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Identification Taxonomy Ontology Physical properties Spectra Biological properties Concentrations Links References enzymes (6) Show 6 proteins XML

Record Information

Version

5.0

Status

Detected and Quantified

Creation Date

2006-05-22 15:12:20 UTC

Update Date

2022-03-07 02:49:17 UTC

HMDB ID

HMDB0002925

Secondary Accession Numbers

HMDB0006735
HMDB02925
HMDB06735

Metabolite Identification

Common Name

Dihomo-gamma-linolenic 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>
HMDB0002925

> <DATABASE_NAME>
hmdb

> <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 Stereo Labels

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 Molecular Weight

306.4828

Monoisotopic Molecular Weight

306.255880332

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

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 )

Ontology

Not Available

Adipose Tissue (HMDB: HMDB0002925)

Epithelium

Epidermis (HMDB: HMDB0002925)

Organ

Placenta (HMDB: HMDB0002925)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 18953024)
Saliva (PMID: 31026179)

Excreta

Biofluid or Excreta

Feces (PMID: 27275383)

Cellular substructure

Greylag goose (FooDB: FOOD00368)
Guinea hen (FooDB: FOOD00373)
Ostrich (FooDB: FOOD00422)
Velvet duck (FooDB: FOOD00427)
Pheasant (FooDB: FOOD00430)
Squab (FooDB: FOOD00481)
Turkey (FooDB: FOOD00494)
Quail (FooDB: FOOD00541)
Anatidae (FooDB: FOOD00576)
Rock ptarmigan (FooDB: FOOD00597)
Columbidae (Dove, Pigeon) (FooDB: FOOD00610)
Chicken (FooDB: FOOD00329)
Mallard duck (FooDB: FOOD00353)
Emu (FooDB: FOOD00360)

Equine

Horse (FooDB: FOOD00378)

Lagomorph

Ovis

Sheep (Mutton, Lamb) (FooDB: FOOD00473)

Bovine

Venison

Deer (FooDB: FOOD00524)
Mule deer (FooDB: FOOD00348)
Elk (FooDB: FOOD00359)

Caprae

Domestic goat (FooDB: FOOD00529)

Swine

Domestic pig (FooDB: FOOD00536)
Wild boar (FooDB: FOOD00307)

Process

Naturally occurring process

Biological process

Biochemical pathway

Metabolic pathway

Alpha Linolenic Acid and Linoleic Acid Metabolism (PathBank: SMP0000018)

Role

Industrial application

Pharmaceutical industry

Biomarker

Isovaleric acidemia (MarkerDB: MDB00030006)

Physical Properties

State

Liquid

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

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M-H]-	Not Available	182.643	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001849

Predicted Molecular 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

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	186.908	31661259
DarkChem	[M-H]-	188.28	31661259
DeepCCS	[M+H]+	185.157	30932474
DeepCCS	[M-H]-	182.799	30932474
DeepCCS	[M-2H]-	215.685	30932474
DeepCCS	[M+Na]+	191.251	30932474
AllCCS	[M+H]+	184.6	32859911
AllCCS	[M+H-H2O]+	181.6	32859911
AllCCS	[M+NH4]+	187.2	32859911
AllCCS	[M+Na]+	188.0	32859911
AllCCS	[M-H]-	185.2	32859911
AllCCS	[M+Na-2H]-	187.1	32859911
AllCCS	[M+HCOO]-	189.3	32859911

Predicted Kovats Retention Indices

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Dihomo-gamma-linolenic acid,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C	2391.4	Semi standard non polar	33892256
Dihomo-gamma-linolenic acid,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C	2367.2	Standard non polar	33892256
Dihomo-gamma-linolenic acid,1TMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C	2591.8	Standard polar	33892256
Dihomo-gamma-linolenic acid,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2638.4	Semi standard non polar	33892256
Dihomo-gamma-linolenic acid,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2564.4	Standard non polar	33892256
Dihomo-gamma-linolenic acid,1TBDMS,isomer #1	CCCCC/C=C\C/C=C\C/C=C\CCCCCCC(=O)O[Si](C)(C)C(C)(C)C	2626.9	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-linolenic acid GC-MS (Non-derivatized) - 70eV, Positive	splash10-0006-9570000000-cd036d3430a12b16dfb6	2017-08-28	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihomo-gamma-linolenic acid GC-MS (1 TMS) - 70eV, Positive	splash10-022i-9542000000-c2f35f73d1bcbb0128a3	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihomo-gamma-linolenic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Dihomo-gamma-linolenic acid GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid Quattro_QQQ 10V, Positive-QTOF (Annotated)	splash10-0a4i-0019000000-38de24f5141b8fd24471	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid Quattro_QQQ 25V, Positive-QTOF (Annotated)	splash10-066v-9700000000-ea3e83fc76a5e8bf96a0	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid Quattro_QQQ 40V, Positive-QTOF (Annotated)	splash10-0k96-9200000000-2b1245d775cb6a9290a7	2012-07-25	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid Linear Ion Trap , negative-QTOF	splash10-03di-0090000000-8151054828665541898d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid Linear Ion Trap , positive-QTOF	splash10-05e9-0491000000-a09d13fe83820b375121	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid Linear Ion Trap , positive-QTOF	splash10-052e-0692000000-aba537ad7f934032649f	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid 20V, Positive-QTOF	splash10-0adj-0920000000-14556c974d2f5a8357cd	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid 10V, Positive-QTOF	splash10-059i-0791000000-db1fa7d2bf17ecf40820	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid 40V, Positive-QTOF	splash10-0a4i-0910000000-23e553ce4de5f9a92f32	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid 10V, Positive-QTOF	splash10-0a4r-0196000000-0cb348afdbc2bfa250ad	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid 20V, Positive-QTOF	splash10-03di-5891000000-413e3aa407f0e1cb6465	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid 40V, Positive-QTOF	splash10-052g-9760000000-b7aed55f7d8853fa6cf7	2017-07-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid 10V, Negative-QTOF	splash10-0a4i-0029000000-d1aef216444b744a8339	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid 20V, Negative-QTOF	splash10-0a4i-1079000000-1eb636eb88d281beeffe	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid 40V, Negative-QTOF	splash10-0a4i-9230000000-c1354a863e0181f2b709	2017-07-26	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid 10V, Positive-QTOF	splash10-0a4r-4496000000-d2c86b500de1b25b89bd	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid 20V, Positive-QTOF	splash10-0a5i-8920000000-c9e205f0c9bc159b6e85	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid 40V, Positive-QTOF	splash10-05o4-9300000000-6f4b5c73d4ea8dd6ce7c	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid 10V, Negative-QTOF	splash10-0a4i-0019000000-a547ddaba8c204ad4b7f	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid 20V, Negative-QTOF	splash10-0a4r-2069000000-bf269de6180612c37971	2021-09-22	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Dihomo-gamma-linolenic acid 40V, Negative-QTOF	splash10-0006-9220000000-00dffbb43465bcaae37f	2021-09-22	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted 1D NMR	¹³C NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 100 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 1000 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 200 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 300 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 400 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 500 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 600 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 700 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 800 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹³C NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Predicted 1D NMR	¹H NMR Spectrum (1D, 900 MHz, H₂O, predicted)	2022-08-22	Wishart Lab	View Spectrum
Experimental 2D NMR	[¹H, ¹³C]-HSQC NMR Spectrum (2D, 600 MHz, CDCl₃, experimental)	2012-12-05	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular
Membrane (predicted from logP)

Biospecimen Locations

Blood
Feces
Saliva

Tissue Locations

Adipose Tissue
Epidermis
Placenta

Pathways

Name	SMPDB/PathBank	KEGG
alpha-Linolenic acid metabolism	Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	0.542 +/- 0.005 uM	Adult (>18 years old)	Both	Normal	20671299	details
Blood	Detected and Quantified	3.61 +/- 2.1 uM	Adult (>18 years old)	Both	Normal	21359215	details
Blood	Detected and Quantified	118.408 +/- 39.774 uM	Adult (>18 years old)	Female	Normal	9368807	details
Blood	Detected and Quantified	0.420 +/- 0.207 uM	Adult (>18 years old)	Both	Normal	18953024 21359215	details
Blood	Detected and Quantified	0.54 +/- 0.005 uM	Adult (>18 years old)	Both	Normal	20671299	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	29808030	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	27543620	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	25037050	details

Abnormal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected and Quantified	84.8 +/- 30.8 uM	Adult (>18 years old)	Not Specified	Isovaleric acidemia	27329611	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal cancer	25037050	details
Feces	Detected but not Quantified	Not Quantified	Newborn (0-30 days old)	Not Specified	Premature neonates	23210743	details
Feces	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Colorectal Cancer	27275383	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Attachment loss	31026179	details
Saliva	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Male	Periodontal Probing Depth	31026179	details

Associated Disorders and Diseases

Disease References

Isovaleric acidemia
Dercksen M, Kulik W, Mienie LJ, Reinecke CJ, Wanders RJ, Duran M: Polyunsaturated fatty acid status in treated isovaleric acidemia patients. Eur J Clin Nutr. 2016 Oct;70(10):1123-1126. doi: 10.1038/ejcn.2016.100. Epub 2016 Jun 22. [PubMed:27329611 ]
Colorectal cancer
Brown DG, Rao S, Weir TL, O'Malia J, Bazan M, Brown RJ, Ryan EP: Metabolomics and metabolic pathway networks from human colorectal cancers, adjacent mucosa, and stool. Cancer Metab. 2016 Jun 6;4:11. doi: 10.1186/s40170-016-0151-y. eCollection 2016. [PubMed:27275383 ] Goedert JJ, Sampson JN, Moore SC, Xiao Q, Xiong X, Hayes RB, Ahn J, Shi J, Sinha R: Fecal metabolomics: assay performance and association with colorectal cancer. Carcinogenesis. 2014 Sep;35(9):2089-96. doi: 10.1093/carcin/bgu131. Epub 2014 Jul 18. [PubMed:25037050 ]
Attachment loss
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]
Periodontal Probing Depth
Liebsch C, Pitchika V, Pink C, Samietz S, Kastenmuller G, Artati A, Suhre K, Adamski J, Nauck M, Volzke H, Friedrich N, Kocher T, Holtfreter B, Pietzner M: The Saliva Metabolome in Association to Oral Health Status. J Dent Res. 2019 Jun;98(6):642-651. doi: 10.1177/0022034519842853. Epub 2019 Apr 26. [PubMed:31026179 ]

Associated OMIM IDs

243500 (Isovaleric acidemia)
114500 (Colorectal cancer)

External Links

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

VMH ID

CE2516

MarkerDB ID

MDB00030006

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Download (PDF)

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 ]
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 ]

Enzymes

Enzyme Details

1. Bile acid-CoA:amino acid N-acyltransferase

General function:: Involved in thiolester hydrolase activity
Specific function:: Involved in bile acid metabolism. In liver hepatocytes catalyzes the second step in the conjugation of C24 bile acids (choloneates) to glycine and taurine before excretion into bile canaliculi. The major components of bile are cholic acid and chenodeoxycholic acid. In a first step the bile acids are converted to an acyl-CoA thioester, either in peroxisomes (primary bile acids deriving from the cholesterol pathway), or cytoplasmic at the endoplasmic reticulum (secondary bile acids). May catalyze the conjugation of primary or secondary bile acids, or both. The conjugation increases the detergent properties of bile acids in the intestine, which facilitates lipid and fat-soluble vitamin absorption. In turn, bile acids are deconjugated by bacteria in the intestine and are recycled back to the liver for reconjugation (secondary bile acids). May also act as an acyl-CoA thioesterase that regulates intracellular levels of free fatty acids. In vitro, catalyzes the hydrolysis of long- and very long-chain saturated acyl-CoAs to the free fatty acid and coenzyme A (CoASH), and conjugates glycine to these acyl-CoAs.
Gene Name:: BAAT
Uniprot ID:: Q14032
Molecular weight:: 46298.865

Enzyme Details

2. Cytosolic acyl coenzyme A thioester hydrolase

General function:: Lipid transport and metabolism
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May play an important physiological function in brain. May play a regulatory role by modulating the cellular levels of fatty acyl-CoA ligands for certain transcription factors as well as the substrates for fatty acid metabolizing enzymes, contributing to lipid homeostasis. Has broad specificity, active towards fatty acyl-CoAs with chain-lengths of C8-C18. Has a maximal activity toward palmitoyl-CoA.
Gene Name:: ACOT7
Uniprot ID:: O00154
Molecular weight:: 40454.945

Reactions

Dihomo-gamma-linolenyl coenzyme A + Water → Coenzyme A + Dihomo-gamma-linolenic acid	details

Enzyme Details

3. Acyl-coenzyme A thioesterase 2, mitochondrial

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Displays high levels of activity on medium- and long chain acyl CoAs.
Gene Name:: ACOT2
Uniprot ID:: P49753
Molecular weight:: 53218.02

Reactions

Dihomo-gamma-linolenyl coenzyme A + Water → Coenzyme A + Dihomo-gamma-linolenic acid	details

Enzyme Details

4. Acyl-coenzyme A thioesterase 4

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH (By similarity). Succinyl-CoA thioesterase that also hydrolyzes long chain saturated and unsaturated monocarboxylic acyl-CoAs.
Gene Name:: ACOT4
Uniprot ID:: Q8N9L9
Molecular weight:: 46326.09

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Dihomo-gamma-linolenyl coenzyme A + Water → Coenzyme A + Dihomo-gamma-linolenic acid	details

Enzyme Details

5. Acyl-coenzyme A thioesterase 8

General function:: Involved in acyl-CoA thioesterase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. May mediate Nef-induced down-regulation of CD4. Major thioesterase in peroxisomes. Competes with BAAT (Bile acid CoA: amino acid N-acyltransferase) for bile acid-CoA substrate (such as chenodeoxycholoyl-CoA). Shows a preference for medium-length fatty acyl-CoAs (By similarity). May be involved in the metabolic regulation of peroxisome proliferation.
Gene Name:: ACOT8
Uniprot ID:: O14734
Molecular weight:: 35914.02

Enzyme Details

6. Acyl-coenzyme A thioesterase 1

General function:: Involved in thiolester hydrolase activity
Specific function:: Acyl-CoA thioesterases are a group of enzymes that catalyze the hydrolysis of acyl-CoAs to the free fatty acid and coenzyme A (CoASH), providing the potential to regulate intracellular levels of acyl-CoAs, free fatty acids and CoASH. Active towards fatty acyl-CoA with chain-lengths of C12-C16 (By similarity).
Gene Name:: ACOT1
Uniprot ID:: Q86TX2
Molecular weight:: 46276.96

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Dihomo-gamma-linolenyl coenzyme A + Water → Coenzyme A + Dihomo-gamma-linolenic acid	details

Showing metabocard for Dihomo-gamma-linolenic acid (HMDB0002925)

MOL for HMDB0002925 (Dihomo-gamma-linolenic acid)

3D MOL for HMDB0002925 (Dihomo-gamma-linolenic acid)

3D SDF for HMDB0002925 (Dihomo-gamma-linolenic acid)

3D-SDF for HMDB0002925 (Dihomo-gamma-linolenic acid)

PDB for HMDB0002925 (Dihomo-gamma-linolenic acid)

3D PDB for HMDB0002925 (Dihomo-gamma-linolenic acid)

SMILES for HMDB0002925 (Dihomo-gamma-linolenic acid)

INCHI for HMDB0002925 (Dihomo-gamma-linolenic acid)

Structure for HMDB0002925 (Dihomo-gamma-linolenic acid)

3D Structure for HMDB0002925 (Dihomo-gamma-linolenic acid)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

Enzymes

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