sodium (4aR,6R,7R,7aS)-6-{6-amino-8-[(4-chlorophenyl)sulfanyl]-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: 105130
• Molecular Formular: C16H14ClN5NaO6PS
• Molecular Mass: 493.793791
• Monoisotopic Mass: 492.99886278
• SMILES: [Na+].Nc1ncnc2c1nc(Sc1ccc(Cl)cc1)n2[C@@H]1O[C@@H]2COP(=O)([O-])O[C@H]2[C@H]1O
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)([O-])OC[C@H]2O[C@H]1n1c(Sc2ccc(cc2)Cl)nc2c1ncnc2N.[Na+]
• InChI: InChI=1S/C16H15ClN5O6PS.Na/c17-7-1-3-8(4-2-7)30-16-21-10-13(18)19-6-20-14(10)22(16)15-11(23)12-9(27-15)5-26-29(24,25)28-12;/h1-4,6,9,11-12,15,23H,5H2,(H,24,25)(H2,18,19,20);/q;+1/p-1/t9-,11-,12-,15-;/m1./s1
• InChIKey: YIJFVHMIFGLKQL-DNBRLMRSSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4aR,6R,7R,7aS)-6-{6-amino-8-[(4-chlorophenyl)sulfanyl]-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 (4aR,6R,7R,7aS)-6-{6-amino-8-[(4-chlorophenyl)sulfanyl]purin-9-yl}-7-hydroxy-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate
• Synonyms: 8-(4-Chlorophenylthio)adenosine 3′:5′-cyclic monophosphate sodium salt; 8-CPT cAMP; 8-(4-CHLOROPHENYLTHIO) ADENOSINE-3',5'-cyclic-MONOPHOSPHATE SODIUM SALT; pCPT-cAMP; 8-(4-Chlorophenylthio)adenosine 3′,5′-cyclic monophosphate sodium salt

Database IDs

• CAS Number: 93882-12-3; 41941-66-6
• EC Number: 299-413-9
• MDL Number: MFCD00057683
• PubChem SID: 24278024; 162092169
• PubChem CID: 23672705

CALCULATED PROPERTIES

• LogD (pH = 7.4): -0.21795417
• Log P: -0.46497026
• Molar Refractivity: 106.13 cm^3
• Polarizability: 42.209587 Å^3
• Polar Surface Area: 157.67 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true
• Acid pKa: 1.8322334
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -0.2596107

PROPERTIES

Physical Property

• Solubility: H2O: soluble25 mg/mL
• Apperance: white powder

Safety Information

• Storage Condition: 0°C
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Pharmacology Properties

• Gene Information: human ... PRKAR1A(5573), PRKAR1AP(5574), PRKAR1B(5575), PRKAR2A(5576), PRKAR2B(5577)

Product Information

• Purity: ≥97.0% (HPLC)

DETAILS

MP Biomedicals - 02158891

Sodium Salt
cAMP analog which activates cAMP- and cGMP- dependent protein kinase.

Sigma Aldrich - C3912

Biochem/physiol Actions
Membrane permeable cAMP analog. Used as a selective activator of cAMP dependent protein kinase (PKA). Inhibits cGMP-dependent phosphodiesterase and, at higher concentrations, inhibits cAMP-dependent phosphodiesterase. Inhibits phosphoinositide hydrolysis and secretion stimulated by n-formyl-Met-Leu-Phe but not platelet-activating factor in leukocytes. Renders HL-60 cells more resistant to NO-induced DNA damage.

REFERENCES

• Sandberg, M., et.al., Biochem. J. , 279 : 521 (1991).