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

• ChemBase ID: 166012
• Molecular Formular: C7H14N4O4
• Molecular Mass: 218.21046
• Monoisotopic Mass: 218.10150495
• SMILES: [C@H]1(CC(O[C@@H]1CO)NC(=O)NC(=N)N)O
• Canonical SMILES: OC[C@H]1OC(C[C@H]1O)NC(=O)NC(=N)N
• InChI: InChI=1S/C7H14N4O4/c8-6(9)11-7(14)10-5-1-3(13)4(2-12)15-5/h3-5,12-13H,1-2H2,(H5,8,9,10,11,14)/t3-,4-,5?/m1/s1
• InChIKey: VGUQMXPKKFTIJO-ZZKAVYKESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 3-carbamimidoyl-1-[(4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]urea
• IUPAC Traditional name: 3-carbamimidoyl-1-[(4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]urea
• Synonyms: N-(Aminoiminomethyl)-N'-(2-deoxy-D-erythro-pentofuranosyl)urea; D-2'-Deoxyribofuranosyl-3-guanylurea(α/β-Mixture)

Database IDs

• CAS Number: 570410-72-9
• PubChem SID: 162260145
• PubChem CID: 71315510

CALCULATED PROPERTIES

• Acid pKa: 12.196561
• H Acceptors: 6
• H Donor: 6
• LogD (pH = 5.5): -4.152616
• LogD (pH = 7.4): -2.643338
• Log P: -2.298256
• Molar Refractivity: 59.0649 cm^3
• Polarizability: 19.286983 Å^3
• Polar Surface Area: 140.69 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Pale Beige Solid
• Melting Point: 61-63°C

Safety Information

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

DETAILS

Toronto Research Chemicals - D253500

Used in the synthesis of N4-alkyl-5-azacytidines as mutagenic agents.

REFERENCES

• Beisler, Jj.A., et al.: J. Med. Chem., 21, 204 (1978)