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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2010-05-20 13:03:28 UTC

Update Date

2022-03-07 02:51:34 UTC

HMDB ID

HMDB0013627

Secondary Accession Numbers

HMDB13627

Metabolite Identification

Common Name

Cervonoyl ethanolamide

Description

Cervonoyl ethanolamide is a 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 has been attributed a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. N-oleoylethanolamine is an inhibitor of the sphingolipid signaling pathway, via specific ceramidase inhibition (ceramidase converts ceramide to sphingosine). N-oleoylethanolamine blocks the effects of TNF- and arachidonic acid on intracellular Ca concentration. (PMID: 12692337 , 12056855 , 12560208 , 11997249 ).

Structure

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


  Mrv0541 02271200282D          

 27 26  0  0  0  0            999 V2000
    4.3147  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7437  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4582  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1727  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8871  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6016  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3161  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0305  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7450  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4595  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1740  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8885  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6029  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3174  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0319  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7464  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4608  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1754  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8898  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6043  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3188  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0332  -15.6826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3188  -14.4451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7477  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4622  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1767  -15.2701    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  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
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 25 23  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
M  END

HMDB0013627
     RDKit          3D
Cervonoyl ethanolamide
 63 62  0  0  0  0  0  0  0  0999 V2000
    9.6301    0.1657    0.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3266    0.5410    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5675    1.4518    0.8579 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4014    1.2490    1.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5052    0.1022    1.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8984   -1.0840    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3390   -1.6135   -0.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1266   -1.1030   -1.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1603   -2.2223   -1.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9753   -2.2245   -0.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1789   -1.2423   -0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6061    0.0587    0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1755    1.1920   -0.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1672    1.5243   -1.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5215    0.4741   -1.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8221    0.2269   -1.9844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7975    1.0207   -1.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8179    1.6473   -2.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0916    1.3518   -1.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6461    0.4338   -0.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6176    1.1104   -0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0972    0.0442    0.9127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6880   -1.1403    0.8201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9903    0.3832    1.8841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5101   -0.5182    2.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2769   -1.6041    2.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3243   -0.9772    1.4292 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2186    1.0767    0.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2143   -0.5065    0.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4270   -0.3960    1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8992   -0.3421   -0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7731    1.1713   -0.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0949    2.4461    1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0220    2.1210    1.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5283    0.5430    0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1169   -0.1860    2.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7682   -1.6534    0.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8165   -2.5496   -0.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4159   -0.8925   -2.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7386   -0.2458   -0.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5543   -3.1907   -1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4335   -3.2304   -0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9309   -1.7573    0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1201   -1.2711   -0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3633    0.1307    1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6739    2.1004    0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    2.1878   -2.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5415    2.2326   -0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0445   -0.2479   -2.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2133   -0.6250   -2.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2983    1.8740   -0.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2409    0.4400   -0.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4798    2.3537   -2.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7639    1.8756   -2.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3324   -0.2670   -1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9941   -0.2339   -0.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4740    1.5010   -0.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1653    1.9473    0.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2204    0.0053    3.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6908   -0.9841    3.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6599   -2.1335    1.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7005   -2.3317    2.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8905   -0.2096    0.9516 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  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 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
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 25 59  1  0
 25 60  1  0
 26 61  1  0
 26 62  1  0
 27 63  1  0
M  END


  Mrv0541 02271200282D          

 27 26  0  0  0  0            999 V2000
    4.3147  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.0292  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.7437  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4582  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.1727  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.8871  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6016  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3161  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0305  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.7450  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.4595  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1740  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.8885  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6029  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3174  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0319  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.7464  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.4608  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.1754  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.8898  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.6043  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.3188  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.0332  -15.6826    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   19.3188  -14.4451    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   20.7477  -15.2701    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.4622  -15.6826    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.1767  -15.2701    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
  3  4  2  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  2  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  2  0  0  0  0
 10 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 13  2  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  2  0  0  0  0
 16 17  1  0  0  0  0
 17 18  1  0  0  0  0
 18 19  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
 22 23  1  0  0  0  0
 22 24  2  0  0  0  0
 25 23  1  0  0  0  0
 26 25  1  0  0  0  0
 27 26  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013627

> <DATABASE_NAME>
hmdb

> <SMILES>
CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)OCCO

> <INCHI_IDENTIFIER>
InChI=1S/C24H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(26)27-23-22-25/h3-4,6-7,9-10,12-13,15-16,18-19,25H,2,5,8,11,14,17,20-23H2,1H3/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-

> <INCHI_KEY>
CXWASNUDKUTFPQ-KUBAVDMBSA-N

> <FORMULA>
C24H36O3

> <MOLECULAR_WEIGHT>
372.5408

> <EXACT_MASS>
372.266445018

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
43.57822893811415

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
2-hydroxyethyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate

> <ALOGPS_LOGP>
6.39

> <JCHEM_LOGP>
6.208256871666666

> <ALOGPS_LOGS>
-6.19

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.096551894146636

> <JCHEM_PKA_STRONGEST_BASIC>
-2.7565682015002624

> <JCHEM_POLAR_SURFACE_AREA>
46.53

> <JCHEM_REFRACTIVITY>
122.4506

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.42e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2-hydroxyethyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013627
     RDKit          3D
Cervonoyl ethanolamide
 63 62  0  0  0  0  0  0  0  0999 V2000
    9.6301    0.1657    0.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3266    0.5410    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5675    1.4518    0.8579 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4014    1.2490    1.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5052    0.1022    1.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8984   -1.0840    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3390   -1.6135   -0.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1266   -1.1030   -1.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1603   -2.2223   -1.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9753   -2.2245   -0.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1789   -1.2423   -0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6061    0.0587    0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1755    1.1920   -0.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1672    1.5243   -1.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5215    0.4741   -1.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8221    0.2269   -1.9844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7975    1.0207   -1.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8179    1.6473   -2.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0916    1.3518   -1.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6461    0.4338   -0.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6176    1.1104   -0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0972    0.0442    0.9127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6880   -1.1403    0.8201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9903    0.3832    1.8841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5101   -0.5182    2.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2769   -1.6041    2.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3243   -0.9772    1.4292 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2186    1.0767    0.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2143   -0.5065    0.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4270   -0.3960    1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8992   -0.3421   -0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7731    1.1713   -0.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0949    2.4461    1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0220    2.1210    1.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5283    0.5430    0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1169   -0.1860    2.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7682   -1.6534    0.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8165   -2.5496   -0.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4159   -0.8925   -2.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7386   -0.2458   -0.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5543   -3.1907   -1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4335   -3.2304   -0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9309   -1.7573    0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1201   -1.2711   -0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3633    0.1307    1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6739    2.1004    0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    2.1878   -2.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5415    2.2326   -0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0445   -0.2479   -2.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2133   -0.6250   -2.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2983    1.8740   -0.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2409    0.4400   -0.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4798    2.3537   -2.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7639    1.8756   -2.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3324   -0.2670   -1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9941   -0.2339   -0.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4740    1.5010   -0.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1653    1.9473    0.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2204    0.0053    3.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6908   -0.9841    3.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6599   -2.1335    1.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7005   -2.3317    2.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8905   -0.2096    0.9516 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  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 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
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 25 59  1  0
 25 60  1  0
 26 61  1  0
 26 62  1  0
 27 63  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       8.054 -29.274   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0       9.388 -28.504   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      10.722 -29.274   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      12.055 -29.274   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      13.389 -28.504   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      14.723 -29.274   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      16.056 -29.274   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      17.390 -28.504   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      18.724 -29.274   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      20.057 -29.274   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      21.391 -28.504   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.725 -29.274   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      24.059 -29.274   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      25.392 -28.504   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      26.726 -29.274   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      28.060 -29.274   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      29.393 -28.504   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      30.727 -29.274   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      32.061 -29.274   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      33.394 -28.504   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      34.728 -29.274   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      36.062 -28.504   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      37.395 -29.274   0.000  0.00  0.00           O+0
HETATM   24  O   UNK     0      36.062 -26.964   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      38.729 -28.504   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      40.063 -29.274   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      41.397 -28.504   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                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23   24                                                  
CONECT   23   22   25                                                       
CONECT   24   22                                                            
CONECT   25   23   26                                                       
CONECT   26   25   27                                                       
CONECT   27   26                                                            
MASTER        0    0    0    0    0    0    0    0   27    0   52    0
END

COMPND    HMDB0013627
HETATM    1  C1  UNL     1       9.630   0.166   0.735  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.327   0.541   0.001  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.568   1.452   0.858  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.401   1.249   1.349  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.505   0.102   1.225  1.00  0.00           C  
HETATM    6  C6  UNL     1       5.898  -1.084   0.520  1.00  0.00           C  
HETATM    7  C7  UNL     1       5.339  -1.614  -0.532  1.00  0.00           C  
HETATM    8  C8  UNL     1       4.127  -1.103  -1.262  1.00  0.00           C  
HETATM    9  C9  UNL     1       3.160  -2.222  -1.289  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.975  -2.224  -0.832  1.00  0.00           C  
HETATM   11  C11 UNL     1       1.179  -1.242  -0.170  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.606   0.059   0.211  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.176   1.192  -0.248  1.00  0.00           C  
HETATM   14  C14 UNL     1       0.167   1.524  -1.259  1.00  0.00           C  
HETATM   15  C15 UNL     1      -0.522   0.474  -1.972  1.00  0.00           C  
HETATM   16  C16 UNL     1      -1.822   0.227  -1.984  1.00  0.00           C  
HETATM   17  C17 UNL     1      -2.797   1.021  -1.242  1.00  0.00           C  
HETATM   18  C18 UNL     1      -3.818   1.647  -2.131  1.00  0.00           C  
HETATM   19  C19 UNL     1      -5.092   1.352  -1.978  1.00  0.00           C  
HETATM   20  C20 UNL     1      -5.646   0.434  -0.988  1.00  0.00           C  
HETATM   21  C21 UNL     1      -6.618   1.110  -0.037  1.00  0.00           C  
HETATM   22  C22 UNL     1      -7.097   0.044   0.913  1.00  0.00           C  
HETATM   23  O1  UNL     1      -6.688  -1.140   0.820  1.00  0.00           O  
HETATM   24  O2  UNL     1      -7.990   0.383   1.884  1.00  0.00           O  
HETATM   25  C23 UNL     1      -8.510  -0.518   2.820  1.00  0.00           C  
HETATM   26  C24 UNL     1      -9.277  -1.604   2.140  1.00  0.00           C  
HETATM   27  O3  UNL     1     -10.324  -0.977   1.429  1.00  0.00           O  
HETATM   28  H1  UNL     1      10.219   1.077   0.850  1.00  0.00           H  
HETATM   29  H2  UNL     1      10.214  -0.507   0.052  1.00  0.00           H  
HETATM   30  H3  UNL     1       9.427  -0.396   1.647  1.00  0.00           H  
HETATM   31  H4  UNL     1       7.899  -0.342  -0.393  1.00  0.00           H  
HETATM   32  H5  UNL     1       8.773   1.171  -0.885  1.00  0.00           H  
HETATM   33  H6  UNL     1       8.095   2.446   1.100  1.00  0.00           H  
HETATM   34  H7  UNL     1       6.022   2.121   1.985  1.00  0.00           H  
HETATM   35  H8  UNL     1       4.528   0.543   0.801  1.00  0.00           H  
HETATM   36  H9  UNL     1       5.117  -0.186   2.278  1.00  0.00           H  
HETATM   37  H10 UNL     1       6.768  -1.653   0.952  1.00  0.00           H  
HETATM   38  H11 UNL     1       5.816  -2.550  -0.933  1.00  0.00           H  
HETATM   39  H12 UNL     1       4.416  -0.893  -2.339  1.00  0.00           H  
HETATM   40  H13 UNL     1       3.739  -0.246  -0.768  1.00  0.00           H  
HETATM   41  H14 UNL     1       3.554  -3.191  -1.789  1.00  0.00           H  
HETATM   42  H15 UNL     1       1.434  -3.230  -0.984  1.00  0.00           H  
HETATM   43  H16 UNL     1       0.931  -1.757   0.891  1.00  0.00           H  
HETATM   44  H17 UNL     1       0.120  -1.271  -0.570  1.00  0.00           H  
HETATM   45  H18 UNL     1       2.363   0.131   1.034  1.00  0.00           H  
HETATM   46  H19 UNL     1       1.674   2.100   0.222  1.00  0.00           H  
HETATM   47  H20 UNL     1       0.654   2.188  -2.067  1.00  0.00           H  
HETATM   48  H21 UNL     1      -0.542   2.233  -0.789  1.00  0.00           H  
HETATM   49  H22 UNL     1       0.044  -0.248  -2.633  1.00  0.00           H  
HETATM   50  H23 UNL     1      -2.213  -0.625  -2.586  1.00  0.00           H  
HETATM   51  H24 UNL     1      -2.298   1.874  -0.745  1.00  0.00           H  
HETATM   52  H25 UNL     1      -3.241   0.440  -0.408  1.00  0.00           H  
HETATM   53  H26 UNL     1      -3.480   2.354  -2.908  1.00  0.00           H  
HETATM   54  H27 UNL     1      -5.764   1.876  -2.693  1.00  0.00           H  
HETATM   55  H28 UNL     1      -6.332  -0.267  -1.590  1.00  0.00           H  
HETATM   56  H29 UNL     1      -4.994  -0.234  -0.459  1.00  0.00           H  
HETATM   57  H30 UNL     1      -7.474   1.501  -0.621  1.00  0.00           H  
HETATM   58  H31 UNL     1      -6.165   1.947   0.513  1.00  0.00           H  
HETATM   59  H32 UNL     1      -9.220   0.005   3.518  1.00  0.00           H  
HETATM   60  H33 UNL     1      -7.691  -0.984   3.423  1.00  0.00           H  
HETATM   61  H34 UNL     1      -8.660  -2.133   1.418  1.00  0.00           H  
HETATM   62  H35 UNL     1      -9.700  -2.332   2.878  1.00  0.00           H  
HETATM   63  H36 UNL     1      -9.890  -0.210   0.952  1.00  0.00           H  
CONECT    1    2   28   29   30
CONECT    2    3   31   32
CONECT    3    4    4   33
CONECT    4    5   34
CONECT    5    6   35   36
CONECT    6    7    7   37
CONECT    7    8   38
CONECT    8    9   39   40
CONECT    9   10   10   41
CONECT   10   11   42
CONECT   11   12   43   44
CONECT   12   13   13   45
CONECT   13   14   46
CONECT   14   15   47   48
CONECT   15   16   16   49
CONECT   16   17   50
CONECT   17   18   51   52
CONECT   18   19   19   53
CONECT   19   20   54
CONECT   20   21   55   56
CONECT   21   22   57   58
CONECT   22   23   23   24
CONECT   24   25
CONECT   25   26   59   60
CONECT   26   27   61   62
CONECT   27   63
END

HMDB0013627
     RDKit          3D
Cervonoyl ethanolamide
 63 62  0  0  0  0  0  0  0  0999 V2000
    9.6301    0.1657    0.7349 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.3266    0.5410    0.0010 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5675    1.4518    0.8579 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.4014    1.2490    1.3492 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5052    0.1022    1.2249 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8984   -1.0840    0.5204 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3390   -1.6135   -0.5320 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.1266   -1.1030   -1.2619 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.1603   -2.2223   -1.2894 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.9753   -2.2245   -0.8319 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1789   -1.2423   -0.1699 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6061    0.0587    0.2112 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1755    1.1920   -0.2476 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.1672    1.5243   -1.2589 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5215    0.4741   -1.9717 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8221    0.2269   -1.9844 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7975    1.0207   -1.2417 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8179    1.6473   -2.1314 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0916    1.3518   -1.9779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6461    0.4338   -0.9881 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6176    1.1104   -0.0366 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0972    0.0442    0.9127 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.6880   -1.1403    0.8201 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9903    0.3832    1.8841 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5101   -0.5182    2.8201 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2769   -1.6041    2.1402 C   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3243   -0.9772    1.4292 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.2186    1.0767    0.8504 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.2143   -0.5065    0.0516 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.4270   -0.3960    1.6471 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.8992   -0.3421   -0.3927 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.7731    1.1713   -0.8846 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.0949    2.4461    1.1000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0220    2.1210    1.9846 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5283    0.5430    0.8009 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1169   -0.1860    2.2776 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.7682   -1.6534    0.9522 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8165   -2.5496   -0.9326 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4159   -0.8925   -2.3392 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.7386   -0.2458   -0.7679 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5543   -3.1907   -1.7889 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4335   -3.2304   -0.9836 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9309   -1.7573    0.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1201   -1.2711   -0.5705 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3633    0.1307    1.0336 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6739    2.1004    0.2216 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.6544    2.1878   -2.0670 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5415    2.2326   -0.7886 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0445   -0.2479   -2.6328 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2133   -0.6250   -2.5856 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2983    1.8740   -0.7453 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2409    0.4400   -0.4076 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4798    2.3537   -2.9082 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7639    1.8756   -2.6930 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.3324   -0.2670   -1.5897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.9941   -0.2339   -0.4595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4740    1.5010   -0.6208 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.1653    1.9473    0.5131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2204    0.0053    3.5176 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6908   -0.9841    3.4233 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.6599   -2.1335    1.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7005   -2.3317    2.8775 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8905   -0.2096    0.9516 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  2  0
 19 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  2  0
 22 24  1  0
 24 25  1  0
 25 26  1  0
 26 27  1  0
  1 28  1  0
  1 29  1  0
  1 30  1  0
  2 31  1  0
  2 32  1  0
  3 33  1  0
  4 34  1  0
  5 35  1  0
  5 36  1  0
  6 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
 13 46  1  0
 14 47  1  0
 14 48  1  0
 15 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 18 53  1  0
 19 54  1  0
 20 55  1  0
 20 56  1  0
 21 57  1  0
 21 58  1  0
 25 59  1  0
 25 60  1  0
 26 61  1  0
 26 62  1  0
 27 63  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8,11,14-Eicosatrienoylethanolamide	HMDB
DHEA	HMDB
N-(8Z,11Z,14Z-Icosatrienoyl)-ethanolamide	HMDB
2-Hydroxyethyl (7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoic acid	Generator

Chemical Formula

C₂₄H₃₆O₃

Average Molecular Weight

372.5408

Monoisotopic Molecular Weight

372.266445018

IUPAC Name

2-hydroxyethyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate

Traditional Name

2-hydroxyethyl (4Z,7Z,10Z,13Z,16Z,19Z)-docosa-4,7,10,13,16,19-hexaenoate

CAS Registry Number

Not Available

SMILES

CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)OCCO

InChI Identifier

InChI=1S/C24H36O3/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(26)27-23-22-25/h3-4,6-7,9-10,12-13,15-16,18-19,25H,2,5,8,11,14,17,20-23H2,1H3/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-

InChI Key

CXWASNUDKUTFPQ-KUBAVDMBSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as fatty acid esters. These are carboxylic ester derivatives of a fatty acid.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acid esters

Direct Parent

Fatty acid esters

Alternative Parents

Substituents

Fatty acid ester
Carboxylic acid ester
Monocarboxylic acid or derivatives
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Primary alcohol
Organooxygen compound
Carbonyl group
Alcohol
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

Not Available

Ontology

Not Available

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	0.00024 g/L	ALOGPS
logP	6.39	ALOGPS
logP	6.21	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	15.1	ChemAxon
pKa (Strongest Basic)	-2.8	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	46.53 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	122.45 m³·mol⁻¹	ChemAxon
Polarizability	43.58 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	No	ChemAxon
Rule of Five	No	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	202.087	31661259
DarkChem	[M-H]-	202.54	31661259
DeepCCS	[M+H]+	194.65	30932474
DeepCCS	[M-H]-	192.292	30932474
DeepCCS	[M-2H]-	226.419	30932474
DeepCCS	[M+Na]+	201.646	30932474
AllCCS	[M+H]+	199.4	32859911
AllCCS	[M+H-H2O]+	196.8	32859911
AllCCS	[M+NH4]+	201.7	32859911
AllCCS	[M+Na]+	202.4	32859911
AllCCS	[M-H]-	196.1	32859911
AllCCS	[M+Na-2H]-	198.5	32859911
AllCCS	[M+HCOO]-	201.3	32859911

Predicted Retention Times

Underivatized

Chromatographic Method	Retention Time	Reference
Measured using a Waters Acquity ultraperformance liquid chromatography (UPLC) ethylene-bridged hybrid (BEH) C18 column (100 mm × 2.1 mm; 1.7 μmparticle diameter). Predicted by Afia on May 17, 2022. Predicted by Afia on May 17, 2022.	4.88 minutes	32390414
Predicted by Siyang on May 30, 2022	27.5591 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	1.35 minutes	32390414
AjsUoB = Accucore 150 Amide HILIC with 10mM Ammonium Formate, 0.1% Formic Acid	41.3 seconds	40023050
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	3646.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	546.1 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	247.9 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	452.4 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	769.8 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	1314.0 seconds	40023050
BfG_NTS_RP1 =Agilent Zorbax Eclipse Plus C18 (2.1 mm x 150 mm, 3.5 um) with Water:ACN and 0.1% Formic Acid	662.9 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	97.1 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	2567.8 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	917.2 seconds	40023050
UFZ_Phenomenex = Kinetex Core-Shell C18 2.6 um, 3.0 x 100 mm, Phenomenex with Water:MeOH and 0.1% Formic Acid	2112.6 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	974.4 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	598.5 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	445.4 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	598.3 seconds	40023050
Meister zic-pHILIC pH9.3 = Merck SeQuant ZIC-pHILIC column with ACN:Water 5mM NH4Ac pH9.3 and 5mM ammonium acetate in water	9.3 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Cervonoyl ethanolamide	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)OCCO	3418.1	Standard polar	33892256
Cervonoyl ethanolamide	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)OCCO	2389.9	Standard non polar	33892256
Cervonoyl ethanolamide	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)OCCO	2819.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Cervonoyl ethanolamide,1TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)OCCO[Si](C)(C)C	2891.3	Semi standard non polar	33892256
Cervonoyl ethanolamide,1TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)OCCO[Si](C)(C)C(C)(C)C	3112.6	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Cervonoyl ethanolamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-01pk-8396000000-1d0ace2b11d6c40b1fc2	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cervonoyl ethanolamide GC-MS (1 TMS) - 70eV, Positive	splash10-0h90-9475100000-2b65ef5fc990f79bd551	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Cervonoyl 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 - Cervonoyl ethanolamide 10V, Positive-QTOF	splash10-022a-4029000000-3f41db329532c552a58b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cervonoyl ethanolamide 20V, Positive-QTOF	splash10-01ot-9285000000-1bd3653b820ae596457a	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cervonoyl ethanolamide 40V, Positive-QTOF	splash10-015a-6492000000-64839389b6d689bd9c4f	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cervonoyl ethanolamide 10V, Negative-QTOF	splash10-05i0-1009000000-772e93af60e404792c14	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cervonoyl ethanolamide 20V, Negative-QTOF	splash10-0a6u-4019000000-9b3d7464ebad01b4522b	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cervonoyl ethanolamide 40V, Negative-QTOF	splash10-052f-9023000000-4e78056ea7ac55147ea9	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cervonoyl ethanolamide 10V, Positive-QTOF	splash10-0229-3229000000-f7e676aef96eeef441cc	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cervonoyl ethanolamide 20V, Positive-QTOF	splash10-03l1-9546000000-dcada1f4b00ac93a9a4f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cervonoyl ethanolamide 40V, Positive-QTOF	splash10-05o3-7901000000-83db43f3646c8ea3ce65	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cervonoyl ethanolamide 10V, Negative-QTOF	splash10-0adi-0009000000-ab994d80fe196d45ffd2	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cervonoyl ethanolamide 20V, Negative-QTOF	splash10-0a6r-5009000000-c5255753e4ef1c3ee624	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Cervonoyl ethanolamide 40V, Negative-QTOF	splash10-05i1-8195000000-13c882cacb1117324af4	2021-09-22	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Feces

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.401 +/- 0.22 uM	Adult (>18 years old)	Both	Normal	21359215	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Iron deficiency	26848182	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Ulcerative colitis	26848182	details

Associated Disorders and Diseases

Disease References

Iron deficiency
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]
Ulcerative colitis
Lee T, Clavel T, Smirnov K, Schmidt A, Lagkouvardos I, Walker A, Lucio M, Michalke B, Schmitt-Kopplin P, Fedorak R, Haller D: Oral versus intravenous iron replacement therapy distinctly alters the gut microbiota and metabolome in patients with IBD. Gut. 2017 May;66(5):863-871. doi: 10.1136/gutjnl-2015-309940. Epub 2016 Feb 4. [PubMed:26848182 ]

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB029604

KNApSAcK ID

Not Available

Chemspider ID

30776716

KEGG Compound ID

C13828

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

53245830

PDB ID

Not Available

ChEBI ID

34488

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

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. 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. [PubMed:12692337 ]
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. [PubMed:12056855 ]
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. [PubMed:11997249 ]
Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9. [PubMed:11413487 ]
Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10. [PubMed:16902246 ]
Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20. [PubMed:17374880 ]
Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621. [PubMed:20044567 ]
Gunstone, Frank D., John L. Harwood, and Albert J. Dijkstra (2007). The lipid handbook with CD-ROM. CRC Press.

Showing metabocard for Cervonoyl ethanolamide (HMDB0013627)

MOL for HMDB0013627 (Cervonoyl ethanolamide)

3D MOL for HMDB0013627 (Cervonoyl ethanolamide)

3D SDF for HMDB0013627 (Cervonoyl ethanolamide)

3D-SDF for HMDB0013627 (Cervonoyl ethanolamide)

PDB for HMDB0013627 (Cervonoyl ethanolamide)

3D PDB for HMDB0013627 (Cervonoyl ethanolamide)

SMILES for HMDB0013627 (Cervonoyl ethanolamide)

INCHI for HMDB0013627 (Cervonoyl ethanolamide)

Structure for HMDB0013627 (Cervonoyl ethanolamide)

3D Structure for HMDB0013627 (Cervonoyl ethanolamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra