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Information on EC 1.1.1.170 - 3beta-hydroxysteroid-4alpha-carboxylate 3-dehydrogenase (decarboxylating) for references in articles please use BRENDA:EC1.1.1.170Word Map on EC 1.1.1.170
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The enzyme appears in viruses and cellular organisms
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3beta-hydroxysteroid-4alpha-carboxylate 3-dehydrogenase (decarboxylating)
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a 3beta-hydroxysteroid-4alpha-carboxylate + NAD(P)+ = a 3-oxosteroid + CO2 + NAD(P)H
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cholesterol biosynthesis I
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cholesterol biosynthesis II (via 24,25-dihydrolanosterol)
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cholesterol biosynthesis III (via desmosterol)
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zymosterol biosynthesis
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cholesterol biosynthesis
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Biosynthesis of antibiotics
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3beta-hydroxysteroid-4alpha-carboxylate:NAD(P)+ 3-oxidoreductase (decarboxylating)
The enzyme catalyses the decarboxylation of the C-4 carbon and the dehydrogenation of a 3beta hydroxyl at the C-3 carbon of 3beta-hydroxysteroid-4alpha-carboxylates. It is involved in zymosterol and cholesterol biosynthesis.
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3beta-hydroxy-4alpha-methylcholestenecarboxylate 3-dehydrogenase (decarboxylating)
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3beta-hydroxy-4beta-methylcholestenoate dehydrogenase
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4alpha-carboxylic acid decarboxylase
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C-3 sterol dehydrogenase(C-4 decarboxylase)
sterol 4alpha-carboxylic decarboxylase
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sterol-4-alpha-carboxylate 3-dehydrogenase
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sterol-4-alpha-carboxylate-3-dehydrogenase
sterol-4alpha-carboxylate 3-dehydrogenase
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C-3 sterol dehydrogenase(C-4 decarboxylase)
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C-3 sterol dehydrogenase(C-4 decarboxylase)
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Erg26
Q5A1B0
gene name
Erg26p
Q5A1B0
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NSDHL
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sterol-4-alpha-carboxylate-3-dehydrogenase
Q5A1B0
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sterol-4-alpha-carboxylate-3-dehydrogenase
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sterol-4-alpha-carboxylate-3-dehydrogenase
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sterol-4-alpha-carboxylate-3-dehydrogenase
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Q5A1B0
UniProt
brenda
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brenda
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UniProt
brenda
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brenda
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UniProt
brenda
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brenda
I/LnJ and KK/HlJ inbred strains and cross breeds between KK/HlJ and I/LnJ
UniProt
brenda
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brenda
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UniProt
brenda
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malfunction
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mutations in NSDHL gene are associated with human CHILD syndrome, congenital hemidysplasia with ichthyosiform nevus and limb defects
malfunction
a I/LnJ-specific nonsynonymous polymorphism in X-linked Nsdhl, which codes for sterol-4-alpha-carboxylate 3-dehydrogenase in the cholesterol synthesis pathway, causes reduced HDL cholesterol levels in plasma
metabolism
the enzyme sterol-4-alpha-carboxylate 3-dehydrogenase is important in the cholesterol synthesis pathway
metabolism
Q5A1B0
the sterol-4-alpha-carboxylate-3-dehydrogenase is an essential enzyme in the ergosterol/cholesterol biosynthesis pathway
metabolism
the sterol-4-alpha-carboxylate-3-dehydrogenase is an essential enzyme in the ergosterol/cholesterol biosynthesis pathway
metabolism
the sterol-4-alpha-carboxylate-3-dehydrogenase is an essential enzyme in the ergosterol/cholesterol biosynthesis pathway
metabolism
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the sterol-4-alpha-carboxylate-3-dehydrogenase is an essential enzyme in the ergosterol/cholesterol biosynthesis pathway
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physiological function
Q5A1B0
the sterol-4-alpha-carboxylate-3-dehydrogenase is an essential enzyme in the ergosterol/cholesterol biosynthesis pathway
physiological function
the sterol-4-alpha-carboxylate-3-dehydrogenase is an essential enzyme in the ergosterol/cholesterol biosynthesis pathway
physiological function
the sterol-4-alpha-carboxylate-3-dehydrogenase is an essential enzyme in the ergosterol/cholesterol biosynthesis pathway
physiological function
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the sterol-4-alpha-carboxylate-3-dehydrogenase is an essential enzyme in the ergosterol/cholesterol biosynthesis pathway
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additional information
HDL and non-HDL lipid contents in different mouse genotypes and correlation to gene Nsdhl, overview
additional information
ERG26p structure homology modeling based on the crystal structure of Pseudomonas aeruginosa UDP-N-acetylglucosamine 4-epimerase complexed with UDP-N-acetylgalactosamine, PDB ID 1SB8
additional information
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ERG26p structure homology modeling based on the crystal structure of Pseudomonas aeruginosa UDP-N-acetylglucosamine 4-epimerase complexed with UDP-N-acetylgalactosamine, PDB ID 1SB8
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3beta-hydroxy-4alpha-methyl-5alpha-cholest-7-ene-4beta-carboxylate + NAD+
4alpha-methyl-5alpha-cholest-7-en-3-one + CO2 + NADH
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?
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-en-4alpha-oic acid + NAD+
4alpha-methyl-5alpha-cholest-7-en-3-one + CO2 + NADH
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no epimerization of 4beta-isomer into 4alpha-isomer
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ir
3beta-hydroxy-cholest-8,24-dien-4alpha-carboxylate + NAD+
4alpha-methyl-cholest-8,24-dien-3-one + CO2 + NADH
4alpha-carboxy-4beta-methyl-5alpha-cholesta-8,24-dien-3beta-ol + NADP+
3-dehydro-4-methylzymosterol + NADPH + CO2
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?
4alpha-carboxy-4beta-methyl-5alpha-cholesta-8-en-3beta-ol + NADP+
4alpha-methyl-5alpha-cholesta-8-en-3-one + NADPH + CO2
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enzyme is involved in the sequential removal of two C-4 methyl groups in post-squalene cholesterol biosynthesis
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?
4alpha-carboxy-5alpha-cholesta-8,24-dien-3beta-ol + NADP+
5alpha-cholesta-8,24-dien-3-one + NADPH + CO2
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?
4alpha-carboxy-5alpha-cholesta-8-en-3beta-ol + NADP+
5alpha-cholesta-8-en-3-one + CO2 + NADPH
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enzyme is involved in the sequential removal of two C-4 methyl groups in post-squalene cholesterol biosynthesis
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?
a 3beta-hydroxysteroid-4alpha-carboxylate + NAD(P)+
a 3-oxosteroid + CO2 + NAD(P)H
additional information
?
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involved in the removal of C-4 methyl groups in postsqualene cholesterol synthesis
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3beta-hydroxy-cholest-8,24-dien-4alpha-carboxylate + NAD+
4alpha-methyl-cholest-8,24-dien-3-one + CO2 + NADH
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?
3beta-hydroxy-cholest-8,24-dien-4alpha-carboxylate + NAD+
4alpha-methyl-cholest-8,24-dien-3-one + CO2 + NADH
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?
3beta-hydroxy-cholest-8,24-dien-4alpha-carboxylate + NAD+
4alpha-methyl-cholest-8,24-dien-3-one + CO2 + NADH
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?
a 3beta-hydroxysteroid-4alpha-carboxylate + NAD(P)+
a 3-oxosteroid + CO2 + NAD(P)H
Q5A1B0
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?
a 3beta-hydroxysteroid-4alpha-carboxylate + NAD(P)+
a 3-oxosteroid + CO2 + NAD(P)H
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?
a 3beta-hydroxysteroid-4alpha-carboxylate + NAD(P)+
a 3-oxosteroid + CO2 + NAD(P)H
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?
a 3beta-hydroxysteroid-4alpha-carboxylate + NAD(P)+
a 3-oxosteroid + CO2 + NAD(P)H
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?
a 3beta-hydroxysteroid-4alpha-carboxylate + NAD(P)+
a 3-oxosteroid + CO2 + NAD(P)H
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?
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3beta-hydroxy-4alpha-methyl-5alpha-cholest-7-ene-4beta-carboxylate + NAD+
4alpha-methyl-5alpha-cholest-7-en-3-one + CO2 + NADH
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?
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-en-4alpha-oic acid + NAD+
4alpha-methyl-5alpha-cholest-7-en-3-one + CO2 + NADH
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no epimerization of 4beta-isomer into 4alpha-isomer
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ir
a 3beta-hydroxysteroid-4alpha-carboxylate + NAD(P)+
a 3-oxosteroid + CO2 + NAD(P)H
additional information
?
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involved in the removal of C-4 methyl groups in postsqualene cholesterol synthesis
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a 3beta-hydroxysteroid-4alpha-carboxylate + NAD(P)+
a 3-oxosteroid + CO2 + NAD(P)H
Q5A1B0
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?
a 3beta-hydroxysteroid-4alpha-carboxylate + NAD(P)+
a 3-oxosteroid + CO2 + NAD(P)H
Q15738
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?
a 3beta-hydroxysteroid-4alpha-carboxylate + NAD(P)+
a 3-oxosteroid + CO2 + NAD(P)H
Q9R1J0
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?
a 3beta-hydroxysteroid-4alpha-carboxylate + NAD(P)+
a 3-oxosteroid + CO2 + NAD(P)H
P53199
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?
a 3beta-hydroxysteroid-4alpha-carboxylate + NAD(P)+
a 3-oxosteroid + CO2 + NAD(P)H
P53199
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?
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NAD+
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can not be replaced by NADP+
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5alpha-cholest-7-en-3-one
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2-9.3% inhibition between 16 and 130 nmol
5alpha-Cholest-7-en-3beta-ol
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15.5-65% inhibition between 30 and 260 nmol
Fe2+
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less than 25% inhibition at 1 mM
Zn2+
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marked inhibition between 0.1 and 1 mM
FR171456
Q5A1B0
a natural specific inhibitor of yeast Erg26p from Monodictys sp.. FR171456 is a natural product with cholesterol-lowering properties in animal models. FR171456 significantly alters the levels of cholesterol pathway intermediates in yeast cells. FR171456 causes significant growth inhibition of strain SC5314 at. Erg26p inhibition requires the 4alpha-carboxyl group of FR171456, substitution of the 4alpha-carboxylic group of FR171456 by a carbobenzylamido group (Compound-1) decreases inhibition
FR171456
a natural specific inhibitor of mammalian NSDHL from Monodictys sp.. FR171456 is a natural product with cholesterol-lowering properties in animal models. FR171456 significantly alters the levels of cholesterol pathway intermediates in human cells. R171456 inhibits an artificial Hepatitis C viral replicon, and has broad antifungal activity, suggesting potential additional utility as an anti-infective. In a screen to profile compound activity against 503 cancer cell lines only five cell lines are sensitive to FR171456 with IC50 values below 0.005 mM. Calcidiol, a cholesterol metabolite situated downstream of NSDHL, is decreased in a FR171456 dose-dependent manner, consistent with a reduction of cholesterol synthesis, and new derivatives of NSDHL substrates are deteremined in the cells that are no longer effective as substrates
FR171456
a natural specific inhibitor of yeast Erg26p from Monodictys sp.. Genomic profiling identifies Erg26p as the FR171456 target, the ERG26 heterozygous strain (erg26DELTA/ERG26) shows the most significant hypersensitivity to FR171456. FR171456 is a natural product with cholesterol-lowering properties in animal models. FR171456 significantly alters the levels of cholesterol pathway intermediates in yeast cells. FR171456 causes significant growth inhibition of strain BY4743 at concentrations up to 0.2 mM. Multiple mutations, e.g. Gly90Ser, in enzyme ERG26 confer resistance to FR171456 in growth and enzyme assays. FR171456 inhibits an artificial Hepatitis C viral replicon, and has broad antifungal activity, suggesting potential additional utility as an anti-infective. Erg26p inhibition requires the 4a-carboxyl group of FR171456, substitution of the 4alpha-carboxylic group of FR171456 by a carbobenzylamido group (Compound-1) decreases inhibition by 300fold. FR171456 docking into a homology model of Erg26p. Modelling FR171456 resistance mutations on Erg26p, overview
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0.007
3beta-hydroxy-4beta-methyl-5alpha-cholest-7-en-4alpha-oic acid
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0.55
3beta-hydroxy-cholest-8,24-dien-4alpha-carboxylate
pH 7.5, 30°C
additional information
additional information
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additional information
additional information
Michaelis-Menten kinetics
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additional information
additional information
Michaelis-Menten kinetics
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0.00135
FR171456
in vitro inhibition, pH 7.5, 30°C
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0.0000063 - 0.08
FR171456
0.0000063
FR171456
Homo sapiens
Q15738
in a Huh-7 cell-based assay, pH 7.5, 30°C
0.0022
FR171456
Saccharomyces cerevisiae
P53199
in vitro inhibition, pH 7.5, 30°C
0.036
FR171456
Homo sapiens
Q15738
in a K-562 cell-based assay, pH 7.5, 30°C
0.08
FR171456
Homo sapiens
Q15738
in a Hep-G2 cell-based assay, pH 7.5, 30°C
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7.5
assay at
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additional information
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acidic pH results in a very low decarboxylation rate
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30
assay at
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brenda
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brenda
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surface of
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additional information
ERG26p structure homology modeling based on the crystal structure of Pseudomonas aeruginosa UDP-N-acetylglucosamine 4-epimerase complexed with UDP-N-acetylgalactosamine, PDB ID 1SB8
additional information
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ERG26p structure homology modeling based on the crystal structure of Pseudomonas aeruginosa UDP-N-acetylglucosamine 4-epimerase complexed with UDP-N-acetylgalactosamine, PDB ID 1SB8
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phospholipoprotein
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presence of phosphatidylcholine and phosphatidylethanolamine, no loss of activity after removal of phospholipids
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4°C, 10 mM phosphate buffer, pH 7.4, no loss of activity within 2 weeks
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near homogeneity, chromatography techniques, sodium deoxycholate solubilization
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complementation of erg26 deficient Saccharomyces cerevisiae strain SDG200
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gene Nsdhl, located on the X-chromosome, genotyping in 233 mice from a F2 cross between KK/HlJ and I/LnJ
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A94T
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naturally occurring missense mutant, mutant is not able to complement erg26 deficiency in Saccharomyces cerevisiae strain SDG200
G280A
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loss of a HhaI restriction site
V53D
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naturally occurring missense mutant, mutant is not able to complement erg26 deficiency in Saccharomyces cerevisiae strain SDG200
Gly90Ser
naturally occuring mutation of ERG26 that confers resistance to inhibitor FR171456
Gly90Ser
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naturally occuring mutation of ERG26 that confers resistance to inhibitor FR171456
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additional information
multiple mutations in ERG26 confer resistance to inhibitor FR171456 in growth and enzyme assays. Some of these ERG26 mutations likely alter Erg26 binding to FR171456, based on a structure model of Erg26
additional information
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multiple mutations in ERG26 confer resistance to inhibitor FR171456 in growth and enzyme assays. Some of these ERG26 mutations likely alter Erg26 binding to FR171456, based on a structure model of Erg26
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ERG26_SCHPO
Schizosaccharomyces pombe (strain 972 / ATCC 24843)
340
38318
Swiss-Prot
ERG26_YEAST
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
349
38706
Swiss-Prot
HSDD1_ARATH
439
48125
Swiss-Prot
HSDD2_ARATH
564
61704
Swiss-Prot
HSDD3_ARATH
561
63033
Swiss-Prot
NSDHL_BOVIN
356
39902
Swiss-Prot
NSDHL_DICDI
328
36765
Swiss-Prot
NSDHL_HUMAN
373
41900
Swiss-Prot
NSDHL_MOUSE
362
40686
Swiss-Prot
NSDHL_RAT
362
40412
Swiss-Prot
M5C244_THACB
Thanatephorus cucumeris (strain AG1-IB / isolate 7/3/14)
420
45928
TrEMBL
G4I552_MYCRH
353
38667
TrEMBL
G6FS60_9CYAN
334
36355
TrEMBL
F6FRA2_ISOV2
Isoptericola variabilis (strain 225)
326
33983
TrEMBL
A0A2U3QJK7_9BACT
317
34470
TrEMBL
M2W461_GALSU
362
41040
TrEMBL
A0A142B9G9_9GAMM
368
41188
TrEMBL
G8P103_GRAMM
Granulicella mallensis (strain ATCC BAA-1857 / DSM 23137 / MP5ACTX8)
328
35585
TrEMBL
A0A0B2RS39_GLYSO
401
44397
TrEMBL
A0A0F8BTH9_CERFI
372
40567
TrEMBL
F4KUF8_HALH1
Haliscomenobacter hydrossis (strain ATCC 27775 / DSM 1100 / LMG 10767 / O)
335
37023
TrEMBL
A0A0B2PYF0_GLYSO
478
53844
TrEMBL
A0A0U0G794_STREE
328
37200
TrEMBL
A0A212KTW6_9CHLA
333
36660
TrEMBL
A0A061K302_ECOLX
304
33468
TrEMBL
A0A0D2JT94_9CHLO
236
25081
TrEMBL
K9XUI3_STAC7
Stanieria cyanosphaera (strain ATCC 29371 / PCC 7437)
1521
172594
TrEMBL
A0A2G9GG27_9LAMI
477
53435
TrEMBL
W1QJX5_OGAPD
Ogataea parapolymorpha (strain ATCC 26012 / BCRC 20466 / JCM 22074 / NRRL Y-7560 / DL-1)
349
38722
TrEMBL
A0A0N1HIU8_9ACTN
383
40452
TrEMBL
D5PFS6_9MYCO
368
40192
TrEMBL
A0A099KHW0_COLPS
365
40000
TrEMBL
A0A2X4E9K5_STRPO
327
36908
TrEMBL
G6G011_9CYAN
334
37079
TrEMBL
K0KBM1_WICCF
Wickerhamomyces ciferrii (strain F-60-10 / ATCC 14091 / CBS 111 / JCM 3599 / NBRC 0793 / NRRL Y-1031)
348
38904
TrEMBL
A0A1W1HEJ0_9DELT
329
36210
TrEMBL
A0A2I0ADF1_9ASPA
384
41885
TrEMBL
G0K3T9_STEMA
330
35442
TrEMBL
F0SPA9_RUBBR
Rubinisphaera brasiliensis (strain ATCC 49424 / DSM 5305 / JCM 21570 / NBRC 103401 / IFAM 1448)
332
36359
TrEMBL
G2Q2U8_MYCTT
Myceliophthora thermophila (strain ATCC 42464 / BCRC 31852 / DSM 1799)
375
41609
TrEMBL
G0QWJ3_ICHMG
Ichthyophthirius multifiliis (strain G5)
253
28658
TrEMBL
A0A0F4YEW5_TALEM
411
45674
TrEMBL
B9R8T2_RICCO
478
53538
TrEMBL
G0ATI5_9GAMM
396
42650
TrEMBL
A0A1W2TDW9_ROSNE
369
40860
TrEMBL
D7FKR6_ECTSI
348
38262
TrEMBL
F0T1U5_SYNGF
Syntrophobotulus glycolicus (strain DSM 8271 / FlGlyR)
329
37328
TrEMBL
A0A0X9LJ68_STREE
561
60646
TrEMBL
F9WZQ0_ZYMTI
Zymoseptoria tritici (strain CBS 115943 / IPO323)
385
42647
TrEMBL
A0A2H9ZX18_9ASPA
350
38911
TrEMBL
E7L6Y0_TRYCR
406
46052
TrEMBL
A2R589_ASPNC
Aspergillus niger (strain CBS 513.88 / FGSC A1513)
412
45622
TrEMBL
A0A099KV39_COLPS
390
42837
TrEMBL
A0A2P6PBT1_ROSCH
480
53880
TrEMBL
A0A0B2R9X9_GLYSO
149
16209
TrEMBL
A0A0B2SUH0_GLYSO
480
53888
TrEMBL
A0A2G9HLN1_9LAMI
425
46673
TrEMBL
F8ECA2_RUNSL
Runella slithyformis (strain ATCC 29530 / DSM 19594 / LMG 11500 / NCIMB 11436 / LSU 4)
332
37000
TrEMBL
A0A2I0AM64_9ASPA
480
53326
TrEMBL
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3beta-hydroxysteroid-4alpha-carboxylate 3-dehydrogenase (decarboxylating) deficiency
Analysis of Nsdhl-deficient embryos reveals a role for Hedgehog signaling in early placental development.
Carcinoma
Endogenous Sterol Metabolites Regulate Growth of EGFR/KRAS-Dependent Tumors via LXR.
Dermatitis, Exfoliative
Expression profile of NSDHL in human peripheral tissues.
Intellectual Disability
Analysis of hedgehog signaling in cerebellar granule cell precursors in a conditional Nsdhl allele demonstrates an essential role for cholesterol in postnatal CNS development.
Intellectual Disability
Hypomorphic temperature-sensitive alleles of NSDHL cause CK syndrome.
Neoplasms
Endogenous Sterol Metabolites Regulate Growth of EGFR/KRAS-Dependent Tumors via LXR.
Neoplasms
Targeting C4-demethylating genes in the cholesterol pathway sensitizes cancer cells to EGF receptor inhibitors via increased EGF receptor degradation.
Nevus
CHILD syndrome without hemidysplasia.
Nevus
Localization of mammalian NAD(P)H steroid dehydrogenase-like protein on lipid droplets.
Nevus
Mutations in the NSDHL gene, encoding a 3beta-hydroxysteroid dehydrogenase, cause CHILD syndrome.
Nevus
Targeting epidermal lipids for treatment of Mendelian disorders of cornification.
Placental Insufficiency
Significant contributions of the extraembryonic membranes and maternal genotype to the placental pathology in heterozygous Nsdhl deficient female embryos.
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Rahimtula, A.D.; Gaylor, J.L.
Investigation of the component reactions of oxidative sterol demethylation. Partial purification of a microsomal sterol 4alpha-carboxylic acid decarboxylase
J. Biol. Chem.
247
9-15
1972
Rattus sp.
brenda
Lucas, M.E.; Ma, Q.; Cunningham, D.; Peters, J.; Cattanach, B.; Bard, M.; Elmore, B.K.; Herman, G.E.
Identification of two novel mutations in the murine Nsdhl sterol dehydrogenase gene and development of a functional complementation assay in yeast
Mol. Genet. Metab.
80
227-233
2003
Mus musculus
brenda
Caldas, H.; Herman, G.E.
NSDHL, an enzyme involved in cholesterol biosynthesis, traffics through the Golgi and accumulates on ER membranes and on the surface of lipid droplets
Hum. Mol. Genet.
12
2981-91
2003
Homo sapiens
brenda
Gachotte, D.; Barbuch, R.; Gaylor, J.; Nickel, E.; Bard, M.
Characterization of the Saccharomyces cerevisiae ERG26 gene encoding the C-3 sterol dehydrogenase (C-4 decarboxylase) involved in sterol biosynthesis
Proc. Natl. Acad. Sci. USA
95
13794-9
1998
Saccharomyces cerevisiae
brenda
Bautz, D.J.; Broman, K.W.; Threadgill, D.W.
Identification of a novel polymorphism in X-linked sterol-4-alpha-carboxylate 3-dehydrogenase (Nsdhl) associated with reduced high-density lipoprotein cholesterol levels in I/LnJ mice
G3 (Bethesda)
3
1819-1825
2013
Mus musculus (Q9R1J0)
brenda
Helliwell, S.B.; Karkare, S.; Bergdoll, M.; Rahier, A.; Leighton-Davis, J.R.; Fioretto, C.; Aust, T.; Filipuzzi, I.; Frederiksen, M.; Gounarides, J.; Hoepfner, D.; Hofmann, A.; Imbert, P.E.; Jeker, R.; Knochenmuss, R.; Krastel, P.; Margerit, A.; Memmert, K.; Miault, C.V.; Movva, N.R.; Muller, A.; Naegeli, H.-U.; Oberer, L.; Prindle, V.; Riedl, R.; Schuierer, S.; Sexton, J.A.; Tao; J.; Wagner, T.; Yin, H.; Zhang, J.; Roggo, S.; Reinker, S.; Parker, C.N.
FR171456 is a specific inhibitor of mammalian NSDHL and yeast Erg26p
Nat. Commun.
6
8613
2015
Candida albicans (Q5A1B0), Homo sapiens, Homo sapiens (Q15738), Saccharomyces cerevisiae (P53199), Saccharomyces cerevisiae, Saccharomyces cerevisiae BY4743 (P53199)
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