(2R,3R,4S,5R)-2-(6-{[(1R,2S,4S)-bicyclo[2.2.1]heptan-2-yl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 131281
• Molecular Formular: C17H23N5O4
• Molecular Mass: 361.39562
• Monoisotopic Mass: 361.17500424
• SMILES: c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)N[C@H]1C[C@H]2CC[C@@H]1C2
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N[C@H]1C[C@@H]2C[C@H]1CC2
• InChI: InChI=1S/C17H23N5O4/c23-5-11-13(24)14(25)17(26-11)22-7-20-12-15(18-6-19-16(12)22)21-10-4-8-1-2-9(10)3-8/h6-11,13-14,17,23-25H,1-5H2,(H,18,19,21)/t8-,9+,10-,11+,13+,14+,17+/m0/s1
• InChIKey: YKPCEENRZZBDMC-XSMNFLGNSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-(6-{[(1R,2S,4S)-bicyclo[2.2.1]heptan-2-yl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,4S,5R)-2-{6-[(1R,2S,4S)-bicyclo[2.2.1]heptan-2-ylamino]purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: (2S)-N6-[2-endo-Norbornyl]adenosine; PD 126,280; (S)-ENBA

Database IDs

• MDL Number: MFCD00069271
• PubChem SID: 24278429; 162225559
• PubChem CID: 5311431

CALCULATED PROPERTIES

• Acid pKa: 12.453983
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.33264688
• LogD (pH = 7.4): -0.24749959
• Log P: -0.2462919
• Molar Refractivity: 92.3202 cm^3
• Polarizability: 35.8946 Å^3
• Polar Surface Area: 125.55 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble3 mg/mL; ethanol, DMSO: soluble; H2O: insoluble0.01 mg/mL

Safety Information

• German water hazard class: 3

Pharmacology Properties

• Gene Information: human ... ADORA1(134)

DETAILS

Sigma Aldrich - E111

Biochem/physiol Actions
Selective A1 adenosine receptor agonist.