sodium (4aR,6R,7R,7aS)-6-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-7-hydroxy-2-oxo-hexahydro(4,4a,6,7,7a-13C5)-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-olate

• ChemBase ID: 169804
• Molecular Formular: C10H11N5NaO7P
• Molecular Mass: 372.15044519
• Monoisotopic Mass: 372.04615282
• SMILES: [13C@H]1([13C@H]2[13C@@H](O[13C@H]1n1c3nc([nH]c(=O)c3nc1)N)[13CH2]OP(=O)(O2)[O-])O.[Na+]
• Canonical SMILES: O[13C@@H]1[13C@@H]2OP(=O)([O-])O[13CH2][13C@@H]2O[13C@H]1n1cnc2c1nc(N)[nH]c2=O.[Na+]
• InChI: InChI=1S/C10H12N5O7P.Na/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6;/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17);/q;+1/p-1/t3-,5-,6-,9-;/m1./s1/i1+1,3+1,5+1,6+1,9+1
• InChIKey: KMPIYXNEROUNOG-OBSDCYSMSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4aR,6R,7R,7aS)-6-(2-amino-6-oxo-6,9-dihydro-1H-purin-9-yl)-7-hydroxy-2-oxo-hexahydro(4,4a,6,7,7a-^1^3C₅)-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-6-oxo-1H-purin-9-yl)-7-hydroxy-2-oxo-tetrahydro(4,4a,6,7,7a-^1^3C₅)-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate
• Synonyms: Guanosine Cyclic 3',5'-(Hydrogen phosphate)-13C5 Sodium Salt; Cyclic 3',5'-Guanosine Monophosphate-13C5 Monosodium Salt; Guanosine Monophosphate-13C5 Monosodium Salt; Monosodium-GMP-13C5; Guanosine 3',5'-Cyclic Monophosphate-13C5 Sodium Salt

Database IDs

• PubChem SID: 162263936
• PubChem CID: 71317172

CALCULATED PROPERTIES

• Acid pKa: 2.0500584
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -4.2590003
• LogD (pH = 7.4): -4.309573
• Log P: -2.0959094
• Molar Refractivity: 70.5933 cm^3
• Polarizability: 27.621025 Å^3
• Polar Surface Area: 173.35 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - G837963

Labelled analogue of Guanosine 3’,5’-Cyclic Monophosphate, a substituted Guanosine having cyclic phosphodiesterase activity.

REFERENCES

• Tazawa, et al.: Biochemistry, 11, 4931 (1972)