trisodium ({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate

• ChemBase ID: 165331
• Molecular Formular: C9H12N3Na3O11P2
• Molecular Mass: 469.121912
• Monoisotopic Mass: 468.96401432
• SMILES: n1([C@H]2[C@@H]([C@@H]([C@H](O2)COP(=O)(OP(=O)([O-])[O-])[O-])O)O)ccc(nc1=O)N.[Na+].[Na+].[Na+]
• Canonical SMILES: O[C@@H]1[C@@H](COP(=O)(OP(=O)([O-])[O-])[O-])O[C@H]([C@@H]1O)n1ccc(nc1=O)N.[Na+].[Na+].[Na+]
• InChI: InChI=1S/C9H15N3O11P2.3Na/c10-5-1-2-12(9(15)11-5)8-7(14)6(13)4(22-8)3-21-25(19,20)23-24(16,17)18;;;/h1-2,4,6-8,13-14H,3H2,(H,19,20)(H2,10,11,15)(H2,16,17,18);;;/q;3*+1/p-3/t4-,6-,7-,8-;;;/m1.../s1
• InChIKey: JENUKVZGXGULDX-LLWADOMFSA-K

NAMES AND DATABASE IDS

Names

• IUPAC name: trisodium ({[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxy)phosphonate
• IUPAC Traditional name: trisodium {[(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-3,4-dihydroxyoxolan-2-yl]methyl phosphonato}oxyphosphonate
• Synonyms: Cytidine 5'-(Trihydrogen Diphosphate) Trisodium Salt Hydrate; Cytidine 5'-(Trihydrogen Pyrophosphate) Trisodium Salt Hydrate; Trisodium Cytidine 5'-Diphosphate Hydrate; Cytidine 5'-Diphosphate Trisodium Salt Hydrate

Database IDs

• PubChem SID: 162259464
• PubChem CID: 23519589

CALCULATED PROPERTIES

• Acid pKa: 1.7790669
• H Acceptors: 11
• H Donor: 3
• LogD (pH = 5.5): -7.7458944
• LogD (pH = 7.4): -8.376884
• Log P: -3.3428817
• Molar Refractivity: 72.9255 cm^3
• Polarizability: 30.505592 Å^3
• Polar Surface Area: 230.16 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C998315

A diphosphate nucleoside derived from Cytidine (C998300). An inhibitor of glycogenin-catalyzed glucosyl and xylosyl transfer It is used as a therapeutic agent in treatment prevention of myocardial ischemia accompanied with cerebral ischemia.

REFERENCES

• Manzella, S. et al.: Arch. Biochem. Biophys., 320, 361 (1995)
• Liu, M. et al.: Hebei Yike Dax. Xueb., 18, 328 (1995)