labeled oleamide	HMDB
9,10-Octadecenamide	HMDB
Adogen 73	HMDB
Aliphatic amide	HMDB
Amide O	HMDB
Armid O	HMDB
Armoslip CP	HMDB
Crodamide O	HMDB
Crodamide or	HMDB
Diamide O 200	HMDB
Diamit O 200	HMDB
Elaidoylamide	HMDB
ELD	HMDB
Kemamide O	HMDB
Octadecene amide	HMDB
Petrac slip-eze	HMDB
Polydis TR 121	HMDB
Slip-eze	HMDB
Tocris-0878	HMDB
trans-9,10-Octadecenoamide	HMDB
Unislip 1759	HMDB
Oleylamide, (e)-isomer	HMDB

Chemical Formula

C₁₈H₃₅NO

Average Molecular Weight

281.4766

Monoisotopic Molecular Weight

281.271864747

IUPAC Name

(9Z)-octadec-9-enamide

Traditional Name

oleamide

CAS Registry Number

301-02-0

SMILES

CCCCCCCC\C=C/CCCCCCCC(N)=O

InChI Identifier

InChI=1S/C18H35NO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18(19)20/h9-10H,2-8,11-17H2,1H3,(H2,19,20)/b10-9-

InChI Key

FATBGEAMYMYZAF-KTKRTIGZSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty amides. These are carboxylic acid amide derivatives of fatty acids, that are formed from a fatty acid and an amine.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty amides

Direct Parent

Fatty amides

Alternative Parents

Substituents

Fatty amide
Primary 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

fatty amide (CHEBI:116314 )
Primary amides (LMFA08010004 )

Ontology

Not Available

Non-excretory biofluid

Blood (PMID: 25105552)

Excreta

Feces (PMID: 27543620)

Cellular substructure

Extracellular (HMDB: HMDB0002117)
Membrane (HMDB: HMDB0002117)

Squab (FooDB: FOOD00481)
Pheasant (FooDB: FOOD00430)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Emu (FooDB: FOOD00360)
Mallard duck (FooDB: FOOD00353)
Guinea hen (FooDB: FOOD00373)
Greylag goose (FooDB: FOOD00368)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Equine

Horse (FooDB: FOOD00378)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	102 - 104 °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	7.3e-05 g/L	ALOGPS
logP	7.19	ALOGPS
logP	5.98	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	16.92	ChemAxon
pKa (Strongest Basic)	-0.58	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	1	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	43.09 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	89.22 m³·mol⁻¹	ChemAxon
Polarizability	37.44 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	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]+	176.653	31661259
DarkChem	[M-H]-	177.047	31661259
DeepCCS	[M+H]+	184.528	30932474
DeepCCS	[M-H]-	180.677	30932474
DeepCCS	[M-2H]-	217.081	30932474
DeepCCS	[M+Na]+	193.343	30932474
AllCCS	[M+H]+	179.8	32859911
AllCCS	[M+H-H2O]+	176.8	32859911
AllCCS	[M+NH4]+	182.6	32859911
AllCCS	[M+Na]+	183.4	32859911
AllCCS	[M-H]-	179.4	32859911
AllCCS	[M+Na-2H]-	180.9	32859911
AllCCS	[M+HCOO]-	182.8	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Oleamide	CCCCCCCC\C=C/CCCCCCCC(N)=O	3276.5	Standard polar	33892256
Oleamide	CCCCCCCC\C=C/CCCCCCCC(N)=O	2230.9	Standard non polar	33892256
Oleamide	CCCCCCCC\C=C/CCCCCCCC(N)=O	2372.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Oleamide,1TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N[Si](C)(C)C	2415.2	Semi standard non polar	33892256
Oleamide,1TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N[Si](C)(C)C	2306.4	Standard non polar	33892256
Oleamide,1TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N[Si](C)(C)C	2513.8	Standard polar	33892256
Oleamide,2TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C	2488.2	Semi standard non polar	33892256
Oleamide,2TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C	2461.5	Standard non polar	33892256
Oleamide,2TMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N([Si](C)(C)C)[Si](C)(C)C	2360.1	Standard polar	33892256
Oleamide,1TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N[Si](C)(C)C(C)(C)C	2591.7	Semi standard non polar	33892256
Oleamide,1TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N[Si](C)(C)C(C)(C)C	2515.0	Standard non polar	33892256
Oleamide,1TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N[Si](C)(C)C(C)(C)C	2577.1	Standard polar	33892256
Oleamide,2TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2926.8	Semi standard non polar	33892256
Oleamide,2TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2809.1	Standard non polar	33892256
Oleamide,2TBDMS,isomer #1	CCCCCCCC/C=C\CCCCCCCC(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2561.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental GC-MS	GC-MS Spectrum - Oleamide EI-B (Non-derivatized)	splash10-0a4i-9000000000-82979114d02d916c656e	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Oleamide EI-B (Non-derivatized)	splash10-0a4i-9000000000-97b84b2740298afd1c1d	2017-09-12	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Oleamide EI-B (Non-derivatized)	splash10-0a4i-9000000000-82979114d02d916c656e	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Oleamide EI-B (Non-derivatized)	splash10-0a4i-9000000000-97b84b2740298afd1c1d	2018-05-18	HMDB team, MONA, MassBank	View Spectrum
Experimental GC-MS	GC-MS Spectrum - Oleamide EI-B (Non-derivatized)	splash10-0ab9-9100000000-b569e50a84dfd9fefa0f	2018-05-25	HMDB team, MONA, MassBank	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oleamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9520000000-b12545c4825e006705c9	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Oleamide 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 - Oleamide 10V, Positive-QTOF	splash10-001i-0090000000-4025e9686e453cf9ff58	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleamide 20V, Positive-QTOF	splash10-02ti-3590000000-ef97bfeb80e7c1b3032d	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleamide 40V, Positive-QTOF	splash10-0006-8910000000-4bbc3e60f25393fa6845	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleamide 10V, Negative-QTOF	splash10-001i-0090000000-07efc552c89b48048777	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleamide 20V, Negative-QTOF	splash10-001l-4090000000-f222c515266d20e324ec	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleamide 40V, Negative-QTOF	splash10-0006-9000000000-e9a8f8874e104368c2af	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleamide 10V, Positive-QTOF	splash10-001i-2190000000-cd304288348f2876b0a1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleamide 20V, Positive-QTOF	splash10-05o0-9560000000-8ef134115ce9c4c4128f	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleamide 40V, Positive-QTOF	splash10-0apl-9000000000-e79597693046f1001f64	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleamide 10V, Negative-QTOF	splash10-001i-0090000000-7ab213c3091ac38bdcb8	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleamide 20V, Negative-QTOF	splash10-0006-9030000000-bf88d7f0f037292d8045	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Oleamide 40V, Negative-QTOF	splash10-0006-9000000000-90726b17dc36e29c5299	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	2010 +/- 530 uM	Adult (>18 years old)	Female	Normal	14608088	details
Blood	Detected and Quantified	2170 +/- 600 uM	Adult (>18 years old)	Male	Normal	14608088	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25105552	details

Associated Disorders and Diseases

Disease References

Colorectal cancer
Ni Y, Xie G, Jia W: Metabonomics of human colorectal cancer: new approaches for early diagnosis and biomarker discovery. J Proteome Res. 2014 Sep 5;13(9):3857-70. doi: 10.1021/pr500443c. Epub 2014 Aug 14. [PubMed:25105552 ]

Associated OMIM IDs

114500 (Colorectal cancer)

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB012436

KNApSAcK ID

Not Available

Chemspider ID

4446508

KEGG Compound ID

C19670

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oleamide

METLIN ID

Not Available

PubChem Compound

5283387

PDB ID

Not Available

ChEBI ID

116314

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

Not Available

Enzymes

Enzyme Details

1. Phospholipase A2, membrane associated

General function:: Involved in phospholipase A2 activity
Specific function:: Thought to participate in the regulation of the phospholipid metabolism in biomembranes including eicosanoid biosynthesis. Catalyzes the calcium-dependent hydrolysis of the 2-acyl groups in 3-sn-phosphoglycerides.
Gene Name:: PLA2G2A
Uniprot ID:: P14555
Molecular weight:: 16082.525

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]

Enzyme Details

2. Amine oxidase [flavin-containing] A

General function:: Involved in oxidoreductase activity
Specific function:: Catalyzes the oxidative deamination of biogenic and xenobiotic amines and has important functions in the metabolism of neuroactive and vasoactive amines in the central nervous system and peripheral tissues. MAOA preferentially oxidizes biogenic amines such as 5-hydroxytryptamine (5-HT), norepinephrine and epinephrine.
Gene Name:: MAOA
Uniprot ID:: P21397
Molecular weight:: 59681.27

Enzyme Details

3. Aromatic-L-amino-acid decarboxylase

General function:: Involved in carboxy-lyase activity
Specific function:: Catalyzes the decarboxylation of L-3,4-dihydroxyphenylalanine (DOPA) to dopamine, L-5-hydroxytryptophan to serotonin and L-tryptophan to tryptamine.
Gene Name:: DDC
Uniprot ID:: P20711
Molecular weight:: 53893.755

Enzyme Details

4. Amiloride-sensitive amine oxidase [copper-containing]

General function:: Involved in copper ion binding
Specific function:: Catalyzes the degradation of compounds such as putrescine, histamine, spermine, and spermidine, substances involved in allergic and immune responses, cell proliferation, tissue differentiation, tumor formation, and possibly apoptosis. Placental DAO is thought to play a role in the regulation of the female reproductive function.
Gene Name:: ABP1
Uniprot ID:: P19801
Molecular weight:: 85377.1

Enzyme Details

5. Fatty-acid amide hydrolase 1

General function:: Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:: Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes polyunsaturated substrate anandamide preferentially as compared to monounsaturated substrates.
Gene Name:: FAAH
Uniprot ID:: O00519
Molecular weight:: 63065.28

Reactions

Oleamide + Water → Oleic acid + Ammonia	details

Enzyme Details

6. Fatty-acid amide hydrolase 2

General function:: Involved in carbon-nitrogen ligase activity, with glutamine as amido-N-donor
Specific function:: Degrades bioactive fatty acid amides like oleamide, the endogenous cannabinoid, anandamide and myristic amide to their corresponding acids, thereby serving to terminate the signaling functions of these molecules. Hydrolyzes monounsaturated substrate anandamide preferentially as compared to polyunsaturated substrates.
Gene Name:: FAAH2
Uniprot ID:: Q6GMR7
Molecular weight:: 58303.115

Reactions

Oleamide + Water → Oleic acid + Ammonia	details

Showing metabocard for Oleamide (HMDB0002117)

MOL for HMDB0002117 (Oleamide)

3D MOL for HMDB0002117 (Oleamide)

3D SDF for HMDB0002117 (Oleamide)

3D-SDF for HMDB0002117 (Oleamide)

PDB for HMDB0002117 (Oleamide)

3D PDB for HMDB0002117 (Oleamide)

SMILES for HMDB0002117 (Oleamide)

INCHI for HMDB0002117 (Oleamide)

Structure for HMDB0002117 (Oleamide)

3D Structure for HMDB0002117 (Oleamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

Reactions

Reactions