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

• ChemBase ID: 153472
• Molecular Formular: C18H21N5O4
• Molecular Mass: 371.39044
• Monoisotopic Mass: 371.15935418
• SMILES: Cc1ccccc1CNc1c2c(ncn1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NCc1ccccc1C
• InChI: InChI=1S/C18H21N5O4/c1-10-4-2-3-5-11(10)6-19-16-13-17(21-8-20-16)23(9-22-13)18-15(26)14(25)12(7-24)27-18/h2-5,8-9,12,14-15,18,24-26H,6-7H2,1H3,(H,19,20,21)/t12-,14-,15-,18-/m1/s1
• InChIKey: OOEMZCZWZXHBKW-SCFUHWHPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-{[(2-methylphenyl)methyl]amino}-9H-purin-9-yl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-{[(2-methylphenyl)methyl]amino}purin-9-yl)oxolane-3,4-diol
• Synonyms: N-[(2-Methylphenyl)methyl]adenosine; Metrifudil

Database IDs

• MDL Number: MFCD00798877
• PubChem SID: 162247611
• PubChem CID: 65710

CALCULATED PROPERTIES

• Acid pKa: 12.453921
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.3634426
• LogD (pH = 7.4): 0.44744492
• Log P: 0.4486347
• Molar Refractivity: 98.3428 cm^3
• Polarizability: 37.617466 Å^3
• Polar Surface Area: 125.55 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M NaOH: soluble0.9 mg/mL; DMSO: soluble6 mg/mL; ethanol: soluble1.4 mg/mL; H2O: soluble0.3 mg/mL

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... ADORA2A(135), ADORA2B(136)

Product Information

• Empirical Formula (Hill Notation): C18H21N5O4

DETAILS

Sigma Aldrich - M225

Biochem/physiol Actions
Adenosine receptor agonist which displays some selectivity for the A2 receptor type.