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

• ChemBase ID: 134246
• Molecular Formular: C9H17N4O7P
• Molecular Mass: 324.227641
• Monoisotopic Mass: 324.08348553
• SMILES: c1cn(c(=O)nc1N)C1CC(C(O1)CO)OP(=O)(O)O.N
• Canonical SMILES: OCC1OC(CC1OP(=O)(O)O)n1ccc(nc1=O)N.N
• InChI: InChI=1S/C9H14N3O7P.H3N/c10-7-1-2-12(9(14)11-7)8-3-5(6(4-13)18-8)19-20(15,16)17;/h1-2,5-6,8,13H,3-4H2,(H2,10,11,14)(H2,15,16,17);1H3
• InChIKey: VCTPYSBTEURORB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: {[5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl]oxy}phosphonic acid amine
• IUPAC Traditional name: [5-(4-amino-2-oxopyrimidin-1-yl)-2-(hydroxymethyl)oxolan-3-yl]oxyphosphonic acid amine
• Synonyms: 3′-dCMP; 2′-Deoxycytidine 3′-monophosphate ammonium salt

Database IDs

• CAS Number: 102783-50-6
• MDL Number: MFCD00058230
• PubChem SID: 162228523; 24894059
• PubChem CID: 16219267

CALCULATED PROPERTIES

• Acid pKa: 1.1573411
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -4.485237
• LogD (pH = 7.4): -5.6634254
• Log P: -2.3395295
• Molar Refractivity: 63.907 cm^3
• Polarizability: 25.347824 Å^3
• Polar Surface Area: 154.91 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥97%

DETAILS

Sigma Aldrich - D6897

Application
2′-Deoxycytidine 3′-monophosphate (3′-dCMP) and 3′-dCMPH are used as a model molecules to elucidate the mechanism(s) of the nascent stage of DNA strand breakage and to study nucleic acid base modifications by adduct formation.