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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2011-07-11 14:50:38 UTC

Update Date

2022-03-07 02:51:34 UTC

HMDB ID

HMDB0013658

Secondary Accession Numbers

HMDB13658

Metabolite Identification

Common Name

Docosahexaenoyl Ethanolamide

Description

Docosahexaenoic Acid (DHA) is an essential fatty acid and the most abundant ω-3 fatty acid in neural tissues, especially in the retina and brain. Docosahexaenoyl ethanolamide (DHEA) is the ethanolamine amide of DHA that has been detected in both brain and retina at concentrations similar to those for arachidonoyl ethanolamide (AEA).1,2 A 9.5 fold increase of DHEA was observed in brain lipid extracts from piglets fed a diet supplemented with DHA compared to a control diet without DHA.3 DHEA binds to the rat brain CB1 receptor with a Ki of 324 nM, which is approximately 10-fold higher than the Ki for AEA.4 DHEA inhibits shaker-related voltage-gated potassium channels in brain slightly better than AEA, with an IC50 of 1.5 ¬µM.

Structure

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

  Mrv0541 02271200292D          

 27 26  0  0  0  0            999 V2000
    5.1298  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8443  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5587  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2733  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9877  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7022  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4167  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1312  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8456  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5601  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2746  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9891  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7036  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4180  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1325  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8470  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5614  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2759  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9904  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7049  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4194  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1338  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8483  -10.4095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1338  -11.6471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5628  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2772  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9917  -10.8221    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

HMDB0013658
     RDKit          3D
Docosahexaenoyl Ethanolamide
 64 63  0  0  0  0  0  0  0  0999 V2000
  -10.6599    0.5430    0.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6674    0.1716   -0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8456   -0.9562    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5474   -0.8706    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7850    0.3760   -0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0678    0.8499    1.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7754    1.0245    1.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8672    0.7717    0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0444    1.9624   -0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7639    1.9567   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8795    0.9202    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801   -0.3777    0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9940   -1.5531    0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1686   -1.7483   -0.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9910   -2.5741   -0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -2.2125   -0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6601   -0.8792   -1.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5025   -1.1000   -2.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7413   -0.6488   -2.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4286    0.0957   -1.4928 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6720   -0.6367   -0.9902 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3529    0.1620    0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8007    1.2488    0.3850 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5110   -0.3443    0.6815 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3013    0.2467    1.7051 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8830    1.5493    1.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9424    2.4877    0.9466 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5416    0.9968    0.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2032    1.3105    1.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8932   -0.3282    1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1637    1.0953   -0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3143   -0.1531   -1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3686   -1.9119    0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9442   -1.7191    0.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0435    0.0785   -0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3927    1.1671   -0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7233    1.0654    1.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4080    1.3807    2.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5648    0.7588   -0.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311   -0.1964    0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5936    2.8744   -0.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752    2.9340   -0.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0709    0.7312   -0.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580    1.3335    1.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9030   -0.4525    1.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3745   -2.4654    0.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8031   -2.4563   -1.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0142   -0.8894   -1.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7618   -3.5674   -0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0182   -2.9269   -0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8178   -0.2043   -1.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2307   -0.4007   -0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0587   -1.6521   -3.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2561   -0.8848   -3.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8757    1.0123   -2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8317    0.5447   -0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4005   -0.7683   -1.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4199   -1.6102   -0.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8535   -1.2933    0.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1162   -0.4151    2.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6280    0.4491    2.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5380    1.9904    2.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5739    1.3228    0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0974    2.7852    0.0201 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
 24 59  1  0
 25 60  1  0
 25 61  1  0
 26 62  1  0
 26 63  1  0
 27 64  1  0
M  END

  Mrv0541 02271200292D          

 27 26  0  0  0  0            999 V2000
    5.1298  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.8443  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.5587  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.2733  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9877  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.7022  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4167  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.1312  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8456  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5601  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2746  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9891  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7036  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4180  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1325  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8470  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.5614  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.2759  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.9904  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7049  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.4194  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.1338  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.8483  -10.4095    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   20.1338  -11.6471    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   21.5628  -10.8221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.2772  -10.4095    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.9917  -10.8221    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>
HMDB0013658

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C24H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(27)25-22-23-26/h3-4,6-7,9-10,12-13,15-16,18-19,26H,2,5,8,11,14,17,20-23H2,1H3,(H,25,27)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-

> <INCHI_KEY>
GEEHOLRSGZPBSM-KUBAVDMBSA-N

> <FORMULA>
C24H37NO2

> <MOLECULAR_WEIGHT>
371.5561

> <EXACT_MASS>
371.282429433

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
44.14247117027844

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

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

> <ALOGPS_LOGP>
6.17

> <JCHEM_LOGP>
5.479096267666667

> <ALOGPS_LOGS>
-5.80

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.412357019959163

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.448971538182775

> <JCHEM_PKA_STRONGEST_BASIC>
-0.48192683597059827

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
124.40039999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
16

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
5.90e-04 g/l

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

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013658
     RDKit          3D
Docosahexaenoyl Ethanolamide
 64 63  0  0  0  0  0  0  0  0999 V2000
  -10.6599    0.5430    0.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6674    0.1716   -0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8456   -0.9562    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5474   -0.8706    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7850    0.3760   -0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0678    0.8499    1.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7754    1.0245    1.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8672    0.7717    0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0444    1.9624   -0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7639    1.9567   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8795    0.9202    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801   -0.3777    0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9940   -1.5531    0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1686   -1.7483   -0.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9910   -2.5741   -0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -2.2125   -0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6601   -0.8792   -1.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5025   -1.1000   -2.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7413   -0.6488   -2.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4286    0.0957   -1.4928 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6720   -0.6367   -0.9902 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3529    0.1620    0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8007    1.2488    0.3850 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5110   -0.3443    0.6815 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3013    0.2467    1.7051 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8830    1.5493    1.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9424    2.4877    0.9466 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5416    0.9968    0.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2032    1.3105    1.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8932   -0.3282    1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1637    1.0953   -0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3143   -0.1531   -1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3686   -1.9119    0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9442   -1.7191    0.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0435    0.0785   -0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3927    1.1671   -0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7233    1.0654    1.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4080    1.3807    2.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5648    0.7588   -0.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311   -0.1964    0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5936    2.8744   -0.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752    2.9340   -0.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0709    0.7312   -0.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580    1.3335    1.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9030   -0.4525    1.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3745   -2.4654    0.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8031   -2.4563   -1.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0142   -0.8894   -1.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7618   -3.5674   -0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0182   -2.9269   -0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8178   -0.2043   -1.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2307   -0.4007   -0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0587   -1.6521   -3.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2561   -0.8848   -3.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8757    1.0123   -2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8317    0.5447   -0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4005   -0.7683   -1.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4199   -1.6102   -0.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8535   -1.2933    0.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1162   -0.4151    2.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6280    0.4491    2.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5380    1.9904    2.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5739    1.3228    0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0974    2.7852    0.0201 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
 24 59  1  0
 25 60  1  0
 25 61  1  0
 26 62  1  0
 26 63  1  0
 27 64  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       9.576 -19.431   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      10.909 -20.201   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.243 -19.431   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.577 -19.431   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      14.910 -20.201   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.244 -19.431   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.578 -19.431   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      18.912 -20.201   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.245 -19.431   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.579 -19.431   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      22.913 -20.201   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.246 -19.431   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.580 -19.431   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      26.914 -20.201   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.247 -19.431   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.581 -19.431   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      30.915 -20.201   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.248 -19.431   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      33.582 -19.431   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      34.916 -20.201   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      36.250 -19.431   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      37.583 -20.201   0.000  0.00  0.00           C+0
HETATM   23  N   UNK     0      38.917 -19.431   0.000  0.00  0.00           N+0
HETATM   24  O   UNK     0      37.583 -21.741   0.000  0.00  0.00           O+0
HETATM   25  C   UNK     0      40.251 -20.201   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      41.584 -19.431   0.000  0.00  0.00           C+0
HETATM   27  O   UNK     0      42.918 -20.201   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    HMDB0013658
HETATM    1  C1  UNL     1     -10.660   0.543   0.825  1.00  0.00           C  
HETATM    2  C2  UNL     1      -9.667   0.172  -0.303  1.00  0.00           C  
HETATM    3  C3  UNL     1      -8.846  -0.956   0.173  1.00  0.00           C  
HETATM    4  C4  UNL     1      -7.547  -0.871   0.268  1.00  0.00           C  
HETATM    5  C5  UNL     1      -6.785   0.376  -0.098  1.00  0.00           C  
HETATM    6  C6  UNL     1      -6.068   0.850   1.111  1.00  0.00           C  
HETATM    7  C7  UNL     1      -4.775   1.025   1.202  1.00  0.00           C  
HETATM    8  C8  UNL     1      -3.867   0.772   0.084  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.044   1.962  -0.258  1.00  0.00           C  
HETATM   10  C10 UNL     1      -1.764   1.957  -0.162  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.880   0.920   0.262  1.00  0.00           C  
HETATM   12  C12 UNL     1      -1.280  -0.378   0.733  1.00  0.00           C  
HETATM   13  C13 UNL     1      -0.994  -1.553   0.228  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.169  -1.748  -0.972  1.00  0.00           C  
HETATM   15  C15 UNL     1       0.991  -2.574  -0.594  1.00  0.00           C  
HETATM   16  C16 UNL     1       2.237  -2.212  -0.720  1.00  0.00           C  
HETATM   17  C17 UNL     1       2.660  -0.879  -1.281  1.00  0.00           C  
HETATM   18  C18 UNL     1       3.502  -1.100  -2.486  1.00  0.00           C  
HETATM   19  C19 UNL     1       4.741  -0.649  -2.545  1.00  0.00           C  
HETATM   20  C20 UNL     1       5.429   0.096  -1.493  1.00  0.00           C  
HETATM   21  C21 UNL     1       6.672  -0.637  -0.990  1.00  0.00           C  
HETATM   22  C22 UNL     1       7.353   0.162   0.095  1.00  0.00           C  
HETATM   23  O1  UNL     1       6.801   1.249   0.385  1.00  0.00           O  
HETATM   24  N1  UNL     1       8.511  -0.344   0.682  1.00  0.00           N  
HETATM   25  C23 UNL     1       9.301   0.247   1.705  1.00  0.00           C  
HETATM   26  C24 UNL     1       9.883   1.549   1.278  1.00  0.00           C  
HETATM   27  O2  UNL     1       8.942   2.488   0.947  1.00  0.00           O  
HETATM   28  H1  UNL     1     -11.542   0.997   0.329  1.00  0.00           H  
HETATM   29  H2  UNL     1     -10.203   1.311   1.487  1.00  0.00           H  
HETATM   30  H3  UNL     1     -10.893  -0.328   1.437  1.00  0.00           H  
HETATM   31  H4  UNL     1      -9.164   1.095  -0.553  1.00  0.00           H  
HETATM   32  H5  UNL     1     -10.314  -0.153  -1.187  1.00  0.00           H  
HETATM   33  H6  UNL     1      -9.369  -1.912   0.459  1.00  0.00           H  
HETATM   34  H7  UNL     1      -6.944  -1.719   0.626  1.00  0.00           H  
HETATM   35  H8  UNL     1      -6.044   0.078  -0.896  1.00  0.00           H  
HETATM   36  H9  UNL     1      -7.393   1.167  -0.536  1.00  0.00           H  
HETATM   37  H10 UNL     1      -6.723   1.065   2.000  1.00  0.00           H  
HETATM   38  H11 UNL     1      -4.408   1.381   2.192  1.00  0.00           H  
HETATM   39  H12 UNL     1      -4.565   0.759  -0.864  1.00  0.00           H  
HETATM   40  H13 UNL     1      -3.431  -0.196   0.022  1.00  0.00           H  
HETATM   41  H14 UNL     1      -3.594   2.874  -0.603  1.00  0.00           H  
HETATM   42  H15 UNL     1      -1.275   2.934  -0.463  1.00  0.00           H  
HETATM   43  H16 UNL     1      -0.071   0.731  -0.537  1.00  0.00           H  
HETATM   44  H17 UNL     1      -0.158   1.333   1.098  1.00  0.00           H  
HETATM   45  H18 UNL     1      -1.903  -0.452   1.678  1.00  0.00           H  
HETATM   46  H19 UNL     1      -1.375  -2.465   0.701  1.00  0.00           H  
HETATM   47  H20 UNL     1      -0.803  -2.456  -1.631  1.00  0.00           H  
HETATM   48  H21 UNL     1       0.014  -0.889  -1.595  1.00  0.00           H  
HETATM   49  H22 UNL     1       0.762  -3.567  -0.176  1.00  0.00           H  
HETATM   50  H23 UNL     1       3.018  -2.927  -0.396  1.00  0.00           H  
HETATM   51  H24 UNL     1       1.818  -0.204  -1.485  1.00  0.00           H  
HETATM   52  H25 UNL     1       3.231  -0.401  -0.463  1.00  0.00           H  
HETATM   53  H26 UNL     1       3.059  -1.652  -3.326  1.00  0.00           H  
HETATM   54  H27 UNL     1       5.256  -0.885  -3.503  1.00  0.00           H  
HETATM   55  H28 UNL     1       5.876   1.012  -2.028  1.00  0.00           H  
HETATM   56  H29 UNL     1       4.832   0.545  -0.703  1.00  0.00           H  
HETATM   57  H30 UNL     1       7.400  -0.768  -1.815  1.00  0.00           H  
HETATM   58  H31 UNL     1       6.420  -1.610  -0.523  1.00  0.00           H  
HETATM   59  H32 UNL     1       8.854  -1.293   0.323  1.00  0.00           H  
HETATM   60  H33 UNL     1      10.116  -0.415   2.070  1.00  0.00           H  
HETATM   61  H34 UNL     1       8.628   0.449   2.583  1.00  0.00           H  
HETATM   62  H35 UNL     1      10.538   1.990   2.071  1.00  0.00           H  
HETATM   63  H36 UNL     1      10.574   1.323   0.410  1.00  0.00           H  
HETATM   64  H37 UNL     1       9.097   2.785   0.020  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   59
CONECT   25   26   60   61
CONECT   26   27   62   63
CONECT   27   64
END

HMDB0013658
     RDKit          3D
Docosahexaenoyl Ethanolamide
 64 63  0  0  0  0  0  0  0  0999 V2000
  -10.6599    0.5430    0.8248 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.6674    0.1716   -0.3026 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.8456   -0.9562    0.1732 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5474   -0.8706    0.2683 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7850    0.3760   -0.0976 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0678    0.8499    1.1111 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7754    1.0245    1.2020 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8672    0.7717    0.0841 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0444    1.9624   -0.2581 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7639    1.9567   -0.1618 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8795    0.9202    0.2617 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2801   -0.3777    0.7329 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9940   -1.5531    0.2279 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1686   -1.7483   -0.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9910   -2.5741   -0.5941 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.2375   -2.2125   -0.7201 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6601   -0.8792   -1.2807 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.5025   -1.1000   -2.4857 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7413   -0.6488   -2.5450 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.4286    0.0957   -1.4928 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6720   -0.6367   -0.9902 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3529    0.1620    0.0946 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.8007    1.2488    0.3850 O   0  0  0  0  0  0  0  0  0  0  0  0
    8.5110   -0.3443    0.6815 N   0  0  0  0  0  0  0  0  0  0  0  0
    9.3013    0.2467    1.7051 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8830    1.5493    1.2783 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9424    2.4877    0.9466 O   0  0  0  0  0  0  0  0  0  0  0  0
  -11.5416    0.9968    0.3289 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.2032    1.3105    1.4866 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.8932   -0.3282    1.4372 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1637    1.0953   -0.5534 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.3143   -0.1531   -1.1868 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.3686   -1.9119    0.4588 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9442   -1.7191    0.6257 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0435    0.0785   -0.8962 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.3927    1.1671   -0.5363 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.7233    1.0654    1.9998 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.4080    1.3807    2.1919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5648    0.7588   -0.8638 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4311   -0.1964    0.0222 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.5936    2.8744   -0.6027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2752    2.9340   -0.4635 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0709    0.7312   -0.5368 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1580    1.3335    1.0982 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9030   -0.4525    1.6776 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3745   -2.4654    0.7006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8031   -2.4563   -1.6307 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0142   -0.8894   -1.5950 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7618   -3.5674   -0.1763 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0182   -2.9269   -0.3962 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8178   -0.2043   -1.4847 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2307   -0.4007   -0.4630 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0587   -1.6521   -3.3263 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.2561   -0.8848   -3.5027 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8757    1.0123   -2.0281 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.8317    0.5447   -0.7030 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.4005   -0.7683   -1.8153 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.4199   -1.6102   -0.5227 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8535   -1.2933    0.3232 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.1162   -0.4151    2.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6280    0.4491    2.5831 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5380    1.9904    2.0713 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.5739    1.3228    0.4098 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.0974    2.7852    0.0201 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
 24 59  1  0
 25 60  1  0
 25 61  1  0
 26 62  1  0
 26 63  1  0
 27 64  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Anandamide (22:6, N-3)	ChEBI
N-(4Z,7Z,10Z,13Z,16Z,19Z)-Docosahexaenoyl ethanolamine	ChEBI
N-(4Z,7Z,10Z,13Z,16Z,19Z-Docosahexaenoyl)-ethanolamine	ChEBI
N-cis-4,7,10,13,16,19-Docosahexanoylethanolamine	ChEBI
DHEA	HMDB
N-Docosahexaenoylethanolamine	HMDB
Synaptamide	HMDB

Chemical Formula

C₂₄H₃₇NO₂

Average Molecular Weight

371.5561

Monoisotopic Molecular Weight

371.282429433

IUPAC Name

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

Traditional Name

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

CAS Registry Number

162758-94-3

SMILES

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

InChI Identifier

InChI=1S/C24H37NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-24(27)25-22-23-26/h3-4,6-7,9-10,12-13,15-16,18-19,26H,2,5,8,11,14,17,20-23H2,1H3,(H,25,27)/b4-3-,7-6-,10-9-,13-12-,16-15-,19-18-

InChI Key

GEEHOLRSGZPBSM-KUBAVDMBSA-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:85252 )
N-(long-chain-acyl)ethanolamine (CHEBI:85252 )
endocannabinoid (CHEBI:85252 )
N-acyl ethanolamines (endocannabinoids) (LMFA08040009 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0013658)

Exogenous

Food

Food (HMDB: HMDB0013658)

Exogenous (HMDB: HMDB0013658)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0013658)

Role

Biological role

Energy source (HMDB: HMDB0013658)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013658)

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	0.00059 g/L	ALOGPS
logP	6.17	ALOGPS
logP	5.48	ChemAxon
logS	-5.8	ALOGPS
pKa (Strongest Acidic)	15.45	ChemAxon
pKa (Strongest Basic)	-0.48	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	124.4 m³·mol⁻¹	ChemAxon
Polarizability	44.14 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	202.676	31661259
DarkChem	[M-H]-	199.309	31661259
DeepCCS	[M+H]+	192.734	30932474
DeepCCS	[M-H]-	190.376	30932474
DeepCCS	[M-2H]-	224.508	30932474
DeepCCS	[M+Na]+	199.735	30932474
AllCCS	[M+H]+	199.9	32859911
AllCCS	[M+H-H2O]+	197.4	32859911
AllCCS	[M+NH4]+	202.3	32859911
AllCCS	[M+Na]+	202.9	32859911
AllCCS	[M-H]-	196.9	32859911
AllCCS	[M+Na-2H]-	199.4	32859911
AllCCS	[M+HCOO]-	202.3	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Docosahexaenoyl Ethanolamide	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)NCCO	3774.8	Standard polar	33892256
Docosahexaenoyl Ethanolamide	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)NCCO	2693.2	Standard non polar	33892256
Docosahexaenoyl Ethanolamide	CC\C=C/C\C=C/C\C=C/C\C=C/C\C=C/C\C=C/CCC(=O)NCCO	3038.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Docosahexaenoyl Ethanolamide,1TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)NCCO[Si](C)(C)C	3061.3	Semi standard non polar	33892256
Docosahexaenoyl Ethanolamide,1TMS,isomer #2	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)N(CCO)[Si](C)(C)C	2975.2	Semi standard non polar	33892256
Docosahexaenoyl Ethanolamide,2TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	3020.9	Semi standard non polar	33892256
Docosahexaenoyl Ethanolamide,2TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	3082.9	Standard non polar	33892256
Docosahexaenoyl Ethanolamide,2TMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2862.7	Standard polar	33892256
Docosahexaenoyl Ethanolamide,1TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)NCCO[Si](C)(C)C(C)(C)C	3302.6	Semi standard non polar	33892256
Docosahexaenoyl Ethanolamide,1TBDMS,isomer #2	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)N(CCO)[Si](C)(C)C(C)(C)C	3255.3	Semi standard non polar	33892256
Docosahexaenoyl Ethanolamide,2TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3524.8	Semi standard non polar	33892256
Docosahexaenoyl Ethanolamide,2TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3455.1	Standard non polar	33892256
Docosahexaenoyl Ethanolamide,2TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\C/C=C\C/C=C\C/C=C\CCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2936.6	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Docosahexaenoyl Ethanolamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-01pn-5689000000-9b4cf8006243e895d7fd	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Docosahexaenoyl Ethanolamide GC-MS (1 TMS) - 70eV, Positive	splash10-0229-9252500000-4110b89f2ab73a72a776	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Docosahexaenoyl Ethanolamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Docosahexaenoyl 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
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 40V, Positive-QTOF	splash10-004l-9300000000-755a232bf686c9d61dfb	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 20V, Positive-QTOF	splash10-00di-5963000000-a14e32bf4384a5ec6ab4	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 10V, Positive-QTOF	splash10-00di-0139000000-cbd16ee9ab14480e2258	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 40V, Positive-QTOF	splash10-004l-9300000000-0f4562ef3f5b1dc54898	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 10V, Positive-QTOF	splash10-03k9-4019000000-b2b242bda3ce38e12aef	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 20V, Positive-QTOF	splash10-03dl-9122000000-94df13a6db155fe1a268	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 40V, Positive-QTOF	splash10-03di-9131000000-501bb548fdce0075c37c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 10V, Negative-QTOF	splash10-00di-0009000000-741bef7b3dd5fb7030a0	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 20V, Negative-QTOF	splash10-0h93-5009000000-b38e328eb1895d2389d4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 40V, Negative-QTOF	splash10-0006-9011000000-bf3dda5617b0256af534	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 10V, Positive-QTOF	splash10-0229-8219000000-ba8b3f4b94a4307def3a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 20V, Positive-QTOF	splash10-03dl-9000000000-ba6d821d8c695f4fc847	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 40V, Positive-QTOF	splash10-03di-9200000000-395426e731c4a00622ed	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 10V, Negative-QTOF	splash10-00di-0009000000-ae9aa8ca13d13c461e97	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 20V, Negative-QTOF	splash10-00di-5119000000-2c2db26f6fcb310f1f26	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Docosahexaenoyl Ethanolamide 40V, Negative-QTOF	splash10-0596-9002000000-8d2b9949220ff1f090c5	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

FDB029628

KNApSAcK ID

Not Available

Chemspider ID

4446571

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283451

PDB ID

Not Available

ChEBI ID

85252

Food Biomarker Ontology

Not Available

VMH ID

DOCOHXETH

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Not Available

Showing metabocard for Docosahexaenoyl Ethanolamide (HMDB0013658)

MOL for HMDB0013658 (Docosahexaenoyl Ethanolamide)

3D MOL for HMDB0013658 (Docosahexaenoyl Ethanolamide)

3D SDF for HMDB0013658 (Docosahexaenoyl Ethanolamide)

3D-SDF for HMDB0013658 (Docosahexaenoyl Ethanolamide)

PDB for HMDB0013658 (Docosahexaenoyl Ethanolamide)

3D PDB for HMDB0013658 (Docosahexaenoyl Ethanolamide)

SMILES for HMDB0013658 (Docosahexaenoyl Ethanolamide)

INCHI for HMDB0013658 (Docosahexaenoyl Ethanolamide)

Structure for HMDB0013658 (Docosahexaenoyl Ethanolamide)

3D Structure for HMDB0013658 (Docosahexaenoyl Ethanolamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra