{[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid; {[(2R,4S,5R)-2-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid

• ChemBase ID: 165330
• Molecular Formular: C18H28N6O16P2
• Molecular Mass: 646.393042
• Monoisotopic Mass: 646.10370211
• SMILES: n1([C@H]2C([C@H]([C@H](O2)CO)OP(=O)(O)O)O)ccc(nc1=O)N.n1([C@H]2C([C@H]([C@H](O2)CO)O)OP(=O)(O)O)ccc(nc1=O)N
• Canonical SMILES: OC[C@H]1O[C@H](C([C@H]1OP(=O)(O)O)O)n1ccc(nc1=O)N.OC[C@H]1O[C@H](C([C@H]1O)OP(=O)(O)O)n1ccc(nc1=O)N
• InChI: InChI=1S/2C9H14N3O8P/c10-5-1-2-12(9(15)11-5)8-6(14)7(4(3-13)19-8)20-21(16,17)18;10-5-1-2-12(9(15)11-5)8-7(20-21(16,17)18)6(14)4(3-13)19-8/h2*1-2,4,6-8,13-14H,3H2,(H2,10,11,15)(H2,16,17,18)/t4-,6?,7+,8-;4-,6+,7?,8-/m11/s1
• InChIKey: DSZXBLYFKPSDKQ-SFCWMERESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid; {[(2R,4S,5R)-2-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(2R,3R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid; [(2R,4S,5R)-2-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid
• Synonyms: 3'(2’)-Cytidylic Acid; 3'(2’)-CMP; 3'(2’)-Cytidinephosphoric Acid; 3'(2’)-Cytosylic Acid; Ribocytidine 3'(2’)-Monophosphate; Cytidine 3'(2')-Monophosphate

Database IDs

• CAS Number: 84-52-6
• PubChem SID: 162259463
• PubChem CID: 71315151

CALCULATED PROPERTIES

• Acid pKa: 0.9248102
• H Acceptors: 9
• H Donor: 5
• LogD (pH = 5.5): -5.438055
• LogD (pH = 7.4): -6.7513933
• Log P: -3.2232413
• Molar Refractivity: 65.4177 cm^3
• Polarizability: 26.073345 Å^3
• Polar Surface Area: 175.14 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - C998310

A metabolite of Cytidine (C998300). A highly specific phosphatase that acts on ADP-ribose 1''-phosphate, a metabolite of tRNA splicing in Saccharomyces cerevisiae.

REFERENCES

• Phizicky, E., et al.: J. Biol. Chem., 267, 4577 (1992)
• Murguia, J., et al.: Science, 267, 232 (1992)
• Lei, M., et al.: Biochemistry, 41, 14560 (1992)