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Basic information
- CAS
3690-10-6- Standard SMILES
O=c1ncccn1[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O- InChIKey
RPQZTTQVRYEKCR-WCTZXXKLSA-N- Molecular formula
- C9H12N2O5
- Average molar mass
- 228.2 g/mol
- Monoisotopic mass
- 228.07462149
Names & identifiers
- Preferred name
- Zebularine
- IUPAC
- 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
- English name
- ZEBULARINE
- Molecular formula
- C9H12N2O5
- Molecular weight
- 228.2
Names & synonyms
Zebularine3690-10-64-DeoxyuridinePyrimidin-2-one ribonucleosidePyrimidin-2-one beta-ribofuranosidePyrimidin-2-one beta-D-ribofuranoside1-beta-D-ribofuranosylpyrimidin-2(1H)-one2(1H)-Pyrimidinone, 1-beta-D-ribofuranosyl-NSC 3091321-beta-D-ribofuranosyl-2(1H)-pyrimidinone7A9Y5SX0GYCHEBI:46938
Show more names
1-(β-d-ribofuranosyl)-1,2-dihydropyrimidin-2-one1-(β-d-ribofuranosyl)-1,2-dihydropyrimidin-2-one4-Deoyuridineanticancer drug, DNAZebularine ZebularineZebularine (NSC3091324-Deoyuridine,Zebularine
NSC-3091321-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-1,2-dihydropyrimidin-2-oneNSC3091321-((2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl)-1,2-dihydropyrimidin-2-oneRefChem:9048222-Pyrimidone-1-beta-D-ribosideMFCD049736991-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
Database identifiers
- CAS
3690-10-6
Properties
Computed structural propertiesFilling in
- XLogP
- -1.5
- Topological polar surface area
- 103 Ų
- Hydrogen bond donors
- 3
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 2
- Heavy atoms
- 16
- Formal charge
- 0
- Complexity
- 343
Physicochemical properties
- Melting point
- 160 · 160-162C
- Boiling point
- 499 · 499.0±55.0 °C(Predicted)
- Density
- 1.73 · 1.73±0.1 g/cm3(Predicted)
- storage temp.
- 2 · 2-8°C
- solubility
- 16 mg/mL, · DMSO: 16 mg/mL, soluble
- form
- solid
- pka
- 13.48 · 13.48±0.70(Predicted)
- color
- White
- Stability
- 2 years · Stable for 2 years from date of purchase as supplied. Solutions in DMSO or distilled water may be stored at -20° for up to 1 month.
- InChI
- InChI=1/C9H12N2O5/c12-4-5-6(13)7(14)8(16-5)11-3-1-2-10-9(11)15/h1-3,5-8,12-14H,4H2/t5-,6-,7-,8-/s3
- InChIKey
- RPQZTTQVRYEKCR-WCTZXXKLSA-N
- SMILES
- N1(C=CC=NC1=O)[C@@H]1O[C@H](CO)[C@@H](O)[C@H]1O |&1:7,9,12,14,r|
- FDA UNII
- 7 A9Y5SX0GY · 7A9Y5SX0GY
- UNSPSC Code
- 12352203 · 12352203
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- PPE
- Eyeshields, Gloves, type N95 (US)
- wgk
- 3
- rtecs
- UW7539720
- hs_code
- 2934999090
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Storage Class
- 11 - Combustible Solids
- Hazard statements
- H302-H315-H320-H335
- Precautionary statements
- P264-P270-P301+P312-P330
Chemistry & industry
Applications
DescriptionZebularine (3690-10-6) is an orally active DNA methyltransferase inhibitor. Inhibits tumor cell proliferation (IC50 = 120 μM) and re-activates silenced genes in T24 bladder carcinoma cells. Zebularine inhibits cytidine deaminase (Ki ~ 2 μM and; induces differentiation of mesenchymal stem cells into cardiomyocytes.
UsesIt is a cytidine analogue, cytidine deaminase inhibitor, and DNA demethylating agent.
Upstream & downstream products
Upstream raw materials
Suppliers98 total
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
武汉英诺医药科技有限公司+86-027-59232304 15387063101 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
成都彼样生物科技有限公司18108052721 · [email protected]
河南赢创生物科技有限公司
Related reactions
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Compound notes
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