6-(2-butanamido-6-oxo-6,9-dihydro-3H-purin-9-yl)-2-hydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-7-yl butanoate sodium

• ChemBase ID: 133692
• Molecular Formular: C18H24N5NaO9P
• Molecular Mass: 508.374791
• Monoisotopic Mass: 508.12093328
• SMILES: CCCC(=O)Nc1[nH]c2c(c(=O)n1)ncn2C1C(C2C(O1)COP(=O)(O2)O)OC(=O)CCC.[Na]
• Canonical SMILES: CCCC(=O)OC1C2OP(=O)(O)OCC2OC1n1cnc2c1[nH]c(NC(=O)CCC)nc2=O.[Na]
• InChI: InChI=1S/C18H24N5O9P.Na/c1-3-5-10(24)20-18-21-15-12(16(26)22-18)19-8-23(15)17-14(31-11(25)6-4-2)13-9(30-17)7-29-33(27,28)32-13;/h8-9,13-14,17H,3-7H2,1-2H3,(H,27,28)(H2,20,21,22,24,26)
• InChIKey: NYJYLSMMHGCJLV-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-(2-butanamido-6-oxo-6,9-dihydro-3H-purin-9-yl)-2-hydroxy-2-oxo-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-7-yl butanoate sodium
• IUPAC Traditional name: 6-(2-butanamido-6-oxo-3H-purin-9-yl)-2-hydroxy-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-7-yl butanoate sodium
• Synonyms: N2,2′-O-Dibutyrylguanosine 3′,5′-cyclic monophosphate sodium salt hydrate

Database IDs

• CAS Number: 51116-00-8
• EC Number: 256-992-2
• MDL Number: MFCD00038422
• PubChem SID: 162227969; 24893759
• PubChem CID: 16219237

CALCULATED PROPERTIES

• Acid pKa: 1.7591121
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -1.116082
• LogD (pH = 7.4): -1.5051824
• Log P: 0.31648433
• Molar Refractivity: 108.3327 cm^3
• Polarizability: 42.759457 Å^3
• Polar Surface Area: 179.67 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL
• Apperance: off-white 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: ≥95% (HPLC)

DETAILS

Sigma Aldrich - D3510

Biochem/physiol Actions
Cell permeable, cGMP analog that activates protein kinase G. Has been shown to increase intracellular calcium concentration in neurons and hepatocytes. Inhibits thrombin-induced arachidonic acid release in platelets. Increases endothelial P-selectin expression via activation of protein kinase G. Used to study the activation of p38 mitogen-activated protein kinase by lipopolysaccharide in neutrophils.