4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one

• ChemBase ID: 126903
• Molecular Formular: C9H13N3O4
• Molecular Mass: 227.21722
• Monoisotopic Mass: 227.09060591
• SMILES: c1cn(c(=O)nc1N)[C@H]1C[C@@H]([C@H](O1)CO)O
• Canonical SMILES: OC[C@H]1O[C@H](C[C@@H]1O)n1ccc(nc1=O)N
• InChI: InChI=1S/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)/t5-,6+,8+/m0/s1
• InChIKey: CKTSBUTUHBMZGZ-SHYZEUOFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 4-amino-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-one
• IUPAC Traditional name: 2'-deoxycytidine
• Synonyms: Deoxycytidine; 2′-Deoxycytidine; 4-Amino-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidin-2(1H)-one; 2'-脱氧胞嘧啶核苷; 2′-脱氧胞苷

Database IDs

• CAS Number: 951-77-9
• EC Number: 213-454-1
• MDL Number: MFCD00006547
• Beilstein Number: 87567
• PubChem SID: 162221229; 24893793
• PubChem CID: 13711; 637
• CHEBI ID: 15698
• CHEMBL: 66115
• Chemspider ID: 13117
• MeSH Name: Deoxycytidine
• Wikipedia Title: Deoxycytidine

CALCULATED PROPERTIES

• Acid pKa: 13.894901
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): -1.896882
• LogD (pH = 7.4): -1.8968794
• Log P: -1.8968792
• Molar Refractivity: 53.0341 cm^3
• Polarizability: 20.786694 Å^3
• Polar Surface Area: 108.38 Å^2
• Rotatable Bonds: 2
• 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

Product Information

• Purity: ≥99% (HPLC); 95+%

DETAILS

Sigma Aldrich - D3897

Application
2′-Deoxycytidine (deoxyC) is one of the deoxynucleosides which after phosphorylation to dCTP is used to synthesis DNA via various DNA polymerases or reverse transcriptases. 2′-Deoxycytidine (deoxyC) is the substrate for deoxycytidine deaminase (EC 3.5.4.14) which converts it into 2′-deoxyuridine. 2′-Deoxycytidine is phosphorylated to the nucleotide dCMP by the enzyme deoxycytidine kinase (DCK).