Information on EC 1.3.1.72 - DELTA24-sterol reductase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
1.3.1.72
-
RECOMMENDED NAME
GeneOntology No.
DELTA24-sterol reductase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
5alpha-cholest-7-en-3beta-ol + NADP+ = 5alpha-cholesta-7,24-dien-3beta-ol + NADPH + H+
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
-
-
-
-
redox reaction
-
-
-
-
reduction
-
-
-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
cholesterol biosynthesis I
-
-
cholesterol biosynthesis II (via 24,25-dihydrolanosterol)
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-
cholesterol biosynthesis III (via desmosterol)
-
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cholesterol biosynthesis
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Steroid biosynthesis
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Metabolic pathways
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Biosynthesis of secondary metabolites
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SYSTEMATIC NAME
IUBMB Comments
sterol:NADP+ DELTA24-oxidoreductase
Acts on a range of steroids with a 24(25)-double bond, including lanosterol, desmosterol and zymosterol.
CAS REGISTRY NUMBER
COMMENTARY hide
9033-57-2
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
silkworm
-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
tobacco hornworm
-
-
Manually annotated by BRENDA team
hybrid Nongda 3138
SwissProt
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
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
4,4-dimethyl-5alpha-cholesta-8,14,24-trien-3beta-ol + NADPH
4,4-dimethyl-5alpha-cholesta-8,14-dien-3beta-ol + NADP+
show the reaction diagram
-
-
-
?
4,4-dimethyl-5alpha-cholesta-8,24-dien-3beta-ol + NADPH
4,4-dimethyl-5alpha-cholesta-8-en-3beta-ol + NADP+
show the reaction diagram
5alpha-cholest-7-en-3beta-ol + NADP+
5alpha-cholesta-7,24-dien-3beta-ol + NADPH + H+
show the reaction diagram
-
-
-
-
r
5alpha-cholesta-7,24-dien-3beta-ol + NADPH
5alpha-cholest-7-en-3beta-ol + NADP+
show the reaction diagram
5alpha-cholesta-7,24-dien-3beta-ol + NADPH
5alpha-cholesta-7-en-3beta-ol + NADP+
show the reaction diagram
7-dehydrodesmosterol + NADPH
7-dehydrocholesterol + NADP+
show the reaction diagram
-
-
-
?
cholesta-5,7,24-trien-3beta-ol + NADPH
cholest-5,7-dien-3beta-ol + NADP+
show the reaction diagram
cholesta-5,7,24-trien-3beta-ol + NADPH + H+
cholesta-5,7-dien-3beta-ol + NADP+
show the reaction diagram
-
-
-
-
?
cycloartenol + NADPH
cycloartanol + NADP+
show the reaction diagram
-
-
-
?
desmosterol + FADH2
cholesterol + FAD + H+
show the reaction diagram
-
-
-
?
desmosterol + NADPH
cholesterol + NADP+
show the reaction diagram
lanosterol + NADPH
24-dihydrolanosterol + NADP+
show the reaction diagram
lanosterol + NADPH
4,4,14alpha-trimethyl-5alpha-cholesta-8-en-3beta-ol + NADP+
show the reaction diagram
lanosterol + NADPH + H+
24-dihydrolanosterol + NADP+
show the reaction diagram
-
-
-
?
zymosterol + NADPH
5alpha-cholesta-8-en-3beta-ol + NADP+
show the reaction diagram
additional information
?
-
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
5alpha-cholest-7-en-3beta-ol + NADP+
5alpha-cholesta-7,24-dien-3beta-ol + NADPH + H+
show the reaction diagram
-
-
-
-
r
5alpha-cholesta-7,24-dien-3beta-ol + NADPH
5alpha-cholest-7-en-3beta-ol + NADP+
show the reaction diagram
5alpha-cholesta-7,24-dien-3beta-ol + NADPH
5alpha-cholesta-7-en-3beta-ol + NADP+
show the reaction diagram
cholesta-5,7,24-trien-3beta-ol + NADPH
cholest-5,7-dien-3beta-ol + NADP+
show the reaction diagram
desmosterol + NADPH
cholesterol + NADP+
show the reaction diagram
lanosterol + NADPH
24-dihydrolanosterol + NADP+
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
NADPH
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(2S)-2-((3S,5S,10S,13R,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-N-methylpropanamide
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1 microM, 58% inhibition of total cholesterol production. Acts both on sterol reductoase and lathosterol oxidase
(2S)-2-((3S,5S,10S,13R,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-N-propylpropanamide
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1 microM, 45% inhibition of total cholesterol production. Acts both on sterol reductoase and lathosterol oxidase
(2S)-2-((3S,5S,10S,13R,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)propanamide
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1 microM, 75% inhibition of total cholesterol production
(2S)-N-ethyl-2-((3S,5S,10S,13R,17R)-3-hydroxy-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)propanamide
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1 microM, 61% inhibition of total cholesterol production
(3S,5S,10S,13R,17R)-10,13-dimethyl-17-((S)-1-(methylamino)-1-oxopropan-2-yl)-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
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1 microM, 84% inhibition of total cholesterol production. Acts both on sterol reductoase and lathosterol oxidase
(3S,5S,10S,13R,17R)-10,13-dimethyl-17-((S)-1-oxo-1-(propylamino)propan-2-yl)-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
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1 microM, 71% inhibition of total cholesterol production. Acts both on sterol reductoase and lathosterol oxidase
(3S,5S,10S,13R,17R)-17-((S)-1-(ethylamino)-1-oxopropan-2-yl)-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
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1 microM, 97% inhibition of total cholesterol production
(3S,5S,10S,13R,17R)-17-((S)-1-amino-1-oxopropan-2-yl)-10,13-dimethyl-2,3,4,5,6,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl acetate
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1 microM, 94% inhibition of total cholesterol production
24(R,S),25-epimino-lanosterol
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iminiolanosterol, IL, potent inhibitor, IC50: 0.002 mM
24(S),25-epoxycholesterol
25-Azacholesterol
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3-beta-(2-(diethylamino)ethoxy)androst-5-en-17-one
5,22-cholestedien-3beta-ol
azasteroids
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mechanism of inhibition
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brassicasterol
Calmodulin antagonists
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ergosterol
N-(6-aminohexyl)-5-chloro-1-naphthalene sulfonamide
stigmasterol
tamoxifen
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inhibition mechanism and pattern, uncompetitive, 50% inhibition at 0.004 mM, cytotoxic in vivo, inhibitory effect on th whole cholesterol biosynthetic pathway, overview
Trifluoperazine
Triparanol
additional information
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cholesterol
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high levels of DHCR24 are associated with elevated cholesterol concentrations
cholestyramine
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120fold induction and activation by feeding 5% cholestyramine plus 0.1% lovastatin, CL-diet, and by modulating diurnal variation
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CO
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substrate lanosterol: required to inhibit 14alpha-methyl demethylase, 14alpha-demethylation of lanosterol. 14alpha-methyl demethylase activity is dominant over 24-reductase activity, and blockade or removal of 14alpha-methyl demethylase activity is absolutely required for the detection of maximal 24-reductase activity when lanosterol substrate is present. 24-reductase activity is activated in time-dependent manner when 14alpha-methyl demethylase is blocked by CO treatment
FAD
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activate 2fold when added to the assay
H2O2
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DHCR24 mRNA levels increase in response to oxidative stress (0.1 mM H2O2) in a time-dependent manner, reaching the maximum after 4 h
ketoconazole
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substrate lanosterol: dose-dependent activation, less effective than miconazole, required to inhibit 14alpha-methyl demethylase, 14alpha-demethylation of lanosterol. 14alpha-methyl demethylase activity is dominant over 24-reductase activity, and blockade or removal of 14alpha-methyl demethylase activity is absolutely required for the detection of maximal 24-reductase activity when lanosterol substrate is present
lovastatin
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120fold induction and activation by feeding 5% cholestyramine plus 0.1% lovastatin, CL-diet, and by modulating diurnal variation
miconazole
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substrate lanosterol: dose-dependent activation, maximum activation with about 0.01 mM miconazole, required to inhibit 14alpha-methyl demethylase, 14alpha-demethylation of lanosterol. 14alpha-methyl demethylase activity is dominant over 24-reductase activity, and blockade or removal of 14alpha-methyl demethylase activity is absolutely required for the detection of maximal 24-reductase activity when lanosterol substrate is present
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.018 - 0.109
4,4',14alpha-trimethyl-5alpha-cholesta-8,24-dien-3beta-ol
0.0026 - 0.163
5alpha-cholesta-5,24-dien-3beta-ol
0.037
5alpha-cholesta-7,24-dien-3beta-ol
-
-
0.176
5alpha-cholesta-8,24-dien-3beta-ol
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zymosterol
0.033
Cycloartenol
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-
26.3
desmosterol
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pH 7.6, 37°C
additional information
additional information
-
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.000157
3-beta-(2-(diethylamino)ethoxy)androst-5-en-17-one
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-
0.0033
5,22-cholestedien-3beta-ol
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pH 7.6, 37°C
0.043
brassicasterol
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pH 7.6, 37°C
0.037
ergosterol
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pH 7.6, 37°C
0.041
stigmasterol
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pH 7.6, 37°C
0.0041
tamoxifen
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-
0.000523
Triparanol
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-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.002
24(R,S),25-epimino-lanosterol
Manduca sexta
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iminiolanosterol, IL, potent inhibitor, IC50: 0.002 mM
0.00015
3-beta-(2-(diethylamino)ethoxy)androst-5-en-17-one
Rattus norvegicus
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U18666A, non-competitive inhibition, Ki: 0.000157 mM, IC50 about 0.00015 mM, 690fold higher affinity for the enzyme than substrate lanosterol
0.0008
Triparanol
Rattus norvegicus
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non-competitive inhibition, specific inhibitor, Ki: 0.000523 mM, IC50 about 0.0008 mM, 208fold higher affinity for the enzyme than substrate lanosterol
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0015
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substrate: 5alpha-cholesta-7,24-dien-3beta-ol
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
6.2
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assay at, anaerobically
7.2
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assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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intestinal mucosa cells
Manually annotated by BRENDA team
abundantly expressed throughout the epidermis except for the stratum corneum and in hair follicles
Manually annotated by BRENDA team
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fibroblast from skin
Manually annotated by BRENDA team
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BE(2)C cell line
Manually annotated by BRENDA team
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a human hepatoblastoma-derived cell line
Manually annotated by BRENDA team
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human skin fibroblast
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
a predicted transmembrane (TM) domain-deleted DHCR24 mutation is localized to the cytoplasm
Manually annotated by BRENDA team
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
60000
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SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
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x * 60100, sequence calculation
additional information
enzyme secondary structure
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
enzyme possesses a potential N-terminal secretory signal
OXIDATION STABILITY
ORGANISM
UNIPROT
LITERATURE
seladin-1 expression is up-regulated in an acute response and down-regulated in a chronic response to oxidative stress
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688975
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed as a EGFP-fusion protein in murine neuroblastoma cell line N2A
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expressed in CHO cells
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expressed in Mus musculus embryonic fibroblasts and PC-12 cells infected with adenovirus
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gene DHCR24, DNA and amino acid sequence determination and analysis of wild-type and natural desmosterolysis mutant genes, chromosomal mapping to 1p31.1-p33, functional expression of wild-type and mutant enzymes in Saccharomyces cerevisiae
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gene ZmDWF1, single copy gene, DNA and amino acid sequence determination and analysis, cloning of a plant expression vector for construction of transgenic plants
overexpressed in ATDC-5 cells
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quantitative real-time PCR DHCR24 expression analysis
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RzM6-0d cells are transduced with DHCR24 lentivirus. Expression of DHCR24 from pGEM-T easy vector via in vitro translation using reticulocyte lysate. Expression of HA- or FLAG-tagged DHCR24 in RzM6 or HepG2 cells. Expression of GFP- and FLAG-tagged DHCR24 in 293FT cells
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
activation of constitutive androstane receptor (CAR) in cultured human hepatocytes increases mRNA levels of mouse Dhcr24 and human DHCR24. A CAR-responsive element is identified in the promoter of human DHCR24
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activation of constitutive androstane receptor (CAR) in mouse livers increases mRNA levels of mouse Dhcr24 and human DHCR24
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expression of DHCR24 is mediated by two sterol regulatory elements (SREs) in the promoter of the gene, assisted by two nearby NF-Y binding sites
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hepatitis C virus induces the DHCR24 overexpression in human hepatocytes
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
N294T/K306N
Y471S
decreased activity
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
agriculture
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inhibition of phytosterol metabolism to cholesterol by interfering with DELTA24-sterol reductase activity presents a unique target site that might be exploited further as a selective, biorational insect-control technology
medicine
DHCR24 plays crucial role for skin development and its proper function