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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

Reaction

squalene
+
[reduced NADPH-hemoprotein reductase]
 +
O2
=
(3S)-2,3-epoxy-2,3-dihydrosqualene
 +
[oxidized NADPH-hemoprotein reductase]
 +
H2O

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

     1 Oxidoreductases
         1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen
             1.14.14 With reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen into the other donor
                1.14.14.17 squalene monooxygenase

Inhibitors

Inhibitors on EC 1.14.14.17 - squalene monooxygenase

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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(-)-epicatechin-3-O-gallate
-
50% inhibition at 0.0013 mM
(-)-epigallocatechin-3-O-gallate
(-)-gallocatechin-3-O-gallate
-
50% inhibition at 0.00067 mM
(2R,3R)-2,3-dimethyl-1-(3-phenylprop-2-ynyl)piperidine hydrochloride
-
-
(2R,3S)-2,3-dimethyl-1-(3-phenylprop-2-ynyl)piperidine hydrochloride
-
-
(2R,5R)-2,5-dimethyl-1-(3-phenylprop-2-ynyl)piperidine hydrochloride
-
-
(2R,5S)-2,5-dimethyl-1-(3-phenylprop-2-ynyl)piperidine hydrochloride
-
-
(2R,6R)-2,6-dimethyl-4-(3-phenylprop-2-ynyl)morpholine hydrochloride
-
-
(3R,5R)-3,5-dimethyl-1-(3-phenylprop-2-ynyl)piperidine hydrochloride
-
-
(3R,5S)-3,5-dimethyl-1-(3-phenylprop-2-ynyl)piperidine hydrochloride
-
-
(E)-N-(6,6-dimethylhept-2-en-4-ynyl)-N-methyl-1-naphthalenemethaneamine hydrochloride
(E)-N-ethyl-N-(6,6-dimethyl-2-hepten-4-ynyl)-3-[2-methyl-2-(3-thienylmethoxy)propyloxy]benzylamine hydrochloride
-
trivial name FR194738, 0.0000098 mM, 50% inhibition of enzyme activity in HepG2 cell homogenate
(E)-N-methyl-N-(3-phenylprop-2-enyl)-1-naphthalenemethaneamine
1,2,6-Tri-O-galloyl-beta-D-glucose
-
0.00063 mM, 50% inhibition
1,6-di-O-galloyl-2-O-cinnamoyl-beta-D-glucose
-
0.00058 mM, 50% inhibition
1-[3-(2,3-dichlorophenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
1-[3-(2,4-dichlorophenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
1-[3-(2,5-dichlorophenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
1-[3-(2,6-dichlorophenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
1-[3-(2-chlorophenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
1-[3-(3,4-dichlorophenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
1-[3-(3,4-dichlorophenyl)prop-2-ynyl]-3-ethylpiperidine hydrochloride
-
-
1-[3-(3,5-dichlorophenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
strong, selective inhibition
1-[3-(3,5-dichlorophenyl)prop-2-ynyl]pyrrolidine hydrochloride
-
-
1-[3-(3,5-difluorophenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
1-[3-(3-chloro-5-methoxyphenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
1-[3-(3-chlorophenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
1-[3-(3-cyanophenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
1-[3-(3-methoxyphenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
1-[3-(3-methylphenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
1-[3-(4-chloro-3-trifluoromethylphenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
1-[3-(4-chlorophenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
1-[3-(4-cyanophenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
1-[3-(4-fluorophenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
1-[3-(4-methylphenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
1-[3-(4-trifluoromethylphenyl)-prop-2-ynyl]-3-methylpiperidine hydrochloride
-
-
2-ethyl-1-(3-phenylprop-2-ynyl)piperidine hydrochloride
-
-
2-methyl-1-(3-phenylprop-2-ynyl)piperidine hydrochloride
-
-
2-propyl-1-(3-phenylprop-2-ynyl)piperidine hydrochloride
-
-
26-hydroxysqualene
-
competitive
3-ethyl-1-(3-phenylprop-2-ynyl)piperidine hydrochloride
-
-
3-methyl-1-(5-phenylpent-2-ynyl)piperidine hydrochloride
-
-
3-methyl-1-[3-(2-naphthyl)prop-2-ynyl]piperidine hydrochloride
-
-
3-methyl-1-[3-(3-thienyl)-prop-2-ynyl]piperidine hydrochloride
-
-
4-(3-phenyl-2-propenyl)piperazine-1-ylamide of 3-(2-furyl)propenoic acid
-
analysing effect on accumulation of more squalen and less (S)-squalene-2,3-epoxide in Trypanosoma cruzi. Analysing antifungal effect on Microsporum canis C 112, Epidermophyton floccosum C 114, Trichophyton rubrum C 110, Trichophyton mentagrophytes ATCC 9972 and Microsporum gypseum C 115
4-(3-phenyl-2-propenyl)piperazine-1-ylamide of 3-(5-nitro2-furyl)propenoic acid
-
analysing effect on accumulation of more squalen and less (S)-squalene-2,3-epoxide in Trypanosoma cruzi. Analysing antifungal effect on Microsporum canis C 112, Epidermophyton floccosum C 114, Trichophyton rubrum C 110, Trichophyton mentagrophytes ATCC 9972 and Microsporum gypseum C 115
4-allyl-1-(3-furyl-2-propenylidene)thiosemicarbazide
-
analysing effect on accumulation of more squalen and less (S)-squalene-2,3-epoxide in Trypanosoma cruzi. Analysing antifungal effect on Microsporum canis C 112, Epidermophyton floccosum C 114, Trichophyton rubrum C 110, Trichophyton mentagrophytes ATCC 9972 and Microsporum gypseum C 115
4-allyl-1-(5-nitrofurfurilydene)thiosemicarbazide
-
analysing effect on accumulation of more squalen and less (S)-squalene-2,3-epoxide in Trypanosoma cruzi. Analysing antifungal effect on Microsporum canis C 112, Epidermophyton floccosum C 114, Trichophyton rubrum C 110, Trichophyton mentagrophytes ATCC 9972 and Microsporum gypseum C 115
4-allyl-1-(5-nitrothenylidene)thiosemicarbazide
-
analysing effect on accumulation of more squalen and less (S)-squalene-2,3-epoxide in Trypanosoma cruzi. Analysing antifungal effect on Microsporum canis C 112, Epidermophyton floccosum C 114, Trichophyton rubrum C 110, Trichophyton mentagrophytes ATCC 9972 and Microsporum gypseum C 115
4-allyl-1-furfurylidenethiosemicarbazide
-
analysing effect on accumulation of more squalen and less (S)-squalene-2,3-epoxide in Trypanosoma cruzi. Analysing antifungal effect on Microsporum canis C 112, Epidermophyton floccosum C 114, Trichophyton rubrum C 110, Trichophyton mentagrophytes ATCC 9972 and Microsporum gypseum C 115
4-allyl-1-thenylidenethiosemicarbazide
-
analysing effect on accumulation of more squalen and less (S)-squalene-2,3-epoxide in Trypanosoma cruzi. Analysing antifungal effect on Microsporum canis C 112, Epidermophyton floccosum C 114, Trichophyton rubrum C 110, Trichophyton mentagrophytes ATCC 9972 and Microsporum gypseum C 115
4-allyl-1-[3-(5-nitro-2-furyl)-2-propenylidene]
-
analysing effect on accumulation of more squalen and less (S)-squalene-2,3-epoxide in Trypanosoma cruzi. Analysing antifungal effect on Microsporum canis C 112, Epidermophyton floccosum C 114, Trichophyton rubrum C 110, Trichophyton mentagrophytes ATCC 9972 and Microsporum gypseum C 115
4-hydroxymercuribenzoate
-
1 mM, 35% inhibition
4-[3-(3-methylpiperidin-1-yl)prop-1-ynyl]benzenesulfonamide hydrochloride
-
-
amorolfine
-
0.03 mM, 50% inhibition
antimycin A
-
0.1 mM, 44% inhibition
bovine serum albumin
-
-
-
chloromercuriphenylsulfonate
-
1 mM, 35% inhibition
Cu2+
-
5 mM, 99% inhibition
deoxycholate
-
-
diethyldithiocarbamate
-
capable of inhibiting the jasmonic acid biosynthesis and depressing the 2-hydroxyethyl jasmonate-induced up-regulation of squalene epoxide gene expression
dimethyltelluride
-
approx. 0.0001 mM, 50% inhibition of recombinant enzyme, 0.1 mM, complete inhibition, preincubation with 1 mM glutathione maintains 50% of initial activity
dimethyltellurium dichloride
-
approx. 0.0001 mM, 50% inhibition of recombinant enzyme, 0.1 mM, complete inhibition, preincubation with 1 mM glutathione maintains 50% of initial activity
dodecyl gallate
epicatechin-3-O-gallate
-
0.0013 mM, 50% inhibition
epigallocatechin-3-O-gallate
farnesyl gallate
-
0.0015 mM, 50% inhibition
FR 194738
-
gallocatechin-3-O-gallate
-
0.00067 mM, 50% inhibition
geranyl gallate
-
0.0125 mM, 50% inhibition
geranylgeranyl gallate
-
0.0045 mM, 50% inhibition
H2O2
-
inhibition above 2 mM
ketoconazole
-
the sensitive of conserved motif 1 mutant enzymes is increased compared tot he wild-type enzyme
Mega-8
-
0.3%, 19% inhibition
methylselenol
-
0.095 mM, 50% inhibition of recombinant enzyme, 1 mM, complete inhibition
N-(2-hydroxyethyl)-3-(5-nitro-2-furyl)propenamide
-
analysing effect on accumulation of more squalen and less (S)-squalene-2,3-epoxide in Trypanosoma cruzi. Analysing antifungal effect on Microsporum canis C 112, Epidermophyton floccosum C 114, Trichophyton rubrum C 110, Trichophyton mentagrophytes ATCC 9972 and Microsporum gypseum C 115
n-dodecyl gallate
-
0.000061 mM, 50% inhibition
N-ethylmaleimide
-
1 mM, 35% inhibition
N1,N1,2-trimethyl-N2-(3-phenylprop-2-ynyl)propane-1,2-diamine
-
-
naftifine
-
the sensitive of conserved motif 1 mutant enzymes is increased compared tot he wild-type enzyme
NB-598
Pharma Project 4501
-
-
-
Phenylarsine oxide
-
recombinant enzyme, glutathione and 2,3-dimercaptopropanol protect almost completely
phenylbutyl gallate
-
0.0613 mM, 50% inhibition
phenyldecyl gallate
-
0.0153 mM, 50% inhibition
phenylhexyl gallate
-
0.0119 mM, 50% inhibition
phenyloctyl gallate
-
0.0125 mM, 50% inhibition
procyanidin B-2 3,3'-di-O-gallate
-
0.00054 mM, 50% inhibition
procyanidin B-5 3,3'-di-O-gallate
-
0.00055 mM, 50% inhibition
rotenone
-
0.1 mM, 67% inhibition
SDZ 87-469
-
0.000020 mM, 50% inhibition
Selenite
selenium dioxide
-
recombinant enzyme
tellurite
tellurium
tellurium dioxide
-
37 mM, 50% inhibition of the recombinant enzyme
tellurium nanoparticle
-
tellurium nanoparticles inhibit the squalene monooxygenase enzyme, and, as a result, can cause an increase in the expression level of the ERG1 gene
-
terbinafine
theasinensin A
Thiosemicarbazide
-
analysing effect on accumulation of more squalen and less (S)-squalene-2,3-epoxide in Trypanosoma cruzi. Analysing antifungal effect on Microsporum canis C 112, Epidermophyton floccosum C 114, Trichophyton rubrum C 110, Trichophyton mentagrophytes ATCC 9972 and Microsporum gypseum C 115
tolciclate
-
0.000028 mM, 50% inhibition
tolnaftate
-
0.0000515 mM, 50% inhibition
tris norsqualene alcohol
tris norsqualene cyclopropylamine
trisnorsqualene alcohol
trisnorsqualene alcohol diazoester
-
i.e. TNSA-Dza, competitive, able to photocovalently modify the native protein
trisnorsqualene cyclopropylamine
trisnorsqualene difluoromethylidene
-
0.0054 mM, 50% inhibition
trisnorsqualene gallate
-
0.0051 mM, 50% inhibition
trisnorsqualene hydroxylamine
-
mechanism-based inactivator
Triton X-100
additional information
-