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

• ChemBase ID: 155332
• Molecular Formular: C18H22N6O4
• Molecular Mass: 386.40508
• Monoisotopic Mass: 386.17025321
• SMILES: c1cc(ccc1CCNc1c2c(ncn1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)N
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NCCc1ccc(cc1)N
• InChI: InChI=1S/C18H22N6O4/c19-11-3-1-10(2-4-11)5-6-20-16-13-17(22-8-21-16)24(9-23-13)18-15(27)14(26)12(7-25)28-18/h1-4,8-9,12,14-15,18,25-27H,5-7,19H2,(H,20,21,22)/t12-,14-,15-,18-/m1/s1
• InChIKey: XTPOZVLRZZIEBW-SCFUHWHPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-(6-{[2-(4-aminophenyl)ethyl]amino}-9H-purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,4S,5R)-2-(6-{[2-(4-aminophenyl)ethyl]amino}purin-9-yl)-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: APNEA; Adenosine, N6-2-(4-aminophenyl)ethyl; N-[2-(4-Aminophenyl)ethyl]-adenosine; N6-2-(4-Aminophenyl)ethyladenosine

Database IDs

• CAS Number: 89705-21-5
• MDL Number: MFCD00211351
• PubChem SID: 162249470; 24277722
• PubChem CID: 9952135

CALCULATED PROPERTIES

• Acid pKa: 12.4539995
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -0.7371684
• LogD (pH = 7.4): -0.60687244
• Log P: -0.6050514
• Molar Refractivity: 102.757 cm^3
• Polarizability: 38.777363 Å^3
• Polar Surface Area: 151.57 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble14 mg/mL; DMSO: soluble; H2O: insoluble; methanol: slightly soluble0.2 mg/mL

Safety Information

• 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 ... ADORA3(140)rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

Product Information

• Purity: >95%
• Empirical Formula (Hill Notation): C18H22N6O4

DETAILS

Sigma Aldrich - A202

Biochem/physiol Actions
Potent, non-selective A3 adenosine receptor agonist.