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Information on EC 3.1.1.67 - fatty-acyl-ethyl-ester synthase
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EC Tree
3.1.1.67 fatty-acyl-ethyl-ester synthaseIUBMB Comments
The reaction, forms ethyl esters from fatty acids and ethanol in the absence of coenzyme A or ATP. Best substrates are unsaturated octadecanoic acids; palmitate, stearate and arachidonate also act, but more slowly.
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Word Map
The enzyme appears in viruses and cellular organisms
Reaction Schemes
Synonyms
faees, faee synthase, fatty acid ethyl ester synthase, 
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
FAEE synthase
FAEES
fatty acid ethyl ester synthase
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synthase, fatty acid ethyl ester
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FAEE synthase
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FAEES
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a long-chain-fatty-acyl ethyl ester + H2O = a long-chain-fatty acid + ethanol
mechanism
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a long-chain-fatty-acyl ethyl ester + H2O = a long-chain-fatty acid + ethanol
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
hydrolysis of carboxylic ester
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SYSTEMATIC NAME
IUBMB Comments
long-chain-fatty-acyl-ethyl-ester acylhydrolase
The reaction, forms ethyl esters from fatty acids and ethanol in the absence of coenzyme A or ATP. Best substrates are unsaturated octadecanoic acids; palmitate, stearate and arachidonate also act, but more slowly.
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CAS REGISTRY NUMBER
COMMENTARY
90119-16-7
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
cholesteryl oleate + H2O
oleate + cholesterol
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180 kDa high molecular weight protein, only hydrolysis, no synthetic activity for cholesterol oleate
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ir
fatty acid + 2-chloroethanol
fatty acyl 2-chloroethyl ester + H2O
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long-chain fatty acids, 180 kDa high molecular weight protein
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?
monoacylglycerol + H2O
fatty acid + glycerol
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hydrolysis, susceptibilities of substrates increase with decreasing acyl chain length of the fatty acid moiety
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?
oleate + 1-butanol
1-butyl oleate + H2O
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63.2% of the activity with 1-propanol
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?
oleate + 1-propanol
1-propyl oleate + H2O
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highest activity with 1-propanol
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?
oleate + 2-chloroethanol
2-chloroethyl oleate + H2O
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180 kDa high molecular weight protein
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?
triacylglycerol + H2O
?
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hydrolysis, susceptibilities of substrates increase with decreasing acyl chain length of the fatty acid moiety
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?
arachidonate + ethanol
ethyl arachidonate + H2O
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16.7% of the rate with oleate or linoleate
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?
arachidonate + ethanol
ethyl arachidonate + H2O
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50% of the rate with oleate
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?
arachidonate + ethanol
ethyl arachidonate + H2O
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18.3% of the activity with linoleate
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?
cocaine + ethanol
cocaethylene + methanol
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enzyme may be responsible for a portion of cocaethylene synthesis in vivo
product enhances cocaine toxicity
?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
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responsible for the formation of FAEE, which are mediators of ethanol-induced organ damage
?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
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FAEES matabolizes ethanol nonoxidatively in those extrahepatic organs most commonly damaged by alcohol abuse, enzyme may play an important role in alcohol-induced cardiomyopathy
product has potentially toxic effects
?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
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enzyme is present selectively in the organs damaged by ethanol abuse
responsible for the formation of FAEE, which are mediators of ethanol-induced organ damage
?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
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patients with liver or pancreatic disease release FAEE synthase into their plasma permitting nonoxidative ethanol metabolism in the plasma
responsible for the formation of FAEE, which are mediators of ethanol-induced organ damage
?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
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important pathway for the metabolism of ingested ethanol, involved in the metabolism of fatty acids, triglycerides and ethanol
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?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
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nonoxidative ethanol metabolism
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?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
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nonoxidative ethanol metabolism
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?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
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enzyme specificity
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?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
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myocardial nonoxidative ethanol metabolism, metabolism of fatty acids independent of coenzyme A
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?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
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catalyzes fatty acyl ethyl ester synthesis independently of coenzyme A and ATP
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?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
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production of a nonoxidative metabolite of ethanol that accumulates in vivo with potentially toxic effects
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?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
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substrate specificity
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?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
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long-chain fatty acids
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?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
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enzyme contributes to the nonoxidative ethanol metabolism in various organs
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?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
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production of a nonoxidative metabolite of ethanol that accumulates in vivo with potentially toxic effects
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?
linoleate + ethanol
ethyl linoleate + H2O
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65% of the rate with oleate
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?
linoleate + ethanol
ethyl linoleate + H2O
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at the same rate as with oleate
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?
oleate + aniline
oleyl anilide + H2O
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methanol is a better substrate than ethanol and aniline
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?
oleate + aniline
oleyl anilide + H2O
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methanol is a better substrate than ethanol and aniline
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?
oleate + ethanol
ethyl oleate + H2O
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methanol is a better substrate than ethanol and aniline
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?
oleate + ethanol
ethyl oleate + H2O
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ethyl oleate synthesis to hydrolysis ratio of 80:1, at the same rate as with linoleate
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r
oleate + ethanol
ethyl oleate + H2O
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equilibrium data
product accumulates in an organic phase
?
oleate + ethanol
ethyl oleate + H2O
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79.1% of the activity with linoleate, 81.6% of the activity with 1-propanol
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?
oleate + ethanol
ethyl oleate + H2O
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ethyl oleate-hydrolyzing activity is about one-eighth of the synthesizing activity
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r
oleate + ethanol
ethyl oleate + H2O
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methanol is a better substrate than ethanol and aniline
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?
oleate + methanol
methyl oleate + H2O
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methanol is a better substrate than ethanol and aniline
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?
oleate + methanol
methyl oleate + H2O
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74.7% of the activity with 1-propanol
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?
oleate + methanol
methyl oleate + H2O
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methanol is a better substrate than ethanol and aniline
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?
palmitate + ethanol
ethyl palmitate + H2O
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20% of the rate with oleate
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?
palmitate + ethanol
ethyl palmitate + H2O
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12.5% of the rate with oleate or linoleate
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?
palmitate + ethanol
ethyl palmitate + H2O
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synthesis of ethyl palmitate is maximal at 0.2-0.4 mM palmitate
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?
palmitate + ethanol
ethyl palmitate + H2O
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7.3% of the activity with linoleate
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?
stearate + ethanol
ethyl stearate + H2O
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22% of the rate with oleate
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?
stearate + ethanol
ethyl stearate + H2O
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4.2% of the rate with oleate or linoleate
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?
stearate + ethanol
ethyl stearate + H2O
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1.6% of the activity with linoleate
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?
triolein + H2O
?
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hydrolyzes triglycerides, e.g. triolein, 1.25% of the rate of ethyl oleate or ethyl linoleate synthesis
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?
additional information
?
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enzyme has triglyceride lipase activity and also cleaves triglycerides, e.g. triolein, pancreatic fatty acid ethyl ester synthase and triglyceride lipase are likely the same enzymes
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?
additional information
?
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recombinant myocardial FAEES-III has also significant GST activity
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?
additional information
?
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FAEES has no glutathione S-transferase activity towards 1-chloro-2,4-dinitrobenzene and a number of other electrophilic substrates
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?
additional information
?
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enzyme forms: enzyme with FAEES and carboxylesterase activity from heart, structurally different from synthase I and III with GST activity and from synthase II without GST activity
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?
additional information
?
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the enzyme responsible for the fatty acid ethyl ester, fatty acid methyl ester or fatty acid anilide synthesizing activities is most probably carboxylesterase in Hep-G2 cells
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?
additional information
?
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FAEE synthase and carboxylesterase activities in liver and pancreas are possibly due to the same protein, that is, carboxylesterase ES-10, which is responsible for the hydrolysis of ethyl palmitate in liver microsomes
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?
additional information
?
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enzyme contains a specific heparin-binding site
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?
additional information
?
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FAEES-III also catalyzes the glutathione S-transferase reaction
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?
additional information
?
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FAEES-III metabolizes both ethanol and carcinogens
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?
additional information
?
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structural and functional relationship to hepatic microsomal carboxylesterases, low molecular weight FAEE synthase activity most probably is expressed by various isozymes of hepatic microsomal carboxylesterases, which are also involved in the biotransformation of xenobiotic alcohols and amines, the LMW protein fraction also exhibits fatty acid 2-chloroethyl ester synthase and p-nitrophenyl acetate-hydrolyzing activity
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?
additional information
?
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FAEES is associated with carboxylesterase in adipose tissue
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?
additional information
?
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FAEES, 2-chloroethyl ester synthase and carboxylesterase activities are expressed by the same 180 kDa trimeric protein in liver microsomes, structural similarity with rat hepatic microsomal carboxylesterase
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?
additional information
?
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180 kDa high molecular weight protein from liver microsomes, involved in the biosynthesis of long-chain fatty acid esters of xenobiotic alcohols
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?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
cocaine + ethanol
cocaethylene + methanol
-
enzyme may be responsible for a portion of cocaethylene synthesis in vivo
product enhances cocaine toxicity
?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
-
-
responsible for the formation of FAEE, which are mediators of ethanol-induced organ damage
?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
-
FAEES matabolizes ethanol nonoxidatively in those extrahepatic organs most commonly damaged by alcohol abuse, enzyme may play an important role in alcohol-induced cardiomyopathy
product has potentially toxic effects
?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
-
enzyme is present selectively in the organs damaged by ethanol abuse
responsible for the formation of FAEE, which are mediators of ethanol-induced organ damage
?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
-
patients with liver or pancreatic disease release FAEE synthase into their plasma permitting nonoxidative ethanol metabolism in the plasma
responsible for the formation of FAEE, which are mediators of ethanol-induced organ damage
?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
-
important pathway for the metabolism of ingested ethanol, involved in the metabolism of fatty acids, triglycerides and ethanol
-
?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
-
nonoxidative ethanol metabolism
-
?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
-
nonoxidative ethanol metabolism
-
?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
-
myocardial nonoxidative ethanol metabolism, metabolism of fatty acids independent of coenzyme A
-
?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
-
catalyzes fatty acyl ethyl ester synthesis independently of coenzyme A and ATP
-
?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
-
production of a nonoxidative metabolite of ethanol that accumulates in vivo with potentially toxic effects
-
?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
-
enzyme contributes to the nonoxidative ethanol metabolism in various organs
-
?
fatty acid + ethanol
fatty acyl ethyl ester + H2O
-
production of a nonoxidative metabolite of ethanol that accumulates in vivo with potentially toxic effects
-
?
additional information
?
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FAEES-III metabolizes both ethanol and carcinogens
-
-
?
additional information
?
-
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180 kDa high molecular weight protein from liver microsomes, involved in the biosynthesis of long-chain fatty acid esters of xenobiotic alcohols
-
-
?
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
diisopropylfluorophosphate
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0.001 mM, 50% inhibition after 10 min preincubation at 37°C
diisopropylfluorophosphate
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180 kDa high molecular weight protein from liver microsomes
tri-o-tolyl phosphate
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differential inhibition of hepatic, pancreatic and plasma FAEES, no inhibition of pancreatic FAEES activity
tri-o-tolyl phosphate
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inhibits about 95% of the enzyme activity in the liver and whole blood of animals treated with tri-o-tolyl phosphate but no inhibition is observed in the pancreas or brown fat
additional information
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no inhibition of FAEE, FAME or fatty acid anilide synthesizing activities in AR42J cells by tri-o-tolyl phosphate
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additional information
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di-p-tolyl-o-(alpha-hydroxy)tolylphosphate or 2-(o-cresyl)-4H-1:3:2-benzodioxaphosphoran-2-onedoes not inhibit
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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DISEASE
TITLE OF PUBLICATION
LINK TO PUBMED
Carcinoma, Hepatocellular
Differential inhibition of hepatic, pancreatic, and plasma fatty acid ethyl ester synthase by tri-o-tolylphosphate in rats.
Carcinoma, Hepatocellular
Mechanism of differential inhibition of hepatic and pancreatic fatty acid ethyl ester synthase by inhibitors of serine-esterases: in vitro and cell culture studies.
Cardiomyopathies
Mutagenesis and characterization of specific residues in fatty acid ethyl ester synthase: a gene for alcohol-induced cardiomyopathy.
Cardiotoxicity
Rapid fatty acid ethyl ester synthesis by porcine myocardium upon ethanol infusion into the left anterior descending coronary artery.
Fetal Growth Retardation
Association of Fatty Acid Ethyl Esters in Meconium of Neonates with Growth Deficits at Birth: a Prospective, Single-Centre Cohort Study.
Glioma
Nonoxidative ethanol metabolism: expression of fatty acid ethyl ester synthase-III in cultured neural cells.
Hepatoblastoma
The synthesis and secretion of fatty acid ethyl esters from HepG2 cells are stimulated by lipoproteins and albumin.
Hyperlipidemias
?-3 Fatty Acid Ethyl Esters Diminish Postprandial Lipemia in Familial Hypercholesterolemia.
Hypertriglyceridemia
In heavy drinkers fatty acid ethyl esters in the serum are increased for 44 hr after ethanol consumption.
Lung Diseases
Ethanol metabolism, oxidative stress, and endoplasmic reticulum stress responses in the lungs of hepatic alcohol dehydrogenase deficient deer mice after chronic ethanol feeding.
Neoplasms
Alcohol oxidizing enzymes and ethanol-induced cytotoxicity in rat pancreatic acinar AR42J cells.
Neoplasms
Ethanol-induced cytotoxicity in rat pancreatic acinar AR42J cells: role of fatty acid ethyl esters.
Neoplasms
Mechanism of differential inhibition of hepatic and pancreatic fatty acid ethyl ester synthase by inhibitors of serine-esterases: in vitro and cell culture studies.
Neuroblastoma
Nonoxidative ethanol metabolism: expression of fatty acid ethyl ester synthase-III in cultured neural cells.
Obesity
Omega-3 fatty acid ethyl ester supplementation decreases very-low-density lipoprotein triacylglycerol secretion in obese men.
Pancreatic Diseases
Fatty acid ethyl ester synthase, an enzyme for nonoxidative ethanol metabolism, is present in serum after liver and pancreatic injury.
Pancreatitis
Fatty acid ethyl ester synthase inhibition ameliorates ethanol-induced Ca2+-dependent mitochondrial dysfunction and acute pancreatitis.
Pancreatitis
Pancreatic injury in rats induced by fatty acid ethyl ester, a nonoxidative metabolite of alcohol.
Pancreatitis
Pathophysiology and Biomarker Potential of Fatty Acid Ethyl Ester Elevation During Alcoholic Pancreatitis.
Pancreatitis, Acute Necrotizing
Fatty Acid Ethyl Esters Are Less Toxic Than Their Parent Fatty Acids Generated during Acute Pancreatitis.
Pancreatitis, Alcoholic
Pancreatic cholesterol esterase, ES-10, and fatty acid ethyl ester synthase III gene expression are increased in the pancreas and liver but not in the brain or heart with long-term ethanol feeding in rats.
Pancreatitis, Alcoholic
Pathophysiology and Biomarker Potential of Fatty Acid Ethyl Ester Elevation During Alcoholic Pancreatitis.
Pneumonia
Ethanol Exposure Impairs AMPK Signaling and Phagocytosis in Human Alveolar Macrophages: Role of Ethanol Metabolism.
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
additional information
additional information
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thermodynamic parameters relevant to the kinetics and equilibria of the reaction
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0.8
oleate
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pH 7.4, 37°C, 180 kDa high molecular weight protein from liver microsomes
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.285
oleate
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pH 7.4, 37°C, 180 kDa high molecular weight protein from liver microsomes
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
0.0111
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60 kDa low molecular weight protein from liver microsomes with pI 5.3
0.0115
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60 kDa low molecular weight protein from liver microsomes with pI 6.5
0.0125
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60 kDa low molecular weight protein from liver microsomes with pI 5.0
0.0133
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60 kDa low molecular weight protein from liver microsomes with pI 5.6
0.0335
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pH 7.4, 37°C, 180 kDa high molecular weight protein from liver microsomes, FAEES activity
0.035
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60 kDa low molecular weight protein from liver microsomes with pI 5.8
additional information
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
7.2
7.4
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TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
37