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

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EC NUMBER
COMMENTARY hide
1.14.19.30
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RECOMMENDED NAME
GeneOntology No.
acyl-lipid (8-3)-desaturase
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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
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
arachidonate biosynthesis I (6-desaturase, lower eukaryotes)
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arachidonate biosynthesis IV (8-detaturase, lower eukaryotes)
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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.
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
malfunction
metabolism
physiological function
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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
(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
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i.e. juniperoate
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?
eicosa-11,14,17-trienoic acid + acceptor + O2 + H+
eicosa-5,11,14,17-tetraenoic acid + ?
show the reaction diagram
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-
i.e. juniperoic acid
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?
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
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?
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
?
-
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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
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
ATP
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dependent on
CoA
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dependent on
cytochrome b5
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NADH
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dependent on
additional information
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the enzyme does not contain a cytochrome b5 domain
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INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(+)-episesamin
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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
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(-)-asarinin
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non-competitive inhibitor
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(-)-epiasarinin
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non-competitive inhibitor
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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
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2-amino-N-(3-chlorophenyl)-5-fluorobenzamide
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2-amino-N-(3-chlorophenyl)benzamide
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2-amino-N-(3-fluorophenyl)benzamide
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2-amino-N-[3-(propan-2-yl)phenyl]benzamide
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4-isopentoxyaniline
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5-bromo-N-(3-chlorophenyl)-1H-indazol-3-amine
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5-chloro-N-(3-chlorophenyl)-1H-indazol-3-amine
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dibenzoazepine
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N-(3-chlorophenyl)-1H-indazol-3-amine
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N-(3-chlorophenyl)-2,3-dihydro-1H-inden-1-amine
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N-(3-chlorophenyl)-2-hydroxy-5-methoxybenzamide
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N-(3-chlorophenyl)-2-hydroxybenzamide
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N-(3-chlorophenyl)-5-(trifluoromethoxy)-1H-indazol-3-amine
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N-(3-chlorophenyl)-5-(trifluoromethyl)-1H-indazol-3-amine
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N-(3-chlorophenyl)-5-ethoxy-2-hydroxybenzamide
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N-(3-chlorophenyl)-5-fluoro-1H-indazol-3-amine
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N-(3-chlorophenyl)-5-methoxy-1H-indazol-3-amine
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N-(3-chlorophenyl)-5-methyl-1H-indazol-3-amine
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N-(3-chlorophenyl)furo[3,2-c]pyridin-4-amine
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N-(3-chlorophenyl)naphthalen-1-amine
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N-(3-chlorophenyl)quinazolin-4-amine
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N-(3-chlorophenyl)quinolin-4-amine
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N-(3-chlorophenyl)thieno[2,3-d]pyrimidin-4-amine
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N-(3-chlorophenyl)thieno[3,2-d]pyrimidin-4-amine
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N-(3-fluorophenyl)-1H-indazol-3-amine
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sesamin
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(8Z,11Z,14Z)-icosa-8,11,14-trienoyl-[glycerolipid]
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the DELTA5 desaturase activity in kidney microsomes increases linearly with the substrate concentration up to 0.02 mM
additional information
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.056
(8Z,11Z,14Z)-icosa-8,11,14-trienoyl-[glycerolipid]
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at pH 7.0 and 36°C
0.0245
dihomo-gamma-linolenic acid
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at pH 7.4 and 37°C
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Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.28
(-)-asarinin
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pH and temperature not specified in the publication
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0.71
(-)-epiasarinin
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pH and temperature not specified in the publication
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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
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pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
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MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
56000
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x * 56000, SDS-PAGE
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SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
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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
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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
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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
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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
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the expression is reduced when Pavlova salina is grown at 15°C. The ratio of expression of desaturases in samples grown at 25°C and 20°C, 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
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.19.30)
ExplorEnz
ExPASy
KEGG
MetaCyc
SABIO-RK
NCBI: PubMed, Protein, Nucleotide, Structure, Genome, OMIM
IUBMB Enzyme Nomenclature
PROSITE Database of protein families and domains
SYSTERS
Protein Mutant Database
InterPro (database of protein families, domains and functional sites)