Structure via PubChem · Public domain (PubChem)
4-deoxyuridine
Sign in to saveAlso known as 1-beta-D-ribofuranosyl-2(1H)-pyrimidinone, pyrimidin-2-one ribonucleoside, pyrimidin-2-one beta-D-ribofuranoside, Zebularine, pyrimidin-2-one beta-ribofuranoside, 1-beta-D-ribofuranosylpyrimidin-2(1H)-one, Pyrimidin-2-one beta-D-ribofuranoside, DHZ
Zebularine is a nucleoside analog of cytidine. It is a transition state analog inhibitor of cytidine deaminase by binding to the active site as covalent hydrates. Also shown to inhibit DNA methylation and tumor growth both in vitro and in vivo.
Chemical data
- Formula
- C9H12N2O5
- Molecular weight
- 228.2 g/mol
- IUPAC name
- 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
- SMILES
- C1=CN(C(=O)N=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
- InChIKey
- RPQZTTQVRYEKCR-WCTZXXKLSA-N
- XLogP
- -1.5
- Polar surface area
- 103 Ų
- H-bond donors
- 3
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 228.075
Show 4 more facts
- chemical formula
- C₉H₁₂N₂O₅
- isomeric SMILES
- C1=CN(C(=O)N=C1)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
- canonical SMILES
- C1=CN(C(=O)N=C1)C2C(C(C(O2)CO)O)O
- Commons category
- Zebularine
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Zebularine is a nucleoside analog of cytidine. It is a transition state analog inhibitor of cytidine deaminase by binding to the active site as covalent hydrates. Also shown to inhibit DNA methylation and tumor growth both in vitro and in vivo.
In a small study of mice with a defective Adenomatous polyposis coli gene, oral administration of zebularine to males had no effect on the overall methylation of DNA or the number of polyps, but in females the average number of polyps was reduced from 58 to 1. It has therefore been suggested for drug use as a prototype of epigenetic therapy for cancer chemoprevention.
Excerpted from Wikipedia’s “4-deoxyuridine” article, available under the CC BY-SA 4.0 licence.