2',3'-Dideoxyuridine

HCID 65161CAS 5983-09-5

Substructure search Find similar structures

Basic information

Standard SMILES: O=c1ccn([C@H]2CC[C@@H](CO)O2)c(=O)[nH]1
InChIKey: BTOTXLJHDSNXMW-POYBYMJQSA-N
Molecular formula: C9H12N2O4
Average molar mass: 212.2 g/mol
Monoisotopic mass: 212.07970686

Overview

2,3-dideoxyuridine is a pyrimidine 2',3'-dideoxyribonucleoside.

Names & identifiers

Preferred name: 2',3'-Dideoxyuridine
IUPAC: 1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
English name: 2',3'-Dideoxyuridine
Molecular formula: C9H12N2O4
Molecular weight: 212.2

Names & synonyms

2',3'-Dideoxyuridine5983-09-5DTXSID90208558RefChem:908374DTXCID40131049Uridine, 2',3'-dideoxy-1-[(2R,5S)-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dioneMFCD00013359Dideoxyuridine2,3-Dideoxyuridine2',3'-Dideoxyuridine, 98%1-((2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

Show more names

DDU2',3'-ddU2,3’-Dideoxyuridine2',3'-Dideoxy-D-uridine2',3'-Dideoxyuridine 98%BETA-D-2',3'-DIDEOXYURIDINE2'', 3''-DIDEOXYURIDINE (DDU)

HY-W014306AC-321851-[(2R,5S)-5-(hydroxymethyl)tetrahydrofuran-2-yl]pyrimidine-2,4-dioneddUrd2',3'-dideoxy-uridine2', 3'-Dideoxyuridine1-(2',3'-Dideoxy-beta-ribofuranosyl)uracilSCHEMBL8715

Database identifiers

CAS: 5983-09-5
PubChem CID: 65161
DTXSID: DTXSID90208558
ChEMBL: CHEMBL1468
ChEBI: CHEBI:183866
Nikkaji: J353.479K

Properties

Computed structural properties

XLogP: -0.9
Topological polar surface area: 78.9 Å²
Hydrogen bond donors: 2
Hydrogen bond acceptors: 4
Rotatable bonds: 2
Heavy atoms: 15
Formal charge: 0
Complexity: 315

Physicochemical properties

Melting point: 127 · 127-129 °C(lit.)
alpha: 34 · 34 º (C=0.4 IN H2O)
Density: 1.397 · 1.397±0.06 g/cm3(Predicted)
storage temp.: 2 · Sealed in dry,2-8°C
solubility: 10 mg/ml; · DMF: 10 mg/ml; DMSO: 10 mg/ml; Ethanol: Slightly soluble; PBS (pH 7.2): 5 mg/ml
form: A solid
pka: 9.39 · 9.39±0.10(Predicted)
color: White to off-white
optical activity: 20 · [α]20/D +34°, c = 0.4 in H2O
BRN: 750592 · 750592
InChI: InChI=1S/C9H12N2O4/c12-5-6-1-2-8(15-6)11-4-3-7(13)10-9(11)14/h3-4,6,8,12H,1-2,5H2,(H,10,13,14)/t6-,8+/m0/s1
InChIKey: BTOTXLJHDSNXMW-POYBYMJQSA-N
SMILES: OC[C@H]1O[C@@H](N2C=CC(=O)NC2=O)CC1
CAS DataBase Reference: 5983 · 5983-09-5(CAS DataBase Reference)
UNSPSC Code: 12352100 · 12352100
NACRES: 22 · NA.22
Symbol(GHS): 7 · GHS07
Signal word: Warning
Hazard statements: 302 · H302-H315-H319-H332-H335
Precautionary statements: 261 · P261-P280-P305+P351+P338
PPE: 95 · Eyeshields, Gloves, type N95 (US)
Hazard Codes: C
Risk Statements: 34 · 34-36/37
Safety Statements: 22 · 22-24/25-45-36/37/39-27-26
WGK Germany: 3 · 3
F: 10 · 10-23
HS Code: 29349990 · 29349990
Storage Class: 11 · 11 - Combustible Solids

Safety & regulation

Safety data

F: 10-23
PPE: Eyeshields, Gloves, type N95 (US)
wgk: 3
hs_code: 29349990
risk_code: 34-36/37
Signal word: Warning
Symbol(GHS): GHS07
hazard_code: C
safety_code: 22-24/25-45-36/37/39-27-26
Storage Class: 11 - Combustible Solids
Hazard statements: H302-H315-H319-H332-H335
Precautionary statements: P261-P280-P305+P351+P338

Chemistry & industry

Applications

Uses2’,3’-Dideoxyuridine can be used as prodrug precursors or in antisense oligonucleotide synthesis. Also, it can be used to synthesize ProTide derivatives and evaluated against HIV-1 and HIV-2.

UsesResearch tool for antiviral and anticancer studies.