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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2010-05-20 10:35:33 UTC

Update Date

2022-03-07 02:51:33 UTC

HMDB ID

HMDB0013624

Secondary Accession Numbers

HMDB13624

Metabolite Identification

Common Name

Alpha-Linolenoyl ethanolamide

Description

alpha-Linolenoyl 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

HMDB0013624
     RDKit          3D
Alpha-Linolenoyl ethanolamide
 58 57  0  0  0  0  0  0  0  0999 V2000
   -8.0838    2.0406    0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9549    1.0902    0.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6600    1.7721    0.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6619    1.4219    1.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6527    0.4134    2.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8259   -0.7719    2.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0287   -1.1990    1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7920   -0.5309   -0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831   -1.4875   -1.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3569   -1.8779   -2.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9378   -1.4517   -2.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0139   -2.6148   -2.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4207   -2.2856   -2.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075   -1.5365   -1.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913   -0.1845   -0.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6852    0.3286    0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0685    0.4146   -0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9505    0.9670    0.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5004    1.2666    2.0158 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3170    1.1337    0.6097 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2596    1.6571    1.5908 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6539    1.7314    1.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1336    0.5074    0.6225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9115    2.6001    1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2663    2.7597   -0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0062    1.4397    0.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9759    0.1741    0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2059    0.7594   -0.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5176    2.5677   -0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7386    2.0333    0.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2947    0.9893    3.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7138    0.1606    2.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8706   -1.4517    3.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4620   -2.1690    1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6640   -0.4462   -0.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1773    0.4355   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2138   -1.8614   -1.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6937   -2.5753   -2.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637   -1.0674   -3.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6386   -0.6185   -1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1776   -3.1538   -1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3039   -3.4094   -2.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6971   -1.8964   -3.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -3.3143   -2.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2126   -1.4315   -1.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025   -2.1704   -0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5527    0.5609   -1.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7160   -0.1917   -0.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371   -0.4519    1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428    1.2928    0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5282   -0.5794   -0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1416    1.1146   -1.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6995    0.8862   -0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2253    1.0630    2.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9040    2.6762    1.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3413    2.1821    1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6127    2.4165    0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3932   -0.1276    0.4301 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  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 22 56  1  0
 22 57  1  0
 23 58  1  0
M  END


  Mrv0541 02271200282D          

 23 22  0  0  0  0            999 V2000
    5.3431  -15.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.0575  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7720  -15.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4865  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.2009  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.9155  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.6299  -15.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.3444  -15.5567    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.0589  -15.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.7734  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.4878  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.2023  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.9168  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.6313  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.3458  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.0602  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.7747  -15.5568    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4892  -15.1443    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.4892  -14.3192    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.2036  -15.5567    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   18.9181  -15.1442    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.6326  -15.5566    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3471  -15.1441    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0  0  0  0
  3  2  1  0  0  0  0
  4  3  2  0  0  0  0
  5  4  1  0  0  0  0
  6  5  1  0  0  0  0
  7  6  2  0  0  0  0
  8  7  1  0  0  0  0
  9  8  1  0  0  0  0
 10  9  2  0  0  0  0
 11 10  1  0  0  0  0
 12 11  1  0  0  0  0
 13 12  1  0  0  0  0
 14 13  1  0  0  0  0
 15 14  1  0  0  0  0
 16 15  1  0  0  0  0
 17 16  1  0  0  0  0
 18 17  1  0  0  0  0
 19 18  2  0  0  0  0
 20 18  1  0  0  0  0
 21 20  1  0  0  0  0
 22 21  1  0  0  0  0
 23 22  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0013624

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h3-4,6-7,9-10,22H,2,5,8,11-19H2,1H3,(H,21,23)/b4-3-,7-6-,10-9-

> <INCHI_KEY>
HBJXRRXWHSHZPU-PDBXOOCHSA-N

> <FORMULA>
C20H35NO2

> <MOLECULAR_WEIGHT>
321.4974

> <EXACT_MASS>
321.266779369

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
40.153610668212025

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
(9Z,12Z,15Z)-N-(2-hydroxyethyl)octadeca-9,12,15-trienamide

> <ALOGPS_LOGP>
5.60

> <JCHEM_LOGP>
4.786586577666667

> <ALOGPS_LOGS>
-5.51

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.473842619386154

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.469626555316182

> <JCHEM_PKA_STRONGEST_BASIC>
-0.3259293690079673

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
102.64659999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.97e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(9Z,12Z,15Z)-N-(2-hydroxyethyl)octadeca-9,12,15-trienamide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013624
     RDKit          3D
Alpha-Linolenoyl ethanolamide
 58 57  0  0  0  0  0  0  0  0999 V2000
   -8.0838    2.0406    0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9549    1.0902    0.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6600    1.7721    0.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6619    1.4219    1.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6527    0.4134    2.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8259   -0.7719    2.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0287   -1.1990    1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7920   -0.5309   -0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831   -1.4875   -1.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3569   -1.8779   -2.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9378   -1.4517   -2.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0139   -2.6148   -2.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4207   -2.2856   -2.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075   -1.5365   -1.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913   -0.1845   -0.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6852    0.3286    0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0685    0.4146   -0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9505    0.9670    0.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5004    1.2666    2.0158 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3170    1.1337    0.6097 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2596    1.6571    1.5908 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6539    1.7314    1.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1336    0.5074    0.6225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9115    2.6001    1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2663    2.7597   -0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0062    1.4397    0.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9759    0.1741    0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2059    0.7594   -0.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5176    2.5677   -0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7386    2.0333    0.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2947    0.9893    3.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7138    0.1606    2.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8706   -1.4517    3.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4620   -2.1690    1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6640   -0.4462   -0.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1773    0.4355   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2138   -1.8614   -1.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6937   -2.5753   -2.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637   -1.0674   -3.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6386   -0.6185   -1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1776   -3.1538   -1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3039   -3.4094   -2.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6971   -1.8964   -3.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -3.3143   -2.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2126   -1.4315   -1.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025   -2.1704   -0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5527    0.5609   -1.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7160   -0.1917   -0.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371   -0.4519    1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428    1.2928    0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5282   -0.5794   -0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1416    1.1146   -1.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6995    0.8862   -0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2253    1.0630    2.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9040    2.6762    1.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3413    2.1821    1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6127    2.4165    0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3932   -0.1276    0.4301 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  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 22 56  1  0
 22 57  1  0
 23 58  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       9.974 -28.269   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      11.307 -29.039   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      12.641 -28.269   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      13.975 -28.269   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      15.308 -29.039   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      16.642 -28.269   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      17.976 -28.269   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      19.310 -29.039   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      20.643 -28.269   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      21.977 -28.269   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.311 -29.039   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      24.644 -28.269   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      25.978 -29.039   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      27.312 -28.269   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      28.645 -29.039   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      29.979 -28.269   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      31.313 -29.039   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      32.647 -28.269   0.000  0.00  0.00           C+0
HETATM   19  O   UNK     0      32.647 -26.729   0.000  0.00  0.00           O+0
HETATM   20  N   UNK     0      33.980 -29.039   0.000  0.00  0.00           N+0
HETATM   21  C   UNK     0      35.314 -28.269   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      36.648 -29.039   0.000  0.00  0.00           C+0
HETATM   23  O   UNK     0      37.981 -28.269   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   20                                                  
CONECT   19   18                                                            
CONECT   20   18   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21   23                                                       
CONECT   23   22                                                            
MASTER        0    0    0    0    0    0    0    0   23    0   44    0
END

COMPND    HMDB0013624
HETATM    1  C1  UNL     1      -8.084   2.041   0.733  1.00  0.00           C  
HETATM    2  C2  UNL     1      -6.955   1.090   0.381  1.00  0.00           C  
HETATM    3  C3  UNL     1      -5.660   1.772   0.272  1.00  0.00           C  
HETATM    4  C4  UNL     1      -4.662   1.422   1.074  1.00  0.00           C  
HETATM    5  C5  UNL     1      -4.653   0.413   2.101  1.00  0.00           C  
HETATM    6  C6  UNL     1      -3.826  -0.772   2.075  1.00  0.00           C  
HETATM    7  C7  UNL     1      -3.029  -1.199   1.149  1.00  0.00           C  
HETATM    8  C8  UNL     1      -2.792  -0.531  -0.146  1.00  0.00           C  
HETATM    9  C9  UNL     1      -3.183  -1.487  -1.270  1.00  0.00           C  
HETATM   10  C10 UNL     1      -2.357  -1.878  -2.185  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.938  -1.452  -2.268  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.014  -2.615  -2.149  1.00  0.00           C  
HETATM   13  C13 UNL     1       1.421  -2.286  -2.206  1.00  0.00           C  
HETATM   14  C14 UNL     1       2.108  -1.537  -1.152  1.00  0.00           C  
HETATM   15  C15 UNL     1       1.691  -0.184  -0.739  1.00  0.00           C  
HETATM   16  C16 UNL     1       2.685   0.329   0.328  1.00  0.00           C  
HETATM   17  C17 UNL     1       4.069   0.415  -0.202  1.00  0.00           C  
HETATM   18  C18 UNL     1       4.950   0.967   0.897  1.00  0.00           C  
HETATM   19  O1  UNL     1       4.500   1.267   2.016  1.00  0.00           O  
HETATM   20  N1  UNL     1       6.317   1.134   0.610  1.00  0.00           N  
HETATM   21  C19 UNL     1       7.260   1.657   1.591  1.00  0.00           C  
HETATM   22  C20 UNL     1       8.654   1.731   1.021  1.00  0.00           C  
HETATM   23  O2  UNL     1       9.134   0.507   0.623  1.00  0.00           O  
HETATM   24  H1  UNL     1      -7.912   2.600   1.653  1.00  0.00           H  
HETATM   25  H2  UNL     1      -8.266   2.760  -0.090  1.00  0.00           H  
HETATM   26  H3  UNL     1      -9.006   1.440   0.874  1.00  0.00           H  
HETATM   27  H4  UNL     1      -6.976   0.174   0.962  1.00  0.00           H  
HETATM   28  H5  UNL     1      -7.206   0.759  -0.683  1.00  0.00           H  
HETATM   29  H6  UNL     1      -5.518   2.568  -0.470  1.00  0.00           H  
HETATM   30  H7  UNL     1      -3.739   2.033   0.963  1.00  0.00           H  
HETATM   31  H8  UNL     1      -4.295   0.989   3.058  1.00  0.00           H  
HETATM   32  H9  UNL     1      -5.714   0.161   2.458  1.00  0.00           H  
HETATM   33  H10 UNL     1      -3.871  -1.452   3.017  1.00  0.00           H  
HETATM   34  H11 UNL     1      -2.462  -2.169   1.346  1.00  0.00           H  
HETATM   35  H12 UNL     1      -1.664  -0.446  -0.234  1.00  0.00           H  
HETATM   36  H13 UNL     1      -3.177   0.436  -0.332  1.00  0.00           H  
HETATM   37  H14 UNL     1      -4.214  -1.861  -1.302  1.00  0.00           H  
HETATM   38  H15 UNL     1      -2.694  -2.575  -2.976  1.00  0.00           H  
HETATM   39  H16 UNL     1      -0.864  -1.067  -3.387  1.00  0.00           H  
HETATM   40  H17 UNL     1      -0.639  -0.618  -1.683  1.00  0.00           H  
HETATM   41  H18 UNL     1      -0.178  -3.154  -1.152  1.00  0.00           H  
HETATM   42  H19 UNL     1      -0.304  -3.409  -2.894  1.00  0.00           H  
HETATM   43  H20 UNL     1       1.697  -1.896  -3.249  1.00  0.00           H  
HETATM   44  H21 UNL     1       1.953  -3.314  -2.236  1.00  0.00           H  
HETATM   45  H22 UNL     1       3.213  -1.431  -1.464  1.00  0.00           H  
HETATM   46  H23 UNL     1       2.102  -2.170  -0.204  1.00  0.00           H  
HETATM   47  H24 UNL     1       1.553   0.561  -1.540  1.00  0.00           H  
HETATM   48  H25 UNL     1       0.716  -0.192  -0.154  1.00  0.00           H  
HETATM   49  H26 UNL     1       2.637  -0.452   1.132  1.00  0.00           H  
HETATM   50  H27 UNL     1       2.343   1.293   0.712  1.00  0.00           H  
HETATM   51  H28 UNL     1       4.528  -0.579  -0.404  1.00  0.00           H  
HETATM   52  H29 UNL     1       4.142   1.115  -1.046  1.00  0.00           H  
HETATM   53  H30 UNL     1       6.699   0.886  -0.320  1.00  0.00           H  
HETATM   54  H31 UNL     1       7.225   1.063   2.524  1.00  0.00           H  
HETATM   55  H32 UNL     1       6.904   2.676   1.841  1.00  0.00           H  
HETATM   56  H33 UNL     1       9.341   2.182   1.738  1.00  0.00           H  
HETATM   57  H34 UNL     1       8.613   2.416   0.140  1.00  0.00           H  
HETATM   58  H35 UNL     1       8.393  -0.128   0.430  1.00  0.00           H  
CONECT    1    2   24   25   26
CONECT    2    3   27   28
CONECT    3    4    4   29
CONECT    4    5   30
CONECT    5    6   31   32
CONECT    6    7    7   33
CONECT    7    8   34
CONECT    8    9   35   36
CONECT    9   10   10   37
CONECT   10   11   38
CONECT   11   12   39   40
CONECT   12   13   41   42
CONECT   13   14   43   44
CONECT   14   15   45   46
CONECT   15   16   47   48
CONECT   16   17   49   50
CONECT   17   18   51   52
CONECT   18   19   19   20
CONECT   20   21   53
CONECT   21   22   54   55
CONECT   22   23   56   57
CONECT   23   58
END

HMDB0013624
     RDKit          3D
Alpha-Linolenoyl ethanolamide
 58 57  0  0  0  0  0  0  0  0999 V2000
   -8.0838    2.0406    0.7328 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9549    1.0902    0.3806 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6600    1.7721    0.2715 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6619    1.4219    1.0737 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.6527    0.4134    2.1007 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8259   -0.7719    2.0755 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0287   -1.1990    1.1487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7920   -0.5309   -0.1457 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1831   -1.4875   -1.2697 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.3569   -1.8779   -2.1852 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9378   -1.4517   -2.2680 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0139   -2.6148   -2.1489 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.4207   -2.2856   -2.2058 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.1075   -1.5365   -1.1522 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6913   -0.1845   -0.7386 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.6852    0.3286    0.3282 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.0685    0.4146   -0.2018 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9505    0.9670    0.8973 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5004    1.2666    2.0158 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.3170    1.1337    0.6097 N   0  0  0  0  0  0  0  0  0  0  0  0
    7.2596    1.6571    1.5908 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6539    1.7314    1.0208 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1336    0.5074    0.6225 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9115    2.6001    1.6533 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.2663    2.7597   -0.0897 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.0062    1.4397    0.8738 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.9759    0.1741    0.9625 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2059    0.7594   -0.6829 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.5176    2.5677   -0.4705 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7386    2.0333    0.9634 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2947    0.9893    3.0583 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7138    0.1606    2.4579 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8706   -1.4517    3.0170 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4620   -2.1690    1.3459 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6640   -0.4462   -0.2340 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1773    0.4355   -0.3316 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2138   -1.8614   -1.3023 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6937   -2.5753   -2.9756 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8637   -1.0674   -3.3870 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6386   -0.6185   -1.6834 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1776   -3.1538   -1.1525 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3039   -3.4094   -2.8938 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.6971   -1.8964   -3.2488 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9528   -3.3143   -2.2357 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2126   -1.4315   -1.4637 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1025   -2.1704   -0.2045 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.5527    0.5609   -1.5402 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7160   -0.1917   -0.1541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6371   -0.4519    1.1321 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3428    1.2928    0.7125 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5282   -0.5794   -0.4038 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1416    1.1146   -1.0462 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.6995    0.8862   -0.3204 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.2253    1.0630    2.5241 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.9040    2.6762    1.8407 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.3413    2.1821    1.7378 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6127    2.4165    0.1402 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3932   -0.1276    0.4301 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  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  2  0
 18 20  1  0
 20 21  1  0
 21 22  1  0
 22 23  1  0
  1 24  1  0
  1 25  1  0
  1 26  1  0
  2 27  1  0
  2 28  1  0
  3 29  1  0
  4 30  1  0
  5 31  1  0
  5 32  1  0
  6 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
 10 38  1  0
 11 39  1  0
 11 40  1  0
 12 41  1  0
 12 42  1  0
 13 43  1  0
 13 44  1  0
 14 45  1  0
 14 46  1  0
 15 47  1  0
 15 48  1  0
 16 49  1  0
 16 50  1  0
 17 51  1  0
 17 52  1  0
 20 53  1  0
 21 54  1  0
 21 55  1  0
 22 56  1  0
 22 57  1  0
 23 58  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
a-Linolenoyl ethanolamide	Generator
Α-linolenoyl ethanolamide	Generator
Linoleoyl ethanolamide	ChEMBL, HMDB
alpha-LEA	HMDB
N-cis-9,12,15-Octadecatrienoylethanolamine	HMDB
ALEA compound	MeSH, HMDB
alpha-Linolenoyl ethanolamide	MeSH

Chemical Formula

C₂₀H₃₅NO₂

Average Molecular Weight

321.4974

Monoisotopic Molecular Weight

321.266779369

IUPAC Name

(9Z,12Z,15Z)-N-(2-hydroxyethyl)octadeca-9,12,15-trienamide

Traditional Name

(9Z,12Z,15Z)-N-(2-hydroxyethyl)octadeca-9,12,15-trienamide

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H35NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-20(23)21-18-19-22/h3-4,6-7,9-10,22H,2,5,8,11-19H2,1H3,(H,21,23)/b4-3-,7-6-,10-9-

InChI Key

HBJXRRXWHSHZPU-PDBXOOCHSA-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-acyl ethanolamines (endocannabinoids) (LMFA08040007 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21359215)

Cellular substructure

Source

Endogenous

Endogenous (HMDB: HMDB0013624)

Exogenous

Food

Food (HMDB: HMDB0013624)

Exogenous (HMDB: HMDB0013624)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0013624)

Role

Biological role

Energy source (HMDB: HMDB0013624)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013624)

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	0.001 g/L	ALOGPS
logP	5.6	ALOGPS
logP	4.79	ChemAxon
logS	-5.5	ALOGPS
pKa (Strongest Acidic)	15.47	ChemAxon
pKa (Strongest Basic)	-0.33	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	102.65 m³·mol⁻¹	ChemAxon
Polarizability	40.15 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	185.43	31661259
DarkChem	[M-H]-	185.058	31661259
DeepCCS	[M+H]+	186.676	30932474
DeepCCS	[M-H]-	184.318	30932474
DeepCCS	[M-2H]-	217.205	30932474
DeepCCS	[M+Na]+	192.769	30932474
AllCCS	[M+H]+	186.5	32859911
AllCCS	[M+H-H2O]+	183.7	32859911
AllCCS	[M+NH4]+	189.1	32859911
AllCCS	[M+Na]+	189.8	32859911
AllCCS	[M-H]-	185.7	32859911
AllCCS	[M+Na-2H]-	187.6	32859911
AllCCS	[M+HCOO]-	189.9	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.	7.95 minutes	32390414
Predicted by Siyang on May 30, 2022	19.9579 minutes	33406817
Predicted by Siyang using ReTip algorithm on June 8, 2022	2.11 minutes	32390414
Fem_Long = Waters ACQUITY UPLC HSS T3 C18 with Water:MeOH and 0.1% Formic Acid	2956.4 seconds	40023050
Fem_Lipids = Ascentis Express C18 with (60:40 water:ACN):(90:10 IPA:ACN) and 10mM NH4COOH + 0.1% Formic Acid	348.4 seconds	40023050
Life_Old = Waters ACQUITY UPLC BEH C18 with Water:(20:80 acetone:ACN) and 0.1% Formic Acid	198.0 seconds	40023050
Life_New = RP Waters ACQUITY UPLC HSS T3 C18 with Water:(30:70 MeOH:ACN) and 0.1% Formic Acid	237.7 seconds	40023050
RIKEN = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	610.9 seconds	40023050
Eawag_XBridgeC18 = XBridge C18 3.5u 2.1x50 mm with Water:MeOH and 0.1% Formic Acid	902.4 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	579.2 seconds	40023050
HILIC_BDD_2 = Merck SeQuant ZIC-HILIC with ACN(0.1% formic acid):water(16 mM ammonium formate)	135.5 seconds	40023050
UniToyama_Atlantis = RP Waters Atlantis T3 (2.1 x 150 mm, 5 um) with ACN:Water and 0.1% Formic Acid	1882.9 seconds	40023050
BDD_C18 = Hypersil Gold 1.9µm C18 with Water:ACN and 0.1% Formic Acid	650.3 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	1747.3 seconds	40023050
SNU_RIKEN_POS = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	656.5 seconds	40023050
RPMMFDA = Waters ACQUITY UPLC BEH C18 with Water:ACN and 0.1% Formic Acid	484.3 seconds	40023050
MTBLS87 = Merck SeQuant ZIC-pHILIC column with ACN:Water and :ammonium carbonate	330.2 seconds	40023050
KI_GIAR_zic_HILIC_pH2_7 = Merck SeQuant ZIC-HILIC with ACN:Water and 0.1% FA	383.0 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	8.7 seconds	40023050

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Alpha-Linolenoyl ethanolamide	CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)NCCO	3230.5	Standard polar	33892256
Alpha-Linolenoyl ethanolamide	CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)NCCO	2468.1	Standard non polar	33892256
Alpha-Linolenoyl ethanolamide	CC\C=C/C\C=C/C\C=C/CCCCCCCC(=O)NCCO	2679.0	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Alpha-Linolenoyl ethanolamide,1TMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C	2676.9	Semi standard non polar	33892256
Alpha-Linolenoyl ethanolamide,1TMS,isomer #2	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C	2633.0	Semi standard non polar	33892256
Alpha-Linolenoyl ethanolamide,2TMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2669.0	Semi standard non polar	33892256
Alpha-Linolenoyl ethanolamide,2TMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2731.9	Standard non polar	33892256
Alpha-Linolenoyl ethanolamide,2TMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2830.5	Standard polar	33892256
Alpha-Linolenoyl ethanolamide,1TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)NCCO[Si](C)(C)C(C)(C)C	2918.4	Semi standard non polar	33892256
Alpha-Linolenoyl ethanolamide,1TBDMS,isomer #2	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C	2852.8	Semi standard non polar	33892256
Alpha-Linolenoyl ethanolamide,2TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3158.8	Semi standard non polar	33892256
Alpha-Linolenoyl ethanolamide,2TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3087.9	Standard non polar	33892256
Alpha-Linolenoyl ethanolamide,2TBDMS,isomer #1	CC/C=C\C/C=C\C/C=C\CCCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	2897.2	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Alpha-Linolenoyl ethanolamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-01ot-3960000000-226ecbd1b70d86c5d3fe	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alpha-Linolenoyl ethanolamide GC-MS (1 TMS) - 70eV, Positive	splash10-00dj-9664000000-ad5a0bcf746ff0c9f253	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Alpha-Linolenoyl 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 - Alpha-Linolenoyl ethanolamide 10V, Positive-QTOF	splash10-00di-0009000000-1e9fdf4410a883c28949	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 20V, Positive-QTOF	splash10-0n9v-9644000000-a75202b20bb446a4cfda	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 20V, Positive-QTOF	splash10-0i7m-9644000000-f11332b1cc1fa38692fa	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 40V, Positive-QTOF	splash10-005c-9000000000-2c9af53cbc535abe705d	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 10V, Positive-QTOF	splash10-0229-6159000000-94057d6cc19761ecbccd	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 20V, Positive-QTOF	splash10-03dl-9120000000-9388d7c84f3083f8cd56	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 40V, Positive-QTOF	splash10-03di-9210000000-119fd7ae8ce73abb4f88	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 10V, Negative-QTOF	splash10-00di-0029000000-d0f5f7309a8af700f923	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 20V, Negative-QTOF	splash10-0h93-8079000000-d6f0c40f18d74d1b3ef4	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 40V, Negative-QTOF	splash10-0006-9010000000-eae31bc3ee94bdd98215	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 10V, Negative-QTOF	splash10-00di-0019000000-60eaea70585d78109afb	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 20V, Negative-QTOF	splash10-00di-5139000000-30c4ca9390a8dd057429	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 40V, Negative-QTOF	splash10-052f-9010000000-3432f4d3ac3a1fc3def9	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 10V, Positive-QTOF	splash10-0229-9127000000-65d40f108a9454c055f8	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 20V, Positive-QTOF	splash10-03dl-9000000000-8f2f6fdda3afa6267e40	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Alpha-Linolenoyl ethanolamide 40V, Positive-QTOF	splash10-01ox-9100000000-79e84dade50d1194d955	2021-09-24	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood

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	0.118 +/- 0.069 uM	Adult (>18 years old)	Both	Normal	21359215	details

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

FDB029601

KNApSAcK ID

Not Available

Chemspider ID

4446569

KEGG Compound ID

C13828

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5283449

PDB ID

Not Available

ChEBI ID

613508

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 ]

Showing metabocard for Alpha-Linolenoyl ethanolamide (HMDB0013624)

MOL for HMDB0013624 (Alpha-Linolenoyl ethanolamide)

3D MOL for HMDB0013624 (Alpha-Linolenoyl ethanolamide)

3D SDF for HMDB0013624 (Alpha-Linolenoyl ethanolamide)

3D-SDF for HMDB0013624 (Alpha-Linolenoyl ethanolamide)

PDB for HMDB0013624 (Alpha-Linolenoyl ethanolamide)

3D PDB for HMDB0013624 (Alpha-Linolenoyl ethanolamide)

SMILES for HMDB0013624 (Alpha-Linolenoyl ethanolamide)

INCHI for HMDB0013624 (Alpha-Linolenoyl ethanolamide)

Structure for HMDB0013624 (Alpha-Linolenoyl ethanolamide)

3D Structure for HMDB0013624 (Alpha-Linolenoyl ethanolamide)

Predicted Collision Cross Sections

Predicted Retention Times

Underivatized

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra