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Information on EC 4.1.2.27 - sphinganine-1-phosphate aldolase and Organism(s) Homo sapiens and UniProt Accession O95470

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EC Tree
     4 Lyases
         4.1 Carbon-carbon lyases
             4.1.2 Aldehyde-lyases
                4.1.2.27 sphinganine-1-phosphate aldolase
IUBMB Comments
A pyridoxal-phosphate protein.
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Select one or more organisms in this record: ?
This record set is specific for:
Homo sapiens
UNIPROT: O95470
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Word Map
The taxonomic range for the selected organisms is: Homo sapiens
The expected taxonomic range for this enzyme is: Eukaryota, Archaea, Bacteria
Synonyms
s1p lyase, sgpl1, sphingosine-1-phosphate lyase, s1p-lyase, sphingosine phosphate lyase, sphingosine 1-phosphate lyase, legs2, dpl1p, s1pl2021, sphingosine-phosphate lyase, more
SYNONYM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
S1P lyase
-
sphingosine 1-phosphate lyase
-
sphingosine-1-phosphate lyase
-
aldolase, dihydrosphingosine 1-phosphate
-
-
-
-
Dihydrosphingosine 1-phosphate aldolase
-
-
-
-
dihydrosphingosine phosphate lyase
-
-
Dpl1
-
-
S1P-lyase
-
-
sphinganine 1-phosphate lyase
-
-
-
-
sphinganine-1-phosphate aldolase
-
-
-
-
sphinganine-1-phosphate-alkanal-lyase
-
-
-
-
sphingosine 1-phosphate lyase
-
-
sphingosine phosphate lyase
-
-
sphingosine-1-phosphate lyase
sphingosine-phosphate lyase
-
-
-
-
REACTION
REACTION DIAGRAM
COMMENTARY hide
ORGANISM
UNIPROT
LITERATURE
Sphinganine 1-phosphate = phosphoethanolamine + palmitaldehyde
show the reaction diagram
enzyme has been classified within the group of carbon-carbon lyases a subclass of aldehyde-lyases (Enzyme Nomenclature 1984)
-
PATHWAY SOURCE
PATHWAYS
-
-
SYSTEMATIC NAME
IUBMB Comments
sphinganine-1-phosphate palmitaldehyde-lyase (phosphoethanolamine-forming)
A pyridoxal-phosphate protein.
CAS REGISTRY NUMBER
COMMENTARY hide
37290-61-2
-
SUBSTRATE
PRODUCT                       
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
Reversibility
r=reversible
ir=irreversible
?=not specified
(2S,3R,4E)-2-ammonio-3-hydroxy-7-((2-oxo-2H-chromen-7-yl)oxy)hept-4-en-1-yl hydrogenphosphate
?
show the reaction diagram
i.e. RBM77
-
-
?
(2S,3R,5E)-2-ammonio-3-hydroxy-7-((2-oxo-2H-chromen-7-yl)oxy)hept-5-en-1-yl hydrogenphosphate
?
show the reaction diagram
i.e. RBM148
-
-
?
sphinganine 1-phosphate
phosphoethanolamine + palmitaldehyde
show the reaction diagram
sphingosine 1-phosphate
phosphoethanolamine + (2E)-hexadecenal
show the reaction diagram
-
-
-
ir
sphingosine 1-phosphate
phosphoethanolamine + palmitaldehyde
show the reaction diagram
-
-
ir
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-labeled sphinganine 1-phosphate
phosphoethanolamine + 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-labeled palmitaldehyde
show the reaction diagram
-
i.e. BODIPY-label, allows fluorescent product detection by HPLC
major aldehyde product is confirmed by reaction with 2,4-dinitrophenylhydrazine
-
?
7-nitrobenz-2-oxa-1,3-diazole-sphingosine 1-phosphate
phosphoethanolamine + 7-nitrobenz-2-oxa-1,3-diazole-hexadec-2-enal
show the reaction diagram
-
-
-
-
?
boron dipyrromethene difluoride-sphingosine 1-phosphate
phosphoethanolamine + boron dipyrromethene difluoride-hexadec-2-enal
show the reaction diagram
-
-
-
-
?
D-(+)-erythro-sphingosine 1-phosphate
phosphoethanolamine + (2E)-hexadecenal
show the reaction diagram
-
-
-
-
ir
dihydrosphingosine 1-phosphate
phosphoethanolamine + palmitaldehyde
show the reaction diagram
-
-
-
-
?
Dihydrosphingosine 1-phosphonate
Aminoethylphosphonate + palmidaldehyde
show the reaction diagram
-
-
-
-
?
phytosphingosine-1-phosphate
?
show the reaction diagram
-
-
-
-
?
RBM13
?
show the reaction diagram
-
-
-
-
?
sphinganine 1-phosphate
phosphoethanolamine + palmitaldehyde
show the reaction diagram
sphingosine 1-phosphate
phosphoethanolamine + (2E)-hexadecenal
show the reaction diagram
sphingosine 1-phosphate
phosphoethanolamine + palmitaldehyde
show the reaction diagram
umbelliferone-labled sphinganine 1-phosphate
phosphoethanolamine + 3-[(2-oxo-2H-chromen-7-yl)oxy]propanal
show the reaction diagram
-
-
-
-
?
additional information
?
-
NATURAL SUBSTRATE
NATURAL PRODUCT
REACTION DIAGRAM
ORGANISM
UNIPROT
COMMENTARY
(Substrate) hide
LITERATURE
(Substrate)
COMMENTARY
(Product) hide
LITERATURE
(Product)
REVERSIBILITY
r=reversible
ir=irreversible
?=not specified
sphinganine 1-phosphate
phosphoethanolamine + palmitaldehyde
show the reaction diagram
sphinganine 1-phosphate
phosphoethanolamine + palmitaldehyde
show the reaction diagram
additional information
?
-
COFACTOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
pyridoxal 5'-phosphate
-
pyridoxal 5'-phosphate
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
(R)-1-benzyl-4-(3-methyl-4-(5-(trifluoromethyl)pyridin-2-yl)-piperazin-1-yl)phthalazine
-
-
(R)-1-benzyl-4-(3-methyl-4-(5-nitropyridin-2-yl)piperazin-1-yl)-phthalazine
-
-
(R)-1-benzyl-4-(4-(5-cyanopyridin-2-yl)-3-methylpiperazin-1-yl)phthalazine-6-carbonitrile
-
-
(R)-4-benzyl-1-(4-(5-cyanopyridin-2-yl)-3-methylpiperazin-1-yl)phthalazine-6-carbonitrile
-
-
(R)-6-(2-methyl-4-(4-phenethylphthalazin-1-yl)piperazin-1-yl)nicotinonitrile
-
-
(R)-6-(2-methyl-4-(4-phenylphthalazin-1-yl)piperazin-1-yl)-nicotinonitrile
-
-
(R)-6-(4-(4-benzyl-6-(trifluoromethyl)phthalazin-1-yl)-2-methylpiperazin-1-yl)nicotinonitrile
-
-
(R)-6-(4-(4-benzyl-6-chlorophthalazin-1-yl)-2-methylpiperazin-1-yl)nicotinonitrile
-
-
(R)-6-(4-(4-benzyl-7-(trifluoromethyl)phthalazin-1-yl)-2-methylpiperazin-1-yl)nicotinonitrile
-
-
(R)-6-(4-(4-benzyl-7-chlorophthalazin-1-yl)-2-methylpiperazin-1-yl)nicotinonitrile
-
-
(R)-6-(4-(4-benzylphthalazin-1-yl)-2-ethylpiperazin-1-yl)nicotinonitrile
-
-
(R)-6-(4-(4-benzylphthalazin-1-yl)-2-isopropylpiperazin-1-yl)-nicotinonitrile
-
-
(R)-6-(4-(4-benzylphthalazin-1-yl)-2-methylpiperazin-1-yl)-nicotinic acid
-
-
(R)-6-(4-(4-chlorophthalazin-1-yl)-2-methylpiperazin-1-yl)-nicotinonitrile
-
-
(S)-6-(4-(4-benzylphthalazin-1-yl)-2-(hydroxymethyl)piperazin-1-yl)nicotinonitrile
-
-
2-acetyl-4-tetrahydroxybutylimidazole
6-[(2R)-4-(4-benzylphthalazin-1-yl)-2-methylpiperazin-1-yl]pyridine-3-carbonitrile
-
6-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]pyridine-3-carbonitrile
-
deoxypyridoxine
-
ethyl 6-[(2R)-4-(4-benzylphthalazin-1-yl)-2-methylpiperazin-1-yl]pyridine-3-carboxylate
-
[(4-benzylphthalazin-1-yl)-2-methylpiperazin-1-yl]nicotinonitrile
-
(2R,3R)-2-azido-3-hydroxyoctadecyl phosphate
-
-
(2R,3R,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl phosphate
-
-
(2R,3S)-2-azido-3-hydroxyoctadecyl phosphate
-
-
(2R,3S,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl phosphate
-
-
(2S,3R)-2-azido-3-hydroxyoctadecyl phosphate
-
-
(2S,3R,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl phosphate
-
-
(2S,3S)-2-azido-3-hydroxyoctadecyl phosphate
-
-
(2S,3S,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl phosphate
-
-
1-benzyl-4-[(3R)-4-(5-cyanopyridin-2-yl)-3-methylpiperazin-1-yl]phthalazine-6-carbonitrile
-
-
1-deoxydihydrosphingosine 1-phosphonate
1-deoxysphinganine 1-phosphonate
-
-
1-desoxysphinganine 1-phosphonate
-
competitive inhibitor
2-acetyl-4-(1R,2S,3R,4-tetrahydroxybutyl)-1H-imidazole
-
-
2-acetyl-4-(1R,2S,3R,4-tetrahydroxybutyl)-imidazole
-
-
2-acetyl-4-tetrahydroxybutyl-imidazole
-
-
2-acetyl-4-tetrahydroxybutylimidazole
-
-
2-vinyl dihydrosphingosine
-
-
2-vinyldihydro-sphingosine 1-phosphate
-
-
2-vinyldihydrosphingosine 1-phosphate
-
-
2-vinylsphinganine 1-phosphate
-
-
4'-deoxypyridoxine
4-amino-N-[4-(1H-imidazol-1-yl)benzyl]-5-oxo-2-(piperidin-1-yl)-8-(tetrahydrofuran-2-ylmethyl)-5,8-dihydropyrido[2,3-d]pyrimidine-6-carboxamide
-
-
4-deoxypyridoxine
-
-
5-cyclopropyl-N-[2-[(4-ethoxy-2,5-dimethylbenzyl)amino]-1-(4-fluorophenyl)ethyl]-1,2-oxazole-3-carboxamide
-
-
5-cyclopropyl-N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-phenylethyl]-1,2-oxazole-3-carboxamide
-
-
5-methoxy-N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-phenylethyl]-1,2-oxazole-3-carboxamide
-
-
6-[(2R)-4-(4-benzyl-7-chlorophthalazin-1-yl)-2-methylpiperazin-1-yl]pyridine-3-carbonitrile
-
-
6-[(2R)-4-(4-benzylphthalazin-1-yl)-2-methylpiperazin-1-yl]pyridine-3-carbonitrile
-
-
benzylphthalazine
-
-
bisulfite
-
-
Ca2+
-
-
carboplatin
-
cells overexpressing enzyme show increased sensitivity
cisplatin
-
cells overexpressing enzyme show increased sensitivity, mediated by death kinase p38
cyanide
-
-
cysteine
-
-
deoxypyridoxine
-
competitive inhibitor
doxorubicin
-
cells overexpressing enzyme show increased sensitivity
FTY720
FTY720 phosphate
-
less potent inhibitor than FTY720, effects only at 0.03 mM
LX2931
-
-
N-(2-[[2,5-dimethyl-4-(2,2,2-trifluoroethoxy)benzyl]amino]-1-phenylethyl)-5-methyl-1,2-oxazole-3-carboxamide
-
-
N-(2-[[2,5-dimethyl-4-(pyridin-4-ylmethoxy)benzyl]amino]-1-phenylethyl)-5-methyl-1,2-oxazole-3-carboxamide
-
-
N-(2-[[4-methoxy-2-methyl-5-(trifluoromethyl)benzyl]amino]-1-phenylethyl)-5-methyl-1,2-oxazole-3-carboxamide
-
-
N-[(1R,2S)-2-hydroxy-1-hydroxymethyl-2-(2-tridecyl-1-cyclopentenyl)ethyl]octanamide
-
-
N-[1-(4-fluorophenyl)-2-[(4-methoxy-2,5-dimethylbenzyl)amino]ethyl]-5-methyl-1,2-oxazole-3-carboxamide
-
-
N-[1-[3-(4-amino-4-oxobutyl)phenyl]-2-[(4-methoxy-2,5-dimethylbenzyl)amino]ethyl]-5-methyl-1,2-oxazole-3-carboxamide
-
-
N-[1-[4-(3-hydroxyprop-1-yn-1-yl)phenyl]-2-[(4-methoxy-2,5-dimethylbenzyl)amino]ethyl]-5-methyl-1,2-oxazole-3-carboxamide
-
-
N-[1-[4-(4-amino-4-oxobutyl)phenyl]-2-[(4-methoxy-2,5-dimethylbenzyl)amino]ethyl]-5-methyl-1,2-oxazole-3-carboxamide
-
-
N-[2-[(4-butoxy-2,5-dimethylbenzyl)amino]-1-phenylethyl]-5-methyl-1,2-oxazole-3-carboxamide
-
-
N-[2-[(4-ethoxy-2,5-dimethylbenzyl)amino]-1-phenylethyl]-5-methyl-1,2-oxazole-3-carboxamide
-
-
N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-(2-methoxyphenyl)ethyl]-5-methyl-1,2-oxazole-3-carboxamide
-
-
N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-(3-methoxyphenyl)ethyl]-5-methyl-1,2-oxazole-3-carboxamide
-
-
N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-(4-methoxyphenyl)ethyl]-5-methyl-1,2-oxazole-3-carboxamide
-
-
N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-phenylethyl]-1,2-oxazole-3-carboxamide
-
-
N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-phenylethyl]-3-methyl-1,2-oxazole-5-carboxamide
-
-
N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-phenylethyl]-5-methyl-1,2-oxazole-3-carboxamide
-
-
N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-[4-(pyridin-4-yl)phenyl]ethyl]-5-methyl-1,2-oxazole-3-carboxamide
-
-
N-[2-[(4-methoxybenzyl)amino]-1-phenylethyl]-5-methyl-1,2-oxazole-3-carboxamide
-
-
phosphopyridoxyl sphinganine 1-phosphate
-
-
phosphopyridoxyl sphingosine 1-phosphate
-
-
Semicarbazide
threo-dihydro-sphingosine 1-phosphate
-
-
Zn2+
-
-
[2-amino-2[2-(4-octylphenyl)ethyl]-3-hydroxypropyl]dihydrogen phosphate
-
-
additional information
-
KM VALUE [mM]
SUBSTRATE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.035
4,4-difluoro-4-bora-3a,4a-diaza-s-indacene-labeled sphinganine 1-phosphate
-
37°C
0.0201
Dihydrosphingosine 1-phosphonate
-
in 0.6 mM EDTA, 0.4 mM pyridoxal 5'-phosphate, 3 mM dithiothreitol mM sucrose, 36 mM potassium phosphate buffer, and 36 mM NaF containing 0.08% Triton X-100
0.0146
sphingosine 1-phosphate
-
in 0.6 mM EDTA, 0.4 mM pyridoxal 5'-phosphate, 3 mM dithiothreitol mM sucrose, 36 mM potassium phosphate buffer, and 36 mM NaF containing 0.08% Triton X-100
Ki VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.0367
(2R,3R)-2-azido-3-hydroxyoctadecyl phosphate
-
at pH 10.6 and 37°C
0.0175
(2R,3R,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl phosphate
-
at pH 10.6 and 37°C
0.0063
(2R,3S)-2-azido-3-hydroxyoctadecyl phosphate
-
at pH 10.6 and 37°C
0.0056
(2R,3S,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl phosphate
-
at pH 10.6 and 37°C
0.019
(2S,3R)-2-azido-3-hydroxyoctadecyl phosphate
-
at pH 10.6 and 37°C
0.0091
(2S,3R,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl phosphate
-
at pH 10.6 and 37°C
0.0164
(2S,3S)-2-azido-3-hydroxyoctadecyl phosphate
-
at pH 10.6 and 37°C
0.0204
(2S,3S,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl phosphate
-
at pH 10.6 and 37°C
0.005
1-deoxydihydrosphingosine 1-phosphonate
-
pH and temperature not specified in the publication
0.005
1-deoxysphinganine 1-phosphonate
-
at pH 10.6 and 37°C
IC50 VALUE [mM]
INHIBITOR
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
IMAGE
0.03
(R)-1-benzyl-4-(3-methyl-4-(5-(trifluoromethyl)pyridin-2-yl)-piperazin-1-yl)phthalazine
Homo sapiens
at pH 7.4 and 25°C
-
0.00074
(R)-1-benzyl-4-(3-methyl-4-(5-nitropyridin-2-yl)piperazin-1-yl)-phthalazine
Homo sapiens
at pH 7.4 and 25°C
-
0.000024
(R)-1-benzyl-4-(4-(5-cyanopyridin-2-yl)-3-methylpiperazin-1-yl)phthalazine-6-carbonitrile
Homo sapiens
at pH 7.4 and 25°C
-
0.0013
(R)-4-benzyl-1-(4-(5-cyanopyridin-2-yl)-3-methylpiperazin-1-yl)phthalazine-6-carbonitrile
Homo sapiens
at pH 7.4 and 25°C
-
0.03
(R)-6-(2-methyl-4-(4-phenethylphthalazin-1-yl)piperazin-1-yl)nicotinonitrile
Homo sapiens
at pH 7.4 and 25°C
-
0.03
(R)-6-(2-methyl-4-(4-phenylphthalazin-1-yl)piperazin-1-yl)-nicotinonitrile
Homo sapiens
IC50 above 0.03 mM, at pH 7.4 and 25°C
-
0.012
(R)-6-(4-(4-benzyl-6-(trifluoromethyl)phthalazin-1-yl)-2-methylpiperazin-1-yl)nicotinonitrile
Homo sapiens
at pH 7.4 and 25°C
-
0.0023
(R)-6-(4-(4-benzyl-6-chlorophthalazin-1-yl)-2-methylpiperazin-1-yl)nicotinonitrile
Homo sapiens
at pH 7.4 and 25°C
-
0.0001
(R)-6-(4-(4-benzyl-7-(trifluoromethyl)phthalazin-1-yl)-2-methylpiperazin-1-yl)nicotinonitrile
Homo sapiens
at pH 7.4 and 25°C
-
0.00021
(R)-6-(4-(4-benzyl-7-chlorophthalazin-1-yl)-2-methylpiperazin-1-yl)nicotinonitrile
Homo sapiens
at pH 7.4 and 25°C
-
0.0017
(R)-6-(4-(4-benzylphthalazin-1-yl)-2-ethylpiperazin-1-yl)nicotinonitrile
Homo sapiens
at pH 7.4 and 25°C
-
0.0025
(R)-6-(4-(4-benzylphthalazin-1-yl)-2-isopropylpiperazin-1-yl)-nicotinonitrile
Homo sapiens
at pH 7.4 and 25°C
-
0.03
(R)-6-(4-(4-benzylphthalazin-1-yl)-2-methylpiperazin-1-yl)-nicotinic acid, (R)-6-(4-(4-chlorophthalazin-1-yl)-2-methylpiperazin-1-yl)-nicotinonitrile
Homo sapiens
IC50 above 0.03 mM, at pH 7.4 and 25°C
-
0.03
(R)-6-(4-(4-chlorophthalazin-1-yl)-2-methylpiperazin-1-yl)-nicotinonitrile
Homo sapiens
-
IC50 above 0.03 mM, at pH 7.4 and 25°C
-
0.03
(S)-6-(4-(4-benzylphthalazin-1-yl)-2-(hydroxymethyl)piperazin-1-yl)nicotinonitrile
Homo sapiens
IC50 above 0.03 mM, at pH 7.4 and 25°C
-
0.0024 - 0.03
6-[(2R)-4-(4-benzylphthalazin-1-yl)-2-methylpiperazin-1-yl]pyridine-3-carbonitrile
0.03
6-[4-(4-benzylphthalazin-1-yl)piperazin-1-yl]pyridine-3-carbonitrile
Homo sapiens
IC50 above 0.03 mM, at pH 7.4 and 25°C
0.0034
ethyl 6-[(2R)-4-(4-benzylphthalazin-1-yl)-2-methylpiperazin-1-yl]pyridine-3-carboxylate
Homo sapiens
at pH 7.4 and 25°C
0.0283
(2R,3R)-2-azido-3-hydroxyoctadecyl phosphate
Homo sapiens
-
at pH 10.6 and 37°C
0.0229
(2R,3R,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl phosphate
Homo sapiens
-
at pH 10.6 and 37°C
0.0108
(2R,3S)-2-azido-3-hydroxyoctadecyl phosphate
Homo sapiens
-
at pH 10.6 and 37°C
0.0052
(2R,3S,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl phosphate
Homo sapiens
-
at pH 10.6 and 37°C
0.0257
(2S,3R)-2-azido-3-hydroxyoctadecyl phosphate
Homo sapiens
-
at pH 10.6 and 37°C
0.0101
(2S,3R,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl phosphate
Homo sapiens
-
at pH 10.6 and 37°C
0.0218
(2S,3S)-2-azido-3-hydroxyoctadecyl phosphate
Homo sapiens
-
at pH 10.6 and 37°C
0.0288
(2S,3S,4E)-2-azido-3-hydroxyoctadec-4-en-1-yl phosphate
Homo sapiens
-
at pH 10.6 and 37°C
0.0024
2-vinyldihydrosphingosine 1-phosphate
Homo sapiens
-
at pH 10.6 and 37°C
0.0024
2-vinylsphinganine 1-phosphate
Homo sapiens
-
pH and temperature not specified in the publication
0.0046
5-cyclopropyl-N-[2-[(4-ethoxy-2,5-dimethylbenzyl)amino]-1-(4-fluorophenyl)ethyl]-1,2-oxazole-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00073
5-cyclopropyl-N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-phenylethyl]-1,2-oxazole-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.0092
5-methoxy-N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-phenylethyl]-1,2-oxazole-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.0524
FTY720
0.00059
N-(2-[[2,5-dimethyl-4-(2,2,2-trifluoroethoxy)benzyl]amino]-1-phenylethyl)-5-methyl-1,2-oxazole-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.001
N-(2-[[2,5-dimethyl-4-(pyridin-4-ylmethoxy)benzyl]amino]-1-phenylethyl)-5-methyl-1,2-oxazole-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.0012
N-(2-[[4-methoxy-2-methyl-5-(trifluoromethyl)benzyl]amino]-1-phenylethyl)-5-methyl-1,2-oxazole-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00072
N-[1-(4-fluorophenyl)-2-[(4-methoxy-2,5-dimethylbenzyl)amino]ethyl]-5-methyl-1,2-oxazole-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.0096
N-[1-[3-(4-amino-4-oxobutyl)phenyl]-2-[(4-methoxy-2,5-dimethylbenzyl)amino]ethyl]-5-methyl-1,2-oxazole-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00015
N-[1-[4-(3-hydroxyprop-1-yn-1-yl)phenyl]-2-[(4-methoxy-2,5-dimethylbenzyl)amino]ethyl]-5-methyl-1,2-oxazole-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00015
N-[1-[4-(4-amino-4-oxobutyl)phenyl]-2-[(4-methoxy-2,5-dimethylbenzyl)amino]ethyl]-5-methyl-1,2-oxazole-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00012
N-[2-[(4-butoxy-2,5-dimethylbenzyl)amino]-1-phenylethyl]-5-methyl-1,2-oxazole-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00026
N-[2-[(4-ethoxy-2,5-dimethylbenzyl)amino]-1-phenylethyl]-5-methyl-1,2-oxazole-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.05
N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-(2-methoxyphenyl)ethyl]-5-methyl-1,2-oxazole-3-carboxamide
Homo sapiens
-
IC50 above 0.05 mM, pH and temperature not specified in the publication
0.0073
N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-(3-methoxyphenyl)ethyl]-5-methyl-1,2-oxazole-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.005
N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-(4-methoxyphenyl)ethyl]-5-methyl-1,2-oxazole-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.0064
N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-phenylethyl]-1,2-oxazole-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.0038
N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-phenylethyl]-3-methyl-1,2-oxazole-5-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.001
N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-phenylethyl]-5-methyl-1,2-oxazole-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.00085
N-[2-[(4-methoxy-2,5-dimethylbenzyl)amino]-1-[4-(pyridin-4-yl)phenyl]ethyl]-5-methyl-1,2-oxazole-3-carboxamide
Homo sapiens
-
pH and temperature not specified in the publication
0.05
N-[2-[(4-methoxybenzyl)amino]-1-phenylethyl]-5-methyl-1,2-oxazole-3-carboxamide
Homo sapiens
-
IC50 above 0.05 mM, pH and temperature not specified in the publication
0.0811
phosphopyridoxyl sphinganine 1-phosphate
Homo sapiens
-
at pH 10.6 and 37°C
0.089
phosphopyridoxyl sphingosine 1-phosphate
Homo sapiens
-
at pH 10.6 and 37°C
SPECIFIC ACTIVITY [µmol/min/mg]
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
additional information
-
overview
TEMPERATURE OPTIMUM
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
37
assay at
ORGANISM
COMMENTARY hide
LITERATURE
UNIPROT
SEQUENCE DB
SOURCE
SOURCE TISSUE
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
SOURCE
-
the cells expressing sphingosine-1-phosphate lyase in the parenchyma o lymph nodes are CD68+ antigen-presenting cells. CD68+ antigen-presenting cells generated from human monocytes are able to internalize and irreversibly degrade sphingosine 1-phosphate
Manually annotated by BRENDA team
-
CCL2 (ATCC)
Manually annotated by BRENDA team
-
HB 8065 (ATTC)
Manually annotated by BRENDA team
-
inhibition of sphingosine-1-phosphate lyase activity rendes sphingosine 1-phosphate an efficient S1P1 receptor internalizing compound and abrogated sphingosine-1-phosphate-mediated sustained signaling, suggesting that sphingosine-1-phosphate lyase by facilitating S1P1 receptor recycling is essential for sphingosine-1-phosphate-mediated sustained signaling, and that synthetic agonists are functional antagonists because they are not sphingosine-1-phosphate lyase substrates
Manually annotated by BRENDA team
-
silencing of sphingosine 1-phosphate lyase enhances survival after irradiation or chemotherapy by decreasing expression of proteins involved in sensing and repairing DNA damage or apoptosis, respectively. Enforced expression of sphingosine 1-phosphate lyase sensitizes cancer cells to irradiation or docetaxel by tilting the ceramide/sphingosine 1-phosphate balance toward cell death
Manually annotated by BRENDA team
-
sphingosine-1-phosphate lyase expression is almost exclusively restricted to cells on the parenchymal side of marginal reticular cells, consistent with a role in maintaining the S1P gradient between the sinuses and the parenchyma
Manually annotated by BRENDA team
-
silencing of sphingosine 1-phosphate lyase enhances survival after irradiation or chemotherapy by decreasing expression of proteins involved in sensing and repairing DNA damage or apoptosis, respectively. Enforced expression of sphingosine 1-phosphate lyase sensitizes cancer cells to irradiation or docetaxel by tilting the ceramide/sphingosine 1-phosphate balance toward cell death
Manually annotated by BRENDA team
-
in fresh human prostatectomy specimens, a remarkable decrease in sphingosine 1-phosphate lyase enzymatic activity is found in tumor samples, as compared with normal adjacent tissues. A significant relationship between loss of sphingosine 1-phosphate lyase expression and higher Gleason score is confirmed. Sphingosine 1-phosphate lyase protein expression and activity are inversely correlated with those of sphingosine kinase-1, the enzyme producing sphingosine 1-phosphate. Sphingosine 1-phosphate lyase and sphingosine kinase expressions are independently predictive of aggressive cancer on tissue microarray
Manually annotated by BRENDA team
additional information
-
the human SGPL1 gene is ubiquitously expressed with the exception of erythrocytes and platelets and its expression is linked to tissues undergoing rapid cell turnover
Manually annotated by BRENDA team
LOCALIZATION
ORGANISM
UNIPROT
COMMENTARY hide
GeneOntology No.
LITERATURE
SOURCE
GENERAL INFORMATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
metabolism
sphingosine-1-phosphate lyase is a key enzyme of sphingolipid metabolism
malfunction
-
inhibition of S1PL with 4-deoxypyridoxine or knockdown of S1PL with siRNA increases intracellular sphingosine-1-phosphate 3fold, potentiates motility of HPAEC cells to extracellular sphingosine-1-phosphate or serum, and augments activated Rac1 as well as stimulates Rac1 and IQGAP1 translocation to the cell periphery
metabolism
-
SPL functions as the exit gate of the sphingolipid metabolism
physiological function
UNIPROT
ENTRY NAME
ORGANISM
NO. OF AA
NO. OF TRANSM. HELICES
MOLECULAR WEIGHT[Da]
SOURCE
SEQUENCE
LOCALIZATION PREDICTION?
SGPL1_HUMAN
568
0
63524
Swiss-Prot
Secretory Pathway (Reliability: 4)
PDB
SCOP
CATH
UNIPROT
ORGANISM
MOLECULAR WEIGHT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
63480
calculated from amino acid sequence
63490
calculated from amino acid sequence
61000 - 65000
-
SDS-PAGE
63000
-
x * 63000, SDS-PAGE
63500
SUBUNIT
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
dimer
x-ray crystallography
homodimer
-
tetramer or hexamer
-
-
POSTTRANSLATIONAL MODIFICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
glycoprotein
-
-
CRYSTALLIZATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
in complex with (R)-6-(4-(4-benzyl-7-chlorophthalazin-1-yl)-2-methylpiperazin-1-yl)nicotinonitrile, hanging drop vapor diffusion method
PROTEIN VARIANTS
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
C218G
reduced enzyme activity
C317S
reduced enzyme activity
PURIFICATION (Commentary)
ORGANISM
UNIPROT
LITERATURE
Ni-NTA column chromatography and Superdex 200 gel filtration
CLONED (Commentary)
ORGANISM
UNIPROT
LITERATURE
expressed in Sf9 insect cells
fusion protein with green fluorescence protein, expressed in HEK293 cells
expression in HEK-293 cell
-
expression in Mus musculus
-
EXPRESSION
ORGANISM
UNIPROT
LITERATURE
enzyme expression is increased in brains of patients with Alzheimer's disease
-
high SPL transcription of H1155 cells is regulated by specificity protein 1 and GATA-4 protein/specificity protein 1 complex formation
-
mRNA expression for both sphingosine kinase and sphingosine 1-phosphate lyase are up-regulated throughout all four stages in human breast cancer patients. Exogenous administration of S1P produces a bell-shaped dose response for apoptosis in normal mammary gland MCF12A cells but a sigmoid-shaped apoptotic response in breast cancer MCF7 cells. Co-administration of S1P enhances the cytotoxicity of anticancer drug docetaxel against MCF7 cells
-
SGPL1 gene expression is downregulated in colon cancer and is upregulated in certain malignant tissues, for example, in ovarian cancers as well as in the skin of patients suffering from atopic dermatitis
-
APPLICATION
ORGANISM
UNIPROT
COMMENTARY hide
LITERATURE
analysis
medicine
REF.
AUTHORS
TITLE
JOURNAL
VOL.
PAGES
YEAR
ORGANISM (UNIPROT)
PUBMED ID
SOURCE
Van Veldhoven, P.P.
Sphingosine-phosphate lyase
Adv. Lipid Res.
26
69-98
1993
Canis lupus familiaris, Cavia porcellus, Homo sapiens, Platyrrhini, Mus musculus, Rattus norvegicus, Sus scrofa, Tetrahymena pyriformis
Manually annotated by BRENDA team
Van Veldhoven, P.P.; Mannaerts, G.P.
Sphinganine 1-phosphate metabolism in cultured skin fibroblasts: evidence for the existence of a sphingosine phosphatase
Biochem. J.
299
597-601
1994
Canis lupus familiaris, Homo sapiens
Manually annotated by BRENDA team
Van Veldhoven, P.P.; Gijsbers, S.; Mannaerts, G.P.; Vermeesch, J.R.; Brys, V.
Human sphingosine-1-phosphate lyase: cDNA cloning, functional expression studies and mapping to chromosome 10q221
Biochim. Biophys. Acta
1487
128-134
2000
Homo sapiens (O95470), Homo sapiens
Manually annotated by BRENDA team
Reiss, U.; Oskouian, B.; Zhou, J.; Gupta, V.; Sooriyakumaran, P.; Kelly, S.; Wang, E.; Merrill, A.H., Jr.; Saba, J.D.
Sphingosine-phosphate lyase enhances stress-induced ceramide generation and apoptosis
J. Biol. Chem.
279
1281-1290
2004
Homo sapiens (O95470), Homo sapiens
Manually annotated by BRENDA team
Van Veldhoven, P.P.
Sphingosine-1-phosphate lyase
Methods Enzymol.
311
244-254
2000
Homo sapiens, Mammalia, Mus musculus, Rattus norvegicus, Tetrahymena pyriformis
Manually annotated by BRENDA team
Bandhuvula, P.; Tam, Y.Y.; Oskouian, B.; Saba, J.D.
The immune modulator FTY720 inhibits sphingosine-1-phosphate lyase activity
J. Biol. Chem.
280
33697-33700
2005
Homo sapiens, Mus musculus
Manually annotated by BRENDA team
Min, J.; Van Veldhoven, P.P.; Zhang, L.; Hanigan, M.H.; Alexander, H.; Alexander, S.
Sphingosine-1-phosphate lyase regulates sensitivity of human cells to select chemotherapy drugs in a p38-dependent manner
Mol. Cancer Res.
3
287-296
2005
Homo sapiens
Manually annotated by BRENDA team
Peest, U.; Sensken, S.C.; Andreani, P.; Haenel, P.; Van Veldhoven, P.P.; Graeler, M.H.
S1P-lyase independent clearance of extracellular sphingosine 1-phosphate after dephosphorylation and cellular uptake
J. Cell. Biochem.
104
756-772
2008
Homo sapiens
Manually annotated by BRENDA team
Bandhuvula, P.; Fyrst, H.; Saba, J.D.
A rapid fluorescence assay for sphingosine-1-phosphate lyase enzyme activity
J. Lipid Res.
48
2769-2778
2007
Homo sapiens, Mus musculus
Manually annotated by BRENDA team
Oskouian, B.; Sooriyakumaran, P.; Borowsky, A.D.; Crans, A.; Dillard-Telm, L.; Tam, Y.Y.; Bandhuvula, P.; Saba, J.D.
Sphingosine-1-phosphate lyase potentiates apoptosis via p53- and p38-dependent pathways and is down-regulated in colon cancer
Proc. Natl. Acad. Sci. USA
103
17384-17389
2006
Homo sapiens, Mus musculus
Manually annotated by BRENDA team
Bandhuvula, P.; Saba, J.D.
Sphingosine-1-phosphate lyase in immunity and cancer: silencing the siren
Trends Mol. Med.
13
210-217
2007
Caenorhabditis elegans, Dictyostelium discoideum, Drosophila melanogaster, Homo sapiens, Leishmania major, Mus musculus, Rattus norvegicus
Manually annotated by BRENDA team
Bandhuvula, P.; Li, Z.; Bittman, R.; Saba, J.D.
Sphingosine 1-phosphate lyase enzyme assay using a BODIPY-labeled substrate
Biochem. Biophys. Res. Commun.
380
366-370
2009
Homo sapiens
Manually annotated by BRENDA team
Ling, B.; Chen, L.; Alcorn, J.; Ma, B.; Yang, J.
Sphingosine-1-phosphate: a potential therapeutic agent against human breast cancer
Invest. New Drugs
29
396-399
2009
Homo sapiens
Manually annotated by BRENDA team
Vogel, P.; Donoviel, M.S.; Read, R.; Hansen, G.M.; Hazlewood, J.; Anderson, S.J.; Sun, W.; Swaffield, J.; Oravecz, T.
Incomplete inhibition of sphingosine 1-phosphate lyase modulates immune system function yet prevents early lethality and non-lymphoid lesions
PLoS ONE
4
e4112
2009
Homo sapiens, Mus musculus (Q8R0X7), Mus musculus
Manually annotated by BRENDA team
Serra, M.; Saba, J.
Sphingosine 1-phosphate lyase, a key regulator of sphingosine 1-phosphate signaling and function
Adv. Enzyme Regul.
50
349-362
2010
Homo sapiens, Rattus norvegicus, Mus musculus (Q8R0X7)
Manually annotated by BRENDA team
Ito, H.; Yoshida, K.; Murakami, M.; Hagiwara, K.; Sasaki, N.; Kobayashi, M.; Takagi, A.; Kojima, T.; Sobue, S.; Suzuki, M.; Tamiya-Koizumi, K.; Nakamura, M.; Banno, Y.; Nozawa, Y.; Murate, T.
Heterogeneous sphingosine-1-phosphate lyase gene expression and its regulatory mechanism in human lung cancer cell lines
Biochim. Biophys. Acta
1811
119-128
2011
Homo sapiens
Manually annotated by BRENDA team
Berdyshev, E.V.; Gorshkova, I.; Usatyuk, P.; Kalari, S.; Zhao, Y.; Pyne, N.J.; Pyne, S.; Sabbadini, R.A.; Garcia, J.G.; Natarajan, V.
Intracellular S1P generation is essential for S1P-induced motility of human lung endothelial cells: role of sphingosine kinase 1 and S1P lyase
PLoS ONE
6
e16571
2011
Homo sapiens
Manually annotated by BRENDA team
Bourquin, F.; Capitani, G.; Gruetter, M.G.
PLP-dependent enzymes as entry and exit gates of sphingolipid metabolism
Protein Sci.
20
1492-1508
2011
Saccharomyces cerevisiae, Homo sapiens, Myxococcus xanthus, Symbiobacterium thermophilum
Manually annotated by BRENDA team
Bourquin, F.; Riezman, H.; Capitani, G.; Gruetter, M.G.
Structure and function of sphingosine-1-phosphate lyase, a key enzyme of sphingolipid metabolism
Structure
18
1054-1065
2010
Saccharomyces cerevisiae, Homo sapiens (O95470), Homo sapiens, Symbiobacterium thermophilum (Q67PY4), Symbiobacterium thermophilum
Manually annotated by BRENDA team
Billich, A.; Beerli, C.; Bergmann, R.; Bruns, C.; Loetscher, E.
Cellular assay for the characterization of sphingosine-1-phosphate lyase inhibitors
Anal. Biochem.
434
247-253
2013
Homo sapiens
Manually annotated by BRENDA team
Gatfield, J.; Monnier, L.; Studer, R.; Bolli, M.H.; Steiner, B.; Nayler, O.
Sphingosine-1-phosphate (S1P) displays sustained S1P1 receptor agonism and signaling through S1P lyase-dependent receptor recycling
Cell. Signal.
26
1576-1588
2014
Homo sapiens
Manually annotated by BRENDA team
Park, S.M.; Angel, C.E.; McIntosh, J.D.; Brooks, A.E.; Middleditch, M.; Chen, C.J.; Ruggiero, K.; Cebon, J.; Dunbar, P.R.
Sphingosine-1-phosphate lyase is expressed by CD68(+) cells on the parenchymal side of marginal reticular cells in human lymph nodes
Eur. J. Immunol.
44
2425-2436
2014
Homo sapiens
Manually annotated by BRENDA team
Brizuela, L.; Ader, I.; Mazerolles, C.; Bocquet, M.; Malavaud, B.; Cuvillier, O.
First evidence of sphingosine 1-phosphate lyase protein expression and activity downregulation in human neoplasm: implication for resistance to therapeutics in prostate cancer
Mol. Cancer Ther.
11
1841-1851
2012
Homo sapiens
Manually annotated by BRENDA team
Ceccom, J.; Loukh, N.; Lauwers-Cances, V.; Touriol, C.; Nicaise, Y.; Gentil, C.; Uro-Coste, E.; Pitson, S.; Maurage, C.A.; Duyckaerts, C.; Cuvillier, O.; Delisle, M.B.
Reduced sphingosine kinase-1 and enhanced sphingosine 1-phosphate lyase expression demonstrate deregulated sphingosine 1-phosphate signaling in Alzheimers disease
Acta Neuropathol. Commun.
2
12
2014
Homo sapiens
Manually annotated by BRENDA team
Dinges, J.; Harris, C.M.; Wallace, G.A.; Argiriadi, M.A.; Queeney, K.L.; Perron, D.C.; Dominguez, E.; Kebede, T.; Desino, K.E.; Patel, H.; Vasudevan, A.
Hit-to-lead evaluation of a novel class of sphingosine 1-phosphate lyase inhibitors
Bioorg. Med. Chem. Lett.
26
2297-2302
2016
Homo sapiens
Manually annotated by BRENDA team
Sanllehi, P.; Casasampere, M.; Abad, J.L.; Fabrias, G.; Lopez, O.; Bujons, J.; Casas, J.; Delgado, A.
The first fluorogenic sensor for sphingosine-1-phosphate lyase activity in intact cells
Chem. Commun. (Camb.)
53
5441-5444
2017
Homo sapiens (O95470)
Manually annotated by BRENDA team
Suh, J.H.; Eltanawy, A.; Rangan, A.; Saba, J.D.
A facile stable-isotope dilution method for determination of sphingosine phosphate lyase activity
Chem. Phys. Lipids
194
101-109
2016
Homo sapiens, Mus musculus
Manually annotated by BRENDA team
Sanllehi, P.; Abad, J.L.; Casas, J.; Delgado, A.
Inhibitors of sphingosine-1-phosphate metabolism (sphingosine kinases and sphingosine-1-phosphate lyase)
Chem. Phys. Lipids
197
69-81
2016
Homo sapiens
Manually annotated by BRENDA team
Sanllehi, P.; Abad, J.L.; Bujons, J.; Casas, J.; Delgado, A.
Studies on the inhibition of sphingosine-1-phosphate lyase by stabilized reaction intermediates and stereodefined azido phosphates
Eur. J. Med. Chem.
123
905-915
2016
Homo sapiens, Symbiobacterium thermophilum
Manually annotated by BRENDA team
Weiler, S.; Braendlin, N.; Beerli, C.; Bergsdorf, C.; Schubart, A.; Srinivas, H.; Oberhauser, B.; Billich, A.
Orally active 7-substituted [(4-benzylphthalazin-1-yl)-2-methylpiperazin-1-yl]nicotinonitriles as active-site inhibitors of sphingosine 1-phosphate lyase for the treatment of multiple sclerosis
J. Med. Chem.
57
5074-5084
2014
Homo sapiens (O95470), Homo sapiens
Manually annotated by BRENDA team