MiMeDB: Showing metabocard for Dihomo-gamma-linolenic acid (MMDBc0000595)

Record Information

Version

1.0

Status

Detected and Quantified

Creation Date

2020-12-10 18:50:43 UTC

Update Date

2022-08-31 06:10:09 UTC

Metabolite ID

MMDBc0000595

Metabolite Identification

Common Name

Dihomo-gamma-linolenic acid

Description

Dihomo-gamma-linolenic acid, also known as (Z,Z,Z)-8,11,14-icosatrienoate or 8,11,14-eicosatrienoic acid, belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms. Dihomo-gamma-linolenic acid is a very hydrophobic molecule, practically insoluble (in water), and relatively neutral.

Structure

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

HMDB0002925
     RDKit          3D
Dihomo-gamma-linolenic acid
 56 55  0  0  0  0  0  0  0  0999 V2000
    8.1825   -0.1150   -0.8607 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1846    1.2025   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5650    1.2863    1.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1648    1.1967    1.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3034    0.0900    1.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9400   -0.0661   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6468    0.0329   -0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5367    0.3002    0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5999   -0.8357    0.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3323   -0.8180   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3443    0.4460   -0.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8605    0.2458   -1.8098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1311    0.3441   -2.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1521    0.6450   -1.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0927   -0.5826   -1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2259   -0.3897   -0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0550   -1.6228   -0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2351   -1.8185    0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3671   -0.8763    0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1008    0.4719    1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1121    0.7378    1.8375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9823    1.5307    0.8475 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7970   -0.0550   -1.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2490   -0.4897   -0.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6841   -0.9247   -0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7323    1.9398   -0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2715    1.5479   -0.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1828    0.5471    1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9434    2.2813    1.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6285    2.1554    1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9839    1.3766    2.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8997   -0.9063    1.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4133   -0.0004    1.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6077   -0.2748   -1.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4286   -0.0991   -1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0863    1.2595   -0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8827    0.5882    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123   -1.8308    0.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2534   -1.7630    0.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1454    0.5816    0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461    1.2866   -0.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1284    0.0109   -2.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5217    0.1941   -3.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7640    1.5439   -1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8952    0.7808   -0.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5522   -0.6312   -2.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4877   -1.4633   -0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8206   -0.1737    0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8233    0.4840   -0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3532   -2.4907    0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4167   -1.7539   -1.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8687   -1.9323    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6087   -2.8820    0.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7605   -0.7933   -0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2609   -1.2516    1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2859    1.7328   -0.0922 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
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 22 56  1  0
M  END

LMFA01030158
  Mrv1652305052022592D          

 22 21  0  0  0  0            999 V2000
   18.4557    5.5058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   19.1659    5.0956    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   18.4557    6.1625    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   17.7402    5.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.0244    5.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   16.3085    5.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.5927    5.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.8769    5.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.1610    5.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.4452    5.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.7293    5.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.0135    5.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2977    5.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   10.5819    5.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.8660    5.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.1502    5.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4344    5.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.7185    5.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.0028    5.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2869    5.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.5711    5.0956    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8553    5.5057    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  4  5  1  0  0  0  0
  5  6  1  0  0  0  0
  6  7  1  0  0  0  0
  7  8  1  0  0  0  0
  8  9  1  0  0  0  0
  9 10  1  0  0  0  0
 10 11  2  0  0  0  0
 11 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 16 17  2  0  0  0  0
 17 18  1  0  0  0  0
 18 19  1  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
M  END
> <DATABASE_ID>
MMDBc0000595

> <DATABASE_NAME>
MIME

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

> <INCHI_IDENTIFIER>
InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-

> <INCHI_KEY>
HOBAELRKJCKHQD-QNEBEIHSSA-N

> <FORMULA>
C20H34O2

> <MOLECULAR_WEIGHT>
306.4828

> <EXACT_MASS>
306.255880332

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_ATOM_COUNT>
56

> <JCHEM_AVERAGE_POLARIZABILITY>
39.01409630611928

> <JCHEM_BIOAVAILABILITY>
0

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(8Z,11Z,14Z)-icosa-8,11,14-trienoic acid

> <ALOGPS_LOGP>
7.24

> <JCHEM_LOGP>
6.9490924676666666

> <ALOGPS_LOGS>
-6.60

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
0

> <JCHEM_PHYSIOLOGICAL_CHARGE>
-1

> <JCHEM_PKA_STRONGEST_ACIDIC>
4.885823686047827

> <JCHEM_POLAR_SURFACE_AREA>
37.3

> <JCHEM_REFRACTIVITY>
98.83739999999999

> <JCHEM_ROTATABLE_BOND_COUNT>
15

> <JCHEM_RULE_OF_FIVE>
0

> <ALOGPS_SOLUBILITY>
7.71e-05 g/l

> <JCHEM_TRADITIONAL_IUPAC>
dihomo-gamma-linolenic acid

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0002925
     RDKit          3D
Dihomo-gamma-linolenic acid
 56 55  0  0  0  0  0  0  0  0999 V2000
    8.1825   -0.1150   -0.8607 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1846    1.2025   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5650    1.2863    1.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1648    1.1967    1.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3034    0.0900    1.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9400   -0.0661   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6468    0.0329   -0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5367    0.3002    0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5999   -0.8357    0.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3323   -0.8180   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3443    0.4460   -0.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8605    0.2458   -1.8098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1311    0.3441   -2.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1521    0.6450   -1.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0927   -0.5826   -1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2259   -0.3897   -0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0550   -1.6228   -0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2351   -1.8185    0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3671   -0.8763    0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1008    0.4719    1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1121    0.7378    1.8375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9823    1.5307    0.8475 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7970   -0.0550   -1.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2490   -0.4897   -0.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6841   -0.9247   -0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7323    1.9398   -0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2715    1.5479   -0.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1828    0.5471    1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9434    2.2813    1.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6285    2.1554    1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9839    1.3766    2.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8997   -0.9063    1.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4133   -0.0004    1.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6077   -0.2748   -1.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4286   -0.0991   -1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0863    1.2595   -0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8827    0.5882    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123   -1.8308    0.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2534   -1.7630    0.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1454    0.5816    0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461    1.2866   -0.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1284    0.0109   -2.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5217    0.1941   -3.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7640    1.5439   -1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8952    0.7808   -0.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5522   -0.6312   -2.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4877   -1.4633   -0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8206   -0.1737    0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8233    0.4840   -0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3532   -2.4907    0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4167   -1.7539   -1.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8687   -1.9323    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6087   -2.8820    0.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7605   -0.7933   -0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2609   -1.2516    1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2859    1.7328   -0.0922 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
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 22 56  1  0
M  END

HEADER    PROTEIN                                 05-MAY-20   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: LMFA01030158                                      
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   05-MAY-20         0                                  
HETATM    1  C   UNK     0      34.451  10.277   0.000  0.00  0.00           C+0
HETATM    2  O   UNK     0      35.776   9.512   0.000  0.00  0.00           O+0
HETATM    3  O   UNK     0      34.451  11.503   0.000  0.00  0.00           O+0
HETATM    4  C   UNK     0      33.115   9.512   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      31.779  10.277   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0      30.443   9.512   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      29.106  10.277   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0      27.770   9.512   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0      26.434  10.277   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.098   9.512   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      23.761   9.512   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      22.425  10.277   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      21.089   9.512   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      19.753   9.512   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      18.417  10.277   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      17.080   9.512   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      15.744   9.512   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0      14.408  10.277   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      13.072   9.512   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0      11.736  10.277   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      10.399   9.512   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0       9.063  10.277   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1                                                            
CONECT    3    1                                                            
CONECT    4    1    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                                                            
MASTER        0    0    0    0    0    0    0    0   22    0   42    0
END

COMPND    HMDB0002925
HETATM    1  C1  UNL     1       8.182  -0.115  -0.861  1.00  0.00           C  
HETATM    2  C2  UNL     1       8.185   1.202  -0.171  1.00  0.00           C  
HETATM    3  C3  UNL     1       7.565   1.286   1.146  1.00  0.00           C  
HETATM    4  C4  UNL     1       6.165   1.197   1.449  1.00  0.00           C  
HETATM    5  C5  UNL     1       5.303   0.090   1.092  1.00  0.00           C  
HETATM    6  C6  UNL     1       4.940  -0.066  -0.307  1.00  0.00           C  
HETATM    7  C7  UNL     1       3.647   0.033  -0.666  1.00  0.00           C  
HETATM    8  C8  UNL     1       2.537   0.300   0.274  1.00  0.00           C  
HETATM    9  C9  UNL     1       1.600  -0.836   0.265  1.00  0.00           C  
HETATM   10  C10 UNL     1       0.332  -0.818  -0.036  1.00  0.00           C  
HETATM   11  C11 UNL     1      -0.344   0.446  -0.427  1.00  0.00           C  
HETATM   12  C12 UNL     1      -0.860   0.246  -1.810  1.00  0.00           C  
HETATM   13  C13 UNL     1      -2.131   0.344  -2.047  1.00  0.00           C  
HETATM   14  C14 UNL     1      -3.152   0.645  -1.049  1.00  0.00           C  
HETATM   15  C15 UNL     1      -4.093  -0.583  -1.070  1.00  0.00           C  
HETATM   16  C16 UNL     1      -5.226  -0.390  -0.047  1.00  0.00           C  
HETATM   17  C17 UNL     1      -6.055  -1.623  -0.155  1.00  0.00           C  
HETATM   18  C18 UNL     1      -7.235  -1.819   0.686  1.00  0.00           C  
HETATM   19  C19 UNL     1      -8.367  -0.876   0.633  1.00  0.00           C  
HETATM   20  C20 UNL     1      -8.101   0.472   1.142  1.00  0.00           C  
HETATM   21  O1  UNL     1      -7.112   0.738   1.837  1.00  0.00           O  
HETATM   22  O2  UNL     1      -8.982   1.531   0.847  1.00  0.00           O  
HETATM   23  H1  UNL     1       7.797  -0.055  -1.891  1.00  0.00           H  
HETATM   24  H2  UNL     1       9.249  -0.490  -0.962  1.00  0.00           H  
HETATM   25  H3  UNL     1       7.684  -0.925  -0.268  1.00  0.00           H  
HETATM   26  H4  UNL     1       7.732   1.940  -0.908  1.00  0.00           H  
HETATM   27  H5  UNL     1       9.272   1.548  -0.157  1.00  0.00           H  
HETATM   28  H6  UNL     1       8.183   0.547   1.808  1.00  0.00           H  
HETATM   29  H7  UNL     1       7.943   2.281   1.635  1.00  0.00           H  
HETATM   30  H8  UNL     1       5.629   2.155   1.051  1.00  0.00           H  
HETATM   31  H9  UNL     1       5.984   1.377   2.591  1.00  0.00           H  
HETATM   32  H10 UNL     1       5.900  -0.906   1.325  1.00  0.00           H  
HETATM   33  H11 UNL     1       4.413  -0.000   1.752  1.00  0.00           H  
HETATM   34  H12 UNL     1       5.608  -0.275  -1.150  1.00  0.00           H  
HETATM   35  H13 UNL     1       3.429  -0.099  -1.747  1.00  0.00           H  
HETATM   36  H14 UNL     1       2.086   1.259  -0.138  1.00  0.00           H  
HETATM   37  H15 UNL     1       2.883   0.588   1.254  1.00  0.00           H  
HETATM   38  H16 UNL     1       2.012  -1.831   0.548  1.00  0.00           H  
HETATM   39  H17 UNL     1      -0.253  -1.763   0.001  1.00  0.00           H  
HETATM   40  H18 UNL     1      -1.145   0.582   0.334  1.00  0.00           H  
HETATM   41  H19 UNL     1       0.346   1.287  -0.370  1.00  0.00           H  
HETATM   42  H20 UNL     1      -0.128   0.011  -2.626  1.00  0.00           H  
HETATM   43  H21 UNL     1      -2.522   0.194  -3.083  1.00  0.00           H  
HETATM   44  H22 UNL     1      -3.764   1.544  -1.367  1.00  0.00           H  
HETATM   45  H23 UNL     1      -2.895   0.781  -0.022  1.00  0.00           H  
HETATM   46  H24 UNL     1      -4.552  -0.631  -2.061  1.00  0.00           H  
HETATM   47  H25 UNL     1      -3.488  -1.463  -0.835  1.00  0.00           H  
HETATM   48  H26 UNL     1      -4.821  -0.174   0.937  1.00  0.00           H  
HETATM   49  H27 UNL     1      -5.823   0.484  -0.402  1.00  0.00           H  
HETATM   50  H28 UNL     1      -5.353  -2.491   0.027  1.00  0.00           H  
HETATM   51  H29 UNL     1      -6.417  -1.754  -1.238  1.00  0.00           H  
HETATM   52  H30 UNL     1      -6.869  -1.932   1.761  1.00  0.00           H  
HETATM   53  H31 UNL     1      -7.609  -2.882   0.472  1.00  0.00           H  
HETATM   54  H32 UNL     1      -8.760  -0.793  -0.418  1.00  0.00           H  
HETATM   55  H33 UNL     1      -9.261  -1.252   1.213  1.00  0.00           H  
HETATM   56  H34 UNL     1      -9.286   1.733  -0.092  1.00  0.00           H  
CONECT    1    2   23   24   25
CONECT    2    3   26   27
CONECT    3    4   28   29
CONECT    4    5   30   31
CONECT    5    6   32   33
CONECT    6    7    7   34
CONECT    7    8   35
CONECT    8    9   36   37
CONECT    9   10   10   38
CONECT   10   11   39
CONECT   11   12   40   41
CONECT   12   13   13   42
CONECT   13   14   43
CONECT   14   15   44   45
CONECT   15   16   46   47
CONECT   16   17   48   49
CONECT   17   18   50   51
CONECT   18   19   52   53
CONECT   19   20   54   55
CONECT   20   21   21   22
CONECT   22   56
END

HMDB0002925
     RDKit          3D
Dihomo-gamma-linolenic acid
 56 55  0  0  0  0  0  0  0  0999 V2000
    8.1825   -0.1150   -0.8607 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.1846    1.2025   -0.1713 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5650    1.2863    1.1461 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.1648    1.1967    1.4491 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3034    0.0900    1.0922 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9400   -0.0661   -0.3069 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6468    0.0329   -0.6657 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.5367    0.3002    0.2741 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5999   -0.8357    0.2652 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3323   -0.8180   -0.0359 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.3443    0.4460   -0.4269 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8605    0.2458   -1.8098 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1311    0.3441   -2.0469 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1521    0.6450   -1.0487 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0927   -0.5826   -1.0695 C   0  0  0  0  0  0  0  0  0  0  0  0
   -5.2259   -0.3897   -0.0467 C   0  0  0  0  0  0  0  0  0  0  0  0
   -6.0550   -1.6228   -0.1546 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.2351   -1.8185    0.6860 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.3671   -0.8763    0.6331 C   0  0  0  0  0  0  0  0  0  0  0  0
   -8.1008    0.4719    1.1416 C   0  0  0  0  0  0  0  0  0  0  0  0
   -7.1121    0.7378    1.8375 O   0  0  0  0  0  0  0  0  0  0  0  0
   -8.9823    1.5307    0.8475 O   0  0  0  0  0  0  0  0  0  0  0  0
    7.7970   -0.0550   -1.8910 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2490   -0.4897   -0.9621 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.6841   -0.9247   -0.2682 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.7323    1.9398   -0.9077 H   0  0  0  0  0  0  0  0  0  0  0  0
    9.2715    1.5479   -0.1572 H   0  0  0  0  0  0  0  0  0  0  0  0
    8.1828    0.5471    1.8079 H   0  0  0  0  0  0  0  0  0  0  0  0
    7.9434    2.2813    1.6353 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6285    2.1554    1.0511 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.9839    1.3766    2.5915 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.8997   -0.9063    1.3246 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.4133   -0.0004    1.7524 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6077   -0.2748   -1.1495 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4286   -0.0991   -1.7470 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0863    1.2595   -0.1377 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8827    0.5882    1.2540 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.0123   -1.8308    0.5476 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2534   -1.7630    0.0006 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1454    0.5816    0.3341 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3461    1.2866   -0.3702 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1284    0.0109   -2.6260 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.5217    0.1941   -3.0827 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.7640    1.5439   -1.3672 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8952    0.7808   -0.0223 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.5522   -0.6312   -2.0615 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4877   -1.4633   -0.8352 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.8206   -0.1737    0.9370 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.8233    0.4840   -0.4025 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.3532   -2.4907    0.0273 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.4167   -1.7539   -1.2376 H   0  0  0  0  0  0  0  0  0  0  0  0
   -6.8687   -1.9323    1.7607 H   0  0  0  0  0  0  0  0  0  0  0  0
   -7.6087   -2.8820    0.4716 H   0  0  0  0  0  0  0  0  0  0  0  0
   -8.7605   -0.7933   -0.4183 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2609   -1.2516    1.2135 H   0  0  0  0  0  0  0  0  0  0  0  0
   -9.2859    1.7328   -0.0922 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
  1 23  1  0
  1 24  1  0
  1 25  1  0
  2 26  1  0
  2 27  1  0
  3 28  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  5 33  1  0
  6 34  1  0
  7 35  1  0
  8 36  1  0
  8 37  1  0
  9 38  1  0
 10 39  1  0
 11 40  1  0
 11 41  1  0
 12 42  1  0
 13 43  1  0
 14 44  1  0
 14 45  1  0
 15 46  1  0
 15 47  1  0
 16 48  1  0
 16 49  1  0
 17 50  1  0
 17 51  1  0
 18 52  1  0
 18 53  1  0
 19 54  1  0
 19 55  1  0
 22 56  1  0
M  END

Synonyms

Value	Source
(8Z,11Z,14Z)-Icosatrienoic acid	ChEBI
(Z,Z,Z)-8,11,14-Eicosatrienoic acid	ChEBI
(Z,Z,Z)-8,11,14-Icosatrienoate	ChEBI
(Z,Z,Z)-8,11,14-Icosatrienoic acid	ChEBI
20:3, N-6,9,12 all-cis	ChEBI
8,11,14-Eicosatrienoic acid	ChEBI
8C,11C,14C-Eicosatrienoic acid	ChEBI
8C,11C,14C-Eicosatriensaeure	ChEBI
8Z,11Z,14Z-Eicosatrienoic acid	ChEBI
all-cis-8,11,14-Eicosatrienoic acid	ChEBI
all-cis-8,11,14-Icosatrienoic acid	ChEBI
all-cis-Eicosa-8,11,14-trienoic acid	ChEBI
all-cis-Eicosa-8,11,14-triensaeure	ChEBI
C20:3, N-6,9,12 all-cis	ChEBI
cis,cis,cis-8,11,14-Eicosatrienoic acid	ChEBI
DGLA	ChEBI
Eicosa-8Z,11Z,14Z-trienoic acid	ChEBI
gamma-Homolinolenic acid	ChEBI
Homo-gamma-linolenic acid	ChEBI
Homo-gamma-linolensaeure	ChEBI
(Z,Z,Z)-8,11,14-Eicosatrienoate	Kegg
8,11,14-Eicosatrienoate	Kegg
8,11,14-Icosatrienoate	Kegg
(8Z,11Z,14Z)-Icosa-8,11,14-trienoic acid	Kegg
(8Z,11Z,14Z)-Icosatrienoate	Generator
8C,11C,14C-Eicosatrienoate	Generator
8Z,11Z,14Z-Eicosatrienoate	Generator
all-cis-8,11,14-Eicosatrienoate	Generator
all-cis-8,11,14-Icosatrienoate	Generator
all-cis-Eicosa-8,11,14-trienoate	Generator
cis,cis,cis-8,11,14-Eicosatrienoate	Generator
Eicosa-8Z,11Z,14Z-trienoate	Generator
g-Homolinolenate	Generator
g-Homolinolenic acid	Generator
gamma-Homolinolenate	Generator
Γ-homolinolenate	Generator
Γ-homolinolenic acid	Generator
Homo-g-linolenate	Generator
Homo-g-linolenic acid	Generator
Homo-gamma-linolenate	Generator
Homo-γ-linolenate	Generator
Homo-γ-linolenic acid	Generator
Homo-g-linolensaeure	Generator
Homo-γ-linolensaeure	Generator
8,11,14-Icosatrienoic acid	Generator
(8Z,11Z,14Z)-Icosa-8,11,14-trienoate	Generator
Dihomo-g-linolenate	Generator
Dihomo-g-linolenic acid	Generator
Dihomo-gamma-linolenate	Generator
Dihomo-γ-linolenate	Generator
Dihomo-γ-linolenic acid	Generator
Dihomogammalinolenic acid	HMDB
Dihomo gamma linolenic acid	HMDB
Homo-gamma linolenic acid	HMDB
Homo gamma linolenic acid	HMDB
Linolenic acid, homo-gamma	HMDB
8,11,14 Eicosatrienoic acid	HMDB
(Z,Z,Z)-Icosatri-8,11,14-enoate	HMDB
(Z,Z,Z)-Icosatri-8,11,14-enoic acid	HMDB
8,11,14-all-cis-Eicosatrienoate	HMDB
8,11,14-all-cis-Eicosatrienoic acid	HMDB
Bishomo-gamma-linolenate	HMDB
Bishomo-gamma-linolenic acid	HMDB
cis-8,11,14-Eicosatrienoate	HMDB
cis-8,11,14-Eicosatrienoic acid	HMDB
cis-8,cis-11,cis-14-Eicosatrienoate	HMDB
cis-8,cis-11,cis-14-Eicosatrienoic acid	HMDB
Eicosatrienoate	HMDB
Eicosatrienoic acid	HMDB
Acid, dihomo-gamma-linolenic	HMDB
DHLA	HMDB
Acid, dihomogammalinolenic	HMDB
Acid, homo-gamma linolenic	HMDB
Dihomolinolenate	HMDB
Dihomolinolenic acid	HMDB
FA(20:3(8Z,11Z,14Z))	HMDB
Dihomo-linolenate	HMDB
Dihomo-linolenic acid	HMDB
FA(20:3n6)	HMDB
dihomo-gamma-Linolenic acid	ChEBI

Molecular Formula

C₂₀H₃₄O₂

Average Mass

306.4828

Monoisotopic Mass

306.255880332

IUPAC Name

(8Z,11Z,14Z)-icosa-8,11,14-trienoic acid

Traditional Name

dihomo-gamma-linolenic acid

CAS Registry Number

Not Available

SMILES

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

InChI Identifier

InChI=1S/C20H34O2/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20(21)22/h6-7,9-10,12-13H,2-5,8,11,14-19H2,1H3,(H,21,22)/b7-6-,10-9-,13-12-

InChI Key

HOBAELRKJCKHQD-QNEBEIHSSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as long-chain fatty acids. These are fatty acids with an aliphatic tail that contains between 13 and 21 carbon atoms.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Fatty Acyls

Sub Class

Fatty acids and conjugates

Direct Parent

Long-chain fatty acids

Alternative Parents

Substituents

Long-chain fatty acid
Unsaturated fatty acid
Straight chain fatty acid
Monocarboxylic acid or derivatives
Carboxylic acid
Carboxylic acid derivative
Organic oxygen compound
Organic oxide
Hydrocarbon derivative
Organooxygen compound
Carbonyl group
Aliphatic acyclic compound

Molecular Framework

Aliphatic acyclic compounds

External Descriptors

long-chain fatty acid (CHEBI:53486 )
icosatrienoic acid (CHEBI:53486 )
Polyunsaturated fatty acids (C03242 )
Unsaturated fatty acids (LMFA01030158 )

Functional Ontology

Not Available

Physical Properties

State

Expected Solid

Predicted Properties

Property	Value	Source
Water Solubility	7.7e-05 g/L	ALOGPS
logP	7.24	ALOGPS
logP	6.95	ChemAxon
logS	-6.6	ALOGPS
pKa (Strongest Acidic)	4.89	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	15	ChemAxon
Refractivity	98.84 m³·mol⁻¹	ChemAxon
Polarizability	39.01 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

Spectra

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Chromatographic Retention Times and Retention Indices

Retention Times

Not Available

Retention Indices

Not Available

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biospecimen Locations

Adipose Tissue
Blood
Epidermis
Feces
Placenta

Tissue Locations

Adipose Tissue
Epidermis
Placenta

Associated OMIM IDs

114500 (Colorectal cancer)
610247 (Eosinophilic esophagitis)

Human Proteins and Enzymes

Protein ID	Protein Name	Protein Type	Uniprot ID	Species
MMDBp0192196	Bile acid-CoA:amino acid N-acyltransferase	Enzyme	Q14032	Homo_sapiens
MMDBp0192655	Cytosolic acyl coenzyme A thioester hydrolase	Enzyme	O00154	Homo_sapiens
MMDBp0192656	Acyl-coenzyme A thioesterase 2, mitochondrial	Enzyme	P49753	Homo_sapiens
MMDBp0192657	Acyl-coenzyme A thioesterase 4	Enzyme	Q8N9L9	Homo_sapiens
MMDBp0192658	Acyl-coenzyme A thioesterase 8	Enzyme	O14734	Homo_sapiens
MMDBp0196516	Acyl-coenzyme A thioesterase 1	Enzyme	Q86TX2	Homo_sapiens

Human Pathways

Pathways

Name	SMPDB/PathBank

Microbial Pathways

Pathways

Not Available

Metabolic Reactions

Reactions

This table shows at most 20 reactions. For the full list of associated reactions:

See All Associated Reactions

Reaction ID	Precursor	Product	Enzyme	Reaction Type	Data Source	Reference

Health Effects and Bioactivity

Health Outcome/Bioactivity	Metabolite Response/Effect	Evidence Type	Host and Biospecimen	Data Source	Reference
Isovaleric acidemia		Association	Human Blood	HMDB	27329611

Microbial Sources

Superkingdom/Kingdom	Phylum	Total species	Hosts and Body Sites	Microbial Links
Bacteria	Verrucomicrobia	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Firmicutes	11	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen
Bacteria	Actinobacteria	1	Human vaginal fluid	Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1		Indirect association between microbiota composition and metabolites measured in host biospecimen
Archaea	Euryarchaeota	1	Human feces	Indirect association between microbiota composition and metabolites measured in host biospecimen

Exposure Sources

Other Exposures

Source Type	Data Source	Reference

Host Biospecimen and Location

Host and Biospecimen	Status	Mean	Std	Age	Sex	Health Condition	Data Source	Reference
Human Feces	Detected but not Quantified						HMDB
Human	Detected and Quantified	84.8	30.8	Adult (>18 years old)	Not Specified	Isovaleric acidemia	HMDB	27329611
Human	Detected and Quantified	0.420	0.207	Adult (>18 years old)	Both	Normal	HMDB	18953024
Human	Detected and Quantified	0.420	0.207	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human	Detected and Quantified	0.54	0.005	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human	Detected and Quantified	0.542	0.005	Adult (>18 years old)	Both	Normal	HMDB	20671299
Human	Detected and Quantified	118.408	39.774	Adult (>18 years old)	Female	Normal	HMDB	9368807
Human	Detected and Quantified	3.61	2.1	Adult (>18 years old)	Both	Normal	HMDB	21359215
Human Adipose Tissue	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597
Human Epidermis	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597
Human Placenta	Detected but not Quantified			Not Specified	Not Specified	Normal	HMDB	34986597
Human Feces	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	27543620
Human Feces	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	25037050
Human Feces	Detected but not Quantified			Adult (>18 years old)	Both	Normal	HMDB	29808030

External Links

HMDB ID

HMDB0002925

DrugBank ID

DB00154

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB023082

KNApSAcK ID

Not Available

Chemspider ID

4444199

KEGG Compound ID

C03242

BioCyc ID

Not Available

BiGG ID

41475

Wikipedia Link

Dihomo-γ-linolenic acid

METLIN ID

259

PubChem Compound

5280581

PDB ID

Not Available

ChEBI ID

53486

Food Biomarker Ontology

Not Available

CMMC Knowledgebase

Not Available

General References

Abraham RD, Riemersma RA, Elton RA, Macintyre C, Oliver MF: Effects of safflower oil and evening primrose oil in men with a low dihomo-gamma-linolenic level. Atherosclerosis. 1990 Apr;81(3):199-208. doi: 10.1016/0021-9150(90)90067-s. [PubMed:2112389 ]
Melnik BC, Plewig G: Is the origin of atopy linked to deficient conversion of omega-6-fatty acids to prostaglandin E1? J Am Acad Dermatol. 1989 Sep;21(3 Pt 1):557-63. doi: 10.1016/s0190-9622(89)70226-7. [PubMed:2550526 ]
Hamilton RM, Gillespie CT, Cook HW: Relationships between levels of essential fatty acids and zinc in plasma of cystic fibrosis patients. Lipids. 1981 May;16(5):374-6. doi: 10.1007/BF02534966. [PubMed:6789026 ]
Emken EA, Adlof RO, Duval SM, Nelson GJ: Influence of dietary arachidonic acid on metabolism in vivo of 8cis,11cis,14-eicosatrienoic acid in humans. Lipids. 1997 Apr;32(4):441-8. doi: 10.1007/s11745-997-0058-4. [PubMed:9113634 ]
Thijs C, Houwelingen A, Poorterman I, Mordant A, van den Brandt P: Essential fatty acids in breast milk of atopic mothers: comparison with non-atopic mothers, and effect of borage oil supplementation. Eur J Clin Nutr. 2000 Mar;54(3):234-8. doi: 10.1038/sj.ejcn.1600926. [PubMed:10713746 ]
Du L, Yermalitsky V, Hachey DL, Jagadeesh SG, Falck JR, Keeney DS: A biosynthetic pathway generating 12-hydroxy-5,8,14-eicosatrienoic acid from arachidonic acid is active in mouse skin microsomes. J Pharmacol Exp Ther. 2006 Jan;316(1):371-9. doi: 10.1124/jpet.105.093922. Epub 2005 Sep 16. [PubMed:16169934 ]
Elshenawy S, Pinney SE, Stuart T, Doulias PT, Zura G, Parry S, Elovitz MA, Bennett MJ, Bansal A, Strauss JF 3rd, Ischiropoulos H, Simmons RA: The Metabolomic Signature of the Placenta in Spontaneous Preterm Birth. Int J Mol Sci. 2020 Feb 4;21(3). pii: ijms21031043. doi: 10.3390/ijms21031043. [PubMed:32033212 ]

Showing metabocard for Dihomo-gamma-linolenic acid (MMDBc0000595)

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