{[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid sodium

• ChemBase ID: 133575
• Molecular Formular: C10H14N5NaO7P
• Molecular Mass: 370.210991
• Monoisotopic Mass: 370.05285372
• SMILES: c1nc(c2c(n1)n(cn2)C1C(C(C(O1)CO)OP(=O)(O)O)O)N.[Na]
• Canonical SMILES: OCC1OC(C(C1OP(=O)(O)O)O)n1cnc2c1ncnc2N.[Na]
• InChI: InChI=1S/C10H14N5O7P.Na/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(17)7(4(1-16)21-10)22-23(18,19)20;/h2-4,6-7,10,16-17H,1H2,(H2,11,12,13)(H2,18,19,20)
• InChIKey: VYSITLSPGMCELY-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[5-(6-amino-9H-purin-9-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid sodium
• IUPAC Traditional name: 3'-adenylic acid sodium
• Synonyms: 3′-AMP; Adenosine 3′-monophosphate sodium salt; 3′-腺苷酸; 腺苷-3′-磷酸 钠盐

Database IDs

• CAS Number: 4958-39-8
• MDL Number: MFCD00065985
• PubChem SID: 24890422; 162227852
• PubChem CID: 16218832

CALCULATED PROPERTIES

• Acid pKa: 0.8653417
• H Acceptors: 10
• H Donor: 5
• LogD (pH = 5.5): -4.829372
• LogD (pH = 7.4): -6.054201
• Log P: -5.274322
• Molar Refractivity: 74.0685 cm^3
• Polarizability: 29.089455 Å^3
• Polar Surface Area: 186.07 Å^2
• Rotatable Bonds: 4
• 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

• Biological Source: from Saccharomyces cerevisiae

DETAILS

Sigma Aldrich - A0386

Application
Adenosine 3′-monophosphate (3′-AMP) is a metabolite produced from hydrolysis of 2′,3′-cAMP by a family of metal-dependent phosphodiesterases. 3′-AMP inhibit proliferation of preglomerular vascular smooth muscle cells and glomerular mesangial cells via A2B receptors. 2′,3′-cAMP and 3′-AMP represent a new unexplored pathway for adenosine-based cell regulation.