(2S,3S,4R,5R)-5-[6-(benzylamino)-9H-purin-9-yl]-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide

• ChemBase ID: 153462
• Molecular Formular: C19H22N6O4
• Molecular Mass: 398.41578
• Monoisotopic Mass: 398.17025321
• SMILES: CCNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2NCc1ccccc1)O)O
• Canonical SMILES: CCNC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NCc1ccccc1
• InChI: InChI=1S/C19H22N6O4/c1-2-20-18(28)15-13(26)14(27)19(29-15)25-10-24-12-16(22-9-23-17(12)25)21-8-11-6-4-3-5-7-11/h3-7,9-10,13-15,19,26-27H,2,8H2,1H3,(H,20,28)(H,21,22,23)/t13-,14+,15-,19+/m0/s1
• InChIKey: VVHDYJFDZYHAMR-QCUYGVNKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,5R)-5-[6-(benzylamino)-9H-purin-9-yl]-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
• IUPAC Traditional name: (2S,3S,4R,5R)-5-[6-(benzylamino)purin-9-yl]-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
• Synonyms: N6-Benzyl-NECA; N6-Benzyl-5′-N-ethylcarboxamidoadenosine

Database IDs

• MDL Number: MFCD00274027
• PubChem SID: 162247601
• PubChem CID: 10046412

CALCULATED PROPERTIES

• Acid pKa: 12.393076
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.05615529
• LogD (pH = 7.4): 0.027839007
• Log P: 0.029029272
• Molar Refractivity: 104.6365 cm^3
• Polarizability: 40.135998 Å^3
• Polar Surface Area: 134.42 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble1.28 mg/mL
• Apperance: white solid

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ADORA3(140)

Product Information

• Empirical Formula (Hill Notation): C19H22N6O4

DETAILS

Sigma Aldrich - B152

Biochem/physiol Actions
Selective A3 adenosine receptor agonist.