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Information on EC 1.14.19.20 - DELTA7-sterol 5(6)-desaturase and Organism(s) Homo sapiens

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IUBMB Comments
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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Homo sapiens
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The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Bacteria, Eukaryota
Synonyms
erg3p, c-5 sterol desaturase, 5-des, fvc5sd, erg 3, lathosterol 5-desaturase, sterol c5-desaturase, des5a, sterol-c5-desaturase, sc5dl, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
5-DES
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5alpha-cholest-7-en-3beta-ol:oxygen DELTA5-oxidoreductase
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C-5 sterol desaturase
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Delta-7-sterol 5-desaturase
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DELTA7-sterol 5-desaturase
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DELTA7-sterol DELTA5-dehydrogenase
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DELTA7-sterol-C5(6)-desaturase
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Dhcr7
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Lathosterol 5-desaturase
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lathosterol oxidase
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oxidase, lathosterol
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SC5DL
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sterol C5-desaturase
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sterol DELTA7-reductase
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Sterol-C5-desaturase
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
oxidation
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redox reaction
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reduction
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PATHWAY SOURCE
PATHWAYS
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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.
CAS REGISTRY NUMBER
COMMENTARY hide
37255-37-1
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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
ergosta-7,22-dien-3beta-ol + ferrocytochrome b5 + O2 + H+
ergosta-5,7,22-trien-3beta-ol + ferricytochrome b5 + 2 H2O
show the reaction diagram
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-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
cytochrome b5
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NAD(P)H
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-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Iron
required
additional information
-
the enzyme may hold non-heme irons in the catalytic center containing histidine residues
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(3S,20S)-20-N-(2-methylpropyl)carbamoylpregn-7-en-3beta-ol
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specific
(3S,20S)-20-N-(2-methylpropyl)carbamoylpregn-7-en-3beta-yl acetate
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specific for the enzyme. Prodrug, transformed into the 3beta-hydroxy derivative under in vitro conditions
(3S,20S)-20-N-butylcarbamoylpregn-7-en-3beta-ol
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specific
(3S,20S)-20-N-butylcarbamoylpregn-7-en-3beta-yl acetate
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specific for the enzyme. Prodrug, transformed into the 3beta-hydroxy derivative under in vitro conditions
(3S,20S)-20-N-ethylcarbamoylpregn-7-en-3beta-ol
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(3S,20S)-20-N-ethylcarbamoylpregn-7-en-3beta-yl acetate
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(3S,20S)-20-N-pentylcarbamoylpregn-7-en-3beta-ol
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specific
(3S,20S)-20-N-pentylcarbamoylpregn-7-en-3beta-yl acetate
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specific for the enzyme. Prodrug, transformed into the 3beta-hydroxy derivative under in vitro conditions
(3S,20S)-20-N-propylcarbamoylpregn-7-en-3beta-ol
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(3S,20S)-20-N-propylcarbamoylpregn-7-en-3beta-yl acetate
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(3S,20S)-20-N-tert-butylcarbamoylpregn-7-en-3beta-ol
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specific
(3S,20S)-20-N-tert-butylcarbamoylpregn-7-en-3beta-yl acetate
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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
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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
lathosterol side chain amides
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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
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Triarimol
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weak inhibition
additional information
-
cytotoxicity and inhibitor potencies for inhibition of total cholesterol biosynthesis, overview
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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
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inhibition of total cholesterol production
0.00045
(3S,20S)-20-N-(2-methylpropyl)carbamoylpregn-7-en-3beta-yl acetate
Homo sapiens
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inhibition of total cholesterol production
0.0007
(3S,20S)-20-N-butylcarbamoylpregn-7-en-3beta-ol
Homo sapiens
-
inhibition of total cholesterol production
0.00091
(3S,20S)-20-N-butylcarbamoylpregn-7-en-3beta-yl acetate
Homo sapiens
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inhibition of total cholesterol production
0.00116
(3S,20S)-20-N-pentylcarbamoylpregn-7-en-3beta-ol
Homo sapiens
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inhibition of total cholesterol production
0.0011
(3S,20S)-20-N-pentylcarbamoylpregn-7-en-3beta-yl acetate
Homo sapiens
-
inhibition of total cholesterol production
0.00105
(3S,20S)-20-N-tert-butylcarbamoylpregn-7-en-3beta-ol
Homo sapiens
-
inhibition of total cholesterol production
0.00095
(3S,20S)-20-N-tert-butylcarbamoylpregn-7-en-3beta-yl acetate
Homo sapiens
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inhibition of total cholesterol production
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
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mRNA expression
Manually annotated by BRENDA team
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primary hepatocytes are used for analysis
Manually annotated by BRENDA team
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mRNA expression
Manually annotated by BRENDA team
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mRNA expression
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
-
mRNA expression
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
SC5D_HUMAN
299
3
35301
Swiss-Prot
other Location (Reliability: 5)
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30000
x * 30000, SDS-PAGE
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
?
x * 30000, SDS-PAGE
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
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enzyme deficiency leads to lathosterolosis, a defect of cholesterol biosynthesis, phenotype, detailed overview
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in a Saccharomyces cerevisiae erg3-deficient mutant strain
expression in Saccharomyces cerevisiae erg3 mutant
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
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
Manually annotated by BRENDA team
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
Manually annotated by BRENDA team
Giera, M.; Renard, D.; Ploessl, F.; Bracher, F.
Lathosterol side chain amidesa new class of human lathosterol oxidase inhibitors
Steroids
73
299-308
2008
Homo sapiens
Manually annotated by BRENDA team
Rossi, M.; DArmiento, M.; Parisi, I.; Ferrari, P.; Hall, C.M.; Cervasio, M.; Rivasi, F.; Balli, F.; Vecchione, R.; Corso, G.; Andria, G.; Parenti, G.
Clinical phenotype of lathosterolosis
Am. J. Med. Genet. A
143A
2371-2381
2007
Homo sapiens
Manually annotated by BRENDA team
Acimovic, J.; Korosec, T.; Seliskar, M.; Bjorkhem, I.; Monostory, K.; Szabo, P.; Pascussi, J.M.; Belic, A.; Urleb, U.; Kocjan, D.; Rozman, D.
Inhibition of human sterol DELTA7-reductase and other postlanosterol enzymes by LK-980, a novel inhibitor of cholesterol synthesis
Drug Metab. Dispos.
39
39-46
2011
Homo sapiens
Manually annotated by BRENDA team
Nishino, H.; Nishi, S.; Ishibashi, T.
Nine of ten histidine residues, located in three conserved clusters, are required for mammalian sterol C5-desaturase activity
Biomed. Res.
24
99-106
2003
Homo sapiens (O75845)
-
Manually annotated by BRENDA team