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Lyso-Monosialoganglioside GM3

CAT: 0804-HY-171443Size: 1 EachDry Ice: NoHazardous: No
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Description
Lyso-Monosialoganglioside GM3 (Lyso-GM3) is an analogue of Ganglioside GM3 with antitumor activities. Lyso-Monosialoganglioside inhibits EGF-induced increases in EGFR kinase activity in A431 epithelial cancer cells[1].
CAS Number
94458-63-6
Product Name Alternative
Lyso-GM3
UNSPSC
12352005
Target
Drug Derivative; EGFR
Related Pathways
JAK/STAT Signaling; Others; Protein Tyrosine Kinase/RTK
Applications
Cancer-Kinase/protease
Field of Research
Cancer
Smiles
OC([C@@]1(O[C@@]([C@@H]([C@H](C1)O)NC(C)=O)([H])[C@H](O)[C@H](O)CO)O[C@@H]2[C@H]([C@@H](O[C@@H]([C@@H]2O)CO)O[C@@H]3[C@H](O[C@H]([C@@H]([C@H]3O)O)OC[C@H](N)[C@H](O)/C=C/CCCCCCCCCCCCC)CO)O)=O
Molecular Formula
C41H74N2O20
Molecular Weight
915.03
References & Citations
[1]Li T, et al. Chemoenzymatic synthesis and biological evaluation of ganglioside GM3 and lyso-GM3 as potential agents for cancer therapy. Carbohydr Res. 2021 Nov;509:108431.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

Lyso-Monosialoganglioside GM3
CAS Number94458-63-6
PubChem CID11029351
IUPAC Name(2S,4S,5R,6R)-5-acetamido-2-[(2S,3R,4S,5S,6R)-2-[(2R,3S,4R,5R,6R)-6-[(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enoxy]-4,5-dihydroxy-2-(hydroxymethyl)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 FormulaC41H74N2O20
Molecular Weight915.0
XLogP-3.2
Topological Polar Surface Area370
Hydrogen Bond Donor Count14
Hydrogen Bond Acceptor Count21
Rotatable Bond Count28
Heavy Atom Count63
Formal Charge0
Complexity1350
SMILES
CCCCCCCCCCCCC/C=C/[C@H]([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)N)O
InChI
InChI=1S/C41H74N2O20/c1-3-4-5-6-7-8-9-10-11-12-13-14-15-16-24(48)23(42)21-58-38-33(54)32(53)35(28(20-46)60-38)61-39-34(55)37(31(52)27(19-45)59-39)63-41(40(56)57)17-25(49)29(43-22(2)47)36(62-41)30(51)26(50)18-44/h15-16,23-39,44-46,48-55H,3-14,17-21,42H2,1-2H3,(H,43,47)(H,56,57)/b16-15+/t23-,24+,25-,26+,27+,28+,29+,30+,31-,32+,33+,34+,35+,36+,37-,38+,39-,41-/m0/s1
InChIKey
QLMGGRZACLACKO-PJSUIWAYSA-N
Chemical Structure
2D Structure
2D structure of Lyso-Monosialoganglioside GM3
CAS: 94458-63-6
CID: 11029351
Formula: C41H74N2O20
MW: 915.0
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight915.0
XLogP3-3.2
Hydrogen Bond Donor Count14
Hydrogen Bond Acceptor Count21
Rotatable Bond Count28
Exact Mass914.48349275
Monoisotopic Mass914.48349275
Topological Polar Surface Area370 Ų
Heavy Atom Count63
Formal Charge0
Complexity1350
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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