6-nitro-2-{[(6-nitro-1H-1,3-benzodiazol-2-yl)methoxy]methyl}-1H-1,3-benzodiazole

• ChemBase ID: 153274
• Molecular Formular: C16H12N6O5
• Molecular Mass: 368.30368
• Monoisotopic Mass: 368.08691751
• SMILES: c1cc2c(cc1[N+](=O)[O-])[nH]c(n2)COCc1[nH]c2cc(ccc2n1)[N+](=O)[O-]
• Canonical SMILES: [O-][N+](=O)c1ccc2c(c1)[nH]c(n2)COCc1nc2c([nH]1)cc(cc2)[N+](=O)[O-]
• InChI: InChI=1S/C16H12N6O5/c23-21(24)9-1-3-11-13(5-9)19-15(17-11)7-27-8-16-18-12-4-2-10(22(25)26)6-14(12)20-16/h1-6H,7-8H2,(H,17,19)(H,18,20)
• InChIKey: ZQPXNYLXYNRFNP-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 6-nitro-2-{[(6-nitro-1H-1,3-benzodiazol-2-yl)methoxy]methyl}-1H-1,3-benzodiazole
• IUPAC Traditional name: 5-nitro-2-{[(5-nitro-3H-1,3-benzodiazol-2-yl)methoxy]methyl}-3H-1,3-benzodiazole
• Synonyms: 2,2′-(oxydimethanediyl)bis(5-nitro-1H-benzimidazole); 2,2′-(oxydimethanediyl)bis(6-nitro-1H-benzimidazole); 5-nitro-2-{[(6-nitro-1H-benzimidazol-2-yl)methoxy]methyl}-1H-benzimidazole; VU591

Database IDs

• CAS Number: 1222810-74-3
• PubChem SID: 162247413
• PubChem CID: 44123657

CALCULATED PROPERTIES

• Acid pKa: 8.754847
• H Acceptors: 7
• H Donor: 2
• LogD (pH = 5.5): 2.1321247
• LogD (pH = 7.4): 2.1551692
• Log P: 2.1723132
• Molar Refractivity: 93.3621 cm^3
• Polarizability: 36.694653 Å^3
• Polar Surface Area: 158.23 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: ≥12 mg/mL
• Apperance: white to tan powder

Safety Information

• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... KCNJ1(3758)

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C16H12N6O5

DETAILS

Sigma Aldrich - SML0077

Biochem/physiol Actions
VU591 is a Potassium Inwardly-Rectifying Channel (KCNJ1 or ROMK) specific inhibitor (IC50 = 240 nM) that is closely related to VU590. Unlike VU590, VU591 does not inhibit Kir7.1. The compound has a modest effect on Kir6.2/SUR1, causing 17% inhibition at 10 uM.