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-yl]sulfanide

• ChemBase ID: 153115
• Molecular Formular: C16H14ClN5NaO5PS2
• Molecular Mass: 509.859391
• Monoisotopic Mass: 508.97601916
• SMILES: c1cc(ccc1Sc1nc2c(ncnc2n1[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)[S-])O)N)Cl.[Na+]
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)([S-])OC[C@H]2O[C@H]1n1c(Sc2ccc(cc2)Cl)nc2c1ncnc2N.[Na+]
• InChI: InChI=1S/C16H15ClN5O5PS2.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(26-15)5-25-28(24,29)27-12;/h1-4,6,9,11-12,15,23H,5H2,(H,24,29)(H2,18,19,20);/q;+1/p-1/t9-,11-,12-,15-,28?;/m1./s1
• InChIKey: AWXMSJRRXLCVMW-JVSRKQJHSA-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-yl]sulfanide
• 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-yl]sulfanide
• Synonyms: 8-(4-Chlorophenylthio)adenosine-3′,5′-cyclic monophosphorothioate, Sp-isomer sodium salt; Sp-8-pCPT-cAMPS; Rp-8-CPT-cAMPS; 8-(4-Chlorophenylthio)adenosine-3′,5′-cyclic Monophosphorothioate, Rp-isomer sodium salt

Database IDs

• CAS Number: 129735-01-9; 129693-13-6(freeacid)
• MDL Number: MFCD04113743
• PubChem SID: 24724452; 24892271; 162247255
• PubChem CID: 23679060

CALCULATED PROPERTIES

• Acid pKa: 0.969233
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 1.2860775
• LogD (pH = 7.4): 1.3606073
• Log P: -0.10013322
• Molar Refractivity: 114.1209 cm^3
• Polarizability: 45.27169 Å^3
• Polar Surface Area: 134.61 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: >1 mg/mL
• Apperance: solid

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C; -70°C

Product Information

• Purity: >99% (HPLC); ≥98% (HPLC)
• Packaging: vial of 5 μmol
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C16H14ClN5O5PS2Na

DETAILS

Sigma Aldrich - C0735

Biochem/physiol Actions
Lipophilic analog of the competitive inhibitor of protein kinase A (cyclic AMP antagonist).

Sigma Aldrich - C8990

Biochem/physiol Actions
Selective cAMP-dependent protein kinase (PKA) activator.