4-(6-amino-9H-purin-9-yl)-2-hydroxy-6-(hydroxymethyl)-tetrahydro-2H-1,3,5,2λ5-furo[3,4-d][1,3,2λ5]dioxaphosphol-2-one sodium

• ChemBase ID: 133872
• Molecular Formular: C10H12N5NaO6P
• Molecular Mass: 352.195711
• Monoisotopic Mass: 352.04228904
• SMILES: c1nc(c2c(n1)n(cn2)C1C2C(C(O1)CO)OP(=O)(O2)O)N.[Na]
• Canonical SMILES: OCC1OC(C2C1OP(=O)(O2)O)n1cnc2c1ncnc2N.[Na]
• InChI: InChI=1S/C10H12N5O6P.Na/c11-8-5-9(13-2-12-8)15(3-14-5)10-7-6(4(1-16)19-10)20-22(17,18)21-7;/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13)
• InChIKey: PVZCZFXKKKFWBD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-(6-amino-9H-purin-9-yl)-2-hydroxy-6-(hydroxymethyl)-tetrahydro-2H-1,3,5,2λ^5-furo[3,4-d][1,3,2λ^5]dioxaphosphol-2-one sodium
• IUPAC Traditional name: 4-(6-aminopurin-9-yl)-2-hydroxy-6-(hydroxymethyl)-tetrahydro-1,3,5,2λ^5-furo[3,4-d][1,3,2λ^5]dioxaphosphol-2-one sodium
• Synonyms: 2′,3′-cAMP sodium salt; Adenosine 2′:3′-cyclic monophosphate sodium salt; 腺苷 2′:3′-循环磷酸钠盐 钠盐

Database IDs

• CAS Number: 37063-35-7
• EC Number: 253-328-3
• MDL Number: MFCD00005757
• PubChem SID: 162228149; 24891439
• PubChem CID: 16218990

CALCULATED PROPERTIES

• Acid pKa: 1.7586845
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -3.771956
• LogD (pH = 7.4): -3.695558
• Log P: -4.0625772
• Molar Refractivity: 70.2895 cm^3
• Polarizability: 27.912537 Å^3
• Polar Surface Area: 154.84 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

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

Product Information

• Purity: ≥97%

DETAILS

Sigma Aldrich - A9376

Caution
Caution: Do not confuse with the common adenosine 2′(3′)-monophosphate (mixed isomers).
Application
Adenosine 2′,3′-cyclic monophosphate (2′,3′-cAMP) is believed to serve as an extracellular source of adenosine. The release of extracellular 2′,3′-cAMP occurs in response to injury. 2′,3′-cAMP may be used to study the distribution and specificity of its degrading enzymes in the context of unique biological activities. 2′,3′-cAMP may also be used to study apoptosis induced at the level of mitochondrial permeability transition pores. 2′,3′-cAMP is converted into 2′-AMP and 3′-AMP which inhibit proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors.