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

• ChemBase ID: 132938
• Molecular Formular: C18H21N7O4
• Molecular Mass: 399.40384
• Monoisotopic Mass: 399.16550219
• SMILES: CNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2NCc1ccc(cc1)N)O)O
• Canonical SMILES: CNC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2NCc1ccc(cc1)N
• InChI: InChI=1S/C18H21N7O4/c1-20-17(28)14-12(26)13(27)18(29-14)25-8-24-11-15(22-7-23-16(11)25)21-6-9-2-4-10(19)5-3-9/h2-5,7-8,12-14,18,26-27H,6,19H2,1H3,(H,20,28)(H,21,22,23)/t12-,13+,14-,18+/m0/s1
• InChIKey: LDYMCRRFCMRFKB-MOROJQBDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,5R)-5-(6-{[(4-aminophenyl)methyl]amino}-9H-purin-9-yl)-3,4-dihydroxy-N-methyloxolane-2-carboxamide
• IUPAC Traditional name: (2S,3S,4R,5R)-5-(6-{[(4-aminophenyl)methyl]amino}purin-9-yl)-3,4-dihydroxy-N-methyloxolane-2-carboxamide
• Synonyms: N6-(4-Aminobenzyl)-9-[5-(methylcarbonyl)-β-D-ribofuranosyl]adenine; N6-(4-Aminobenzyl)-N-methylcarboxamidoadenosine; AB-MECA

Database IDs

• CAS Number: 152918-26-8
• PubChem SID: 24277694; 162227215
• PubChem CID: 5310992

CALCULATED PROPERTIES

• Acid pKa: 12.393443
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -1.2600168
• LogD (pH = 7.4): -1.1581279
• Log P: -1.1567047
• Molar Refractivity: 104.5883 cm^3
• Polarizability: 39.464554 Å^3
• Polar Surface Area: 160.44 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble0.3 mg/mL; dilute aqueous base: soluble3.5 mg/mL; DMSO: soluble10 mg/mL; ethanol: soluble1 mg/mL; H2O: insoluble
• Apperance: off-white solid

Safety Information

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

DETAILS

Sigma Aldrich - A236

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