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Ligand gamma-linolenic acid

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Basic Ligand Information

Molecular Structure
Picture of gamma-linolenic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C18H30O2
gamma-linolenic acid
VZCCETWTMQHEPK-QNEBEIHSSA-N
Synonyms:
(6Z,9Z,12Z)-octadec-6,9,12-trienoic acid, (6Z,9Z,12Z)-octadeca-6,9,12-trienoate, (6Z,9Z,12Z)-octadeca-6,9,12-trienoic acid, (6Z,9Z,12Z)-octadecatrienoate, (6Z,9Z,12Z)-octadecatrienoic acid, (Z,Z,Z)-6,9,12-octadecatrienoic acid, 6(Z),9(Z),12(Z)-octadecatrienoic acid, 6,9,12-octadecatrienoic acid, 6-cis,9-cis,12-cis-octadecatrienoic acid, gamma-linolenate, gamma-linolenic-acid, gamma-linolenoate, gamma linolenic acid, octadec-6,9,12-trienoic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
gamma-linolenate + O2 = ?
show the reaction diagram
-
gamma-linolenic acid + O2 = (6Z,9R,10E,12Z)-9-hydroxy-octadeca-6,10,12-trienoic acid
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
linoleic acid + AH2 + O2 = gamma-linolenic acid + A + H2O
show the reaction diagram
-
linoleic acid + reduced ferredoxin [iron-sulfur] cluster + O2 + H+ = gamma-linolenic acid + oxidized ferredoxin [iron-sulfur] cluster + H2O
show the reaction diagram
-

Substrate in Enzyme-catalyzed Reactions (27 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
gamma-linolenic acid + O2 = ?
show the reaction diagram
-
gamma-linolenic acid + O2 = (6Z,9Z,11E)-(13)-hydroperoxyoctadecatrienoic acid + (6Z,9Z,12Z)-(11)-hydroperoxyoctadecatrienoic acid
show the reaction diagram
-
gamma-linolenic acid + O2 = (R)-8-hydroxy-gamma-linolenic acid
show the reaction diagram
-
gamma-linolenic acid + O2 = ?
show the reaction diagram
-
gamma-linolenic acid + AH2 + O2 = cis-6,9,12,15-octadecatetraenoic acid + A + H2O
show the reaction diagram
-
(6Z,9Z,12Z)-octadeca-6,9,12-trienoate + 2 ferrocytochrome b5 + O2 + 2 H+ = (6Z,9Z,11E,13E)-octadeca-6,9,11,13-tetraenoate + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
-
6-cis,9-cis,12-cis-octadecatrienoic acid = ?
show the reaction diagram
-
(6Z,9Z,12Z)-octadecatrienoate = (6Z,8E,10E)-octadecatrienoate
show the reaction diagram
-
(6Z,9Z,12Z)-octadecatrienoic acid = (6Z,10E,12Z)-octadecatrienoic acid
show the reaction diagram
-
ATP + (6Z,9Z,12Z)-octadecatrienoate + CoA = AMP + diphosphate + (6Z,9Z,12Z)-octadecatrienoyl-CoA
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
linoleic acid + reduced ferredoxin [iron-sulfur] cluster + O2 + H+ = gamma-linolenic acid + oxidized ferredoxin [iron-sulfur] cluster + H2O
show the reaction diagram
-
gamma-linolenoyl-CoA + H2O = CoA + gamma-linolenoate
show the reaction diagram
-
gamma-linolenoyl-CoA + H2O = CoA + gamma-linolenoate
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (2 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
a combination of gamma-linolenic acid and phosphatidylserine slightly enhances PKC zeta activity
-

Inhibitor in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
the incubation of Jurkat cells with 0.05 mM gamma-linolenic acid causes a significant decrease of catalase activity but not of protein or mRNA content
-
a natural product found in oil of evening primrose, Oenothera biennis, oil and borage, Borago officinalis, inhibits SRD5alpha1 and SRD5alpha2
-
inhibits CPT I in vivo and reduces malonyl-CoA sensitivity, decreases affinity for 16:0 acyl-CoA substrate
-
IC50: 0.12 mM
-
substrate inhibition at concentrations above 0.015 mM
-

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (7 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.81
-
at pH 8.5 and 35°C

KM Value (14 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.073
-
at pH 8.5 and 35°C
0.0258
-
pH 7.5, 22°C
0.009
-
pH 8.5, 30°C

IC50 Value (2 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.12
-
IC50: 0.12 mM
0.019
-
pH 7.4, 37°C, recombinant CES1

References & Links

Links to other databases for gamma-linolenic acid

ChEBI
PubChem
ChEBI
PubChem