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5'-Azido-5'-deoxythymidine

CAT: 0804-HY-131612Size: 1 EachDry Ice: NoHazardous: No
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Description
5'-Azido-5'-deoxythymidine (Compound 7), a nucleoside analogue, is a reverse transcriptase inhibitor. 5'-Azido-5'-deoxythymidine mimics nucleosides and is incorporated into the viral DNA chain to terminate chain elongation, inhibiting viral replication. 5'-Azido-5'-deoxythymidine is promising for research of retroviral infection diseases such as AIDS[1][2].
CAS Number
19316-85-9
UNSPSC
12352005
Target
Reverse Transcriptase
Related Pathways
Anti-infection
Field of Research
Infection
Smiles
O=C(C(C)=CN1[C@H]2C[C@H](O)[C@@H](CN=[N+]=[N-])O2)NC1=O
Molecular Formula
C10H13N5O4
Molecular Weight
267.24
References & Citations
[1]Neenan JP, Rohde W. Inhibition of thymidine kinase from Walker 256 carcinoma by thymidine analogs. J Med Chem. 1973 May;16 (5) :580-1.|[2]Baraniak D. Synthesis of nucleoside-cinchona alkaloid conjugates via" click" chemistry[D]. Zakład Chemii Medycznej [nowa struktura organizacyjna], 2012.
Shipping Conditions
Room temperature
Scientific Category
Reference compound1
Clinical Information
No Development Reported

Chemical Information

Thymidine, 5'-azido-5'-deoxy-
CAS Number19316-85-9
PubChem CID451456
IUPAC Name1-[(2R,4S,5R)-5-(azidomethyl)-4-hydroxyoxolan-2-yl]-5-methylpyrimidine-2,4-dione
Molecular FormulaC10H13N5O4
Molecular Weight267.24
XLogP-0.1
Topological Polar Surface Area93.2
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count3
Heavy Atom Count19
Formal Charge0
Complexity484
SMILES
CC1=CN(C(=O)NC1=O)[C@H]2C[C@@H]([C@H](O2)CN=[N+]=[N-])O
InChI
InChI=1S/C10H13N5O4/c1-5-4-15(10(18)13-9(5)17)8-2-6(16)7(19-8)3-12-14-11/h4,6-8,16H,2-3H2,1H3,(H,13,17,18)/t6-,7+,8+/m0/s1
InChIKey
GKEHVJFBPNPCKI-XLPZGREQSA-N
Chemical Structure
2D Structure
2D structure of Thymidine, 5'-azido-5'-deoxy-
CAS: 19316-85-9
CID: 451456
Formula: C10H13N5O4
MW: 267.24
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight267.24
XLogP3-0.1
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count3
Exact Mass267.09675391
Monoisotopic Mass267.09675391
Topological Polar Surface Area93.2 Ų
Heavy Atom Count19
Formal Charge0
Complexity484
Isotope Atom Count0
Defined Atom Stereocenter Count3
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

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