(2R,3R,4S,5R)-2-[6-(benzylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 103051
• Molecular Formular: C17H19N5O4
• Molecular Mass: 357.36386
• Monoisotopic Mass: 357.14370411
• SMILES: n1c2c(ncnc2NCc2ccccc2)n(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)n1cnc2c1ncnc2NCc1ccccc1
• InChI: InChI=1S/C17H19N5O4/c23-7-11-13(24)14(25)17(26-11)22-9-21-12-15(19-8-20-16(12)22)18-6-10-4-2-1-3-5-10/h1-5,8-9,11,13-14,17,23-25H,6-7H2,(H,18,19,20)/t11-,13-,14-,17-/m1/s1
• InChIKey: MRPKNNSABYPGBF-LSCFUAHRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-[6-(benzylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,4S,5R)-2-[6-(benzylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: N6-Benzyladenosine; 6-Benzylaminopurine riboside; N^6-BENZYLADENOSINE; N6-苄基腺苷

Database IDs

• CAS Number: 4294-16-0
• EC Number: 224-298-9
• MDL Number: MFCD00005740
• Beilstein Number: 56815
• PubChem SID: 162090261; 24848022
• PubChem CID: 92208

CALCULATED PROPERTIES

• Acid pKa: 12.453924
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.14998946
• LogD (pH = 7.4): -0.06597664
• Log P: -0.06478667
• Molar Refractivity: 93.3016 cm^3
• Polarizability: 35.859524 Å^3
• Polar Surface Area: 125.55 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 184-186 °C; 185-187 C

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ADORA3(140)rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

Product Information

• Purity: ≥99.0%
• Empirical Formula (Hill Notation): C17H19N5O4

DETAILS

MP Biomedicals - 02150449

Crystalline
An A₁ Adenosine receptor agonist.

Sigma Aldrich - 13155

Packaging
1 g in glass bottle