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

• ChemBase ID: 155012
• Molecular Formular: C15H21N5O5
• Molecular Mass: 351.35774
• Monoisotopic Mass: 351.1542688
• SMILES: c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)N[C@H]1CCC[C@@H]1O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N[C@H]1CCC[C@@H]1O
• InChI: InChI=1S/C15H21N5O5/c21-4-9-11(23)12(24)15(25-9)20-6-18-10-13(16-5-17-14(10)20)19-7-2-1-3-8(7)22/h5-9,11-12,15,21-24H,1-4H2,(H,16,17,19)/t7-,8-,9+,11+,12+,15+/m0/s1
• InChIKey: GYWXTRVEUURNEW-TVDBPQCTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-(6-{[(1S,2S)-2-hydroxycyclopentyl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,4S,5R)-2-(6-{[(1S,2S)-2-hydroxycyclopentyl]amino}purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: N-[(1S, trans)-2-Hydroxycyclopentyl]adenosine; GR 79236X

Database IDs

• CAS Number: 124555-18-6
• MDL Number: MFCD00884605
• PubChem SID: 162249150
• PubChem CID: 9884817

CALCULATED PROPERTIES

• Acid pKa: 12.450496
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -1.5933163
• LogD (pH = 7.4): -1.5106308
• Log P: -1.5094615
• Molar Refractivity: 86.4637 cm^3
• Polarizability: 33.62569 Å^3
• Polar Surface Area: 145.78 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble12 mg/mL
• Apperance: white solid

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22-36/37/38
• Safety Statements: 26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99% (HPLC)
• Empirical Formula (Hill Notation): C15H21O5N5

DETAILS

Sigma Aldrich - G5794

Biochem/physiol Actions
A1 adenosine receptor agonist
Legal Information
Sold for research purposes under agreement from Glaxo-Smith-Kline