{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid amine

• ChemBase ID: 132060
• Molecular Formular: C19H27N8O12P
• Molecular Mass: 590.437841
• Monoisotopic Mass: 590.14860497
• SMILES: c1cn(c(=O)[nH]c1=O)C1C(C(C(O1)COP(=O)(O)OC1C(OC(C1O)n1cnc2c1ncnc2N)CO)O)O.N
• Canonical SMILES: OCC1OC(C(C1OP(=O)(OCC1OC(C(C1O)O)n1ccc(=O)[nH]c1=O)O)O)n1cnc2c1ncnc2N.N
• InChI: InChI=1S/C19H24N7O12P.H3N/c20-15-10-16(22-5-21-15)26(6-23-10)18-13(31)14(7(3-27)36-18)38-39(33,34)35-4-8-11(29)12(30)17(37-8)25-2-1-9(28)24-19(25)32;/h1-2,5-8,11-14,17-18,27,29-31H,3-4H2,(H,33,34)(H2,20,21,22)(H,24,28,32);1H3
• InChIKey: PRPZHNJNQXWARV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}({[5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxy})phosphinic acid amine
• IUPAC Traditional name: [5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy[5-(2,4-dioxo-3H-pyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methoxyphosphinic acid amine
• Synonyms: ApU; Adenylyl(3′→5′)uridine ammonium salt

Database IDs

• CAS Number: 93839-87-3
• EC Number: 298-860-7
• MDL Number: MFCD00078904
• PubChem SID: 162226337
• PubChem CID: 14228830

CALCULATED PROPERTIES

• Acid pKa: 1.832419
• H Acceptors: 14
• H Donor: 7
• LogD (pH = 5.5): -6.184077
• LogD (pH = 7.4): -6.1129026
• Log P: -6.4352336
• Molar Refractivity: 122.8551 cm^3
• Polarizability: 48.813793 Å^3
• Polar Surface Area: 274.17 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C