sodium {[({[(2S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methyl phosphonato}oxy)(hydroxy)phosphoryl]oxy}phosphonic acid

• ChemBase ID: 133541
• Molecular Formular: C9H15N3NaO12P3
• Molecular Mass: 473.139353
• Monoisotopic Mass: 472.97662711
• SMILES: c1cn(c(=O)nc1N)[C@H]1CC[C@H](O1)COP(=O)([O-])OP(=O)(O)OP(=O)(O)O.[Na+]
• Canonical SMILES: Nc1ccn(c(=O)n1)[C@H]1CC[C@H](O1)COP(=O)(OP(=O)(OP(=O)(O)O)O)[O-].[Na+]
• InChI: InChI=1S/C9H16N3O12P3.Na/c10-7-3-4-12(9(13)11-7)8-2-1-6(22-8)5-21-26(17,18)24-27(19,20)23-25(14,15)16;/h3-4,6,8H,1-2,5H2,(H,17,18)(H,19,20)(H2,10,11,13)(H2,14,15,16);/q;+1/p-1/t6-,8+;/m0./s1
• InChIKey: LOOMQRBEBYCFPP-QDOHZIMISA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium {[({[(2S,5R)-5-(4-amino-2-oxo-1,2-dihydropyrimidin-1-yl)oxolan-2-yl]methyl phosphonato}oxy)(hydroxy)phosphoryl]oxy}phosphonic acid
• IUPAC Traditional name: sodium ({[(2S,5R)-5-(4-amino-2-oxopyrimidin-1-yl)oxolan-2-yl]methyl phosphonato}oxy(hydroxy)phosphoryl)oxyphosphonic acid
• Synonyms: ddCTP; 2′,3′-Dideoxycytidine 5′-triphosphate sodium salt; 2′,3′-Dideoxycytidine 5′-triphosphate sodium salt solution; 2′,3′-二脱氧胞苷 5′-三磷酸 钠盐; 2′,3′-二脱氧胞苷 5′-三磷酸 钠盐 溶液

Database IDs

• CAS Number: 132619-66-0
• EC Number: 231-791-2
• MDL Number: MFCD00717536
• PubChem SID: 162227818; 24894086; 24845244
• PubChem CID: 23679072

CALCULATED PROPERTIES

• Acid pKa: 1.0228447
• H Acceptors: 11
• H Donor: 4
• LogD (pH = 5.5): -8.831785
• LogD (pH = 7.4): -9.565652
• Log P: -2.6054146
• Molar Refractivity: 83.7372 cm^3
• Polarizability: 34.071552 Å^3
• Polar Surface Area: 230.57 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• German water hazard class: 2; 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥90% (HPLC); ≥98.0% (HPLC)
• Concentration: 10.0-11.0 (UV)
• Grade: for MALDI MS; puriss. p.a.
• Packaging: pkg of 1 μmol
• Suitability: corresponds for UV test
• Impurities: ≤1.5% ddNDP (HPLC)
• Empirical Formula (Hill Notation): C9H15N3NaO12P3

DETAILS

Sigma Aldrich - D7159

Application
Complexes of ddCTP with DNA polymerase β were studied by x-ray crystallography, with implications for inhibitory activity against HIV reverse transcriptase.1
Biochem/physiol Actions
Inhibitor of DNA polymerase I-catalyzed chain elongation.

Sigma Aldrich - 02241

Biochem/physiol Actions
Inhibitor of DNA polymerase I-catalyzed chain elongation.