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

• ChemBase ID: 105640
• Molecular Formular: C15H20ClN5O4
• Molecular Mass: 369.8034
• Monoisotopic Mass: 369.12038183
• SMILES: OC[C@H]1O[C@H]([C@H](O)[C@@H]1O)n1cnc2c(NC3CCCC3)nc(Cl)nc12
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(Cl)nc2NC1CCCC1
• InChI: InChI=1S/C15H20ClN5O4/c16-15-19-12(18-7-3-1-2-4-7)9-13(20-15)21(6-17-9)14-11(24)10(23)8(5-22)25-14/h6-8,10-11,14,22-24H,1-5H2,(H,18,19,20)/t8-,10-,11-,14-/m1/s1
• InChIKey: XSMYYYQVWPZWIZ-IDTAVKCVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-[2-chloro-6-(cyclopentylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: ccpa (biochemistry)
• Synonyms: CCPA (biochemistry); CCPA; 2-Chloro-N6-cyclopentyladenosine; 2-CHLORO-N^6-CYCLO-PENTYLADENOSINE

Database IDs

• CAS Number: 37739-05-2
• MDL Number: MFCD00078574
• PubChem SID: 162093815; 24892583
• PubChem CID: 123807
• CHEMBL: 284969
• Chemspider ID: 110356
• IUPHAR ligand ID: 379
• MeSH Name: 2-chloro-N(6)cyclopentyladenosine
• Wikipedia Title: CCPA_(biochemistry)

CALCULATED PROPERTIES

• Acid pKa: 12.45397
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.47398627
• LogD (pH = 7.4): 0.4739885
• Log P: 0.4739924
• Molar Refractivity: 90.6008 cm^3
• Polarizability: 35.012794 Å^3
• Polar Surface Area: 125.55 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• RTECS: AU7357555
• German water hazard class: 3
• Safety Statements: R
• 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), ADORA2B(136), ADORA3(140)rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

DETAILS

MP Biomedicals - 02193632

(CCPA)
A very selective A₁ Adenosine receptor agonist.

Sigma Aldrich - C7938

Biochem/physiol Actions
A1 adenosine receptor agonist with high selectivity: reportedly 10,000-fold for A1 over A2 receptors.
Application
2-Chloro-N6-cyclopentyladenosine (CCPA) may be used as an A1 adenosine receptor agonist with high selectivity. CCPA is often used with other adenosine receptor agonists and antagonist to resolve A(1), A(2A) and A(3) receptor functions. These include DPCPX (A(1) receptor antagonist), 4-(2-[7-amino-2-(2-furyl)[1,2,4]triazolo[2,3-α][1,3,5]triazin-5-ylamino]ethyl)phenol (A(2A) receptor antagonist), and 4-[2-[[6-amino-9-(N-ethyl-β-D-ribofuranuronamidosyl)-9H-purin-2-yl]amino]ethyl]benzenepropanoic acid hydrochloride (A(2A) receptor agonist), and Cl-IB-MECA, (A(3)) receptor agonist).