Information on EC 3.1.3.76 - lipid-phosphate phosphatase

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The enzyme appears in viruses and cellular organisms

EC NUMBER
COMMENTARY hide
3.1.3.76
-
RECOMMENDED NAME
GeneOntology No.
lipid-phosphate phosphatase
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate + H2O = (9S,10S)-9,10-dihydroxyoctadecanoate + phosphate
show the reaction diagram
SYSTEMATIC NAME
IUBMB Comments
(9S,10S)-10-hydroxy-9-(phosphonooxy)octadecanoate phosphohydrolase
Requires Mg2+ for maximal activity. The enzyme from mammals is a bifunctional enzyme: the N-terminal domain exhibits lipid-phosphate-phosphatase activity and the C-terminal domain has the activity of EC 3.3.2.10, soluble epoxide hydrolase (sEH) [1]. The best substrates for this enzyme are 10-hydroxy-9-(phosphooxy)octadecanoates, with the threo- form being a better substrate than the erythro- form [1]. The phosphatase activity is not found in plant sEH or in EC 3.3.2.9, microsomal epoxide hydrolase, from mammals [1].
CAS REGISTRY NUMBER
COMMENTARY hide
9025-77-8
-
9048-63-9
-
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
-
-
-
Manually annotated by BRENDA team
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
physiological function
-
the N-terminal lipid phosphatase may play a role in the development of hypoxia-induced pulmonary hypertension
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(9E)-12-phosphonooxyoctadec-9-enoic acid + H2O
(9E)-12-hydroxyoctadec-9-enoic acid + phosphate
show the reaction diagram
-
-
-
-
?
(9E)-12-sulfonooxyoctadec-9-enoic acid + H2O
(9E)-12-hydroxyoctadec-9-enoic acid + sulfate
show the reaction diagram
-
-
-
-
?
(9Z)-12-phosphonooxyoctadec-9-enoic acid + H2O
(9Z)-12-hydroxyoctadec-9-enoic acid + phosphate
show the reaction diagram
-
-
-
-
?
(9Z)-12-sulfonooxyoctadec-9-enoic acid + H2O
(9Z)-12-hydroxyoctadec-9-enoic acid + sulfate
show the reaction diagram
-
-
-
-
?
10-sulfonooxy-octadecanoic acid + H2O
10-hydroxyoctadecanoic acid + phosphate
show the reaction diagram
-
-
-
-
?
12-phosphonooxyoctadecanoic acid + H2O
12-hydroxyoctadecanoic acid + phosphate
show the reaction diagram
-
-
-
-
?
2'-[2-benzothiazolyl]-6'-hydroxybenzothiazole phosphate + H2O
2'-[2-benzothiazolyl]-6'-hydroxybenzothiazole + phosphate
show the reaction diagram
-
i.e. attophos
-
-
?
4-methylumbelliferyl phosphate + H2O
4-methylumbelliferone + phosphate
show the reaction diagram
4-nitrophenyl phosphate + H2O
4-nitrophenol + phosphate
show the reaction diagram
erythro-10-phosphonooxy-9-hydroxy-octadecanoic acid + H2O
erythro-9,10-dihydroxyoctadecanoate + phosphate
show the reaction diagram
-
-
-
-
?
erythro-9,10-phosphonooxy-hydroxy-octadecanoic acid + H2O
?
show the reaction diagram
-
-
-
-
?
erythro-9-hydroxy-10-(phosphonooxy)octadecanoate + H2O
erythro-9,10-dihydroxyoctadecanoic acid + phosphate
show the reaction diagram
-
-
i.e. dihydroxy elaidic acid
-
?
farnesyl diphosphate + H2O
farnesol + phosphate
show the reaction diagram
-
-
-
-
?
farnesyl phosphate + H2O
farnesol + phosphate
show the reaction diagram
geranyl diphosphate + H2O
geraniol + phosphate
show the reaction diagram
-
-
-
-
?
geranyl phosphate + H2O
geraniol + phosphate
show the reaction diagram
geranylgeranyl diphosphate + H2O
geranylgeraniol + phosphate
show the reaction diagram
-
-
-
-
?
geranylgeranyl phosphate + H2O
geranylgeraniol + phosphate
show the reaction diagram
isopentenyl diphosphate + H2O
isopentenol + phosphate
show the reaction diagram
-
-
-
-
?
isopentenyl phosphate + H2O
isopentenol + phosphate
show the reaction diagram
threo-10-phosphonooxy-9-hydroxy-octadecanoic acid + H2O
threo-9,10-dihydroxyoctadecanoate + phosphate
show the reaction diagram
-
-
-
-
?
threo-9,10-phosphonooxy-hydroxy-octadecanoic acid + H2O
?
show the reaction diagram
-
-
-
-
?
threo-9,10-phosphonooxyoctadecanoic acid + H2O
?
show the reaction diagram
-
-
-
-
?
threo-9-hydroxy-10-(phosphonooxy)octadecanoate + H2O
threo-9,10-dihydroxyoctadecanoic acid + phosphate
show the reaction diagram
-
preferred substrate
i.e. dihydroxy stearic acid
-
?
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
(9E)-12-phosphonooxyoctadec-9-enoic acid + H2O
(9E)-12-hydroxyoctadec-9-enoic acid + phosphate
show the reaction diagram
-
-
-
-
?
(9Z)-12-phosphonooxyoctadec-9-enoic acid + H2O
(9Z)-12-hydroxyoctadec-9-enoic acid + phosphate
show the reaction diagram
-
-
-
-
?
12-phosphonooxyoctadecanoic acid + H2O
12-hydroxyoctadecanoic acid + phosphate
show the reaction diagram
-
-
-
-
?
erythro-9,10-phosphonooxy-hydroxy-octadecanoic acid + H2O
?
show the reaction diagram
-
-
-
-
?
threo-9,10-phosphonooxy-hydroxy-octadecanoic acid + H2O
?
show the reaction diagram
-
-
-
-
?
METALS and IONS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
Co2+
-
half as effective as Mg2+
phosphate
-
binding structure at the N-terminus
INHIBITORS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(9E)-12-sulfonooxy-9-octadecenoic acid
-
IC50 is 0.0097 mM
-
(9Z)-12-sulfonooxy-9-octadecenoic acid
-
IC50 is above 0.1 mM
-
10-sulfonooxyoctadecanoic acid
-
IC50 is 0.0059 mM
-
4-fluorochalcone oxide
-
8% inhibition at 0.1 mM
4-nitrophenyl sulfate
-
IC50 is above 0.1 mM
4-Phenylchalcone oxide
-
11% inhibition at 0.1 mM
9,10-hydroxysulfonooxyoctadecanoic acid
-
IC50 is 0.0175 mM
-
9-octadecanyl sulfate
-
IC50 is 0.0047 mM
-
alpha-hydroxyfarnesyl phosphonic acid
-
IC50 is 0.073 mM
alpha-sulfostearic acid
-
IC50 is 0.0096 mM
Cd2+
-
-
Cu2+
-
-
D-galactose 6-sulfate
-
IC50 is above 0.1 mM
dibenzyl phosphonate
-
IC50 is above 0.1 mM
diethyl 2,2,2-trifluoro-1-hydroxyethyl phosphonate
-
IC50 is above 0.1 mM
diethyl 4-methylbenzyl phosphonate
-
IC50 is above 0.1 mM
diethyl allyl phosphonate
-
IC50 is above 0.1 mM
diethyl benzoylphosphonate
-
IC50 is above 0.1 mM
diethyl cyclopropyl methylphosphonate
-
IC50 is above 0.1 mM
diethyl ethylthiomethyl phosphonate
-
IC50 is above 0.1 mM
diethyl trans-cinnamyl phosphonate
-
IC50 is above 0.1 mM
diethyl vinylphosphonate
-
IC50 is above 0.1 mM
dimethyl 2-oxoheptyl phosphonate
-
IC50 is above 0.1 mM
dioctyl phenyl phosphonate
-
IC50 is 0.013 mM
dodecyl phosphonic acid
-
IC50 is 0.040 mM
Estrone 3-sulfate
-
IC50 is above 0.1 mM
Hg2+
-
-
L-ascorbic acid 2-sulfate
-
IC50 is above 0.1 mM
-
N-acetyl-D-galactosamine 4-sulfate
-
IC50 is above 0.1 mM
orthovanadate
-
65% inhibition of the phosphatase activity at 0.1 mM
Sodium dodecyl sulfate
-
IC50 is 0.0052 mM
sodium dodecyl sulfonate
-
IC50 is 0.0037 mM
Sodium fluoride
-
10% inhibition at 1.0 mM
Sodium molybdate
-
8% inhibition at 1.0 mM
taurocholic acid
-
IC50 is above 0.1 mM
taurolithocholic acid 3-sulfate
-
IC50 is 0.005 mM
tetraisopropyl methylenediphosphonate
-
IC50 is above 0.1 mM
Zn2+
-
-
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0036
2'-[2-benzothiazolyl]-6'-hydroxybenzothiazole phosphate
-
pH 7.0, 30C, recombinant enzyme
0.21
4-methylumbelliferyl phosphate
-
pH 7.0, 30C, recombinant enzyme
0.24 - 2.5
4-nitrophenyl phosphate
0.0036 - 0.084
farnesyl diphosphate
0.0036
farnesyl monophosphate
-
pH 7.0, 30C, recombinant enzyme
0.024
farnesyl phosphate
-
recombinant enzyme
0.124
geranyl phosphate
-
recombinant enzyme
0.0036 - 0.033
geranylgeranyl diphosphate
1.746
geranylgeranyl phosphate
-
recombinant enzyme
0.02
threo-10-phosphonooxy-9-hydroxy-octadecanoic acid
-
pH 7.0, 30C, recombinant enzyme
0.021
threo-9,10-phosphonooxyoctadecanoic acid
-
pH 7.0, 30C, recombinant enzyme
0.021
threo-9-hydroxy-10-(phosphonooxy)octadecanoate
-
pH 7.8, 37C, recombinant enzyme
additional information
additional information
-
TURNOVER NUMBER [1/s]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0061 - 1.61
4-nitrophenyl phosphate
0.25
farnesyl diphosphate
-
recombinant enzyme
0.71
farnesyl phosphate
-
recombinant enzyme
0.51
geranyl phosphate
-
recombinant enzyme
0.13
geranylgeranyl diphosphate
-
recombinant enzyme
1.85
geranylgeranyl phosphate
-
recombinant enzyme
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
additional information
additional information
-
inhibition kinetics
-
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0097
(9E)-12-sulfonooxy-9-octadecenoic acid
Homo sapiens
-
IC50 is 0.0097 mM
-
0.1
(9Z)-12-sulfonooxy-9-octadecenoic acid
Homo sapiens
-
IC50 is above 0.1 mM
-
0.0059
10-sulfonooxyoctadecanoic acid
Homo sapiens
-
IC50 is 0.0059 mM
-
0.1
4-nitrophenyl sulfate
Homo sapiens
-
IC50 is above 0.1 mM
0.0175
9,10-hydroxysulfonooxyoctadecanoic acid
Homo sapiens
-
IC50 is 0.0175 mM
-
0.0047
9-octadecanyl sulfate
Homo sapiens
-
IC50 is 0.0047 mM
-
0.073
alpha-hydroxyfarnesyl phosphonic acid
Homo sapiens
-
IC50 is 0.073 mM
0.0096
alpha-sulfostearic acid
Homo sapiens
-
IC50 is 0.0096 mM
0.1
D-galactose 6-sulfate
Homo sapiens
-
IC50 is above 0.1 mM
0.1
dibenzyl phosphonate
Homo sapiens
-
IC50 is above 0.1 mM
0.1
diethyl 2,2,2-trifluoro-1-hydroxyethyl phosphonate
Homo sapiens
-
IC50 is above 0.1 mM
0.1
diethyl 4-methylbenzyl phosphonate
Homo sapiens
-
IC50 is above 0.1 mM
0.1
diethyl allyl phosphonate
Homo sapiens
-
IC50 is above 0.1 mM
0.1
diethyl benzoylphosphonate
Homo sapiens
-
IC50 is above 0.1 mM
0.1
diethyl cyclopropyl methylphosphonate
Homo sapiens
-
IC50 is above 0.1 mM
0.1
diethyl ethylthiomethyl phosphonate
Homo sapiens
-
IC50 is above 0.1 mM
0.1
diethyl trans-cinnamyl phosphonate
Homo sapiens
-
IC50 is above 0.1 mM
0.1
diethyl vinylphosphonate
Homo sapiens
-
IC50 is above 0.1 mM
0.1
dimethyl 2-oxoheptyl phosphonate
Homo sapiens
-
IC50 is above 0.1 mM
0.013
dioctyl phenyl phosphonate
Homo sapiens
-
IC50 is 0.013 mM
0.04
dodecyl phosphonic acid
Homo sapiens
-
IC50 is 0.040 mM
0.1
Estrone 3-sulfate
Homo sapiens
-
IC50 is above 0.1 mM
0.1
L-ascorbic acid 2-sulfate
Homo sapiens
-
IC50 is above 0.1 mM
-
0.1
N-acetyl-D-galactosamine 4-sulfate
Homo sapiens
-
IC50 is above 0.1 mM
0.0052
Sodium dodecyl sulfate
Homo sapiens
-
IC50 is 0.0052 mM
0.0037
sodium dodecyl sulfonate
Homo sapiens
-
IC50 is 0.0037 mM
0.1
taurocholic acid
Homo sapiens
-
IC50 is above 0.1 mM
0.005
taurolithocholic acid 3-sulfate
Homo sapiens
-
IC50 is 0.005 mM
0.1
tetraisopropyl methylenediphosphonate
Homo sapiens
-
IC50 is above 0.1 mM
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
0.007
-
purified recombinant mutant R103C/R287Q, substrate 4-nitrophenyl phosphate
0.015
-
purified recombinant mutant K55R, substrate 4-nitrophenyl phosphate
0.016
-
purified recombinant mutant C154Y, substrate 4-nitrophenyl phosphate
0.017
-
purified recombinant mutant R103C, substrate 4-nitrophenyl phosphate
0.021
-
purified recombinant mutant R287Q, substrate 4-nitrophenyl phosphate
0.029
-
purified recombinant wild-type allele MFA enzyme and mutant E470G, substrate 4-nitrophenyl phosphate
0.0954
-
purified recombinant enzyme
0.25
-
purified recombinant enzyme, substrate geranyl phosphate
0.49
-
purified recombinant enzyme, substrate farnesyl phosphate
0.53
-
purified recombinant enzyme, substrate geranylgeranyl phosphate
0.8
-
purified recombinant enzyme, substrate geranyl phosphate
0.85
-
purified recombinant enzyme, substrate isopentenyl phosphate
0.99
-
purified recombinant enzyme, substrate farnesyl phosphate
1.05
-
purified recombinant enzyme, substrate geranylgeranyl phosphate
additional information
-
optimization of activity assay conditions with the recombinant enzyme, maximal in 25 mM Tris buffer, pH 7.0, 30C, 1 mM MgCl2
pH OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
7.4
-
assay at
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
-
-
-
Manually annotated by BRENDA team
PDB
SCOP
CATH
ORGANISM
UNIPROT
SUBUNITS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
Crystallization/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
crystal structure analysis
-
purified recombinant enzyme, sitting drop vapour diffusion method, 0.005 ml of 12-16 mg/ml protein in 3 mM DTT, 0.1 M sodium phosphate, pH 7.4, is mixed with 0.005 ml precipitation solution containing 0.1 M Tris, pH 9.0, 30% w/v PEG 4000, and 0.2 M Li2SO4, versus 1 ml reservoir of precipitatin solution, 4C, 10 days, X-ray diffraction structure determination and analysis at 2.6 A resolution, modeling
-
TEMPERATURE STABILITY
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
-
inactivation rate constants for recombinant wild-type and mutant enzymes
STORAGE STABILITY
ORGANISM
UNIPROT
LITERATURE
-70C, 0.5 mg/ml purified enzyme, completely stable
-
Purification/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
from liver to homogeneity by ultracentrifugation and affinity chromatography on a benzyl thio resin using 4-fluorochalcone oxide as eluent
-
recombinant enzyme by S-benzyl affinity chromatography with 4-fluorochalcone oxide as eluent
-
recombinant His-tagged wild-type and D9A mutant enzymes and N-terminal domains from Escherichia coli strain BL21-AI by nickel affinity chromatography, recombinant strep-tagged wild-type enzyme from Escherichia coli strain XL1-Blue by streptavidin affinity chromatography
-
recombinant His-tagged wild-type and mutant enzymes from insect cells by nickel affinity chromatography
-
recombinant His-tagged wild-type and mutant enzymes from Sf21 insect cells by nickel affinity chromatography
-
recombinant wild-type and mutant enzymes from insect cells by affinity chromatography
-
Cloned/COMMENTARY
ORGANISM
UNIPROT
LITERATURE
arabinose-inducible expression of His-tagged wild-type and D9A mutant enzymes and N-terminal domains from cDNA in Escherichia coli strain BL21-AI, expression of strep-tagged enzyme from full-length gene in Escherichia coli strain XL1-Blue
-
arabinose-inducible expression of the enzyme from full-length gene in Escherichia coli strain BL21-AI
-
expression of enzyme in insect cells using the baculovirus infection system
-
expression of His-tagged wild-type and mutant enzymes in insect cells using the baculovirus infection system
-
expression of wild-type and mutant enzymes in insect cells using the baculovirus infection system
-
gene EPHX2, expression of His-tagged wild-type and mutant enzymes in Spodoptera frugiperda Sf21 cells using the baculovirus infection system
-
ENGINEERING
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
D9A
-
site-directed mutagenesis, inactive mutant N-terminal domain
E470G
-
site-directed mutagenesis, the mutant shows a hydrolase/phosphatase ratio of 0.9, compared to the wild-type ratio of 1.0
K55R
-
site-directed mutagenesis, the mutant shows a hydrolase/phosphatase ratio of 1.9, compared to the wild-type ratio of 1.0
R103C/R287Q
V422A
-
site-directed mutagenesis, the mutant shows a hydrolase/phosphatase ratio of 0.8, compared to the wild-type ratio of 1.0
Y465F
-
site-directed mutagenesis, mutant enzyme shows phosphatase, but no epoxide hydrolase activity
additional information
-
the isolated recombinant N-terminal domain is a fully active phosphatase