Ligand sphingosine

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Basic Ligand Information

Molecular Structure
Picture of sphingosine (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C18H37NO2
sphingosine
WWUZIQQURGPMPG-KRWOKUGFSA-N
Synonyms:
4-octadecyl-sphingenine, 4-sphingenine, a sphingoid base, D-erythro-sphingosine, D-erythrosphingosine, DL-sphingosine, sphingenine


Show all pahtways known for Show all BRENDA pathways known for sphingosine

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (28 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
palmitoyl-CoA + a sphingoid base = an N-(palmitoyl)-sphingoid base + CoA
show the reaction diagram
-
CDP-choline + sphingosine = CMP + sphingosylphosphorylcholine
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (29 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
sphingomyelin + H2O = ceramide + sphingosine
show the reaction diagram
-
-
glucosyl ceramide + H2O = sphingosine + fatty acid + beta-D-glucose
show the reaction diagram
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D-galactosylsphingoside + H2O = D-galactose + sphingosine
show the reaction diagram
-
-
galactosylsphingosine + H2O = beta-D-galactose + sphingosine
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (98 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
sphingosine + reduced acceptor + H+ + O2 = phytosphingosine + acceptor + H2O
show the reaction diagram
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UDP-glucose + sphingosine = UDP + D-glucosyl-sphingosine
show the reaction diagram
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CDP-choline + sphingosine = CMP + sphingosylphosphorylcholine
show the reaction diagram
-
D-erythro-sphingosine + H2O = ?
show the reaction diagram
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D-erythro-sphingosine + a sugar = ?
show the reaction diagram
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D-erythrosphingosine = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (100 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
glucosyl ceramide + H2O = sphingosine + fatty acid + beta-D-glucose
show the reaction diagram
-

Activator in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
0.0025-0.0075 mM, activates
-
only hydrolase activity
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Inhibitor in Enzyme-catalyzed Reactions (29 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
IC50 is 9 mol%, inhibits activity in Triton X-100 mixed micelles and isolated hepatocytes
-
inhibits the 150000 Da enzyme
-
polymerase alpha and beta
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50% inhibition at 0.15 mM, kinetics, enhanced by phosphatidylcholine or sphingomyelin. Phosphatidylinositol, phosphatidylserine or oleic acid reverses
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inhibition of both isozymes, overview
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hydrolysis of lactosyl ceramide
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3D Structure of Enzyme-Ligand-Complex (PDB) (45 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (1 result)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
0.07
-
-

KM Value (33 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.04
-
-
0.04
-
-
0.2
-
-

Ki Value (2 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.006
-
pH 7.2, 37C
0.004
-
pH 8.5, recombinant CDase

IC50 Value (1 result)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
0.08
-
product inhibition in a dose-dependent manner, IC50: 0.08 mM

References & Links

Links to other databases for sphingosine

ChEBI
PubChem
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PubChem