4-carbamoyl-1-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazol-3-ium-5-olate

• ChemBase ID: 174661
• Molecular Formular: C9H13N3O6
• Molecular Mass: 259.21602
• Monoisotopic Mass: 259.08043515
• SMILES: [C@H]1(C([C@@H]([C@@H](O1)n1c[nH+]c(c1[O-])C(=O)N)O)O)CO
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1c[nH+]c(c1[O-])C(=O)N
• InChI: InChI=1S/C9H13N3O6/c10-7(16)4-8(17)12(2-11-4)9-6(15)5(14)3(1-13)18-9/h2-3,5-6,9,13-15,17H,1H2,(H2,10,16)/t3-,5?,6+,9-/m1/s1
• InChIKey: HZQDCMWJEBCWBR-DTUHVUQASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-carbamoyl-1-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1H-imidazol-3-ium-5-olate
• IUPAC Traditional name: 5-carbamoyl-3-[(2R,3S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazol-1-ium-4-olate
• Synonyms: 5-Hydroxy-1-β-D-ribofuranosyl-1H-imidazole-4-carboxamide; β-Bredinin; Bredinin; HE 69; NSC 289637; Mizoribine

Database IDs

• CAS Number: 50924-49-7
• PubChem SID: 164230571
• PubChem CID: 46782385

CALCULATED PROPERTIES

• Acid pKa: 8.186375
• H Acceptors: 6
• H Donor: 5
• LogD (pH = 5.5): -2.0362294
• LogD (pH = 7.4): -2.0982585
• Log P: -2.032959
• Molar Refractivity: 66.396 cm^3
• Polarizability: 21.967472 Å^3
• Polar Surface Area: 155.14 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Ethanol; Methanol
• Apperance: White Solid
• Melting Point: >204°C (dec.)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - M385500

Nucleoside antibiotic with cytotoxic and immunosuppressive activity.

REFERENCES

• Sakaguchi, K., et al.: J. Antibiot., 28, 798 (1975)
• Takada, K., et al.: Eur. J. Pharmacol., 24, 457 (1975)
• Yoshida, N., et al.: Cancer Res., 43, 5851 (1975)