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Ganglioside GM3

CAT: 0804-HY-114456-01Size: 1 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-114456-01Size:1 mg
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Description
Ganglioside GM3 is a precursor of a-, b-, and c-series gangliosides, interacts with transmembrane receptors such as the epidermal growth factor and insulin receptors, and regulates receptor functions by creating a specialized lipid environment. Ganglioside GM3 is synthesized by GM3 synthase and can be used for the research of hypercholesterolemia[1].
CAS Number
124579-05-1
Product Name Alternative
D-APV; D-2-Amino-5-phosphonovaleric acid
UNSPSC
12352005
Target
Insulin Receptor
Type
Reference compound
Related Pathways
Protein Tyrosine Kinase/RTK
Applications
Metabolism-sugar/lipid metabolism
Field of Research
Metabolic Disease
Assay Protocol
https://www.medchemexpress.com/ganglioside-gm3.html
Purity
99.42
Solubility
DMSO : 125 mg/mL (ultrasonic)
Smiles
OC([C@@]1(O[C@@]([C@H](NC(C)=O)[C@@H](O)C1)([H])[C@H](O)[C@H](O)CO)O[C@@H]2[C@H]([C@@H](O[C@H](CO)[C@@H]2O)O[C@]3([H])[C@H](O[C@@H](OC[C@@H]([C@H](O)/C=C/CCCCCCCCCCCCC)NC(CCCCCCCCCCCCCCCCC)=O)[C@H](O)[C@H]3O)CO)O)=O
Molecular Formula
C59H108N2O21
Molecular Weight
1181.49
References & Citations
[1]Nihei W, et al. NPC1L1-dependent intestinal cholesterol absorption requires ganglioside GM3 in membrane microdomains. J Lipid Res. 2018 Nov;59 (11) :2181-2187.|[2]Inokuchi JI, et al. Pathophysiological Significance of GM3 Ganglioside Molecular Species With a Particular Attention to the Metabolic Syndrome Focusing on Toll-Like Receptor 4 Binding. Front Mol Biosci. 2022 May 30;9:918346.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

GM3(d18:1/18:0)

Alpha-Neu5Ac-(2->3)-beta-D-Gal-(1->4)-beta-D-Glc-(1<->1')-Cer(d18:1/18:0) is a sialotriaosylceramide consisting of beta-D-GalNAc-(14)-[alpha-Neu5Ac-(23)]-beta-D-Gal-(14)-beta-D-Glc attached to the primary hydroxy function of ceramide(d18:1/18:0). It has a role as a mouse metabolite. It is functionally related to an octadecanoic acid. It is a conjugate acid of an alpha-Neu5Ac-(2->3)-beta-Gal-(1->4)-beta-Glc-(1<->1')-Cer(d18:1/18:0)(1-).

CAS Number124579-05-1
PubChem CID9812294
IUPAC Name(2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(E,2S,3R)-3-hydroxy-2-(octadecanoylamino)octadec-4-enoxy]oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxane-2-carboxylic acid
Molecular FormulaC59H108N2O21
Molecular Weight1181.5
XLogP7.7
Topological Polar Surface Area373
Hydrogen Bond Donor Count14
Hydrogen Bond Acceptor Count21
Rotatable Bond Count45
Heavy Atom Count82
Formal Charge0
Complexity1740
SMILES
CCCCCCCCCCCCCCCCCC(=O)N[C@@H](CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O[C@H]2[C@@H]([C@H]([C@H]([C@H](O2)CO)O)O[C@@]3(C[C@@H]([C@H]([C@@H](O3)[C@@H]([C@@H](CO)O)O)NC(=O)C)O)C(=O)O)O)O)O)[C@@H](/C=C/CCCCCCCCCCCCC)O
InChI
InChI=1S/C59H108N2O21/c1-4-6-8-10-12-14-16-18-19-21-23-25-27-29-31-33-46(69)61-40(41(66)32-30-28-26-24-22-20-17-15-13-11-9-7-5-2)38-77-56-51(73)50(72)53(45(37-64)79-56)80-57-52(74)55(49(71)44(36-63)78-57)82-59(58(75)76)34-42(67)47(60-39(3)65)54(81-59)48(70)43(68)35-62/h30,32,40-45,47-57,62-64,66-68,70-74H,4-29,31,33-38H2,1-3H3,(H,60,65)(H,61,69)(H,75,76)/b32-30+/t40-,41+,42-,43+,44+,45+,47+,48+,49-,50+,51+,52+,53+,54+,55-,56+,57-,59-/m0/s1
InChIKey
UIKPUUZBQYTDRX-YRRBDHRDSA-N
Chemical Structure
2D Structure
2D structure of GM3(d18:1/18:0)
CAS: 124579-05-1
CID: 9812294
Formula: C59H108N2O21
MW: 1181.5
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1181.5
XLogP37.7
Hydrogen Bond Donor Count14
Hydrogen Bond Acceptor Count21
Rotatable Bond Count45
Exact Mass1180.74445846
Monoisotopic Mass1180.74445846
Topological Polar Surface Area373 Ų
Heavy Atom Count82
Formal Charge0
Complexity1740
Isotope Atom Count0
Defined Atom Stereocenter Count18
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count1
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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CatalogName
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KQD67078Ngcgm3 ganglioside
OG175967-01GD1a-Ganglioside
OG16402-01GA2-Ganglioside
297083GM4-Ganglioside
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GC4593-5mgGT1b-Ganglioside

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