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

• ChemBase ID: 156148
• Molecular Formular: C18H26BrN5NaO11P
• Molecular Mass: 622.293471
• Monoisotopic Mass: 621.04474959
• SMILES: CCCC(=O)Nc1[nH]c(=O)c2c(n1)n(c(n2)Br)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)[O-])OC(=O)CCC.O.[Na+].O
• Canonical SMILES: CCCC(=O)O[C@@H]1[C@@H]2OP(=O)([O-])OC[C@H]2O[C@H]1n1c(Br)nc2c1nc(NC(=O)CCC)[nH]c2=O.O.O.[Na+]
• InChI: InChI=1S/C18H23BrN5O9P.Na.2H2O/c1-3-5-9(25)20-18-22-14-11(15(27)23-18)21-17(19)24(14)16-13(32-10(26)6-4-2)12-8(31-16)7-30-34(28,29)33-12;;;/h8,12-13,16H,3-7H2,1-2H3,(H,28,29)(H2,20,22,23,25,27);;2*1H2/q;+1;;/p-1/t8-,12-,13-,16-;;;/m1.../s1
• InChIKey: OAYGQEGFWDXWTN-AVZZNAHOSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4aR,6R,7R,7aR)-6-(8-bromo-2-butanamido-6-oxo-6,9-dihydro-1H-purin-9-yl)-7-(butanoyloxy)-2-oxo-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate dihydrate
• IUPAC Traditional name: sodium (4aR,6R,7R,7aR)-6-(8-bromo-2-butanamido-6-oxo-1H-purin-9-yl)-7-(butanoyloxy)-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate dihydrate
• Synonyms: N2,2′-O-Dibutyrylguanosine 3′,5′-cyclic monophosphate sodium salt dihydrate

Database IDs

• CAS Number: 51116-00-8
• EC Number: 256-992-2
• MDL Number: MFCD00150552
• Beilstein Number: 6264591
• PubChem SID: 162250286
• PubChem CID: 71312274

CALCULATED PROPERTIES

• Acid pKa: 1.8325742
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -0.56135046
• LogD (pH = 7.4): -0.5922815
• Log P: 1.7935967
• Molar Refractivity: 115.2692 cm^3
• Polarizability: 45.599205 Å^3
• Polar Surface Area: 182.5 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, colorless

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: ≥96% (HPLC)
• Impurities: ≤0.2% cGMP; ≤0.5% N(2)-monobutyrylguanosine-3′,5′-cyclophosphate; ≤1% dibutyrylguanosine-3′,5′-cyclophosphate; ≤2% 2′-O-monobutyrylguanosine-3′,5′-cyclophosphate
• Empirical Formula (Hill Notation): C18H23N5NaO9P · 2H2O

DETAILS

Sigma Aldrich - 34995

Other Notes
Inhibits agonist-induced secretion of amylase from isolated rat pancreatic acini1