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

• ChemBase ID: 156115
• Molecular Formular: C18H25N5NaO9P
• Molecular Mass: 509.382731
• Monoisotopic Mass: 509.12875832
• SMILES: CCCC(=O)Nc1c2c(ncn1)n(cn2)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)[O-])OC(=O)CCC.O.[Na+]
• Canonical SMILES: CCCC(=O)O[C@@H]1[C@@H]2OP(=O)([O-])OC[C@H]2O[C@H]1n1cnc2c1ncnc2NC(=O)CCC.O.[Na+]
• InChI: InChI=1S/C18H24N5O8P.Na.H2O/c1-3-5-11(24)22-16-13-17(20-8-19-16)23(9-21-13)18-15(30-12(25)6-4-2)14-10(29-18)7-28-32(26,27)31-14;;/h8-10,14-15,18H,3-7H2,1-2H3,(H,26,27)(H,19,20,22,24);;1H2/q;+1;/p-1/t10-,14-,15-,18-;;/m1../s1
• InChIKey: MBIUSAASWSOYGU-VMZSDVDQSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4aR,6R,7R,7aR)-6-(6-butanamido-9H-purin-9-yl)-7-(butanoyloxy)-2-oxo-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate hydrate
• IUPAC Traditional name: sodium (4aR,6R,7R,7aR)-6-(6-butanamidopurin-9-yl)-7-(butanoyloxy)-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate hydrate
• Synonyms: Bucladesine; Dibutyryl cyclic-AMP; N6,2′-O-Dibutyryladenosine 3′,5′-cyclic monophosphate sodium salt monohydrate; 二丁酰环磷腺苷; 布拉地新; N6,2′-O-二丁酰基腺苷3′,5′-环磷酸 钠盐 一水合物

Database IDs

• CAS Number: 16980-89-5
• EC Number: 241-059-4
• MDL Number: MFCD00149371
• Beilstein Number: 6264305
• PubChem SID: 162250253
• PubChem CID: 23666343

CALCULATED PROPERTIES

• Acid pKa: 1.8274206
• H Acceptors: 8
• H Donor: 1
• LogD (pH = 5.5): -0.8815789
• LogD (pH = 7.4): -0.89628386
• Log P: -0.48056093
• Molar Refractivity: 106.9377 cm^3
• Polarizability: 42.676678 Å^3
• Polar Surface Area: 166.82 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble0.1 g/mL, clear, colorless; H2O: soluble0.1 g/mL, clear, colorless to faintly yellow

Safety Information

• RTECS: ES5055500
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥96.0% (HPLC); ≥97.0% (HPLC)
• Empirical Formula (Hill Notation): C18H23N5NaO8P · H2O

DETAILS

Sigma Aldrich - 34988

Other Notes
Studies on the cAMP-mediated down-regulation of the β2-adrenergic receptor1