Ligand hexadecanoic acid

Please wait a moment until all data is loaded. This message will disappear when all data is loaded.

Basic Ligand Information

Molecular Structure
Picture of hexadecanoic acid (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C16H32O2
hexadecanoic acid
IPCSVZSSVZVIGE-UHFFFAOYSA-N
Synonyms:
a long-chain-fatty-acid anion, a long-chain-fatty acid, a long-chain acid anion, a long-chain carboxylate, a long-chain carboxylic acid, a long-chain fatty acid, hexadecanoate, long-chain acid anion, long-chain carboxylate, long-chain carboxylic acid, palmitate, palmitic acid, palmitoate

Show all pahtways known for Show all pathways known for hexadecanoic acid

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (19 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
palmitate + H2O2 = pentadecanal + CO2 + H2O
show the reaction diagram
-
palmitic acid + [reduced NADPH-hemoprotein reductase] + O2 = 16-hydroxypalmitic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
hexadecanoate + acceptor + O2 + H+ = (11E)-hexadecenoate + ?
show the reaction diagram
-
palmitic acid + reduced acceptor + O2 = hexadec-11-enoic acid + acceptor + 2 H2O
show the reaction diagram
-
a long-chain fatty acid + hv = a long-chain alkane + CO2
show the reaction diagram
-
ATP + a long-chain fatty acid + holo-[mycocerosate synthase] = AMP + diphosphate + a long-chain acyl-[mycocerosate synthase]
show the reaction diagram
-

In Vivo Product in Enzyme-catalyzed Reactions (32 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
long-chain alcohol + NAD+ + H2O = long-chain carboxylate + NADH
show the reaction diagram
-
-
acetyl-CoA + 7 malonyl-CoA + 14 NADPH + 14 H+ = palmitate + 8 CoA + 7 CO2 + 14 NADP+ + 6 H2O
show the reaction diagram
-
-
1-palmitoyl-2-oleoyl-phosphatidylcholine + H2O = 2-oleoyl-lysophosphatidylcholine + palmitic acid
show the reaction diagram
-
1,2-dipalmitoyl-sn-glycero-3-phosphocholine + H2O = 1-palmitoylglycerophosphocholine + palmitic acid
show the reaction diagram
-
palmitoyl-protein + H2O = palmitate + protein
show the reaction diagram
-
palmitoylethanolamide + H2O = palmitic acid + ethanolamine
show the reaction diagram
-
-
aculeacin A + H2O = ? + palmitic acid
show the reaction diagram
-
-

Substrate in Enzyme-catalyzed Reactions (77 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
palmitate + H2O2 = pentadecanal + CO2 + H2O
show the reaction diagram
-
palmitic acid + H2O2 = 15-hydroxypalmitic acid + 14-hydroxypalmitic acid + H2O
show the reaction diagram
palmitic acid + ATP + CoA = palmitoyl-CoA + AMP + diphosphate
show the reaction diagram
-
palmitic acid + [reduced NADPH-hemoprotein reductase] + O2 = 16-hydroxypalmitic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
palmitic acid + [reduced NADPH-hemoprotein reductase] + O2 = 16-hydroxypalmitic acid + [oxidized NADPH-hemoprotein reductase] + H2O
show the reaction diagram
-
palmitic acid + O2 + reduced ferredoxin [iron-sulfur] cluster + H+ = ?
show the reaction diagram
-
palmitic acid + NAD(P)H + H+ + O2 = 16-hydroxyhexadecanoic acid + NAD(P)+ + H2O
show the reaction diagram
-
palmitic acid + 2 ferrocytochrome b5 + O2 + 2 H+ = (R)-2-hydroxypalmitic acid + 2 ferricytochrome b5 + H2O
show the reaction diagram
-
hexadecanoate + acceptor + O2 + H+ = (11E)-hexadecenoate + ?
show the reaction diagram
-
S-adenosyl-L-methionine + palmitic acid = S-adenosyl-L-homocysteine + methyl palmitate
show the reaction diagram
-
myristyl-CoA + palmitic acid = myristyl palmitate
show the reaction diagram
-
beta-D-glucosyl 4,4'-diaponeurosporenoate + palmitate = [(6-O-palmitoyl)-beta-D-glucosyl] 4,4'-diaponeurosporenoate + H2O
show the reaction diagram
-
glycerol + palmitic acid = monopalmitin + H2O
show the reaction diagram
-
palmitic acid + isopropanol = isopropyl palmitate + H2O
show the reaction diagram
-
palmitate + ethanol = ethyl palmitate + H2O
show the reaction diagram
-
D-erythro-sphingosine + palmitic acid = N-palmitoyl-D-erythro-sphingosine + H2O
show the reaction diagram
palmitic acid + lyso-GM1a = ? + H2O
show the reaction diagram
-
a long-chain fatty acid + hv = a long-chain alkane + CO2
show the reaction diagram
-
GTP + palmitate + CoA = GDP + phosphate + palmitoyl-CoA
show the reaction diagram
-
ATP + hexadecanoate + CoA = AMP + diphosphate + hexadecanoyl-CoA
show the reaction diagram
-
ATP + palmitate + CoA = AMP + diphosphate + palmityl-CoA
show the reaction diagram
-
ATP + a long-chain fatty acid + holo-[mycocerosate synthase] = AMP + diphosphate + a long-chain acyl-[mycocerosate synthase]
show the reaction diagram
-
hexadecanoic acid + CoA + ATP = hexadecanoyl-CoA + AMP + diphosphate
show the reaction diagram
-

Product in Enzyme-catalyzed Reactions (268 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
hexadecanal + NAD+ + H2O = hexadecanoate + NADH + H+
show the reaction diagram
-
-
hexadecanal + NAD+ = hexadecanoate + NADH
show the reaction diagram
-
Palmitoyl-CoA + H2O = Palmitate + CoA
show the reaction diagram
-
-
p-nitrophenyl palmitate + H2O = p-nitrophenol + palmitate
show the reaction diagram
-
-
4-nitrophenyl palmitate + H2O = 4-nitrophenol + palmitate
show the reaction diagram
-
-
1-acyl-2-palmitoyl-sn-glycerol-3-phosphoinositol + H2O = 1-acylglycerophosphoinositol + palmitic acid
show the reaction diagram
-
11-cis-retinyl palmitate + H2O = 11-cis-retinol + palmitate
show the reaction diagram
-
p-nitrophenyl palmitate + H2O = p-nitrophenol + palmitate
show the reaction diagram
-
-
palmitoyl-CoA = palmitate + CoA
show the reaction diagram
-
-
hexadecanoyl-[acyl-carrier protein] + H2O = [acyl-carrier protein] + hexadecanoate
show the reaction diagram
-
-
N-palmitoyl-L-glutamate + H2O = palmitate + L-glutamate
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (19 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
stimulates
-
concomitant treatment with palmitate/bovine serum albumin and activators of PKA (forskolin), PDK/PI3K (insulin), and PKC (TPA) increase Miox activity. Concomitant treatment with respective inhibitors, i.e. H89 (PKA), wortmannin (PI3K), and calphostin (PKC), reduces the activity below the levels induced by palmitate/bovine serum albumin alone, confirming that fatty acid-induced activity is phosphorylation-dependent
-
stimulation
-
0.02-0.05 mM, stimulates
-
approx. 2fold activiation
-
stimulates
-
enhancement factor: 0.8 in absence of Triton X-100, 1.4 in presence of 0.1% Triton X-100
-
activates only in presence of Triton X-100
-
activates isozyme PKCtheta, but not isozymes PKCalpha and PKCepsilon
-
activates PDK2 and PDK4 nearly 2fold at 0.1 mM, not synergistic with oleate, stimulation is completely inhibited by insulin at 0.001 mmM
-
activates p38 MAPK phosphorylation and activates it
-
palmitic acid-induced nuclear entry of heparanase facilitates heparan sulfate cleavage
-
caspase-2 is activated by an overabundance of saturated long-chain fatty acids like palmitate. Inhibition of amino acid transamination by 10 mM aminooxyacetate blocks caspase activation
-
the activity of MCD elicits a dose-dependent increase (between 25% and 60%) in cells exposed to increasing concentrations of palmitate (0.1-0.8 mM)
-
stimulates 3fold
-

Inhibitor in Enzyme-catalyzed Reactions (45 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.01 mM
-
inhibits enzyme in dose-dependent manner
-
competitive inhibition
-
the incubation of Jurkat cells with 0.2 mM palmitic acid causes a significant decrease of catalase activity but not of protein or mRNA content
-
IC50: 0.00067 mM
-
enzyme expression is reduced in 3T3-L1 cells differentiated in presence of 400 microM palmitic acid
-
0.15 mM, 50% inhibition
-
IC50 in the range 1-100 mM
-
0.1 mM
-
IC50: 0.0624 mM, TbHK1
-
2 mM, 76% inhibition
-
1 mM inhibits by 30%
-
1 mM inhibits by 30%
-
a non-substrate lipid belonging to the phospholipase A2 pathway
-
supresses cleavage by dS1P
-
IC50: 0.035 mM
-
weak inhibition
-
linolenic acid activation
-
IC50: 0.009 mM, at 25C and pH 8.0
-

3D Structure of Enzyme-Ligand-Complex (PDB) (90 results)

EC NUMBER
ENZYME 3D STRUCTURE

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (18 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
25.65
-
CYP102A7, at pH 7.5, highest binding affinity
0.03
-
at pH 7.4 and 37C
0.000683
-
at pH 7.5 and 25C
0.026
-
recombinant enzyme, pH 7.5, 30C

KM Value (36 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0009
-
-
0.0386
-
CYP102A7, at pH 7.5, highest activity
0.047
-
at pH 7.4 and 37C
3.3
-
-
0.092
-
recombinant enzyme, pH 7.5, 30C

Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0054
-
at pH 7.5 and 30C

IC50 Value (6 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.00067
-
IC50: 0.00067 mM
0.5
-
pH 6.9, 37C
1
100
IC50 in the range 1-100 mM
0.0624
-
IC50: 0.0624 mM, TbHK1
0.025
-
pH 7.4, 37C, recombinant CES1
0.009
-
IC50: 0.009 mM, at 25C and pH 8.0

References & Links

Links to other databases for hexadecanoic acid

ChEBI
PubChem
ChEBI
PubChem