Compounds > cyclopentenyluracil
Page last updated: 2024-12-07

cyclopentenyluracil

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

cyclopentenyluracil: does not have antiviral acitivity in contrast to cyclopentenylcytosine; RN given refers to (1R-(1alpha,4beta,5beta)-isomer); RN for cpd without isomeric designation not avail 6/91 [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID128937
CHEMBL ID1966557
SCHEMBL ID12280146
MeSH IDM0188452

Synonyms (20)

Synonym
NCI60_003527
nsc-375574
nsc375574
cyclopentenyluracil
cyclopentenyluridine
2,3h)-pyrimidinedione, 1-[4,5-dihydroxy- 3-(hydroxymethyl)-2-cyclopenten-1-yl]-
1-[(1r,4r,5s)-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl]pyrimidine-2,4-dione
(1'r,2's,3'r)-1-[2,3-dihydroxy-4-hydroxymethyl-4-cyclopenten-1-yl]uracil
cyclopentenyl uracil
90597-20-9
1-(4,5-dihydroxy-3-hydroxymethyl-cyclopent-2-enyl)-4-hydroxy-1h-pyrimidin-2-one
chembl1966557 ,
bdbm50026671
ce-urd
2,4(1h,3h)-pyrimidinedione, 1-(4,5-dihydroxy-3-(hydroxymethyl)-2-cyclopenten-1-yl)-, (1r-(1alpha,4beta,5beta))-
SCHEMBL12280146
MS-23398
1-((1r,4r,5s)-4,5-dihydroxy-3-(hydroxymethyl)cyclopent-2-en-1-yl)pyrimidine-2,4(1h,3h)-dione
HY-145668
CS-0378522

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" Dose-response characteristics of the inhibition were determined."( Cyclopentenyl uracil: an effective inhibitor of uridine salvage in vivo.
August, EM; Cysyk, RL; Malinowski, N; Marquez, V; Moyer, JD; Zaharevitz, D, 1995)		0.29
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
cytoskeleton organizationFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
signal transductionFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
regulation of cell shapeFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
animal organ morphogenesisFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
actin cytoskeleton organizationFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
regulation of GTPase activityFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
filopodium assemblyFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
regulation of small GTPase mediated signal transductionFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
guanyl-nucleotide exchange factor activityFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
small GTPase bindingFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
metal ion bindingFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
ruffleFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
cytoplasmFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
Golgi apparatusFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
cytosolFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
cytoskeletonFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
lamellipodiumFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
cytoplasmFYVE, RhoGEF and PH domain-containing protein 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID215625Inhibition of uridine kinase from L1210 cells was evaluated by measuring the retention of phosphorylated product on DE81 filter papers at 100 uM1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Cyclopentenyluridine and cyclopentenylcytidine analogues as inhibitors of uridine-cytidine kinase.
AID152792In vitro cytotoxicity in PBM cells.2001Journal of medicinal chemistry, Nov-08, Volume: 44, Issue:23
Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus.
AID47445In vitro cytotoxicity in CEM cells.2001Journal of medicinal chemistry, Nov-08, Volume: 44, Issue:23
Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus.
AID98880Compound was tested for its ability to inhibit L1210 cell growth after 72 hr at 100 uM concentration1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Cyclopentenyluridine and cyclopentenylcytidine analogues as inhibitors of uridine-cytidine kinase.
AID215628Binding affinity to uridine kinase from L1210. was determined from the dixon plot1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Cyclopentenyluridine and cyclopentenylcytidine analogues as inhibitors of uridine-cytidine kinase.
AID152622In vitro antiviral activity against HIV-1 in human PBM cells.2001Journal of medicinal chemistry, Nov-08, Volume: 44, Issue:23
Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus.
AID216278In vitro antiviral activity against West Nile Virus.2001Journal of medicinal chemistry, Nov-08, Volume: 44, Issue:23
Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus.
AID98879Compound was tested for its ability to inhibit L1210 cell growth after 72 hr at 1000 uM concentration1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Cyclopentenyluridine and cyclopentenylcytidine analogues as inhibitors of uridine-cytidine kinase.
AID217742In vitro cytotoxicity in vero cells.2001Journal of medicinal chemistry, Nov-08, Volume: 44, Issue:23
Enantiomeric synthesis of D- and L-cyclopentenyl nucleosides and their antiviral activity against HIV and West Nile virus.
AID215626Inhibition of uridine kinase from L1210 cells was evaluated by measuring the retention of phosphorylated product on DE81 filter papers at 1000 uM1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Cyclopentenyluridine and cyclopentenylcytidine analogues as inhibitors of uridine-cytidine kinase.
AID98881Compound was tested for its ability to inhibit L1210 cell growth after 72 hr at 500 uM concentration1984Journal of medicinal chemistry, Dec, Volume: 27, Issue:12
Cyclopentenyluridine and cyclopentenylcytidine analogues as inhibitors of uridine-cytidine kinase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (14.29)18.7374
1990's3 (42.86)18.2507
2000's2 (28.57)29.6817
2010's1 (14.29)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.57

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.57 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.65 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.57)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
uracil
2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder		3.150pyrimidine nucleobase;
pyrimidone		allergen;
Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
prodrug;
Saccharomyces cerevisiae metabolite
fluorouracil
Fluorouracil: A pyrimidine analog that is an antineoplastic antimetabolite. It interferes with DNA synthesis by blocking the THYMIDYLATE SYNTHETASE conversion of deoxyuridylic acid to thymidylic acid.. 5-fluorouracil : A nucleobase analogue that is uracil in which the hydrogen at position 5 is replaced by fluorine. It is an antineoplastic agent which acts as an antimetabolite - following conversion to the active deoxynucleotide, it inhibits DNA synthesis (by blocking the conversion of deoxyuridylic acid to thymidylic acid by the cellular enzyme thymidylate synthetase) and so slows tumour growth.		1.9710nucleobase analogue;
organofluorine compound		antimetabolite;
antineoplastic agent;
environmental contaminant;
immunosuppressive agent;
radiosensitizing agent;
xenobiotic
thymidine
[no description available]		1.9710pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
metabolite;
mouse metabolite
azauridine
Azauridine: A triazine nucleoside used as an antineoplastic antimetabolite. It interferes with pyrimidine biosynthesis thereby preventing formation of cellular nucleic acids. As the triacetate, it is also effective as an antipsoriatic.		2.3920N-glycosyl-1,2,4-triazineantimetabolite;
antineoplastic agent;
drug metabolite
uridine
[no description available]		1.9810uridinesdrug metabolite;
fundamental metabolite;
human metabolite
cytidine
[no description available]		2.6830cytidinesEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
cytarabine
[no description available]		1.9710beta-D-arabinoside;
monosaccharide derivative;
pyrimidine nucleoside		antimetabolite;
antineoplastic agent;
antiviral agent;
immunosuppressive agent
deoxycytidine
[no description available]		1.9710pyrimidine 2'-deoxyribonucleosideEscherichia coli metabolite;
human metabolite;
mouse metabolite;
Saccharomyces cerevisiae metabolite
zidovudine
Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.		210azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
ribavirin
Rebetron: Rebetron is tradename		1.97101-ribosyltriazole;
aromatic amide;
monocarboxylic acid amide;
primary carboxamide		anticoronaviral agent;
antiinfective agent;
antimetabolite;
antiviral agent;
EC 2.7.7.49 (RNA-directed DNA polymerase) inhibitor
adenosine
quinquefolan B: isolated from roots of Panax quinquefolium L.; RN not in Chemline 10/87; RN from Toxlit		1.9710adenosines;
purines D-ribonucleoside		analgesic;
anti-arrhythmia drug;
fundamental metabolite;
human metabolite;
vasodilator agent
cyclopentenyl cytosine
cyclopentenyl cytosine: inhibits CTP synthetase; used in therapy of colonic neoplasms; structure given in first source; RN given refers to the (1R-(1alpha,4beta,5beta))-isomer		3.0850
neplanocin a
neplanocin A: neplanocins are antitumor antibiotics & carbocyclic analogs of purine nucleosides from Ampullarilla regularis A11079; see also neplanocin B, neplanocin C, neplanocin D & neplanocin F; structure in first source; a potent inhibitor of S-adenosylhomocysteine hydrolase		2.3920
carbodine
carbodine: RN given refers to (R-(1alpha,2beta,3beta,4alpha))-isomer		1.9710
ribose
ribopyranose : The pyranose form of ribose.		1.9710D-ribose;
ribopyranose
pyrazofurin
pirazofurin : A C-glycosyl compound that is 4-hydroxy-1H-pyrazole-5-carboxamide in which the hydrogen at position 3 has been replaced by a beta-D-ribofuranosyl group.		1.9710C-glycosyl compound;
pyrazoles		antimetabolite;
antimicrobial agent;
antineoplastic agent;
EC 4.1.1.23 (orotidine-5'-phosphate decarboxylase) inhibitor
ConditionIndicatedRelationship StrengthStudiesTrials
Leukemia L 1210
[description not available]		02.3820
Leucocythaemia
[description not available]		01.9810
Leukemia
A progressive, malignant disease of the blood-forming organs, characterized by distorted proliferation and development of leukocytes and their precursors in the blood and bone marrow. Leukemias were originally termed acute or chronic based on life expectancy but now are classified according to cellular maturity. Acute leukemias consist of predominately immature cells; chronic leukemias are composed of more mature cells. (From The Merck Manual, 2006)		01.9810