Ligand ganglioside GM3

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Basic Ligand Information

Molecular Structure
Picture of ganglioside GM3 (click for magnification)
Molecular Formula
BRENDA Name
InChIKey
C59H108N2O21
ganglioside GM3
UIKPUUZBQYTDRX-YRRBDHRDSA-N
Synonyms:
(N-acetylneuraminyl)-D-galactosyl-D-glucosylceramide, 1-O-[O-(N-acetyl-alpha-neuraminosyl)-(2-3)-O-beta-D-galactopyranosyl-(1-4)-beta-D-glucopyranosyl]-ceramide, 1-O-[O-(N-acetyl-alpha-neuraminosyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranosyl]-ceramide, 1-O-[O-(N-acetyl-alpha-neuraminyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranosyl]-ceramide, alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide, alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-beta-D-glucosyl-ceramide, alpha-N-acetylneuraminyl-2,3-beta-D-galactosyl-1,4-beta-D-glucosylceramide, ganglioside M3, GM3, GM3(N-acetylneuraminic acid), hematoside, N-acetylneuraminyl-(2->3)-alpha-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide, N-acetylneuraminyl-2,3-alpha-D-galactosyl-1,4-beta-D-glucosylceramide, O-(N-acetyl-alpha-neuraminyl)-(2->3)-O-beta-D-galactopyranosyl-(1->4)-beta-D-glucopyranosyl-(1<->1)-ceramide
Pathway Source
Pathways

Roles as Enzyme Ligand

In Vivo Substrate in Enzyme-catalyzed Reactions (9 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
UDP-N-acetyl-D-galactosamine + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide = UDP + N-acetyl-beta-D-galactosaminyl-(1->4)-[alpha-N-acetylneuraminyl-(2->3)]-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide
show the reaction diagram
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In Vivo Product in Enzyme-catalyzed Reactions (4 results)

EC NUMBER
PROVEN IN VIVO REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ganglioside GM2 + H2O = ganglioside GM3 + N-acetyl-beta-D-galactosamine
show the reaction diagram
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Substrate in Enzyme-catalyzed Reactions (18 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
UDP-N-acetyl-D-galactosamine + alpha-N-acetylneuraminyl-(2->3)-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide = UDP + N-acetyl-beta-D-galactosaminyl-(1->4)-[alpha-N-acetylneuraminyl-(2->3)]-beta-D-galactosyl-(1->4)-beta-D-glucosyl-(1<->1)-ceramide
show the reaction diagram
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CMP-N-acetylneuraminate + GM3 = ?
show the reaction diagram
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ganglioside GM3 + H2O = ?
show the reaction diagram
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Product in Enzyme-catalyzed Reactions (5 results)

EC NUMBER
REACTION
REACTION DIAGRAM
LITERATURE
ENZYME 3D STRUCTURE
ganglioside GD3 + H2O = N-acetylneuraminate + ganglioside GM3
show the reaction diagram
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ganglioside GM2 + H2O = ganglioside GM3 + N-acetyl-beta-D-galactosamine
show the reaction diagram
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Inhibitor in Enzyme-catalyzed Reactions (7 results)

EC NUMBER
COMMENTARY
LITERATURE
ENZYME 3D STRUCTURE
in the presence of Triton CF-54
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0.5 mM and 1 mM, 43% and 60% inhibition respectively
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plasmalogen-specific PLA2
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Enzyme Kinetic Parameters

KM Value (17 results)

EC NUMBER
KM VALUE [MM]
KM VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
1.1
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Ki Value (1 result)

EC NUMBER
KI VALUE [MM]
KI VALUE MAXIMUM [MM]
COMMENTARY
LITERATURE
0.12
-
inhibition of GD2 synthesis, pH 7.35, 37°C

References & Links

Links to other databases for ganglioside GM3

ChEBI
PubChem
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PubChem