(2R,3R,4S,5R)-2-[2-(hex-1-yn-1-yl)-6-(methylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol

• ChemBase ID: 154257
• Molecular Formular: C17H23N5O4
• Molecular Mass: 361.39562
• Monoisotopic Mass: 361.17500424
• SMILES: CCCCC#Cc1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)O)NC
• Canonical SMILES: CCCCC#Cc1nc(NC)c2c(n1)n(cn2)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)CO
• InChI: InChI=1S/C17H23N5O4/c1-3-4-5-6-7-11-20-15(18-2)12-16(21-11)22(9-19-12)17-14(25)13(24)10(8-23)26-17/h9-10,13-14,17,23-25H,3-5,8H2,1-2H3,(H,18,20,21)/t10-,13-,14-,17-/m1/s1
• InChIKey: KOCIMZNSNPOGOP-IWCJZZDYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R,4S,5R)-2-[2-(hex-1-yn-1-yl)-6-(methylamino)-9H-purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• IUPAC Traditional name: (2R,3R,4S,5R)-2-[2-(hex-1-yn-1-yl)-6-(methylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• Synonyms: 2-(1-Hexynyl)-N6-methyladenosine; HEMADO

Database IDs

• CAS Number: 403842-38-6
• MDL Number: MFCD06798373
• PubChem SID: 162248396
• PubChem CID: 10981286

CALCULATED PROPERTIES

• Acid pKa: 12.454002
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 1.0742675
• LogD (pH = 7.4): 1.0743268
• Log P: 1.0743314
• Molar Refractivity: 92.826 cm^3
• Polarizability: 36.233162 Å^3
• Polar Surface Area: 125.55 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: soluble16 mg/mL
• Apperance: white solid

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99% (HPLC)
• Empirical Formula (Hill Notation): C17H23N5O4

DETAILS

Sigma Aldrich - H3288

Biochem/physiol Actions
A3 adenosine receptor agonist