2-amino-9-{2,7-dihydroxy-2-oxo-hexahydro-1,3,5,2λ5-furo[3,2-d][1,3,2λ5]dioxaphosphinin-6-yl}-6,9-dihydro-3H-purin-6-one

• ChemBase ID: 133594
• Molecular Formular: C10H12N5O7P
• Molecular Mass: 345.205341
• Monoisotopic Mass: 345.04743438
• SMILES: c1nc2c(n1C1C(C3C(O1)COP(=O)(O3)O)O)[nH]c(nc2=O)N
• Canonical SMILES: OC1C2OP(=O)(O)OCC2OC1n1cnc2c1[nH]c(N)nc2=O
• InChI: InChI=1S/C10H12N5O7P/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)
• InChIKey: ZOOGRGPOEVQQDX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-amino-9-{2,7-dihydroxy-2-oxo-hexahydro-1,3,5,2λ^5-furo[3,2-d][1,3,2λ^5]dioxaphosphinin-6-yl}-6,9-dihydro-3H-purin-6-one
• IUPAC Traditional name: cyclic guanosine monophosphate
• Synonyms: cGMP; cyclic GMP; Guanosine 3′,5′-cyclic monophosphate

Database IDs

• CAS Number: 7665-99-8
• EC Number: 231-641-6
• MDL Number: MFCD00070129
• PubChem SID: 162227871; 24895309
• PubChem CID: 295

CALCULATED PROPERTIES

• Acid pKa: 1.762072
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): -3.7717755
• LogD (pH = 7.4): -3.887292
• Log P: -2.3542986
• Molar Refractivity: 71.2816 cm^3
• Polarizability: 27.9194 Å^3
• Polar Surface Area: 170.52 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1% NaHCO3: soluble50 mg/mL
• Apperance: white powder

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 22-26-36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves
• Storage Temperature: -20°C

Product Information

• Purity: ≥98% (HPLC)

DETAILS

Sigma Aldrich - G7504

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).
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. G7504.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.