MiMeDB: Showing metabocard for Oleoylethanolamide (MMDBc0000774)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:54:39 UTC

Update Date

2024-10-09 15:11:10 UTC

Metabolite ID

MMDBc0000774

Metabolite Identification

Common Name

Oleoylethanolamide

Description

Oleoylethanolamide (OEA or NOE) is an N-acylethanolamine. N-Acylethanolamines (NAEs) constitute a class of lipid compounds naturally present in both animal and plant membranes as constituents of the membrane-bound phospholipid, N-acylphosphatidylethanolamine (NAPE). NAPE is composed of a third fatty acid moiety linked to the amino head group of the commonly occurring membrane phospholipid, phosphatidylethanolamine. NAEs are released from NAPE by phospholipase D-type hydrolases in response to a variety of stimuli. Transient NAE release and accumulation have been attributed to a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. Oleoylethanolamide is an inhibitor of the sphingolipid signalling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). Oleoylethanolamide blocks the effects of TNF and arachidonic acid on intracellular Ca concentration (PMID: 12692337 , 12056855 , 12560208 , 11997249 ). Oleoylethanolamide is related to the endocannabinoid anandamide. Endocannabinoids signal through cannabinoid receptors (also stimulated by the active ingredient of cannabis) but although related in structure, synthesis, and degradation to anandamide, OEA cannot be considered an endocannabinoid as it does not activate the cannabinoid receptors. Most of the reported responses to OEA can be attributed to the activation of peroxisome proliferator-activated receptor-alpha (PPAR-alpha). Administration of OEA inhibits body weight gain in rats. In adipocytes and hepatocytes, OEA inhibits mitogenic and metabolic signalling by the insulin receptor and produces glucose intolerance. It also inhibits gastric emptying, which might act together with the sensory neuronal signals to achieve satiety. OEA is permanently elevated in diabetic obese patients. OEA also reduces visceral and inflammatory responses through a PPAR-alpha-activation independent mechanism (PMID: 17449181 ). OEA is an antagonist of TRVP1 (the transient receptor potential vanilloid type 1 receptor). Overall, OEA has beneficial effects on health by inducing food intake control, lipid beta-oxidation, body weight loss and analgesic effects (PMID: 18704536 ).

Structure

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

HMDB0002088
     RDKit          3D
Oleoylethanolamide
 62 61  0  0  0  0  0  0  0  0999 V2000
   -7.4548   -1.2059    2.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0827    0.1334    1.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1321    0.9303    2.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149    0.4363    2.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7931    0.0520    1.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1296   -1.1031    0.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2519   -1.5034   -0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8379   -1.8361   -0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9948   -0.7266    0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565   -0.3492   -0.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4588   -0.9941   -1.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4567   -0.0293   -2.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4147    1.0992   -2.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8195    0.5762   -2.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7995    1.7335   -2.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5069    2.4940   -1.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6451    1.6254    0.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750    1.1726    0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9564    1.6421   -0.5709 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3574    0.2102    1.1866 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6098   -0.3999    1.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1322   -1.2062    0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3303   -0.4214   -0.7486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5875   -1.7396    2.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2657   -1.1523    2.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8517   -1.8191    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9776    0.1571    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0939    0.7232    1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0307    1.9341    1.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6674    1.1960    3.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8743   -0.4238    3.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3439    1.2468    3.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9242   -0.3468    2.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1661   -1.0505    0.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2177   -1.9952    1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -3.6897   -2.4218   -0.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8777   -2.5536    0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3982   -2.5217   -0.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6280    0.5189   -0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1159   -1.8796   -2.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
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    2.9750   -0.1541   -1.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1175    0.0816   -3.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8061    1.2745   -2.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6441    2.3887   -3.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2999    3.3250   -1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5039    2.9797   -1.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3675    2.2105    0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9606    0.7779    0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5335   -0.1153    1.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3547    0.4221    1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4981   -1.0656    2.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0757   -1.7192    0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3456   -1.9494    0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4292   -0.9719   -1.5698 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
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 13 14  1  0
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  1 24  1  0
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M  END


  Mrv1652311251922492D          

 23 22  0  0  0  0            999 V2000
10004.688010007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10005.403410007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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10008.976310007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10009.801410007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10010.516010007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.230410007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10011.945010007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10012.659710007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10013.374310007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.088710007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10014.805310007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10015.520110007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.974810007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10003.259410007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10002.546110007.3668    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
10001.830810007.7791    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10001.113410007.3668    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
10000.400110007.7791    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
10003.259410008.6035    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1 17  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
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 18 23  2  0  0  0  0
 19 20  1  0  0  0  0
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 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000774

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-

> <INCHI_KEY>
BOWVQLFMWHZBEF-KTKRTIGZSA-N

> <FORMULA>
C20H39NO2

> <MOLECULAR_WEIGHT>
325.5292

> <EXACT_MASS>
325.298079497

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
62

> <JCHEM_AVERAGE_POLARIZABILITY>
42.772357373818814

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
6.74

> <JCHEM_LOGP>
5.510429891

> <ALOGPS_LOGS>
-6.13

> <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>
-1.3086129187290512

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
100.41339999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.44e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
oleoylethanolamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002088
     RDKit          3D
Oleoylethanolamide
 62 61  0  0  0  0  0  0  0  0999 V2000
   -7.4548   -1.2059    2.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0827    0.1334    1.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1321    0.9303    2.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149    0.4363    2.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7931    0.0520    1.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1296   -1.1031    0.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2519   -1.5034   -0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8379   -1.8361   -0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9948   -0.7266    0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565   -0.3492   -0.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4588   -0.9941   -1.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4567   -0.0293   -2.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4147    1.0992   -2.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8195    0.5762   -2.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7995    1.7335   -2.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5069    2.4940   -1.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6451    1.6254    0.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750    1.1726    0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9564    1.6421   -0.5709 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3574    0.2102    1.1866 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6098   -0.3999    1.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1322   -1.2062    0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3303   -0.4214   -0.7486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5875   -1.7396    2.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2657   -1.1523    2.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8517   -1.8191    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9776    0.1571    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0939    0.7232    1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0307    1.9341    1.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6674    1.1960    3.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8743   -0.4238    3.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
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    0.6280    0.5189   -0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -0.1159   -1.8796   -2.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5749    0.3140   -3.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
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    1.3384    1.7864   -3.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1381    1.7030   -1.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -0.1541   -1.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1175    0.0816   -3.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8061    1.2745   -2.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6441    2.3887   -3.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2999    3.3250   -1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5039    2.9797   -1.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3675    2.2105    0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9606    0.7779    0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5335   -0.1153    1.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3547    0.4221    1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4981   -1.0656    2.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0757   -1.7192    0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3456   -1.9494    0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4292   -0.9719   -1.5698 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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  3 30  1  0
  4 31  1  0
  4 32  1  0
  5 33  1  0
  5 34  1  0
  6 35  1  0
  6 36  1  0
  7 37  1  0
  7 38  1  0
  8 39  1  0
  8 40  1  0
  9 41  1  0
 10 42  1  0
 11 43  1  0
 11 44  1  0
 12 45  1  0
 12 46  1  0
 13 47  1  0
 13 48  1  0
 14 49  1  0
 14 50  1  0
 15 51  1  0
 15 52  1  0
 16 53  1  0
 16 54  1  0
 17 55  1  0
 17 56  1  0
 20 57  1  0
 21 58  1  0
 21 59  1  0
 22 60  1  0
 22 61  1  0
 23 62  1  0
M  END

HEADER    PROTEIN                                 25-NOV-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   25-NOV-19         0                                  
HETATM    1  C   UNK     0    8675.4188681.188   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8676.7538680.418   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8678.0888681.188   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8679.4208680.418   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8680.7558681.188   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8682.0888680.418   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8683.4228681.188   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8684.9638681.188   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8686.2968680.418   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8687.6308681.188   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8688.9648680.418   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8690.2988681.188   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8691.6328680.418   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8692.9668681.188   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8694.3038680.418   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8695.6378681.188   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8674.0868680.418   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8672.7518681.188   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0    8671.4198680.418   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0    8670.0848681.188   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8668.7458680.418   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0    8667.4148681.188   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0    8672.7518682.726   0.000  0.00  0.00           O+0
CONECT    1    2   17                                                       
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                                                            
CONECT   17    1   18                                                       
CONECT   18   17   19   23                                                  
CONECT   19   18   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   18                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0002088
HETATM    1  C1  UNL     1      -7.455  -1.206   2.026  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.083   0.133   1.434  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.132   0.930   2.225  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.815   0.436   2.598  1.00  0.00           C  
HETATM    5  C5  UNL     1      -3.793   0.052   1.590  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.130  -1.103   0.737  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.252  -1.503  -0.378  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.838  -1.836  -0.106  1.00  0.00           C  
HETATM    9  C9  UNL     1      -0.995  -0.727   0.285  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.056  -0.349  -0.444  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.459  -0.994  -1.683  1.00  0.00           C  
HETATM   12  C12 UNL     1       0.457  -0.029  -2.860  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.415   1.099  -2.640  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.820   0.576  -2.532  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.800   1.733  -2.374  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.507   2.494  -1.125  1.00  0.00           C  
HETATM   17  C17 UNL     1       3.645   1.625   0.085  1.00  0.00           C  
HETATM   18  C18 UNL     1       5.075   1.173   0.194  1.00  0.00           C  
HETATM   19  O1  UNL     1       5.956   1.642  -0.571  1.00  0.00           O  
HETATM   20  N1  UNL     1       5.357   0.210   1.187  1.00  0.00           N  
HETATM   21  C19 UNL     1       6.610  -0.400   1.505  1.00  0.00           C  
HETATM   22  C20 UNL     1       7.132  -1.206   0.354  1.00  0.00           C  
HETATM   23  O2  UNL     1       7.330  -0.421  -0.749  1.00  0.00           O  
HETATM   24  H1  UNL     1      -6.588  -1.740   2.467  1.00  0.00           H  
HETATM   25  H2  UNL     1      -8.266  -1.152   2.779  1.00  0.00           H  
HETATM   26  H3  UNL     1      -7.852  -1.819   1.177  1.00  0.00           H  
HETATM   27  H4  UNL     1      -6.978   0.157   0.345  1.00  0.00           H  
HETATM   28  H5  UNL     1      -8.094   0.723   1.551  1.00  0.00           H  
HETATM   29  H6  UNL     1      -6.031   1.934   1.712  1.00  0.00           H  
HETATM   30  H7  UNL     1      -6.667   1.196   3.195  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.874  -0.424   3.331  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.344   1.247   3.261  1.00  0.00           H  
HETATM   33  H10 UNL     1      -2.924  -0.347   2.265  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.330   0.904   1.064  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.166  -1.050   0.302  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.218  -1.995   1.481  1.00  0.00           H  
HETATM   37  H14 UNL     1      -3.295  -0.730  -1.227  1.00  0.00           H  
HETATM   38  H15 UNL     1      -3.690  -2.422  -0.922  1.00  0.00           H  
HETATM   39  H16 UNL     1      -1.878  -2.554   0.807  1.00  0.00           H  
HETATM   40  H17 UNL     1      -1.398  -2.522  -0.867  1.00  0.00           H  
HETATM   41  H18 UNL     1      -1.182  -0.154   1.217  1.00  0.00           H  
HETATM   42  H19 UNL     1       0.628   0.519  -0.047  1.00  0.00           H  
HETATM   43  H20 UNL     1       1.502  -1.410  -1.523  1.00  0.00           H  
HETATM   44  H21 UNL     1      -0.116  -1.880  -2.003  1.00  0.00           H  
HETATM   45  H22 UNL     1      -0.575   0.314  -3.036  1.00  0.00           H  
HETATM   46  H23 UNL     1       0.818  -0.575  -3.780  1.00  0.00           H  
HETATM   47  H24 UNL     1       1.338   1.786  -3.534  1.00  0.00           H  
HETATM   48  H25 UNL     1       1.138   1.703  -1.741  1.00  0.00           H  
HETATM   49  H26 UNL     1       2.975  -0.154  -1.735  1.00  0.00           H  
HETATM   50  H27 UNL     1       3.117   0.082  -3.497  1.00  0.00           H  
HETATM   51  H28 UNL     1       4.806   1.275  -2.424  1.00  0.00           H  
HETATM   52  H29 UNL     1       3.644   2.389  -3.291  1.00  0.00           H  
HETATM   53  H30 UNL     1       4.300   3.325  -1.091  1.00  0.00           H  
HETATM   54  H31 UNL     1       2.504   2.980  -1.162  1.00  0.00           H  
HETATM   55  H32 UNL     1       3.368   2.211   0.995  1.00  0.00           H  
HETATM   56  H33 UNL     1       2.961   0.778   0.025  1.00  0.00           H  
HETATM   57  H34 UNL     1       4.534  -0.115   1.788  1.00  0.00           H  
HETATM   58  H35 UNL     1       7.355   0.422   1.765  1.00  0.00           H  
HETATM   59  H36 UNL     1       6.498  -1.066   2.406  1.00  0.00           H  
HETATM   60  H37 UNL     1       8.076  -1.719   0.669  1.00  0.00           H  
HETATM   61  H38 UNL     1       6.346  -1.949   0.088  1.00  0.00           H  
HETATM   62  H39 UNL     1       7.429  -0.972  -1.570  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4   29   30
CONECT    4    5   31   32
CONECT    5    6   33   34
CONECT    6    7   35   36
CONECT    7    8   37   38
CONECT    8    9   39   40
CONECT    9   10   10   41
CONECT   10   11   42
CONECT   11   12   43   44
CONECT   12   13   45   46
CONECT   13   14   47   48
CONECT   14   15   49   50
CONECT   15   16   51   52
CONECT   16   17   53   54
CONECT   17   18   55   56
CONECT   18   19   19   20
CONECT   20   21   57
CONECT   21   22   58   59
CONECT   22   23   60   61
CONECT   23   62
END

HMDB0002088
     RDKit          3D
Oleoylethanolamide
 62 61  0  0  0  0  0  0  0  0999 V2000
   -7.4548   -1.2059    2.0258 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0827    0.1334    1.4344 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1321    0.9303    2.2254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8149    0.4363    2.5983 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7931    0.0520    1.5903 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.1296   -1.1031    0.7369 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2519   -1.5034   -0.3776 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8379   -1.8361   -0.1064 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9948   -0.7266    0.2855 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.0565   -0.3492   -0.4441 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4588   -0.9941   -1.6825 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4567   -0.0293   -2.8596 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4147    1.0992   -2.6399 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8195    0.5762   -2.5317 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7995    1.7335   -2.3741 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5069    2.4940   -1.1251 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6451    1.6254    0.0852 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0750    1.1726    0.1942 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9564    1.6421   -0.5709 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.3574    0.2102    1.1866 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6098   -0.3999    1.5051 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1322   -1.2062    0.3535 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3303   -0.4214   -0.7486 O   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5875   -1.7396    2.4671 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2657   -1.1523    2.7795 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.8517   -1.8191    1.1766 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9776    0.1571    0.3445 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.0939    0.7232    1.5513 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0307    1.9341    1.7115 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6674    1.1960    3.1952 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8743   -0.4238    3.3306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3439    1.2468    3.2606 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.9242   -0.3468    2.2650 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3299    0.9045    1.0645 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1661   -1.0505    0.3022 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2177   -1.9952    1.4806 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2948   -0.7297   -1.2267 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6897   -2.4218   -0.9220 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8777   -2.5536    0.8075 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3982   -2.5217   -0.8672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1816   -0.1542    1.2173 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6280    0.5189   -0.0465 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5021   -1.4102   -1.5230 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1159   -1.8796   -2.0026 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5749    0.3140   -3.0362 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.8183   -0.5747   -3.7805 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3384    1.7864   -3.5338 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1381    1.7030   -1.7407 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9750   -0.1541   -1.7345 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1175    0.0816   -3.4966 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8061    1.2745   -2.4244 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.6441    2.3887   -3.2915 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2999    3.3250   -1.0910 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5039    2.9797   -1.1618 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3675    2.2105    0.9950 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9606    0.7779    0.0245 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5335   -0.1153    1.7876 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.3547    0.4221    1.7650 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4981   -1.0656    2.4058 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0757   -1.7192    0.6685 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.3456   -1.9494    0.0878 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4292   -0.9719   -1.5698 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  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
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M  END

Synonyms

Value	Source
N-(2-Hydroxyethyl)-9-octadecenamide	ChEBI
N-(2-Hydroxyethyl)oleamide	ChEBI
N-(9Z-Octadecenoyl) ethanolamine	ChEBI
N-(9Z-Octadecenoyl)-ethanolamine	ChEBI
N-(cis-9-Octadecenoyl) ethanolamine	ChEBI
N-(Hydroxyethyl)oleamide	ChEBI
N-Oleoyl ethanolamine	ChEBI
N-Oleoylethanolamine	ChEBI
OEA	ChEBI
Oleamide mea	ChEBI
Oleoyl 1-ethanolamide	ChEBI
Oleoyl monoethanolamide	ChEBI
N-Oleoyl ethanolamine, oleoyl monoethanolamide, oleoylethanolamide	HMDB
N-Oleoyl-2-aminoethanol	HMDB
NOE	HMDB
Oleic acid ethanolamide	HMDB
Oleic acid monoethanolamide	HMDB
N-OEA	HMDB
(9Z)-N-(2-Hydroxyethyl)-9-octadecenamide	HMDB
N-(2-Hydroxyethyl)-9-Z-octadecenamide	HMDB
N-Oleoylethanolamide	HMDB
Oleoyl ethanolamide	HMDB
Oleoylethanolamine	HMDB
Oleoylethanolamide	ChEBI
AEA(18:1)	HMDB
Acylethanolamine 18:1	HMDB

Molecular Formula

C₂₀H₃₉NO₂

Average Mass

325.5292

Monoisotopic Mass

325.298079497

IUPAC Name

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

Traditional Name

oleoylethanolamide

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h9-10,22H,2-8,11-19H2,1H3,(H,21,23)/b10-9-

InChI Key

BOWVQLFMWHZBEF-KTKRTIGZSA-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:71466 )
N-(long-chain-acyl)ethanolamine (CHEBI:71466 )
endocannabinoid (CHEBI:71466 )
N-acyl ethanolamines (endocannabinoids) (LMFA08040015 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00024 g/L	ALOGPS
logP	6.74	ALOGPS
logP	5.51	ChemAxon
logS	-6.1	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	17	ChemAxon
Refractivity	100.41 m³·mol⁻¹	ChemAxon
Polarizability	42.77 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Not Available

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces
Placenta
Urine

Tissue Locations

Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0195881	Neutral ceramidase	Enzyme	Q9NR71	Homo sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Metabolic Reactions

Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria/Eubacteria	Verrucomicrobia	1	Human feces; Human stool; Human ; Human urine	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Firmicutes	8	Human stool; Human feces; Human mucosa; Human ; Human saliva; Human urine; Human sputum	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference
Cosmetics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Domestics	U.S. Environmental Protection Agency	CompTox
Cosmetics	U.S. Environmental Protection Agency	CompTox

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Units	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified							HMDB
Human Blood	Detected and Quantified	0.0036	0.00068	uM	Adult (>18 years old)	Both	Normal	HMDB	17196922
Human Blood	Detected and Quantified	46.8	34	uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Placenta	Detected but not Quantified				Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	29808030
Human Urine	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057
Human Blood	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	32966057

External Links

HMDB ID

HMDB0002088

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB022839

KNApSAcK ID

Not Available

Chemspider ID

4446574

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Oleoylethanolamide

METLIN ID

Not Available

PubChem Compound

5283454

PDB ID

Not Available

ChEBI ID

71466

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Amadou A, Nawrocki A, Best-Belpomme M, Pavoine C, Pecker F: Arachidonic acid mediates dual effect of TNF-alpha on Ca2+ transients and contraction of adult rat cardiomyocytes. Am J Physiol Cell Physiol. 2002 Jun;282(6):C1339-47. doi: 10.1152/ajpcell.00471.2001. [PubMed:11997249 ]
Lecour S, Smith RM, Woodward B, Opie LH, Rochette L, Sack MN: Identification of a novel role for sphingolipid signaling in TNF alpha and ischemic preconditioning mediated cardioprotection. J Mol Cell Cardiol. 2002 May;34(5):509-18. doi: 10.1006/jmcc.2002.1533. [PubMed:12056855 ]
Hofmann U, Domeier E, Frantz S, Laser M, Weckler B, Kuhlencordt P, Heuer S, Keweloh B, Ertl G, Bonz AW: Increased myocardial oxygen consumption by TNF-alpha is mediated by a sphingosine signaling pathway. Am J Physiol Heart Circ Physiol. 2003 Jun;284(6):H2100-5. doi: 10.1152/ajpheart.00888.2002. Epub 2003 Jan 30. [PubMed:12560208 ]
Tripathy S, Kleppinger-Sparace K, Dixon RA, Chapman KD: N-acylethanolamine signaling in tobacco is mediated by a membrane-associated, high-affinity binding protein. Plant Physiol. 2003 Apr;131(4):1781-91. doi: 10.1104/pp.102.014936. [PubMed:12692337 ]
Suardiaz M, Estivill-Torrus G, Goicoechea C, Bilbao A, Rodriguez de Fonseca F: Analgesic properties of oleoylethanolamide (OEA) in visceral and inflammatory pain. Pain. 2007 Dec 15;133(1-3):99-110. doi: 10.1016/j.pain.2007.03.008. Epub 2007 Apr 20. [PubMed:17449181 ]
Thabuis C, Tissot-Favre D, Bezelgues JB, Martin JC, Cruz-Hernandez C, Dionisi F, Destaillats F: Biological functions and metabolism of oleoylethanolamide. Lipids. 2008 Oct;43(10):887-94. doi: 10.1007/s11745-008-3217-y. Epub 2008 Aug 13. [PubMed:18704536 ]
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 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Oleoylethanolamide (MMDBc0000774)

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