sodium (4aR,6R,7R,7aS)-6-(2-amino-8-bromo-6-oxo-6,9-dihydro-1H-purin-9-yl)-7-hydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-olate

• ChemBase ID: 131320
• Molecular Formular: C10H10BrN5NaO7P
• Molecular Mass: 446.083231
• Monoisotopic Mass: 444.9398906
• SMILES: C1[C@@H]2[C@H]([C@H]([C@@H](O2)n2c3c(c(=O)[nH]c(n3)N)nc2Br)O)OP(=O)(O1)[O-].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)([O-])OC[C@H]2O[C@H]1n1c(Br)nc2c1nc(N)[nH]c2=O.[Na+]
• InChI: InChI=1S/C10H11BrN5O7P.Na/c11-9-13-3-6(14-10(12)15-7(3)18)16(9)8-4(17)5-2(22-8)1-21-24(19,20)23-5;/h2,4-5,8,17H,1H2,(H,19,20)(H3,12,14,15,18);/q;+1/p-1/t2-,4-,5-,8-;/m1./s1
• InChIKey: ZJRFCXHKYQVNFK-YEOHUATISA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4aR,6R,7R,7aS)-6-(2-amino-8-bromo-6-oxo-6,9-dihydro-1H-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-(2-amino-8-bromo-6-oxo-1H-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-Br-cGMP; 8-Bromoguanosine-3′,5′-cyclomonophosphate sodium salt; 8-Bromo-cyclic GMP; 8-Bromoguanosine 3′,5′-cyclic monophosphate sodium salt

Database IDs

• CAS Number: 51116-01-9
• EC Number: 256-993-8
• MDL Number: MFCD00070128
• Beilstein Number: 8378760
• PubChem SID: 24278021; 162225598
• PubChem CID: 23702959

CALCULATED PROPERTIES

• Acid pKa: 1.9035653
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -3.215349
• LogD (pH = 7.4): -3.245903
• Log P: -1.1080263
• Molar Refractivity: 78.2181 cm^3
• Polarizability: 30.848368 Å^3
• Polar Surface Area: 173.35 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, slightly yellow; H2O: soluble50 mg/mL
• Apperance: powder

Safety Information

• 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); ≥99.0% (HPLC)
• Impurities: ≤1% guanosine 3′,5′-cyclophosphate (HPLC); ≤8% water(2 mol/mol)
• Empirical Formula (Hill Notation): C10H10BrN5NaO7P

DETAILS

Sigma Aldrich - B1381

Biochem/physiol Actions
Cell-permeable cGMP analog having greater resistance to hydrolysis by phosphodiesterases than cGMP. Activates cGMP-dependent protein kinase. Slows or inhibits the intracellular calcium oscillations of tracheal smooth muscle cells in response to acetylcholine. Reported to mimic the effect of nitric oxide generating drugs.

Sigma Aldrich - 17110

Other Notes
A membrane-permeable cGMP derivative. Induces HL-60 cells to differentiate along the granulocytic pathway1