sodium 6-(2-butanamido-6-oxo-6,9-dihydro-1H-purin-9-yl)-7-(butanoyloxy)-2-oxo-hexahydro-1,3,5,2$l^{5}-furo[3,2-d][1,3,2$l^{5}]dioxaphosphinin-2-olate

• ChemBase ID: 102914
• Molecular Formular: C18H23N5NaO9P
• Molecular Mass: 507.366851
• Monoisotopic Mass: 507.11310825
• SMILES: [Na+].CCCC(=O)Nc1nc2c(ncn2C2OC3COP(=O)([O-])OC3C2OC(=O)CCC)c(=O)[nH]1
• Canonical SMILES: CCCC(=O)OC1C2OP(=O)([O-])OCC2OC1n1cnc2c1nc(NC(=O)CCC)[nH]c2=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);/q;+1/p-1
• InChIKey: MGBPJXVWDGGLKI-UHFFFAOYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium 6-(2-butanamido-6-oxo-6,9-dihydro-1H-purin-9-yl)-7-(butanoyloxy)-2-oxo-hexahydro-1,3,5,2$l^{5}-furo[3,2-d][1,3,2$l^{5}]dioxaphosphinin-2-olate
• IUPAC Traditional name: potassium 6-(2-butanamido-6-oxo-1H-purin-9-yl)-7-(butanoyloxy)-2-oxo-tetrahydro-4H-1,3,5,2$l^{5}-furo[3,2-d][1,3,2$l^{5}]dioxaphosphinin-2-olate
• Synonyms: Dibutyryl-cGMP; N^2,2'-O-DIBUTYRYLGUANOSINE-3',5'-cyclic-MONOPHOSPHATE SODIUM SALT

Database IDs

• CAS Number: 51116-00-8
• EC Number: 256-992-2
• PubChem SID: 162089353
• PubChem CID: 44134671

CALCULATED PROPERTIES

• Acid pKa: 1.8493798
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -1.625391
• LogD (pH = 7.4): -1.6554657
• Log P: 0.57675856
• Molar Refractivity: 107.6444 cm^3
• Polarizability: 42.45612 Å^3
• Polar Surface Area: 182.5 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: 0°C

Product Information

• Purity: 96%

DETAILS

MP Biomedicals - 02105486

Sodium Salt
Purity: 96%
Activates cGMP-dependent protein kinase and inhibits thrombin induced arachidonic acid release in human platelets.

REFERENCES

• Meyer, R.B. and Miller, J.P., Life Sci. , 14 : 1019 (1974).
• Francis, S.G. et al., ibid. , 34 : 506 (1988).
• Schultz, K.D., et al., Naunyn-Schmiedeberg's Arch. Pharmacol. , 306 : 1 (1979).
• Sane, D.C, et al., Biochem. Biophys. Res. Commun. , 165 : 708 (1989).