(2S,3S,4R,5R)-5-[6-amino-2-(hex-1-yn-1-yl)-9H-purin-9-yl]-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide

• ChemBase ID: 133706
• Molecular Formular: C18H24N6O4
• Molecular Mass: 388.42096
• Monoisotopic Mass: 388.18590328
• SMILES: CCCCC#Cc1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@@H]([C@H](O1)C(=O)NCC)O)O)N
• Canonical SMILES: CCCCC#Cc1nc(N)c2c(n1)n(cn2)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)C(=O)NCC
• InChI: InChI=1S/C18H24N6O4/c1-3-5-6-7-8-10-22-15(19)11-16(23-10)24(9-21-11)18-13(26)12(25)14(28-18)17(27)20-4-2/h9,12-14,18,25-26H,3-6H2,1-2H3,(H,20,27)(H2,19,22,23)/t12-,13+,14-,18+/m0/s1
• InChIKey: FDEACFAXFCKCHZ-MOROJQBDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,5R)-5-[6-amino-2-(hex-1-yn-1-yl)-9H-purin-9-yl]-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
• IUPAC Traditional name: (2S,3S,4R,5R)-5-[6-amino-2-(hex-1-yn-1-yl)purin-9-yl]-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
• Synonyms: 2-(1-Hexyn-1-yl)adenosine-5′-N-ethyluronamide; 2-Hexynyl-5′-ethylcarboxamidoadenosine; HE-NECA

Database IDs

• CAS Number: 141018-30-6(anhydrous)
• MDL Number: MFCD03095611
• PubChem SID: 24278473; 162227983
• PubChem CID: 164437

CALCULATED PROPERTIES

• Acid pKa: 12.391074
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.8605046
• LogD (pH = 7.4): 0.86058426
• Log P: 0.86058974
• Molar Refractivity: 98.6675 cm^3
• Polarizability: 38.679424 Å^3
• Polar Surface Area: 148.41 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; 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 ... ADORA2A(135), ADORA2B(136)

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - H8034

Biochem/physiol Actions
A2 adenosine receptor agonist