(4aR,6R,7R,7aR)-6-(6-amino-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: 155671
• Molecular Formular: C14H18N5O6PS
• Molecular Mass: 415.361381
• Monoisotopic Mass: 415.07154095
• SMILES: CCCC(=O)O[C@@H]1[C@H]2[C@@H](COP(=S)(O2)O)O[C@H]1n1cnc2c1ncnc2N
• Canonical SMILES: CCCC(=O)O[C@@H]1[C@@H]2OP(=S)(O)OC[C@H]2O[C@H]1n1cnc2c1ncnc2N
• InChI: InChI=1S/C14H18N5O6PS/c1-2-3-8(20)24-11-10-7(4-22-26(21,27)25-10)23-14(11)19-6-18-9-12(15)16-5-17-13(9)19/h5-7,10-11,14H,2-4H2,1H3,(H,21,27)(H2,15,16,17)/t7-,10-,11-,14-,26?/m1/s1
• InChIKey: XSAXBAAZBXKFFH-IDYJAONBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6R,7R,7aR)-6-(6-amino-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: (4aR,6R,7R,7aR)-6-(6-aminopurin-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-2′-O-MB-cAMPS; Rp-2′-O-Monobutyryladenosine 3′,5′-cyclic monophosphorothioate

Database IDs

• CAS Number: 152218-23-0
• PubChem SID: 162249809
• PubChem CID: 44755106

CALCULATED PROPERTIES

• Acid pKa: 1.9570092
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): -1.2860287
• LogD (pH = 7.4): -1.2193222
• Log P: -1.4671748
• Molar Refractivity: 96.6598 cm^3
• Polarizability: 38.635265 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 (approx. 2 mg)
• Mol. Weight: apparent mol wt 437.3 Da

DETAILS

Sigma Aldrich - M5064

Application
Eliminates first messenger-stimulated phosphorylation by cyclic AMP-dependent protein kinase.