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Enzyme Nomenclature
Information on EC 1.14.19.25 - acyl-lipid omega-3 desaturase (cytochrome b5)
Word Map on EC 1.14.19.25
- 1.14.19.25
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linolenic
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polyunsaturated
-
desaturation
- plastid
-
alpha-linolenic
- flax
-
trienoic
- plastidial
-
pufas
-
linum
-
oilseed
- usitatissimum
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The enzyme appears in viruses and cellular organisms
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EC NUMBER 
COMMENTARY 
1.14.19.25
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RECOMMENDED NAME
GeneOntology No.
acyl-lipid omega-3 desaturase (cytochrome b5)
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REACTION
REACTION DIAGRAM
COMMENTARY
ORGANISM
UNIPROT
LITERATURE
a linoleoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+ = an alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
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-
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PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
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SYSTEMATIC NAME
IUBMB Comments
(9Z,12Z)-octadeca-9,12-dienoyl-[glycerolipid],ferrocytochrome b5:oxygen oxidoreductase (15,16 cis-dehydrogenating)
This microsomal enzyme introduces a cis double bond three carbons away from the methyl end of a fatty acid incorporated into a glycerolipid. The distance from the carboxylic acid end of the molecule does not have an effect. The plant enzyme acts on carbon 15 of linoleoyl groups incorporated into both the sn-1 and sn-2 positions of the glycerol backbone of phosphatidylcholine and other phospholipids, converting them into alpha-linolenoyl groups. The enzyme from the fungus Mortierella alpina acts on gamma-linolenoyl and arachidonoyl groups, converting them into stearidonoyl and icosapentaenoyl groups, respectively [3]. cf. EC 1.14.19.35, acyl-lipid omega-3 desaturase (ferredoxin).
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ORGANISM
COMMENTARY
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
malfunction
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accumulation of linoleoyl (18:2) groups at the expense of linolenoyl groups (18:3) is the only substantial difference in membrane lipid biosynthesis in leaves and roots of fad3-2 plants relative to wild type
metabolism
additional information
metabolism
regulation of the enzyme through synergistic and antagonistic hormonal interactions, overview
metabolism
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regulation of the enzyme through synergistic and antagonistic hormonal interactions, overview
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additional information
fatty acid profile of wild-type and fad3 mutant roots in response to several plant hormones, overview
additional information
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fatty acid profile of wild-type and fad3 mutant roots in response to several plant hormones, overview
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SUBSTRATE
PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
a dihomo-gamma-linolenoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
a (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
a gamma-linolenoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
a stearidonoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
a linoleoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
an alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
an arachidonoyl-[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
arachidonic acid + ferrocytochrome b5 + O2 + H+
eicosapentaenoic acid + ferricytochrome b5 + H2O
-
-
-
-
?
linoleoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + H2O
omega-6 linoleic acid + ferrocytochrome b5 + O2 + H+
linolenic acid + ferricytochrome b5 + H2O
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best substrate
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-
?
a dihomo-gamma-linolenoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
a (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
(8Z,11Z,14Z)-icosa-8,11,14-trienoyl-[glycerolipid] i.e. dihomo-linolenoyl-[glycerolipid]. Yeast transformant is grown in complete medium containing 0.1% of exogenous fatty acids and then the total fatty acid composition is analyzed by GLC. The enzyme accepts electrons from the microsomal cytochrome b5 or cytochrome b5 motif of another desaturases
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-
?
a dihomo-gamma-linolenoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
a (8Z,11Z,14Z,17Z)-icosa-8,11,14,17-tetraenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
(8Z,11Z,14Z)-icosa-8,11,14-trienoyl-[glycerolipid] i.e. dihomo-linolenoyl-[glycerolipid]. Yeast transformant is grown in complete medium containing 0.1% of exogenous fatty acids and then the total fatty acid composition is analyzed by GLC. The enzyme accepts electrons from the microsomal cytochrome b5 or cytochrome b5 motif of another desaturases
-
-
?
a gamma-linolenoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
a stearidonoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
(6Z,9Z,12Z)-octadeca-6,9,12-trienoyl-[glycerolipid] i.e. gamma-linolenoyl-[glycerolipid]. Yeast transformant is grown in complete medium containing 0.1% of exogenous fatty acids and then the total fatty acid composition is analyzed by GLC. The enzyme accepts electrons from the microsomal cytochrome b5 or cytochrome b5 motif of another desaturases
(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyl-[glycerolipid] i.e.stearidonoyl-[glycerolipid]
-
?
a gamma-linolenoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
a stearidonoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
(6Z,9Z,12Z)-octadeca-6,9,12-trienoyl-[glycerolipid] i.e. gamma-linolenoyl-[glycerolipid]. Yeast transformant is grown in complete medium containing 0.1% of exogenous fatty acids and then the total fatty acid composition is analyzed by GLC. The enzyme accepts electrons from the microsomal cytochrome b5 or cytochrome b5 motif of another desaturases
(6Z,9Z,12Z,15Z)-octadeca-6,9,12,15-tetraenoyl-[glycerolipid] i.e.stearidonoyl-[glycerolipid]
-
?
a linoleoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
an alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
-
-
-
-
?
a linoleoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
an alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
(9Z,12Z)-octadeca-9,12-dienoyl-[glycerolipid] i.e. linoleoyl-[glycerolipid]. Yeast transformant is grown in complete medium containing 0.1% of exogenous fatty acids and then the total fatty acid composition is analyzed by GLC. The enzyme accepts electrons from the microsomal cytochrome b5 or cytochrome b5 motif of another desaturases
(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl-[glycerolipid] i.e. linolenoyl-[glycerolipid]
-
?
a linoleoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
an alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
(9Z,12Z)-octadeca-9,12-dienoyl-[glycerolipid] i.e. linoleoyl-[glycerolipid]. Yeast transformant is grown in complete medium containing 0.1% of exogenous fatty acids and then the total fatty acid composition is analyzed by GLC. The enzyme accepts electrons from the microsomal cytochrome b5 or cytochrome b5 motif of another desaturases
(9Z,12Z,15Z)-octadeca-9,12,15-trienoyl-[glycerolipid] i.e. linolenoyl-[glycerolipid]
-
?
an arachidonoyl-[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
(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl-[glycerolipid] i.e. arachidonoyl-[glycerolipid]. Yeast transformant is grown in complete medium containing 0.1% of exogenous fatty acids and then the total fatty acid composition is analyzed by GLC. The enzyme accepts electrons from the microsomal cytochrome b5 or cytochrome b5 motif of another desaturases
-
-
?
an arachidonoyl-[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
(5Z,8Z,11Z,14Z)-icosa-5,8,11,14-tetraenoyl-[glycerolipid] i.e. arachidonoyl-[glycerolipid]. Yeast transformant is grown in complete medium containing 0.1% of exogenous fatty acids and then the total fatty acid composition is analyzed by GLC. The enzyme accepts electrons from the microsomal cytochrome b5 or cytochrome b5 motif of another desaturases
-
-
?
linoleoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + H2O
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-
-
-
?
linoleoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + H2O
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-
-
-
?
linoleoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + H2O
-
-
-
?
linoleoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + H2O
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-
-
-
?
additional information
?
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the enzyme shows no DELTA12-desaturase, DELTA6-desaturase or DELTA5-desaturase activity
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-
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additional information
?
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the enzyme shows no DELTA12-desaturase, DELTA6-desaturase or DELTA5-desaturase activity
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-
-
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NATURAL SUBSTRATES
NATURAL PRODUCTS
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate)
(Substrate)
LITERATURE
(Substrate)
(Substrate)
COMMENTARY
(Product)
(Product)
LITERATURE
(Product)
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
r=reversible
ir=irreversible
?=not specified
a linoleoyl-[glycerolipid] + 2 ferrocytochrome b5 + O2 + 2 H+
an alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + 2 H2O
-
-
-
-
?
linoleoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + H2O
linoleoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + H2O
-
-
-
-
?
linoleoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + H2O
-
-
-
-
?
linoleoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + H2O
Q84X83, Q84X84, Q9FXK9
-
-
-
?
linoleoyl-[glycerolipid] + ferrocytochrome b5 + O2 + H+
alpha-linolenoyl-[glycerolipid] + ferricytochrome b5 + H2O
-
-
-
-
?
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COFACTOR
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
IMAGE
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SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
SOURCE
additional information
additional information
tissue expression analysis of gene fad3, overview
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LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY
GeneOntology No.
LITERATURE
SOURCE
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Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
expressed in Saccharomyces cerevisiae strain K601; expressed in Saccharomyces cerevisiae strain K601; expressed in Saccharomyces cerevisiae strain K601
gene fad3, recombinant expression of a fad3-LUC fusion construct in Arabidopsis thaliana plants through trabsfection with Agrobacterium tumefaciens strain C58 pGV3850
isolation of a gene and functionally complementation of a mutant of Arabidopsis deficient in omega-3 unsaturated fatty acids
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EXPRESSION
ORGANISM
UNIPROT
LITERATURE
auxin and cytokinin induce the enzyme expression ectopically in roots when applied during vegetative growth but not during repoductive growth or germination, the induction is repressed by abscisic acid
auxin and cytokinin induce the enzyme expression ectopically in roots when applied during vegetative growth but not during repoductive growth or germination, the induction is repressed by abscisic acid
auxin and cytokinin induce the enzyme expression ectopically in roots when applied during vegetative growth but not during repoductive growth or germination, the induction is repressed by abscisic acid
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-
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ENGINEERING
ORGANISM
UNIPROT
COMMENTARY
LITERATURE
food industry
-
combinations of mutations in the three FAD3 enzyme genes are capable of producing soybean seeds containing only 1% linolenic acid in the seed oil
additional information
-
a mutant protein lacking 110 amino acids at its C terminus exhibits a drastic decline in its DELTA-15 desaturase activity compared to the wild type protein
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LINKS TO OTHER DATABASES (specific for EC-Number 1.14.19.25)
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