| Synonyms |
7,8-Dihydro-8-oxo-7-allyl-guanosine; RWJ-21757; RWJ 21757; RWJ21757; 7-Allyl-8-oxoguanosine; Loxoribina; 7-Allyl-7,8-dihydro-8-oxoguanosine; 7-Allyl-2-amino-9-beta-D-ribofuranosylpurine-6,8(1H,9H)-dione |
| IUPAC Name |
2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-7-prop-2-enyl-1H-purine-6,8-dione |
| Molecular Weight |
339.30 |
| Molecular Formula |
C13H17N5O6 |
| Canonical SMILES |
C=CCN1C2=C(NC(=NC2=O)N)N(C1=O)C3C(C(C(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 |
| Boiling Point |
591.75°C at 760 mmHg |
| Melting Point |
227-230°C |
| Flash Point |
311.7°C |
| Purity |
≥95% |
| Density |
1.92±0.1 g/cm3 (Predicted) |
| Solubility |
Soluble in DMSO (30mg/ml), water (10mg/ml), water:acetonitrile (1:1) (20mg/ml) or water:methanol (1:1) (10mg/ml). |
| Appearance |
White to Off-white Solid |
| Storage |
Store at 2-8°C under inert atmosphere |
| Complexity |
661 |
| Exact Mass |
339.11788328 |
| Index Of Refraction |
1.812 |
| In Vitro |
Loxoribine induces maturation of human monocyte-derived dendritic cells DCs and stimulates their Th-1- and Th-17-polarizing capability. Loxoribine (250 μM; 48 hours) stimulates maturation of MoDCs as shown by up-regulation of CD80, CD83, CD40, CD54 and CCR7. loxoribine activates cells of the innate immune system selectively via the Toll-like receptor (TLR) 7/MyD88-dependent signaling pathway. |
| In Vivo |
Loxoribine (2 mg; s.c.or i.v.) activates murine natural killer (NK) cells in vivo. Animal Model: 8-12 weeks male CBA/J mice Dosage: 2 mg Administration: Subcutaneous or intravenous injection Result: activates murine natural killer (NK) cells in vivo. |
| PSA |
168.62000 |
| Target |
Toll-like Receptor (TLR); Influenza Virus |
| Vapor Pressure |
1.81E-16mmHg at 25°C |
| XLogP3-AA |
-2.7 |
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