Nebularine

Base Information

• Chemical Name: Nebularine
• CAS No.: 550-33-4
• Molecular Formula: C10H12 N4 O4
• Molecular Weight: 252.23
• Hs Code.: 2934999090
• European Community (EC) Number: 208-981-9
• UNII: B8B604PS4P
• DSSTox Substance ID: DTXSID701015580
• Nikkaji Number: J1.609H
• Wikidata: Q3874106
• Metabolomics Workbench ID: 51208
• ChEMBL ID: CHEMBL1399702
• Mol file: 550-33-4.mol

Synonyms:9-(beta-D-ribofuranosyl)purine;nebularine;purine ribonucleoside;purine riboside;purine-1-D-ribofuranoside

Chemical Property of Nebularine

Chemical Property:

• Vapor Pressure: 7.71E-15mmHg at 25°C
• Melting Point: 181-182°C
• Refractive Index: 1.6500 (estimate)
• Boiling Point: 591.6°Cat760mmHg
• PKA: 13.13±0.70(Predicted)
• Flash Point: 311.6°C
• PSA: 113.52000
• Density: 1.91g/cm³
• LogP: -1.56220
• Storage Temp.: 2-8°C
• Solubility.: DMSO (Slightly), Ethanol, Methanol (Slightly)
• XLogP3: -0.7
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 2
• Exact Mass: 252.08585488
• Heavy Atom Count: 18
• Complexity: 308

Purity/Quality:

97% ^*data from raw suppliers

Nebularine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=C2C(=NC=N1)N(C=N2)C3C(C(C(O3)CO)O)O
• Isomeric SMILES: C1=C2C(=NC=N1)N(C=N2)[C@H]3[C@@H]([C@@H]([C@H](O3)CO)O)O
• Description: This purine base is produced by Agarius nebularis Batsch. (Syn. Clitocybe nebularis). It is laevorotatory with [α]25D - 48.6° (c 1.0, H20).
• Uses: Nebularine is shown to have inhibitory effects against mouse Sarcoma 180 and mycobacteria.

Technology Process of Nebularine

There total 26 articles about Nebularine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 83.0%

2',3',5'-tri-O-acetylnebularine (15981-63-2) → Nebularin (550-33-4)

Guidance literature:

With ammonia; In ethanol; for 48h; Ambient temperature;

DOI:10.1055/s-1984-30851

Reference yield: 82.0%

6-mercaptopurine riboside (574-25-4) → Nebularin (550-33-4)

Guidance literature:

With nitric acid; In water; at 50 ℃; for 1h; Temperature; Time; Concentration;

DOI:10.1080/10426507.2016.1225057

Reference yield: 80.0%

purine (120-73-0) + uridine (58-96-8) → Nebularin (550-33-4)

Guidance literature:

With Enterobacter gergoviae CECT 875 in agar; In phosphate buffer; at 60 ℃; for 3h; pH=7.0; Enzymatic reaction;

DOI:10.1016/S0040-4039(03)00225-9

upstream raw materials:

6-Chloropurine riboside

2-Chloro-purine riboside

9-(2,3,5-tri-O-benzoyl-β-D-ribofuranosyl)-9H-purine

2',3',5'-tri-O-acetylnebularine

Downstream raw materials:

inosine 5'-monophosphate

4,5-pyrimidinediamine

formic acid

9-{5'-O-(4,4'-dimethoxytriphenylmethyl)-2'-O-[(tert-butyl)dimethylsilyl]-β-D-ribofuranosyl}-9H-purine

Refernces

• 1、 -. "CYCLIC DINUCLEOTIDES AS STING AGONISTS". Page/Page column 204-206. . Retrieved 2019/07/19.
• 2、 Xia, Ran,Xie, Ming-Sheng,Niu, Hong-Ying,Qu, Gui-Rong,Guo, Hai-Ming. "Efficient synthesis of nebularine and vidarabine via dehydrazination of (hetero)aromatics catalyzed by CuSO4 in water". . p. 1077 - 1081. Retrieved 2014/03/21.