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Information on EC 3.1.1.13 - sterol esterase and Organism(s) Mus musculus and UniProt Accession Q8BLF1
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3.1.1.13 sterol esteraseIUBMB Comments
A group of enzymes of broad specificity, acting on esters of sterols and long-chain fatty acids, that may also bring about the esterification of sterols. Activated by bile salts.
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Word Map
- 3.1.1.13
-
cessation
- women
- lipoprotein
- triglyceride
- children
-
smoke
-
social
-
smoking
-
services
- infant
- milk
- arterial
- birth
-
proliferate
-
decision
- pain
-
physician
- atherosclerosis
-
discharge
-
awareness
-
policy
- oleate
-
psychological
-
australia
-
fire
-
foam
-
esterify
- lipases
-
advice
-
firing
-
quit
-
professionals
-
financial
-
abstinence
- nurses
-
practitioner
-
doctor
-
legal
- hepatomegaly
-
breastfeeding
-
hepatosplenomegaly
-
profession
-
moral
-
acyl-coa:cholesterol
-
political
- triolein
-
a:cholesterol
-
semi-structured
-
unesterified
- nutrition
- paper production
- analysis
- diagnostics
- medicine
-
violence
The taxonomic range for the selected organisms is: Mus musculus
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
cease, lysosomal acid lipase, cholesterol ester hydrolase, cholesteryl ester hydrolase, pancreatic cholesterol esterase, bile salt-stimulated lipase, cholesteryl esterase, neutral cholesteryl ester hydrolase, nceh1, kiaa1363, 
more
topSYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
NCEH
Acid cholesteryl ester hydrolase
-
-
-
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acylcholesterol lipase
-
-
-
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cholesterase
-
-
-
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cholesterol ester hydrolase
-
-
-
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cholesterol ester synthetase
-
-
-
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cholesterol esterase
cholesteryl ester hydrolase
cholesteryl ester synthetase
-
-
-
-
cholesteryl esterase
-
-
-
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LAL
sterol ester hydrolase
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-
-
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Sterol esterase
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-
-
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sterol-ester acylhydrolase
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-
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triterpenol esterase
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-
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cholesterol esterase
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-
-
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cholesteryl ester hydrolase
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-
-
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LAL
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a steryl ester + H2O = a sterol + a fatty acid
a group of enzymes of broad specificity, acting on esters of sterols and long-chain fatty acids, that may also bring about the esterification of sterols. Activated by bile salts
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
esterification
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-
-
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hydrolysis of carboxylic ester
hydrolysis of carboxylic ester
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-
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SYSTEMATIC NAME
IUBMB Comments
steryl-ester acylhydrolase
A group of enzymes of broad specificity, acting on esters of sterols and long-chain fatty acids, that may also bring about the esterification of sterols. Activated by bile salts.
CAS REGISTRY NUMBER
COMMENTARY
9026-00-0
-
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
4-methylumbelliferyl butyrate + H2O
4-methylumbelliferol + butyrate
-
-
-
?
cholesteryl esters + H2O
cholesterol + fatty acid
-
involvement in arteriosclerosis
-
r
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
cholesteryl esters + H2O
cholesterol + fatty acid
-
involvement in arteriosclerosis
-
r
COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
Mg2+
-
activation in a reaction mixture containing cAMP, protein kinase A and ATP
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
2-(dimethylamino)-5,6,7,8-tetrahydro-4H-[1]benzothieno[2,3-d][1,3]oxazin-4-one
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2-(dimethylamino)-6,7-dihydro-4H,5H-cyclopenta[4,5]thieno[2,3-d][1,3]oxazin-4-one
-
4-[3,5-bis(trifluoromethyl)phenyl]-N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]piperazine-1-carboxamide
95.3% activity compared to control, at 0.025 mM
N-(3,5-dichlorophenyl)-N'-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]urea
100% activity compared to control, at 0.025 mM
N-(3,5-difluorophenyl)-N'-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]urea
88.4% activity compared to control, at 0.025 mM
N-(3,5-dimethoxyphenyl)-N'-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]urea
103% activity compared to control, at 0.025 mM
N-(3,5-dimethylphenyl)-N'-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]urea
94.7% activity compared to control, at 0.025 mM
N-(3,5-dinitrophenyl)-N'-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]urea
85.3% activity compared to control, at 0.025 mM
N-(4-bromophenyl)-N'-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]urea
94.5% activity compared to control, at 0.025 mM
N-(4-chlorophenyl)-N'-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]urea
64.0% activity compared to control, at 0.025 mM
N-[3',5'-bis(trifluoromethyl)[1,1'-biphenyl]-2-yl]-N'-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]urea
87.8% activity compared to control, at 0.025 mM
N-[3',5'-bis(trifluoromethyl)[1,1'-biphenyl]-3-yl]-N'-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]urea
73.5% activity compared to control, at 0.025 mM
N-[3',5'-bis(trifluoromethyl)[1,1'-biphenyl]-4-yl]-N'-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]urea
58.2% activity compared to control, at 0.025 mM
N-[3,5-bis(trifluoromethyl)phenyl]-N'-[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]urea
108% activity compared to control, at 0.025 mM
N-[3,5-bis(trifluoromethyl)phenyl]-N'-[3-(1,3-dioxo-1,3,4,5,6,7-hexahydro-2H-isoindol-2-yl)propyl]urea
71.0% activity compared to control, at 0.025 mM
N-[3,5-bis(trifluoromethyl)phenyl]-N'-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]urea
5.25% activity compared to control, at 0.025 mM
N-[3,5-bis(trifluoromethyl)phenyl]-N'-[3-[(3aR,4S,7R,7aS)-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-4,7-methanoisoindol-2-yl]propyl]urea
96.6% activity compared to control, at 0.025 mM
N-[3,5-bis(trifluoromethyl)phenyl]-N'-[3-[(3aR,7aS)-1,3-dioxo-1,3,3a,4,7,7a-hexahydro-2H-isoindol-2-yl]propyl]urea
82.9% activity compared to control, at 0.025 mM
N-[3,5-bis(trifluoromethyl)phenyl]-N'-[3-[(3aR,7aS)-1,3-dioxooctahydro-2H-isoindol-2-yl]propyl]urea
89.1% activity compared to control, at 0.025 mM
N-[3,5-bis(trifluoromethyl)phenyl]-N'-[4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butyl]urea
15.6% activity compared to control, at 0.025 mM
N-[3,5-bis(trifluoromethyl)phenyl]-N'-[5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pentyl]urea
22.5% activity compared to control, at 0.025 mM
N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-4-phenylpiperazine-1-carboxamide
101% activity compared to control, at 0.025 mM
N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-N'-(4-fluorophenyl)urea
101% activity compared to control, at 0.025 mM
N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-N'-(4-methoxyphenyl)urea
90.4% activity compared to control, at 0.025 mM
N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-N'-(4-methylphenyl)urea
100% activity compared to control, at 0.025 mM
N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-N'-(4-nitrophenyl)urea
76.5% activity compared to control, at 0.025 mM
N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-N'-phenylurea
107% activity compared to control, at 0.025 mM
N-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]-N'-[4-(trifluoromethyl)phenyl]urea
92.5% activity compared to control, at 0.025 mM
N-[3,5-bis(trifluoromethyl)phenyl]-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pentanamide
71.8% activity compared to control, at 0.025 mM
N-[3,5-bis(trifluoromethyl)phenyl]-5-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)pentanamide
90.8% activity compared to control, at 0.025 mM
additional information
omega-phthalimidoalkyl aryl ureas as potent and selective inhibitors of cholesterol esterase, synthesis and inhibitory potencies. The urea motif with an attached 3,5-bis(trifluoromethyl)phenyl group and the aromatic character of the omega-phthalimide residue are most important for inhibitory activity. In addition, an alkyl chain composed of three or four methylene groups, connecting the urea and phthalimide moieties, is an optimal spacer for inhibitors, Structure-activity relationships depending on the spacer length and urea/amide motif, overview
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
NaCl
the nCEH activity in the whole cell lysates from NCEH-transfected cells is slightly stimulated by low concentrations of NaCl (6.5% at 0.05 M)
17beta-estradiol
-
enhanced hydrolysis of cholesteryl oleate in time- and dose-dependent manner
cAMP-dependent protein kinase type II
-
increasing activity on cholesteryl oleate hydrolysis, increasing protein kinase synthesis due to addition of 17beta-estradiol
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.000262
2-(dimethylamino)-5,6,7,8-tetrahydro-4H-[1]benzothieno[2,3-d][1,3]oxazin-4-one
pH 7.0, 30°C, recombinant enzyme
0.0000341
2-(dimethylamino)-6,7-dihydro-4H,5H-cyclopenta[4,5]thieno[2,3-d][1,3]oxazin-4-one
pH 7.0, 30°C, recombinant enzyme
0.00119
N-[3,5-bis(trifluoromethyl)phenyl]-N'-[3-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)propyl]urea
pH 7.0, 30°C, recombinant enzyme
0.0187
N-[3,5-bis(trifluoromethyl)phenyl]-N'-[4-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)butyl]urea
pH 7.0, 30°C, recombinant enzyme
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
physiological function
the enzyme plays a dominant role over hormone-sensitive lipase in the hydrolysis of cholesteryl ester and subsequent cholesterol efflux in mouse peritoneal macrophages
malfunction
physiological function
malfunction
-
hormone-sensitive lipase deficiency remarkably reduces the neutral cholesterol ester hydrolase activity in adrenal glands. Abrogation of neutral cholesterol ester hydrolytic activity causes adrenal enlargement
malfunction
-
neutral cholesterol ester hydrolase 1/hormone-sensitive lipase-deficient mice develop atherosclerosis faster than the control and single deficient bone marrow recipients
physiological function
-
Nceh1 is involved in the adrenal cholesterol metabolism, and the cholesterol ester hydrolytic activity in adrenal glands is associated with the organ enlargement
physiological function
-
neutral cholesterol ester hydrolase 1 protects against foam cell formation and atherosclerosis
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant C-terminally double-StrepII-tagged enzyme from HEK-293 EBNA cells by affinity chromatography
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
recombinant expression of C-terminally double-StrepII-tagged enzyme in HEK-293 EBNA cells
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
enzyme activity is increased 24.9fold by overexpression of hormone-sensitive lipase
APPLICATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
medicine
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LAL plays a essential role in development, homeostasis, and function of T cells, LAL deficiency impairs T cell development in the thymus
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Tomita, T.; Sawamura, F.; Uetsuka, R.; Chiba, T.; Miura, S.; Ikeda, M.; Tomita, I.
Inhibition of cholesterylester accumulation by 17beta-estradiol in macrophages through activation of neutral cholesterol esterase
Biochim. Biophys. Acta
1300
210-218
1996
Mus musculus
Fresnedo, O.; De Heredia, M.L.; Martinez, M.J.; Cristobal, S.; Rejas, M.T.; Cuezva, J.M.; Ochoa, B.
Immunolocalization of a novel cholesteryl ester hydrolase in the endoplasmic reticulum of murine and human hepatocytes
Hepatology
33
662-667
2001
Homo sapiens, Mus musculus, Rattus norvegicus
Qu, P.; Du, H.; Wilkes, D.S.; Yan, C.
Critical roles of lysosomal acid lipase in T cell development and function
Am. J. Pathol.
174
944-956
2009
Mus musculus
Okazaki, H.; Igarashi, M.; Nishi, M.; Sekiya, M.; Tajima, M.; Takase, S.; Takanashi, M.; Ohta, K.; Tamura, Y.; Okazaki, S.; Yahagi, N.; Ohashi, K.; Amemiya-Kudo, M.; Nakagawa, Y.; Nagai, R.; Kadowaki, T.; Osuga, J.; Ishibashi, S.
Identification of neutral cholesterol ester hydrolase, a key enzyme removing cholesterol from macrophages
J. Biol. Chem.
283
33357-33364
2008
Homo sapiens, Mus musculus (Q8BLF1), Mus musculus
Ohta, K.; Sekiya, M.; Uozaki, H.; Igarashi, M.; Takase, S.; Kumagai, M.; Takanashi, M.; Takeuchi, Y.; Izumida, Y.; Kubota, M.; Nishi, M.; Okazaki, H.; Iizuka, Y.; Yahagi, N.; Yagyu, H.; Fukayama, M.; Kadowaki, T.; Ohashi, K.; Ishibashi, S.; Osuga, J.
Abrogation of neutral cholesterol ester hydrolytic activity causes adrenal enlargement
Biochem. Biophys. Res. Commun.
404
254-260
2011
Mus musculus
Sekiya, M.; Osuga, J.; Igarashi, M.; Okazaki, H.; Ishibashi, S.
The role of neutral cholesterol ester hydrolysis in macrophage foam cells
J. Artheroscler. Thromb.
18
359-364
2011
Homo sapiens, Mus musculus
Sakai, K.; Igarashi, M.; Yamamuro, D.; Ohshiro, T.; Nagashima, S.; Takahashi, M.; Enkhtuvshin, B.; Sekiya, M.; Okazak, H.; Osuga, J.I.; Ishibashi, S.
Critical role of neutral cholesteryl ester hydrolase 1 in cholesteryl ester hydrolysis in murine macrophages
J. Lipid Res.
55
2033-2040
2014
Mus musculus (Q8BLF1), Mus musculus
Dato, F.M.; Sheikh, M.; Uhl, R.Z.; Schueller, A.W.; Steinkrueger, M.; Koch, P.; Neudoerfl, J.M.; Guetschow, M.; Goldfuss, B.; Pietsch, M.
omega-Phthalimidoalkyl aryl ureas as potent and selective inhibitors of cholesterol esterase
ChemMedChem
13
1833-1847
2018
Homo sapiens (P19835), Mus musculus (Q64285)
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