2-(hydroxymethyl)-5-{6-[(2-phenylethyl)amino]-9H-purin-9-yl}oxolane-3,4-diol

• ChemBase ID: 134415
• Molecular Formular: C18H21N5O4
• Molecular Mass: 371.39044
• Monoisotopic Mass: 371.15935418
• SMILES: c1ccc(cc1)CCNc1c2c(ncn1)n(cn2)C1C(C(C(O1)CO)O)O
• Canonical SMILES: OCC1OC(C(C1O)O)n1cnc2c1ncnc2NCCc1ccccc1
• InChI: InChI=1S/C18H21N5O4/c24-8-12-14(25)15(26)18(27-12)23-10-22-13-16(20-9-21-17(13)23)19-7-6-11-4-2-1-3-5-11/h1-5,9-10,12,14-15,18,24-26H,6-8H2,(H,19,20,21)
• InChIKey: LGZYEDZSPHLISU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(hydroxymethyl)-5-{6-[(2-phenylethyl)amino]-9H-purin-9-yl}oxolane-3,4-diol
• IUPAC Traditional name: adenosine,6N-2-phenylethyl
• Synonyms: N6-(2-Phenylethyl)adenosine

Database IDs

• CAS Number: 20125-39-7
• MDL Number: MFCD00055128
• PubChem SID: 162228691; 24898349
• PubChem CID: 4398

CALCULATED PROPERTIES

• Acid pKa: 12.4539995
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.13372114
• LogD (pH = 7.4): 0.22260815
• Log P: 0.22387454
• Molar Refractivity: 98.0566 cm^3
• Polarizability: 37.620228 Å^3
• Polar Surface Area: 125.55 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M NaOH: soluble; ethanol: moderately soluble; H2O: very slightly soluble

Safety Information

• 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 ... ADORA1(134)

DETAILS

Sigma Aldrich - P107

Biochem/physiol Actions
Selective A1 adenosine receptor agonist.

Sigma Aldrich - P2673

Biochem/physiol Actions
Selective A1 adenosine receptor agonist.
Application
N6-(2-Phenylethyl)adenosine is an adenosine analogue that upon phosphorylation may be used to study the cystic fibrosis transmembrane conductance regulator (G551D-CFTR). N6-(2-Phenylethyl)adenosine is used to study the effects of adenosine analogues on adenosine receptor functions.