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18771-50-1

18771-50-1 | Tetrahydrouridine

CAS No: 18771-50-1 Catalog No: AG0038WM MDL No:

Product Description

Catalog Number:
AG0038WM
Chemical Name:
Tetrahydrouridine
CAS Number:
18771-50-1
Molecular Formula:
C9H16N2O6
Molecular Weight:
248.2331
IUPAC Name:
1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-hydroxy-1,3-diazinan-2-one
InChI:
InChI=1S/C9H16N2O6/c12-3-4-6(14)7(15)8(17-4)11-2-1-5(13)10-9(11)16/h4-8,12-15H,1-3H2,(H,10,16)/t4-,5?,6-,7-,8-/m1/s1
InChI Key:
UCKYOOZPSJFJIZ-XVKVHKPRSA-N
SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O)O)N1CCC(NC1=O)O

Properties

Complexity:
301  
Compound Is Canonicalized:
Yes
Covalently-Bonded Unit Count:
1  
Defined Atom Stereocenter Count:
4  
Defined Bond Stereocenter Count:
0
Exact Mass:
248.101g/mol
Formal Charge:
0
Heavy Atom Count:
17  
Hydrogen Bond Acceptor Count:
6  
Hydrogen Bond Donor Count:
5  
Isotope Atom Count:
0
Molecular Weight:
248.235g/mol
Monoisotopic Mass:
248.101g/mol
Rotatable Bond Count:
2  
Topological Polar Surface Area:
123A^2
Undefined Atom Stereocenter Count:
1  
Undefined Bond Stereocenter Count:
0
XLogP3:
-2.4  

Literature

Title Journal
Epigenetic regulation by decitabine of melanoma differentiation in vitro and in vivo. International journal of cancer 20120701
Effects of tetrahydrouridine on pharmacokinetics and pharmacodynamics of oral decitabine. Blood 20120202
Tetrahydrouridine inhibits cell proliferation through cell cycle regulation regardless of cytidine deaminase expression levels. PloS one 20120101
Comparison of in vitro metabolic conversion of capecitabine to 5-FU in rats, mice, monkeys and humans--toxicological implications. The Journal of toxicological sciences 20110801
Plasma pharmacokinetics and oral bioavailability of the 3,4,5,6-tetrahydrouridine (THU) prodrug, triacetyl-THU (taTHU), in mice. Cancer chemotherapy and pharmacology 20110201
An APCI LC-MS/MS method for routine determination of capecitabine and its metabolites in human plasma. Journal of mass spectrometry : JMS 20100601
Stability of 5-fluoro-2'-deoxycytidine and tetrahydrouridine in combination. AAPS PharmSciTech 20100301
Is the resistance of gemcitabine for pancreatic cancer settled only by overexpression of deoxycytidine kinase? Oncology reports 20100201
Synthesis of deoxytetrahydrouridine. The Journal of organic chemistry 20090306
Plasma pharmacokinetics and oral bioavailability of 3,4,5,6-tetrahydrouridine, a cytidine deaminase inhibitor, in mice. Cancer chemotherapy and pharmacology 20080801
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). Cancer chemotherapy and pharmacology 20080701
Optimized blood sampling with cytidine deaminase inhibitor for improved analysis of capecitabine metabolites. Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 20080701
Modulation of gemcitabine (2',2'-difluoro-2'-deoxycytidine) pharmacokinetics, metabolism, and bioavailability in mice by 3,4,5,6-tetrahydrouridine. Clinical cancer research : an official journal of the American Association for Cancer Research 20080601
Quantitative determination of the cytidine deaminase inhibitor tetrahydrouridine (THU) in mouse plasma by liquid chromatography/electrospray ionization tandem mass spectrometry. Rapid communications in mass spectrometry : RCM 20070101
The 1.48 A resolution crystal structure of the homotetrameric cytidine deaminase from mouse. Biochemistry 20060627
Relatively small increases in the steady-state levels of nucleobase deamination products in DNA from human TK6 cells exposed to toxic levels of nitric oxide. Chemical research in toxicology 20060101
Structure of human cytidine deaminase bound to a potent inhibitor. Journal of medicinal chemistry 20050210
Molecular characterization of thymidine kinase from Ureaplasma urealyticum: nucleoside analogues as potent inhibitors of mycoplasma growth. Molecular microbiology 20031101
Epimer interconversion, isomerization, and hydrolysis of tetrahydrouridine: implications for cytidine deaminase inhibition. Journal of pharmaceutical sciences 20031001
Analytical and pharmacokinetic studies with 5-chloro-2'-deoxycytidine. Biochemical pharmacology 20021115
Five-chlorodeoxycytidine, a tumor-selective enzyme-driven radiosensitizer, effectively controls five advanced human tumors in nude mice. International journal of radiation oncology, biology, physics 20011101
Regulatory effects of deoxyribonucleosides on the activity of 5-methoxymethyl-2'-deoxycytidine: modulation of antiherpes activity by deoxyguanosine and tetrahydrodeoxyuridine. Antiviral research 19910501
Antiherpes virus activity and effect on deoxyribonucleoside triphosphate pools of (E)-5-(2-bromovinyl)-2'-deoxycytidine in combination with deaminase inhibitors. Antiviral research 19900301

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