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GD3 Ganglioside

CAT: 0804-HY-157343-01Size: 500 µgDry Ice: NoHazardous: No
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CAT#:0804-HY-157343-01Size:500 µg
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Description
GD3 Ganglioside is a prominent ganglioside of human melanoma. GD3 Ganglioside is an inducer of mitochondrial permeability. GD3 ganglioside directly targets mitochondria in a bcl-2-controlled fashion. GD3 ganglioside is rapidly synthesized from accumulated ceramide after the clustering of death-inducing receptors and triggers apoptosis[1].
CAS Number
62010-37-1
UNSPSC
12352100
Target
Apoptosis
Type
Natural Products
Related Pathways
Apoptosis
Applications
Cancer-programmed cell death
Field of Research
Cancer; Neurological Disease
Assay Protocol
https://www.medchemexpress.com/gd3-ganglioside.html
Solubility
10 mM in DMSO
Smiles
[GD3Ganglioside]
References & Citations
[1]Rippo MR, et al. GD3 ganglioside directly targets mitochondria in a bcl-2-controlled fashion. FASEB J. 2000 Oct;14 (13) :2047-54.
Shipping Conditions
Room temperature
Scientific Category
Natural Products
Clinical Information
No Development Reported

Chemical Information

ganglioside GD3

Ganglioside GD3 is a cell surface antigen expressed on all tumors of neuroectodermal origin, including melanoma, neuroblastomas, sarcoma, astrocytomas, and small cell lung cancer. GD3, an O-acetylated disialoganglioside, belongs to the group of glycosphingolipids that are widely expressed in many tissues and organs in vertebrates and have been suggested to be involved in the regulation of development and differentiation as recognition molecules or signal modulators. GD3 and GD2 gangliosides represent distinct and relevant immunotherapeutic target structures on melanoma, thereby both have the potential to be used as components of anti-melanoma vaccines.

CAS Number62010-37-1
PubChem CID170924130
IUPAC Namedisodium;(2S,4S,5R,6R)-5-acetamido-6-[(1S,2R)-2-[(2S,4S,5R,6R)-5-acetamido-2-carboxylato-4-hydroxy-6-[(1R,2R)-1,2,3-trihydroxypropyl]oxan-2-yl]oxy-1,3-dihydroxypropyl]-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-4,5-dihydroxy-2-(hydroxymethyl)-6-[(2S,3R)-3-hydroxy-2-(octadecanoylamino)octadec-4-enoxy]oxan-3-yl]oxy-3,5-dihydroxy-6-(hydroxymethyl)oxan-4-yl]oxy-4-hydroxyoxane-2-carboxylate
Molecular FormulaC70H123N3Na2O29
Molecular Weight1516.7
Topological Polar Surface Area525
Hydrogen Bond Donor Count17
Hydrogen Bond Acceptor Count29
Rotatable Bond Count50
Heavy Atom Count104
Formal Charge0
Complexity2400
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[C@@]4(C[C@@H]([C@H]([C@@H](O4)[C@@H]([C@@H](CO)O)O)NC(=O)C)O)C(=O)[O-])O)NC(=O)C)O)C(=O)[O-])O)O)O)[C@@H](C=CCCCCCCCCCCCCC)O.[Na+].[Na+]
InChI
InChI=1S/C70H125N3O29.2Na/c1-5-7-9-11-13-15-17-19-20-22-24-26-28-30-32-34-52(84)73-44(45(80)33-31-29-27-25-23-21-18-16-14-12-10-8-6-2)41-95-65-59(89)58(88)61(51(40-77)97-65)98-66-60(90)64(56(86)49(38-75)96-66)102-70(68(93)94)36-47(82)54(72-43(4)79)63(101-70)57(87)50(39-76)99-69(67(91)92)35-46(81)53(71-42(3)78)62(100-69)55(85)48(83)37-74;;/h31,33,44-51,53-66,74-77,80-83,85-90H,5-30,32,34-41H2,1-4H3,(H,71,78)(H,72,79)(H,73,84)(H,91,92)(H,93,94);;/q;2*+1/p-2/t44-,45+,46-,47-,48+,49+,50+,51+,53+,54+,55+,56-,57+,58+,59+,60+,61+,62+,63+,64-,65+,66-,69+,70-;;/m0../s1
InChIKey
LGRBZCLULGFXOD-CIGIAFLBSA-L
Chemical Structure
2D Structure
2D structure of ganglioside GD3
CAS: 62010-37-1
CID: 170924130
Formula: C70H123N3Na2O29
MW: 1516.7
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight1516.7
Hydrogen Bond Donor Count17
Hydrogen Bond Acceptor Count29
Rotatable Bond Count50
Exact Mass1515.8037635
Monoisotopic Mass1515.8037635
Topological Polar Surface Area525 Ų
Heavy Atom Count104
Formal Charge0
Complexity2400
Isotope Atom Count0
Defined Atom Stereocenter Count24
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count1
Covalently-Bonded Unit Count3
Compound Is CanonicalizedYes

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