Basic information
- Standard SMILES
[N-]=[N+]=N[C@H]1C[C@H](n2ccc(=O)[nH]c2=O)O[C@@H]1CO- InChIKey
ZSNNBSPEFVIUDS-SHYZEUOFSA-N- Molecular formula
- C9H11N5O4
- Average molar mass
- 253.22 g/mol
- Monoisotopic mass
- 253.08110383
Overview
Navuridine is a dideoxyuridine inhibitor of HIV reverse transcriptase that is related to zidovudine. Navuridine exhibits a relatively short half-life and incomplete oral bioavailability and has not been developed into a clinical drug.
Names & identifiers
- Preferred name
- Navuridine
- IUPAC
- 1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
Names & synonyms
Navuridine84472-85-5AZdU3'-AZIDO-2',3'-DIDEOXYURIDINEAZddUCS-87NavuridinaUridine, 3'-azido-2',3'-dideoxy-NSC-380882PS28W654793'-azido-2',3'dideoxyuridinenavuridinum
Show more names
NSC380882RefChem:9275253'-azido-2'-3'-dideoxyuridineNavuridine [INN]1-((2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dioneMFCD008703241-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dioneAzUrd
Database identifiers
- CAS
84472-85-5- PubChem CID
- 55262
- DTXSID
DTXSID901004737- ChEMBL
CHEMBL591804- UNII
- PS28W65479
- Nikkaji
- J329.218E
Properties
Computed structural properties
- XLogP
- -0.3
- Topological polar surface area
- 93.2 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 3
- Heavy atoms
- 18
- Formal charge
- 0
- Complexity
- 444
Experimental & physicochemical properties
SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP-0.37
Related reactions
7 records
Linked notes
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