Ligand alpha-linolenic acid

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Basic Ligand Information

Molecular Structure
Picture of alpha-linolenic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C18H30O2
alpha-linolenic acid
DTOSIQBPPRVQHS-PDBXOOCHSA-N
Synonyms:
(9Z,12Z,15Z)-9,12,15-octadecatrienoic acid, (9Z,12Z,15Z)-octadeca-9,12,15-trienoic acid, (9Z,12Z,15Z)-octadecatrienoate, (9Z,12Z,15Z)-octadecatrienoic acid, (Z,Z,Z)-9,12,15-octadecatrienoic acid, 9-cis,12-cis,15-cis-octadecatrienoic acid, 9Z,12Z,15Z-octadecatrienoic acid, 18:3n-3, all-cis-9,12,15-octadecatrienoic acid, alpha-linolenate, alpha-linolenic acid fatty acid, cis-9,-cis-12,cis-15-octadecatrienoic acid, cis-9,cis-12,cis-15-octadecatrienoic acid, linolenate, linolenic acid, linolenoate, octadeca-9c,12c,15c-trienoic acid

Show all pahtways known for Show all pathways known for alpha-linolenic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
alpha-linolenate + O2 = (9S,10E,12Z)-9-hydroperoxy-10,12-octadecadienoate
show the reaction diagram
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alpha-linolenate + O2 = (9R,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
show the reaction diagram
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alpha-linolenic acid + ferrocytochrome b5 + O2 + H+ = stearidonic acid + ferricytochrome b5 + H2O
show the reaction diagram
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alpha-linolenic acid + AH2 + O2 = octadec-6,9,12,15-tetraenoic acid + A + H2O
show the reaction diagram
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alpha-linolenic acid = (E,Z)-3,6-nonadienal + 9-oxononanoic acid
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (67 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
linolenate + O2 = 11-hydroperoxyoctadecatrienoic acid + 9-hydroperoxyoctadecatrienoic acid + 13-hydroperoxyoctadecatrienoic acid
show the reaction diagram
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alpha-linolenic acid + O2 = ?
show the reaction diagram
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alpha-linolenate + O2 = ?
show the reaction diagram
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alpha-linolenate + O2 = (9R,10E,12Z,15Z)-9-hydroperoxy-10,12,15-octadecatrienoate
show the reaction diagram
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alpha-linolenate + O2 = (8E,10R,12Z,15Z)-10-hydroperoxy-8,12,15-octadecatrienoate
show the reaction diagram
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alpha-linolenate + O2 = (8E,10S,12Z,15Z)-10-hydroperoxyoctadeca-8,12,15-trienoate
show the reaction diagram
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alpha-linolenic acid + O2 = (10E,12E,14E)-9,16-dihydroxy-10,12,14-octadecatrienoic acid
show the reaction diagram
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linolenic acid + NAD(P)H + H+ + O2 = ? + NAD(P)+ + H2O
show the reaction diagram
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alpha-linolenic acid + ferrocytochrome b5 + O2 + H+ = stearidonic acid + ferricytochrome b5 + H2O
show the reaction diagram
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linolenic acid + AH2 + O2 = ?
show the reaction diagram
(9Z,12Z,15Z)-octadecatrienoate = ?
show the reaction diagram
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ATP + linolenic acid + CoA = AMP + diphosphate + linolenoyl-CoA
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (13 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
linoleic acid + ferrocytochrome P-450 + O2 = linolenic acid + ferricytochrome P-450 + H2O
show the reaction diagram
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omega-6 linoleic acid + ferrocytochrome b5 + O2 + H+ = linolenic acid + ferricytochrome b5 + H2O
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oleate + AH2 + O2 = linoleic acid + linolenic acid + A + 2 H2O
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oleic acid + reduced acceptor + O2 = linoleic acid + alpha-linolenic acid + acceptor + H2O
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cholesteryl linolenate + H2O = cholesterol + linolenic acid
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linolenoyl-CoA + H2O = CoA + linolenoate
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linolenoyl-CoA + H2O = CoA + linolenoate
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N-linolenoyl-L-glutamine + H2O = linolenic acid + L-glutamine
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
126% of the activitation with palmitic acid
-
stimulation; stimulation
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a moderate dietary intake of myristic acid (1.8% total energy) and alpha-linolenic acid (0.9% total energy) increases LCAT activity
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0.3 mM, 28fold stimulation in the presence of 2 mM MgCl2, MgCl2 can be replaced by MnCl2, CaCl2 or high concetrations of KCl
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approx. 30% stimulation at 0.8-1.6 mM, inhibition above
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strong activation at 0.1 mM
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Inhibitor in Enzyme-catalyzed Reactions (20 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.018 mM, 34% inhibition, oxidation of estradiol
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3.6 mM, 16% inhibition of the activity with quercetin, 21% inhibition of the activity with o-dianisidine, isoenzyme POX I; 3.6 mM, 35% inhibition of the activity with quercetin, 37% inhibition of the activity with o-dianisidine, isoenzyme POX II
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strong inhibition
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IC50: 0.11 mM
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stimulation below 0.8 mM, approx. 15% inhibition at 3.2 mM
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IC50: 0.46 mM
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strong inhibition
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substrate inhibition at concentrations above 0.04 mM
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inhibition of palmitoyl-CoA synthesis
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3D Structure of Enzyme-Ligand-Complex (PDB) (1 result)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (6 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
47.8
-
25°C
0.13
-
-
0.13
-
at pH 6.5 and 25°C

KM Value (27 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.026
-
pH 7.5, 22°C, wild-type enzyme
0.73
-
in 0.2 M sodium borate buffer, pH 9.0, at 30°C
0.344
-
25°C
0.0136
-
-
0.059
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at pH 6.5 and 25°C

Ki Value (3 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.014
-
-

IC50 Value (5 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.0261
-
pH 7.4, 37°C, inhibition of recombinant enzyme
0.11
-
IC50: 0.11 mM
0.46
-
IC50: 0.46 mM

References & Links

Links to other databases for alpha-linolenic acid

ChEBI
PubChem
ChEBI
PubChem