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

• ChemBase ID: 173031
• Molecular Formular: C18H18N6NaO8P
• Molecular Mass: 500.334451
• Monoisotopic Mass: 500.08214248
• SMILES: [C@H]1([C@H]2[C@@H](O[C@H]1n1c3c(nc1)c(=O)[nH]c(n3)N)COP(=O)(O2)[O-])OC(=O)c1c(cccc1)NC.[Na+]
• Canonical SMILES: CNc1ccccc1C(=O)O[C@@H]1[C@@H]2OP(=O)([O-])OC[C@@H]2O[C@H]1n1cnc2c1nc(N)[nH]c2=O.[Na+]
• InChI: InChI=1S/C18H19N6O8P.Na/c1-20-9-5-3-2-4-8(9)17(26)31-13-12-10(6-29-33(27,28)32-12)30-16(13)24-7-21-11-14(24)22-18(19)23-15(11)25;/h2-5,7,10,12-13,16,20H,6H2,1H3,(H,27,28)(H3,19,22,23,25);/q;+1/p-1/t10-,12-,13-,16-;/m1./s1
• InChIKey: YSPAKCFRSSBJJK-KHXPSBENSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4aR,6R,7R,7aR)-6-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-7-[2-(methylamino)benzoyloxy]-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,7aR)-6-(2-amino-6-oxo-1H-purin-9-yl)-7-[2-(methylamino)benzoyloxy]-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate
• Synonyms: Cyclic 3',5'-(hydrogen phosphate) 2'-[2-(methylamino)benzoate] Guanosine Monosodium Salt; MANT-cGMP; 2'-(N-Methylanthraniloyl) Guanosine 3',5'-Cyclic Monophosphate Sodium Salt

Database IDs

• CAS Number: 221905-46-0
• PubChem SID: 164228941
• PubChem CID: 44755111

CALCULATED PROPERTIES

• Acid pKa: 1.8095231
• H Acceptors: 9
• H Donor: 3
• LogD (pH = 5.5): -1.6385119
• LogD (pH = 7.4): -1.6914799
• Log P: 0.22178479
• Molar Refractivity: 110.6091 cm^3
• Polarizability: 41.973526 Å^3
• Polar Surface Area: 191.45 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Pale Yellow Solid

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - M288250

A blue fluorescent derivative of cGMP is a useful substrate the assay of cyclic nucleotide phosphdiesterase. Also inhibits calmodulin-dependent activation of cyclic nucleotide phosphodiesterase by peptide segments of HIV envelope glycoproteins has been m

REFERENCES

• J. Biol. Chem., 257, 13354 (1982)
• Anal. Biochem., 162, 291 (1982)
• J. Biol. Chem., 270, 22277 (1993)