Information on EC 1.14.19.30 - acyl-lipid (8-3)-desaturase

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The expected taxonomic range for this enzyme is: Eukaryota, Bacteria

EC NUMBER
COMMENTARY hide
1.14.19.30
-
RECOMMENDED NAME
GeneOntology No.
acyl-lipid (8-3)-desaturase
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
an (8Z,11Z,14Z)-icosa-8,11,14-trienoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+ = a (5Z,8Z,11Z,14Z)-icosatetra-5,8,11,14-tetraenoyl-[glycerolipid] + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
(1)
-
-
-
an (8Z,11Z,14Z)-icosa-8,11,14-trienoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+ = a (5Z,8Z,11Z,14Z)-icosatetra-5,8,11,14-tetraenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
show the reaction diagram
an (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+ = a (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyl-[glycerolipid] + 2 ferricytochrome b5 + 2 H2O
show the reaction diagram
(2)
-
-
-
an (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+ = a (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
show the reaction diagram
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
arachidonate biosynthesis I (6-desaturase, lower eukaryotes)
-
-
arachidonate biosynthesis IV (8-detaturase, lower eukaryotes)
-
-
icosapentaenoate biosynthesis I (lower eukaryotes)
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-
icosapentaenoate biosynthesis V (8-desaturase, lower eukaryotes)
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SYSTEMATIC NAME
IUBMB Comments
DELTA8 acyl-lipid,ferrocytochrome b5:oxygen oxidoreductase (5,6 cis-dehydrogenating)
The enzyme, which has been characterized from multiple organisms including the moss Physcomitrella patens, the marine microalga Rebecca salina, and the filamentous fungus Mortierella alpina, introduces a cis double bond at the 5-position in 20-carbon polyunsaturated fatty acids incorporated in a glycerolipid that contain a Delta8 double bond. The enzyme contains a cytochrome b5 domain that acts as the direct electron donor to the active site of the desaturase, and does not require an external cytochrome.
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(7Z)-octadec-7-enoic acid + ferrocytochrome b5 + O2 + H+
(5Z,7Z)-octadeca-5,7-dienoic acid + ferricytochrome b5 + H2O
show the reaction diagram
-
5% conversion
-
-
?
(8Z,11Z,14Z)-eicosa-8,11,14-trienoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
(5Z,8Z,11Z,14Z)-eicosatetra-5,8,11,14-tetraenoyl-[glycerolipid] + ferricytochrome b5 + H2O
show the reaction diagram
-
-
-
?
(8Z,11Z,14Z)-icosa-8,11,14-trienoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
(5Z,8Z,11Z,14Z)-icosatetra-5,8,11,14-tetraenoyl-[glycerolipid] + ferricytochrome b5 + H2O
show the reaction diagram
(8Z,11Z,14Z,17Z)-eicosa-8,11,14,17-tetraenoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
(5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoyl-[glycerolipid] + ferricytochrome b5 + H2O
show the reaction diagram
best substrate
-
-
?
(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyl-[glycerolipid] + ferricytochrome b5 + H2O
show the reaction diagram
an (8Z,11Z,14Z)-icosa-8,11,14-trienoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
a (5Z,8Z,11Z,14Z)-icosatetra-5,8,11,14-tetraenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
show the reaction diagram
an (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
a (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
show the reaction diagram
-
-
-
?
an (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
a (5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14-pentaenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
show the reaction diagram
-
-
-
-
?
di-homo-gamma-linolenic acid + ferrocytochrome b5 + O2 + H+
arachidonic acid + ferricytochrome b5 + H2O
show the reaction diagram
-
55% conversion
-
-
?
dihomo-gamma-linolenic acid + ferrocytochrome b5 + O2 + H+
arachidonic acid + ferricytochrome b5 + H2O
show the reaction diagram
eicosa-11,14,17-trienoate + acceptor + O2 + H+
eicosa-5,11,14,17-tetraenoate + ?
show the reaction diagram
-
i.e. juniperoate
-
?
eicosa-11,14,17-trienoic acid + acceptor + O2 + H+
eicosa-5,11,14,17-tetraenoic acid + ?
show the reaction diagram
-
-
i.e. juniperoic acid
-
?
eicosa-11,14,17-trienoly-CoA + acceptor + O2 + H+
eicosa-5,11,14,17-tetraenoyl-CoA + ?
show the reaction diagram
-
-
i.e. juniperoyl-CoA
-
?
eicosa-11,14-dienoate + acceptor + O2 + H+
eicosa-5,11,14-trienoate + ?
show the reaction diagram
-
i.e. sciadonoate
-
?
eicosa-11,14-dienoic acid + acceptor + O2 + H+
eicosa-5,11,14-trienoic acid + ?
show the reaction diagram
-
-
i.e. sciadonoic acid
-
?
eicosa-11,14-dienoyl-CoA + acceptor + O2 + H+
eicosa-5,11,14-trienoyl-CoA + ?
show the reaction diagram
-
-
i.e. sciadonoyl-CoA
-
?
linoleic acid + ferrocytochrome b5 + O2 + H+
pinolenic acid + ferricytochrome b5 + H2O
show the reaction diagram
oleic acid + ferrocytochrome b5 + O2 + H+
taxoleic acid + ferricytochrome b5 + H2O
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
(8Z,11Z,14Z)-eicosa-8,11,14-trienoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
(5Z,8Z,11Z,14Z)-eicosatetra-5,8,11,14-tetraenoyl-[glycerolipid] + ferricytochrome b5 + H2O
show the reaction diagram
B5MFC9
-
-
-
?
(8Z,11Z,14Z)-icosa-8,11,14-trienoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
(5Z,8Z,11Z,14Z)-icosatetra-5,8,11,14-tetraenoyl-[glycerolipid] + ferricytochrome b5 + H2O
show the reaction diagram
(8Z,11Z,14Z,17Z)-eicosa-8,11,14,17-tetraenoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
(5Z,8Z,11Z,14Z,17Z)-eicosa-5,8,11,14,17-pentaenoyl-[glycerolipid] + ferricytochrome b5 + H2O
show the reaction diagram
B5MFC9
best substrate
-
-
?
(8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
(5Z,8Z,11Z,14Z,17Z)-icosa-5,8,11,14,17-pentaenoyl-[glycerolipid] + ferricytochrome b5 + H2O
show the reaction diagram
an (8Z,11Z,14Z)-icosa-8,11,14-trienoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
a (5Z,8Z,11Z,14Z)-icosatetra-5,8,11,14-tetraenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
show the reaction diagram
dihomo-gamma-linolenic acid + ferrocytochrome b5 + O2 + H+
arachidonic acid + ferricytochrome b5 + H2O
show the reaction diagram
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ATP
-
dependent on
CoA
-
dependent on
cytochrome b5
-
NADH
-
dependent on
additional information
-
the enzyme does not contain a cytochrome b5 domain
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-episesamin
-
specific inhibitor
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(+)-sesamin
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specific inhibitor
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(+)-sesaminol
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specific inhibitor
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(+)-sesamolin
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specific inhibitor
-
(-)-asarinin
-
non-competitive inhibitor
-
(-)-epiasarinin
-
non-competitive inhibitor
-
2-(2,2,3,3,3-pentafluoropropoxy)-3-[4-(2,2,2-trifluoroethoxy)phenyl]-5,7-dihydro-3H-pyrrolo[2,3-d]pyrimidine-4,6-dione
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-
2-amino-5-chloro-N-(3-chlorophenyl)benzamide
-
-
2-amino-N-(3-chlorophenyl)-5-fluorobenzamide
-
-
2-amino-N-(3-chlorophenyl)benzamide
-
-
2-amino-N-(3-fluorophenyl)benzamide
-
-
2-amino-N-[3-(propan-2-yl)phenyl]benzamide
-
-
4-isopentoxyaniline
-
-
-
5-bromo-N-(3-chlorophenyl)-1H-indazol-3-amine
-
-
5-chloro-N-(3-chlorophenyl)-1H-indazol-3-amine
-
-
dibenzoazepine
-
-
-
N-(3-chlorophenyl)-1H-indazol-3-amine
-
-
N-(3-chlorophenyl)-2,3-dihydro-1H-inden-1-amine
-
-
N-(3-chlorophenyl)-2-hydroxy-5-methoxybenzamide
-
-
N-(3-chlorophenyl)-2-hydroxybenzamide
-
-
N-(3-chlorophenyl)-5-(trifluoromethoxy)-1H-indazol-3-amine
-
-
N-(3-chlorophenyl)-5-(trifluoromethyl)-1H-indazol-3-amine
-
-
N-(3-chlorophenyl)-5-ethoxy-2-hydroxybenzamide
-
-
N-(3-chlorophenyl)-5-fluoro-1H-indazol-3-amine
-
-
N-(3-chlorophenyl)-5-methoxy-1H-indazol-3-amine
-
-
N-(3-chlorophenyl)-5-methyl-1H-indazol-3-amine
-
-
N-(3-chlorophenyl)furo[3,2-c]pyridin-4-amine
-
-
N-(3-chlorophenyl)naphthalen-1-amine
-
-
N-(3-chlorophenyl)quinazolin-4-amine
-
-
N-(3-chlorophenyl)quinolin-4-amine
-
-
N-(3-chlorophenyl)thieno[2,3-d]pyrimidin-4-amine
-
-
N-(3-chlorophenyl)thieno[3,2-d]pyrimidin-4-amine
-
-
N-(3-fluorophenyl)-1H-indazol-3-amine
-
-
sesamin
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(8Z,11Z,14Z)-icosa-8,11,14-trienoyl-[glycerolipid]
-
the DELTA5 desaturase activity in kidney microsomes increases linearly with the substrate concentration up to 0.02 mM
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.056
(8Z,11Z,14Z)-icosa-8,11,14-trienoyl-[glycerolipid]
-
at pH 7.0 and 36C
0.0245
dihomo-gamma-linolenic acid
-
at pH 7.4 and 37C
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.28
(-)-asarinin
-
pH and temperature not specified in the publication
-
0.71
(-)-epiasarinin
-
pH and temperature not specified in the publication
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.000034
2-amino-5-chloro-N-(3-chlorophenyl)benzamide
Mus musculus
-
pH and temperature not specified in the publication
0.000067
2-amino-N-(3-chlorophenyl)-5-fluorobenzamide
Mus musculus
-
pH and temperature not specified in the publication
0.000058
2-amino-N-(3-chlorophenyl)benzamide
Mus musculus
-
pH and temperature not specified in the publication
0.000516
2-amino-N-(3-fluorophenyl)benzamide
Mus musculus
-
pH and temperature not specified in the publication
0.000843
2-amino-N-[3-(propan-2-yl)phenyl]benzamide
Mus musculus
-
pH and temperature not specified in the publication
0.000021
5-bromo-N-(3-chlorophenyl)-1H-indazol-3-amine
Mus musculus
-
pH and temperature not specified in the publication
0.000005
5-chloro-N-(3-chlorophenyl)-1H-indazol-3-amine
Mus musculus
-
pH and temperature not specified in the publication
0.000084
N-(3-chlorophenyl)-1H-indazol-3-amine
Mus musculus
-
pH and temperature not specified in the publication
0.000173
N-(3-chlorophenyl)-2,3-dihydro-1H-inden-1-amine
Mus musculus
-
pH and temperature not specified in the publication
0.000015
N-(3-chlorophenyl)-2-hydroxy-5-methoxybenzamide
Mus musculus
-
pH and temperature not specified in the publication
0.000174
N-(3-chlorophenyl)-2-hydroxybenzamide
Mus musculus
-
pH and temperature not specified in the publication
0.003
N-(3-chlorophenyl)-5-(trifluoromethoxy)-1H-indazol-3-amine
Mus musculus
-
IC50 above 0.003 mM, pH and temperature not specified in the publication
0.000254
N-(3-chlorophenyl)-5-(trifluoromethyl)-1H-indazol-3-amine
Mus musculus
-
pH and temperature not specified in the publication
0.000925
N-(3-chlorophenyl)-5-ethoxy-2-hydroxybenzamide
Mus musculus
-
pH and temperature not specified in the publication
0.000058
N-(3-chlorophenyl)-5-fluoro-1H-indazol-3-amine
Mus musculus
-
pH and temperature not specified in the publication
0.000008
N-(3-chlorophenyl)-5-methoxy-1H-indazol-3-amine
Mus musculus
-
pH and temperature not specified in the publication
0.000006
N-(3-chlorophenyl)-5-methyl-1H-indazol-3-amine
Mus musculus
-
pH and temperature not specified in the publication
0.000371
N-(3-chlorophenyl)furo[3,2-c]pyridin-4-amine
Mus musculus
-
pH and temperature not specified in the publication
0.000017
N-(3-chlorophenyl)naphthalen-1-amine
Mus musculus
-
pH and temperature not specified in the publication
0.000011
N-(3-chlorophenyl)quinazolin-4-amine
Mus musculus
-
pH and temperature not specified in the publication
0.000018
N-(3-chlorophenyl)quinolin-4-amine
Mus musculus
-
pH and temperature not specified in the publication
0.00026
N-(3-chlorophenyl)thieno[2,3-d]pyrimidin-4-amine
Mus musculus
-
pH and temperature not specified in the publication
0.00005
N-(3-chlorophenyl)thieno[3,2-d]pyrimidin-4-amine
Mus musculus
-
pH and temperature not specified in the publication
0.000059
N-(3-fluorophenyl)-1H-indazol-3-amine
Mus musculus
-
pH and temperature not specified in the publication
0.000058
sesamin
Mus musculus
-
pH and temperature not specified in the publication
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
56000
-
x * 56000, SDS-PAGE
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Arabidopsis thaliana
-
expressed in CHO cells
expressed in Saccharomyces cerevisiae strain BY4741
expressed in Saccharomyces cerevisiae strain InvSc1
expressed in Saccharomyces cerevisiae strain SC334 and in transgenic canola seeds
-
expressed in Saccharoymces cerevisiae strain CEN.PK 113-5D
expression in the yeast Saccharomyces cerevisiae. The yeast cells acquire functional DELTA5-desaturase activity and are capable of synthesizing arachidonic acid from the substrate di-homo-gamma-linolenic acid
-
expression in yeast and in Arabidopsis thaliana
expression of the enzyme in Saccharomyces cerevisiae results in the production of the DELTA5-containing fatty acid arachidonic acid in cells that are provided di-homo-gamma-linolenic acid
-
overexpressed in Phaeodactylum tricornutum
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
higher growth temperature increases the expression of front-end desaturase genes
the estimated enzyme activity is lower in subjects with type 2 diabetes compared with those with normal glucose tolerance
-
the expression is reduced when Pavlova salina is grown at 15C. The ratio of expression of desaturases in samples grown at 25C and 20C, is 5times greater for the DELTA4-desaturase than for the DELTA5-desaturase gene
when rats are fed a diet containing 10% (v/v) safflower oil or menhaden fish oil, the level of hepatic mRNA is 25% of that found in the liver of rats fed a fat-free diet or a diet containing triolein
-