{[(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-7-hydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-yl]oxy}methyl acetate

• ChemBase ID: 155657
• Molecular Formular: C13H16N5O8P
• Molecular Mass: 401.268601
• Monoisotopic Mass: 401.07364913
• SMILES: CC(=O)OCOP1(=O)OC[C@@H]2[C@@H](O1)[C@H]([C@@H](O2)n1cnc2c1ncnc2N)O
• Canonical SMILES: CC(=O)OCOP1(=O)OC[C@@H]2[C@@H](O1)[C@@H](O)[C@@H](O2)n1cnc2c1ncnc2N
• InChI: InChI=1S/C13H16N5O8P/c1-6(19)22-5-24-27(21)23-2-7-10(26-27)9(20)13(25-7)18-4-17-8-11(14)15-3-16-12(8)18/h3-4,7,9-10,13,20H,2,5H2,1H3,(H2,14,15,16)/t7-,9-,10-,13-,27?/m1/s1
• InChIKey: USKCKKDBQFHVEK-OQEAWBJFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(4aR,6R,7R,7aS)-6-(6-amino-9H-purin-9-yl)-7-hydroxy-2-oxo-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-yl]oxy}methyl acetate
• IUPAC Traditional name: {[(4aR,6R,7R,7aS)-6-(6-aminopurin-9-yl)-7-hydroxy-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-yl]oxy}methyl acetate
• Synonyms: cAMP AM; Adenosine 3′,5′-cyclic monophosphate acetoxymethyl ester

Database IDs

• CAS Number: 159764-93-9
• MDL Number: MFCD03452647
• PubChem SID: 162249795
• PubChem CID: 71312192

CALCULATED PROPERTIES

• Acid pKa: 12.550381
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.1940618
• LogD (pH = 7.4): -1.0805722
• Log P: -1.078907
• Molar Refractivity: 85.0251 cm^3
• Polarizability: 34.507854 Å^3
• Polar Surface Area: 170.14 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: >97% (HPLC)
• Packaging: pkg of 1 μmol
• Empirical Formula (Hill Notation): C13H16N5O8P

DETAILS

Sigma Aldrich - A2224

Biochem/physiol Actions
Membrane-permeable precursor of the second messenger cyclic AMP