N-{1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}docosanamide

• ChemBase ID: 167927
• Molecular Formular: C31H55N3O6
• Molecular Mass: 565.7849
• Monoisotopic Mass: 565.4090865
• SMILES: [C@H]1([C@@H]([C@H](O[C@H]1n1ccc(nc1=O)NC(=O)CCCCCCCCCCCCCCCCCCCCC)CO)O)O
• Canonical SMILES: CCCCCCCCCCCCCCCCCCCCCC(=O)Nc1ccn(c(=O)n1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)CO
• InChI: InChI=1S/C31H55N3O6/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-20-21-27(36)32-26-22-23-34(31(39)33-26)30-29(38)28(37)25(24-35)40-30/h22-23,25,28-30,35,37-38H,2-21,24H2,1H3,(H,32,33,36,39)/t25-,28-,29+,30-/m1/s1
• InChIKey: SAMRUMKYXPVKPA-VFKOLLTISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-{1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxo-1,2-dihydropyrimidin-4-yl}docosanamide
• IUPAC Traditional name: N-{1-[(2R,3S,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-2-oxopyrimidin-4-yl}docosanamide
• Synonyms: N-(1-B-D-Arabinofuranosyl-1,2-dihydro-2-oxo-4-pyrimidinyl)docosanamide, Behenoylcytosine Arabinoside, BH-AC, NSC-239336, Sunrabin; Enocitabine

Database IDs

• CAS Number: 55726-47-1
• PubChem SID: 162262060
• PubChem CID: 71734

CALCULATED PROPERTIES

• Acid pKa: 12.459424
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): 6.281265
• LogD (pH = 7.4): 6.281261
• Log P: 6.281265
• Molar Refractivity: 156.0345 cm^3
• Polarizability: 61.838917 Å^3
• Polar Surface Area: 131.69 Å^2
• Rotatable Bonds: 23
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: Crystalline Solid
• Melting Point: 141-142°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - E557500

An antineoplastic. A derivative of Cytarabine.

REFERENCES

• Aoshima, M., et al.: Cancer Res., 36, 2726 (1976)
• Akiyama, M., et al.: Chem. Pharm. Bull., 26, 981 (1976)