sodium (4aR,6R,7R,7aS)-6-(2-amino-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: 132314
• Molecular Formular: C10H11N5NaO7P
• Molecular Mass: 367.187171
• Monoisotopic Mass: 367.02937863
• SMILES: c1nc2c(=O)[nH]c(nc2n1[C@H]1[C@@H]([C@H]2[C@H](O1)COP(=O)(O2)[O-])O)N.[Na+]
• Canonical SMILES: O[C@@H]1[C@@H]2OP(=O)([O-])OC[C@H]2O[C@H]1n1cnc2c1nc(N)[nH]c2=O.[Na+]
• InChI: InChI=1S/C10H12N5O7P.Na/c11-10-13-7-4(8(17)14-10)12-2-15(7)9-5(16)6-3(21-9)1-20-23(18,19)22-6;/h2-3,5-6,9,16H,1H2,(H,18,19)(H3,11,13,14,17);/q;+1/p-1/t3-,5-,6-,9-;/m1./s1
• InChIKey: KMPIYXNEROUNOG-GWTDSMLYSA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (4aR,6R,7R,7aS)-6-(2-amino-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 3',5'-cyclic gmp anion
• Synonyms: 3′,5′-Cyclic GMP monosodium salt; 3′,5′-cGMP-Na; Guanosine 3′,5′-cyclophosphate monosodium salt; cGMP; cyclic GMP; Guanosine 3′,5′-cyclic monophosphate sodium salt; Guanosine Cyclic 3',5'-(Hydrogen phosphate) Sodium Salt; Cyclic 3',5'-Guanosine Monophosphate Monosodium Salt; Guanosine Monophosphate Monosodium Salt; Monosodium-GMP; Guanosine 3',5'-Cyclic Monophosphate Sodium Salt

Database IDs

• CAS Number: 40732-48-7
• EC Number: 255-056-0
• MDL Number: MFCD00038424
• Beilstein Number: 6467425
• PubChem SID: 162226591; 24895245
• PubChem CID: 23702131

CALCULATED PROPERTIES

• Acid pKa: 2.0500584
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -4.2590003
• LogD (pH = 7.4): -4.309573
• Log P: -2.0959094
• Molar Refractivity: 70.5933 cm^3
• Polarizability: 27.621025 Å^3
• Polar Surface Area: 173.35 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: soluble50 mg/mL
• Apperance: white powder

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); ≥99.0% (HPLC)
• Shipped in: wet ice
• Empirical Formula (Hill Notation): C10H11N5NaO7P

DETAILS

Sigma Aldrich - G6129

Biochem/physiol Actions
An important second messenger, cGMP is a major intracellular mediator of extracellular signals such as nitric oxide and natriuretic peptides. Cyclic GMP interacts with three types of intracellular receptor proteins: cGMP-dependent protein kinases, cGMP-regulated channels, and cGMP-regulated cyclic nucleotide phosphodiesterases. A primary action of elevated cGMP levels in vivo is the stimulation of cGMP-dependent protein kinase (PKG).

Sigma Aldrich - 51055

Biochem/physiol Actions
An important second messenger, cGMP is a major intracellular mediator of extracellular signals such as nitric oxide and natriuretic peptides. Cyclic GMP interacts with three types of intracellular receptor proteins: cGMP-dependent protein kinases, cGMP-regulated channels, and cGMP-regulated cyclic nucleotide phosphodiesterases. A primary action of elevated cGMP levels in vivo is the stimulation of cGMP-dependent protein kinase (PKG).

Toronto Research Chemicals - G837960

Guanosine 3’,5’-Cyclic Monophosphate is a substituted Guanosine having cyclic phosphodiesterase activity.

REFERENCES

• Tazawa, et al.: Biochemistry, 11, 4931 (1972)