(2R,4aR,6R,7R,7aS)-6-(6-amino-8-chloro-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: 155660
• Molecular Formular: C10H11ClN5O5PS
• Molecular Mass: 379.716601
• Monoisotopic Mass: 378.99070379
• SMILES: c1nc(c2c(n1)n(c(n2)Cl)[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(Cl)nc2c1ncnc2N
• InChI: InChI=1S/C10H11ClN5O5PS/c11-10-15-4-7(12)13-2-14-8(4)16(10)9-5(17)6-3(20-9)1-19-22(18,23)21-6/h2-3,5-6,9,17H,1H2,(H,18,23)(H2,12,13,14)/t3-,5-,6-,9-,22-/m1/s1
• InChIKey: PJAHPRNGOHUYQD-KVBUDSETSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,4aR,6R,7R,7aS)-6-(6-amino-8-chloro-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-chloropurin-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: Rp-8-Cl-cAMPS; 8-Chloroadenosine-3′,5′-cyclic monophosphorothioate, Rp-isomer

Database IDs

• CAS Number: 142754-27-6
• PubChem SID: 162249798
• PubChem CID: 44755048

CALCULATED PROPERTIES

• Acid pKa: 0.9687664
• H Acceptors: 7
• H Donor: 3
• LogD (pH = 5.5): -1.2121005
• LogD (pH = 7.4): -1.2015183
• Log P: -2.2658997
• Molar Refractivity: 79.3066 cm^3
• Polarizability: 32.53203 Å^3
• Polar Surface Area: 134.61 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 5 μmol
• Empirical Formula (Hill Notation): C10H10ClN5O5PSNa

DETAILS

Sigma Aldrich - C0610

Biochem/physiol Actions
Competitive inhibitor of cyclic AMP-dependent protein kinase A (PKA) type I. Membrane-permeable analog of the cAMP inhibitor Rp-cAMPS (Prod. No. A-165).