Home Other Building Blocks 5-HYDROXY-2'-DEOXYCYTIDINE

5-HYDROXY-2'-DEOXYCYTIDINE

CAS No.:
52278-77-0
Catalog Number:
AG00DE9R
Molecular Formula:
Molecular Weight:
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Product Description
Catalog Number:
AG00DE9R
Chemical Name:
5-HYDROXY-2'-DEOXYCYTIDINE
CAS Number:
52278-77-0
MDL Number:
MFCD01937860
IUPAC Name:
4-amino-5-hydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]pyrimidin-2-one
InChI:
InChI=1S/C9H13N3O5/c10-8-5(15)2-12(9(16)11-8)7-1-4(14)6(3-13)17-7/h2,4,6-7,13-15H,1,3H2,(H2,10,11,16)/t4-,6+,7+/m0/s1
InChI Key:
CKZJTNZSBMVFSU-UBKIQSJTSA-N
UNII:
6JHE7FC4BX
Properties
Complexity:
394  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
3  
Defined Bond Stereocenter Count:
0
Exact Mass:
243.086g/mol
Formal Charge:
0
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
5  
Hydrogen Bond Donor Count:
4  
Isotope Atom Count:
0
Molecular Weight:
243.219g/mol
Monoisotopic Mass:
243.086g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
129A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.9  
Literature
Title Journal
In vivo treatment with aflatoxin B1 increases DNA oxidation, base excision repair activity and 8-oxoguanine DNA glycosylase 1 levels in mouse lung. Toxicology 20140703
Mutagen-mediated enhancement of HIV-1 replication in persistently infected cells. Virology 20120315
Thermodynamic signature of DNA damage: characterization of DNA with a 5-hydroxy-2'-deoxycytidine·2'-deoxyguanosine base pair. Biochemistry 20120306
Mutation of HIV-1 genomes in a clinical population treated with the mutagenic nucleoside KP1461. PloS one 20110101
Defective repair of 5-hydroxy-2'-deoxycytidine in Cockayne syndrome cells and its complementation by Escherichia coli formamidopyrimidine DNA glycosylase and endonuclease III. Free radical biology & medicine 20100301
Antimicrobial strategies: inhibition of viral polymerases by 3'-hydroxyl nucleosides. Drugs 20090101
Reaction of 2'-deoxycytidine with peroxynitrite in the presence of ammonium bromide. Bioorganic & medicinal chemistry 20080501
Major oxidative products of cytosine are substrates for the nucleotide incision repair pathway. DNA repair 20070104
Synthesis and antiviral activity of 5-substituted cytidine analogues: identification of a potent inhibitor of viral RNA-dependent RNA polymerases. Journal of medicinal chemistry 20061019
Ascorbate and H2O2 induced oxidative DNA damage in Jurkat cells. Free radical biology & medicine 20060615
Oxidation of 5-hydroxypyrimidine nucleosides to 5-hydroxyhydantoin and its alpha-hydroxy-ketone isomer. Chemical research in toxicology 20050801
Combination of a mutagenic agent with a reverse transcriptase inhibitor results in systematic inhibition of HIV-1 infection. Virology 20050720
Effect of chemical modifications of cytosine and guanine in a CpG-motif of oligonucleotides: structure-immunostimulatory activity relationships. Bioorganic & medicinal chemistry 20010301
The role of duck hepatitis B virus and aflatoxin B1 in the induction of oxidative stress in the liver. Cancer detection and prevention 20010101
Lethal mutagenesis of HIV with mutagenic nucleoside analogs. Proceedings of the National Academy of Sciences of the United States of America 19990216
New substrates for old enzymes. 5-Hydroxy-2'-deoxycytidine and 5-hydroxy-2'-deoxyuridine are substrates for Escherichia coli endonuclease III and formamidopyrimidine DNA N-glycosylase, while 5-hydroxy-2'-deoxyuridine is a substrate for uracil DNA N-glycosylase. The Journal of biological chemistry 19940722
Properties