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

• ChemBase ID: 132669
• Molecular Formular: C12H16N6O4
• Molecular Mass: 308.29324
• Monoisotopic Mass: 308.12330302
• SMILES: CCNC(=O)[C@@H]1[C@H]([C@H]([C@@H](O1)n1cnc2c1ncnc2N)O)O
• Canonical SMILES: CCNC(=O)[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cnc2c1ncnc2N
• InChI: InChI=1S/C12H16N6O4/c1-2-14-11(21)8-6(19)7(20)12(22-8)18-4-17-5-9(13)15-3-16-10(5)18/h3-4,6-8,12,19-20H,2H2,1H3,(H,14,21)(H2,13,15,16)/t6-,7+,8-,12+/m0/s1
• InChIKey: JADDQZYHOWSFJD-FLNNQWSLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S,3S,4R,5R)-5-(6-amino-9H-purin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
• IUPAC Traditional name: (2S,3S,4R,5R)-5-(6-aminopurin-9-yl)-N-ethyl-3,4-dihydroxyoxolane-2-carboxamide
• Synonyms: NECA; 5′-N-ethylcarboxamidoadenosine; 5′-(N-Ethylcarboxamido)adenosine

Database IDs

• CAS Number: 35920-39-9; 78647-50-4
• MDL Number: MFCD00069195
• PubChem SID: 162226946; 24277684
• PubChem CID: 448222

CALCULATED PROPERTIES

• Acid pKa: 12.393688
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -2.11228
• LogD (pH = 7.4): -1.9988141
• Log P: -1.9971479
• Molar Refractivity: 74.5305 cm^3
• Polarizability: 28.813255 Å^3
• Polar Surface Area: 148.41 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 0.1 M HCl: soluble3.4 mg/mL (Solutions may be stored for several days at 4 °C.); 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble0.2 mg/mL (Solutions may be stored for several days at 4 °C.); DMSO: soluble14 mg/mL (Solutions may be stored for several days at 4 °C.); ethanol: soluble (Solutions may be stored for several days at 4 °C.); H2O: insoluble
• Apperance: white powder

Safety Information

• RTECS: VJ2232000
• European Hazard Symbols: Highly toxic (T+)
• UN Number: 2811
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 28
• Safety Statements: 22-26-36-45
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300
• GHS Precautionary statements: P264-P301 + P310
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• RID/ADR: UN 2811 6.1/PG 2
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... ADORA1(134), ADORA2A(135), ADORA2B(136), ADORA3(140)rat ... Adora1(29290), Adora2a(25369), Adora2b(29316), Adora3(25370)

DETAILS

Sigma Aldrich - E2387

Biochem/physiol Actions
Potent adenosine receptor agonist with nearly equal affinity at A1 and A2 receptors.