Information on EC 1.14.19.20 - DELTA7-sterol 5(6)-desaturase

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The enzyme appears in viruses and cellular organisms

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EC NUMBER
COMMENTARY hide
1.14.19.20
-
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RECOMMENDED NAME
GeneOntology No.
DELTA7-sterol 5(6)-desaturase
-
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REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a DELTA7-sterol + 2 ferrocytochrome b5 + O2 + 2 H+ = a DELTA5,7-sterol + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
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REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
redox reaction
reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
7-dehydroporiferasterol biosynthesis
-
-
Biosynthesis of antibiotics
-
-
Biosynthesis of secondary metabolites
-
-
cholesterol biosynthesis I
-
-
cholesterol biosynthesis II (via 24,25-dihydrolanosterol)
-
-
cholesterol biosynthesis III (via desmosterol)
-
-
ergosterol biosynthesis I
-
-
ergosterol biosynthesis II
-
-
Metabolic pathways
-
-
plant sterol biosynthesis
-
-
Steroid biosynthesis
-
-
cholesterol biosynthesis
-
-
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SYSTEMATIC NAME
IUBMB Comments
DELTA7-sterol,ferrocytochrome b5:oxygen oxidoreductase 5,6-dehydrogenating
This enzyme, found in eukaryotic organisms, catalyses the introduction of a double bond between the C5 and C6 carbons of the B ring of Delta7-sterols, to yield the corresponding Delta5,7-sterols. The enzymes from yeast, plants and vertebrates act on avenasterol, episterol, and lathosterol, respectively. The enzyme is located at the endoplasmic reticulum and is membrane bound.
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CAS REGISTRY NUMBER
COMMENTARY hide
37255-37-1
-
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
the enzyme is involved in ergosterol synthesis
physiological function
-
the enzyme is not essential for cell viability or the sparking function
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SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(24Z)-5alpha-stigmast-7,24(241)-dien-3beta-ol + O2 + reduced acceptor
(24Z)-stigmasta-5,7,24(241)-trien-3-beta-ol + acceptor + H2O
show the reaction diagram
-
-
-
?
(3beta,24R)-ergost-7-en-3-ol + ferrocytochrome b5 + O2 + H+
(3beta,24R)-ergosta-5,7-dien-3-ol + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
14-methylfecosterol + ferrocytochrome b5 + O2 + H+
14-methylergosta-5,8,24(28)-trien-3beta-ol + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
?
5alpha-cholest-22-en-3beta-ol + ferrocytochrmoe b5 + H+ + O2
cholesta-5,22-dien-3beta-ol + ferricytochrome b5 + 2 H2O
show the reaction diagram
-
-
-
?
5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+
cholesta-5,7-dien-3beta-ol + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
5alpha-cholest-7-en-3beta-ol + ferrocytochrmoe b5 + H+ + O2
cholesta-5,7-dien-3beta-ol + ferricytochrome b5 + H2O
show the reaction diagram
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
show the reaction diagram
-
-
-
?
5alpha-cholest-7-en-3beta-ol + ferrocytochrome b5 + H+ + O2
cholesta-5,7-dien-3beta-ol + ferricytochrome b5 + 2 H2O
show the reaction diagram
NADH is more efficient than NADPH
-
-
?
5alpha-cholest-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+
? + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
5alpha-cholesta-7,22-dien-3beta-ol + ferrocytochrome b5 + H+ + O2
cholesta-5,7,22-trien-3beta-ol + ferricytochrome b5 + 2 H2O
show the reaction diagram
-
-
-
?
5alpha-cholestan-3beta-ol + ferrocytochrome b5 + H+ + O2
cholest-5-en-3beta-ol + ferricytochrome b5 + 2 H2O
show the reaction diagram
-
-
-
?
5alpha-ergost-7,24(241)-dien-3beta-ol + O2 + ferrocytochrome b5
ergosta-5,7,24(241)-trien-3beta-ol + H2O2 + ferricytochrome b5
show the reaction diagram
5alpha-ergosta-7,22-dien-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosterol + ferricytochrome b5 + H2O
show the reaction diagram
5alpha-ergosta-7,24-dien-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosta-5,7,24-trien-3beta-ol + ferricytochrome b5 + H2O
show the reaction diagram
5alpha-ergosta-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosta-5,7-dien-3beta-ol + ferricytochrome b5 + H2O
show the reaction diagram
apinasterol + ferrocytochrome b5 + O2 + H+
stigmast-5,7,22-trien-3beta-ol + ferricyctochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
avenasterol + ferrocytochrome b5 + O2 + H+
?
show the reaction diagram
-
-
-
-
?
cholest-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+
cholest-5,7-dien-3beta-ol + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
DELTA7-avenasterol + O2 + ferrocytochrome b5
DELTA5,7-avenasterol + H2O + ferricytochrome b5
show the reaction diagram
-
-
-
-
?
DELTA7-campesterol + O2 + ferrocytochrome b5
DELTA5,7-campesterol + H2O + ferricytochrome b5
show the reaction diagram
-
-
-
-
?
DELTA7-sitosterol + O2 + ferrocytochrome b5
DELTA5,7-sitosterol + H2O + ferricytochrome b5
show the reaction diagram
-
-
-
-
?
DELTA7-sitoststigmast-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+
stigmast-5,7-dien-3beta-ol + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
DELTA7-sterol + ferrocytochrome b5 + O2 + H+
DELTA5,7-sterol + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
episterol + ferrocytochrome b5 + O2 + H+
? + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
episterol + ferrocytochrome b5 + O2 + H+
ergosta-5,7,24(24)-trien-3beta-ol + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
episterol + ferrocytochrome b5 + O2 + H+
ergosta-5,7,24(28)-trien-3beta-ol + ferricyctochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
episterol + O2 + ferrocytochrome b5
DELTA5,7-episterol + H2O + ferricytochrome b5
show the reaction diagram
-
-
-
-
?
ergosta-7,22-dien-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosta-5,7,22-trien-3beta-ol + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
?
ergosta-7,22-dien-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosterol + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
?
ergosta-7,24(28)-dien-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosta-5,7-dien-3beta-ol + ferricyctochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
ergosta-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosta-5,7-dien-3beta-ol + ferricyctochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
ergosta-8,22-dien-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosta-5,8,22-trien-3beta-ol + ferricyctochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
ergosta-trien-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosta-5,8,24(28)-trien-3beta-ol + ferricyctochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
ergosterol + ferrocytochrome b5 + O2 + H+
lanosterol + ferricyctochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
fecosterol + ferrocytochrome b5 + O2 + H+
ergosta-5,7,24(28)-trien-3beta-ol + ferricyctochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
lanosterol + ferrocytochrome b5 + O2 + H+
? + ferricytochrome b5 + H2O
show the reaction diagram
lanosterol + ferrocytochrome b5 + O2 + H+
lanosta-5,8,24-trien-3beta-ol + ferricyctochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
lathosterol + ferrocytochrome b5 + O2 + H+
7-dehydrocholesterol + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
lathosterol + ferrocytochrome b5 + O2 + H+
?
show the reaction diagram
-
-
-
-
?
lathosterol + O2 + ferrocytochrome b5
7-dehydrocholesterol + H2O + ferricytochrome b5
show the reaction diagram
-
-
-
-
?
stigmast-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+
stigmast-5,7-dien-3beta-ol + ferricyctochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
zymosterol + ferrocytochrome b5 + O2 + H+
cholesta-5,8,24-trien-3beta-ol + ferricyctochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
additional information
?
-
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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
(3beta,24R)-ergost-7-en-3-ol + ferrocytochrome b5 + O2 + H+
(3beta,24R)-ergosta-5,7-dien-3-ol + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
5alpha-cholest-22-en-3beta-ol + ferrocytochrmoe b5 + H+ + O2
cholesta-5,22-dien-3beta-ol + ferricytochrome b5 + 2 H2O
show the reaction diagram
C4PFX1
-
-
-
?
5alpha-cholest-7-en-3beta-ol + 2 ferrocytochrome b5 + O2 + 2 H+
cholesta-5,7-dien-3beta-ol + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
5alpha-cholest-7-en-3beta-ol + ferrocytochrome b5 + H+ + O2
cholesta-5,7-dien-3beta-ol + ferricytochrmoe b5 + H2O
show the reaction diagram
C4PFX1
-
-
-
?
5alpha-cholesta-7,22-dien-3beta-ol + ferrocytochrome b5 + H+ + O2
cholesta-5,7,22-trien-3beta-ol + ferricytochrome b5 + 2 H2O
show the reaction diagram
C4PFX1
-
-
-
?
5alpha-cholestan-3beta-ol + ferrocytochrome b5 + H+ + O2
cholest-5-en-3beta-ol + ferricytochrome b5 + 2 H2O
show the reaction diagram
C4PFX1
-
-
-
?
cholest-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+
cholest-5,7-dien-3beta-ol + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
DELTA7-sitoststigmast-7-en-3beta-ol + ferrocytochrome b5 + O2 + H+
stigmast-5,7-dien-3beta-ol + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
DELTA7-sterol + ferrocytochrome b5 + O2 + H+
DELTA5,7-sterol + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
episterol + ferrocytochrome b5 + O2 + H+
? + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
lathosterol + ferrocytochrome b5 + O2 + H+
7-dehydrocholesterol + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
-
?
lathosterol + O2 + ferrocytochrome b5
7-dehydrocholesterol + H2O + ferricytochrome b5
show the reaction diagram
-
-
-
-
?
additional information
?
-
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome b5
-
NAD(P)H
NADPH
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METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Iron
required
additional information
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(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
1,10-phenanthroline
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
cyanide
cyctochrome c
-
-
-
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
additional information
-
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
squalene and sterol carrier protein
-
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.032 - 0.244
5alpha-Cholest-7-en-3beta-ol
0.08
apinasterol
-
at pH 7.6 and 30°C
-
0.14
avenasterol
-
at pH 7.6 and 30°C
0.0105
episterol
-
at pH 7.6 and 30°C
0.115
lathosterol
-
at pH 7.6 and 30°C
0.67
stigmast-7-en-3beta-ol
-
at pH 7.6 and 30°C
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.00033
(3S,20S)-20-N-(2-methylpropyl)carbamoylpregn-7-en-3beta-ol
Homo sapiens
-
inhibition of total cholesterol prduction
0.00045
(3S,20S)-20-N-(2-methylpropyl)carbamoylpregn-7-en-3beta-yl acetate
Homo sapiens
-
inhibition of total cholesterol prduction
0.0007
(3S,20S)-20-N-butylcarbamoylpregn-7-en-3beta-ol
Homo sapiens
-
inhibition of total cholesterol prduction
0.00091
(3S,20S)-20-N-butylcarbamoylpregn-7-en-3beta-yl acetate
Homo sapiens
-
inhibition of total cholesterol prduction
0.00116
(3S,20S)-20-N-pentylcarbamoylpregn-7-en-3beta-ol
Homo sapiens
-
inhibition of total cholesterol prduction
0.0011
(3S,20S)-20-N-pentylcarbamoylpregn-7-en-3beta-yl acetate
Homo sapiens
-
inhibition of total cholesterol prduction
0.00105
(3S,20S)-20-N-tert-butylcarbamoylpregn-7-en-3beta-ol
Homo sapiens
-
inhibition of total cholesterol prduction
0.00095
(3S,20S)-20-N-tert-butylcarbamoylpregn-7-en-3beta-yl acetate
Homo sapiens
-
inhibition of total cholesterol prduction
2
1,10-phenanthroline
Zea mays
-
at pH 7.6 and 30°C
0.015
cyanide
Zea mays
-
at pH 7.6 and 30°C
0.008
cyctochrome c
Zea mays
-
at pH 7.6 and 30°C
-
0.5
Salicylhydroxamic acid
Zea mays
-
at pH 7.6 and 30°C
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SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0013
-
crude enzyme, at pH 8.0 and 37°C
0.022
-
after 17.7fold purification, at pH 8.0 and 37°C
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
primary hepatocytes are used for analysis
Manually annotated by BRENDA team
-
mRNA expression
Manually annotated by BRENDA team
-
mRNA expression
Manually annotated by BRENDA team
-
mRNA expression
Manually annotated by BRENDA team
-
-
Manually annotated by BRENDA team
-
mRNA expression
Manually annotated by BRENDA team
-
mRNA expression
Manually annotated by BRENDA team
-
mRNA expression
Manually annotated by BRENDA team
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30000
x * 30000, SDS-PAGE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 30000, SDS-PAGE
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GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
extremely labile
-
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STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
0°C, 24 h, 30% loss of activity
-
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Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
partial purification by DEAE cellulose column chromatography and 6-amino-hexyl-Sepharose column chromatography
-
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
; expression in null mutant erg3 of Saccharomyces cerevisiae
expressed in a Saccharomyces cerevisiae erg3-deficient mutant strain
expressed in an C-5(6) sterol desaturase erg3-deficient mutant of Saccharomyces cerevisia
expressed in an erg3-defective mutant of Saccharomyces crevisiae
-
expressed in Arabidopsis thaliana deficient in DELTA7-sterol-C-5-desaturase
-
expressed in Saccharomyces cerevisiae strain erg3
-
expression in Saccharomyces cerevisiae erg3 mutant
wild-type enzyme and ste1 mutant enzyme expressed in Sacharomyces cerevisiae erg3 mutant, wild-type enzyme overexpressed in Arabidopsis ste1 mutant
-
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
G234A
inactive mutant enzyme; no activity
G234D
2% of wild-type activity; low activity
H147E
inactive mutant enzyme; no activity
H147L
inactive mutant enzyme; no activity
H151E
inactive mutant enzyme; no activity
H151l
inactive mutant enzyme; no activity
H161E
inactive mutant enzyme; no activity
H161L
inactive mutant enzyme; no activity
H164L
inactive mutant enzyme; no activity
H165L
inactive mutant enzyme; no activity
H203L
13% of wild-type activity; reduced activity
H222E
6% of wild-type activity; reduced activity
H222L
inactive mutant enzyme; no activity
H238E
inactive mutant enzyme; no activity
H238L
inactive mutant enzyme; no activity
H241L
inactive mutant enzyme; no activity
H242L
inactive mutant enzyme; no activity
K115L
2times higher activity than wild-type; Km-value for 5alpha-cholest-7-en-3beta-ol is 2.8fold higher than that of wild-type activity
P175A
as active as wild-type enzyme; wild-type activity
P175V
4times higher activity than wild-type; Km-value for 5alpha-cholest-7-en-3beta-ol is 2.7fold higher than that of wild-type activity
P201A
20% of wild-type activity; 25% of wild-type activity
T114I
wild-type activity
T114I |
Km-value for 5alpha-cholest-7-en-3beta-ol is 7.5fold higher than that of wild-type activity
T114S
28times higher activity than wild-type; Km-value for 5alpha-cholest-7-en-3beta-ol is 7.6fold higher than that of wild-type activity
L193R
the mutation impairs enzyme function
additional information
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.19.20)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)