Ligand N-acetylneuraminate

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Basic Ligand Information

Molecular Structure
Picture of N-acetylneuraminate (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C11H19NO9
N-acetylneuraminate
SQVRNKJHWKZAKO-PFQGKNLYSA-N
Synonyms:
5-N-acetylneuraminic acid, acetylneuramicnate, beta-sialic acid, N-acetyl-beta-neuraminate, N-acetyl-D-neuraminic acid, N-acetyl-neuraminate, N-acetyl-neuraminic acid, N-acetylneuraminic acid, N-acetyl neuraminic acid, Neu5Ac, NeuAc, sialic acid


Show all pahtways known for Show all BRENDA pathways known for N-acetylneuraminate

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (17 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
S-adenosyl-L-methionine + N-acetylneuraminic acid = S-adenosyl-L-homocysteine + N-acetyl-8-O-methyl-neuraminate
show the reaction diagram
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acetyl-CoA + N-acetylneuraminate = CoA + N-acetyl-4-O-acetylneuraminate
show the reaction diagram
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CTP + sialic acid = CMP-sialic acid + diphosphate
show the reaction diagram
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CTP + N-acetylneuraminic acid = diphosphate + CMP-N-acetylneuraminic acid
show the reaction diagram
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sialic acid + H2O = ?
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (48 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
N-acetylneuraminate 9-phosphate + H2O = N-acetylneuraminate + phosphate
show the reaction diagram
-
-
N-acetyl-D-mannosamine + pyruvate = N-acetylneuraminate
show the reaction diagram
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-
N-acetyl-alpha-neuraminate = N-acetyl-beta-neuraminate
show the reaction diagram
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-

Substrate in Enzyme-catalyzed Reactions (39 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
N-acetylneuraminate + oxidized 1,1'-carbamoyl methyl viologen = ? + reduced 1,1'-carbamoyl methyl viologen
show the reaction diagram
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N-acetylneuraminate + acceptor = ?
show the reaction diagram
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S-adenosyl-L-methionine + N-acetylneuraminic acid = S-adenosyl-L-homocysteine + N-acetyl-8-O-methyl-neuraminate
show the reaction diagram
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acetyl-CoA + Neu5Ac = CoA + O-(acetyl)-Neu5Ac
show the reaction diagram
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acetyl-CoA + N-acetylneuraminate = CoA + N-acetyl-4-O-acetylneuraminate
show the reaction diagram
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CMP-N-acetylneuraminate + beta-sialic acid = CMP + alpha-N-acetylneuraminyl-(2->8)-beta-N-acetylneuraminate
show the reaction diagram
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CTP + N-acetylneuraminic acid = diphosphate + CMP-N-acetylneuraminic acid
show the reaction diagram
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sialic acid + H2O = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (319 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
9-O-acetyl sialic acid + H2O = sialic acid + acetate
show the reaction diagram
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N-acetylneuraminic acid 9-phosphate + H2O = N-acetylneuraminic acid + phosphate
show the reaction diagram
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N-acetylneuraminate 9-phosphate + H2O = N-acetylneuraminate + phosphate
show the reaction diagram
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N-acetyl-alpha-neuraminate = N-acetyl-beta-neuraminate
show the reaction diagram
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Activator in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE

Inhibitor in Enzyme-catalyzed Reactions (19 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
with or without tetrahexosylceramide
-
plasmalogen-specific PLA2
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both binding and permeation of toxins are potently inhibited by N-acetyl neuraminic acid in the cell culture mediumor by treatment of the cells with neuraminidase, but neither galactose, lactose nor N-acetyl galactosamine inhibit binding or permeation of toxins

3D Structure of Enzyme-Ligand-Complex (PDB) (16 results)

Enzyme Kinetic Parameters

kcat Value (Turnover Number) (66 results)

EC NUMBER
TURNOVER NUMBER [1/S]
TURNOVER NUMBER MAXIMUM [1/S]
COMMENTARY
LITERATURE
329.6
-
at pH 6.5 and 50°C

KM Value (132 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.299
-
pH 8.0, 25°C
0.75
-
at pH 6.5 and 50°C

Ki Value (8 results)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE

IC50 Value (7 results)

EC NUMBER
IC50 VALUE
IC50 VALUE MAXIMUM
COMMENTARY
LITERATURE
15
-
in 25 mM HEPES, pH 7.4, 25 mM KCl, 1 mM MgCl2, 1 mM dithiothreitol, at 37°C
0.6
-
-

References & Links

Links to other databases for N-acetylneuraminate

ChEBI
PubChem
ChEBI
PubChem