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Merck
CN

SML2972

Cyclopentenyl uracil

≥98% (HPLC)

Synonym(s):

1-[(1R,4R,5S)-4,5-Dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl]-2,4(1H,3H)-pyrimidinedione, Cyclopentenyluracil, Cyclopentenyluridine, NSC 375574

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About This Item

Empirical Formula (Hill Notation):
C10H12N2O5
CAS Number:
90597-20-9
Molecular Weight:
240.21
UNSPSC Code:
51111800
NACRES:
NA.77

Key Documents

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SMILES string

[nH]1[c]([n](cc[c]1=O)[C@H]2[C@@H]([C@@H](C(=C2)CO)O)O)=O

InChI

1S/C10H12N2O5/c13-4-5-3-6(9(16)8(5)15)12-2-1-7(14)11-10(12)17/h1-3,6,8-9,13,15-16H,4H2,(H,11,14,17)/t6-,8-,9+/m1/s1

InChI key

FCWVOJUKQSHZIV-VDAHYXPESA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Related Categories

Biochem/physiol Actions

Cyclopentenyl uracil is a non-cytotoxic inhibitor of uridine kinase that act as a potent inhibitor of pyrimidine salvage in the intact mouse. Combination of Cyclopentenyl uracil with GSK983 significantly reduces viral infection of dengue serotype 2 (DENV-2) strain 16681 in cultures of the A549 lung carcinoma cell line. Cyclopentenyl uracil in combination with GSK983 enhances therapeutic index of viral RdRp inhibitor R1479.
non-cytotoxic inhibitor of uridine kinase that act as a potent inhibitor of pyrimidine salvage

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Regulatory Information

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Certificates of Analysis (COA)

Lot/Batch Number
0000119928
0000119929
0000112012

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R L Cysyk et al.
Biochemical pharmacology, 49(2), 203-207 (1995-01-18)
Cyclopentenyl uracil, a non-cytotoxic inhibitor of uridine kinase, was found to effectively block the salvage of circulating uridine by host and tumor tissues in the intact mouse. Dose-response characteristics of the inhibition were determined. Large doses (1 g/kg) of cyclopentenyl
Qi Liu et al.
Cell chemical biology, 27(6), 668-677 (2020-05-23)
Genome-wide analysis of the mode of action of GSK983, a potent antiviral agent, led to the identification of dihydroorotate dehydrogenase as its target along with the discovery that genetic knockdown of pyrimidine salvage sensitized cells to GSK983. Because GSK983 is an

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