(2R,3R,4S,5R)-2-{4-amino-1H-imidazo[4,5-c]pyridin-1-yl}-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 155233
• Molecular Formular: C11H14N4O4
• Molecular Mass: 266.25326
• Monoisotopic Mass: 266.10150495
• SMILES: c1cnc(c2c1n(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)n1cnc2c1ccnc2N
• InChI: InChI=1S/C11H14N4O4/c12-10-7-5(1-2-13-10)15(4-14-7)11-9(18)8(17)6(3-16)19-11/h1-2,4,6,8-9,11,16-18H,3H2,(H2,12,13)/t6-,8-,9-,11-/m1/s1
• InChIKey: DBZQFUNLCALWDY-PNHWDRBUSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-{4-amino-1H-imidazo[4,5-c]pyridin-1-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,4S,5R)-2-{4-aminoimidazo[4,5-c]pyridin-1-yl}-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 4-Amino-1-(β-D-ribofuranosyl)-1H-imidazo(4,5)-pyridine; 3-Deazaadenosine

Database IDs

• CAS Number: 6736-58-9
• MDL Number: MFCD00153951
• PubChem SID: 24278391; 162249371
• PubChem CID: 23190

CALCULATED PROPERTIES

• Acid pKa: 12.455601
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -1.7644441
• LogD (pH = 7.4): -1.7527436
• Log P: -1.752588
• Molar Refractivity: 64.4218 cm^3
• Polarizability: 26.000923 Å^3
• Polar Surface Area: 126.65 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble10 mg/mL (with heating to 60 °C)

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: rat ... Adora1(29290), Adora2a(25369), Adora3(25370)

Product Information

• Empirical Formula (Hill Notation): C11H14N4O4

DETAILS

Sigma Aldrich - D8296

Biochem/physiol Actions
Possesses antiviral activity1 inhibitor of leukocyte adhesion to TNF-treated endothelial cells.2