Ligand palmitoyl-CoA

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Basic Ligand Information

Molecular Structure
Picture of palmitoyl-CoA (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C37H66N7O17P3S
palmitoyl-CoA
MNBKLUUYKPBKDU-BBECNAHFSA-N
Synonyms:
a long-chain-fatty acyl-CoA, a long-chain acyl-CoA, a long-chain fatty acyl-CoA, C16-C18 fatty acyl-CoA, hexadecanoyl-CoA, hexadecanoyl CoA, long-chain-acyl-CoA, long-chain acyl-CoA, long-chain acyl-CoA compounds, long-chain acyl-CoA thioesters, long-chain fatty acyl CoA/cis, long-chain fatty acyl CoA/trans, palmitoyl-SCoA, palmitoyl CoA, palmityl-CoA, palmityl CoA
Pathway Source
Pathways


Show all pahtways known for Show all BRENDA pathways known for palmitoyl-CoA

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (62 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
a long-chain acyl-CoA + 2 NADPH + 2 H+ = a long-chain alcohol + 2 NADP+ + coenzyme A
show the reaction diagram
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palmitoyl-CoA + O2 = trans-2,3-dehydropalmitoyl-CoA
show the reaction diagram
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palmitoyl-CoA + electron-transfer flavoprotein = (2E)-2-hexadecenoyl-CoA + reduced electron-transfer flavoprotein
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palmitoyl-CoA + myelin proteolipid protein = CoA + myelin proteolipid O-palmitoylprotein
show the reaction diagram
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palmitoyl-CoA + dolichol = CoA + dolichyl palmitate
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palmitoyl-CoA + sn-glycerol 3-phosphate = CoA + 1-palmitoyl-sn-glycerol 3-phosphate
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1-palmitoyl-2-lysophosphatidylcholine + palmitoyl-CoA = 1,2-dipalmitoylphosphatidylcholine + CoA
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a long-chain acyl-CoA + 3 (R)-methylmalonyl-CoA + 6 NADPH + 6 H+ + holo-[mycolipanoate synthase] = mycolipanoyl-[mycolipanoate synthase] + 4 CoA + 3 CO2 + 6 NADP+ + 3 H2O
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a long-chain-fatty acyl-CoA + alpha,alpha-trehalose = a 2-(long-chain-fatty acyl)-trehalose + CoA
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palmitoyl-CoA + dihydroxyacetone phosphate = CoA + monopalmitoyldihydroxyacetone phosphate
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ATP + H2O + long-chain fatty acyl CoA/cis = ADP + phosphate + long-chain fatty acyl CoA/trans
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
hexadecanal + CoA + NAD+ = hexadecanoyl-CoA + NADH + H+
show the reaction diagram
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-
(2E)-hexadec-2-enoyl-CoA + NADPH = palmitoyl-CoA + NADP+
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-
trans-2-hexadecenoyl-CoA + NADPH + H = palmitoyl-CoA + NADP+
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-
ATP + H2O + long-chain fatty acyl CoA/cis = ADP + phosphate + long-chain fatty acyl CoA/trans
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (311 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
hexadecanoyl-CoA + 2-oxoglutarate + O2 = 2-hydroxyhexadecanoyl-CoA + succinate + CO2
show the reaction diagram
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palmitoyl-CoA + [reduced NADPH-hemoprotein reductase] + O2 = 16-hydroxypalmitoyl-CoA + [oxidized NADPH-hemoprotein reductase] + H2O
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palmitoyl-CoA + NADH + ? = (Z)-hexadec-11-enoyl-CoA + NAD+ + ?
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palmitoyl-CoA + NADPH + H+ = ? + coenzyme A + NADP+
show the reaction diagram
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palmitoyl-CoA + electron-transfer flavoprotein = (2E)-2-hexadecenoyl-CoA + reduced electron-transfer flavoprotein
show the reaction diagram
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palmitoyl-CoA + myelin proteolipid protein = CoA + myelin proteolipid O-palmitoylprotein
show the reaction diagram
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palmitoyl-CoA + 1-alkenylglycerophosphoethanolamine = CoA + 1-alkenyl-2-palmitoylglycerophosphoethanolamine
show the reaction diagram
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palmitoyl-CoA + dolichol = CoA + dolichyl palmitate
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palmitoyl-CoA + ecdysone = CoA + ecdysone palmitate
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palmitoyl-CoA + H2O = palmitate + CoA
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palmitoyl-CoA + malonyl-[acyl-carrier protein] = 3-oxo-stearoyl-[acyl-carrier protein] + CoA + CO2
show the reaction diagram
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sn-glycerol 3-phosphate + palmitoyl-CoA = CoA + 2-palmitoyl-sn-glycerol 3-phosphate
show the reaction diagram
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a long-chain acyl-CoA + 3 (R)-methylmalonyl-CoA + 6 NADPH + 6 H+ + holo-[mycolipanoate synthase] = mycolipanoyl-[mycolipanoate synthase] + 4 CoA + 3 CO2 + 6 NADP+ + 3 H2O
show the reaction diagram
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palmitoyl-CoA + cholesterol = CoA + cholesteryl palmitate
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a long-chain-fatty acyl-CoA + alpha,alpha-trehalose = a 2-(long-chain-fatty acyl)-trehalose + CoA
show the reaction diagram
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palmitoyl-CoA + 2-acyl-sn-glycerol 3-phosphate = CoA + 1-palmitoyl-2-acyl-sn-glycerol 3-phosphate
show the reaction diagram
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palmitoyl-CoA + alkyl-lyso-glycero-3-phosphoethanolamine = CoA + acetyl-2-palmitoyl-glycero-3-phosphoethanolamine
show the reaction diagram
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palmitoyl-CoA + octopamine = CoA + N-palmitoyloctopamine
show the reaction diagram
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palmitoyl-CoA + glycerophosphocholine = CoA + 1-palmitoyl-sn-glycero-3-phosphocholine
show the reaction diagram
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palmitoyl-CoA + H2O + oxaloacetate = (2S,3S)-2-hydroxyheptadecane-1,2,3-tricarboxylate + CoA
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palmitoyl-CoA + H2O = ?
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palmitoyl-CoA + apo-[acyl-carrier protein] = ? + holo-[acyl-carrier protein]
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palmitoyl-CoA + H2O = palmitic acid + CoA
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palmitoyl-SCoA + H2O = HS-CoA + palmitic acid
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palmitoyl-CoA = palmitate + CoA
show the reaction diagram
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palmitoyl-CoA + H2O = palmitate + CoA
show the reaction diagram
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palmitoyl-CoA + H2O = palmitate + CoA
show the reaction diagram
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ATP + H2O + long-chain fatty acyl CoA/cis = ADP + phosphate + long-chain fatty acyl CoA/trans
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (22 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
palmitic acid + ATP + CoA = palmitoyl-CoA + AMP + diphosphate
show the reaction diagram
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hexadecanal + CoA + NAD+ = hexadecanoyl-CoA + NADH + H+
show the reaction diagram
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trans-2-hexadecenoyl-CoA + NADH + H+ = hexadecanoyl-CoA + NAD+
show the reaction diagram
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trans-2-hexadecenoyl-CoA + NADPH + H+ = palmitoyl-CoA + NADP+
show the reaction diagram
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trans-2-hexadecenoyl-CoA + NADH = hexadecanoyl-CoA + NAD+
show the reaction diagram
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trans-2-hexadecenoyl-CoA + NADH + H+ = hexadecanoyl-CoA + NAD+
show the reaction diagram
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trans-2-hexadecenoyl-CoA + NADPH + H = palmitoyl-CoA + NADP+
show the reaction diagram
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acetyl-CoA + 7 malonyl-CoA + 7 NADH + 7 NADPH + 14 H+ = palmitoyl-CoA + 7 CoA + 7 CO2 + 7 NAD+ + 7 NADP+ + 7 H2O
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GTP + palmitate + CoA = GDP + phosphate + palmitoyl-CoA
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ATP + hexadecanoate + CoA = AMP + diphosphate + hexadecanoyl-CoA
show the reaction diagram
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ATP + palmitate + CoA = AMP + diphosphate + palmityl-CoA
show the reaction diagram
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hexadecanoic acid + CoA + ATP = hexadecanoyl-CoA + AMP + diphosphate
show the reaction diagram
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ATP + H2O + long-chain fatty acyl CoA/cis = ADP + phosphate + long-chain fatty acyl CoA/trans
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (8 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
stimulates at low concentrations, inhibits above 0.1 mM
-
activates dynein between 2 and 0.01 mM, inhibites at 0.04 mM
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activated by long-chain acyl-CoA derivatives
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slight stimulative effect on acetyl-CoA carboxylase (116%) and propionyl-CoA carboxylase (135%)
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Inhibitor in Enzyme-catalyzed Reactions (112 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
inhibition is greatly diminished at high glucose 6-phosphate concentration
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0.0015 mM, 52% inhibition
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74% of control activity
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is 10-fold less potent than phytanoyl-CoA, no inhibitory effect up to 0.3 mM
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0.0016 mM lead to 50% inhibition, 0.002 mM to 60%, 0.005 mM to 20%, 0.01 mM to nearly total inhibition
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without bovine serum albumin substrate-induced inhibition at 0.02-0.03 mM
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24% residual activity at 0.1 mM
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at fairly low concentrations
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inhibition by micelle formation at concentrations up to 0.004 mM, reversed by fatty acid free bovine serum albumin
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covalent inhibition of TrxR1/hTrx1 by palmitoyl-CoA. The palmitoyl-CoA/TrxR1 reaction is NADPH-dependent and produces palmitoylated TrxR1 at an active site selenocysteine residue
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competitive to acetyl-CoA, non-competitive to dihydrolipoamide
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up to 0.03 mM
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high concentration
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noncompetitive inhibitor
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substrate inhibition
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substrate inhibition above 0.003 mM
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competitive
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malonyl-transferase reaction
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mitochondrial synthase
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partially competitive with lauroyl-CoA
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glucokinase is inhibited by endogenous long-chain fatty acyl-CoA in islets from omega3-depleted rats
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noncompetitive inhibition
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substrate inhibition
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inhibits enzyme activity in intact microsomes
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0.01 mM, 87% inhibition
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noncompetitive inhibition of 14S dynein ATPase at 0.040 mM, bovine serum albumin (1mg/ml) and spermine (0.1 and 1 mM) reverse inhibition
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irreversible inactivation in a time- and concentration-dependent manner, this fatty acylation is specific for long-chain fatty acyl-CoA
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25% inhibition
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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) (44 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
78
-
-
0.92
-
pH 7.0, 37°C
0.00045
-
pH 6.5, 387°C
0.08
-
acceptor malonyl-ACP, 0.01 mM malonyl-ACP, pH 8.5, 25°C
0.16
-
pH 8.0, temperature not specified in the publication
0.4
-
pH 7.5, 22°C
0.1
-
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KM Value (244 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.029
-
-
0.041
-
-
0.038
-
-
0.004
-
pH 6.5, 387°C
0.0004
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acceptor malonyl-ACP, 0.01 mM malonyl-ACP, pH 8.5, 25°C
0.0072
-
mutant enzyme D356A/M564G
0.13
-
-
0.0099
-
pH 8.0, temperature not specified in the publication
0.0012
-
pH 7.5, 22°C
0.017
-
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Ki Value (24 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.0025
-
-
0.0095
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in 50 mM Tris/HCI pH 6.5 and 10% (v/v) glycerol, at 30°C
0.02
-
-
0.0096
-
pH 6.5, 37°C
0.0007
-
substrate AtSOS3 + myristoyl-CoA
0.0005
-
-
0.01
-
pH 6.0, 30°C
0.0008
-
-

IC50 Value (6 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.012
-
pH 7.4, 37°C
0.0015
-
in 50 mM imidazole, pH 8.0, containing 50 mM KCl and 2 mM MgCl2, at 22°C

References & Links