(2R,4aR,6R,7R,7aR)-6-(6-amino-8-bromo-9H-purin-9-yl)-2-hydroxy-2-sulfanylidene-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-7-yl butanoate

• ChemBase ID: 155659
• Molecular Formular: C14H17BrN5O6PS
• Molecular Mass: 494.257441
• Monoisotopic Mass: 492.98205292
• SMILES: CCCC(=O)O[C@@H]1[C@H]2[C@@H](COP(=S)(O2)O)O[C@H]1n1c2c(c(ncn2)N)nc1Br
• Canonical SMILES: CCCC(=O)O[C@@H]1[C@@H]2OP(=S)(O)OC[C@H]2O[C@H]1n1c(Br)nc2c1ncnc2N
• InChI: InChI=1S/C14H17BrN5O6PS/c1-2-3-7(21)25-10-9-6(4-23-27(22,28)26-9)24-13(10)20-12-8(19-14(20)15)11(16)17-5-18-12/h5-6,9-10,13H,2-4H2,1H3,(H,22,28)(H2,16,17,18)/t6-,9-,10-,13-,27-/m1/s1
• InChIKey: KWTXVSKODFLFLA-WJCFKVOZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4aR,6R,7R,7aR)-6-(6-amino-8-bromo-9H-purin-9-yl)-2-hydroxy-2-sulfanylidene-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-7-yl butanoate
• IUPAC Traditional name: (2R,4aR,6R,7R,7aR)-6-(6-amino-8-bromopurin-9-yl)-2-hydroxy-2-sulfanylidene-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-7-yl butanoate
• Synonyms: Rp-8-Br-MB-cAMPS; 8-Bromo-2′-monobutyryladenosine-3′,5′-cyclic monophosphorothioate, Rp-isomer

Database IDs

• MDL Number: MFCD04113730
• PubChem SID: 162249797
• PubChem CID: 44755028

CALCULATED PROPERTIES

• Acid pKa: 1.6879934
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -0.15005212
• LogD (pH = 7.4): -0.15416987
• Log P: -0.029581845
• Molar Refractivity: 104.2846 cm^3
• Polarizability: 41.70676 Å^3
• Polar Surface Area: 143.84 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: solid

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: >97% (HPLC)
• Packaging: vial of 5 μmol (2.5 mg solid)
• Empirical Formula (Hill Notation): C14H16BrN5O6PSNa

DETAILS

Sigma Aldrich - B2557

Application
Lipophilic precursor that is more lipophilic and membrane-permeable compared to Rp-8-Br-cAMPS.