5-azanidyl-3-(morpholin-4-yl)-1,2,3λ5-oxadiazol-3-ylium hydrochloride

• ChemBase ID: 131552
• Molecular Formular: C6H11ClN4O2
• Molecular Mass: 206.63014
• Monoisotopic Mass: 206.05705329
• SMILES: c1c(on[n+]1N1CCOCC1)[NH-].Cl
• Canonical SMILES: [NH-]c1on[n+](c1)N1CCOCC1.Cl
• InChI: InChI=1S/C6H10N4O2.ClH/c7-6-5-10(8-12-6)9-1-3-11-4-2-9;/h5,7H,1-4H2;1H
• InChIKey: NCGICGYLBXGBGN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-azanidyl-3-(morpholin-4-yl)-1,2,3λ^5-oxadiazol-3-ylium hydrochloride
• IUPAC Traditional name: 5-azanidyl-3-(morpholin-4-yl)-1,2,3λ^5-oxadiazol-3-ylium hydrochloride
• Synonyms: SIN-1 hydrochloride; 3-Morpholinosydnonimine hydrochloride; 3-(4-Morpholinyl)sydnone imine hydrochloride; Linsidomine hydrochloride

Database IDs

• CAS Number: 16142-27-1
• MDL Number: MFCD00214332
• PubChem SID: 162225830; 24278580; 24897048
• PubChem CID: 9859122

CALCULATED PROPERTIES

• Acid pKa: 8.8769245
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): -2.0612547
• LogD (pH = 7.4): -2.068631
• Log P: -2.0596268
• Molar Refractivity: 60.3173 cm^3
• Polarizability: 15.185209 Å^3
• Polar Surface Area: 62.61 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: >10 mg/mL
• Apperance: off-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

• Purity: (consistent with structure, NMR)

DETAILS

Sigma Aldrich - M184

Caution
Hygroscopic, photosensitive
Biochem/physiol Actions
Liberates nitric oxide (NO) spontaneously when in solution, activating guanylyl cyclase and causing an increase in cyclic-GMP. This product is a vasodilator and inhibits platelet aggregation. Using molecular oxygen, it generates both superoxide anion and nitric oxide that spontaneously form peroxynitrite.

Sigma Aldrich - M5793

Biochem/physiol Actions
Liberates nitric oxide (NO) spontaneously when in solution, activating guanylyl cyclase and causing an increase in cyclic-GMP. This product is a vasodilator and inhibits platelet aggregation. Using molecular oxygen, it generates both superoxide anion and nitric oxide that spontaneously form peroxynitrite.