sodium (4aR,6R,7R,7aS)-7-hydroxy-2-oxo-6-{9-oxo-6-phenyl-3H,5H,9H-imidazo[1,2-a]purin-3-yl}-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-olate

• ChemBase ID: 154239
• Molecular Formular: C18H15N5NaO7P
• Molecular Mass: 467.304531
• Monoisotopic Mass: 467.06067876
• SMILES: c1ccc(cc1)c1cn2c(=O)c3c(nc2[nH]1)n(cn3)[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)[O-])O.[Na+]
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)([O-])OC[C@H]2O[C@H]1n1cnc2c1nc1[nH]c(cn1c2=O)c1ccccc1.[Na+]
• InChI: InChI=1S/C18H16N5O7P.Na/c24-13-14-11(7-28-31(26,27)30-14)29-17(13)23-8-19-12-15(23)21-18-20-10(6-22(18)16(12)25)9-4-2-1-3-5-9;/h1-6,8,11,13-14,17,24H,7H2,(H,20,21)(H,26,27);/q;+1/p-1/t11-,13-,14-,17-;/m1./s1
• InChIKey: IGIOCJJIGJLGKR-TZNCIMHNSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4aR,6R,7R,7aS)-7-hydroxy-2-oxo-6-{9-oxo-6-phenyl-3H,5H,9H-imidazo[1,2-a]purin-3-yl}-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate
• IUPAC Traditional name: sodium (4aR,6R,7R,7aS)-7-hydroxy-2-oxo-6-{9-oxo-6-phenyl-5H-imidazo[1,2-a]purin-3-yl}-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate
• Synonyms: β-Phenyl-1,N2-ethenoguanosine 3′,5′-monophosphate sodium salt; PET-cGMP

Database IDs

• CAS Number: 78080-27-0
• MDL Number: MFCD04118064
• PubChem SID: 162248378; 24724570
• PubChem CID: 23672701

CALCULATED PROPERTIES

• Acid pKa: 1.9713365
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -2.3018181
• LogD (pH = 7.4): -2.3236842
• Log P: -0.4197941
• Molar Refractivity: 103.3563 cm^3
• Polarizability: 39.703735 Å^3
• Polar Surface Area: 150.57 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ~10 mmol
• 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: -70°C

Product Information

• Purity: ≥98% (HPLC)
• Packaging: pkg of 10 μmol
• Shipped in: dry ice
• Empirical Formula (Hill Notation): C18H15N5O7PNa

DETAILS

Sigma Aldrich - P0622

Biochem/physiol Actions
cGMP-dependent protein kinase (PKG I and PKG II) activator. Potent membrane permeant activator of both isozymes I α and I β of cGMP-dependent protein kinase. Common stimulators such as 8-Br-cGMP or 8-pCPT-cGMP mainly activate kinase subtype Iα.