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BRENDA support

Ligand octadecanoic acid

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Basic Ligand Information

Molecular Structure
Picture of octadecanoic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C18H36O2
octadecanoic acid
QIQXTHQIDYTFRH-UHFFFAOYSA-N
Synonyms:
18-carbon fatty acid, a fatty acid, a fatty acid anion, fatty acid, fatty acid anion, fatty acids, long-chain fatty acid, long-chain fatty acids, long chain fatty acids, octadecanoate, Octadecansaeure, stearate, stearic acid, Straight-chain fatty acids, unesterified fatty acid
Pathway Source
Pathways
BRENDA
degradation of sugar alcohols, lipid metabolism
KEGG
Adipocytokine signaling pathway, AMPK signaling pathway, Biosynthesis of plant secondary metabolites, Biosynthesis of secondary metabolites, Biosynthesis of unsaturated fatty acids more
MetaCyc
2-arachidonoylglycerol biosynthesis, acyl-[acyl-carrier protein] thioesterase pathway, alkane biosynthesis I, alkane biosynthesis II, alkane oxidation more


Show all pahtways known for Show all BRENDA pathways known for octadecanoic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (8 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
fatty acid + H2O2 = ?
show the reaction diagram
-
stearic acid + [reduced NADPH-hemoprotein reductase] + O2 = 18-hydroxystearic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
stearate + AH2 + O2 = oleate + A + 2 H2O
show the reaction diagram
-
fatty acid + ATP + NADPH + H+ = fatty aldehyde + AMP + diphosphate + NADP+
show the reaction diagram
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S-adenosyl-L-methionine + a fatty acid = S-adenosyl-L-homocysteine + a fatty acid methyl ester
show the reaction diagram
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11-cis-retinol + a fatty acid = all-trans-retinyl ester + H2O
show the reaction diagram
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fatty acid + ethanol = fatty acyl ethyl ester + H2O
show the reaction diagram
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ATP + octadecanoate + CoA = AMP + diphosphate + octadecanoyl-CoA
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (28 results)

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EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
fatty aldehyde + FMNH2 + O2 = fatty acid + FMN + H2O + hn
show the reaction diagram
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a 1,2-diacyl-sn-glycerol 3-phosphate + H2O = a 2-acyl-sn-glycerol 3-phosphate + a fatty acid
show the reaction diagram
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O-fatty-acyl-L-carnitine + H2O = fatty acid + L-carnitine
show the reaction diagram
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1-acyl-2-lysophosphatidylcholine + H2O = fatty acid + glycerophosphocholine
show the reaction diagram
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an all-trans-retinyl ester + H2O = 13-cis-retinol + a fatty acid
show the reaction diagram
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stearoyl-[acyl-carrier protein] + H2O = stearic acid + acyl-carrier protein
show the reaction diagram
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stearoyl-CoA + H2O = CoA + stearate
show the reaction diagram
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glucosyl ceramide + H2O = sphingosine + fatty acid + beta-D-glucose
show the reaction diagram
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N-stearoylethanolamide + H2O = stearate + ethanolamine
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (49 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
stearic acid + H2O2 = 17-hydroxystearic acid + 16-hydroxystearic acid + H2O
show the reaction diagram
-
fatty acid + H2O2 = ?
show the reaction diagram
-
fatty acid + ATP + CoA = fatty acyl-CoA + AMP
show the reaction diagram
-
stearic acid + [reduced NADPH-hemoprotein reductase] + O2 = 18-hydroxystearic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
octadecanoate + AH2 + O2 = ? + A + H2O
show the reaction diagram
-
stearic acid + NADH + ? = oleic acid + NAD+ + ?
show the reaction diagram
-
S-adenosyl-L-methionine + a fatty acid = S-adenosyl-L-homocysteine + a fatty acid methyl ester
show the reaction diagram
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stigmasterol + stearate = stigmasteryl stearate + H2O
show the reaction diagram
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glycerol + stearic acid = monostearin + H2O
show the reaction diagram
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3-O-beta-D-galactopyranosyl-1,2-di-O-dodecanoyl-sn-glycerol + fatty acid + H2O = 2,3-dihydroxypropyl-beta-D-galactopyranoside + dodecanoate
show the reaction diagram
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11-cis-retinol + a fatty acid = all-trans-retinyl ester + H2O
show the reaction diagram
-
fatty acids + H2O = ?
show the reaction diagram
-
ATP + octadecanoate + CoA = AMP + diphosphate + octadecanoyl-CoA
show the reaction diagram
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ATP + stearate + CoA = AMP + diphosphate + stearyl-CoA
show the reaction diagram
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octadecanoic acid + CoA + ATP = octadecanoyl-CoA + AMP + diphosphate
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (189 results)

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EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
1-octadecanol + 2 NAD+ + H2O = octadecanoic acid + 2 NADH + 2 H+
show the reaction diagram
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tetradecanol + H2O2 = 13-hydroxytetradecanol + 12-hydroxytetradecanol + stearic acid + 13-hydroxystearic acid + 12-hydroxystearic acid + H2O
show the reaction diagram
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long-chain aldehyde + FMNH2 + O2 = long-chain fatty acid + FMN + H2O + hv
show the reaction diagram
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fatty aldehyde + FMNH2 + O2 = fatty acid + FMN + H2O + hn
show the reaction diagram
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octadecanal + NAD+ + H2O = octadecanoate + NADH + H+
show the reaction diagram
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1-acyl-2-stearoyl-sn-glycerol-3-phosphoinositol + H2O = 1-acylglycerophosphoinositol + stearic acid
show the reaction diagram
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monoacylglycerol + H2O = fatty acid + glycerol
show the reaction diagram
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4-nitrophenyl stearate + H2O = 4-nitrophenol + stearate
show the reaction diagram
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an all-trans-retinyl ester + H2O = 13-cis-retinol + a fatty acid
show the reaction diagram
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glucosyl ceramide + H2O = sphingosine + fatty acid + beta-D-glucose
show the reaction diagram
-
12-phosphonooxyoctadecanoic acid + H2O = octadecanoic acid + phosphate
show the reaction diagram
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stearamide + H2O = stearic acid + NH3
show the reaction diagram
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N-stearoyl-L-glutamate + H2O = stearate + L-glutamate
show the reaction diagram
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acylpyruvate + H2O = fatty acid + pyruvate
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (17 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
with carbon chain length greater than nine at pH 7.0 activate, e.g. arachidonic acid
-
C18, natural detergents in DMPC vesicles, stimulation similar to octyl glucoside
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required for full activity
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approx. 2fold activiation
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enhancement factor: 0.07 in absence of Triton X-100, 0.8 in presence of 0.1% Triton X-100
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activates only in presence of Triton X-100
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activate PKN1
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leads to overexpression of isozyme PDK4 via mechanism involving peroxisome proliferator-activated receptor-alpha
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activity slightly enhanced by addition of saturated fatty acids, markedly increased by addition of unsaturated fatty acids regardless of chain length and number of double bonds
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approx. 20% stimulation at 0.4-0.8 mM, inhibition above
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stimulation
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increases MCD expression in heart and skeletal muscle
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Inhibitor in Enzyme-catalyzed Reactions (41 results)

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EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.01 mM
-
e.g. myristic acid, competitive with respect to (S)-ethyl 3-hydroxybutyrate
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the incubation of Jurkat cells with 0.2 mM stearic acid causes a significant decrease of catalase activity but not of protein or mRNA content
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IC50: 0.00063 mM
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of low molecular mass
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isoform 1, 50% inhibition above 0.1 mM, isoform 2, 50% inhibition above 0.1 mM
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oxidized unsaturated
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oleic acid, stearic acid, less efficient: palmitic acid, lauric acid, capric acid, caprylic acid or caproic acid, no inhibition by linoleic acid or linolenic acid
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unsaturated fatty acid of chain length C11-C14
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about 20% inhibition
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IC50: 0.03 mM
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fatty acids block aryl acylamidase activity competing with amides for binding in the catalytic domain
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weak inhibition
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overview
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inhibition is not important in vivo owing to the high concentrations required for inhibition
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3D Structure of Enzyme-Ligand-Complex (PDB) (690 results)

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EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (7 results)

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EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
16.18
-
CYP102A7, at pH 7.5
0.062
-
recombinant enzyme, pH 7.5, 30°C

KM Value (19 results)

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EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0118
-
CYP102A7, at pH 7.5
0.841
-
recombinant enzyme, pH 7.5, 30°C

Ki Value (5 results)

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EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
2.36
-
pH and temperature not specified in the publication

IC50 Value (3 results)

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EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.00063
-
IC50: 0.00063 mM
0.1
-
pH 7.4, 37°C, recombinant CES1
0.03
-
IC50: 0.03 mM

References & Links

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Links to other databases for octadecanoic acid

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ChEBI
PubChem
ChEBI
PubChem