BRENDA - Enzyme Database
show all sequences of 5.3.3.5

Steroidomimetic aminomethyl spiroacetals as novel inhibitors of the enzyme DELTA8,7-sterol isomerase in cholesterol biosynthesis

Krojer, M.; Mueller, C.; Bracher, F.; Arch. Pharm. 347, 108-122 (2014)

Data extracted from this reference:

Inhibitors
Inhibitors
Commentary
Organism
Structure
(1'R,3a'R,7a'R,1''R)-5-(N-benzylpiperidin-4-yl)-aminomethyl-7a'-methyl-1'-(1,5-dimethylhexyl)-5-nitrospiro[1,3-dioxane-2,4'-octahydroindene]
-
Homo sapiens
(1'R,3a'R,7a'R,1''R)-5-(N-benzylpiperidin-4-yl)-N-methylaminomethyl-7a'-methyl-1'-(1,5-dimethylhexyl)-5-nitrospiro[1,3-dioxane-2,4'-octahydroindene]
-
Homo sapiens
(1'R,3a'R,7a'R,1''R)-7a'-methyl-1'-(1,5-dimethylhexyl)-5-nitro-5-[[2-(pyrrolidin-1yl)ethyl]aminomethyl]spiro[1,3-dioxane-2,4'-octahydroindene]
-
Homo sapiens
(1'R,3a'R,7a'R,1''R)-7a'-methyl-5-[N-(N,N-dimethylaminoeth-2-yl-aminomethyl)-1'-(1,5-dimethylhexyl)-5-nitrospiro[1,3-dioxane-2,4'-octahydroindene]]
-
Homo sapiens
1',2',3',4'-tetrahydro-5-(N-benzylpiperidin-4-yl)-aminomethyl-5-nitro-6'-(4-methylpentyloxy)-spiro[1,3-dioxane-2,1'-naphthaline]
-
Homo sapiens
1',2',3',4'-tetrahydro-5-(N-benzylpiperidin-4-yl)-aminomethyl-6'-methoxy-5-nitrospiro[1,3-dioxane-2,1'-naphthaline]
-
Homo sapiens
Natural Substrates/ Products (Substrates)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
zymosterol
Homo sapiens
-
cholesta-7,24-dienol
-
-
?
Organism
Organism
UniProt
Commentary
Textmining
Homo sapiens
-
-
-
Substrates and Products (Substrate)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
Substrate Product ID
zymosterol
-
726836
Homo sapiens
cholesta-7,24-dienol
-
-
-
?
Synonyms
Synonyms
Commentary
Organism
3beta-hydroxysteroid DELTA8,7-sterol isomerase
-
Homo sapiens
DELTA8,7-isomerase
-
Homo sapiens
DELTA8,7-sterol isomerase
-
Homo sapiens
EBP
-
Homo sapiens
emopamil-binding protein
-
Homo sapiens
IC50 Value
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.0017
-
pH and temperature not specified in the publication
Homo sapiens
(1'R,3a'R,7a'R,1''R)-5-(N-benzylpiperidin-4-yl)-aminomethyl-7a'-methyl-1'-(1,5-dimethylhexyl)-5-nitrospiro[1,3-dioxane-2,4'-octahydroindene]
0.0045
-
pH and temperature not specified in the publication
Homo sapiens
1',2',3',4'-tetrahydro-5-(N-benzylpiperidin-4-yl)-aminomethyl-5-nitro-6'-(4-methylpentyloxy)-spiro[1,3-dioxane-2,1'-naphthaline]
0.0047
-
pH and temperature not specified in the publication
Homo sapiens
(1'R,3a'R,7a'R,1''R)-5-(N-benzylpiperidin-4-yl)-N-methylaminomethyl-7a'-methyl-1'-(1,5-dimethylhexyl)-5-nitrospiro[1,3-dioxane-2,4'-octahydroindene]
IC50 Value (protein specific)
IC50 Value
IC50 Value Maximum
Commentary
Organism
Inhibitor
Structure
0.0017
-
pH and temperature not specified in the publication
Homo sapiens
(1'R,3a'R,7a'R,1''R)-5-(N-benzylpiperidin-4-yl)-aminomethyl-7a'-methyl-1'-(1,5-dimethylhexyl)-5-nitrospiro[1,3-dioxane-2,4'-octahydroindene]
0.0045
-
pH and temperature not specified in the publication
Homo sapiens
1',2',3',4'-tetrahydro-5-(N-benzylpiperidin-4-yl)-aminomethyl-5-nitro-6'-(4-methylpentyloxy)-spiro[1,3-dioxane-2,1'-naphthaline]
0.0047
-
pH and temperature not specified in the publication
Homo sapiens
(1'R,3a'R,7a'R,1''R)-5-(N-benzylpiperidin-4-yl)-N-methylaminomethyl-7a'-methyl-1'-(1,5-dimethylhexyl)-5-nitrospiro[1,3-dioxane-2,4'-octahydroindene]
Inhibitors (protein specific)
Inhibitors
Commentary
Organism
Structure
(1'R,3a'R,7a'R,1''R)-5-(N-benzylpiperidin-4-yl)-aminomethyl-7a'-methyl-1'-(1,5-dimethylhexyl)-5-nitrospiro[1,3-dioxane-2,4'-octahydroindene]
-
Homo sapiens
(1'R,3a'R,7a'R,1''R)-5-(N-benzylpiperidin-4-yl)-N-methylaminomethyl-7a'-methyl-1'-(1,5-dimethylhexyl)-5-nitrospiro[1,3-dioxane-2,4'-octahydroindene]
-
Homo sapiens
(1'R,3a'R,7a'R,1''R)-7a'-methyl-1'-(1,5-dimethylhexyl)-5-nitro-5-[[2-(pyrrolidin-1yl)ethyl]aminomethyl]spiro[1,3-dioxane-2,4'-octahydroindene]
-
Homo sapiens
(1'R,3a'R,7a'R,1''R)-7a'-methyl-5-[N-(N,N-dimethylaminoeth-2-yl-aminomethyl)-1'-(1,5-dimethylhexyl)-5-nitrospiro[1,3-dioxane-2,4'-octahydroindene]]
-
Homo sapiens
1',2',3',4'-tetrahydro-5-(N-benzylpiperidin-4-yl)-aminomethyl-5-nitro-6'-(4-methylpentyloxy)-spiro[1,3-dioxane-2,1'-naphthaline]
-
Homo sapiens
1',2',3',4'-tetrahydro-5-(N-benzylpiperidin-4-yl)-aminomethyl-6'-methoxy-5-nitrospiro[1,3-dioxane-2,1'-naphthaline]
-
Homo sapiens
Natural Substrates/ Products (Substrates) (protein specific)
Natural Substrates
Organism
Commentary (Nat. Sub.)
Natural Products
Commentary (Nat. Pro.)
Organism (Nat. Pro.)
Reversibility
ID
zymosterol
Homo sapiens
-
cholesta-7,24-dienol
-
-
?
Substrates and Products (Substrate) (protein specific)
Substrates
Commentary Substrates
Literature (Substrates)
Organism
Products
Commentary (Products)
Literature (Products)
Organism (Products)
Reversibility
ID
zymosterol
-
726836
Homo sapiens
cholesta-7,24-dienol
-
-
-
?
Other publictions for EC 5.3.3.5
No.
1st author
Pub Med
title
organims
journal
volume
pages
year
Activating Compound
Application
Cloned(Commentary)
Crystallization (Commentary)
Engineering
General Stability
Inhibitors
KM Value [mM]
Localization
Metals/Ions
Molecular Weight [Da]
Natural Substrates/ Products (Substrates)
Organic Solvent Stability
Organism
Oxidation Stability
Posttranslational Modification
Purification (Commentary)
Reaction
Renatured (Commentary)
Source Tissue
Specific Activity [micromol/min/mg]
Storage Stability
Substrates and Products (Substrate)
Subunits
Synonyms
Temperature Optimum [°C]
Temperature Range [°C]
Temperature Stability [°C]
Turnover Number [1/s]
pH Optimum
pH Range
pH Stability
Cofactor
Ki Value [mM]
pI Value
IC50 Value
Activating Compound (protein specific)
Application (protein specific)
Cloned(Commentary) (protein specific)
Cofactor (protein specific)
Crystallization (Commentary) (protein specific)
Engineering (protein specific)
General Stability (protein specific)
IC50 Value (protein specific)
Inhibitors (protein specific)
Ki Value [mM] (protein specific)
KM Value [mM] (protein specific)
Localization (protein specific)
Metals/Ions (protein specific)
Molecular Weight [Da] (protein specific)
Natural Substrates/ Products (Substrates) (protein specific)
Organic Solvent Stability (protein specific)
Oxidation Stability (protein specific)
Posttranslational Modification (protein specific)
Purification (Commentary) (protein specific)
Renatured (Commentary) (protein specific)
Source Tissue (protein specific)
Specific Activity [micromol/min/mg] (protein specific)
Storage Stability (protein specific)
Substrates and Products (Substrate) (protein specific)
Subunits (protein specific)
Temperature Optimum [°C] (protein specific)
Temperature Range [°C] (protein specific)
Temperature Stability [°C] (protein specific)
Turnover Number [1/s] (protein specific)
pH Optimum (protein specific)
pH Range (protein specific)
pH Stability (protein specific)
pI Value (protein specific)
Expression
General Information
General Information (protein specific)
Expression (protein specific)
KCat/KM [mM/s]
KCat/KM [mM/s] (protein specific)
726836
Krojer
Steroidomimetic aminomethyl sp ...
Homo sapiens
Arch. Pharm.
347
108-122
2014
-
-
-
-
-
-
6
-
-
-
-
1
-
1
-
-
-
-
-
-
-
-
1
-
5
-
-
-
-
-
-
-
-
-
-
3
-
-
-
-
-
-
-
3
6
-
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
727162
Koenig
Stereoselective synthesis of a ...
Saccharomyces cerevisiae, [Candida] glabrata, Yarrowia lipolytica, Homo sapiens
Bioorg. Med. Chem.
21
1925-1943
2013
-
-
-
-
-
-
64
-
-
-
-
8
-
4
-
-
-
-
-
-
-
-
8
-
12
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
64
-
-
-
-
-
8
-
-
-
-
-
-
-
-
8
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
714753
Abate
1-Cyclohexyl-4-(4-arylcyclohex ...
Homo sapiens
ChemMedChem
6
73-80
2011
-
-
-
-
-
-
21
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
18
-
-
-
-
-
-
-
-
-
-
21
18
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
690830
Rahier
Identification of essential am ...
Saccharomyces cerevisiae, Zea mays
Biochem. J.
414
247-259
2008
-
-
1
-
11
-
12
3
-
-
-
-
-
14
-
-
-
-
-
-
-
-
8
-
6
-
-
-
-
-
-
-
-
-
-
10
-
-
1
-
-
11
-
10
12
-
3
-
-
-
-
-
-
-
-
-
-
-
-
8
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
693574
Berardi
Novel 4-(4-aryl)cyclohexyl-1-( ...
Homo sapiens
J. Med. Chem.
51
7523-7531
2008
-
-
-
-
-
-
28
-
-
-
1
-
-
1
-
-
-
-
-
1
-
-
2
-
4
-
-
-
-
-
-
-
-
28
-
-
-
-
-
-
-
-
-
-
28
28
-
-
-
1
-
-
-
-
-
-
1
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
662248
Kedjouar
Molecular characterization of ...
Homo sapiens
J. Biol. Chem.
279
34048-34061
2004
-
-
1
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
649741
Nes
Purification, characterization ...
Homo sapiens
Biochem. J.
367
587-599
2002
-
-
1
-
-
-
6
1
-
-
3
-
-
1
-
-
1
-
-
-
1
1
8
2
-
1
-
-
1
1
-
-
-
6
1
-
-
-
1
-
-
-
-
-
6
6
1
-
-
3
-
-
-
-
1
-
-
1
1
8
2
1
-
-
1
1
-
-
1
-
-
-
-
-
-
649702
Bae
Cholesterol biosynthesis from ...
Rattus norvegicus
Biochem. J.
353
689-699
2001
-
-
1
-
-
-
2
-
-
-
1
1
-
16
-
-
-
-
-
-
-
-
1
1
2
-
-
-
-
-
-
-
-
-
-
2
-
-
1
-
-
-
-
2
2
-
-
-
-
1
1
-
-
-
-
-
-
-
-
1
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
649855
Moebius
Histidine77, glutamic acid81, ...
Homo sapiens
Biochemistry
38
1119-1127
1999
-
-
-
-
69
-
1
-
-
-
-
-
-
9
-
-
-
-
-
-
-
-
-
-
2
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
69
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
653232
Cho
Cholesterol biosynthesis from ...
Rattus norvegicus
Mol. Cells
8
233-239
1998
-
-
-
-
-
-
1
-
1
-
-
-
-
1
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
1
-
-
-
-
-
-
-
1
1
1
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
653279
Moebius
Pharmacological analysis of st ...
Saccharomyces cerevisiae, Mus musculus, Homo sapiens, Cavia porcellus
Mol. Pharmacol.
54
591-598
1998
-
-
-
-
-
-
85
-
-
-
-
-
-
13
-
-
-
-
-
-
-
-
-
-
5
-
-
-
-
-
-
-
-
51
-
18
-
-
-
-
-
-
-
18
85
51
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
653487
Grebenok
Isolation and characterization ...
Arabidopsis thaliana
Plant Mol. Biol.
38
807-815
1998
-
-
1
-
1
-
3
-
1
-
2
-
-
10
-
-
-
-
-
-
-
-
1
2
2
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
3
-
-
1
-
2
-
-
-
-
-
-
-
-
-
1
2
-
-
-
-
-
-
-
-
-
1
1
-
-
-
2985
Scala
The reversibility of the isome ...
Rattus norvegicus
Eur. J. Biochem.
48
263-269
1974
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2983
Lee
Studies on the mechanism of th ...
Rattus norvegicus
J. Biol. Chem.
244
2033-2040
1969
-
-
-
-
-
-
-
-
1
-
-
-
-
1
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
2984
Wilton
The reversibility of the DELTA ...
Rattus norvegicus
Biochem. J.
114
71-73
1969
-
-
-
-
-
-
-
-
1
-
-
-
-
1
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-
1
-
-
-
-
-
-
-
-
1
-
-
1
-
-
-
-
-
-
-
-
-
-
-
-
-
-
-