N-[({[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]carbamoyl}amino)methanimidoyl]formamide

• ChemBase ID: 169430
• Molecular Formular: C8H14N4O6
• Molecular Mass: 262.21996
• Monoisotopic Mass: 262.09133419
• SMILES: [C@@H]1([C@H](C(O[C@@H]1CO)NC(=O)NC(=N)NC=O)O)O
• Canonical SMILES: O=CNC(=N)NC(=O)NC1O[C@@H]([C@H]([C@H]1O)O)CO
• InChI: InChI=1S/C8H14N4O6/c9-7(10-2-14)12-8(17)11-6-5(16)4(15)3(1-13)18-6/h2-6,13,15-16H,1H2,(H4,9,10,11,12,14,17)/t3-,4-,5-,6?/m1/s1
• InChIKey: KLSAIGPSXJMERX-JDJSBBGDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[({[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]carbamoyl}amino)methanimidoyl]formamide
• IUPAC Traditional name: N-[({[(3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]carbamoyl}amino)methanimidoyl]formamide
• Synonyms: [(Formylamino)iminomethyl]ribofuranosylurea; NSC 279851; N-(formylamidino)-N'-ribofuranosylurea; N-Formyl-D-ribofuranosyl-3-guanylurea (~85%)(α/β-Mixture)

Database IDs

• CAS Number: 686299-20-7
• PubChem SID: 162263562
• PubChem CID: 71316962

CALCULATED PROPERTIES

• Acid pKa: 11.553187
• H Acceptors: 7
• H Donor: 7
• LogD (pH = 5.5): -3.3406656
• LogD (pH = 7.4): -3.316496
• Log P: -3.3161511
• Molar Refractivity: 65.5289 cm^3
• Polarizability: 21.99049 Å^3
• Polar Surface Area: 164.0 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Pale Yellow Semi Solid

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - F700940

An impurity of 5-Azacytidine (A796000) with potential neoplasm inhibitory effects.

REFERENCES

• Beisler, J.A.: J. Med. Chem., 21, 204 (1978)
• Chan, K.K. et al.: J. Pharmaceut. Sci., 68, 807 (1978)