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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2011-07-06 14:02:43 UTC

Update Date

2022-03-07 02:51:34 UTC

HMDB ID

HMDB0013649

Secondary Accession Numbers

HMDB13649

Metabolite Identification

Common Name

Eicosapentaenoyl Ethanolamide

Description

Eicosapentaenoyl Ethanolamide (EPEA) is an endogenous fatty acid amide. EPEA is metabolized by fatty acid amide hydrolase (FAAH) and N-acylethanolamine-hydrolyzing acid amidase (NAAA), the latter of which has more specificity toward PEA over other fatty acid amides. DHEA and eicosapentaenoyl ethanolamide (EPEA) bind to the CB1 receptor in rat brains.23 DHA levels in the mouse brain have been shown to inversely affect the levels of 2AG.

Structure

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

HMDB0013649
     RDKit          3D
Eicosapentaenoyl Ethanolamide
 60 59  0  0  0  0  0  0  0  0999 V2000
   -7.5594    1.9921    1.8589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2133    0.7742    1.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5903    0.5665   -0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9338   -0.5152   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7223   -1.6778    0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4504   -2.1692    0.7843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2784   -1.6650    0.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9392   -0.3896   -0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2080    0.4455    0.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9934    0.8293    0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3181    0.4694   -0.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1442   -0.3504   -0.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0547   -0.0295   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3880    1.1630   -1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2964    1.9908   -0.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5086    2.3472   -0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1380    1.9631   -2.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3841    1.1354   -1.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9805   -0.0759   -0.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1941   -0.8665   -0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3229   -0.4502   -0.9514 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0611   -2.0562    0.1698 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2052   -2.8575    0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1275   -2.0433    1.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2617   -2.7920    1.7767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1357    2.9150    1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5416    2.1667    1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5330    1.8551    2.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2833    1.0870    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2857   -0.0667    1.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6829    1.3953   -0.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5789   -0.4937   -1.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1998   -2.5858   -0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4402   -1.7032    1.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4689   -3.1400    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4005   -2.2170    1.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7595    0.1544   -0.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646   -0.6773   -0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7146    0.7107    1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4429    1.4285    1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9619    1.5129   -0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865    0.0993   -1.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2911   -1.2767    0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8943   -0.6765   -0.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9180    0.7675   -2.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6104    1.8226   -1.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8631    2.2967    0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0533    2.9512   -0.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5392    2.9005   -2.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5429    1.4150   -2.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
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    6.0935    1.7437   -1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.2732   -0.7140   -1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1024   -2.3750    0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7320   -3.2195   -0.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8866   -3.7368    1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4769   -1.1260    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5897   -1.8098    2.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3798   -3.5176    1.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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  2  0
 13 14  1  0
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 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
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 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 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
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  9 39  1  0
 10 40  1  0
 11 41  1  0
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 22 55  1  0
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 24 59  1  0
 25 60  1  0
M  END


  Mrv0541 02271200292D          

 25 24  0  0  0  0            999 V2000
    4.1014   -7.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8160   -6.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5304   -7.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2450   -7.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.9595   -6.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.6740   -7.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3885   -7.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1031   -6.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8176   -7.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5322   -7.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2466   -6.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.9612   -7.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.6757   -7.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.3902   -6.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   14.8193   -7.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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   16.2484   -7.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.9630   -6.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.6774   -7.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.3920   -6.6097    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   17.6774   -7.8473    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.8210   -6.6097    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1065   -7.0222    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.5354   -7.0222    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  2  3  1  0  0  0  0
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  9 10  2  0  0  0  0
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 20 22  2  0  0  0  0
 24 23  1  0  0  0  0
 21 24  1  0  0  0  0
 25 23  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013649

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO

> <INCHI_IDENTIFIER>
InChI=1S/C22H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h3-4,6-7,9-10,12-13,15-16,24H,2,5,8,11,14,17-21H2,1H3,(H,23,25)/b4-3-,7-6-,10-9-,13-12-,16-15-

> <INCHI_KEY>
OVKKNJPJQKTXIT-JLNKQSITSA-N

> <FORMULA>
C22H35NO2

> <MOLECULAR_WEIGHT>
345.5188

> <EXACT_MASS>
345.266779369

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
41.7443797700798

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(5Z,8Z,11Z,14Z,17Z)-N-(2-hydroxyethyl)icosa-5,8,11,14,17-pentaenamide

> <ALOGPS_LOGP>
5.78

> <JCHEM_LOGP>
4.951880594333334

> <ALOGPS_LOGS>
-5.49

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.375825066097114

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.435299736387666

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3386470618583667

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
114.08179999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.11e-03 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(5Z,8Z,11Z,14Z,17Z)-N-(2-hydroxyethyl)icosa-5,8,11,14,17-pentaenamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013649
     RDKit          3D
Eicosapentaenoyl Ethanolamide
 60 59  0  0  0  0  0  0  0  0999 V2000
   -7.5594    1.9921    1.8589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2133    0.7742    1.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5903    0.5665   -0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9338   -0.5152   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7223   -1.6778    0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4504   -2.1692    0.7843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2784   -1.6650    0.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9392   -0.3896   -0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2080    0.4455    0.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9934    0.8293    0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3181    0.4694   -0.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1442   -0.3504   -0.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0547   -0.0295   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3880    1.1630   -1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2964    1.9908   -0.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5086    2.3472   -0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1380    1.9631   -2.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3841    1.1354   -1.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9805   -0.0759   -0.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1941   -0.8665   -0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3229   -0.4502   -0.9514 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0611   -2.0562    0.1698 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2052   -2.8575    0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1275   -2.0433    1.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2617   -2.7920    1.7767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1357    2.9150    1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5416    2.1667    1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5330    1.8551    2.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2833    1.0870    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2857   -0.0667    1.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6829    1.3953   -0.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5789   -0.4937   -1.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1998   -2.5858   -0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4402   -1.7032    1.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4689   -3.1400    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4005   -2.2170    1.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7595    0.1544   -0.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646   -0.6773   -0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7146    0.7107    1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4429    1.4285    1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9619    1.5129   -0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865    0.0993   -1.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2911   -1.2767    0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8943   -0.6765   -0.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9180    0.7675   -2.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6104    1.8226   -1.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8631    2.2967    0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0533    2.9512   -0.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5392    2.9005   -2.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5429    1.4150   -2.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8885    0.8010   -2.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0935    1.7437   -1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4561    0.2085    0.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2732   -0.7140   -1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1024   -2.3750    0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7320   -3.2195   -0.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8866   -3.7368    1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4769   -1.1260    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5897   -1.8098    2.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3798   -3.5176    1.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 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
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  0
M  END

HEADER    PROTEIN                                 27-FEB-12   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-FEB-12         0                                  
HETATM    1  C   UNK     0       7.656 -13.108   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       8.990 -12.338   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.323 -13.108   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      11.657 -13.108   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      12.991 -12.338   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.325 -13.108   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      15.659 -13.108   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      16.992 -12.338   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.326 -13.108   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      19.660 -13.108   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      20.994 -12.338   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.328 -13.108   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      23.661 -13.108   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      24.995 -12.338   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.329 -13.108   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      27.663 -13.108   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      28.997 -12.338   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.330 -13.108   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      31.664 -12.338   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      32.998 -13.108   0.000  0.00  0.00           C+0
HETATM   21  N   UNK     0      34.332 -12.338   0.000  0.00  0.00           N+0
HETATM   22  O   UNK     0      32.998 -14.648   0.000  0.00  0.00           O+0
HETATM   23  C   UNK     0      36.999 -12.338   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      35.666 -13.108   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      38.333 -13.108   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                                                       
CONECT   19   18   20                                                       
CONECT   20   19   21   22                                                  
CONECT   21   20   24                                                       
CONECT   22   20                                                            
CONECT   23   24   25                                                       
CONECT   24   23   21                                                       
CONECT   25   23                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

COMPND    HMDB0013649
HETATM    1  C1  UNL     1      -7.559   1.992   1.859  1.00  0.00           C  
HETATM    2  C2  UNL     1      -8.213   0.774   1.227  1.00  0.00           C  
HETATM    3  C3  UNL     1      -7.590   0.566  -0.076  1.00  0.00           C  
HETATM    4  C4  UNL     1      -6.934  -0.515  -0.459  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.722  -1.678   0.350  1.00  0.00           C  
HETATM    6  C6  UNL     1      -5.450  -2.169   0.784  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.278  -1.665   0.614  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.939  -0.390  -0.099  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.208   0.446   0.908  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.993   0.829   0.643  1.00  0.00           C  
HETATM   11  C11 UNL     1      -1.318   0.469  -0.623  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.144  -0.350  -0.255  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.055  -0.029  -0.593  1.00  0.00           C  
HETATM   14  C14 UNL     1       1.388   1.163  -1.372  1.00  0.00           C  
HETATM   15  C15 UNL     1       2.296   1.991  -0.511  1.00  0.00           C  
HETATM   16  C16 UNL     1       3.509   2.347  -0.813  1.00  0.00           C  
HETATM   17  C17 UNL     1       4.138   1.963  -2.077  1.00  0.00           C  
HETATM   18  C18 UNL     1       5.384   1.135  -1.707  1.00  0.00           C  
HETATM   19  C19 UNL     1       4.980  -0.076  -0.925  1.00  0.00           C  
HETATM   20  C20 UNL     1       6.194  -0.867  -0.573  1.00  0.00           C  
HETATM   21  O1  UNL     1       7.323  -0.450  -0.951  1.00  0.00           O  
HETATM   22  N1  UNL     1       6.061  -2.056   0.170  1.00  0.00           N  
HETATM   23  C21 UNL     1       7.205  -2.857   0.539  1.00  0.00           C  
HETATM   24  C22 UNL     1       8.128  -2.043   1.392  1.00  0.00           C  
HETATM   25  O2  UNL     1       9.262  -2.792   1.777  1.00  0.00           O  
HETATM   26  H1  UNL     1      -8.136   2.915   1.643  1.00  0.00           H  
HETATM   27  H2  UNL     1      -6.542   2.167   1.443  1.00  0.00           H  
HETATM   28  H3  UNL     1      -7.533   1.855   2.963  1.00  0.00           H  
HETATM   29  H4  UNL     1      -9.283   1.087   1.015  1.00  0.00           H  
HETATM   30  H5  UNL     1      -8.286  -0.067   1.899  1.00  0.00           H  
HETATM   31  H6  UNL     1      -7.683   1.395  -0.797  1.00  0.00           H  
HETATM   32  H7  UNL     1      -6.579  -0.494  -1.513  1.00  0.00           H  
HETATM   33  H8  UNL     1      -7.200  -2.586  -0.225  1.00  0.00           H  
HETATM   34  H9  UNL     1      -7.440  -1.703   1.261  1.00  0.00           H  
HETATM   35  H10 UNL     1      -5.469  -3.140   1.360  1.00  0.00           H  
HETATM   36  H11 UNL     1      -3.400  -2.217   1.032  1.00  0.00           H  
HETATM   37  H12 UNL     1      -4.759   0.154  -0.527  1.00  0.00           H  
HETATM   38  H13 UNL     1      -3.265  -0.677  -0.916  1.00  0.00           H  
HETATM   39  H14 UNL     1      -3.715   0.711   1.840  1.00  0.00           H  
HETATM   40  H15 UNL     1      -1.443   1.429   1.355  1.00  0.00           H  
HETATM   41  H16 UNL     1      -0.962   1.513  -0.987  1.00  0.00           H  
HETATM   42  H17 UNL     1      -1.886   0.099  -1.448  1.00  0.00           H  
HETATM   43  H18 UNL     1      -0.291  -1.277   0.334  1.00  0.00           H  
HETATM   44  H19 UNL     1       1.894  -0.676  -0.288  1.00  0.00           H  
HETATM   45  H20 UNL     1       1.918   0.767  -2.289  1.00  0.00           H  
HETATM   46  H21 UNL     1       0.610   1.823  -1.709  1.00  0.00           H  
HETATM   47  H22 UNL     1       1.863   2.297   0.437  1.00  0.00           H  
HETATM   48  H23 UNL     1       4.053   2.951  -0.086  1.00  0.00           H  
HETATM   49  H24 UNL     1       4.539   2.901  -2.601  1.00  0.00           H  
HETATM   50  H25 UNL     1       3.543   1.415  -2.782  1.00  0.00           H  
HETATM   51  H26 UNL     1       5.888   0.801  -2.629  1.00  0.00           H  
HETATM   52  H27 UNL     1       6.094   1.744  -1.141  1.00  0.00           H  
HETATM   53  H28 UNL     1       4.456   0.208   0.028  1.00  0.00           H  
HETATM   54  H29 UNL     1       4.273  -0.714  -1.473  1.00  0.00           H  
HETATM   55  H30 UNL     1       5.102  -2.375   0.467  1.00  0.00           H  
HETATM   56  H31 UNL     1       7.732  -3.219  -0.388  1.00  0.00           H  
HETATM   57  H32 UNL     1       6.887  -3.737   1.136  1.00  0.00           H  
HETATM   58  H33 UNL     1       8.477  -1.126   0.926  1.00  0.00           H  
HETATM   59  H34 UNL     1       7.590  -1.810   2.345  1.00  0.00           H  
HETATM   60  H35 UNL     1       9.380  -3.518   1.085  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4    4   31
CONECT    4    5   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   13   43
CONECT   13   14   44
CONECT   14   15   45   46
CONECT   15   16   16   47
CONECT   16   17   48
CONECT   17   18   49   50
CONECT   18   19   51   52
CONECT   19   20   53   54
CONECT   20   21   21   22
CONECT   22   23   55
CONECT   23   24   56   57
CONECT   24   25   58   59
CONECT   25   60
END

HMDB0013649
     RDKit          3D
Eicosapentaenoyl Ethanolamide
 60 59  0  0  0  0  0  0  0  0999 V2000
   -7.5594    1.9921    1.8589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2133    0.7742    1.2272 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5903    0.5665   -0.0756 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9338   -0.5152   -0.4589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7223   -1.6778    0.3501 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4504   -2.1692    0.7843 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2784   -1.6650    0.6139 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.9392   -0.3896   -0.0988 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2080    0.4455    0.9084 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9934    0.8293    0.6432 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3181    0.4694   -0.6233 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1442   -0.3504   -0.2551 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0547   -0.0295   -0.5928 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3880    1.1630   -1.3716 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2964    1.9908   -0.5111 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5086    2.3472   -0.8133 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1380    1.9631   -2.0770 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3841    1.1354   -1.7075 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9805   -0.0759   -0.9247 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1941   -0.8665   -0.5732 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3229   -0.4502   -0.9514 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.0611   -2.0562    0.1698 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2052   -2.8575    0.5386 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1275   -2.0433    1.3924 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.2617   -2.7920    1.7767 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1357    2.9150    1.6432 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5416    2.1667    1.4427 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5330    1.8551    2.9631 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2833    1.0870    1.0153 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2857   -0.0667    1.8992 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6829    1.3953   -0.7965 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.5789   -0.4937   -1.5133 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1998   -2.5858   -0.2253 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4402   -1.7032    1.2609 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.4689   -3.1400    1.3605 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4005   -2.2170    1.0321 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7595    0.1544   -0.5266 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2646   -0.6773   -0.9157 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7146    0.7107    1.8401 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4429    1.4285    1.3548 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9619    1.5129   -0.9873 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8865    0.0993   -1.4478 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2911   -1.2767    0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8943   -0.6765   -0.2882 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9180    0.7675   -2.2893 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6104    1.8226   -1.7087 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8631    2.2967    0.4374 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0533    2.9512   -0.0863 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5392    2.9005   -2.6012 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5429    1.4150   -2.7817 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8885    0.8010   -2.6289 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0935    1.7437   -1.1414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4561    0.2085    0.0279 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.2732   -0.7140   -1.4735 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1024   -2.3750    0.4675 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7320   -3.2195   -0.3881 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8866   -3.7368    1.1356 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.4769   -1.1260    0.9265 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.5897   -1.8098    2.3448 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3798   -3.5176    1.0850 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  2  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  2  0
 13 14  1  0
 14 15  1  0
 15 16  2  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 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
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 16 48  1  0
 17 49  1  0
 17 50  1  0
 18 51  1  0
 18 52  1  0
 19 53  1  0
 19 54  1  0
 22 55  1  0
 23 56  1  0
 23 57  1  0
 24 58  1  0
 24 59  1  0
 25 60  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(5Z,8Z,11Z,14Z,17Z)-Eicosapentaenoyl ethanolamide	ChEBI
(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl) ethanolamine	ChEBI
all-cis-Eicosa-5,8,11,14,17-pentaenoyl ethanolamide	ChEBI
all-cis-Icosa-5,8,11,14,17-pentaenoyl ethanolamide	ChEBI
Anandamide (20:5, N-3)	ChEBI
EPEA	ChEBI
Icosapentaenoyl ethanolamide	ChEBI
N-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)ethanolamine	ChEBI
N-cis-5,8, 11,14,17-Eicosapentaenoylethanolamine	ChEBI
(5Z,8Z,11Z,14Z,17Z)-Icosapentaenoyl ethanolamide	ChEBI, HMDB
Eicosapentaenoyl ethanolamide	ChEBI
N-(2-Hydroxyethyl)-5Z,8Z,11Z,14Z,17Z-eicosapentaenamide	HMDB
N-(5Z,8Z,11Z,14Z,17Z-Eicosapentaenoyl)-ethanolamine	HMDB

Chemical Formula

C₂₂H₃₅NO₂

Average Molecular Weight

345.5188

Monoisotopic Molecular Weight

345.266779369

IUPAC Name

(5Z,8Z,11Z,14Z,17Z)-N-(2-hydroxyethyl)icosa-5,8,11,14,17-pentaenamide

Traditional Name

(5Z,8Z,11Z,14Z,17Z)-N-(2-hydroxyethyl)icosa-5,8,11,14,17-pentaenamide

CAS Registry Number

109001-03-8

SMILES

CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO

InChI Identifier

InChI=1S/C22H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h3-4,6-7,9-10,12-13,15-16,24H,2,5,8,11,14,17-21H2,1H3,(H,23,25)/b4-3-,7-6-,10-9-,13-12-,16-15-

InChI Key

OVKKNJPJQKTXIT-JLNKQSITSA-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:71467 )
N-(long-chain-acyl)ethanolamine (CHEBI:71467 )
endocannabinoid (CHEBI:71467 )
N-acyl ethanolamines (endocannabinoids) (LMFA08040008 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cell membrane (HMDB: HMDB0013649)

Cellular substructure

Extracellular (HMDB: HMDB0013649)
Membrane (HMDB: HMDB0013649)

Source

Endogenous

Endogenous (HMDB: HMDB0013649)

Exogenous

Food

Food (HMDB: HMDB0013649)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0013649)

Role

Biological role

Energy source (HMDB: HMDB0013649)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013649)

Emulsifier (HMDB: HMDB0013649)

Physical Properties

State

Solid

Experimental Molecular Properties

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

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.0011 g/L	ALOGPS
logP	5.78	ALOGPS
logP	4.95	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	15.44	ChemAxon
pKa (Strongest Basic)	-0.34	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	114.08 m³·mol⁻¹	ChemAxon
Polarizability	41.74 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	195.673	31661259
DarkChem	[M-H]-	194.361	31661259
DeepCCS	[M+H]+	185.972	30932474
DeepCCS	[M-H]-	183.614	30932474
DeepCCS	[M-2H]-	217.548	30932474
DeepCCS	[M+Na]+	192.775	30932474
AllCCS	[M+H]+	192.6	32859911
AllCCS	[M+H-H2O]+	189.9	32859911
AllCCS	[M+NH4]+	195.1	32859911
AllCCS	[M+Na]+	195.8	32859911
AllCCS	[M-H]-	190.7	32859911
AllCCS	[M+Na-2H]-	192.8	32859911
AllCCS	[M+HCOO]-	195.4	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Eicosapentaenoyl Ethanolamide	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO	3555.8	Standard polar	33892256
Eicosapentaenoyl Ethanolamide	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO	2561.8	Standard non polar	33892256
Eicosapentaenoyl Ethanolamide	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCCC(=O)NCCO	2853.1	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Eicosapentaenoyl Ethanolamide,1TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO[Si](C)(C)C	2867.9	Semi standard non polar	33892256
Eicosapentaenoyl Ethanolamide,1TMS,isomer #2	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO)[Si](C)(C)C	2782.2	Semi standard non polar	33892256
Eicosapentaenoyl Ethanolamide,2TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2833.8	Semi standard non polar	33892256
Eicosapentaenoyl Ethanolamide,2TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2905.8	Standard non polar	33892256
Eicosapentaenoyl Ethanolamide,2TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2830.2	Standard polar	33892256
Eicosapentaenoyl Ethanolamide,1TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)NCCO[Si](C)(C)C(C)(C)C	3120.5	Semi standard non polar	33892256
Eicosapentaenoyl Ethanolamide,1TBDMS,isomer #2	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C	3048.1	Semi standard non polar	33892256
Eicosapentaenoyl Ethanolamide,2TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3341.3	Semi standard non polar	33892256
Eicosapentaenoyl Ethanolamide,2TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3273.8	Standard non polar	33892256
Eicosapentaenoyl Ethanolamide,2TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2886.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Eicosapentaenoyl Ethanolamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-01p2-6594000000-f16f4f504f500b82ebdf	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eicosapentaenoyl Ethanolamide GC-MS (1 TMS) - 70eV, Positive	splash10-0fk9-9362200000-1320e1056324d323f57d	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eicosapentaenoyl Ethanolamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Eicosapentaenoyl Ethanolamide 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 - Eicosapentaenoyl Ethanolamide 10V, Positive-QTOF	splash10-01ot-5149000000-eed2dcb29f49f2289844	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoyl Ethanolamide 20V, Positive-QTOF	splash10-03dl-9120000000-9305609c724a4878191a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoyl Ethanolamide 40V, Positive-QTOF	splash10-03di-9230000000-b5cc9e1615f5477bbea7	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoyl Ethanolamide 10V, Negative-QTOF	splash10-0006-0009000000-d4f7e87c45bcc63e17d2	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoyl Ethanolamide 20V, Negative-QTOF	splash10-01ox-6029000000-a540e5c0d137b5a0ac56	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoyl Ethanolamide 40V, Negative-QTOF	splash10-0006-9010000000-d0d8fe150594c5c85530	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoyl Ethanolamide 10V, Positive-QTOF	splash10-01ot-9328000000-0506718ab0ac845ed26c	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoyl Ethanolamide 20V, Positive-QTOF	splash10-03dl-9100000000-91289ad1e6e9f4611068	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoyl Ethanolamide 40V, Positive-QTOF	splash10-03dl-9200000000-c7fc186fa971397efe35	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoyl Ethanolamide 10V, Negative-QTOF	splash10-0006-0009000000-d32eeee3dd6dfdbb595f	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoyl Ethanolamide 20V, Negative-QTOF	splash10-0006-5129000000-f853d05861110dbe6a72	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Eicosapentaenoyl Ethanolamide 40V, Negative-QTOF	splash10-052f-9020000000-d61a052479cd2fd9d23e	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Not Available

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029619

KNApSAcK ID

Not Available

Chemspider ID

4446570

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283450

PDB ID

Not Available

ChEBI ID

71467

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

Balvers MG, Verhoeckx KC, Plastina P, Wortelboer HM, Meijerink J, Witkamp RF: Docosahexaenoic acid and eicosapentaenoic acid are converted by 3T3-L1 adipocytes to N-acyl ethanolamines with anti-inflammatory properties. Biochim Biophys Acta. 2010 Oct;1801(10):1107-14. doi: 10.1016/j.bbalip.2010.06.006. Epub 2010 Jun 27. [PubMed:20601112 ]

Showing metabocard for Eicosapentaenoyl Ethanolamide (HMDB0013649)

MOL for HMDB0013649 (Eicosapentaenoyl Ethanolamide)

3D MOL for HMDB0013649 (Eicosapentaenoyl Ethanolamide)

3D SDF for HMDB0013649 (Eicosapentaenoyl Ethanolamide)

3D-SDF for HMDB0013649 (Eicosapentaenoyl Ethanolamide)

PDB for HMDB0013649 (Eicosapentaenoyl Ethanolamide)

3D PDB for HMDB0013649 (Eicosapentaenoyl Ethanolamide)

SMILES for HMDB0013649 (Eicosapentaenoyl Ethanolamide)

INCHI for HMDB0013649 (Eicosapentaenoyl Ethanolamide)

Structure for HMDB0013649 (Eicosapentaenoyl Ethanolamide)

3D Structure for HMDB0013649 (Eicosapentaenoyl Ethanolamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra