5-hydroxy-1-[(E)-{[5-(4-nitrophenyl)furan-2-yl]methylidene}amino]imidazolidine-2,4-dione

• ChemBase ID: 170179
• Molecular Formular: C14H10N4O6
• Molecular Mass: 330.2524
• Monoisotopic Mass: 330.06003406
• SMILES: c1cc(oc1c1ccc(cc1)[N+](=O)[O-])/C=N/N1C(=O)NC(=O)C1O
• Canonical SMILES: O=C1NC(=O)C(N1/N=C/c1ccc(o1)c1ccc(cc1)[N+](=O)[O-])O
• InChI: InChI=1S/C14H10N4O6/c19-12-13(20)17(14(21)16-12)15-7-10-5-6-11(24-10)8-1-3-9(4-2-8)18(22)23/h1-7,13,20H,(H,16,19,21)/b15-7+
• InChIKey: PGORTQZSSAZLCK-VIZOYTHASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-1-[(E)-{[5-(4-nitrophenyl)furan-2-yl]methylidene}amino]imidazolidine-2,4-dione
• IUPAC Traditional name: 5-hydroxy-1-[(E)-{[5-(4-nitrophenyl)furan-2-yl]methylidene}amino]imidazolidine-2,4-dione
• Synonyms: 5-Hydroxy-1-[[[5-(4-nitrophenyl)-2-furanyl]methylene]amino]-2,4-imidazolidinedione; 5-Hydroxy Dantrolene

Database IDs

• CAS Number: 52130-25-3
• PubChem SID: 164226089
• PubChem CID: 9577331

CALCULATED PROPERTIES

• Acid pKa: 8.84579
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): 0.9675521
• LogD (pH = 7.4): 0.95263267
• Log P: 0.9677458
• Molar Refractivity: 80.0729 cm^3
• Polarizability: 30.554985 Å^3
• Polar Surface Area: 140.96 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Yellow Solid
• Melting Point: 238-240°C dec.

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - H825175

A metabolite of Dantrolene (D185000) that has shown to have muscle relaxant effects.

REFERENCES

• Ellis, K.O., et al.: J. Med. Chem., 21, 127 (1977)
• Jayyosi, Z., et al.: Drug Metab. Dispos., 21, 939 (1977)