(4aR,6R,7R,7aS)-6-[6-amino-8-(hexylamino)-9H-purin-9-yl]-2,7-dihydroxy-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinine-2-thione

• ChemBase ID: 155669
• Molecular Formular: C16H25N6O5PS
• Molecular Mass: 444.445661
• Monoisotopic Mass: 444.13447556
• SMILES: CCCCCCNc1nc2c(ncnc2n1[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=S)(O2)O)O)N
• Canonical SMILES: CCCCCCNc1nc2c(n1[C@@H]1O[C@H]3[C@H]([C@H]1O)OP(=S)(OC3)O)ncnc2N
• InChI: InChI=1S/C16H25N6O5PS/c1-2-3-4-5-6-18-16-21-10-13(17)19-8-20-14(10)22(16)15-11(23)12-9(26-15)7-25-28(24,29)27-12/h8-9,11-12,15,23H,2-7H2,1H3,(H,18,21)(H,24,29)(H2,17,19,20)/t9-,11-,12-,15-,28?/m1/s1
• InChIKey: IYCUPZSIJJABKU-IYKFWPKASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4aR,6R,7R,7aS)-6-[6-amino-8-(hexylamino)-9H-purin-9-yl]-2,7-dihydroxy-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinine-2-thione
• IUPAC Traditional name: (4aR,6R,7R,7aS)-6-[6-amino-8-(hexylamino)purin-9-yl]-2,7-dihydroxy-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinine-2-thione
• Synonyms: Rp-8-HA-cAMPS; Rp-8-Hexylaminoadenosine 3′,5′-monophosphorothioate

Database IDs

• PubChem SID: 162249807
• PubChem CID: 71312195

CALCULATED PROPERTIES

• Acid pKa: 1.8883821
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -0.46277696
• LogD (pH = 7.4): -0.43485856
• Log P: -0.6029701
• Molar Refractivity: 111.0231 cm^3
• Polarizability: 43.231457 Å^3
• Polar Surface Area: 149.8 Å^2
• Rotatable Bonds: 7
• 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 5 μmol (approx. 2 mg)
• Empirical Formula (Hill Notation): C16H24N6O5PSNa

DETAILS

Sigma Aldrich - H2036

Biochem/physiol Actions
Membrane permeable metabolically stable inhibitor of cAMP-dependent protein kinases