D-glucosyl-ß1-1'-D-erythro-sphingosine - ≥95% , CAS No.52050-17-6

CAS: 52050-17-6 Cat. No.: D130636 Molecular Weight: 461.632

GRADE & PURITY ≥95%

Synonyms

Lyso GlcCer | (2R,3R,4S,5S,6R)-2-[(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol | glucosylsphingosine | beta-D-Glucopyranoside, (2S,3R,4E)-2-amino-3-hydroxy-4-octadecen-1-yl | DTXSID101315465 | MS-28477 | (2S,3R,4E)-2-amin

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

Specifications

Synonyms

Lyso GlcCer | (2R, 3R, 4S, 5S, 6R)-2-[(E, 2S, 3R)-2-amino-3-hydroxyoctadec-4-enoxy]-6-(hydroxymethyl)oxane-3, 4, 5-triol | glucosylsphingosine | beta-D-Glucopyranoside, (2S, 3R, 4E)-2-amino-3-hydroxy-4-octadecen-1-yl | DTXSID101315465 | MS-28477 | (2S, 3R, 4E)-2-amin

Specifications & Purity

≥95%

Biochemical and Physiological Mechanisms

Glucocerebroside derivative. Biomarker for selective β-glucocerebrosidase deficiency. Increases intracellular Ca 2+ levels. Induces calpain-mediated apoptosis. Shows selective cytotoxicity to cancer cells.

Storage

Store at -20°C

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

INHIBITOR

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥95%

Names and Identifiers

• Pubchem Sid: 488195212
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/488195212
• Canonical Smiles: CCCCCCCCCCCCCC=CC(C(COC1C(C(C(C(O1)CO)O)O)O)N)O
• IUPAC Name: (2R,3R,4S,5S,6R)-2-[(E,2S,3R)-2-amino-3-hydroxyoctadec-4-enoxy]-6-(hydroxymethyl)oxane-3,4,5-triol
• InChIKey: HHJTWTPUPVQKNA-JIAPQYILSA-N
• INCHI: 1S/C24H47NO7/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-19(27)18(25)17-31-24-23(30)22(29)21(28)20(16-26)32-24/h14-15,18-24,26-30H,2-13,16-17,25H2,1H3/b15-14+/t18-,19+,20+,21+,22-,23+,24+/m0/s1
• Isomeric SMILES: CCCCCCCCCCCCC/C=C/[C@H]([C@H](CO[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)O)O)N)O
• Molecular Weight: 461.632
• Reaxy-Rn: 39165941
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=39165941&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Lipids and lipid-like molecules
    • Class Sphingolipids
      • Subclass Glycosphingolipids

• Kingdom: Organic compounds
• Superclass: Lipids and lipid-like molecules
• Class: Sphingolipids
• Subclass: Glycosphingolipids
• Intermediate Tree Nodes: Not available
• Direct Parent: Glycosphingolipids
• Alternative Parents: Fatty acyl glycosides of mono- and disaccharides Hexoses Alkyl glycosides O-glycosyl compounds Oxanes Secondary alcohols Polyols Oxacyclic compounds Acetals Primary alcohols Organopnictogen compounds Monoalkylamines Hydrocarbon derivatives
• Molecular Framework: Aliphatic heteromonocyclic compounds
• Substituents: Glycosphingolipid - Fatty acyl glycoside - Fatty acyl glycoside of mono- or disaccharide - Alkyl glycoside - Hexose monosaccharide - Glycosyl compound - O-glycosyl compound - Fatty acyl - Oxane - Monosaccharide - Secondary alcohol - Oxacycle - Organoheterocyclic compound - Acetal - Polyol - Organic oxygen compound - Organonitrogen compound - Organooxygen compound - Primary aliphatic amine - Primary alcohol - Primary amine - Alcohol - Organic nitrogen compound - Amine - Hydrocarbon derivative - Organopnictogen compound - Aliphatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as glycosphingolipids. These are sphingolipids containing a saccharide moiety glycosidically attached to the sphingoid base. Although saccharide moieties are mostly O-glycosidically linked to the ceramide moiety, other sphingolipids with glycosidic bonds of other types (e.g. S-,C-, or N-type) has been reported.
• External Descriptors: beta-D-glucoside - D-glucosylsphingosine

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Molecular Weight: 461.600 g/mol
• XLogP3: 3.700
• Hydrogen Bond Donor Count: 6
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 18
• Exact Mass: 461.335 Da
• Monoisotopic Mass: 461.335 Da
• Topological Polar Surface Area: 146.000 Ų
• Heavy Atom Count: 32
• Formal Charge: 0
• Complexity: 479.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 7
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 1
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 1
• Covalently-Bonded Unit Count: 1

References

1. Shi-En Chen, Shuyun Zhu, Jingwen Hu, Jing Sun, Zhenjia Zheng, Xian-En Zhao, Huwei Liu.  (2020)  8-Plex stable isotope labeling absolute quantitation strategy combined with dual-targeted recognizing function material for simultaneous separation and determination of glucosylsphingosine and galactosylsphingosine in human plasma.  ANALYTICA CHIMICA ACTA,      [PMID:32534674] [10.1016/j.aca.2020.05.032]