Information on EC 2.5.1.21 - squalene synthase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
2.5.1.21
-
RECOMMENDED NAME
GeneOntology No.
squalene synthase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
2 (2E,6E)-farnesyl diphosphate + NAD(P)H + H+ = squalene + 2 diphosphate + NAD(P)+
show the reaction diagram
2 (2E,6E)-farnesyl diphosphate = diphosphate + presqualene diphosphate
show the reaction diagram
; 1a
-
-
-
presqualene diphosphate + NAD(P)H + H+ = squalene + diphosphate + NAD(P)+
show the reaction diagram
; 1b
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-
-
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
alkenyl group transfer
-
-
-
-
reduction
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of antibiotics
-
-
Biosynthesis of secondary metabolites
-
-
cholesterol biosynthesis
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-
epoxysqualene biosynthesis
-
-
Metabolic pathways
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-
Sesquiterpenoid and triterpenoid biosynthesis
-
-
Steroid biosynthesis
-
-
SYSTEMATIC NAME
IUBMB Comments
(2E,6E)-farnesyl-diphosphate:(2E,6E)-farnesyl-diphosphate farnesyltransferase
This microsomal enzyme catalyses the first committed step in the biosynthesis of sterols. The enzyme from yeast requires either Mg2+ or Mn2+ for activity. In the absence of NAD(P)H, presqualene diphosphate (PSPP) is accumulated. When NAD(P)H is present, presqualene diphosphate does not dissociate from the enzyme during the synthesis of squalene from farnesyl diphosphate (FPP) [8]. High concentrations of FPP inhibit the production of squalene but not of PSPP [8].
CAS REGISTRY NUMBER
COMMENTARY hide
9077-14-9
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
green microalga, race B
SwissProt
Manually annotated by BRENDA team
gene BfSS1
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
gene CbSqS
UniProt
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
Uniprot
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
licorice
-
-
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
Leishmania donovani MHOM/IN/80/Dd8
-
UniProt
Manually annotated by BRENDA team
recombinant enzyme
-
-
Manually annotated by BRENDA team
-
Swissprot
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
daffodil
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-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
gene PSS1; clone 8380-1
UniProt
Manually annotated by BRENDA team
gene PSS1; clone 8380-1
UniProt
Manually annotated by BRENDA team
-
UniProt
Manually annotated by BRENDA team
strain BP-1
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-
Manually annotated by BRENDA team
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
additional information
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2E,6E)-3,7,10-trimethylundeca-2,6-dienyl diphosphate + NADPH
diphosphate + ?
show the reaction diagram
-
weak
-
-
?
(2E,6E)-3,7,11-trimethyldodeca-2,6-dienyl diphosphate + NADPH
diphosphate + ?
show the reaction diagram
-
-
-
-
?
(2E,6E)-3,7,12-trimethyltrideca-2,6-dienyl diphosphate + NADPH
diphosphate + ?
show the reaction diagram
-
weak
-
-
?
(2E,6E)-3,7-dimethyldodeca-2,6-dienyl diphosphate + NADPH
diphosphate + ?
show the reaction diagram
-
-
-
-
?
(2E,6E)-3,7-dimethyltetradeca-2,6-dienyl diphosphate + NADPH
diphosphate + ?
show the reaction diagram
-
weak
-
-
?
(2E,6E)-3,7-dimethyltrideca-2,6-dienyl diphosphate + NADPH
diphosphate + ?
show the reaction diagram
-
weak
-
-
?
(2E,6E)-3,7-dimethylundeca-2,6-dienyl diphosphate + NADPH
diphosphate + ?
show the reaction diagram
-
weak
-
-
?
(E,E)-7-desmethylfarnesyl diphosphate + NADPH
6,19-didesmethylsqualene + NADP+ + diphosphate
show the reaction diagram
-
at 60% of the efficiency that farnesyl diphosphate is converted to squalene
in absence of farnesyl diphosphate, 6-desmethylsqualene is produced in presence of farnesyl diphosphate
?
10,11-dihydrofarnesyl diphosphate + NADPH
2,3,22,23-tetrahydrosqualene + NADP+ + diphosphate
show the reaction diagram
-
at 60% of the efficiency that farnesyl diphosphate is converted to squalene
-
?
2 (2E,6E)-farnesyl diphosphate
diphosphate + presqualene diphosphate
show the reaction diagram
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
show the reaction diagram
2 farnesyl diphosphate
presqualene diphosphate + diphosphate
show the reaction diagram
2-methylfarnesyl diphosphate + NADPH
11-methylsqualene + NADP+ + diphosphate
show the reaction diagram
3-demethylfarnesyl diphosphate + NADPH
10-demethylsqualene + NADP+ + diphosphate
show the reaction diagram
farnesyl diphosphate
12,13-cis-dehydrosqualene + diphosphate
show the reaction diagram
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
show the reaction diagram
farnesyl diphosphate + NAD(P)H
squalene + diphosphate + NAD(P)+
show the reaction diagram
farnesyl diphosphate + NAD(P)H + H+
squalene + diphosphate + NAD(P)+
show the reaction diagram
farnesyl diphosphate + NADPH + H+
squalene + diphosphate + NADP+
show the reaction diagram
-
-
sole product
-
?
geranylgeranyl diphosphate + geranylgeranyl diphosphate
prelycopersene diphosphate + diphosphate
show the reaction diagram
-
-
-
?
geranylgeranyl diphosphate + NAD(P)H
lycopersene + NAD(P)+ + diphosphate
show the reaction diagram
-
-
-
?
presqualene diphosphate + NAD(P)H
squalene + NAD(P)+ + diphosphate
show the reaction diagram
presqualene diphosphate + NAD(P)H + H+
squalene + diphosphate + NAD(P)+
show the reaction diagram
presqualene diphosphate + NADPH + H+
squalene + diphosphate + NADP+
show the reaction diagram
additional information
?
-
NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
2 (2E,6E)-farnesyl diphosphate
diphosphate + presqualene diphosphate
show the reaction diagram
H9L9T8
-
-
-
?
2 (2E,6E)-farnesyl diphosphate + NADPH + H+
squalene + 2 diphosphate + NADP+
show the reaction diagram
2 farnesyl diphosphate
presqualene diphosphate + diphosphate
show the reaction diagram
farnesyl diphosphate + farnesyl diphosphate
diphosphate + presqualene diphosphate
show the reaction diagram
presqualene diphosphate + NAD(P)H + H+
squalene + diphosphate + NAD(P)+
show the reaction diagram
presqualene diphosphate + NADPH + H+
squalene + diphosphate + NADP+
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NAD(P)H
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(1-[[(1R,5S)-7-chloro-5-(2-chlorophenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetyl]piperidin-4-yl)acetic acid
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-
(1-[[(3R,5S)-1-[3-(acetyloxy)-2,2-dimethylpropyl]-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]piperidin-4-yl)acetic acid
(1-[[(3R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]piperidin-4-yl)acetic acid
-
-
(1-[[(6S)-8-chloro-6-(2,3-dimethoxyphenyl)-1-(propan-2-yl)-6,10b-dihydro-1H,4H-[2]benzoxepino[4,5-c][1,2]oxazol-4-yl]acetyl]piperidin-4-yl)acetic acid
-
-
(1R,5S)-7-chloro-5-(2-methoxyphenyl)-1-(2-methylpropyl)-3-[2-oxo-2-(piperidin-1-yl)ethyl]-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one
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-
(2E)-3-[(1R,5S)-3-(carboxymethyl)-7-chloro-5-(2-chlorophenyl)-2-oxo-2,3,4,5-tetrahydro-1H-3-benzazepin-1-yl]-2-methylprop-2-enoic acid
-
-
(3R)-3-[[3-(benzyloxy)phenyl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol
-
IC50: 1500 nM
(3S)-1-(3-((4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl)propanoyl)-3-piperidine carboxylic acid
-
-
(3S)-1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]-3-piperidinecarboxylic acid
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-
1,3-diallyl-2-[3-(isopropylamino)propoxy]-9H-carbazole
-
50% inhibition at 250 nM
1-(2-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-2H-1,2,3,4-tetrazol-5-yl)cyclopropanecarboxylic acid
-
-
1-(3-((4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl)propanoyl)-3-azetidine carboxylic acid
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-
1-allyl-2-(3-anilinopropoxy)-9H-carbazole
-
50% inhibition at above 0.001 mM nM
1-allyl-2-[3-(benzylamino)propoxy]-9H-carbazole
-
50% inhibition at 63 nM
1-allyl-2-[3-(benzylamino)propoxy]-9H-carbazole hydrochloride
-
50% inhibition at 150 nM
1-allyl-2-[3-(cyclohexylamino)propoxy]-9H-carbazole
-
50% inhibition at 310 nM
1-allyl-2-[3-(cyclopropylamino)propoxy]-9H-carbazole
-
50% inhibition at 230 nM
1-allyl-2-[3-(isobutylamino)propoxy]-9H-carbazole
-
50% inhibition at 400 nM
1-allyl-2-[3-(isopropylamino)propoxy]-9H-carbazole
1-allyl-2-[3-(isopropylamino)propoxy]-9H-xanthen-9-one
1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]-4-piperidinecarboxylic acid
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-
1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-1,2,3-triazole-4-carboxylic acid
-
-
1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-pyrazole-4-carboxylic acid
-
-
1-[[(1R,5R)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetyl]piperidine-4-carboxylic acid
-
-
1-[[(1R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetyl]piperidine-4-carboxylic acid
-
-
1-[[(1R,5S)-7-chloro-5-(2-chlorophenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetyl]piperidine-4-carboxylic acid
-
-
1-[[(1R,5S)-7-chloro-5-(2-methoxyphenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetyl]piperidine-4-carboxylic acid
-
-
1-[[(1S,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetyl]piperidine-4-carboxylic acid
-
-
1-[[(6S)-8-chloro-6-(2,3-dimethoxyphenyl)-1-(propan-2-yl)-6,10b-dihydro-1H,4H-[2]benzoxepino[4,5-c][1,2]oxazol-4-yl]acetyl]piperidine-4-carboxylic acid
-
-
2-(1-(3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propanoyl)-3-azetidinyl)acetic acid
-
-
2-(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]-4-piperidinyl)acetic acid
-
-
2-(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-1,2,3-triazol-4-yl)acetic acid
-
-
2-(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-1,2,3-triazol-5-yl)acetic acid
-
-
2-(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-pyrazol-3-yl)acetic acid
-
-
2-(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-pyrazol-4-yl)acetic acid
-
-
2-(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-pyrazol-5-yl)acetic acid
-
-
2-(1-[2-[(4S,6R)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]-4-piperidinyl)acetic acid
-
-
2-(1-[2-[8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]-4-piperidinyl)acetic acid
-
-
2-(1-[3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propanoyl]-4-piperidinyl)acetic acid
-
-
2-(2-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl)ethyl]-2H-1,2,3,4-tetrazol-5-yl]-2-methylpropanoic acid
-
-
2-(2-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl)ethyl]-2H-1,2,3,4-tetrazol-5-yl]acetic acid
-
-
2-(2-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-1,2,3,4-tetrazol-5-yl)acetic acid
-
-
2-(4-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]-1-piperazinyl)acetic acid
-
-
2-(4-[3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propanoyl]-2-oxo-1-piperazinyl)acetic acid
-
-
2-([2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]amino)acetic acid
-
-
2-[(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-1,2,3-triazol-4-yl)methoxy]-2-ethylbutanoic acid
-
-
2-[(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-1,2,3-triazol-4-yl)methoxy]-2-methylpropanoic acid
-
-
2-[(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-1,2,3-triazol-4-yl)methoxy]acetic acid
-
-
2-[(1-[3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propanoyl]-4-piperidinyl)methoxy]acetic acid
-
-
2-[(1-[3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propanoyl]-4-piperidinyl)oxy]acetic acid
-
-
2-[(2-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-2H-1,2,3,4-tetrazol-5-yl)methoxy]-2-methylpropanoic acid
-
-
2-[(6S)-8-chloro-6-(2,3-dimethoxyphenyl)-1-(propan-2-yl)-6,10b-dihydro-1H,4H-[2]benzoxepino[4,5-c][1,2]oxazol-4-yl]-1-[(3R)-3-hydroxypyrrolidin-1-yl]ethanone
-
-
2-[1,8-dichloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetic acid
-
-
2-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-2H-1,2,3,4-tetrazol-5-carboxylic acid
-
-
2-[3-(isopropylamino)propoxy]-1-ethyl-9H-carbazole
-
50% inhibition at 460 nM
2-[3-(isopropylamino)propoxy]-9H-carbazole
2-[8-chloro-6-(1-naphthyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetic acid
-
-
2-[8-chloro-6-(2,3-dichlorobenzoyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetic acid
-
-
2-[8-chloro-6-(2,3-dihydro-1,4-benzodioxin-5-yl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetic acid
-
-
2-[8-chloro-6-(2,3-dimethoxyphenyl)-1-(4-morpholinylmethyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetic acid
-
-
2-[8-chloro-6-(2,3-dimethoxyphenyl)-1-[(dimethylamino)methyl]-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetic acid
-
-
2-[8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetic acid
-
-
2-[[(2Z)-2-(1-azabicyclo(2.2.2)oct-3-ylidene)-2-fluoroethyl]oxy]-9H-carbazole
-
i.e. YM-53601, 50% inhibition at 90 nM
3-(2-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-2H-1,2,3,4-tetrazol-5-yl)propanoic acid
-
-
3-(4-quinolin-6-ylphenyl)quinuclidin-3-ol
3-(biphenyl-4-yl)-2,3-dehydroquinuclidine
-
50% inhibition at 243 nM
3-(biphenyl-4-yl)-3-hydroxyquinuclidine
-
50% inhibition at 13 nM
3-(biphenyl-4-yl)-4'[(t-butyldimethylsilyl)oxy]-3-hydroxyquinuclidine
-
50% inhibition above 0.001 mM
3-(biphenyl-4-yl-4'-hydroxy)-2,3-dehydroquinuclidine
-
50% inhibition at 96 nM
3-(biphenyl-4-ylmethyl)-1-azabicyclo[2.2.2]oct-2-ene
-
IC50: 730 nM
3-([2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]amino)benzoic acid
-
-
3-([2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]amino)propionic acid
-
-
3-C-carboxy-2,4-dideoxy-2-dodec-11-en-1-ylpentaric acid
-
-
3-C-carboxy-2,4-dideoxy-2-dodecylpentaric acid
-
-
3-[(1-[3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propanoyl]-4-piperidinyl)oxy]propanoic acid
-
-
3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6Hpyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propionic acid
-
-
3-[[4-(benzyloxy)phenyl]ethynyl]-1-azabicyclo[2.2.2]oct-2-ene
-
IC50: 830 nM
4-[3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propanoyl]-2-morpholine carboxylic acid
-
-
6-([[(1R,5S)-7-chloro-5-(2-chlorophenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetyl]amino)hexanoic acid
-
-
Ammonium analogues
-
overview
-
atorvastatin
-
-
BMS 187745
-
decrease of cholesterol or LDL
BMS-187745
-
-
BMS-188494
chlorogenic acid
-
-
CP-294838
a benzoxazepinone IC50 130 nM
CP-295697
a bisphosphonate, IC50: 20 nM
deoxycholate
-
-
E5700
-
IC50: 0.84 nM
EP2302
EP2306
ER-27856
ER-28448
ER119884
-
IC50: 3.52 nM
ethyl 4-(1-azabicyclo[2.2.2]oct-2-en-3-yl)benzoate
-
IC50: 50 nM
ethyl [(1R,5S)-7-chloro-5-(2-chlorophenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetate
-
-
farnesyl diphosphate
fenofibrate
-
-
Guanidinium chloride
loss of 86% activity at 0.3M GdmCl, 50% at 0.2 M
lapaquistat
methyl 2-[8-chloro-6-(2,3-dimethoxyphenyl)-4H,6Hpyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetate
-
-
Mg2+
-
above 35 mM
N-ethylmaleimide
-
-
N-isopropyl-biphenyloxypropylamine
-
50% inhibition at 93 nM
N-[[(3R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(2,2-dimethylpropyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]-L-aspartic acid
-
-
NADP+
-
inhibitor of squalene synthesis
RPR107393
simvastatin
-
-
squalestatin
T-91485
-
-
TAK-475
Urea
loss of 81% activity at 2 M, 50% at 1 M
YM-53601
zaragozic acid
zaragozic acid A
[(1R,5R)-7-chloro-1-(2-methylpropyl)-2-oxo-5-phenyl-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
-
-
[(1R,5S)-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
-
-
[(1R,5S)-5-(2-bromophenyl)-7-chloro-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
-
-
[(1R,5S)-5-(2-chlorophenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
-
-
[(1R,5S)-5-(2-chlorophenyl)-7-fluoro-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
-
-
[(1R,5S)-5-(2-chlorophenyl)-7-methyl-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
-
-
[(1R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
-
-
[(1R,5S)-7-chloro-5-(2-chlorophenyl)-1-(2-hydroxy-2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
-
-
[(1R,5S)-7-chloro-5-(2-chlorophenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
-
-
[(1R,5S)-7-chloro-5-(2-methoxyphenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
-
-
[(4R,6R)-8-chloro-6-(2,3-dimethoxyphenyl)-1-(propan-2-yl)-6,10b-dihydro-1H,4H-[2]benzoxepino[4,5-c][1,2]oxazol-4-yl]acetic acid
-
-
[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-1-(propan-2-yl)-6,10b-dihydro-1H,4H-[2]benzoxepino[4,5-c][1,2]oxazol-4-yl]acetic acid
-
-
[(4S,6R)-8-chloro-6-(2,3-dimethoxyphenyl)-1-(propan-2-yl)-6,10b-dihydro-1H,4H-[2]benzoxepino[4,5-c][1,2]oxazol-4-yl]acetic acid
-
-
[(4S,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-1-(propan-2-yl)-6,10b-dihydro-1H,4H-[2]benzoxepino[4,5-c][1,2]oxazol-4-yl]acetic acid
-
-
[(6S)-8-chloro-6-(2,3-dimethoxyphenyl)-1-(propan-2-yl)-6,10b-dihydro-1H,4H-[2]benzoxepino[4,5-c][1,2]oxazol-4-yl]acetic acid
-
-
additional information
ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
bovine serum albumin
-
activates recombinant enzyme
-
Tween 20
-
stimulates recombinant enzyme
Tween 40
-
stimulates recombinant enzyme
Tween 80
W-1
-
detergent, stimulates recombinant enzyme
-
additional information
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0038
(2E,6E)-farnesyl diphosphate
pH 7.4, 37C
0.0004 - 0.0095
farnesyl diphosphate
0.004 - 3.6
NADH
0.02334 - 0.5
NADPH
0.001
trans-farnesyl diphosphate
-
cosubstrate NADPH
additional information
additional information
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.53 - 3.3
farnesyl diphosphate
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00000025
zaragozic acid
-
-
-
0.000074
zaragozic acid A
pH 7.4, 37C
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0014
(1-[[(1R,5S)-7-chloro-5-(2-chlorophenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetyl]piperidin-4-yl)acetic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.000213
(1-[[(3R,5S)-1-[3-(acetyloxy)-2,2-dimethylpropyl]-7-chloro-5-(2,3-dimethoxyphenyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]piperidin-4-yl)acetic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.00026
(1-[[(3R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(3-hydroxy-2,2-dimethylpropyl)-2-oxo-1,2,3,5-tetrahydro-4,1-benzoxazepin-3-yl]acetyl]piperidin-4-yl)acetic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.000131
(1-[[(6S)-8-chloro-6-(2,3-dimethoxyphenyl)-1-(propan-2-yl)-6,10b-dihydro-1H,4H-[2]benzoxepino[4,5-c][1,2]oxazol-4-yl]acetyl]piperidin-4-yl)acetic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.00037
(1R,5S)-7-chloro-5-(2-methoxyphenyl)-1-(2-methylpropyl)-3-[2-oxo-2-(piperidin-1-yl)ethyl]-1,3,4,5-tetrahydro-2H-3-benzazepin-2-one
Homo sapiens
-
pH and temperature not specified in the publication
0.0055
(2E)-3-[(1R,5S)-3-(carboxymethyl)-7-chloro-5-(2-chlorophenyl)-2-oxo-2,3,4,5-tetrahydro-1H-3-benzazepin-1-yl]-2-methylprop-2-enoic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.0015
(3R)-3-[[3-(benzyloxy)phenyl]ethynyl]-1-azabicyclo[2.2.2]octan-3-ol
Trypanosoma cruzi
-
IC50: 1500 nM
0.0000014
(3S)-1-(3-((4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl)propanoyl)-3-piperidine carboxylic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000023
(3S)-1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]-3-piperidinecarboxylic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000017
1-(2-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-2H-1,2,3,4-tetrazol-5-yl)cyclopropanecarboxylic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000022
1-(3-((4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl)propanoyl)-3-azetidine carboxylic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000034
1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]-4-piperidinecarboxylic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.00000059
1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-1,2,3-triazole-4-carboxylic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000021
1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-pyrazole-4-carboxylic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.00022
1-[[(1R,5R)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetyl]piperidine-4-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.00045
1-[[(1R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetyl]piperidine-4-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.00093
1-[[(1R,5S)-7-chloro-5-(2-chlorophenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetyl]piperidine-4-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.0005
1-[[(1R,5S)-7-chloro-5-(2-methoxyphenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetyl]piperidine-4-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.02
1-[[(1S,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetyl]piperidine-4-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.000112
1-[[(6S)-8-chloro-6-(2,3-dimethoxyphenyl)-1-(propan-2-yl)-6,10b-dihydro-1H,4H-[2]benzoxepino[4,5-c][1,2]oxazol-4-yl]acetyl]piperidine-4-carboxylic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.000007
2-(1-(3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propanoyl)-3-azetidinyl)acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000013
2-(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]-4-piperidinyl)acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.00000051
2-(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-1,2,3-triazol-4-yl)acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.00000081
2-(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-1,2,3-triazol-5-yl)acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000013
2-(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-pyrazol-3-yl)acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000031
2-(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-pyrazol-4-yl)acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000016
2-(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-pyrazol-5-yl)acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0006
2-(1-[2-[(4S,6R)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]-4-piperidinyl)acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000027
2-(1-[2-[8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]-4-piperidinyl)acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000024
2-(1-[3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propanoyl]-4-piperidinyl)acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000011
2-(2-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl)ethyl]-2H-1,2,3,4-tetrazol-5-yl]-2-methylpropanoic acid
0.0000043
2-(4-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]-1-piperazinyl)acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000022
2-(4-[3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propanoyl]-2-oxo-1-piperazinyl)acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000023
2-([2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]amino)acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000017
2-[(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-1,2,3-triazol-4-yl)methoxy]-2-ethylbutanoic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.00000069
2-[(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-1,2,3-triazol-4-yl)methoxy]-2-methylpropanoic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.00000068
2-[(1-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-1H-1,2,3-triazol-4-yl)methoxy]acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000009
2-[(1-[3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propanoyl]-4-piperidinyl)methoxy]acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000008
2-[(1-[3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propanoyl]-4-piperidinyl)oxy]acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000025
2-[(2-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-2H-1,2,3,4-tetrazol-5-yl)methoxy]-2-methylpropanoic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.000162
2-[(6S)-8-chloro-6-(2,3-dimethoxyphenyl)-1-(propan-2-yl)-6,10b-dihydro-1H,4H-[2]benzoxepino[4,5-c][1,2]oxazol-4-yl]-1-[(3R)-3-hydroxypyrrolidin-1-yl]ethanone
Homo sapiens
-
pH and temperature not specified in the publication
0.0000016
2-[1,8-dichloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.00000089
2-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-2H-1,2,3,4-tetrazol-5-carboxylic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0006
2-[8-chloro-6-(1-naphthyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.000052
2-[8-chloro-6-(2,3-dichlorobenzoyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.00044
2-[8-chloro-6-(2,3-dihydro-1,4-benzodioxin-5-yl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000076
2-[8-chloro-6-(2,3-dimethoxyphenyl)-1-(4-morpholinylmethyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.00054
2-[8-chloro-6-(2,3-dimethoxyphenyl)-1-[(dimethylamino)methyl]-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000033
2-[8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.00000085
3-(2-[2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]ethyl]-2H-1,2,3,4-tetrazol-5-yl)propanoic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.00073
3-(biphenyl-4-ylmethyl)-1-azabicyclo[2.2.2]oct-2-ene
Trypanosoma cruzi
-
IC50: 730 nM
0.000004
3-([2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]amino)benzoic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000029
3-([2-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetyl]amino)propionic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000014
3-[(1-[3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propanoyl]-4-piperidinyl)oxy]propanoic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000031
3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6Hpyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propionic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.00083
3-[[4-(benzyloxy)phenyl]ethynyl]-1-azabicyclo[2.2.2]oct-2-ene
Trypanosoma cruzi
-
IC50: 830 nM
0.0000016
4-[3-[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-4H,6H-pyrrolo[1,2-a][4,1]benzoxazepin-4-yl]propanoyl]-2-morpholine carboxylic acid
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0024
6-([[(1R,5S)-7-chloro-5-(2-chlorophenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetyl]amino)hexanoic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.0001
chlorogenic acid
Sus scrofa
-
pH 7.4, 37C
0.00013
CP-294838
Homo sapiens
P37268
a benzoxazepinone IC50 130 nM
0.00002
CP-295697
Homo sapiens
P37268
a bisphosphonate, IC50: 20 nM
0.00000084
E5700
Trypanosoma cruzi
-
IC50: 0.84 nM
0.00000352
ER119884
Trypanosoma cruzi
-
IC50: 3.52 nM
0.00005
ethyl 4-(1-azabicyclo[2.2.2]oct-2-en-3-yl)benzoate
Trypanosoma cruzi
-
IC50: 50 nM
0.02
ethyl [(1R,5S)-7-chloro-5-(2-chlorophenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetate
Homo sapiens
-
pH and temperature not specified in the publication
0.00022
methyl 2-[8-chloro-6-(2,3-dimethoxyphenyl)-4H,6Hpyrrolo[1,2-a][4,1]benzoxazepin-4-yl]acetate
Rattus norvegicus
-
pH 7.2-7.5, 37C
0.0000007
zaragozic acid
Homo sapiens
P37268
IC50 0.7 nM
-
0.0000955
zaragozic acid A
Thermosynechococcus elongatus
-
pH 7.2, 37C
0.0153
[(1R,5R)-7-chloro-1-(2-methylpropyl)-2-oxo-5-phenyl-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.02
[(1R,5S)-1-benzyl-7-chloro-5-(2-chlorophenyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.0022
[(1R,5S)-5-(2-bromophenyl)-7-chloro-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.02
[(1R,5S)-5-(2-chlorophenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
0.0012
[(1R,5S)-7-chloro-5-(2,3-dimethoxyphenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.02
[(1R,5S)-7-chloro-5-(2-chlorophenyl)-1-(2-hydroxy-2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.0033
[(1R,5S)-7-chloro-5-(2-chlorophenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.0019
[(1R,5S)-7-chloro-5-(2-methoxyphenyl)-1-(2-methylpropyl)-2-oxo-1,2,4,5-tetrahydro-3H-3-benzazepin-3-yl]acetic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.00142
[(4R,6R)-8-chloro-6-(2,3-dimethoxyphenyl)-1-(propan-2-yl)-6,10b-dihydro-1H,4H-[2]benzoxepino[4,5-c][1,2]oxazol-4-yl]acetic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.000056
[(4R,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-1-(propan-2-yl)-6,10b-dihydro-1H,4H-[2]benzoxepino[4,5-c][1,2]oxazol-4-yl]acetic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.000169
[(4S,6R)-8-chloro-6-(2,3-dimethoxyphenyl)-1-(propan-2-yl)-6,10b-dihydro-1H,4H-[2]benzoxepino[4,5-c][1,2]oxazol-4-yl]acetic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.0055
[(4S,6S)-8-chloro-6-(2,3-dimethoxyphenyl)-1-(propan-2-yl)-6,10b-dihydro-1H,4H-[2]benzoxepino[4,5-c][1,2]oxazol-4-yl]acetic acid
Homo sapiens
-
pH and temperature not specified in the publication
0.000223
[(6S)-8-chloro-6-(2,3-dimethoxyphenyl)-1-(propan-2-yl)-6,10b-dihydro-1H,4H-[2]benzoxepino[4,5-c][1,2]oxazol-4-yl]acetic acid
Homo sapiens
-
pH and temperature not specified in the publication
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.1
-
truncated protein, soluble extract
0.459
-
truncated protein, after 4.5fold purification
0.816
-
presqualene
15.6
-
presqualene
additional information
pH RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5.2 - 8.2
-
pH 5.2: about 45% of maximum activity, pH 8.2: about 75% of maximum activity
6 - 9
activity range, over 90% of maximal activity at pH 7.0-8.0, 30% at pH 6.0, 20% at pH 9.0
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25 - 30
-
formation of lycopersene
35
-
assay at
TEMPERATURE RANGE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30 - 45
83% and 88% activity at a temperature of 30C and 45C
pI VALUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.5
calculated
6.64
sequence calculation
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
petiole of cotyledon
Manually annotated by BRENDA team
-
main source
Manually annotated by BRENDA team
expression level is relatively low in mycelia incubated for 12 days, increases after 14 to 20 days of incubation, and reaches a relatively high level in the mushroom primordia
Manually annotated by BRENDA team
expression level is relatively low in mycelia incubated for 12 days, increases after 14 to 20 days of incubation, and reaches a relatively high level in the mushroom primordia
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
PDB
SCOP
CATH
ORGANISM
UNIPROT
Trypanosoma cruzi (strain CL Brener)
Trypanosoma cruzi (strain CL Brener)
Trypanosoma cruzi (strain CL Brener)
Trypanosoma cruzi (strain CL Brener)
Trypanosoma cruzi (strain CL Brener)
Trypanosoma cruzi (strain CL Brener)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
32000 - 35000
-
gel filtration
41670
-
SDS-PAGE, estimated molecular mass
42600
-
sucrose density gradient centrifugation, gel filtration
54500
-
gel filtration, sucrose density gradient sedimentation
55000 - 60000
-
gel filtration
55000
-
gel filtration
68000
-
gel filtration
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
monomer
-
1 * 64000, SDS-PAGE
additional information
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
in complex with different inhibitors
mutant with deletion of 47 C-terminal amino acids
purified recombinant truncated detagged SQS(31-370) in complex with inhibitor zaragozic acid A, vapour diffusion, mixing an equal volume of protein solution containing 15 mg/ml protein with precipitating solution containing 20% PEG2K-MME, 0.01 M NiCl2, 0.1 M Tris, pH 8.5, 1.4 M sodium citrate tribasic dehydrate, 0.1 M Na-HEPES, pH 7.5, 2 M K2HPO4/NaH2HPO4, pH 6.5, room temperature, X-ray diffraction structure determination and analysis, molecular replacement
-
pH STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.5
-
irreversible denaturation above
489838
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
25
-
in presence of deoxycholate, 5 min, 50% loss of activity
41
-
without deoxycholate, 5 min, 50% loss of activity
60
purified recombinant enzyme, pH 7.4, loss of 85% activity
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
a combination of 10% methanol, 10% glycerol, 30 mM octyl-beta-D-glucopyranoside, 0.4% Brij-58, and 1 mM DTT in 25 mM sodium phosphate, pH 7.4, essential for stability and maximal activity
-
detergent, e.g. deoxycholate, destabilizes
-
markedly stabilized by 30% glycerol and 0.02 M 2-mercaptoethanol
-
methanol stabilizes
-
methanol, 10%, does not stabilize
NADPH has no effect on stability
-
octylglucoside, 5 mM, causes rapid loss of activity
-
stable in buffer containing 5 mM octylglucoside and 15 mM CHAPS
-
sucrose stabilizes
-
sucrose, 10%, does not stabilize
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-80C, 25 mM sodium phosphate (pH 7.4, containing 20 mM NaCl, 2 mM dithiothreitol, 1 mM EDTA, 40% glycerol, 10% methanol, 1 mM phenylmethylsulfonyl fluoride, 0.01 mM leupeptin, 0.001 mM pepstatin), extended periods of time, no loss of activity
-
-80C, stable for at least 6 months
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in E. coli
-
gel purification and Ni-NTA column purification
-
HiTrap nickel-chelating column chromatography and MonoQ HR5/5 anion-exchange column chromatography
-
overexpressed in E. coli
-
partial
recombinant His-tagged protein found exclusively in inclusion bodies. Solubilization in presence of glycerol
-
recombinant His6-tagged LdSSN from Escherichia coli strain BL21(DE3) by anion exchange chromatography, nickel affinity chrmatography is not successful
recombinant His6-tagged WsSQS1and WsSQS2 proteins from Escherichia coli by nickel affinity chromatgraphy
recombinant protein
-
recombinant truncated N-terminally His6-tagged SQS(31-370) from Escherichia coli strain BL21(DE3), the tag is cleaved off by thrombin
-
trypsin-truncated enzyme
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
clone 8380-1, gene PSS1, DNA and amino acid sequence determination and analysis, overexpression in Solanum tuberosum plants, only four of 12 SQS-transgenics have greater steroidal glycoalkaloid levels than control, quantitative real-time PCR expression analysis
cloning in Escherichia coli strain DH5alpha, overexpression of the endogenoous gene encoding squalene synthase in Withania somnifera via transfection with Agrobacterium tumefaciens strain GV3101 using binary vector pBI121
-
development of a plasmid for heterologous expression of yeast squalene synthase in Escherichia coli
-
DNA and amino acid sequence determination and analysis, real-time RT-PCR expression analysis
-
enzyme expressed in Escherichia coli
-
expressed in Escherichia coli, several truncated versions of SQS with a His tag attached to the amino terminus
-
expressed in Mus musculus C57BL/6
-
expression as green fluorescent protein-tagged version in onion; expression in Escherichia coli
expression in Escherichia coli
expression in Escherichia coli, His-tagged protein found exclusively in inclusion bodies
-
gene BfSS1, overexpression in Bupleurum falcatum using transfection via Agrobacterium tumefaciens strain GV3101
gene CbSqS, DNA and amino acid sequence determination and analysis, phylogenetic analysis, expression in Escherichia coli strain M15
gene fragment SQS(31-370) as N-terminally His6-tagged protein containing a thrombin cleavage site in Escherichia coli strain BL21(DE3)
-
genes WsSQS1and WsSQS2, DNA and amino acid sequence determination and analysis, phylogenetic tree, quantitative real-time PCR tissue expression analysis, expression as soluble recombinant enzymes with 24 hydrophobic amino acids deleted from the C-terminus and expressed as His6-tagged proteins in Escherichia coli
LdSSN DNA and amino acid sequence determination and analysis, sequence comparison, phylogenetic analysis, expression as C-terminally His6-tagged protein in Escherichia coli strain BL21 (DE3)
overview
yeast enzyme overexpressed in Escherichia coli
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
BfSS1 mRNA accumulates ubiquitously in plant organs and markedly increases in roots after treatment with methyl jasmonate, abscisic acid, and ethephon
infectionn of the plants with Fusarium oxysporum induces the squalene synthase expression
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D280E
enzymic activity slightly above wild-type activity
D280P
enzymic activity about 74% of wild-type activity
D280Q
enzymic activity about 50% of wild-type activity
F285L
no enzymic activity
synthesis
overexpression of enzyme in Eleutherococcus senticosus, results in enzyme activity up to 3fold higher than wild-type and increase in phytosterols beta-sitosterol and stigmasterol as well as in triterpene saponin levels
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
drug development
medicine
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