4-amino-1-[(2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro(4,5,6-13C3)pyrimidin-2-one

• ChemBase ID: 165326
• Molecular Formular: C9H13N3O5
• Molecular Mass: 246.19458451
• Monoisotopic Mass: 246.09558505
• SMILES: C1(O)[C@@H](CO)O[C@H]([C@H]1O)n1[13cH][13cH][13c](nc1=O)N
• Canonical SMILES: OC[C@H]1O[C@H]([C@H](C1O)O)n1[13cH][13cH][13c](nc1=O)N
• InChI: InChI=1S/C9H13N3O5/c10-5-1-2-12(9(16)11-5)8-7(15)6(14)4(3-13)17-8/h1-2,4,6-8,13-15H,3H2,(H2,10,11,16)/t4-,6?,7-,8-/m1/s1/i1+1,2+1,5+1
• InChIKey: UHDGCWIWMRVCDJ-QEDKJTRKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro(4,5,6-^1^3C₃)pyrimidin-2-one
• IUPAC Traditional name: 4-amino-1-[(2R,3R,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl](4,5,6-^1^3C₃)pyrimidin-2-one
• Synonyms: 4-amino-1-β-D-arabinofuranosyl-2(1H)pyrimidinone-13C3; Cytosine-β-D-arabinofuranoside-13C3; Cytarabine-13C3

Database IDs

• PubChem SID: 162259459
• PubChem CID: 71315149

CALCULATED PROPERTIES

• Acid pKa: 12.553241
• H Acceptors: 7
• H Donor: 4
• LogD (pH = 5.5): -2.7975185
• LogD (pH = 7.4): -2.7975204
• Log P: -2.7975173
• Molar Refractivity: 54.5448 cm^3
• Polarizability: 21.48729 Å^3
• Polar Surface Area: 128.61 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; DMSO; Hot Methanol
• Apperance: Off-White Solid
• Melting Point: 223-225°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C998102

Labelled Cytarabine, a compound used as an antineoplastic and antiviral. A selective inhibitro of DNA synthesis. Does not inhibit RNA synthesis.

REFERENCES

• Donehower, R.C., et al.: Cancer Treat. Rep., 70, 1059 (1986)