sodium (2R,4aR,6R,7R,7aS)-6-{2-bromo-9-oxo-6-phenyl-3H,4H,9H-imidazo[1,2-a]purin-3-yl}-7-hydroxy-2-sulfanylidene-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-olate hydrate

• ChemBase ID: 154110
• Molecular Formular: C18H16BrN5NaO7PS
• Molecular Mass: 580.281471
• Monoisotopic Mass: 578.95891179
• SMILES: c1ccc(cc1)c1cn2c(=O)c3c([nH]c2n1)n(c(n3)Br)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=S)(O2)[O-])O.O.[Na+]
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=S)([O-])OC[C@H]2O[C@H]1n1c(Br)nc2c1[nH]c1nc(cn1c2=O)c1ccccc1.O.[Na+]
• InChI: InChI=1S/C18H15BrN5O6PS.Na.H2O/c19-17-21-11-14(24(17)16-12(25)13-10(29-16)7-28-31(27,32)30-13)22-18-20-9(6-23(18)15(11)26)8-4-2-1-3-5-8;;/h1-6,10,12-13,16,25H,7H2,(H,20,22)(H,27,32);;1H2/q;+1;/p-1/t10-,12-,13-,16-,31-;;/m1../s1
• InChIKey: PNUXBFRWMZKKAJ-IIULARJUSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2R,4aR,6R,7R,7aS)-6-{2-bromo-9-oxo-6-phenyl-3H,4H,9H-imidazo[1,2-a]purin-3-yl}-7-hydroxy-2-sulfanylidene-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate hydrate
• IUPAC Traditional name: sodium (2R,4aR,6R,7R,7aS)-6-{2-bromo-9-oxo-6-phenyl-4H-imidazo[1,2-a]purin-3-yl}-7-hydroxy-2-sulfanylidene-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate hydrate
• Synonyms: Rp-β-Phenyl-1,N2-etheno-8-bromoguanosine 3′,5′-cyclic monophosphorothioate sodium salt; Rp-8-Br-PET-cGMPS; Rp-8-Bromo-β-phenyl-1,N2-ethenoguanosine 3′,5′-cyclic monophosphorothioate sodium salt

Database IDs

• CAS Number: 185246-32-6
• PubChem SID: 24724424; 162248249
• PubChem CID: 23695925

CALCULATED PROPERTIES

• Acid pKa: 1.4283798
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 1.6683608
• LogD (pH = 7.4): 1.6599017
• Log P: 3.8667405
• Molar Refractivity: 115.6396 cm^3
• Polarizability: 47.310707 Å^3
• Polar Surface Area: 135.72 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble15 mg/mL at ≤60 °C
• Apperance: white to beige powder
• Melting Point: 240-300 °C(lit.)

Safety Information

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

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C18H14BrN5NaO6PS

DETAILS

Sigma Aldrich - B6684

Packaging
Hygroscopic, store under argon
Legal Information
U.S. Patent 5,625,056, DE Patent 4,217,679.
Biochem/physiol Actions
Rp-8-Br-PET-cGMPS is metabolically stable, competitive inhibitor of cGMP-dependent protein kinase G. Inhibits both PKG I (Ki = 30 nM) and PKG II and blocks cGMP-gated retinal type ion channels (IC50 = 25 micromoles).