2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one

• ChemBase ID: 89365
• Molecular Formular: C10H13N5O5
• Molecular Mass: 283.24072
• Monoisotopic Mass: 283.09166854
• SMILES: n1([C@H]2[C@@H]([C@H](O)[C@H](O2)CO)O)c2c(nc1)c(=O)[nH]c(n2)N
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(N)[nH]c2=O
• InChI: InChI=1S/C10H13N5O5/c11-10-13-7-4(8(19)14-10)12-2-15(7)9-6(18)5(17)3(1-16)20-9/h2-3,5-6,9,16-18H,1H2,(H3,11,13,14,19)/t3-,5-,6-,9-/m1/s1
• InChIKey: NYHBQMYGNKIUIF-UUOKFMHZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6,9-dihydro-1H-purin-6-one
• IUPAC Traditional name: guanosine
• Synonyms: 2-Amino-9-beta-D-ribofuranosyl-9H-purine-6-1H-one; Guanosine; 9-(β-D-Ribofuranosyl)guanine; Guanine-9-β-D-ribofuranoside; Guanosine; 2-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-1H-purin-6(9H)-one; Guanine riboside; 9-(β-D-呋喃核糖基)鸟嘌呤; 鸟嘌呤-9-β-D-呋喃核糖苷; 鸟苷

Database IDs

• CAS Number: 118-00-3
• EC Number: 204-227-8
• MDL Number: MFCD00010182
• Beilstein Number: 625911
• PubChem SID: 162076245; 24895268; 24895251
• PubChem CID: 6802; 765
• CHEBI ID: 16750
• CHEMBL: 375655
• Chemspider ID: 6544
• DrugBank ID: DB02857
• KEGG ID: C00387
• MeSH Name: Guanosine
• Unique Ingredient Identifier: 12133JR80S
• Wikipedia Title: Guanosine

CALCULATED PROPERTIES

• Acid pKa: 10.155725
• H Acceptors: 8
• H Donor: 5
• LogD (pH = 5.5): -2.7063062
• LogD (pH = 7.4): -2.7068908
• Log P: -2.7062182
• Molar Refractivity: 64.6211 cm^3
• Polarizability: 24.328236 Å^3
• Polar Surface Area: 155.22 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M NaOH: soluble0.1 g/mL, clear, slightly yellow
• Melting Point: 250 °C (dec.)(lit.); 250(dec.)°C
• Optical Rotation: [α]20/D -73±2°, c = 1.5% in 0.1 M NaOH; [α]20/D -73±2°, c = 1.5% in 1 M NaOH

Safety Information

• Storage Warning: Toxic
• RTECS: MF8750000
• European Hazard Symbols: Toxic (T)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 3
• Risk Statements: 25
• Safety Statements: 45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H301
• GHS Precautionary statements: P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 3

Product Information

• Purity: ≥97.0% (HPLC); ≥98%; ≥98.0% (HPLC); 98%
• Suitability: suitable for cell culture
• Impurities: ≤3% water; ≤6.0% water
• Product Line: BioReagent
• Empirical Formula (Hill Notation): C10H13N5O5

DETAILS

Sigma Aldrich - 75903

Other Notes
Currently available only in Europe.
Application
Guanosine is a purine nucleoside that upon sequential phosphoylation (kinases) forms GTP which is used by RNA polymerases to synthesis RNA(s). GTP is also important in a wide range of GTPase-dependent cell signaling processes. Guanosine is used in selective matricies such a guanosine gels (G-gels) for use in capillary electrophoresis chiral selection and other applications.

Sigma Aldrich - G6264

Application
For use in cell culture applications as a precursor of GMP, GDP, GTP and cGMP.

Sigma Aldrich - G6752

Packaging
1, 25, 100, 500 g in poly bottle