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RWJ 21757

CAT: 0607-B7159-50Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0607-B7159-50Size:50 mg
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Description
Toll-like receptor 7 (TLR7) agonist
CAS Number
121288-39-9
Product Name Alternative
7-allyl-2-amino-9-((2S,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-3H-purine-6,8(7H,9H)-dione
Field of Research
Immunology Inflammation TLR
Purity
0.98
Solubility
Soluble in DMSO
Smiles
O[C@H]1[C@@H](N2C(NC(N)=NC3=O)=C3N(CC=C)C2=O)O[C@H](CO)[C@H]1O
Molecular Formula
C13H17N5O6
Molecular Weight
339.3
Shipping Conditions
Blue ice
Storage Conditions
Store at -20°C.

Chemical Information

Loxoribine

Loxoribine is a guanine ribonucleotide derivative with immunostimulatory and immunomodulatory activity. Loxoribine undergoes facilitated transport across the plasma membrane into the cytoplasmic compartment of the cell and acts intracellularly, bypassing the biochemical steps involved in the membrane signal transduction pathway used by Ag or anti-IgM Abs to activate B cells. This agent activates the Toll-like receptor 7 (TLR7), a member of the TLR family of pathogen-associated molecular pattern recognition receptors thereby activating the innate immune system. This activation requires endosomal maturation and recognition is restricted to TLR7. As a result, loxoribine induces cycling B cells to proliferate and differentiate non-specifically and recruit antigen-reactive B cells to undergo differentiation to antibody production, markedly amplifying the underlying response in the process.

CAS Number121288-39-9
PubChem CID135410906
IUPAC Name2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-enyl-1H-purine-6,8-dione
Molecular FormulaC13H17N5O6
Molecular Weight339.30
XLogP-2.7
Topological Polar Surface Area161
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Heavy Atom Count24
Formal Charge0
Complexity661
SMILES
C=CCN1C2=C(N=C(NC2=O)N)N(C1=O)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O
InChI
InChI=1S/C13H17N5O6/c1-2-3-17-6-9(15-12(14)16-10(6)22)18(13(17)23)11-8(21)7(20)5(4-19)24-11/h2,5,7-8,11,19-21H,1,3-4H2,(H3,14,15,16,22)/t5-,7-,8-,11-/m1/s1
InChIKey
VDCRFBBZFHHYGT-IOSLPCCCSA-N
Chemical Structure
2D Structure
2D structure of Loxoribine
CAS: 121288-39-9
CID: 135410906
Formula: C13H17N5O6
MW: 339.30
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight339.30
XLogP3-2.7
Hydrogen Bond Donor Count5
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Exact Mass339.11788328
Monoisotopic Mass339.11788328
Topological Polar Surface Area161 Ų
Heavy Atom Count24
Formal Charge0
Complexity661
Isotope Atom Count0
Defined Atom Stereocenter Count4
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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