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

• ChemBase ID: 156733
• Molecular Formular: C18H28N6O16P2
• Molecular Mass: 646.393042
• Monoisotopic Mass: 646.10370211
• SMILES: c1cn(c(=O)nc1N)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)OP(=O)(O)O)O.c1cn(c(=O)nc1N)[C@H]1[C@@H]([C@@H]([C@H](O1)CO)O)OP(=O)(O)O
• Canonical SMILES: OC[C@H]1O[C@H]([C@@H]([C@@H]1OP(=O)(O)O)O)n1ccc(nc1=O)N.OC[C@H]1O[C@H]([C@@H]([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)/t2*4-,6-,7-,8-/m11/s1
• InChIKey: DSZXBLYFKPSDKQ-SGOXFDQRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[(2R,3R,4R,5R)-2-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4-hydroxy-5-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid; {[(2R,3S,4R,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid
• IUPAC Traditional name: [(2R,3S,4R,5R)-5-(4-amino-2-oxopyrimidin-1-yl)-4-hydroxy-2-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid cytidine 2'-phosphate
• Synonyms: 3′(+2′)-CMP; Cytidine-3′(+2′)-monophosphate; Cytidylic acid

Database IDs

• CAS Number: 27214-06-8
• EC Number: 201-537-5
• MDL Number: MFCD00213399
• Beilstein Number: 46971
• PubChem SID: 162250870; 24858113
• PubChem CID: 16211908

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

PROPERTIES

Physical Property

• Melting Point: 230-240 °C (dec.)
• Optical Rotation: [α]20/D +37±3°, c = 1% in H2O

Safety Information

• German water hazard class: 3
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98.0% (HPLC)
• Empirical Formula (Hill Notation): C9H14N3O8P