Information on EC 2.7.8.2 - diacylglycerol cholinephosphotransferase

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

EC NUMBER
COMMENTARY hide
2.7.8.2
-
RECOMMENDED NAME
GeneOntology No.
diacylglycerol cholinephosphotransferase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
CDP-choline + 1,2-diacyl-sn-glycerol = CMP + a phosphatidylcholine
show the reaction diagram
REACTION TYPE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
substituted phospho group transfer
PATHWAY
BRENDA Link
KEGG Link
MetaCyc Link
choline biosynthesis III
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diacylglycerol biosynthesis (PUFA enrichment in oilseed)
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phosphatidylcholine biosynthesis I
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phosphatidylcholine biosynthesis II
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phosphatidylcholine resynthesis via glycerophosphocholine
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plasmalogen biosynthesis
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phosphatidylethanolamine bioynthesis
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Phosphonate and phosphinate metabolism
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Glycerophospholipid metabolism
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Ether lipid metabolism
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Metabolic pathways
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SYSTEMATIC NAME
IUBMB Comments
CDP-choline:1,2-diacyl-sn-glycerol cholinephosphotransferase
1-Alkyl-2-acylglycerol can act as acceptor; this activity was previously listed separately.
CAS REGISTRY NUMBER
COMMENTARY hide
77237-98-0
formerly, EC 2.7.8.16
9026-13-5
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ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
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-
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
L. ssp. Pekinensis, isoenzyme AAPT3
UniProt
Manually annotated by BRENDA team
cv. Galactica
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-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
f. sp. lycopersici
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Manually annotated by BRENDA team
cultivar Himalaya
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Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
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-
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Manually annotated by BRENDA team
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-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
evolution
the enzyme belongs to the CEPT subfamily
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
3-alpha-D-glucopyranosyl-1,2-di-palmitoylglycerol + CDP-choline
CMP + 3-(6-O-cholinephosphoryl-alpha-D-glucopyranosyl)-1,2-dipalmitoylglycerol
show the reaction diagram
CDP-choline + 1,2-diacyl-sn-glycerol
CMP + a phosphatidylcholine
show the reaction diagram
CDP-choline + 1,2-diacyl-sn-glycerol
CMP + phosphatidylcholine
show the reaction diagram
-
-
-
-
?
CDP-choline + 1,2-diacylglycerol
CMP + a phosphatidylcholine
show the reaction diagram
CDP-choline + 1,2-dioleoyl-sn-glycerol
?
show the reaction diagram
-
the most preferred diacylglycerol substrate is 18:0/20:4 diacylglycerol, followed by 18:0/22:6 diacylglycerol. The specific activities for 18:0/20:4 diacylglycerol and 18:0/22:6 diacylglycerol are 26 and 14fold higher than those of other diacylglycerol species
-
-
?
CDP-choline + 1,2-dioleoyl-sn-glycerol
CMP + 1,2-dioleoyl-sn-glycero-3-phosphocholine
show the reaction diagram
CDP-choline + 1,2-dipalmitoyl-sn-glycerol
CMP + 1,2-dipalmitoyl-sn-glycero-3-phosphocholine
show the reaction diagram
CDP-choline + 1-batyl-2-acetyl-sn-glycerol
CMP + 1-batyl-2-acetyl-sn-glycero-3-phosphocholine
show the reaction diagram
-
-
-
-
?
CDP-choline + 1-chimyl-2-acetyl-sn-glycerol
CMP + 1-chimyl-2-acetyl-sn-glycero-3-phosphocholine
show the reaction diagram
-
-
-
-
?
CDP-choline + 1-hexadecanoyl-2-octadecanoyl-sn-glycerol
CMP + 1-hexadecanoyl-2-octadecanoyl-sn-glycero-3-phosphocholine
show the reaction diagram
-
-
-
-
?
CDP-choline + 1-hexadecyl-2-acetyl-sn-glycerol
CMP + 1-hexadecyl-2-acetyl-sn-glycero-3-phosphocholine
show the reaction diagram
-
-
-
-
?
CDP-choline + 1-hexadecyl-2-octadecanoyl-sn-glycerol
CMP + 1-hexadecyl-2-octadecanoyl-sn-glycero-3-phosphocholine
show the reaction diagram
-
-
-
-
?
CDP-choline + 1-O-alkyl-2-acetyl-sn-glycerol
CMP + 1-O-alkyl-2-acetyl-sn-glycerol 3-phosphocholine
show the reaction diagram
CDP-choline + 1-O-hexadecyl-2-acetyl-sn-glycerol
CMP + 1-O-hexadecyl-2-acetyl-sn-glycero-phosphocholine
show the reaction diagram
-
-
-
-
?
CDP-choline + 1-palmitoyl-2-linoleoylglycerol
CMP + 1-palmitoyl-2-linoleoylglycero-3-phosphocholine
show the reaction diagram
CDP-choline + 1-selachyl-2-acetyl-sn-glycerol
CMP + 1-selachyl-2-acetyl-sn-glycero-3-phosphocholine
show the reaction diagram
-
-
-
-
?
CDP-choline + didecanoylglycerol
CMP + didecanoylglycerophosphocholine
show the reaction diagram
CDP-choline + dihexanoylglycerol
CMP + dihexanoylglycerophosphocholine
show the reaction diagram
CDP-choline + dioctanoylglycerol
CMP + dioctanoylglycerophosphocholine
show the reaction diagram
-
at 5-10% of the activity with dioleoylglycerol or egg diglycerides
-
-
?
CDP-choline + sn-1,2-diacylglycerol
?
show the reaction diagram
CDP-choline + sn-1,2-dioleoylglycerol
CMP + ?
show the reaction diagram
-
-
-
-
?
CDP-ethanolamine + 1,2-diacyl-sn-glycerol
CMP + a phosphatidylethanolamine
show the reaction diagram
CDP-ethanolamine + 1,2-diacylglycerol
CMP + phosphatidylethanolamine
show the reaction diagram
CMP + phosphatidylcholine
?
show the reaction diagram
CMP + phosphatidylcholine
CDP-choline + 1,2-diacylglycerol
show the reaction diagram
dCDP-choline + 1,2-diacylglycerol
CMP + 1,2-diacylglycero-3-phosphocholine
show the reaction diagram
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-
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?
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
3-alpha-D-glucopyranosyl-1,2-di-palmitoylglycerol + CDP-choline
CMP + 3-(6-O-cholinephosphoryl-alpha-D-glucopyranosyl)-1,2-dipalmitoylglycerol
show the reaction diagram
CDP-choline + 1,2-diacyl-sn-glycerol
CMP + a phosphatidylcholine
show the reaction diagram
CDP-choline + 1,2-diacyl-sn-glycerol
CMP + phosphatidylcholine
show the reaction diagram
-
-
-
-
?
CDP-choline + 1-O-alkyl-2-acetyl-sn-glycerol
CMP + 1-O-alkyl-2-acetyl-sn-glycerol 3-phosphocholine
show the reaction diagram
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platelet activating factor (PAF) de novo biosynthesis
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-
?
CDP-choline + sn-1,2-diacylglycerol
?
show the reaction diagram
CDP-ethanolamine + 1,2-diacyl-sn-glycerol
CMP + a phosphatidylethanolamine
show the reaction diagram
CMP + phosphatidylcholine
?
show the reaction diagram
additional information
?
-
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Co2+
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Mn2+, Mg2+ or Co2+ required, maximal activation: 10 mM
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1-butanol
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5'-AMP
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little effect
5'-GMP
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little effect
5'-UMP
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little effect
5-hydroxytryptamine
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butanol
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32% inhibition at 20 mM
CDPethanolamine
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CHAPS
chelerythrine
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inhibitor of protein kinase C, IC50 0.04 mM
cholate
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inactivation at solubilization concentration, full recovery of activity after reconstituting the membrane by adding excess lipid and removing detergent by gel filtration, dialysis or absorption to Bio-Beads, if membrane is solubilized with octylglucoside or cholate at weight ratios of detergent:membrane protein of at least 10, the activity is irreversibly lost unless stabilizers are added with detergent, diacylglycerol and glycerol are effective stabilizers
CMPcholine
dAcCDP-choline
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deoxycholate
DH-990
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hypolidemic drug
dithiothreitol
EDTA
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10 mM, in presence of 20 mM Mg2+
ethanol
Fatty acid esters
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INFalpha
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250 inhibitory units/microl, 51% inhibition of enzyme activity in microsomal fraction of mesangial cells
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methanol
Mg2+
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inhibitory above 10 mM, activation below
N,N-Dimethylaminoethanol
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less inhibitory than centrophenoxine
N,N-Dimethylaminoethyl p-chlorophenoxyacetate
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i.e. centrophenoxine
N-Methyl-D-aspartate
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strong
n-octylglucoside
NaF
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sodium fluoride, 50 mM, 40% reduction in activity
norepinephrine
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p-Chlorophenoxyacetic acid
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less inhibitory than centrophenoxine
p-hydroxymercuribenzoate
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palmitoyl-CoA
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Pentanol
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27% inhibition at 5 mM
Phospholipase A2
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Phospholipids
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phosphatidylcholine, phosphatidylethanolamine or lysophosphatidylethanolamine activates, lysophosphatidylcholine inhibits
polar lipids from olive oil
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5.2 ng/microl, 33% inhibition of enzyme activity in microsomal fraction of mesangial cells
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polar lipids from olive pomace
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1.8 ng/microl, 48% inhibition of enzyme activity in microsomal fraction of mesangial cells
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polar lipids from sea bass
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59 ng/microl, 45% inhibition of enzyme activity in microsomal fraction of mesangial cells
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polar lipids from sea bream
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123 ng/microl, 17% inhibition of enzyme activity in microsomal fraction of mesangial cells
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Propanol
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23% inhibition at 50 mM
R59949
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inhibitor of protein kinase C, IC50 0.04 mM
resveratrol
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100 microM, 39% inhibition of enzyme activity in microsomal fraction of mesangial cells
rupatadine
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20 ng/microl, 60% inhibition of enzyme activity in microsomal fraction of mesangial cells
salicylic acid
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250 ng/microl, 38% inhibition of enzyme activity in microsomal fraction of mesangial cells
SDS
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inactivation at solubilization concentration, full recovery of activity after reconstituting the membrane by adding excess lipid and removing detergent by gel filtration, dialysis or absorption to Bio-Beads
simvastatine
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40 ng/microl, 92% inhibition of enzyme activity in microsomal fraction of mesangial cells
tinzaparin
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0.25 inhibitory units/microl, 30% inhibition of enzyme activity in microsomal fraction of mesangial cells
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Triton X-100
Trypsin
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Tween-20
U-73122
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phospholipase C inhibitor, inhibition reversed by prostaglandin D2
additional information
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ACTIVATING COMPOUND
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
1,2-Dilaurin
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1,2-diolein
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highest stimulation of diacylglycerols tested
bovine serum albumin
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specific activity increases in presence of 0.5-2 mg/ml bovine serum albumin, microsomal fraction of human mesangial cells
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Cytidine nucleotides
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stimulate
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deoxycholate
dioleoylphosphatidylcholine
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stimulates
dithiothreitol
EDTA
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maximum activation at 0.5 mM, in presence of 20 mM Mg2+
EGTA
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0.5 mM, stimulates
ethylene glycol bis(beta-aminoethyl ether)-N,N,N',N'-tetraacetic acid
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stimulates
lysolecithin
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stimulates at low subsolubilizing concentrations, membrane-solubilizing concentrations lead to nearly complete inactivation
phorbol 12-myristate 13-acetate
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activates
phosphatidylcholine
phosphatidylethanolamine
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activates
Phospholipase C
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23°C, 10 min, slight stimulation
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Phospholipids
Prostaglandin D2
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up to 100% increase in activity
taurocholate
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stimulates
Triton X-100
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stimulates at low subsolubilizing concentrations, membrane-solubilizing concentrations lead to nearly complete inactivation
Tween-20
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stimulates at low subsolubilizing concentrations, membrane-solubilizing concentrations lead to nearly complete inactivation
unsaturated fatty acids
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a number of unsaturated fatty acids markedly stimulate, 0.8 mM oleate activates if a mixed diglyceride such as 1-palmitoyl-2-oleoyl-sn-glycerol is used as a substrate, dipalmitin or diolein incorporation into lecithin is not stimulated
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additional information
-
cholinephosphotransferase requires a lipidic boundary for full activation, no activation by substrate
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KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.12
1,2-dioleoyl-sn-glycerol
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30°C, pH 8.0
0.0509
1,2-dioleoylglycerol
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23°C, pH 8.5
0.16
1-arachidoyl-2-oleoyl-sn-glycerol
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30°C, pH 8.0
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0.17
1-heptadecanoyl-2-oleoyl-sn-glycerol
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30°C, pH 8.0
0.0143
1-hexadecanoyl-2-octadecanoyl-sn-glycerol
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pH 8.2, 30°C
0.0262
1-hexadecyl-2-octadecenoyl-sn-glycerol
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pH 8.2, 30°C
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0.133
1-lauroyl-2-oleoyl-sn-glycerol
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30°C, pH 8.0
0.104
1-myristoyl-2-oleoyl-sn-glycerol
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30°C, pH 8.0
0.21
1-nonadecanoyl-2-oleoyl-sn-glycerol
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30°C, pH 8.0
0.0593
1-O-alkyl-2-acetyl-sn-glycerol
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optimum reaction conditions, in presence of 100 microM CDP-choline
0.116
1-palmitoyl-2-oleoyl-sn-glycerol
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30°C, pH 8.0
0.109
1-pentadecanoyl-2-oleoyl-sn-glycerol
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30°C, pH 8.0
0.125 - 0.126
1-stearoyl-2-oleoyl-sn-glycerol
0.122
1-tridecanoyl-2-oleoyl-sn-glycerol
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30°C, pH 8.0
0.0405
bacterial diacylglycerol
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23°C, pH 8.5
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0.0166 - 0.53
CDP-choline
0.098 - 0.101
CDP-ethanolamine
0.125 - 0.35
CMP
0.0141
didecanoylglycerol
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23°C, pH 8.5
0.0057
didodecanoylglycerol
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23°C, pH 8.5
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0.0314
dihexadecanoylglycerol
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23°C, pH 8.5
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0.0681
dihexanoylglycerol
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23°C, pH 8.5
0.118
dimyristoyl-sn-glycerol
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23°C, pH 8.5
0.0501
dioctadecenoylglycerol
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23°C, pH 8.5
-
additional information
additional information
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.04
chelerythrine
Homo sapiens
-
inhibitor of protein kinase C, IC50 0.04 mM
0.04
R59949
Homo sapiens
-
inhibitor of protein kinase C, IC50 0.04 mM
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.0000003
-
0.01 mM Mg2+, microsomal fraction of human mesangial cells
0.0000012
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1 mM Mg2+, microsomal fraction of human mesangial cells
0.0000036
-
10 mM Mg2+, microsomal fraction of human mesangial cells
0.00002
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mitochondrial fraction of human mesangial cells
0.000067
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20 mM Mg2+, microsomal fraction of human mesangial cells
0.0001
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homogenate of human mesangial cells
0.00025
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20 mM Mg2+, 0.5 mM EDTA, microsomal fraction of human mesangial cells
0.00036
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microsomal fraction of human mesangial cells, maximum activity in presence of 1 mg/ml bovine serum albumin, 15 mM dithiothreitol, 20 mM Mg2+, 0.5 mM EDTA
0.00323
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substrate: CDP-choline, pH 7.5, 25°C
0.0132
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30°C, pH 7.4
0.13
-
37°C, pH 8.5
additional information
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
8.5 - 9.3
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-
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30
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assay at
additional information
-
temperature-dependence
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
A0A0H3U1R3, A0A0H3U1R4
developing, the isozymes are both highly expressed during the mid to late stages, 8 to 16 days after anthesis, DAA, of embryo development, peaking at approximately 11 DAA with transcript levels decreasing dramatically after 16 DAA to nearly undetectable levels for the remainder of seed development; developing, the isozymes are both highly expressed during the mid to late stages, 8 to 16 days after anthesis, DAA, of embryo development, peaking at approximately 11 DAA with transcript levels decreasing dramatically after 16 DAA to nearly undetectable levels for the remainder of seed development
Manually annotated by BRENDA team
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normal: MCF-12A and MCF-12F and cancerous: MCF-7, BT-549 and 11-9-1-4
Manually annotated by BRENDA team
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mesangial cell culture
Manually annotated by BRENDA team
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bacillus Calmette-Guerin induced rabbit
Manually annotated by BRENDA team
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HMC, immortilized by transfection with T-antigen of SV40 and Hras oncogene
Manually annotated by BRENDA team
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of intestine
Manually annotated by BRENDA team
-
inner medulla
Manually annotated by BRENDA team
additional information
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
additional information
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
30000
determined by SDS-PAGE
31100
theoretical
39000
-
x * 39000, hCPT1, SDS-PAGE and deduced from gene sequence
46500
-
x * 46500, hCEPT1, SDS-PAGE and deduced from gene sequence, seven membrane-spanning helices
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
19 min, stable, microsomal preparation
49
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15 min, 50% loss of activity, microsomal preparation
55
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1 min, 90% loss of activity, whole microsomes, less than 60% loss of activity, partially purified enzyme
60
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20 min heating results in total loss of activity, microsomal fraction of human mesangial cells (HMC)
65
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heat shock for 5min at 65°C significantly increases the activity of PGT
GENERAL STABILITY
ORGANISM
UNIPROT
LITERATURE
dithiothreitol stabilizes
-
freezing and thawing the microsomal preparation 5times destroys activity by 50%
-
no loss of activity by freezing and thawing one time
-
soy phosphatidylcholine protects against detergent inactivation
-
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-20°C, microsomal fraction of human mesangial cells (HMC), 30 days
-
4°C, 24 h, 10-15% loss of activity, partially purified liver enzyme
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
overview: purification
partial
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
DNA and amino acid sequence determination and analysis
expressed in NIH-3T3 cells
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expressed in the murine CH12 B-cell lymphoma cell line
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expressed in yeast
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gene CG7149, DNA and amino acid sequence determination and analysis, phylogenetic analysis, recombinant expression from vector mammalian expression vector pcDNA3.1/V5-His-TOPO in HeLa cells and in Drosophila S2 cells
gene GLYMA_12G0819001, DNA and amino acid sequence determination, analysis, and comparison, gene modeling using sequences Glyma02g14210 and Glyma12g08720, the soybean genome possesses two loci encoding the enzyme CPT, overview. Presence of binding sites for DNA-binding with one finger proteins in promoter regions of the gene model encoding CPT
gene PDCT1, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree, the gene sequences of isozymes LuPDCT1 and LuPDCT2 show very high nucleotide sequence identity of 97%, functional complementation of the enzyme-deficient rod1 mutant of Arabidopsis thaliana by expression of the seed-speficic isozymes, restoring polyunsaturated fatty acid levels (16.4% and 19.7% increases in C18-PUFAs, respectively, with a concomitant decrease in the proportion of oleic acid). Functional coexpression of the isozymes with fatty acid desaturases FAD2 and FAD3 in Saccharomyces cerevisiae leads to increased polyunsaturated fatty acid levels; gene PDCT2, DNA and amino acid sequence determination and analysis, sequence comparisons and phylogenetic tree, the gene sequences of isozymes LuPDCT1 and LuPDCT2 show very high nucleotide sequence identity of 97%, functional complementation of the enzyme-deficient rod1 mutant of Arabidopsis thaliana by expression of the seed-speficic isozymes, restoring polyunsaturated fatty acid levels (16.4% and 19.7% increases in C18-PUFAs, respectively, with a concomitant decrease in the proportion of oleic acid). Functional coexpression of the isozymes with fatty acid desaturases FAD2 and FAD3 in Saccharomyces cerevisiae leads to increased polyunsaturated fatty acid levels
A0A0H3U1R3, A0A0H3U1R4
genes PDCT1 and PDCT2, DNA and amino acid sequence determination and analysis, sequence comparisons
-
into the vectors pCRBluntII, pENTR/D-TOPO and pDEST14, finally the pDEST14 construct is used for the expression of the protein in Escherichia coli BL21-AI cells
isoenzyme AAPT3
overview
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
cholinephosphotransferase activity and its expression are significantly higher in breast cancer tissues
-
expression of PiCPT1 is upregulated in Phytophthora infestans organisms fed with exogenous very long-chain polyunsaturated fatty acids
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expression of the gene encoding CPT, but not CEPT, EC 2.7.8.1, increases during lipopolysaccahride-induced endoplasmic reticulum biogenesis in B-lymphocytes
gene cis-elements respond to biotic and abiotic stress, the enzyme is expressed under conditions of water or salinity stress, during infection with pathogens, in response to salicylic acid signaling, during somatic embryo differentiation, in immature seeds, in root tissues, and in soybean calli grown in the dark
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
since CPT expression is associated with elaboration of new endoplasmic reticulum membrane, it may be useful as a marker protein for endoplasmic reticulum expansion
biotechnology
medicine