sodium (4aR,6R,7R,7aS)-6-{2-amino-8-[(4-chlorophenyl)sulfanyl]-6-oxo-6,9-dihydro-1H-purin-9-yl}-7-hydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-2-olate

• ChemBase ID: 155352
• Molecular Formular: C16H14ClN5NaO7PS
• Molecular Mass: 509.793191
• Monoisotopic Mass: 508.9937774
• SMILES: c1cc(ccc1Sc1nc2c(=O)[nH]c(nc2n1[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)[O-])O)N)Cl.[Na+]
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)([O-])OC[C@H]2O[C@H]1n1c(Sc2ccc(cc2)Cl)nc2c1nc(N)[nH]c2=O.[Na+]
• InChI: InChI=1S/C16H15ClN5O7PS.Na/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(28-14)5-27-30(25,26)29-11;/h1-4,8,10-11,14,23H,5H2,(H,25,26)(H3,18,20,21,24);/q;+1/p-1/t8-,10-,11-,14-;/m1./s1
• InChIKey: REEQGIQRCDWDRA-ZBMQJGODSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4aR,6R,7R,7aS)-6-{2-amino-8-[(4-chlorophenyl)sulfanyl]-6-oxo-6,9-dihydro-1H-purin-9-yl}-7-hydroxy-2-oxo-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)-6-{2-amino-8-[(4-chlorophenyl)sulfanyl]-6-oxo-1H-purin-9-yl}-7-hydroxy-2-oxo-tetrahydro-4H-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-2-olate
• Synonyms: 8-pCPT-cGMP; pCPT-cGMP; 8-(4-Chlorophenylthio)-guanosine 3′,5′-cyclic monophosphate sodium salt

Database IDs

• CAS Number: 51239-26-0
• MDL Number: MFCD00674888
• PubChem SID: 162249490; 24892786
• PubChem CID: 23679064

CALCULATED PROPERTIES

• Acid pKa: 1.8410523
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -0.81009865
• LogD (pH = 7.4): -0.8330265
• Log P: 1.4516176
• Molar Refractivity: 107.5555 cm^3
• Polarizability: 41.982513 Å^3
• Polar Surface Area: 173.35 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: H2O: soluble25 mg/mL
• Apperance: white powder

Safety Information

• German water hazard class: 3
• Storage Temperature: -20°C

Product Information

• Purity: ~95% (HPLC)
• Empirical Formula (Hill Notation): C16H14ClN5NaO7PS

DETAILS

Sigma Aldrich - C5438

Biochem/physiol Actions
Membrane-permeable analog of cGMP that does not affect cGMP-regulated phosphodiesterase. A more potent cGMP analog than 8-Br-cGMP due to greater membrane permeability and a higher resistance to hydrolysis by phosphodiesterase. Used as a selective activator of cGMP dependent protein kinase (PKG). Found to be a very potent cyclic nucleotide-gated channel agonist.