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-6,9-dihydro-1H-purin-6-one; triethylamine

• ChemBase ID: 132731
• Molecular Formular: C16H27N6O6PS
• Molecular Mass: 462.460941
• Monoisotopic Mass: 462.14504024
• SMILES: CCN(CC)CC.c1nc2c(=O)[nH]c(nc2n1[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=S)(O2)O)O)N
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=S)(O)OC[C@H]2O[C@H]1n1cnc2c1nc(N)[nH]c2=O.CCN(CC)CC
• InChI: InChI=1S/C10H12N5O6PS.C6H15N/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(20-9)1-19-22(18,23)21-6;1-4-7(5-2)6-3/h2-3,5-6,9,16H,1H2,(H,18,23)(H3,11,13,14,17);4-6H2,1-3H3/t3-,5-,6-,9-,22?;/m1./s1
• InChIKey: SBVIQYPGQBMDDI-QKAIHBBZSA-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-6,9-dihydro-1H-purin-6-one; triethylamine; 9-[(2S,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-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-1H-purin-6-one; triethylamine; 9-[(2S,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-1H-purin-6-one; triethylamine
• Synonyms: Rp-Cyclic 3′,5′-hydrogen phosphorothioate guanosine triethylammonium salt; Rp-Diastereomer of guanosine 3′,5′-cyclic monophosphorothioate triethylammonium salt; Rp-cGMPS triethylammonium salt; Guanosine 3′,5′-cyclic monophosphorothioate, Rp Isomer triethylammonium salt; Sp-Cyclic 3′5′-hydrogen phosphorothioate guanosine triethylammonium salt; Sp-cGMPS triethylammonium salt; Sp-Guanosine 3′,5′-cyclic monophosphorothioate triethylammonium salt

Database IDs

• CAS Number: 86562-09-6; 86562-10-9
• MDL Number: MFCD04113738; MFCD04113739
• PubChem SID: 162227008
• PubChem CID: 57389992

CALCULATED PROPERTIES

• Acid pKa: 1.9713287
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -3.3761015
• LogD (pH = 7.4): -3.4198062
• Log P: -1.2221006
• Molar Refractivity: 79.7059 cm^3
• Polarizability: 30.919945 Å^3
• Polar Surface Area: 153.45 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

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

• Shipped in: dry ice

DETAILS

Sigma Aldrich - G136

Biochem/physiol Actions
Sp-cGMPS is a metabolically resistant activator of cGMP-dependent protein kinases.
Caution
Hygroscopic
Other Notes
Sp-Diastereomer of guanosine 3′,5′-cyclic monophosphorothioate.

Sigma Aldrich - G135

Biochem/physiol Actions
cGMPS-dependent protein kinase Iα inhibitor.
Caution
Hygroscopic