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(24Z)-5alpha-stigmast-7,24(241)-dien-3beta-ol + O2 + reduced acceptor
(24Z)-stigmasta-5,7,24(241)-trien-3-beta-ol + acceptor + H2O
-
-
-
?
(3beta,24R)-ergost-7-en-3-ol + ferrocytochrome b5 + O2 + H+
(3beta,24R)-ergosta-5,7-dien-3-ol + ferricytochrome b5 + H2O
-
-
-
-
?
14-methylfecosterol + ferrocytochrome b5 + O2 + H+
14-methylergosta-5,8,24(28)-trien-3beta-ol + ferricytochrome b5 + H2O
-
-
-
?
5alpha-cholest-22-en-3beta-ol + ferrocytochrmoe b5 + H+ + O2
cholesta-5,22-dien-3beta-ol + ferricytochrome b5 + 2 H2O
-
-
-
?
5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+
cholesta-5,7-dien-3beta-ol + 2 ferricytochrome b5 + 2 H2O
5alpha-cholest-7-en-3beta-ol + ferrocytochrmoe b5 + H+ + O2
cholesta-5,7-dien-3beta-ol + ferricytochrome b5 + H2O
NADH is more efficient than NADPH
-
-
?
5alpha-cholest-7-en-3beta-ol + ferrocytochrome b5 + H+ + O2
cholesta-5,7-dien-3beta-ol + ferricytochrmoe b5 + H2O
-
-
-
?
5alpha-cholest-7-en-3beta-ol + ferrocytochrome b5 + H+ + O2
cholesta-5,7-dien-3beta-ol + ferricytochrome b5 + 2 H2O
NADH is more efficient than NADPH
-
-
?
5alpha-cholest-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+
? + ferricytochrome b5 + H2O
-
-
-
-
?
5alpha-cholesta-7,22-dien-3beta-ol + ferrocytochrome b5 + H+ + O2
cholesta-5,7,22-trien-3beta-ol + ferricytochrome b5 + 2 H2O
-
-
-
?
5alpha-cholestan-3beta-ol + ferrocytochrome b5 + H+ + O2
cholest-5-en-3beta-ol + ferricytochrome b5 + 2 H2O
-
-
-
?
5alpha-ergost-7,24(241)-dien-3beta-ol + O2 + ferrocytochrome b5
ergosta-5,7,24(241)-trien-3beta-ol + H2O2 + ferricytochrome b5
5alpha-ergosta-7,22-dien-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosterol + ferricytochrome b5 + H2O
5alpha-ergosta-7,24-dien-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosta-5,7,24-trien-3beta-ol + ferricytochrome b5 + H2O
5alpha-ergosta-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosta-5,7-dien-3beta-ol + ferricytochrome b5 + H2O
avenasterol + ferrocytochrome b5 + O2 + H+
?
-
-
-
-
?
cholest-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+
cholest-5,7-dien-3beta-ol + ferricytochrome b5 + H2O
-
-
-
-
?
DELTA7-avenasterol + O2 + ferrocytochrome b5
DELTA5,7-avenasterol + H2O + ferricytochrome b5
-
-
-
-
?
DELTA7-campesterol + O2 + ferrocytochrome b5
DELTA5,7-campesterol + H2O + ferricytochrome b5
-
-
-
-
?
DELTA7-sitosterol + O2 + ferrocytochrome b5
DELTA5,7-sitosterol + H2O + ferricytochrome b5
-
-
-
-
?
DELTA7-sitoststigmast-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+
stigmast-5,7-dien-3beta-ol + ferricytochrome b5 + H2O
-
-
-
-
?
DELTA7-sterol + ferrocytochrome b5 + O2 + H+
DELTA5,7-sterol + ferricytochrome b5 + H2O
-
-
-
-
?
episterol + ferrocytochrome b5 + O2 + H+
? + ferricytochrome b5 + H2O
-
-
-
-
?
episterol + ferrocytochrome b5 + O2 + H+
ergosta-5,7,24(24)-trien-3beta-ol + ferricytochrome b5 + H2O
-
-
-
-
?
episterol + ferrocytochrome b5 + O2 + H+
ergosta-5,7,24(28)-trien-3beta-ol + ferricyctochrome b5 + H2O
-
-
-
-
?
episterol + O2 + ferrocytochrome b5
DELTA5,7-episterol + H2O + ferricytochrome b5
-
-
-
-
?
ergosta-7,22-dien-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosta-5,7,22-trien-3beta-ol + ferricytochrome b5 + H2O
-
-
-
?
ergosta-7,22-dien-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosterol + ferricytochrome b5 + H2O
-
-
-
?
ergosta-7,24(28)-dien-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosta-5,7-dien-3beta-ol + ferricyctochrome b5 + H2O
-
-
-
-
?
ergosta-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosta-5,7-dien-3beta-ol + ferricyctochrome b5 + H2O
-
-
-
-
?
ergosta-8,22-dien-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosta-5,8,22-trien-3beta-ol + ferricyctochrome b5 + H2O
-
-
-
-
?
ergosta-trien-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosta-5,8,24(28)-trien-3beta-ol + ferricyctochrome b5 + H2O
-
-
-
-
?
ergosterol + ferrocytochrome b5 + O2 + H+
lanosterol + ferricyctochrome b5 + H2O
-
-
-
-
?
fecosterol + ferrocytochrome b5 + O2 + H+
ergosta-5,7,24(28)-trien-3beta-ol + ferricyctochrome b5 + H2O
-
-
-
-
?
lanosterol + ferrocytochrome b5 + O2 + H+
? + ferricytochrome b5 + H2O
lanosterol + ferrocytochrome b5 + O2 + H+
lanosta-5,8,24-trien-3beta-ol + ferricyctochrome b5 + H2O
-
-
-
-
?
lathosterol + ferrocytochrome b5 + O2 + H+
7-dehydrocholesterol + ferricytochrome b5 + H2O
-
-
-
-
?
lathosterol + ferrocytochrome b5 + O2 + H+
?
-
-
-
-
?
lathosterol + O2 + ferrocytochrome b5
7-dehydrocholesterol + H2O + ferricytochrome b5
-
-
-
-
?
stigmast-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+
stigmast-5,7-dien-3beta-ol + ferricyctochrome b5 + H2O
-
-
-
-
?
stigmasta-7,22-dien-3beta-ol + ferrocytochrome b5 + O2 + H+
stigmast-5,7,22-trien-3beta-ol + ferricyctochrome b5 + H2O
-
-
-
-
?
zymosterol + ferrocytochrome b5 + O2 + H+
cholesta-5,8,24-trien-3beta-ol + ferricyctochrome b5 + H2O
-
-
-
-
?
additional information
?
-
5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+

cholesta-5,7-dien-3beta-ol + 2 ferricytochrome b5 + 2 H2O
-
i.e. lathosterol
-
?
5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+
cholesta-5,7-dien-3beta-ol + 2 ferricytochrome b5 + 2 H2O
-
i.e. lathosterol
-
?
5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+
cholesta-5,7-dien-3beta-ol + 2 ferricytochrome b5 + 2 H2O
-
i.e. lathosterol
-
?
5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+
cholesta-5,7-dien-3beta-ol + 2 ferricytochrome b5 + 2 H2O
-
enzyme is rather a mixed function oxidase which requires O2 and NAD(P)H for activity, than a dehydrogenase
-
?
5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+
cholesta-5,7-dien-3beta-ol + 2 ferricytochrome b5 + 2 H2O
-
NADPH, 40% of activity with NADH
-
?
5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+
cholesta-5,7-dien-3beta-ol + 2 ferricytochrome b5 + 2 H2O
-
cholesterol biosynthesis
-
?
5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+
cholesta-5,7-dien-3beta-ol + 2 ferricytochrome b5 + 2 H2O
-
cholesterol biosynthesis
-
?
5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+
cholesta-5,7-dien-3beta-ol + 2 ferricytochrome b5 + 2 H2O
-
-
-
?
5alpha-ergost-7,24(241)-dien-3beta-ol + O2 + ferrocytochrome b5

ergosta-5,7,24(241)-trien-3beta-ol + H2O2 + ferricytochrome b5
-
-
-
?
5alpha-ergost-7,24(241)-dien-3beta-ol + O2 + ferrocytochrome b5
ergosta-5,7,24(241)-trien-3beta-ol + H2O2 + ferricytochrome b5
-
-
-
?
5alpha-ergosta-7,22-dien-3beta-ol + ferrocytochrome b5 + O2 + H+

ergosterol + ferricytochrome b5 + H2O
-
-
-
?
5alpha-ergosta-7,22-dien-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosterol + ferricytochrome b5 + H2O
-
-
-
?
5alpha-ergosta-7,24-dien-3beta-ol + ferrocytochrome b5 + O2 + H+

ergosta-5,7,24-trien-3beta-ol + ferricytochrome b5 + H2O
-
-
-
?
5alpha-ergosta-7,24-dien-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosta-5,7,24-trien-3beta-ol + ferricytochrome b5 + H2O
-
-
-
?
5alpha-ergosta-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+

ergosta-5,7-dien-3beta-ol + ferricytochrome b5 + H2O
-
-
-
?
5alpha-ergosta-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosta-5,7-dien-3beta-ol + ferricytochrome b5 + H2O
-
-
-
?
lanosterol + ferrocytochrome b5 + O2 + H+

? + ferricytochrome b5 + H2O
-
-
-
?
lanosterol + ferrocytochrome b5 + O2 + H+
? + ferricytochrome b5 + H2O
-
-
-
?
additional information

?
-
-
enzyme deficiency leads to lathosterolosis, a defect of cholesterol biosynthesis, phenotype, detailed overview
-
-
-
additional information
?
-
-
the enzyme is involved in the post-squalene part of cholesterol biosynthesis
-
-
-
additional information
?
-
-
no activity with 4alpha-methyl-5alpha-cholest-7-en-3beta-ol, 4alpha,14alpha-dimethyl-5alpha-cholest-7-en-3beta-ol, cholestan-3beta-ol and cholest-8-en-3beta-ol
-
-
-
additional information
?
-
-
the specificity of maize C5(6)-desaturase favors DELTA7-sterols possessing a C24-methylene or ethylidene substituent compared to 24-ethyl-substituted DELTA7-sterols
-
-
-
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(3beta,24R)-ergost-7-en-3-ol + ferrocytochrome b5 + O2 + H+
(3beta,24R)-ergosta-5,7-dien-3-ol + ferricytochrome b5 + H2O
-
-
-
-
?
5alpha-cholest-22-en-3beta-ol + ferrocytochrmoe b5 + H+ + O2
cholesta-5,22-dien-3beta-ol + ferricytochrome b5 + 2 H2O
C4PFX1
-
-
-
?
5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+
cholesta-5,7-dien-3beta-ol + 2 ferricytochrome b5 + 2 H2O
5alpha-cholest-7-en-3beta-ol + ferrocytochrome b5 + H+ + O2
cholesta-5,7-dien-3beta-ol + ferricytochrmoe b5 + H2O
C4PFX1
-
-
-
?
5alpha-cholesta-7,22-dien-3beta-ol + ferrocytochrome b5 + H+ + O2
cholesta-5,7,22-trien-3beta-ol + ferricytochrome b5 + 2 H2O
C4PFX1
-
-
-
?
5alpha-cholestan-3beta-ol + ferrocytochrome b5 + H+ + O2
cholest-5-en-3beta-ol + ferricytochrome b5 + 2 H2O
C4PFX1
-
-
-
?
cholest-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+
cholest-5,7-dien-3beta-ol + ferricytochrome b5 + H2O
-
-
-
-
?
DELTA7-sitoststigmast-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+
stigmast-5,7-dien-3beta-ol + ferricytochrome b5 + H2O
-
-
-
-
?
DELTA7-sterol + ferrocytochrome b5 + O2 + H+
DELTA5,7-sterol + ferricytochrome b5 + H2O
-
-
-
-
?
episterol + ferrocytochrome b5 + O2 + H+
? + ferricytochrome b5 + H2O
-
-
-
-
?
lathosterol + ferrocytochrome b5 + O2 + H+
7-dehydrocholesterol + ferricytochrome b5 + H2O
-
-
-
-
?
lathosterol + O2 + ferrocytochrome b5
7-dehydrocholesterol + H2O + ferricytochrome b5
-
-
-
-
?
additional information
?
-
5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+

cholesta-5,7-dien-3beta-ol + 2 ferricytochrome b5 + 2 H2O
-
cholesterol biosynthesis
-
?
5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+
cholesta-5,7-dien-3beta-ol + 2 ferricytochrome b5 + 2 H2O
-
cholesterol biosynthesis
-
?
additional information

?
-
-
enzyme deficiency leads to lathosterolosis, a defect of cholesterol biosynthesis, phenotype, detailed overview
-
-
-
additional information
?
-
-
the enzyme is involved in the post-squalene part of cholesterol biosynthesis
-
-
-
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(3S,20S)-20-N-(2-methylpropyl)carbamoylpregn-7-en-3beta-ol
-
; specific
(3S,20S)-20-N-(2-methylpropyl)carbamoylpregn-7-en-3beta-yl acetate
-
; specific for the enzyme. Prodrug, transformed into the 3beta-hydroxy derivative under in vitro conditions
(3S,20S)-20-N-butylcarbamoylpregn-7-en-3beta-ol
-
; specific
(3S,20S)-20-N-butylcarbamoylpregn-7-en-3beta-yl acetate
-
; specific for the enzyme. Prodrug, transformed into the 3beta-hydroxy derivative under in vitro conditions
(3S,20S)-20-N-ethylcarbamoylpregn-7-en-3beta-ol
-
-
(3S,20S)-20-N-ethylcarbamoylpregn-7-en-3beta-yl acetate
-
-
(3S,20S)-20-N-pentylcarbamoylpregn-7-en-3beta-ol
-
; specific
(3S,20S)-20-N-pentylcarbamoylpregn-7-en-3beta-yl acetate
-
; specific for the enzyme. Prodrug, transformed into the 3beta-hydroxy derivative under in vitro conditions
(3S,20S)-20-N-propylcarbamoylpregn-7-en-3beta-ol
-
-
(3S,20S)-20-N-propylcarbamoylpregn-7-en-3beta-yl acetate
-
-
(3S,20S)-20-N-tert-butylcarbamoylpregn-7-en-3beta-ol
-
; specific
(3S,20S)-20-N-tert-butylcarbamoylpregn-7-en-3beta-yl acetate
-
; specific for the enzyme. Prodrug, transformed into the 3beta-hydroxy derivative under in vitro conditions
2-(4-phenethylpiperazin-1-yl)-1-(pyridine-3-yl)ethanol
-
average content of 7-dehydrocholesterol in human primary hepatocytes after 2-(4-phenethylpiperazin-1-yl)-1-(pyridine-3-yl)ethanol treatment is, 34.16 times higher than that in nontreated cells, indicating that DHCR7 is the major target (minor targets are human sterol DELTA14-reductase, sterol DELTA24-reductase, and sterol C5-desaturase). In vitro kinetic measurements show that the half-life of 2-(4-phenethylpiperazin-1-yl)-1-(pyridine-3-yl)ethanol is at least 4.3 h. 2-(4-phenethylpiperazin-1-yl)-1-(pyridine-3-yl)ethanol does not induce CYP3A4 mRNA nor enzyme activity
4,5-dihydroxy-1,3-benzene-disulfonic acid
-
trivial name tiron, 0.5 mM, 80% inhibition
alpha-(2,4-dichlorophenyl)-alpha-phenyl-5-pyrimidine methanol
-
trivial name triarimol, weak inhibition
anti-cytochrome b5 antibodies
-
0.5 mg/mg protein. 36% inhibition
-
bathophenanthroline
-
0.5 mM, 71% inhibition
dithiothreitol
-
1.0 mM, 55% inhibition
lathosterol side chain amides
-
synthesis and compound screening, influence of different sterol amides on inhibition of the enzyme, overview, lathosterol-derived amides with larger substituents, e.g. butyl, isobutyl, tert-butyl, pentyl, at the amide nitrogen are selective inhibitors of lathosterol oxidase, overview
-
menadione
-
32% residual actitivty at 0.05 mM
Salicylhydroxamic acid
-
-
salicylic hydroxamic acid
-
-
Tiron
-
21% residual activity at 1 mM
Triarimol
-
weak inhibition
1,10-phenanthroline

-
0.5 mM, 74% inhibition
CN-

0.003 mM, 50% inhibition of recombinant enzyme
CN-
-
0.5 mM, 95% inhibition
CN-
-
0.003-0015 mM, 50% inhibition
cyanide

-
cyanide
-
complete inhibition at 5 mM
additional information

-
cytotoxicity and inhibitor potencies for inhibition of total cholesterol biosynthesis, overview
-
additional information
-
the enzyme is not affected by N-ethylmaleimide and dithiothreitol
-
additional information
-
not inhibited by CO
-
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Rahier, A.; Smith, M.; Taton, M.
The role of cytochrome b5 in 4alpha-methyl-oxidation and C5(6) desaturation of plant sterol precursors
Biochem. Biophys. Res. Commun.
236
434-437
1997
Zea mays
brenda
Kawata, S.; Traskos, J.M.; Gaylor, J.L.
Microsomal enzymes of cholesterol biosynthesis from lanosterol. Purification and characterization of DELTA 7-sterol 5-desaturase of rat liver microsomes
J. Biol. Chem.
260
6609-6617
1985
Rattus norvegicus
brenda
Grinstead, G.F.; Gaylor, J.L.
Total enzymic synthesis of cholesterol from 4,4,14alpha-trimethyl-5alpha-cholesta-8,24-dien-3beta-ol. Solubilization, resolution, and reconstitution of DELTA 7-sterol 5-desaturase
J. Biol. Chem.
257
13937-13944
1982
Rattus norvegicus
brenda
Ishibashi, T.; Bloch, K.
Intermembrane transfer of 5alpha-cholest-7-en-3beta-ol. Facilitation by supernatant protein (SCP)
J. Biol. Chem.
256
12962-12967
1981
Rattus norvegicus
brenda
Dempsey, M.E.; McCoy, K.E.; Barker, H.N.
Large scale purification and structural characterization of squalene and sterol carrier protein
J. Biol. Chem.
256
1867-1873
1981
Rattus norvegicus
brenda
Mitropoulos, K.A.; Gibbons, G.F.
Effect of triarimol on cholesterol biosynthesis in rat-liver subcellular
Biochem. Biophys. Res. Commun.
71
892-900
1976
Rattus norvegicus
brenda
Husselstein, T.; Schaller, H.; Gachotte, D.; Benveniste, P.
DELTA7-sterol-C5-desaturase: molecular characterization and functional expression of wild-type and mutant alleles
Plant Mol. Biol.
39
891-906
1999
Arabidopsis thaliana, Nicotiana tabacum, Saccharomyces cerevisiae, Zea mays
brenda
Nishi, S.; Nishino, H.; Ishibashi, T.
cDNA cloning of the mammalian sterol C5-desaturase and the expression in yeast mutant
Biochim. Biophys. Acta
1490
106-108
2000
Homo sapiens, Mus musculus
brenda
Taton, M.; Husselstein, T.; Benveniste, P.; Rahier, A.
Role of highly conserved residues in the reaction catalyzed by recombinant DELTA7-sterol-C5(6)-desaturase studied by site-directed mutagenesis
Biochemistry
39
701-711
2000
Arabidopsis thaliana, Arabidopsis thaliana (Q39208)
brenda
Rahier, A.; Benveniste, P.; Husselstein, T.; Taton, M.
Biochemistry and site-directed mutational analysis of DELTA7-sterol-C5(6)-desaturase
Biochem. Soc. Trans.
28
799-803
2000
Zea mays
brenda
Sugawara, T.; Fujimoto, Y.; Ishibashi, T.
Molecular cloning and structural analysis of human sterol C5 desaturase
Biochim. Biophys. Acta
1533
277-284
2001
Homo sapiens
brenda
Rahier, A.
Deuterated DELTA7-cholestenol analogues as mechanistic probes for wild-type and mutated DELTA7-sterol-C5(6)-desaturase
Biochemistry
40
256-267
2001
Arabidopsis thaliana, Zea mays
brenda
Krakowiak, P.A.; Wassif, C.A.; Kratz, L.; Cozma, D.; Kovarova, M.; Harris, G.; Grinberg, A.; Yang, Y.; Hunter, A.G.; Tsokos, M.; Kelley, R.I.; Porter, F.D.
Lathosterolosis: an inborn error of human and murine cholesterol synthesis due to lathosterol 5-desaturase deficiency
Hum. Mol. Genet.
12
1631-1641
2003
Mus musculus
brenda
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