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23205-42-7 | 2(1H)-Pyridinone, 4-hydroxy-1-β-D-ribofuranosyl-
CAS No: 23205-42-7 Catalog No: AG002MIL MDL No:
Product Description
Catalog Number:
AG002MIL
Chemical Name:
2(1H)-Pyridinone, 4-hydroxy-1-β-D-ribofuranosyl-
CAS Number:
23205-42-7
Molecular Formula:
C10H13NO6
Molecular Weight:
243.2133
IUPAC Name:
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxypyridin-2-one
InChI:
InChI=1S/C10H13NO6/c12-4-6-8(15)9(16)10(17-6)11-2-1-5(13)3-7(11)14/h1-3,6,8-10,12-13,15-16H,4H2/t6-,8-,9-,10-/m1/s1
InChI Key:
CBOKZNLSFMZJJA-PEBGCTIMSA-N
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1ccc(cc1=O)O
EC Number:
245-488-8
UNII:
263CU738ZY
Properties
Complexity:
379
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1
Defined Atom Stereocenter Count:
4
Defined Bond Stereocenter Count:
0
Exact Mass:
243.074g/mol
Formal Charge:
0
Heavy Atom Count:
17
Hydrogen Bond Acceptor Count:
6
Hydrogen Bond Donor Count:
4
Isotope Atom Count:
0
Molecular Weight:
243.215g/mol
Monoisotopic Mass:
243.074g/mol
Rotatable Bond Count:
2
Topological Polar Surface Area:
111A^2
Undefined Atom Stereocenter Count:
0
Undefined Bond Stereocenter Count:
0
XLogP3:
-1.8
Literature
| Title | Journal |
|---|---|
| Synthesis of C3-arylated-3-deazauridine derivatives with potent anti-HSV-1 activities. | Bioorganic & medicinal chemistry letters 20121215 |
| Introduction of a fluorine atom at C3 of 3-deazauridine shifts its antimetabolic activity from inhibition of CTP synthetase to inhibition of orotidylate decarboxylase, an early event in the de novo pyrimidine nucleotide biosynthesis pathway. | The Journal of biological chemistry 20120831 |
| 3-Deazauridine enhances the antileukemic action of 5-aza-2'-deoxycytidine and targets drug-resistance due to deficiency in deoxycytidine kinase. | Leukemia research 20110101 |
| Synthesis and biological evaluation of 3,3-difluoropyridine-2,4(1H,3H)-dione and 3-deaza-3-fluorouracil base and nucleoside derivatives. | Journal of medicinal chemistry 20090514 |
| The 1.48 A resolution crystal structure of the homotetrameric cytidine deaminase from mouse. | Biochemistry 20060627 |
| 3-Deazauridine triggers dose-dependent apoptosis in myeloid leukemia cells and enhances retinoic acid-induced granulocytic differentiation of HL-60 cells. | The international journal of biochemistry & cell biology 20031001 |
| Potentiation of the anti-HIV activity of zalcitabine and lamivudine by a CTP synthase inhibitor, 3-deazauridine. | Nucleosides, nucleotides & nucleic acids 20000101 |
| Antiviral and cytotoxicity evaluation of 3-nitro-3-deazauridine. | Antiviral research 19891201 |
| Inhibitory effect of selected antiviral compounds on measles (SSPE) virus replication in vitro. | Antiviral research 19890901 |
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