sodium [(2S,4aR,6R,7R,7aS)-6-(5,6-dichloro-1H-1,3-benzodiazol-1-yl)-7-hydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-yl]sulfanide

• ChemBase ID: 153189
• Molecular Formular: C12H10Cl2N2NaO5PS
• Molecular Mass: 419.152731
• Monoisotopic Mass: 417.9322787
• SMILES: c1c2c(cc(c1Cl)Cl)n(cn2)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)[S-])O.[Na+]
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)([S-])OC[C@H]2O[C@H]1n1cnc2c1cc(Cl)c(c2)Cl.[Na+]
• InChI: InChI=1S/C12H11Cl2N2O5PS.Na/c13-5-1-7-8(2-6(5)14)16(4-15-7)12-10(17)11-9(20-12)3-19-22(18,23)21-11;/h1-2,4,9-12,17H,3H2,(H,18,23);/q;+1/p-1/t9-,10-,11-,12-,22+;/m1./s1
• InChIKey: LXTHVPHQPNCKKG-OIMJWDEGSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium [(2S,4aR,6R,7R,7aS)-6-(5,6-dichloro-1H-1,3-benzodiazol-1-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 [(2S,4aR,6R,7R,7aS)-6-(5,6-dichloro-1,3-benzodiazol-1-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: 5,6-Dichloro-1-b-D-ribofuranosylbenzimidazole-3′,5′-cyclic monophosphorothioate, Sp- isomer sodium salt; Sp 5,6-DCl-cBIMPS

Database IDs

• CAS Number: 120912-54-1
• MDL Number: MFCD06795834
• PubChem SID: 162247328; 24724615
• PubChem CID: 23675379

CALCULATED PROPERTIES

• Acid pKa: 0.9692167
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 0.7207854
• LogD (pH = 7.4): 0.88058496
• Log P: 0.07400952
• Molar Refractivity: 85.1375 cm^3
• Polarizability: 35.845493 Å^3
• Polar Surface Area: 82.81 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: freely soluble; ethanol: freely soluble; H2O: soluble1 mM
• Apperance: white solid

Safety Information

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

Product Information

• Purity: ≥98% (HPLC)
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C12H10Cl2N2O5PSNa

DETAILS

Sigma Aldrich - S6069

Biochem/physiol Actions
Selective cAMP-dependent protein kinase (PKA) activator. Especially suitable for intact cells showing preference for site B of type II isozyme. Completely stable against mammalian cPDE types I & III and only extremely slowly hydrolized by cPDE type II. Surpasses the widely used but problematic dibutyryl cAMP or 8-CPT-cAMP in terms of metabolic stability, membrane permeability and potency.