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

• ChemBase ID: 155670
• Molecular Formular: C10H12N5O6PS
• Molecular Mass: 361.270941
• Monoisotopic Mass: 361.02459076
• SMILES: c1nc(c2c(n1)n(c(n2)O)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)S)O)N
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)(S)OC[C@H]2O[C@H]1n1c(O)nc2c1ncnc2N
• InChI: InChI=1S/C10H12N5O6PS/c11-7-4-8(13-2-12-7)15(10(17)14-4)9-5(16)6-3(20-9)1-19-22(18,23)21-6/h2-3,5-6,9,16H,1H2,(H,14,17)(H,18,23)(H2,11,12,13)/t3-,5-,6-,9-,22-/m1/s1
• InChIKey: ZJLRJSRRXWDPOZ-KVBUDSETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4aR,6R,7R,7aS)-6-(6-amino-8-hydroxy-9H-purin-9-yl)-7-hydroxy-2-sulfanyl-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-one
• IUPAC Traditional name: (2R,4aR,6R,7R,7aS)-6-(6-amino-8-hydroxypurin-9-yl)-7-hydroxy-2-sulfanyl-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-one
• Synonyms: 8-Hydroxyadenosine-3′,5′-monophosphorothioate, Rp-isomer

Database IDs

• PubChem SID: 162249808
• PubChem CID: 44755099

CALCULATED PROPERTIES

• Acid pKa: 0.9691424
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -1.7826015
• LogD (pH = 7.4): -1.735401
• Log P: -3.0600877
• Molar Refractivity: 75.7349 cm^3
• Polarizability: 31.172588 Å^3
• Polar Surface Area: 154.84 Å^2
• Rotatable Bonds: 1
• 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: >99% (HPLC)
• Packaging: vial of 1 μmol (approx. 0.4mg)
• Mol. Weight: mol wt 390.26
• Empirical Formula (Hill Notation): C10H11N5O6PSNa

DETAILS

Sigma Aldrich - H2161

Biochem/physiol Actions
Phosphodiesterase-resistant, polar, membrane-impermeable inhibitor of cAMP-dependent protein kinase (PKA).