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

• ChemBase ID: 169994
• Molecular Formular: C18H24N6O4
• Molecular Mass: 388.42096
• Monoisotopic Mass: 388.18590328
• SMILES: [C@@H]1(C([C@H](O[C@H]1n1c2c(nc1)c(nc(n2)C#CCCCC)N)C(=O)NCC)O)O
• Canonical SMILES: CCCCC#Cc1nc(N)c2c(n1)n(cn2)[C@@H]1O[C@@H](C([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-RGPOINIYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,4S,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,4S,5R)-5-[6-amino-2-(hex-1-yn-1-yl)purin-9-yl]-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
• Synonyms: 2-Hexynyl-5'-N-ethylcarboxamidoadenosine; 2-Hexynyl-NECA; HENECA; 2-Hexynyl-5'-N-ethylcarboxamidoadenosine

Database IDs

• CAS Number: 141018-30-6
• PubChem SID: 162264126
• PubChem CID: 71317251

CALCULATED PROPERTIES

• Acid pKa: 12.391074
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): 0.8605745
• LogD (pH = 7.4): 0.8605851
• 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
• Apperance: Yellow Solid
• Melting Point: 180-182°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - H325500

Possesses high affinity to adenosine (A1 & A2) receptors, inhibiting radioligands from binding to these sites

REFERENCES

• Varani, K., et al.: Biochem. Pharmacol., 70, 1601 (2005)
• Joseph, T., et al.: Chem. Biol. Drug Des., 72, 395 (2005)
• Ivanov, A., et al.: J. Med. Chem., 51, 2088 (2005)