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

• ChemBase ID: 103992
• Molecular Formular: C16H18N6O4
• Molecular Mass: 358.35192
• Monoisotopic Mass: 358.13895309
• SMILES: Nc1nc(Nc2ccccc2)nc2c1ncn2[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1nc(Nc1ccccc1)nc2N
• InChI: InChI=1S/C16H18N6O4/c17-13-10-14(21-16(20-13)19-8-4-2-1-3-5-8)22(7-18-10)15-12(25)11(24)9(6-23)26-15/h1-5,7,9,11-12,15,23-25H,6H2,(H3,17,19,20,21)/t9-,11-,12-,15-/m1/s1
• InChIKey: SCNILGOVBBRMBK-SDBHATRESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-[6-amino-2-(phenylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: 2-phenylaminoadenosine
• Synonyms: 2-PHENYLAMINOADENOSINE; CV-1808; 2-Phenylaminoadenosine

Database IDs

• CAS Number: 53296-10-9
• MDL Number: MFCD00055119
• PubChem SID: 24277727; 162091865
• PubChem CID: 6917803

CALCULATED PROPERTIES

• Acid pKa: 12.420938
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): 0.025738517
• LogD (pH = 7.4): 0.027718443
• Log P: 0.027747925
• Molar Refractivity: 91.6278 cm^3
• Polarizability: 35.182934 Å^3
• Polar Surface Area: 151.57 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble3.6 mg/mL; absolute ethanol: slightly soluble; ethanol: water (1:1): soluble; H2O: insoluble; methanol: soluble (hot)
• Apperance: white solid

Safety Information

• Storage Condition: -20°C
• 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)rat ... Adora1(29290), Adora2a(25369)

Product Information

• Purity: >97%

DETAILS

MP Biomedicals - 02153794

A2 adenosine agonist.

Sigma Aldrich - P101

Biochem/physiol Actions
Selective A2 adenosine receptor agonist; potent coronary vasodilator; weak inhibitor of adenosine uptake by rat cerebral cortical synaptosomes.
Reconstitution
Solutions should be freshly prepared.