Home Fluorides 316-46-1
316-46-1,MFCD00036832
Catalog No.:AA003MP3

316-46-1 | 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione

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1g
98%(HPLC)
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5g
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$60.00   $42.00
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10g
98%
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$103.00   $73.00
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25g
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100g
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  • Technical Information
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  • Technical Information
  • Properties
  • Literature
Technical Information
Catalog Number:
AA003MP3
Chemical Name:
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione
CAS Number:
316-46-1
Molecular Formula:
C9H11FN2O6
Molecular Weight:
262.1918
MDL Number:
MFCD00036832
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)n1cc(F)c(=O)[nH]c1=O
Properties
Properties
 
Form:
Solid  
MP:
182-184 °C  
Refractive Index:
18 ° (C=1, H2O)  
Storage:
Keep in dry area;Room Temperature;  

Computed Properties
 
Complexity:
414  
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Heavy Atom Count:
18  
Hydrogen Bond Acceptor Count:
7  
Hydrogen Bond Donor Count:
4  
Rotatable Bond Count:
2  
XLogP3:
-1.7  

Literature

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Title: Untargeted metabolomics reveals a lack of synergy between nifurtimox and eflornithine against Trypanosoma brucei.

Journal: PLoS neglected tropical diseases 20120501

Title: A functional genomics approach to establish the complement of carbohydrate transporters in Streptococcus pneumoniae.

Journal: PloS one 20120101

Title: Overexpression of the orotate phosphoribosyl-transferase gene enhances the effect of 5-Fluorouracil in head and neck squamous cell carcinoma in vitro.

Journal: Journal of oncology 20120101

Title: The products of 5-fluorouridine by the action of the pseudouridine synthase TruB disfavor one mechanism and suggest another.

Journal: Journal of the American Chemical Society 20110810

Title: The therapeutic efficacy of S-1 against orthotopically implanted human pleural mesothelioma cells in severe combined immunodeficient mice.

Journal: Cancer chemotherapy and pharmacology 20110801

Title: Equilibrative nucleoside transporter 1 (ENT1) is critical for pollen germination and vegetative growth in Arabidopsis.

Journal: Journal of experimental botany 20110801

Title: Plastid uridine salvage activity is required for photoassimilate allocation and partitioning in Arabidopsis.

Journal: The Plant cell 20110801

Title: Development of miracle medicines from sialic acids.

Journal: Proceedings of the Japan Academy. Series B, Physical and biological sciences 20110610

Title: N⁴-[Alkyl-(hydroxyphosphono)phosphonate]-cytidine-new drugs covalently linking antimetabolites (5-FdU, araU or AZT) with bone-targeting bisphosphonates (alendronate or pamidronate).

Journal: Bioorganic & medicinal chemistry 20110601

Title: Synthesis and biological evaluation of unsaturated keto and exomethylene D-arabinopyranonucleoside analogs: novel 5-fluorouracil analogs that target thymidylate synthase.

Journal: European journal of medicinal chemistry 20110401

Title: The handling of the mechanistic probe 5-fluorouridine by the pseudouridine synthase TruA and its consistency with the handling of the same probe by the pseudouridine synthases TruB and RluA.

Journal: Biochemistry 20110125

Title: Proteinortho: detection of (co-)orthologs in large-scale analysis.

Journal: BMC bioinformatics 20110101

Title: Matrix metalloproteinase-8 mediates the unfavorable systemic impact of local irradiation on pharmacokinetics of anti-cancer drug 5-Fluorouracil.

Journal: PloS one 20110101

Title: Resistance of a rodent malaria parasite to a thymidylate synthase inhibitor induces an apoptotic parasite death and imposes a huge cost of fitness.

Journal: PloS one 20110101

Title: Lipopolysaccharide-Deficient Brucella Variants Arise Spontaneously during Infection.

Journal: Frontiers in microbiology 20110101

Title: Quantitative nucleolar proteomics reveals nuclear re-organization during stress- induced senescence in mouse fibroblast.

Journal: BMC cell biology 20110101

Title: Checkpoint signaling, base excision repair, and PARP promote survival of colon cancer cells treated with 5-fluorodeoxyuridine but not 5-fluorouracil.

Journal: PloS one 20110101

Title: Topical delivery of DNA oligonucleotide to induce p53 generation in the skin via thymidine dinucleotide (pTT)-encapsulated liposomal carrier.

Journal: International journal of nanomedicine 20110101

Title: 13C/15N-19F intermolecular REDOR NMR study of the interaction of TAR RNA with Tat peptides.

Journal: Journal of the American Chemical Society 20101222

Title: Gene annotation and drug target discovery in Candida albicans with a tagged transposon mutant collection.

Journal: PLoS pathogens 20101001

Title: Glycosidic bond conformation preference plays a pivotal role in catalysis of RNA pseudouridylation: a combined simulation and structural study.

Journal: Journal of molecular biology 20100903

Title: PfNT2, a permease of the equilibrative nucleoside transporter family in the endoplasmic reticulum of Plasmodium falciparum.

Journal: The Journal of biological chemistry 20100702

Title: Development and validation of a rapid and sensitive HPLC method for the quantification of 5-fluorocytosine and its metabolites.

Journal: Biomedical chromatography : BMC 20100501

Title: Selective targeting of 2'-deoxy-5-fluorouridine to urokinase positive malignant cells in vitro.

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Title: Glycal formation in crystals of uridine phosphorylase.

Journal: Biochemistry 20100427

Title: Chronic exposure of colorectal cancer cells in culture to fluoropyrimidine analogs induces thymidylate synthase and suppresses p53. A molecular explanation for the mechanism of 5-FU resistance.

Journal: Anticancer research 20100401

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Journal: Neurotoxicity research 20100201

Title: In situ labeling of transcription sites in marine medaka.

Journal: The journal of histochemistry and cytochemistry : official journal of the Histochemistry Society 20100201

Title: Abdominal irradiation modulates 5-Fluorouracil pharmacokinetics.

Journal: Journal of translational medicine 20100101

Title: Stable morphology, but dynamic internal reorganisation, of interphase human chromosomes in living cells.

Journal: PloS one 20100101

Title: Active site conformational dynamics in human uridine phosphorylase 1.

Journal: PloS one 20100101

Title: Phase I/II study of sequential therapy with irinotecan and S-1 for metastatic colorectal cancer.

Journal: British journal of cancer 20091215

Title: TDP-43 localizes in mRNA transcription and processing sites in mammalian neurons.

Journal: Journal of structural biology 20090901

Title: Structure of a functional ribonucleoprotein pseudouridine synthase bound to a substrate RNA.

Journal: Nature structural & molecular biology 20090701

Title: Crystal structure of an RluF-RNA complex: a base-pair rearrangement is the key to selectivity of RluF for U2604 of the ribosome.

Journal: Journal of molecular biology 20090515

Title: Epigenetic reversal of acquired resistance to 5-fluorouracil treatment.

Journal: Molecular cancer therapeutics 20090501

Title: Decreased levels of UMP kinase as a mechanism of fluoropyrimidine resistance.

Journal: Molecular cancer therapeutics 20090501

Title: Evidence for transcriptional activity in the syncytiotrophoblast of the human placenta.

Journal: Placenta 20090401

Title: Structure-activity relationships of orotidine-5'-monophosphate decarboxylase inhibitors as anticancer agents.

Journal: Journal of medicinal chemistry 20090326

Title: Microsatellite instability in colorectal cancer and association with thymidylate synthase and dihydropyrimidine dehydrogenase expression.

Journal: BMC cancer 20090101

Title: Mammalian MCM loading in late-G(1) coincides with Rb hyperphosphorylation and the transition to post-transcriptional control of progression into S-phase.

Journal: PloS one 20090101

Title: Surface-enhanced Raman spectral measurements of 5-fluorouracil in saliva.

Journal: Molecules (Basel, Switzerland) 20081022

Title: African swine fever virus protein p30 interaction with heterogeneous nuclear ribonucleoprotein K (hnRNP-K) during infection.

Journal: FEBS letters 20081015

Title: Molecular characterization of a dual inhibitory and mutagenic activity of 5-fluorouridine triphosphate on viral RNA synthesis. Implications for lethal mutagenesis.

Journal: Journal of molecular biology 20081010

Title: Concentrations of the DNA methyltransferase inhibitor 5-fluoro-2'-deoxycytidine (FdCyd) and its cytotoxic metabolites in plasma of patients treated with FdCyd and tetrahydrouridine (THU).

Journal: Cancer chemotherapy and pharmacology 20080701

Title: Intravesical treatments of bladder cancer: review.

Journal: Pharmaceutical research 20080701

Title: Thymidylate synthase, thymidine phosphorylase and orotate phosphoribosyl transferase levels as predictive factors of chemotherapy in oral squamous cell carcinoma.

Journal: Acta histochemica et cytochemica 20080627

Title: Bisphosphonate derivatives of nucleoside antimetabolites: hydrolytic stability and hydroxyapatite adsorption of 5'-beta,gamma-methylene and 5'-beta,gamma-(1-hydroxyethylidene) triphosphates of 5-fluorouridine and ara-cytidine.

Journal: The Journal of organic chemistry 20080606

Title: Two distinct molecular mechanisms underlying cytarabine resistance in human leukemic cells.

Journal: Cancer research 20080401

Title: Synthesis of chemically functionalized superparamagnetic nanoparticles as delivery vectors for chemotherapeutic drugs.

Journal: Bioorganic & medicinal chemistry 20080315

Title: Efficacy of laser capture microdissection plus RT-PCR technique in analyzing gene expression levels in human gastric cancer and colon cancer.

Journal: BMC cancer 20080101

Title: Suicide gene therapy with the yeast fusion gene cytosine deaminase/uracil phosphoribosyltransferase is not enough for pancreatic cancer.

Journal: Pancreas 20071001

Title: A stochastic view of spliceosome assembly and recycling in the nucleus.

Journal: PLoS computational biology 20071001

Title: Novel and highly regioselective route for synthesis of 5-fluorouridine lipophilic ester derivatives by lipozyme TL IM.

Journal: Journal of biotechnology 20070510

Title: The Escherichia coli protein YjjG is a house-cleaning nucleotidase in vivo.

Journal: FEMS microbiology letters 20070501

Title: Functional characterization of a gene encoding a dual domain for uridine kinase and uracil phosphoribosyltransferase in Arabidopsis thaliana.

Journal: Plant molecular biology 20070301

Title: The fluorouridine insensitive 1 (fur1) mutant is defective in equilibrative nucleoside transporter 3 (ENT3), and thus represents an important pyrimidine nucleoside uptake system in Arabidopsis thaliana.

Journal: The Plant journal : for cell and molecular biology 20070301

Title: Activity and substrate specificity of pyrimidine phosphorylases and their role in fluoropyrimidine sensitivity in colon cancer cell lines.

Journal: The international journal of biochemistry & cell biology 20070101

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Journal: Methods in enzymology 20070101

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Journal: Clinical cancer research : an official journal of the American Association for Cancer Research 20061215

Title: Controlled release of 5-fluorouridine from radiation-crosslinked poly(ethylene-co-vinyl acetate) films.

Journal: Acta biomaterialia 20061101

Title: Mechanistic investigations of the pseudouridine synthase RluA using RNA containing 5-fluorouridine.

Journal: Biochemistry 20061003

Title: The transcriptional regulator CBP has defined spatial associations within interphase nuclei.

Journal: PLoS computational biology 20061001

Title: Evaluations of biomarkers associated with 5-FU sensitivity for non-small-cell lung cancer patients postoperatively treated with UFT.

Journal: British journal of cancer 20060904

Title: Nuclear organization and dynamics of transcription sites in rat sensory ganglia neurons detected by incorporation of 5'-fluorouridine into nascent RNA.

Journal: Neuroscience 20060630

Title: Identification of inhibitors of ribozyme self-cleavage in mammalian cells via high-throughput screening of chemical libraries.

Journal: RNA (New York, N.Y.) 20060501

Title: Identification of AtENT3 as the main transporter for uridine uptake in Arabidopsis roots.

Journal: Cell research 20060401

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Journal: Bioorganic & medicinal chemistry letters 20060215

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Journal: Bioorganic & medicinal chemistry 20051215

Title: Combined tumor therapy by using radiofrequency ablation and 5-FU-laden polymer implants: evaluation in rats and rabbits.

Journal: Radiology 20051201

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Journal: Nucleosides, nucleotides & nucleic acids 20041001

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Journal: Pharmacological research 20040801

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Journal: The Journal of physiology 20040801

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Journal: Journal of cancer research and clinical oncology 20040801

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Journal: British journal of cancer 20031020

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Journal: Journal of pharmaceutical and biomedical analysis 20020601

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Journal: The Journal of pharmacy and pharmacology 20020601

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SDS
Tags:316-46-1 Molecular Formula|316-46-1 MDL|316-46-1 SMILES|316-46-1 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-fluoro-1,2,3,4-tetrahydropyrimidine-2,4-dione