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Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2010-05-20 10:41:07 UTC

Update Date

2022-03-07 02:51:34 UTC

HMDB ID

HMDB0013625

Secondary Accession Numbers

HMDB13625

Metabolite Identification

Common Name

Dihomo-gamma-linolenoylethanolamide

Description

Dihomo-gamma-linolenoylethanolamide (DGLEA) is an 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 have been attributed to a variety of biological activities, including neurotransmission, membrane protection, and immunomodulation in animals. During abstinence, young adults with a history of alcohol binge drinking had elevated plasma levels of monounsaturated and polyunsaturatedacylethanolamides, specifically oleoylethanolamide (OEA), palmitoleoylethanolamide (POEA), arachidonoylethanolamide (AEA), and dihomo-gamma-linolenoylethanolamide (DGLEA). Changes in these lipids positively correlated with mRNA upregulation of inflammatory markers in peripheral blood mononuclear cells (PBMCs), such as toll-like receptors (TLR4), pro-inflammatory cytokines/chemokines, and cyclooxygenase-2 (PMID: 29178411 ).

Structure

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

HMDB0013625
     RDKit          3D
Dihomo-gamma-linolenoylethanolamide
 64 63  0  0  0  0  0  0  0  0999 V2000
    9.4519    1.6630    1.6376 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0299    0.4351    0.8930 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9624    0.6995   -0.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7046    1.2642    0.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6782    1.4984   -0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4482    2.0427   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2731    1.4611   -0.1257 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2127    0.1270   -0.8373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.2165   -2.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2718   -0.4859   -2.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533   -1.5648   -1.5594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1648   -2.1141   -0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5295   -2.0872    0.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7979   -1.4855    1.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7100   -2.6256    1.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0745   -2.1127    1.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6606   -1.5487    0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0635   -1.0783    0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7415   -0.4915   -0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0944   -0.0491   -0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4633   -0.2068    1.1530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9319    0.5409   -1.0073 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2740    1.0104   -0.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
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   -8.3936    3.1640   -0.1274 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    1.4500    2.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4992    1.9280    1.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
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    9.8932   -0.0325    0.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6028   -0.2944    1.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7062   -0.2529   -0.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3221    1.3833   -0.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2712    0.5333    1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8808    2.2213    1.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1488    2.3810   -1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6434    0.7112   -1.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5362    3.0249    0.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805    1.9008    0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1681   -0.3586   -0.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946   -0.4997   -0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
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   -5.1456    0.3320   -0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8677   -1.3018   -1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5861    0.6565   -1.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8408    0.1301   -0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7514    1.4152   -1.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7544    1.6953    1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1922    2.5463    0.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5413    3.3589   -1.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
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 13 14  1  0
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 25 64  1  0
M  END

 
  Mrv1652309131700092D          
 
 25 24  0  0  0  0            999 V2000
   16.5214  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3459  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8067  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0605  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.0922  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7751  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.3776  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.5996  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.6629  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   20.3142  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.9484  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.0288  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.2338  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   21.8533  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.5192  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   22.5679  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.8046  -10.7343    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   11.5192   -9.4976    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   23.2826  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   23.9971  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   24.7117  -10.7343    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   25.4263  -10.3221    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.0906  -10.3218    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.3758  -10.7342    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.6616  -10.3216    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0  0  0  0
  1  3  1  0  0  0  0
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M  END
> <DATABASE_ID>
HMDB0013625

> <DATABASE_NAME>
hmdb

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

> <INCHI_IDENTIFIER>
InChI=1S/C22H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,24H,2-5,8,11,14-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-

> <INCHI_KEY>
ULQWKETUACYZLI-QNEBEIHSSA-N

> <FORMULA>
C22H39NO2

> <MOLECULAR_WEIGHT>
349.5506

> <EXACT_MASS>
349.298079497

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
64

> <JCHEM_AVERAGE_POLARIZABILITY>
44.388786615786984

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamide

> <ALOGPS_LOGP>
6.28

> <JCHEM_LOGP>
5.675723907666667

> <ALOGPS_LOGS>
-6.17

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
16.41312374672419

> <JCHEM_PKA_STRONGEST_ACIDIC>
15.449852373793465

> <JCHEM_PKA_STRONGEST_BASIC>
-1.3086129483201976

> <JCHEM_POLAR_SURFACE_AREA>
49.33

> <JCHEM_REFRACTIVITY>
111.84859999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
17

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
2.34e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
hglea

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0013625
     RDKit          3D
Dihomo-gamma-linolenoylethanolamide
 64 63  0  0  0  0  0  0  0  0999 V2000
    9.4519    1.6630    1.6376 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0299    0.4351    0.8930 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9624    0.6995   -0.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7046    1.2642    0.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6782    1.4984   -0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4482    2.0427   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2731    1.4611   -0.1257 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2127    0.1270   -0.8373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.2165   -2.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2718   -0.4859   -2.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533   -1.5648   -1.5594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1648   -2.1141   -0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5295   -2.0872    0.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7979   -1.4855    1.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7100   -2.6256    1.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0745   -2.1127    1.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6606   -1.5487    0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0635   -1.0783    0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7415   -0.4915   -0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0944   -0.0491   -0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4633   -0.2068    1.1530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9319    0.5409   -1.0073 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2740    1.0104   -0.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1816    2.0933    0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3936    3.1640   -0.1274 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    1.4500    2.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4992    1.9280    1.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
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    4.1681   -0.3586   -0.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946   -0.4997   -0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5916    1.0015   -2.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7595   -0.1970   -3.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4442   -1.2968   -1.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4844   -2.4564   -2.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742   -2.6493   -0.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000   -2.5393    1.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6907   -0.7982    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2079   -0.9039    0.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7498   -3.4302    0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3126   -3.0699    2.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1091   -1.3190    2.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7366   -2.9234    2.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7527   -2.3221   -0.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1404   -0.6589    0.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0221   -0.3148    1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6487   -1.9678    1.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1456    0.3320   -0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8677   -1.3018   -1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5861    0.6565   -1.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8408    0.1301   -0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7514    1.4152   -1.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7544    1.6953    1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1922    2.5463    0.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5413    3.3589   -1.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 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
 15 50  1  0
 16 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  0
 19 58  1  0
 22 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  0
 24 63  1  0
 25 64  1  0
M  END

HEADER    PROTEIN                                 13-SEP-17   NONE
TITLE     NULL                                                        
COMPND    MOLECULE:                                                   
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   13-SEP-17         0                                  
HETATM    1  C   UNK     0      30.840 -20.037   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      32.379 -20.037   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.506 -19.268   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0      33.713 -19.268   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      28.172 -20.037   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      35.047 -20.037   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      26.838 -19.268   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      36.586 -20.037   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      25.504 -20.037   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      37.920 -19.268   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      24.170 -19.268   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      39.254 -20.037   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      22.836 -20.037   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      40.793 -20.037   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      21.502 -19.268   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      42.127 -19.268   0.000  0.00  0.00           C+0
HETATM   17  N   UNK     0      20.169 -20.037   0.000  0.00  0.00           N+0
HETATM   18  O   UNK     0      21.502 -17.729   0.000  0.00  0.00           O+0
HETATM   19  C   UNK     0      43.461 -20.037   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      44.795 -19.268   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      46.129 -20.037   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      47.462 -19.268   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0      18.836 -19.267   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0      17.502 -20.037   0.000  0.00  0.00           C+0
HETATM   25  O   UNK     0      16.168 -19.267   0.000  0.00  0.00           O+0
CONECT    1    2    3                                                       
CONECT    2    1    4                                                       
CONECT    3    1    5                                                       
CONECT    4    2    6                                                       
CONECT    5    3    7                                                       
CONECT    6    4    8                                                       
CONECT    7    5    9                                                       
CONECT    8    6   10                                                       
CONECT    9    7   11                                                       
CONECT   10    8   12                                                       
CONECT   11    9   13                                                       
CONECT   12   10   14                                                       
CONECT   13   11   15                                                       
CONECT   14   12   16                                                       
CONECT   15   13   17   18                                                  
CONECT   16   14   19                                                       
CONECT   17   15   23                                                       
CONECT   18   15                                                            
CONECT   19   16   20                                                       
CONECT   20   19   21                                                       
CONECT   21   20   22                                                       
CONECT   22   21                                                            
CONECT   23   17   24                                                       
CONECT   24   23   25                                                       
CONECT   25   24                                                            
MASTER        0    0    0    0    0    0    0    0   25    0   48    0
END

COMPND    HMDB0013625
HETATM    1  C1  UNL     1       9.452   1.663   1.638  1.00  0.00           C  
HETATM    2  C2  UNL     1       9.030   0.435   0.893  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.962   0.699  -0.124  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.705   1.264   0.506  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.678   1.498  -0.616  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.448   2.043  -0.057  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.273   1.461  -0.126  1.00  0.00           C  
HETATM    8  C8  UNL     1       3.213   0.127  -0.837  1.00  0.00           C  
HETATM    9  C9  UNL     1       2.329   0.217  -2.005  1.00  0.00           C  
HETATM   10  C10 UNL     1       1.272  -0.486  -2.292  1.00  0.00           C  
HETATM   11  C11 UNL     1       0.653  -1.565  -1.559  1.00  0.00           C  
HETATM   12  C12 UNL     1       1.165  -2.114  -0.332  1.00  0.00           C  
HETATM   13  C13 UNL     1       0.530  -2.087   0.816  1.00  0.00           C  
HETATM   14  C14 UNL     1      -0.798  -1.486   1.002  1.00  0.00           C  
HETATM   15  C15 UNL     1      -1.710  -2.626   1.472  1.00  0.00           C  
HETATM   16  C16 UNL     1      -3.074  -2.113   1.702  1.00  0.00           C  
HETATM   17  C17 UNL     1      -3.661  -1.549   0.434  1.00  0.00           C  
HETATM   18  C18 UNL     1      -5.064  -1.078   0.795  1.00  0.00           C  
HETATM   19  C19 UNL     1      -5.742  -0.491  -0.419  1.00  0.00           C  
HETATM   20  C20 UNL     1      -7.094  -0.049  -0.028  1.00  0.00           C  
HETATM   21  O1  UNL     1      -7.463  -0.207   1.153  1.00  0.00           O  
HETATM   22  N1  UNL     1      -7.932   0.541  -1.007  1.00  0.00           N  
HETATM   23  C21 UNL     1      -9.274   1.010  -0.727  1.00  0.00           C  
HETATM   24  C22 UNL     1      -9.182   2.093   0.325  1.00  0.00           C  
HETATM   25  O2  UNL     1      -8.394   3.164  -0.127  1.00  0.00           O  
HETATM   26  H1  UNL     1       9.568   1.450   2.741  1.00  0.00           H  
HETATM   27  H2  UNL     1      10.499   1.928   1.311  1.00  0.00           H  
HETATM   28  H3  UNL     1       8.846   2.551   1.447  1.00  0.00           H  
HETATM   29  H4  UNL     1       9.893  -0.033   0.377  1.00  0.00           H  
HETATM   30  H5  UNL     1       8.603  -0.294   1.638  1.00  0.00           H  
HETATM   31  H6  UNL     1       7.706  -0.253  -0.629  1.00  0.00           H  
HETATM   32  H7  UNL     1       8.322   1.383  -0.917  1.00  0.00           H  
HETATM   33  H8  UNL     1       6.271   0.533   1.217  1.00  0.00           H  
HETATM   34  H9  UNL     1       6.881   2.221   1.012  1.00  0.00           H  
HETATM   35  H10 UNL     1       6.149   2.381  -1.194  1.00  0.00           H  
HETATM   36  H11 UNL     1       5.643   0.711  -1.341  1.00  0.00           H  
HETATM   37  H12 UNL     1       4.536   3.025   0.461  1.00  0.00           H  
HETATM   38  H13 UNL     1       2.381   1.901   0.302  1.00  0.00           H  
HETATM   39  H14 UNL     1       4.168  -0.359  -0.972  1.00  0.00           H  
HETATM   40  H15 UNL     1       2.695  -0.500  -0.051  1.00  0.00           H  
HETATM   41  H16 UNL     1       2.592   1.002  -2.771  1.00  0.00           H  
HETATM   42  H17 UNL     1       0.760  -0.197  -3.281  1.00  0.00           H  
HETATM   43  H18 UNL     1      -0.444  -1.297  -1.415  1.00  0.00           H  
HETATM   44  H19 UNL     1       0.484  -2.456  -2.321  1.00  0.00           H  
HETATM   45  H20 UNL     1       2.174  -2.649  -0.328  1.00  0.00           H  
HETATM   46  H21 UNL     1       1.000  -2.539   1.719  1.00  0.00           H  
HETATM   47  H22 UNL     1      -0.691  -0.798   1.926  1.00  0.00           H  
HETATM   48  H23 UNL     1      -1.208  -0.904   0.202  1.00  0.00           H  
HETATM   49  H24 UNL     1      -1.750  -3.430   0.713  1.00  0.00           H  
HETATM   50  H25 UNL     1      -1.313  -3.070   2.406  1.00  0.00           H  
HETATM   51  H26 UNL     1      -3.109  -1.319   2.486  1.00  0.00           H  
HETATM   52  H27 UNL     1      -3.737  -2.923   2.082  1.00  0.00           H  
HETATM   53  H28 UNL     1      -3.753  -2.322  -0.349  1.00  0.00           H  
HETATM   54  H29 UNL     1      -3.140  -0.659   0.077  1.00  0.00           H  
HETATM   55  H30 UNL     1      -5.022  -0.315   1.588  1.00  0.00           H  
HETATM   56  H31 UNL     1      -5.649  -1.968   1.113  1.00  0.00           H  
HETATM   57  H32 UNL     1      -5.146   0.332  -0.865  1.00  0.00           H  
HETATM   58  H33 UNL     1      -5.868  -1.302  -1.195  1.00  0.00           H  
HETATM   59  H34 UNL     1      -7.586   0.657  -1.999  1.00  0.00           H  
HETATM   60  H35 UNL     1      -9.841   0.130  -0.359  1.00  0.00           H  
HETATM   61  H36 UNL     1      -9.751   1.415  -1.627  1.00  0.00           H  
HETATM   62  H37 UNL     1      -8.754   1.695   1.256  1.00  0.00           H  
HETATM   63  H38 UNL     1     -10.192   2.546   0.516  1.00  0.00           H  
HETATM   64  H39 UNL     1      -8.541   3.359  -1.083  1.00  0.00           H  
CONECT    1    2   26   27   28
CONECT    2    3   29   30
CONECT    3    4   31   32
CONECT    4    5   33   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   49   50
CONECT   16   17   51   52
CONECT   17   18   53   54
CONECT   18   19   55   56
CONECT   19   20   57   58
CONECT   20   21   21   22
CONECT   22   23   59
CONECT   23   24   60   61
CONECT   24   25   62   63
CONECT   25   64
END

HMDB0013625
     RDKit          3D
Dihomo-gamma-linolenoylethanolamide
 64 63  0  0  0  0  0  0  0  0999 V2000
    9.4519    1.6630    1.6376 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.0299    0.4351    0.8930 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9624    0.6995   -0.1244 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7046    1.2642    0.5061 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6782    1.4984   -0.6162 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4482    2.0427   -0.0573 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2731    1.4611   -0.1257 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.2127    0.1270   -0.8373 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3293    0.2165   -2.0047 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.2718   -0.4859   -2.2923 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6533   -1.5648   -1.5594 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.1648   -2.1141   -0.3321 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5295   -2.0872    0.8158 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7979   -1.4855    1.0022 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7100   -2.6256    1.4719 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0745   -2.1127    1.7021 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6606   -1.5487    0.4343 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0635   -1.0783    0.7945 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.7415   -0.4915   -0.4192 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.0944   -0.0491   -0.0283 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.4633   -0.2068    1.1530 O   0  0  0  0  0  0  0  0  0  0  0  0
   -7.9319    0.5409   -1.0073 N   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2740    1.0104   -0.7266 C   0  0  0  0  0  0  0  0  0  0  0  0
   -9.1816    2.0933    0.3254 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3936    3.1640   -0.1274 O   0  0  0  0  0  0  0  0  0  0  0  0
    9.5684    1.4500    2.7408 H   0  0  0  0  0  0  0  0  0  0  0  0
   10.4992    1.9280    1.3106 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.8461    2.5512    1.4470 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.8932   -0.0325    0.3770 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.6028   -0.2944    1.6378 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7062   -0.2529   -0.6293 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.3221    1.3833   -0.9173 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.2712    0.5333    1.2170 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.8808    2.2213    1.0116 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1488    2.3810   -1.1944 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6434    0.7112   -1.3414 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5362    3.0249    0.4610 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3805    1.9008    0.3015 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1681   -0.3586   -0.9723 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6946   -0.4997   -0.0507 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5916    1.0015   -2.7708 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7595   -0.1970   -3.2808 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4442   -1.2968   -1.4147 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.4844   -2.4564   -2.3210 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.1742   -2.6493   -0.3278 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0000   -2.5393    1.7188 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6907   -0.7982    1.9264 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2079   -0.9039    0.2015 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7498   -3.4302    0.7131 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.3126   -3.0699    2.4060 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1091   -1.3190    2.4858 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7366   -2.9234    2.0816 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7527   -2.3221   -0.3492 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1404   -0.6589    0.0767 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0221   -0.3148    1.5876 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.6487   -1.9678    1.1135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1456    0.3320   -0.8647 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8677   -1.3018   -1.1955 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.5861    0.6565   -1.9988 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.8408    0.1301   -0.3594 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.7514    1.4152   -1.6275 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7544    1.6953    1.2558 H   0  0  0  0  0  0  0  0  0  0  0  0
  -10.1922    2.5463    0.5156 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.5413    3.3589   -1.0828 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  2  0
  7  8  1  0
  8  9  1  0
  9 10  2  0
 10 11  1  0
 11 12  1  0
 12 13  2  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 17 18  1  0
 18 19  1  0
 19 20  1  0
 20 21  2  0
 20 22  1  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
  1 26  1  0
  1 27  1  0
  1 28  1  0
  2 29  1  0
  2 30  1  0
  3 31  1  0
  3 32  1  0
  4 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
 15 50  1  0
 16 51  1  0
 16 52  1  0
 17 53  1  0
 17 54  1  0
 18 55  1  0
 18 56  1  0
 19 57  1  0
 19 58  1  0
 22 59  1  0
 23 60  1  0
 23 61  1  0
 24 62  1  0
 24 63  1  0
 25 64  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
8,11,14-Eicosatrienoylethanolamide	ChEBI
Anandamide (20.3,N-6)	ChEBI
HGLEA	ChEBI
Homo-gamma-linolenylethanolamide	ChEBI
N-(8Z,11Z,14Z-Eicosatrienoyl)-ethanolamine	ChEBI
N-(8Z,11Z,14Z-Icosatrienoyl)-ethanolamide	ChEBI
Homo-g-linolenylethanolamide	Generator
Homo-γ-linolenylethanolamide	Generator
Dihomo-g-linolenoylethanolamide	Generator
Dihomo-γ-linolenoylethanolamide	Generator
Homo-gamma-linolenoyl ethanolamide	MeSH
dihomo-g-Linolenoyl ethanolamide	Generator, HMDB
dihomo-γ-linolenoyl ethanolamide	Generator, HMDB
(8Z,11Z,14Z)-N-(2-Hydroxyethyl)icosa-8,11,14-trienamide	HMDB
DGLA ea	HMDB
dihomo-gamma-Linolenoylethanol amide	HMDB
Dihomo-g-linolenoyl-ea	Generator
Dihomo-γ-linolenoyl-ea	Generator

Chemical Formula

C₂₂H₃₉NO₂

Average Molecular Weight

349.5506

Monoisotopic Molecular Weight

349.298079497

IUPAC Name

(8Z,11Z,14Z)-N-(2-hydroxyethyl)icosa-8,11,14-trienamide

Traditional Name

hglea

CAS Registry Number

150314-34-4

SMILES

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

InChI Identifier

InChI=1S/C22H39NO2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)23-20-21-24/h6-7,9-10,12-13,24H,2-5,8,11,14-21H2,1H3,(H,23,25)/b7-6-,10-9-,13-12-

InChI Key

ULQWKETUACYZLI-QNEBEIHSSA-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:34488 )
N-(long-chain-acyl)ethanolamine (CHEBI:34488 )
N-acyl ethanolamides (endocannabinoids) (C13828 )
N-acyl ethanolamines (endocannabinoids) (LMFA08040011 )

Ontology

Not Available

Non-excretory biofluid

Blood (PMID: 21359215)

Blood (HMDB: HMDB0013625)

Cellular substructure

Extracellular (HMDB: HMDB0013625)
Membrane (HMDB: HMDB0013625)

Source

Endogenous

Endogenous (HMDB: HMDB0013625)

Exogenous

Food

Food (HMDB: HMDB0013625)

Process

Naturally occurring process

Biological process

Cellular process

Cell signaling (HMDB: HMDB0013625)

Role

Biological role

Energy source (HMDB: HMDB0013625)

Industrial application

Manufacturing industry

Material processing agent

Fluid processing agent

Surfactant

Surfactant (HMDB: HMDB0013625)

Emulsifier (HMDB: HMDB0013625)

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	0.00023 g/L	ALOGPS
logP	6.28	ALOGPS
logP	5.68	ChemAxon
logS	-6.2	ALOGPS
pKa (Strongest Acidic)	15.45	ChemAxon
pKa (Strongest Basic)	-1.3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	49.33 Å²	ChemAxon
Rotatable Bond Count	17	ChemAxon
Refractivity	111.85 m³·mol⁻¹	ChemAxon
Polarizability	44.39 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]+	196.924	31661259
DarkChem	[M-H]-	196.788	31661259
DeepCCS	[M+H]+	197.639	30932474
DeepCCS	[M-H]-	195.281	30932474
DeepCCS	[M-2H]-	228.168	30932474
DeepCCS	[M+Na]+	203.732	30932474
AllCCS	[M+H]+	195.2	32859911
AllCCS	[M+H-H2O]+	192.7	32859911
AllCCS	[M+NH4]+	197.6	32859911
AllCCS	[M+Na]+	198.3	32859911
AllCCS	[M-H]-	193.3	32859911
AllCCS	[M+Na-2H]-	195.7	32859911
AllCCS	[M+HCOO]-	198.5	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Dihomo-gamma-linolenoylethanolamide	CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)NCCO	3260.3	Standard polar	33892256
Dihomo-gamma-linolenoylethanolamide	CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)NCCO	2634.1	Standard non polar	33892256
Dihomo-gamma-linolenoylethanolamide	CCCCC\C=C/C\C=C/C\C=C/CCCCCCC(=O)NCCO	2862.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihomo-gamma-linolenoylethanolamide,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)NCCO[Si](C)(C)C	2879.5	Semi standard non polar	33892256
Dihomo-gamma-linolenoylethanolamide,1TMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)N(CCO)[Si](C)(C)C	2826.4	Semi standard non polar	33892256
Dihomo-gamma-linolenoylethanolamide,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2867.1	Semi standard non polar	33892256
Dihomo-gamma-linolenoylethanolamide,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2914.9	Standard non polar	33892256
Dihomo-gamma-linolenoylethanolamide,2TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)N(CCO[Si](C)(C)C)[Si](C)(C)C	2948.7	Standard polar	33892256
Dihomo-gamma-linolenoylethanolamide,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)NCCO[Si](C)(C)C(C)(C)C	3117.9	Semi standard non polar	33892256
Dihomo-gamma-linolenoylethanolamide,1TBDMS,isomer #2	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)N(CCO)[Si](C)(C)C(C)(C)C	3059.8	Semi standard non polar	33892256
Dihomo-gamma-linolenoylethanolamide,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3356.2	Semi standard non polar	33892256
Dihomo-gamma-linolenoylethanolamide,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3247.7	Standard non polar	33892256
Dihomo-gamma-linolenoylethanolamide,2TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)N(CCO[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C	3011.1	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Dihomo-gamma-linolenoylethanolamide GC-MS (Non-derivatized) - 70eV, Positive	splash10-029g-8983000000-42e4744911acb250a34f	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihomo-gamma-linolenoylethanolamide GC-MS (1 TMS) - 70eV, Positive	splash10-00y0-9573200000-a8db30d9ff9f0147625e	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihomo-gamma-linolenoylethanolamide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihomo-gamma-linolenoylethanolamide 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 - Dihomo-gamma-linolenoylethanolamide 10V, Positive-QTOF	splash10-0w29-5149000000-90d7161272eec6776994	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 20V, Positive-QTOF	splash10-03dl-9121000000-76079fc33c97f5136a62	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 40V, Positive-QTOF	splash10-03dl-9230000000-71d39c754ceca5b22f18	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 10V, Negative-QTOF	splash10-0002-0009000000-70187c5620a575618c1e	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 20V, Negative-QTOF	splash10-01pk-5019000000-7d063e287364f13a7e93	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 40V, Negative-QTOF	splash10-0006-9010000000-756ebbaf8f5db95a9d3c	2017-09-01	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 10V, Negative-QTOF	splash10-0002-0009000000-25e88f7ed1f5fc19f31f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 20V, Negative-QTOF	splash10-0002-5129000000-b4eff9f1d3f5b681b725	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 40V, Negative-QTOF	splash10-052f-9010000000-3b5498e873ffa2327ed5	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 10V, Positive-QTOF	splash10-0w29-9228000000-3de5ffd9870259f4c489	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 20V, Positive-QTOF	splash10-03dl-9000000000-55cab8b86efb0346a9ef	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenoylethanolamide 40V, Positive-QTOF	splash10-01ox-9100000000-50506e85794f343a8424	2021-09-23	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	1.01 +/- 0.48 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

FDB029602

KNApSAcK ID

Not Available

Chemspider ID

4445443

KEGG Compound ID

C13828

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

5282272

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 ]
Anton M, Rodriguez-Gonzalez A, Rodriguez-Rojo IC, Pastor A, Correas A, Serrano A, Ballesta A, Alen F, Gomez de Heras R, de la Torre R, Rodriguez de Fonseca F, Orio L: Increased plasma oleoylethanolamide and palmitoleoylethanolamide levels correlate with inflammatory changes in alcohol binge drinkers: the case of HMGB1 in women. Addict Biol. 2018 Nov;23(6):1242-1250. doi: 10.1111/adb.12580. Epub 2017 Nov 27. [PubMed:29178411 ]

Showing metabocard for Dihomo-gamma-linolenoylethanolamide (HMDB0013625)

MOL for HMDB0013625 (Dihomo-gamma-linolenoylethanolamide)

3D MOL for HMDB0013625 (Dihomo-gamma-linolenoylethanolamide)

3D SDF for HMDB0013625 (Dihomo-gamma-linolenoylethanolamide)

3D-SDF for HMDB0013625 (Dihomo-gamma-linolenoylethanolamide)

PDB for HMDB0013625 (Dihomo-gamma-linolenoylethanolamide)

3D PDB for HMDB0013625 (Dihomo-gamma-linolenoylethanolamide)

SMILES for HMDB0013625 (Dihomo-gamma-linolenoylethanolamide)

INCHI for HMDB0013625 (Dihomo-gamma-linolenoylethanolamide)

Structure for HMDB0013625 (Dihomo-gamma-linolenoylethanolamide)

3D Structure for HMDB0013625 (Dihomo-gamma-linolenoylethanolamide)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra