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

• ChemBase ID: 103972
• Molecular Formular: C15H21N5O4
• Molecular Mass: 335.35834
• Monoisotopic Mass: 335.15935418
• SMILES: n1c2c(ncnc2NC2CCCC2)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)n1cnc2c1ncnc2NC1CCCC1
• InChI: InChI=1S/C15H21N5O4/c21-5-9-11(22)12(23)15(24-9)20-7-18-10-13(16-6-17-14(10)20)19-8-3-1-2-4-8/h6-9,11-12,15,21-23H,1-5H2,(H,16,17,19)/t9-,11-,12-,15-/m1/s1
• InChIKey: SQMWSBKSHWARHU-SDBHATRESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-[6-(cyclopentylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: N6-cyclopentyladenosine
• Synonyms: N^6-CYCLOPENTYLADENOSINE; N6-Cyclopentyladenosine; CPA; N6-Cyclopentyladenosine; (2R,3R,4S,5R)-2-(6-(Cyclopentylamino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol

Database IDs

• CAS Number: 41552-82-3
• MDL Number: MFCD00036845
• PubChem SID: 24277686; 162092754
• PubChem CID: 657378
• Chemspider ID: 571479
• Wikipedia Title: N6-Cyclopentyladenosine

CALCULATED PROPERTIES

• Acid pKa: 12.45399
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.5212316
• LogD (pH = 7.4): -0.4357705
• Log P: -0.4345579
• Molar Refractivity: 85.1022 cm^3
• Polarizability: 32.950607 Å^3
• Polar Surface Area: 125.55 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble12 mg/mL; DMSO: soluble23 mg/mL; H2O: soluble1.7 mg/mL
• Apperance: white to off-white solid

Safety Information

• Storage Condition: 2-8°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 ... ADORA1(134), ADORA2A(135), ADORA3(140)mouse ... Adora1(11539)rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

Product Information

• Purity: 95+%
• Empirical Formula (Hill Notation): C15H21N5O4

DETAILS

MP Biomedicals - 02153744

A1 adenosine receptor agonist.

Sigma Aldrich - C8031

Biochem/physiol Actions
Selective A1 adenosine receptor agonist.
Physical form
hygroscopic solid