(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(9H-purin-9-yl)oxolane-3,4-diol

• ChemBase ID: 111073
• Molecular Formular: C10H12N4O4
• Molecular Mass: 252.22668
• Monoisotopic Mass: 252.08585488
• SMILES: n1c2cncnc2n(c1)[C@@H]1O[C@@H]([C@@H](O)[C@H]1O)CO
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2
• InChI: InChI=1S/C10H12N4O4/c15-2-6-7(16)8(17)10(18-6)14-4-13-5-1-11-3-12-9(5)14/h1,3-4,6-8,10,15-17H,2H2/t6-,7-,8-,10-/m1/s1
• InChIKey: MRWXACSTFXYYMV-FDDDBJFASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(9H-purin-9-yl)oxolane-3,4-diol
• IUPAC Traditional name: purine nucleoside; nebularine
• Synonyms: Purine 9β-D-ribofuranoside; Nebularine; PURINE RIBOSIDE

Database IDs

• CAS Number: 550-33-4
• EC Number: 208-981-9
• MDL Number: MFCD00022819
• Beilstein Number: 91539
• PubChem SID: 162096225
• PubChem CID: 68368

CALCULATED PROPERTIES

• Acid pKa: 12.454004
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.8643277
• LogD (pH = 7.4): -1.8565989
• Log P: -1.8564955
• Molar Refractivity: 58.1817 cm^3
• Polarizability: 23.381533 Å^3
• Polar Surface Area: 113.52 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 178-180 °C
• Optical Rotation: [α]20/D -46±2°, c = 1% in H2O

Safety Information

• RTECS: UO9100000
• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26-36
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C10H12N4O4

DETAILS

MP Biomedicals - 05217619

MP Biomedicals Rare Chemical collection

Sigma Aldrich - 82590

Other Notes
Substrate for adenosine deaminase1