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Ganglioside GM3

CAT: 0013-GTR19264826-01Size: 10 mgDry Ice: NoHazardous: No
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CAT#:0013-GTR19264826-01Size:10 mg
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Description
Ganglioside GM3 is a precursor of a, b, and c series gangliosides and interacts with transmembrane receptors such as epidermal growth factor and insulin receptors, modulating receptor function by creating specialized lipid environments. Synthesized by GM3 synthase, it can be used in studies related to hypercholesterolemia.
CAS Number
124579-05-1
Field of Research
Signal Transduction
Smiles
O ([C@@]1 (C (O) =O) O[C@@] ([C@@H] ([C@@H] (CO) O) O) ([C@H] (NC (C) =O) [C@@H] (O) C1) [H]) [C@@H]2[C@@H] (O) [C@H] (O[C@@H]3[C@@H] (CO) O[C@@H] (OC[C@H] (NC (CCCCCCCCCCCCCCCCC) =O) [C@@H] (/C=C/CCCCCCCCCCCCC) O) [C@H] (O) [C@H]3O) O[C@H] (CO) [C@@H]2O
Molecular Formula
C59H108N2O21
Molecular Weight
1181.49
Storage Conditions
-20°C
Notes
For research use only.

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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