1.14.19.20: DELTA7-sterol 5(6)-desaturase

This is an abbreviated version!
For detailed information about DELTA7-sterol 5(6)-desaturase, go to the full flat file.

Word Map on EC 1.14.19.20

1.14.19.20

ergosterol

desaturation

fluconazole

7-dehydrocholesterol

azole

desaturases

azole-resistant

smith-lemli-opitz

voriconazole

Reaction

a DELTA7-sterol

+ 2 ferrocytochrome b5 +

O2

+ 2 H+ =

a DELTA5,7-sterol

+ 2 ferricytochrome b5 + 2 H2O

Synonyms

5-DES, 5alpha-cholest-7-en-3beta-ol:oxygen DELTA5-oxidoreductase, C-5 sterol desaturase, C-5(6) sterol desaturase, Delta-7-sterol 5-desaturase, DELTA7-sterol 5-desaturase, DELTA7-sterol C56-desaturase, DELTA7-sterol DELTA5-dehydrogenase, DELTA7-sterol-C-5-desaturase, DELTA7-sterol-C5 (6)-desaturase, DELTA7-sterol-C5(6)-desaturase, DELTA7-sterol-C5-desaturase, DES5A, Des5Ap, Dhcr7, DWARF7, EC 1.14.21.6, EC 1.3.3.2, ERG 3, ERG3, erg32, Erg3p, FvC5SD, Lathosterol 5-desaturase, lathosterol oxidase, oxidase, lathosterol, Sc5d, SC5DL, SCSD, STE1, sterol C5-desaturase, sterol DELTA5,6-desaturase, sterol DELTA7-reductase, Sterol-C5-desaturase

ECTree

1 Oxidoreductases

1.14 Acting on paired donors, with incorporation or reduction of molecular oxygen

1.14.19 With oxidation of a pair of donors resulting in the reduction of O₂ to two molecules of water

1.14.19.20 DELTA7-sterol 5(6)-desaturase

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Results	in table
2	Activating Compound
110	AA Sequence
1	CAS Registry Number
18	Cloned(Commentary)
40	Cofactor
16	Disease/ Diagnostics
14	General Information
1	General Stability
12	IC50 Value
40	Inhibitors
18	KM Value [mM]
21	Localization
4	Metals/Ions
1	Molecular Weight [Da]
22	Natural Substrates/ Products (Substrates)
46	Organism
16	Pathway
2	pH Optimum
56	Protein Variants
2	Purification (Commentary)
3	Reaction
10	Reaction Type
44	Reference
24	Source Tissue
3	Specific Activity [micromol/min/mg]
1	Storage Stability
69	Substrates and Products (Substrate)
1	Subunits
68	Synonyms
1	Systematic Name
2	Temperature Optimum [°C]

Inhibitors

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

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(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

show

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

Rattus norvegicus

-

trivial name tiron, 0.5 mM, 80% inhibition

alpha-(2,4-dichlorophenyl)-alpha-phenyl-5-pyrimidine methanol

Rattus norvegicus

-

trivial name triarimol, weak inhibition

anti-cytochrome b5 antibodies

-

0.5 mg/mg protein. 36% inhibition

-

bathophenanthroline

Rattus norvegicus

-

0.5 mM, 71% inhibition

CN-

show

cyanide

show

CYC (cyctochrome c)

-

-

-

cycloheximide

Tetrahymena thermophila

-

dithiothreitol

Rattus norvegicus

-

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

posaconazole

Candida albicans

-

Salicylhydroxamic acid

-

-

salicylic hydroxamic acid

-

-

Tiron

Rattus norvegicus

-

21% residual activity at 1 mM

Triarimol

-

weak inhibition

additional information

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-

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Release 2023.1 (January 2023)