NP-MRD: Showing NP-Card for 8,11,14-Eicosatrienoic acid (NP0001142)

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Record Information

Version

2.0

Created at

2006-05-22 15:12:20 UTC

Updated at

2024-09-17 15:44:08 UTC

NP-MRD ID

NP0001142

Secondary Accession Numbers

None

Natural Product Identification

Common Name

8,11,14-Eicosatrienoic acid

Description

8,11,14-Eicosatrienoic acid is a 20-carbon-chain omega-6 fatty acid, unsaturated at positions 8, 11, and 14. It differs from arachidonic acid (5,8,11,14-eicosatetraenoic acid) only at position 5. 8,11,14-Eicosatrienoic acid is also known as Dihomo-gamma-linolenic acid (DGLA). In physiological literature, it is given the name 20:3(N-6). DGLA is the elongation product of the 18 carbon gamma-linolenic acid (GLA). DGLA can be converted into prostaglandin E1 (PGE1). PGE1 inhibits platelet aggregation and also exerts a vasodilatory effect. DGLA competes with arachadonic acid for COX and lipoxygenase, inhibiting the production of arachadonic acid's eicosanoids.

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>
NP0001142

> <DATABASE_NAME>
NP-MRD

> <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

View in JSmol View NMR Assignments

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

Chemical Formula

C₂₀H₃₄O₂

Average Mass

306.4828 Da

Monoisotopic Mass

306.25588 Da

IUPAC Name

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

Traditional Name

dihomo-gamma-linolenic acid

CAS Registry Number

1783-84-2

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

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Spectrum Type	Description	Depositor ID	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 25 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 252 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 50 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 75 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 101 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 126 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 151 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 176 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 201 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 226 MHz, D₂O, predicted)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Ailuropoda melanoleuca	LOTUS Database	35616633
Eurhynchium striatum	LOTUS Database	35616633
Homo sapiens	LOTUS Database	35616633
Myuroclada maximowiczii	LOTUS Database	35616633
Sargassum pallidum	LOTUS Database	35616633

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 )

Physical Properties

State

Liquid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.0024 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	Not Available	Not Available

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

External Links

HMDB ID

HMDB0002925

DrugBank ID

DB00154

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB112210

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

Good Scents ID

rw1230471

References

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. [PubMed:2112389 ]
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. Epub 2005 Sep 16. [PubMed:16169934 ]
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. [PubMed:6789026 ]
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. [PubMed:10713746 ]
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. [PubMed:9113634 ]
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. [PubMed:2550526 ]

Showing NP-Card for 8,11,14-Eicosatrienoic acid (NP0001142)

MOL for NP0001142 (8,11,14-Eicosatrienoic acid)

3D MOL for NP0001142 (8,11,14-Eicosatrienoic acid)

3D SDF for NP0001142 (8,11,14-Eicosatrienoic acid)

3D-SDF for NP0001142 (8,11,14-Eicosatrienoic acid)

PDB for NP0001142 (8,11,14-Eicosatrienoic acid)

3D PDB for NP0001142 (8,11,14-Eicosatrienoic acid)

SMILES for NP0001142 (8,11,14-Eicosatrienoic acid)

INCHI for NP0001142 (8,11,14-Eicosatrienoic acid)

Structure for NP0001142 (8,11,14-Eicosatrienoic acid)

3D Structure for NP0001142 (8,11,14-Eicosatrienoic acid)