[(2-{[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}(hydroxy)phosphoryl)oxy]methyl}-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-4-hydroxyoxolan-3-yl)oxy]phosphonic acid sodium

• ChemBase ID: 131338
• Molecular Formular: C19H25N7NaO15P2
• Molecular Mass: 676.376992
• Monoisotopic Mass: 676.07815568
• SMILES: c1cn(c(=O)[nH]c1=O)C1C(C(C(O1)COP(=O)(O)OC1C(OC(C1O)n1cnc2c1ncnc2N)CO)OP(=O)(O)O)O.[Na]
• Canonical SMILES: OCC1OC(C(C1OP(=O)(OCC1OC(C(C1OP(=O)(O)O)O)n1ccc(=O)[nH]c1=O)O)O)n1cnc2c1ncnc2N.[Na]
• InChI: InChI=1S/C19H25N7O15P2.Na/c20-15-10-16(22-5-21-15)26(6-23-10)18-11(29)13(7(3-27)38-18)41-43(35,36)37-4-8-14(40-42(32,33)34)12(30)17(39-8)25-2-1-9(28)24-19(25)31;/h1-2,5-8,11-14,17-18,27,29-30H,3-4H2,(H,35,36)(H2,20,21,22)(H,24,28,31)(H2,32,33,34)
• InChIKey: GAPYXTQZKWZNFQ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: [(2-{[({[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}(hydroxy)phosphoryl)oxy]methyl}-5-(2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)-4-hydroxyoxolan-3-yl)oxy]phosphonic acid sodium
• IUPAC Traditional name: {2-[({[5-(6-aminopurin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy(hydroxy)phosphoryl}oxy)methyl]-5-(2,4-dioxo-3H-pyrimidin-1-yl)-4-hydroxyoxolan-3-yl}oxyphosphonic acid sodium
• Synonyms: Adenylyl(3′→5′)uridine 3′-monophosphate sodium salt

Database IDs

• CAS Number: 147202-92-4
• MDL Number: MFCD00078870
• PubChem SID: 162225616
• PubChem CID: 71308420

CALCULATED PROPERTIES

• Acid pKa: 0.8262656
• H Acceptors: 16
• H Donor: 8
• LogD (pH = 5.5): -8.824663
• LogD (pH = 7.4): -10.069655
• Log P: -6.224255
• Molar Refractivity: 133.728 cm^3
• Polarizability: 53.401276 Å^3
• Polar Surface Area: 320.7 Å^2
• Rotatable Bonds: 10
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 22-26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

DETAILS

Sigma Aldrich - A4298

Biochem/physiol Actions
Found in nature bound to diphtheria toxin.
Preparation Note
Prepared by enzymatic hydrolysis of RNA.