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

• ChemBase ID: 133852
• Molecular Formular: C22H30ClN6O6PS2
• Molecular Mass: 605.066961
• Monoisotopic Mass: 604.10943902
• SMILES: CCN(CC)CC.c1cc(ccc1Sc1nc2c(=O)[nH]c(nc2n1[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=S)(O2)O)O)N)Cl
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=S)(O)OC[C@H]2O[C@H]1n1c(Sc2ccc(cc2)Cl)nc2c1nc(N)[nH]c2=O.CCN(CC)CC
• InChI: InChI=1S/C16H15ClN5O6PS2.C6H15N/c17-6-1-3-7(4-2-6)31-16-19-9-12(20-15(18)21-13(9)24)22(16)14-10(23)11-8(27-14)5-26-29(25,30)28-11;1-4-7(5-2)6-3/h1-4,8,10-11,14,23H,5H2,(H,25,30)(H3,18,20,21,24);4-6H2,1-3H3/t8-,10-,11-,14-,29?;/m1./s1
• InChIKey: KVOYZBYGWGWWTD-OZOPYAHTSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 9-[(2R,4aR,6R,7R,7aS)-2,7-dihydroxy-2-sulfanylidene-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-6-yl]-2-amino-8-[(4-chlorophenyl)sulfanyl]-6,9-dihydro-1H-purin-6-one; triethylamine
• IUPAC Traditional name: 9-[(2R,4aR,6R,7R,7aS)-2,7-dihydroxy-2-sulfanylidene-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-6-yl]-2-amino-8-[(4-chlorophenyl)sulfanyl]-1H-purin-6-one; triethylamine
• Synonyms: Rp-8-CPT-cGMPS; Rp-8-[(4-Chlorophenyl)thio]-cGMPS triethylammonium salt; Rp-8-[(4-Chlorophenyl)thio]-guanosine-cyclic 3′,5′-hydrogen phosphorothioate triethylammonium salt; 8-(4-Chlorophenylthio)-guanosine 3′,5′-cyclic monophosphorothioate, Rp Isomer triethylammonium salt

Database IDs

• CAS Number: 276696-61-8
• MDL Number: MFCD04037247
• PubChem SID: 162228129
• PubChem CID: 9873592

CALCULATED PROPERTIES

• Acid pKa: 1.6156783
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 0.07098941
• LogD (pH = 7.4): 0.056727815
• Log P: 2.3171697
• Molar Refractivity: 116.6681 cm^3
• Polarizability: 45.34195 Å^3
• Polar Surface Area: 153.45 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble5 mg/mL
• Apperance: white 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: ≥98% (HPLC)

DETAILS

Sigma Aldrich - C240

Biochem/physiol Actions
Rp-8-CPT-cGMP is a potent inhibitor of protein kinase G Ia, Ib, and type II.
Linkage
8-(4-Chlorophenylthio)-guanosine 3′,5′-cyclic monophosphorothioate, Rp Isomer triethylammonium salt is more cell permeable than Rp-cGMPS triethylamine.