sodium (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-olate

• ChemBase ID: 102912
• Molecular Formular: C10H11N5NaO6P
• Molecular Mass: 351.187771
• Monoisotopic Mass: 351.03446401
• SMILES: c1nc(c2c(n1)n(cn2)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)[O-])O)N.[Na+]
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)([O-])OC[C@H]2O[C@H]1n1cnc2c1ncnc2N.[Na+]
• InChI: InChI=1S/C10H12N5O6P.Na/c11-8-5-9(13-2-12-8)15(3-14-5)10-6(16)7-4(20-10)1-19-22(17,18)21-7;/h2-4,6-7,10,16H,1H2,(H,17,18)(H2,11,12,13);/q;+1/p-1/t4-,6-,7-,10-;/m1./s1
• InChIKey: BXJBFCKTIWRKMQ-MCDZGGTQSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (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-olate
• IUPAC Traditional name: sodium 3',5'-cyclic amp anion
• Synonyms: cAMP-Na; Adenosine 3′,5′-cyclic monophosphate sodium salt monohydrate; Adenosine-3',5'-Monophosphoric Acid; ADENOSINE-3',5'-cyclic-MONOPHOSPHATE SODIUM SALT; Adenosine Cyclic 3',5'-(Hydrogen Phosphate) Monosodium Salt; 3',5'-AMP Sodium Salt; Adenosine 3',5'-Phosphoric Acid Sodium Salt; Cyclic 3',5'-AMP Sodium Salt; Cyclic 3',5'-Adenosine Monophosphate Monosodium Salt; Cyclic AMP Sodium; Cyclic AMP Sodium Salt; cAMP Sodium Salt; Adenosine-3',5'-cyclic Monophosphate Sodium Salt; 3′,5′-Cyclic AMP sodium salt; 环化腺苷酸 钠盐; 腺苷-3′,5′-环单磷酸 钠盐 一水合物

Database IDs

• CAS Number: 37839-81-9
• MDL Number: MFCD00069736
• Beilstein Number: 54612
• PubChem SID: 162088780; 24891151
• PubChem CID: 23669773

CALCULATED PROPERTIES

• Acid pKa: 1.8324043
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -3.768807
• LogD (pH = 7.4): -3.6955175
• Log P: -4.0200067
• Molar Refractivity: 69.1678 cm^3
• Polarizability: 27.794725 Å^3
• Polar Surface Area: 157.67 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL; H2O: soluble50 mg/mL, clear, colorless
• Apperance: white powder

Safety Information

• Storage Condition: 0°C
• RTECS: AU7357900
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ~98%; ≥98.0% (HPLC); ≥99.0% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C10H11N5NaO6P · H2O

DETAILS

MP Biomedicals - 02105460

Sodium Salt
Crystalline
Purity: Approx. 98%

Sigma Aldrich - A6885

Application
Adenosine-3′,5′-cyclic monophosphate (cAMP) is an activator of cyclic-AMP-dependent protein kinase A (PKA). The cAMP/PKA signaling pathway has been shown to inhibit cell proliferation, induce differentiation and lead to apoptosis. Exogneous cAMP plays a role in the spontaneous activity and contraction of the heart muscle.
Biochem/physiol Actions
Naturally-occurring activator of cyclic-AMP-dependent protein kinase (PKA). cAMP is an important second messenger that is linked in many systems to neurotransmitter- or hormone-induced receptor stimulation. The cAMP/PKA signaling pathway has been shown to inhibit cell proliferation, induce differentiation and lead to apoptosis.

Sigma Aldrich - 01894

Biochem/physiol Actions
Naturally-occurring activator of cyclic-AMP-dependent protein kinase (PKA). cAMP is an important second messenger that is linked in many systems to neurotransmitter- or hormone-induced receptor stimulation. The cAMP/PKA signaling pathway has been shown to inhibit cell proliferation, induce differentiation and lead to apoptosis.

Toronto Research Chemicals - A280455

Adenosine-3’,5’-cyclic Monophosphate is an Adenosine (A280400) derivative useful as anticancer agent.

REFERENCES

• Keast, R., et al.: Pharma. Res., 19, 1019 (2002)