3-carbamimidoyl-1-[(4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]urea

• ChemBase ID: 177517
• Molecular Formular: C7H14N4O5
• Molecular Mass: 234.20986
• Monoisotopic Mass: 234.09641957
• SMILES: [C@H]1(C(C(O[C@@H]1CO)NC(=O)NC(=N)N)O)O
• Canonical SMILES: OC[C@H]1OC(C([C@H]1O)O)NC(=O)NC(=N)N
• InChI: InChI=1S/C7H14N4O5/c8-6(9)11-7(15)10-5-4(14)3(13)2(1-12)16-5/h2-5,12-14H,1H2,(H5,8,9,10,11,15)/t2-,3+,4?,5?/m1/s1
• InChIKey: KSNSQOVBNYYHLW-JAKZDEMDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-carbamimidoyl-1-[(4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]urea
• IUPAC Traditional name: 3-carbamimidoyl-1-[(4R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]urea
• Synonyms: N-(aminoiminomethyl)-N'-D-ribofuranosylurea; 1-Amidino-3-D-ribofuranosylurea; 1-D-Ribofuranosyl-3-guanylurea(α/β-Mixture)

Database IDs

• PubChem SID: 164233427
• PubChem CID: 71752070

CALCULATED PROPERTIES

• Acid pKa: 11.681304
• H Acceptors: 7
• H Donor: 7
• LogD (pH = 5.5): -5.0270104
• LogD (pH = 7.4): -3.5246172
• Log P: -3.198894
• Molar Refractivity: 60.5756 cm^3
• Polarizability: 20.000322 Å^3
• Polar Surface Area: 160.92 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

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

DETAILS

Toronto Research Chemicals - R415600

A labile hydrolysis product of the antitumor nuceloside 5-Azacytidine (A796000).

REFERENCES

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