(2S,3S,4R,5R)-3,4-dihydroxy-5-(6-{[(3-iodophenyl)methyl]amino}-9H-purin-9-yl)-N-methyloxolane-2-carboxamide

• ChemBase ID: 132540
• Molecular Formular: C18H19IN6O4
• Molecular Mass: 510.28573
• Monoisotopic Mass: 510.05125112
• SMILES: CNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2NCc1cccc(c1)I)O)O
• Canonical SMILES: CNC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NCc1cccc(c1)I
• InChI: InChI=1S/C18H19IN6O4/c1-20-17(28)14-12(26)13(27)18(29-14)25-8-24-11-15(22-7-23-16(11)25)21-6-9-3-2-4-10(19)5-9/h2-5,7-8,12-14,18,26-27H,6H2,1H3,(H,20,28)(H,21,22,23)/t12-,13+,14-,18+/m0/s1
• InChIKey: HUJXGQILHAUCCV-MOROJQBDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,5R)-3,4-dihydroxy-5-(6-{[(3-iodophenyl)methyl]amino}-9H-purin-9-yl)-N-methyloxolane-2-carboxamide
• IUPAC Traditional name: (2S,3S,4R,5R)-3,4-dihydroxy-5-(6-{[(3-iodophenyl)methyl]amino}purin-9-yl)-N-methyloxolane-2-carboxamide
• Synonyms: 1-Deoxy-1-[6-[((3-Iodophenyl)methyl)amino]-9H-purin-9-yl]-N-methyl-β-D-ribofuranuronamide; N6-(3-Iodobenzyl)adenosine-5′-N-methyluronamide; IB-MECA

Database IDs

• CAS Number: 152918-18-8
• MDL Number: MFCD00671785
• PubChem SID: 162226817; 24277717
• PubChem CID: 123683

CALCULATED PROPERTIES

• Acid pKa: 12.3933735
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.51598185
• LogD (pH = 7.4): 0.5999755
• Log P: 0.6011658
• Molar Refractivity: 113.2504 cm^3
• Polarizability: 43.53961 Å^3
• Polar Surface Area: 134.42 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: aqueous acid: insoluble; aqueous base: insoluble; DMSO: >5 mg/mL; ethanol: >10 mg/mL (hot); H2O: insoluble
• Apperance: white solid

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 ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140)rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - I146

Biochem/physiol Actions
Selective A3 adenosine receptor agonist.
Legal Information
Sold under license from the National Institutes of Health.