MiMeDB: Showing metabocard for Linoleoyl ethanolamide (MMDBc0000839)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-11 16:57:58 UTC

Update Date

2024-10-17 07:46:14 UTC

Metabolite ID

MMDBc0000839

Metabolite Identification

Common Name

Linoleoyl ethanolamide

Description

Linoleoyl ethanolamide, also known as linoleamide mea or anandamide (18:2, N-6), 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, linoleoyl ethanolamide is considered to be a fatty amide. Based on a literature review very few articles have been published on Linoleoyl ethanolamide.

Structure

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

HMDB0012252
     RDKit          3D
Linoleoyl ethanolamide
 60 59  0  0  0  0  0  0  0  0999 V2000
   -6.5136    3.1603   -3.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0271    1.9948   -2.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5519    2.1486   -1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0684    2.1843   -1.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858    0.9302   -1.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7896   -0.2721   -0.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0626   -1.0974   -0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6423   -1.1010    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8162   -0.0038   -0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -0.0999   -1.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587   -1.3462   -1.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758   -1.6969   -1.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2530   -1.8602    0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279   -2.2103    0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0212   -2.3966    1.7006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4815   -2.7367    1.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4174   -1.6981    1.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3075   -0.3751    1.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5096   -0.1566    2.9225 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1247    0.6742    1.5163 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0575    1.9754    2.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4181    1.9166    3.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3310    3.2251    4.0983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7168    2.7682   -4.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0567    3.9509   -2.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3378    3.5623   -4.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1603    2.0166   -2.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7653    1.0082   -2.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9076    1.3007   -0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0312    3.0602   -0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6375    3.0768   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8006    2.3185   -0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8017    0.7837   -2.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3435    1.1315   -1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8885   -0.5062   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6715   -1.9606    0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4920   -1.1750    1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2236   -2.1180   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0150    1.0156    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2704    0.8342   -1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3166   -1.1424   -2.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9813   -2.2207   -1.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7573   -0.8736   -1.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -2.6649   -1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6539   -2.7431    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9682   -0.9433    0.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8801   -3.1941   -0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3303   -1.4040   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7630   -1.5282    2.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339   -3.2670    2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7394   -3.6917    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7181   -2.8765    2.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328   -1.5402    0.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4485   -2.0692    1.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7861    0.5134    0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0265    2.4134    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7124    2.7004    1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4399    1.5104    3.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7244    1.3206    4.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6438    3.1849    5.0327 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  2  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
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 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
 16 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
M  END


  Mrv1652301171918382D          

 23 22  0  0  0  0            999 V2000
 9981.3167 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.0302 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9982.7458 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9983.4593 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.1749 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9984.8899 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9985.6046 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9986.4301 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.1448 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9987.8596 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9988.6852 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9989.3999 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.1147 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9990.8294 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9991.5463 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9992.2612 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9980.6011 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.8855 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9979.1720 9984.0396    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
 9978.4564 9984.4513    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9977.7388 9984.0396    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
 9977.0253 9984.4513    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
 9979.8855 9985.2768    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
  6  7  1  0  0  0  0
  7  8  2  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  0  0  0  0
 18 23  2  0  0  0  0
 19 20  1  0  0  0  0
 20 21  1  0  0  0  0
 21 22  1  0  0  0  0
M  END
> <DATABASE_ID>
MMDBc0000839

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h6-7,9-10,22H,2-5,8,11-19H2,1H3,(H,21,23)/b7-6-,10-9-

> <INCHI_KEY>
KQXDGUVSAAQARU-HZJYTTRNSA-N

> <FORMULA>
C20H37NO2

> <MOLECULAR_WEIGHT>
323.5133

> <EXACT_MASS>
323.282429433

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
60

> <JCHEM_AVERAGE_POLARIZABILITY>
41.410886059353125

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z,12Z)-N-(2-hydroxyethyl)octadeca-9,12-dienamide

> <ALOGPS_LOGP>
6.26

> <JCHEM_LOGP>
5.148508234333334

> <ALOGPS_LOGS>
-5.89

> <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>
101.52999999999997

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
4.20e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
linoleamide mea

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0012252
     RDKit          3D
Linoleoyl ethanolamide
 60 59  0  0  0  0  0  0  0  0999 V2000
   -6.5136    3.1603   -3.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0271    1.9948   -2.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5519    2.1486   -1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0684    2.1843   -1.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858    0.9302   -1.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7896   -0.2721   -0.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0626   -1.0974   -0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6423   -1.1010    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8162   -0.0038   -0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -0.0999   -1.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587   -1.3462   -1.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758   -1.6969   -1.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2530   -1.8602    0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279   -2.2103    0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0212   -2.3966    1.7006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4815   -2.7367    1.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4174   -1.6981    1.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3075   -0.3751    1.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5096   -0.1566    2.9225 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1247    0.6742    1.5163 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0575    1.9754    2.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4181    1.9166    3.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3310    3.2251    4.0983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7168    2.7682   -4.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0567    3.9509   -2.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3378    3.5623   -4.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1603    2.0166   -2.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7653    1.0082   -2.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9076    1.3007   -0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0312    3.0602   -0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6375    3.0768   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8006    2.3185   -0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8017    0.7837   -2.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3435    1.1315   -1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8885   -0.5062   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6715   -1.9606    0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4920   -1.1750    1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2236   -2.1180   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0150    1.0156    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2704    0.8342   -1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3166   -1.1424   -2.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9813   -2.2207   -1.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7573   -0.8736   -1.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -2.6649   -1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6539   -2.7431    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9682   -0.9433    0.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8801   -3.1941   -0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3303   -1.4040   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7630   -1.5282    2.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339   -3.2670    2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7394   -3.6917    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7181   -2.8765    2.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328   -1.5402    0.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4485   -2.0692    1.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7861    0.5134    0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0265    2.4134    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7124    2.7004    1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4399    1.5104    3.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7244    1.3206    4.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6438    3.1849    5.0327 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  2  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
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 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
 16 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
M  END

HEADER    PROTEIN                                 17-JAN-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   17-JAN-19         0                                  
HETATM    1  C   UNK     0    8631.7918637.642   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0    8633.1238636.874   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0    8634.4598637.642   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0    8635.7918636.874   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0    8637.1268637.642   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0    8638.4618636.874   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0    8639.7958637.642   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0    8641.3368637.642   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0    8642.6708636.874   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0    8644.0058637.642   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0    8645.5468637.642   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0    8646.8808636.874   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0    8648.2148637.642   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0    8649.5488636.874   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0    8650.8868637.642   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0    8652.2218636.874   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0    8630.4558636.874   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0    8629.1208637.642   0.000  0.00  0.00           C+0
HETATM   19  N   UNK     0    8627.7888636.874   0.000  0.00  0.00           N+0
HETATM   20  C   UNK     0    8626.4528637.642   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0    8625.1128636.874   0.000  0.00  0.00           C+0
HETATM   22  O   UNK     0    8623.7818637.642   0.000  0.00  0.00           O+0
HETATM   23  O   UNK     0    8629.1208639.183   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    HMDB0012252
HETATM    1  C1  UNL     1      -6.514   3.160  -3.408  1.00  0.00           C  
HETATM    2  C2  UNL     1      -7.027   1.995  -2.593  1.00  0.00           C  
HETATM    3  C3  UNL     1      -6.552   2.149  -1.167  1.00  0.00           C  
HETATM    4  C4  UNL     1      -5.068   2.184  -1.084  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.386   0.930  -1.625  1.00  0.00           C  
HETATM    6  C6  UNL     1      -4.790  -0.272  -0.926  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.063  -1.097  -0.235  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.642  -1.101   0.072  1.00  0.00           C  
HETATM    9  C9  UNL     1      -1.816  -0.004  -0.377  1.00  0.00           C  
HETATM   10  C10 UNL     1      -0.804  -0.100  -1.219  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.359  -1.346  -1.835  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.076  -1.697  -1.485  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.253  -1.860   0.011  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.728  -2.210   0.227  1.00  0.00           C  
HETATM   15  C15 UNL     1       3.021  -2.397   1.701  1.00  0.00           C  
HETATM   16  C16 UNL     1       4.482  -2.737   1.845  1.00  0.00           C  
HETATM   17  C17 UNL     1       5.417  -1.698   1.318  1.00  0.00           C  
HETATM   18  C18 UNL     1       5.308  -0.375   1.973  1.00  0.00           C  
HETATM   19  O1  UNL     1       4.510  -0.157   2.922  1.00  0.00           O  
HETATM   20  N1  UNL     1       6.125   0.674   1.516  1.00  0.00           N  
HETATM   21  C19 UNL     1       6.057   1.975   2.118  1.00  0.00           C  
HETATM   22  C20 UNL     1       6.418   1.917   3.579  1.00  0.00           C  
HETATM   23  O2  UNL     1       6.331   3.225   4.098  1.00  0.00           O  
HETATM   24  H1  UNL     1      -5.717   2.768  -4.099  1.00  0.00           H  
HETATM   25  H2  UNL     1      -6.057   3.951  -2.780  1.00  0.00           H  
HETATM   26  H3  UNL     1      -7.338   3.562  -4.029  1.00  0.00           H  
HETATM   27  H4  UNL     1      -8.160   2.017  -2.617  1.00  0.00           H  
HETATM   28  H5  UNL     1      -6.765   1.008  -2.998  1.00  0.00           H  
HETATM   29  H6  UNL     1      -6.908   1.301  -0.541  1.00  0.00           H  
HETATM   30  H7  UNL     1      -7.031   3.060  -0.733  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.637   3.077  -1.594  1.00  0.00           H  
HETATM   32  H9  UNL     1      -4.801   2.319  -0.004  1.00  0.00           H  
HETATM   33  H10 UNL     1      -4.802   0.784  -2.704  1.00  0.00           H  
HETATM   34  H11 UNL     1      -3.343   1.131  -1.755  1.00  0.00           H  
HETATM   35  H12 UNL     1      -5.888  -0.506  -1.002  1.00  0.00           H  
HETATM   36  H13 UNL     1      -4.671  -1.961   0.195  1.00  0.00           H  
HETATM   37  H14 UNL     1      -2.492  -1.175   1.221  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.224  -2.118  -0.228  1.00  0.00           H  
HETATM   39  H16 UNL     1      -2.015   1.016   0.041  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.270   0.834  -1.462  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.317  -1.142  -2.958  1.00  0.00           H  
HETATM   42  H19 UNL     1      -0.981  -2.221  -1.738  1.00  0.00           H  
HETATM   43  H20 UNL     1       1.757  -0.874  -1.799  1.00  0.00           H  
HETATM   44  H21 UNL     1       1.354  -2.665  -1.948  1.00  0.00           H  
HETATM   45  H22 UNL     1       0.654  -2.743   0.366  1.00  0.00           H  
HETATM   46  H23 UNL     1       0.968  -0.943   0.567  1.00  0.00           H  
HETATM   47  H24 UNL     1       2.880  -3.194  -0.262  1.00  0.00           H  
HETATM   48  H25 UNL     1       3.330  -1.404  -0.188  1.00  0.00           H  
HETATM   49  H26 UNL     1       2.763  -1.528   2.324  1.00  0.00           H  
HETATM   50  H27 UNL     1       2.434  -3.267   2.083  1.00  0.00           H  
HETATM   51  H28 UNL     1       4.739  -3.692   1.333  1.00  0.00           H  
HETATM   52  H29 UNL     1       4.718  -2.876   2.929  1.00  0.00           H  
HETATM   53  H30 UNL     1       5.333  -1.540   0.229  1.00  0.00           H  
HETATM   54  H31 UNL     1       6.449  -2.069   1.496  1.00  0.00           H  
HETATM   55  H32 UNL     1       6.786   0.513   0.736  1.00  0.00           H  
HETATM   56  H33 UNL     1       5.026   2.413   1.994  1.00  0.00           H  
HETATM   57  H34 UNL     1       6.712   2.700   1.572  1.00  0.00           H  
HETATM   58  H35 UNL     1       7.440   1.510   3.697  1.00  0.00           H  
HETATM   59  H36 UNL     1       5.724   1.321   4.192  1.00  0.00           H  
HETATM   60  H37 UNL     1       6.644   3.185   5.033  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    7   35
CONECT    7    8   36
CONECT    8    9   37   38
CONECT    9   10   10   39
CONECT   10   11   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   51   52
CONECT   17   18   53   54
CONECT   18   19   19   20
CONECT   20   21   55
CONECT   21   22   56   57
CONECT   22   23   58   59
CONECT   23   60
END

HMDB0012252
     RDKit          3D
Linoleoyl ethanolamide
 60 59  0  0  0  0  0  0  0  0999 V2000
   -6.5136    3.1603   -3.4082 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0271    1.9948   -2.5927 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5519    2.1486   -1.1666 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0684    2.1843   -1.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3858    0.9302   -1.6252 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7896   -0.2721   -0.9256 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0626   -1.0974   -0.2352 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6423   -1.1010    0.0718 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8162   -0.0038   -0.3770 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8038   -0.0999   -1.2189 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3587   -1.3462   -1.8345 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0758   -1.6969   -1.4851 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2530   -1.8602    0.0113 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7279   -2.2103    0.2273 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0212   -2.3966    1.7006 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4815   -2.7367    1.8452 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4174   -1.6981    1.3183 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3075   -0.3751    1.9731 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5096   -0.1566    2.9225 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.1247    0.6742    1.5163 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.0575    1.9754    2.1183 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4181    1.9166    3.5787 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3310    3.2251    4.0983 O   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7168    2.7682   -4.0991 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0567    3.9509   -2.7796 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3378    3.5623   -4.0286 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1603    2.0166   -2.6165 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7653    1.0082   -2.9981 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9076    1.3007   -0.5410 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0312    3.0602   -0.7335 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6375    3.0768   -1.5944 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8006    2.3185   -0.0036 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8017    0.7837   -2.7038 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3435    1.1315   -1.7547 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8885   -0.5062   -1.0017 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6715   -1.9606    0.1948 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4920   -1.1750    1.2212 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2236   -2.1180   -0.2276 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0150    1.0156    0.0414 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2704    0.8342   -1.4619 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3166   -1.1424   -2.9575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9813   -2.2207   -1.7377 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.7573   -0.8736   -1.7993 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3542   -2.6649   -1.9479 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6539   -2.7431    0.3658 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9682   -0.9433    0.5672 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8801   -3.1941   -0.2617 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.3303   -1.4040   -0.1878 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7630   -1.5282    2.3240 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4339   -3.2670    2.0830 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7394   -3.6917    1.3329 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.7181   -2.8765    2.9290 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3328   -1.5402    0.2289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4485   -2.0692    1.4964 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7861    0.5134    0.7358 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.0265    2.4134    1.9941 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7124    2.7004    1.5718 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4399    1.5104    3.6966 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.7244    1.3206    4.1921 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6438    3.1849    5.0327 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  2  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
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 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
 16 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 20 55  1  0
 21 56  1  0
 21 57  1  0
 22 58  1  0
 22 59  1  0
 23 60  1  0
M  END

Synonyms

Value	Source
(9Z,12Z)-N-(2-Hydroxyethyl)octadeca-9,12-dien-1-amide	ChEBI
Anandamide (18:2, N-6)	ChEBI
Linoleamide mea	ChEBI
Linoleic ethanolamide	ChEBI
Linoleoyl monoethanolamide	ChEBI
Monoethanolamine linoleic acid amide	ChEBI
N-(2-Hydroxyethyl)-9,12-octadecadienamide	ChEBI
N-(2-Hydroxyethyl)linoleamide	ChEBI
N-(9Z,12Z-Octadecadienoyl)-ethanolamine	ChEBI
N-cis-9-cis-12-Octadecadienoylethanolamine	ChEBI
Monoethanolamine linoleate amide	Generator
LEA	HMDB
N-(2-Hydroxyethyl)-linoleamide	HMDB
Linoleoylethanolamide	HMDB
Linoleoyl ethanolamide	MeSH

Molecular Formula

C₂₀H₃₇NO₂

Average Mass

323.5133

Monoisotopic Mass

323.282429433

IUPAC Name

(9Z,12Z)-N-(2-hydroxyethyl)octadeca-9,12-dienamide

Traditional Name

linoleamide mea

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h6-7,9-10,22H,2-5,8,11-19H2,1H3,(H,21,23)/b7-6-,10-9-

InChI Key

KQXDGUVSAAQARU-HZJYTTRNSA-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-(polyunsaturated fatty acyl)ethanolamine (CHEBI:64032 )
N-(long-chain-acyl)ethanolamine (CHEBI:64032 )
N-acyl ethanolamines (endocannabinoids) (LMFA08040004 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	0.00042 g/L	ALOGPS
logP	6.26	ALOGPS
logP	5.15	ChemAxon
logS	-5.9	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	16	ChemAxon
Refractivity	101.53 m³·mol⁻¹	ChemAxon
Polarizability	41.41 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
Urine

Tissue Locations

Not Available

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species

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	9	Human feces; Human stool; Human ; Human urine; Human sputum; Human saliva; Human subgingival plaque; Human vaginal fluid; Human supragingival plaque; Human mucosa	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria/Eubacteria	Proteobacteria	2	Human ; Human feces; Human feces; pleural fluid plaque; bal; Human stool; Human mucosa; Human supragingival plaque; Human saliva; Human subgingival plaque	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces; Human	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
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	13.7	6.5	uM	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Feces	Detected but not Quantified				Adult (>18 years old)	Both	Normal	HMDB	27543620
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

HMDB0012252

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB028893

KNApSAcK ID

Not Available

Chemspider ID

4446566

KEGG Compound ID

Not Available

BioCyc ID

CPD6666-4

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283446

PDB ID

Not Available

ChEBI ID

64032

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

General References

Noronha A, Modamio J, Jarosz Y, Guerard E, Sompairac N, Preciat G, Danielsdottir AD, Krecke M, Merten D, Haraldsdottir HS, Heinken A, Heirendt L, Magnusdottir S, Ravcheev DA, Sahoo S, Gawron P, Friscioni L, Garcia B, Prendergast M, Puente A, Rodrigues M, Roy A, Rouquaya M, Wiltgen L, Zagare A, John E, Krueger M, Kuperstein I, Zinovyev A, Schneider R, Fleming RMT, Thiele I: The Virtual Metabolic Human database: integrating human and gut microbiome metabolism with nutrition and disease. Nucleic Acids Res. 2019 Jan 8;47(D1):D614-D624. doi: 10.1093/nar/gky992. [PubMed:30371894 ]

Showing metabocard for Linoleoyl ethanolamide (MMDBc0000839)

MOL for #<Metabolite:0x00007f923fa3f5d8>

3D MOL for #<Metabolite:0x00007f923fa3f5d8>

3D SDF for #<Metabolite:0x00007f923fa3f5d8>

3D-SDF for #<Metabolite:0x00007f923fa3f5d8>

PDB for #<Metabolite:0x00007f923fa3f5d8>

3D PDB for #<Metabolite:0x00007f923fa3f5d8>

SMILES for #<Metabolite:0x00007f923fa3f5d8>

INCHI for #<Metabolite:0x00007f923fa3f5d8>

Structure for #<Metabolite:0x00007f923fa3f5d8>

3D Structure for #<Metabolite:0x00007f923fa3f5d8>