Information on EC 1.14.13.70 - sterol 14alpha-demethylase

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

EC NUMBER
COMMENTARY hide
1.14.13.70
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RECOMMENDED NAME
GeneOntology No.
sterol 14alpha-demethylase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
a 14alpha-methylsteroid + 3 O2 + 3 NADPH + 3 H+ = a Delta14-steroid + formate + 3 NADP+ + 4 H2O
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
demethylation
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14alpha-demethylation
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hydroxylation
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monooxygenation
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oxidation
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oxygenation
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redox reaction
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reduction
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
Biosynthesis of antibiotics
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Biosynthesis of secondary metabolites
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cholesterol biosynthesis
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Metabolic pathways
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plant sterol biosynthesis
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Steroid biosynthesis
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zymosterol biosynthesis
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SYSTEMATIC NAME
IUBMB Comments
sterol,NADPH:oxygen oxidoreductase (14-methyl cleaving)
This heme-thiolate (P-450) enzyme acts on a range of steroids with a 14alpha-methyl group, such as obtusifoliol and lanosterol. The enzyme catalyses two successive hydroxylations of the 14alpha-methyl group, followed by elimination as formate, leaving a 14(15) double bond.
CAS REGISTRY NUMBER
COMMENTARY hide
138674-19-8
deleted registry number
341989-59-1
deleted registry number
60063-87-8
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90463-45-9
deleted registry number
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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Manually annotated by BRENDA team
voriconazole-resistant clinical isolates and voriconazole-susceptible parent strain X26728
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Manually annotated by BRENDA team
isozymes CYP51A and CYP51B, i.e. AF51A and AF51B
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Manually annotated by BRENDA team
Candida albicans ATCC MYA.2876
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Swissprot
Manually annotated by BRENDA team
strain ATCC7661
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
higher plants
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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UniProt
Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
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Manually annotated by BRENDA team
Crantz
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Manually annotated by BRENDA team
fragment; field isolates from Georgia, which are demethylation inhibitor fungicides-sensitive or demethylation inhibitor fungicides-resistant, gene CYP51
UniProt
Manually annotated by BRENDA team
silencing of enzyme by potato virus X::Nt CYP51-1 transcripts, accumulation of obtusifoliol
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Manually annotated by BRENDA team
no activity in Escherichia coli
no endogenous sterol 14alpha-demethylase
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Manually annotated by BRENDA team
syn. Tapesia acuformis, cereal eyespot fungi, gene CYP51
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Manually annotated by BRENDA team
syn. Tapesia yallundae, cereal eyespot fungi, gene CYP51
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Manually annotated by BRENDA team
ram
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Manually annotated by BRENDA team
28 different species isolated from human lung
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Manually annotated by BRENDA team
strain BY4741
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Manually annotated by BRENDA team
strain FY1679
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Manually annotated by BRENDA team
L.
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Manually annotated by BRENDA team
L.
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Manually annotated by BRENDA team
gene CYP51
SwissProt
Manually annotated by BRENDA team
expression in Escherichia coli with tetrahistidine tag
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Manually annotated by BRENDA team
i.e. Antrodia camphorata, gene CYP51
UniProt
Manually annotated by BRENDA team
i.e. Antrodia camphorata, gene CYP51
UniProt
Manually annotated by BRENDA team
Zea mays LG11
LG11
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Manually annotated by BRENDA team
gene CYP51
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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
(3b,4a,5a)-4,14-dimethylcholest-8-en-3-ol + O2 + NADPH
? + formate + NADP+ + H2O
show the reaction diagram
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good substrate, 67% of activity compared to obtusifoliol
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?
14alpha-methyl-24,28-dihydrofecosterol + O2 + NADPH
? + formate + NADP+ + H2O
show the reaction diagram
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50% of activity compared to obtusifoliol
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?
14alpha-methylzymosterol + O2 + NADPH + H+
?
show the reaction diagram
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-
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?
2-phenylimidazole + NADPH + O2
?
show the reaction diagram
-
2-phenylimidazole binding causes thermally induced alterations in CYP51 active site structure and/or binding modes for the small ligand
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?
24(28)-methylene-24,25-dihydrolanosterol + NADPH + O2
4,4-dimethyl-ergosta-8,14,24(28)-trien-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
-
-
-
?
24,25-dihydrolanosterol + 2 O2 + NADPH + H+
4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol + formate + NADP+ + 2 H2O
show the reaction diagram
24,25-dihydrolanosterol + 3 O2 + 3 NADPH + 3 H+
(3beta,5alpha)-4,4-dimethylcholesta-8,14-dien-3-ol + formate + 3 NADP+ + 4 H2O
show the reaction diagram
24,25-dihydrolanosterol + NADPH + O2
?
show the reaction diagram
24,25-dihydrolanosterol + O2 + NADPH + H+
24,25-dihydro-4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
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?
24,25-dihydrolanosterol + O2 + NADPH + H+
?
show the reaction diagram
i.e. anosta-8-en-3ebta-ol
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?
24,28-dihydroobtusifoliol + O2 + NADPH
4alpha-methyl-5alpha-ergosta-8,14-dien-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
24-methylene-24,25-dihydrolanosterol + O2 + NADPH
4,4-dimethyl-ergosta-8,14,24(28)-trien-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
24-methylene-24,25-dihydrolanosterol + O2 + NADPH + H+
14alpha-demethyl-24-methylene-4alpha-methyl-5alpha-ergosta-8,14,24-trien-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
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-
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?
24-methylenedihydrolanosterol + NADPH + O2
?
show the reaction diagram
24-methylenedihydrolanosterol + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
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preferred substrate
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?
7-lanosten-3beta-ol + O2 + NADPH
4,4-dimethylcholesta-7,14-dien-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
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very low activity
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?
7-lanostene-3beta,32-diol + O2 + NADPH
4,4-dimethylcholesta-7,14-dien-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
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very low activity
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?
8-lanostene-3beta,32-diol + O2 + NADPH
4,4-dimethylcholesta-8,14-dien-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
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?
eburicol + 3 O2 + 3 NADPH + 3 H+
?
show the reaction diagram
eburicol + O2 + NADPH
? + formate + NADP+ + H2O
show the reaction diagram
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?
eburicol + O2 + NADPH + H+
2-(3-hydroxy-4,4,10,13-tetramethyl-2,3,4,5,6,7,10,11,12,13,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)-6-methyl-5-methylene-heptanoic acid + formate + NADP+ + H2O
show the reaction diagram
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?
eburicol + O2 + NADPH + H+
?
show the reaction diagram
estriol + NADPH + O2
?
show the reaction diagram
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?
estriol + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
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?
lanosterol + 2 NADPH + 2 H+ + 2 O2
4,4-dimethylzymosterol + formate + 2 NADP+ + 2 H2O
show the reaction diagram
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?
lanosterol + 2 O2 + NADPH + H+
4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol + formate + NADP+ + 2 H2O
show the reaction diagram
lanosterol + 3 O2 + 3 NADPH + 3 H+
4,4-dimethylcholesta-8,14,24-trienol + formate + NADP+ + H2O
show the reaction diagram
lanosterol + 3 O2 + 3 NADPH + 3 H+
?
show the reaction diagram
lanosterol + NADP+ + H2O
?
show the reaction diagram
lanosterol + NADPH + H+ + 2 O2
4,4-dimethylcholesta-8,14,24-trienol + formate + NADP+ + 2 H2O
show the reaction diagram
lanosterol + NADPH + O2
4,4-dimethylcholesta-8,14,24-trien-3-ol + NADP+ + H2O
show the reaction diagram
artificial fused enzymes have comparable activity to the reconstituted system. Reduction of CYP51 both in the fused enzyme and the reconstituted system is biphasic and consisted of an initial fast phase followed by a slow phase
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?
lanosterol + NADPH + O2
?
show the reaction diagram
lanosterol + NADPH + O2
? + NADP+ + H2O
show the reaction diagram
lanosterol + O2 + NADPH
? + formate + NADP+ + H2O
show the reaction diagram
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activity depends on presence of natural fusion protein ferredoxin
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?
lanosterol + O2 + NADPH + H+
4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
lanosterol + O2 + NADPH + H+
4,4-dimethyl-5alpha-cholesta-8,14,24-triene-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
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?
lanosterol + O2 + NADPH + H+
4,4-dimethylcholesta-8,14,24-trien-3-ol + NADP+ + H2O
show the reaction diagram
norlanosterol + NADPH + O2
?
show the reaction diagram
norlanosterol + O2 + NADPH + H+
?
show the reaction diagram
i.e. 4alpha,14alpha-dimethylcholesta-8,24-dien-3beta-ol
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?
obtusifoliol + NADPH + O2
4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
obtusifoliol + O2 + NADPH
4alpha-methyl-5alpha-ergosta-8,14,24(28)-trien-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
obtusifoliol + O2 + NADPH + H+
4alpha-methyl-5alpha-ergosta-8,14,24(28)-trien-3beta-ol + formate + NADP+ + 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
14alpha-methylzymosterol + O2 + NADPH + H+
?
show the reaction diagram
A2TEF2
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?
24,25-dihydrolanosterol + 2 O2 + NADPH + H+
4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol + formate + NADP+ + 2 H2O
show the reaction diagram
24,25-dihydrolanosterol + 3 O2 + 3 NADPH + 3 H+
(3beta,5alpha)-4,4-dimethylcholesta-8,14-dien-3-ol + formate + 3 NADP+ + 4 H2O
show the reaction diagram
24,25-dihydrolanosterol + NADPH + O2
?
show the reaction diagram
24,25-dihydrolanosterol + O2 + NADPH + H+
24,25-dihydro-4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
-
-
-
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?
24-methylenedihydrolanosterol + NADPH + O2
?
show the reaction diagram
eburicol + O2 + NADPH
? + formate + NADP+ + H2O
show the reaction diagram
-
-
-
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?
eburicol + O2 + NADPH + H+
?
show the reaction diagram
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?
lanosterol + 2 NADPH + 2 H+ + 2 O2
4,4-dimethylzymosterol + formate + 2 NADP+ + 2 H2O
show the reaction diagram
Q673E9
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?
lanosterol + 2 O2 + NADPH + H+
4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol + formate + NADP+ + 2 H2O
show the reaction diagram
lanosterol + 3 O2 + 3 NADPH + 3 H+
?
show the reaction diagram
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-
-
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?
lanosterol + NADP+ + H2O
?
show the reaction diagram
lanosterol + NADPH + H+ + 2 O2
4,4-dimethylcholesta-8,14,24-trienol + formate + NADP+ + 2 H2O
show the reaction diagram
lanosterol + NADPH + O2
?
show the reaction diagram
lanosterol + O2 + NADPH + H+
4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
lanosterol + O2 + NADPH + H+
4,4-dimethyl-5alpha-cholesta-8,14,24-triene-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
-
-
-
-
?
lanosterol + O2 + NADPH + H+
4,4-dimethylcholesta-8,14,24-trien-3-ol + NADP+ + H2O
show the reaction diagram
norlanosterol + NADPH + O2
?
show the reaction diagram
norlanosterol + O2 + NADPH + H+
?
show the reaction diagram
A2TEF2
i.e. 4alpha,14alpha-dimethylcholesta-8,24-dien-3beta-ol
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?
obtusifoliol + NADPH + O2
4alpha-methyl-5alpha-ergost-8,14,24(28)-trien-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
obtusifoliol + O2 + NADPH
4alpha-methyl-5alpha-ergosta-8,14,24(28)-trien-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
obtusifoliol + O2 + NADPH + H+
4alpha-methyl-5alpha-ergosta-8,14,24(28)-trien-3beta-ol + formate + NADP+ + H2O
show the reaction diagram
additional information
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome
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a cytochrome P450 enzyme
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cytochrome P450
Ferredoxin