4-amino-1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro(2-13C,1,3-15N2)pyrimidin-2-one

• ChemBase ID: 165880
• Molecular Formular: C9H13N3O4
• Molecular Mass: 230.19669263
• Monoisotopic Mass: 230.08803054
• SMILES: [C@H]1(C[C@@H](O[C@@H]1CO)[15n]1[13c](=O)[15n]c(cc1)N)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@H]1O)[15n]1ccc([15n][13c]1=O)N
• InChI: InChI=1S/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)/t5-,6-,8-/m1/s1/i9+1,11+1,12+1
• InChIKey: CKTSBUTUHBMZGZ-CYJRVBDISA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydro(2-^1^3C,1,3-^1^5N₂)pyrimidin-2-one
• IUPAC Traditional name: 4-amino-1-[(2R,4R,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl](2-^1^3C,1,3-^1^5N₂)pyrimidin-2-one
• Synonyms: 1-(2-Deoxy-β-D-ribofuranosyl)cytosine-13C,15N2; 4-Amino-1-(2-deoxy-β-D-erythro-pentofuranosyl)-2(1H)-pyrimidinone-13C,15N2; Cytosine Deoxyribonucleoside-13C,15N2; Cytosine Deoxyriboside-13C,15N2; Deoxycytidine-13C,15N2; 2'-Deoxy Cytidine-13C,15N2

Database IDs

• PubChem SID: 162260013
• PubChem CID: 46780611

CALCULATED PROPERTIES

• Acid pKa: 13.894901
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.896882
• LogD (pH = 7.4): -1.8968794
• Log P: -1.8968792
• Molar Refractivity: 53.0341 cm^3
• Polarizability: 20.786694 Å^3
• Polar Surface Area: 108.38 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol; Water
• Apperance: Off-White Solid
• Melting Point: 181-185°C

Safety Information

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

DETAILS

Toronto Research Chemicals - D232617

A deoxyribonucleoside as Eg5 kinesin modulator with antiproliferative and apoptosis-inducing activity.

REFERENCES

• Hecht, S., et al.: Chem. Res. Toxicol., 17, 588 (2004)
• Choi, J., et al.: J. Biol. Chem., 281, 38244 (2004)
• Lao, Y., et al.: Chem. Res. Toxicol., 20, 246 (2004)