1.14.14.17: squalene monooxygenase
This is an abbreviated version!
For detailed information about squalene monooxygenase, go to the full flat file.
Word Map on EC 1.14.14.17
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1.14.14.17
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cholesterol
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sterol
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terbinafine
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ergosterol
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trichophyton
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mevalonate
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lanosterol
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allylamine
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2,3-oxidosqualene
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hmg-coa
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itraconazole
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mentagrophytes
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rubrum
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oxidosqualene
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terbinafine-resistant
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tellurium
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tinea
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naftifine
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interdigitale
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antimycotic
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bloch
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griseofulvin
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dammarenediol
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dermatophytoses
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cycloartenol
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beta-amyrin
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medicine
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corporis
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drug development
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nutrition
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biotechnology
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pharmacology
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cholesterogenic
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synthesis
- 1.14.14.17
- cholesterol
- sterol
- terbinafine
- ergosterol
- trichophyton
- mevalonate
- lanosterol
- allylamine
- 2,3-oxidosqualene
- hmg-coa
- itraconazole
- mentagrophytes
- rubrum
- oxidosqualene
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terbinafine-resistant
- tellurium
- tinea
- naftifine
- interdigitale
-
antimycotic
-
bloch
-
griseofulvin
-
dammarenediol
-
dermatophytoses
- cycloartenol
- beta-amyrin
- medicine
-
corporis
- drug development
- nutrition
- biotechnology
- pharmacology
-
cholesterogenic
- synthesis
Reaction
Synonyms
CYP17, cytochrome P450 17alpha hydroxylase/17,20 lyase, EC 1.14.13.132, EC 1.14.99.7, Erg1, Erg1 protein, Erg1p, hydroxylase, squalene, oxygenase, squalene mono-, PgSQE1, PgSQE2, SE, SE1, SE3, SQE, SQE-I, SQE-II, sqe1, SQE3, SQLE, squalen expoxidase, squalene 2,3-epoxidase, squalene 2,3-oxidocyclase, squalene epoxidase, squalene epoxidase 1, squalene epoxidase 3, squalene hydroxylase, squalene mono-oxygenase, squalene oxydocyclase, squalene-2,3-epoxidase, squalene-2,3-epoxide cyclase, TkSQE1, TkSQE2, TkSQE3, TkSQE4
ECTree
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Substrates Products
Substrates Products on EC 1.14.14.17 - squalene monooxygenase
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REACTION DIAGRAM
(3S)-2,3-epoxy-2,3-dihydrosqualene + 1-carba-1-deaza-FAD + H2O
squalene + 1-carba-1-deaza-FADH2 + O2
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r
(3S)-squalene-2,3-epoxide + AH2 + O2
(3S,22S)-2,3-22,23-dioxidosqualene + A + H2O
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the wild-type enzyme also catalyzes conversion of (3S)2,3-oxidosqualene to (3S,22S)-2,3-22,23-dioxidosqualene
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?
1,1-bisnorsqualene + NADPH + O2
1,1-bisnor-squalene-2,3-epoxide + NADP+ + H2O
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?
1-methylsqualene + NADPH + O2
1-methyl-squalene-2,3-epoxide + NADP+ + H2O
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?
1-norsqualene + NADPH + O2
1-norsqualene-2,3-epoxide + NADP+ + H2O
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?
10,11,14,15-tetrahydrosqualene + NADPH + O2
10,11,14,15-tetrahydro-squalene-2,3-epoxide + NADP+ + H2O
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?
10,11-dihydrosqualene + NADPH + O2
10,11-dihydro-squalene-2,3-epoxide + NADP+ + H2O
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?
2,3-oxidosqualene + NADPH + O2
2,3,22,23-dioxidosqualene + NADP+ + H2O
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N-terminal truncated recombinant enzyme
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?
6,7,18,19-tetrahydrosqualene + NADPH + O2
6,7,18,19-tetrahydro-(S)-squalene-2,3-epoxide
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?
squalene + reduced cytochrome P450 + H+ + O2
(3S)-squalene-2,3-epoxide + cytochrome P450 + H2O
absolutely stereo- and regiospecific reaction, co-reaction with NADPH-cytochrome P450 reductase
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?
squalene + reduced cytochrome P450 + O2
(S)-squalene-2,3-epoxide + cytochrome P450 + H2O
first step in the cyclic chloesterol biosynthesis
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?
squalene + reduced NADPH-cytochrome P450 reductase + O2
(3S)-2,3-epoxy-2,3-dihydrosqualene + oxidized NADPH-cytochrome P450 reductase + H2O
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r
squalene + [reduced NADPH-hemoprotein reductase] + O2
(3S)-2,3-epoxy-2,3-dihydrosqualene + [oxidized NADPH-hemoprotein reductase] + H2O
(3S)-2,3-epoxy-2,3-dihydrosqualene + FAD + H2O
squalene + FADH2 + O2
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r
(3S)-squalene-2,3-epoxide + A + H2O
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rate-limiting step in chloesterol biosynthesis
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?
squalene + AH2 + O2
(3S)-squalene-2,3-epoxide + A + H2O
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aromatic amino acid residues located at the substrate-binding domain of the active-site, e.g. Ph223 and Tyr473, control the stereochemical course of the enzyme reaction, mechanism of regio- and stereo-specific epoxidation of squalene to (3S)2,3-oxidosqualene, overview
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(S)-squalene-2,3-epoxide + A + H2O
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squalene + AH2 + O2
(S)-squalene-2,3-epoxide + A + H2O
production of the precursor for all known angiosperm cyclic triterpenoids, which include membrane sterols, brassinosteroid phytohormones, and non-steroidal triterpenoids, overview
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?
squalene + AH2 + O2
(S)-squalene-2,3-epoxide + A + H2O
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oxidosqualene or dioxidosqualene appears to be the branching point for primary metabolism and secondary metabolites in basidiomycetes
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squalene + AH2 + O2
(S)-squalene-2,3-epoxide + A + H2O
rate-limiting enzyme in the triterpene saponins biosynthetic pathway, overview
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?
squalene + AH2 + O2
(S)-squalene-2,3-epoxide + A + H2O
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?
squalene + AH2 + O2
(S)-squalene-2,3-epoxide + A + H2O
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the enzyme contains two highly conserved motifs 1 and 2, which flank the FAD cofactor and form part of the interface between cofactor and substrate binding domains in the structure modelling, substrate binding domain structure, overview
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squalene + AH2 + O2
(S)-squalene-2,3-epoxide + A + H2O
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the enzyme is involved in ergosterol biosynthesis
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(S)-squalene-2,3-epoxide + oxidized electron donor + H2O
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squalene + electron donor + O2
(S)-squalene-2,3-epoxide + oxidized electron donor + H2O
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first oxygenase and last nonsterol reaction of sterol biosynthesis
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?
squalene + electron donor + O2
(S)-squalene-2,3-epoxide + oxidized electron donor + H2O
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may be rate-limiting step in cholesterol biosynthesis in non-cholesterogenic tissues
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?
(S)-squalene-2,3-epoxide + NADP+ + H2O
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squalene + NAD(P)H + O2
(S)-squalene-2,3-epoxide + NADP+ + H2O
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NADH is preferred
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?
squalene + NAD(P)H + O2
(S)-squalene-2,3-epoxide + NADP+ + H2O
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NADH is preferred
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?
squalene + NAD(P)H + O2
(S)-squalene-2,3-epoxide + NADP+ + H2O
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?
squalene + NAD(P)H + O2
(S)-squalene-2,3-epoxide + NADP+ + H2O
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?
squalene + NAD(P)H + O2
(S)-squalene-2,3-epoxide + NADP+ + H2O
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?
squalene + NAD(P)H + O2
(S)-squalene-2,3-epoxide + NADP+ + H2O
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?
squalene + NAD(P)H + O2
(S)-squalene-2,3-epoxide + NADP+ + H2O
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?
squalene + NAD(P)H + O2
(S)-squalene-2,3-epoxide + NADP+ + H2O
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?
squalene + NAD(P)H + O2
(S)-squalene-2,3-epoxide + NADP+ + H2O
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NADPH is preferred
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?
squalene + NAD(P)H + O2
(S)-squalene-2,3-epoxide + NADP+ + H2O
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specific for NADPH
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?
squalene + NAD(P)H + O2
(S)-squalene-2,3-epoxide + NADP+ + H2O
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NADPH is preferred
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?
squalene + NAD(P)H + O2
(S)-squalene-2,3-epoxide + NADP+ + H2O
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NADPH is slightly preferred
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?
(S)-squalene-2,3-epoxide + acceptor + H2O
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squalene + reduced acceptor + O2
(S)-squalene-2,3-epoxide + acceptor + H2O
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epoxidation of squalene is the first step in cholesterol biosynthesis
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squalene + reduced acceptor + O2
(S)-squalene-2,3-epoxide + acceptor + H2O
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squalene + reduced acceptor + O2
(S)-squalene-2,3-epoxide + acceptor + H2O
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epoxidation of squalene is the first step in cholesterol biosynthesis
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squalene + reduced acceptor + O2
(S)-squalene-2,3-epoxide + acceptor + H2O
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squalene + reduced acceptor + O2
(S)-squalene-2,3-epoxide + acceptor + H2O
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epoxidation of squalene is the first step in cholesterol biosynthesis
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(3S)-2,3-epoxy-2,3-dihydrosqualene + [oxidized NADPH-hemoprotein reductase] + H2O
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?
squalene + [reduced NADPH-hemoprotein reductase] + O2
(3S)-2,3-epoxy-2,3-dihydrosqualene + [oxidized NADPH-hemoprotein reductase] + H2O
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?
squalene + [reduced NADPH-hemoprotein reductase] + O2
(3S)-2,3-epoxy-2,3-dihydrosqualene + [oxidized NADPH-hemoprotein reductase] + H2O
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?
squalene + [reduced NADPH-hemoprotein reductase] + O2
(3S)-2,3-epoxy-2,3-dihydrosqualene + [oxidized NADPH-hemoprotein reductase] + H2O
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?
squalene + [reduced NADPH-hemoprotein reductase] + O2
(3S)-2,3-epoxy-2,3-dihydrosqualene + [oxidized NADPH-hemoprotein reductase] + H2O
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Arabidopsis thaliana squalene epoxidase 1 is essential for root and seed development
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additional information
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Arabidopsis thaliana squalene epoxidase 1 is essential for root and seed development
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additional information
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Arabidopsis thaliana squalene epoxidase 1 is essential for root and seed development
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additional information
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Arabidopsis thaliana squalene epoxidase 1 is essential for root and seed development
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additional information
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Arabidopsis thaliana squalene epoxidase 1 is essential for root and seed development
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additional information
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the enzyme affects morphogenesis and drug susceptibilities
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additional information
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the enzyme activity is associated with cytochrome P450 17alpha hydroxylase/17,20 lyase CYP17 in cholesterol biosynthesis in Leydig cells
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additional information
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squalene epoxidase interacts with NADPH-cytochrome P450 reductase and a second microsomal reductase for the conversion of squalene to 2,3(s)-oxidosqualene and to lanosterol in the cholesterol biosynthesis pathway, overview
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additional information
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location of the substrate-binding site by binding studies using the photolabeling inhibitor trisnorsqualene alcohol diazoester, key residues are K399, R400, and D407
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