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Information on EC 1.14.19.41 - sterol 22-desaturase
for references in articles please use BRENDA:EC1.14.19.41
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EC Tree 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
1.14.19.41 sterol 22-desaturase
IUBMB Comments
A heme-thiolate protein (P-450). The enzyme, found in yeast and plants, catalyses the introduction of a double bond between the C-22 and C-23 carbons of certain sterols. In yeast the enzyme acts on ergosta-5,7,24(28)-trien-3β-ol, a step in the biosynthesis of ergosterol. The enzyme from the plant Arabidopsis thaliana acts on sitosterol and 24-epi-campesterol, producing stigmasterol and brassicasterol, respectively.
The enzyme appears in viruses and cellular organisms
- 1.14.19.41
- ergosterol
- stigmasterol
- azole
-
desaturases
- ketoconazole
- phytosterols
- campesterol
- beta-sitosterol
-
withanolides
-
withania
- somnifera
-
xanthophyllomyces
- dendrorhous
- brassicasterol
-
14alpha-demethylase
- sitosterol
Reaction Schemes
showSynonyms
cyp61, sterol c-22 desaturase, cyp710a, cyp710a1, cyp710a11, cyp710a2, c-22 sterol desaturase, erg5p, sterol c22-desaturase, cyp710a14, more
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SYNONYM 
ORGANISM
UNIPROT
COMMENTARY 
LITERATURE
CTP61
CYP710A
CYP710A11
cytochrome P-450 sterol DELTA22-desaturase
cytochrome P-45061
DELTA22-desaturase
ERG5
Erg5p
P450 61
sterol C-22 desaturase
sterol DELTA22-desaturase
CYP710A
-
-
-
-
ERG5
-
-
-
-
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
ergosta-5,7,24(28)-trien-3beta-ol + NADPH + H+ + O2 = ergosta-5,7,22,24(28)-tetraen-3beta-ol + NADP+ + 2 H2O
-
-
-
-
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PATHWAY SOURCE
PATHWAYS
MetaCyc
ergosterol biosynthesis I, phytosterol biosynthesis (plants)
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SYSTEMATIC NAME
IUBMB Comments
ergosta-5,7,24(28)-trien-3beta-ol,NADPH:oxygen oxidoreductase (22,23-dehydrogenating)
A heme-thiolate protein (P-450). The enzyme, found in yeast and plants, catalyses the introduction of a double bond between the C-22 and C-23 carbons of certain sterols. In yeast the enzyme acts on ergosta-5,7,24(28)-trien-3beta-ol, a step in the biosynthesis of ergosterol. The enzyme from the plant Arabidopsis thaliana acts on sitosterol and 24-epi-campesterol, producing stigmasterol and brassicasterol, respectively.
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
22,23-dihydrobrassicasterol + NADPH + H+ + O2
brassicasterol + NADP+ + H2O
-
Substrates: highest activity
Products: -
Products: -
?
24-epi-campesterol + NADPH + H+ + O2
brassicasterol + crinosterol + NADP+ + H2O
Substrates: substrate for isoform CYP710A2 but not CYP710A1
Products: brassicasterol is the major product
Products: brassicasterol is the major product
?
24-epi-campesterol + NADPH + H+ + O2
brassicasterol + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
24-methylcholesterol + NADPH + H+ + O2
brassicasterol + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
beta-sitosterol + NADPH + H+ + O2
stigmasta-5,22-dien-3beta-ol + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
clionasterol + NADPH + H+ + O2
poriferasterol + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
ergosta-5,7,24(28)-trien-3beta-ol + NADPH + H+ + O2
ergosta-5,7,22,24(28)-tetraen-3-beta-ol + NADP+ + 2 H2O
-
Substrates: -
Products: -
Products: -
?
ergosta-5,7,24(28)-trien-3beta-ol + NADPH + H+ + O2
ergosta-5,7,22,24(28)-tetraen-3-beta-ol + NADP+ + H2O
sitosterol + NADPH + H+ + O2
stigmasterol + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
beta-sitosterol + NADPH + H+ + O2
stigmasterol + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
beta-sitosterol + NADPH + H+ + O2
stigmasterol + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
beta-sitosterol + NADPH + H+ + O2
stigmasterol + NADP+ + H2O
Substrates: high affinity substrate
Products: -
Products: -
?
beta-sitosterol + NADPH + H+ + O2
stigmasterol + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
beta-sitosterol + NADPH + H+ + O2
stigmasterol + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
ergosta-5,7,24(28)-trien-3beta-ol + NADPH + H+ + O2
ergosta-5,7,22,24(28)-tetraen-3-beta-ol + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
ergosta-5,7,24(28)-trien-3beta-ol + NADPH + H+ + O2
ergosta-5,7,22,24(28)-tetraen-3-beta-ol + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
ergosta-5,7-dien-3beta-ol + NADPH + H+ + O2
ergosterol + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
ergosta-5,7-dien-3beta-ol + NADPH + H+ + O2
ergosterol + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
ergosta-5,7-dien-3beta-ol + NADPH + H+ + O2
ergosterol + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
ergosta-5,7-dien-3beta-ol + NADPH + H+ + O2
ergosterol + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
ergosta-5,7-dien-3beta-ol + NADPH + H+ + O2
ergosterol + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
ergosta-5,7-dienol + NADPH + H+ + O2
ergosterol + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
ergosta-5,7-dienol + NADPH + H+ + O2
ergosterol + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
ergosta-5,7-dienol + NADPH + H+ + O2
ergosterol + NADP+ + H2O
[Candida] glabrata L5DU61
-
Substrates: -
Products: -
Products: -
?
additional information
?
-
Substrates: 24-epi-campesterol is no substrate for isoform CYP710A1
Products: brassicasterol is the major product
Products: brassicasterol is the major product
?
additional information
?
-
Substrates: 24-epi-campesterol is no substrate for isoform CYP710A1
Products: brassicasterol is the major product
Products: brassicasterol is the major product
?
additional information
?
-
-
Substrates: no activity with campesterol
Products: -
Products: -
?
additional information
?
-
-
Substrates: campesterol and 24-epi-campesterol are not accepted as substrates
Products: -
Products: -
?
additional information
?
-
Substrates: no activity with campesterol
Products: -
Products: -
?
additional information
?
-
-
Substrates: no activity with campesterol
Products: -
Products: -
?
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NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
LITERATURE
COMMENTARY
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
24-methylcholesterol + NADPH + H+ + O2
brassicasterol + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
ergosta-5,7,24(28)-trien-3beta-ol + NADPH + H+ + O2
ergosta-5,7,22,24(28)-tetraen-3-beta-ol + NADP+ + H2O
beta-sitosterol + NADPH + H+ + O2
stigmasterol + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
beta-sitosterol + NADPH + H+ + O2
stigmasterol + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
ergosta-5,7,24(28)-trien-3beta-ol + NADPH + H+ + O2
ergosta-5,7,22,24(28)-tetraen-3-beta-ol + NADP+ + H2O
Substrates: -
Products: -
Products: -
?
ergosta-5,7,24(28)-trien-3beta-ol + NADPH + H+ + O2
ergosta-5,7,22,24(28)-tetraen-3-beta-ol + NADP+ + H2O
-
Substrates: -
Products: -
Products: -
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
(20S)-21-isocyano-20-methylpregn-5-en-3beta-ol
-
complete inhibition at 0.15 mM
additional information
-
not inhibited by desmosterol, 24-methylenecholesterol, and 24-bromocholesterol
-
(3S,20S)-20-N-butylcarbamoylpregn-7-en-3beta-ol
-
selective inhibitors of fungal sterol C22-desaturase. The inhibitor is subjected to antifungal susceptibility testing on patient isolates according to modified EUCAST guidelines. But, the organism shows no significant reduction of cell growth and/or viability up to an inhibitor concentration of 0.1 mg/ml. Thus the sterol C22-desaturase is not an attractive target for the development of antifungals
(3S,20S)-20-N-butylcarbamoylpregn-7-en-3beta-ol
-
selective inhibitors of fungal sterol C22-desaturase. The inhibitor is subjected to antifungal susceptibility testing on patient isolates according to modified EUCAST guidelines. But, the organism shows no significant reduction of cell growth and/or viability up to an inhibitor concentration of 0.1 mg/ml. Thus the sterol C22-desaturase is not an attractive target for the development of antifungals
(3S,20S)-20-N-butylcarbamoylpregn-7-en-3beta-ol
selective inhibitors of fungal sterol C22-desaturase. The inhibitor is subjected to antifungal susceptibility testing on patient isolates according to modified EUCAST guidelines. But, the organism shows no significant reduction of cell growth and/or viability up to an inhibitor concentration of 0.1 mg/ml. Thus the sterol C22-desaturase is not an attractive target for the development of antifungals
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.001
beta-sitosterol
isoform CYP710A1, pH and temperature not specified in the publication
0.0037
beta-sitosterol
isoform CYP710A2, pH and temperature not specified in the publication
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TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.009
beta-sitosterol
isoform CYP710A1, pH and temperature not specified in the publication
0.17
beta-sitosterol
isoform CYP710A2, pH and temperature not specified in the publication
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kcat/KM VALUE [1/mMs-1]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
0.015
(20S)-21-isocyano-20-methylpregn-5-en-3beta-ol
Saccharomyces cerevisiae
-
at 27Ā°C, pH not specified in the publication
0.0000001
itraconazole
[Candida] glabrata
-
calculated value, pH and temperature not specified in the publication
0.0000001
fluconazole
[Candida] glabrata
-
calculated value, pH and temperature not specified in the publication
0.0000001
ketoconazole
[Candida] glabrata
-
calculated value, pH and temperature not specified in the publication
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
subspecies Physcomitrella patens patens, strain Gransden Wood
-
-
brenda
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
Highest Expressing Human Cell Lines
Cell Line LinksPlease wait a moment until the data is sorted. This message will disappear when the data is sorted.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
drug target
malfunction
-
enzyme gene erg5 deletion increases azole susceptibility but does not cause accumulation of 14alpha-methylated sterols during ketoconazole stress in Neurospora crassa
metabolism
drug target
sterol C22-desaturase is not an attractive target for the development of antifungals
drug target
[Candida] glabrata NCCLS 84
-
sterol C22-desaturase is not an attractive target for the development of antifungals
-
metabolism
-
the enzyme is required in ergosterol biosynthesis and not essential for cell viability
metabolism
-
the enzyme is involved in plant sterol biosynthesis. It is one of the enzymes that is responsible for maintaining the optimal balance between sterols
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UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable).
The reliability class of the localization prediction ranges from 1 (very reliable) to 5 (not reliable). C7101_ARATH
495
1
55724
Swiss-Prot
Secretory Pathway (Reliability: 1)
C7102_ARATH
499
1
56346
Swiss-Prot
Secretory Pathway (Reliability: 1)
C7103_ARATH
493
1
55874
Swiss-Prot
Secretory Pathway (Reliability: 1)
C7104_ARATH
493
2
55690
Swiss-Prot
Secretory Pathway (Reliability: 1)
C7111_SOLLC
501
1
57519
Swiss-Prot
Secretory Pathway (Reliability: 2)
ERG5A_GIBZE
Gibberella zeae (strain ATCC MYA-4620 / CBS 123657 / FGSC 9075 / NRRL 31084 / PH-1)
536
0
60505
Swiss-Prot
other Location (Reliability: 3)
ERG5B_GIBZE
Gibberella zeae (strain ATCC MYA-4620 / CBS 123657 / FGSC 9075 / NRRL 31084 / PH-1)
534
0
59915
Swiss-Prot
other Location (Reliability: 4)
ERG5_ASPFU
Neosartorya fumigata (strain ATCC MYA-4609 / Af293 / CBS 101355 / FGSC A1100)
521
1
59042
Swiss-Prot
other Location (Reliability: 3)
ERG5_CANAL
Candida albicans (strain SC5314 / ATCC MYA-2876)
517
1
59652
Swiss-Prot
other Location (Reliability: 4)
ERG5_SCHPO
Schizosaccharomyces pombe (strain 972 / ATCC 24843)
543
0
62271
Swiss-Prot
other Location (Reliability: 2)
ERG5_YEAST
Saccharomyces cerevisiae (strain ATCC 204508 / S288c)
538
0
61334
Swiss-Prot
other Location (Reliability: 3)
A0A8B6D2N0_MYTGA
384
0
44186
TrEMBL
other Location (Reliability: 3)
A0A8J5EL13_9ASCO
507
1
57473
TrEMBL
other Location (Reliability: 5)
A0A8J5BTV2_9ASCO
507
1
57366
TrEMBL
other Location (Reliability: 5)
A0A8J8WA31_9EURO
528
0
59404
TrEMBL
Secretory Pathway (Reliability: 5)
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
55000
57028
-
x * 57028, isoform CYP710A14, calculated from amino acid sequence
57410
-
x * 57410, isoform CYP710A13, calculated from amino acid sequence
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SUBUNIT
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
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PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
additional information
-
mutant CA108 is an erg11 erg5 double mutant harboring a single amino acid substitution (A114S) in sterol 14DELTA-demethylase (Erg11p) and sequence repetition (10 duplicated amino acids), which nullify C22 desaturase (Erg5p) function
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PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
amino-octyl Sepharose column chromatography and hydroxyapatite column chromatography
-
aminooctyl-agarose column chromatography and hydroxylapatite column chromatography
-
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CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in a baculovirus/Sf9 insect cell system
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
the enzyme transcript increases 4fold in pericarp of ripening wild type fruit
-
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REF.
AUTHORS
TITLE
JOURNAL
VOL.
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