Page last updated: 2024-11-05

cyclopentenone

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

Description

Cyclopentenone is a five-membered cyclic ketone with a double bond in the ring. It is an important building block in organic synthesis and occurs in a variety of natural products, including prostaglandins, which are hormone-like substances that regulate various physiological processes. Cyclopentenone and its derivatives have been shown to exhibit a range of biological activities, including anti-inflammatory, anticancer, and antimicrobial properties. The presence of the enone system (a conjugated double bond and carbonyl group) makes cyclopentenone susceptible to electrophilic attack, allowing for a variety of chemical transformations. Its reactivity and structural versatility make it a valuable intermediate in the synthesis of complex molecules.'

2-cyclopenten-1-one : An enone that is cyclopentanone having a C=C double bond at position 2. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID13588
CHEMBL ID52190
CHEBI ID141550
MeSH IDM0062037

Synonyms (48)

Synonym
EN300-24545
cyclopentenone
930-30-3
3-cyclopenten-2-one
nsc-73117
cyclopenten-3-one
2-cyclopentenone
nsc73117
inchi=1/c5h6o/c6-5-3-1-2-4-5/h1,3h,2,4h
2-cyclopenten-1-one
cyclopent-2-en-1-one
2-cyclopenten-1-one, 98%
CHEMBL52190
CHEBI:141550
cyclopent-2-enone
AKOS000121108
A844427
einecs 213-213-0
nsc 73117
unii-q0u2igf9ck
cyclopenten-3-one (van)
q0u2igf9ck ,
cyclopent-2-ene-1-one
28982-58-3
2-cylcopenten-1-one
2-cyclopentene-1-one
FT-0625674
FT-0649567
FT-0606447
AM61702
1-cyclopenten-5-one
1-cyclopenten-3-one
2-cyclopenten-1- one
cyclopenten-2-one
AKOS025243944
CS-W011359
2-cyclopentenone-1
PS-9373
J-520173
F0001-2242
mfcd00001401
Q2292678
DTXSID60870802
STL183308
BBL100014
cis-cyclopentenone
SB40642
HY-W010643

Research Excerpts

Effects

ExcerptReferenceRelevance
"Cyclopentenones have been shown to be versatile intermediates for the stereoselective preparation of highly substituted cyclopentane derivatives."( Investigation into 9(S)-HPODE-derived allene oxide to cyclopentenone cyclization mechanism via diradical oxyallyl intermediates.
Brash, AR; Cha, JK; Hebert, SP; Schlegel, HB, 2016
)
1.4

Actions

Cyclopentenone prostanoids inhibit virus replication by turning on an intracellular defence response. IsoPs enhance neurodegeneration caused by other insults at biologically relevant concentrations.

ExcerptReferenceRelevance
"Cyclopentenone IsoPs also enhance neurodegeneration caused by other insults at biologically relevant concentrations."( Electrophilic cyclopentenone isoprostanes in neurodegeneration.
McLaughlin, B; Morrow, JD; Musiek, ES, 2007
)
1.42
"Cyclopentenone prostanoids inhibit virus replication by turning on an intracellular defence response that involves the induction of cytoprotective heat-shock proteins, the modification of viral glycoprotein maturation and the control of NF-kappa B activation. "( Antiviral activity of cyclopentenone prostanoids.
Santoro, MG, 1997
)
2.05

Dosage Studied

ExcerptRelevanceReference
" Commercially available authentic standards of the identified compounds were tested in dose-response studies on hamster oviducts."( Phenols, quinolines, indoles, benzene, and 2-cyclopenten-1-ones are oviductal toxicants in cigarette smoke.
Riveles, K; Roza, R; Talbot, P, 2005
)
0.33
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
Hsp70 inducerAny inducer of heat shock protein 70.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
enoneAn alpha,beta-unsaturated ketone of general formula R(1)R(2)C=CR(3)-C(=O)R(4) (R(4) =/= H) in which the C=O function is conjugated to a C=C double bond at the alpha,beta position.
alicyclic ketoneA cyclic ketone in which the carbocyclic ring structure which may be saturated or unsaturated, but may not be a benzenoid or other aromatic system.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID1432754Time-dependent Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production using urea as substrate by phenol-hypochlorite method2017Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6
Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1132956Antitumor activity against mouse Walker 256 cells allografted in Sprague-Dawley rat assessed as increase in survival rate at 2.5 mg/kg/day, ip relative to control1978Journal of medicinal chemistry, Aug, Volume: 21, Issue:8
Antitumor agents 32. Synthesis and antitumor activity of cyclopentenone derivatives related to helenalin.
AID1149566Antitumor activity against mouse EAC cells allografted in CF1 mouse assessed as survival at 33.3 mg/kg/day, ip after 7 days1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Antitumor agents. 21. A proposed mechanism for inhibition of cancer growth by tenulin and helenalin and related cyclopentenones.
AID174708Gastric cytoprotective activity in male wistar rat1997Journal of medicinal chemistry, Jun-06, Volume: 40, Issue:12
Structure-cytoprotective activity relationship of simple molecules containing an alpha,beta-unsaturated carbonyl system.
AID1432763Glutathione reactivity in pH 7.4 PBS measured after 6 to 36 hrs in presence of 1.375 mmol GSH by DTNB reagent based spectrophotometric method2017Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6
Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1149570Cytotoxicity against human Hep2 cells1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Antitumor agents. 21. A proposed mechanism for inhibition of cancer growth by tenulin and helenalin and related cyclopentenones.
AID1432756Reversible inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production by measuring recovery of enzyme activity at 10 times IC50 preincubated for 60 mins followed by 100-fold dilution in to PBS containing urea as subst2017Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6
Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1432759Inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production by measuring initial state enzyme-inhibitor complex using urea as substrate measured for 120 mins by phenol-hypochlorite method2017Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6
Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1149568Antitumor activity against rat Walker 256 cells allografted in Sprague-Dawley rat at 2.5 mg/kg/day, ip relative to control1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Antitumor agents. 21. A proposed mechanism for inhibition of cancer growth by tenulin and helenalin and related cyclopentenones.
AID1432752Cytotoxicity against mouse BALB/3T3 cells assessed as reduction in cell proliferation after 72 hrs by SRB assay2017Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6
Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1469817Thiol reactivity of the compound assessed as equilibrium constant for adduct formation2017Journal of medicinal chemistry, 02-09, Volume: 60, Issue:3
Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions.
AID1132953Antitumor activity against mouse P388 cells allografted in DBA/2 mouse assessed as increase in survival rate at 5 mg/kg/day, ip administered for 2 weeks relative to control1978Journal of medicinal chemistry, Aug, Volume: 21, Issue:8
Antitumor agents 32. Synthesis and antitumor activity of cyclopentenone derivatives related to helenalin.
AID1469819Glutathione reactivity of the compound in DMSO and phosphate buffer assessed as second order rate constant for adduct formation2017Journal of medicinal chemistry, 02-09, Volume: 60, Issue:3
Covalent Modifiers: A Chemical Perspective on the Reactivity of α,β-Unsaturated Carbonyls with Thiols via Hetero-Michael Addition Reactions.
AID1149567Antitumor activity against mouse EAC cells allografted in CF1 mouse assessed as tumor growth inhibition at 33.3 mg/kg/day, ip after 7 days1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Antitumor agents. 21. A proposed mechanism for inhibition of cancer growth by tenulin and helenalin and related cyclopentenones.
AID1149581Stability of the compound assessed as reactivity with L-cysteine by NMR analysis1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Antitumor agents. 21. A proposed mechanism for inhibition of cancer growth by tenulin and helenalin and related cyclopentenones.
AID1432760Inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production by measuring steady state enzyme-inhibitor complex using urea as substrate measured for 120 mins by phenol-hypochlorite method2017Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6
Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1132951Cytotoxicity against human Hep2 cells assessed a growth inhibition by rapid microtiter technique1978Journal of medicinal chemistry, Aug, Volume: 21, Issue:8
Antitumor agents 32. Synthesis and antitumor activity of cyclopentenone derivatives related to helenalin.
AID1149580Stability of the compound assessed as reactivity with reduced glutathione at 28 mg after 16 hrs by NMR analysis1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Antitumor agents. 21. A proposed mechanism for inhibition of cancer growth by tenulin and helenalin and related cyclopentenones.
AID1149582Stability of the compound assessed as reactivity with histidine at 28 mg after 7 days by NMR analysis1977Journal of medicinal chemistry, Mar, Volume: 20, Issue:3
Antitumor agents. 21. A proposed mechanism for inhibition of cancer growth by tenulin and helenalin and related cyclopentenones.
AID1432751Inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production using urea as substrate measured for 120 mins by phenol-hypochlorite method2017Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6
Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1432755Competitive inhibition of Sporosarcina pasteurii CCM 2056 urease assessed as reduction in ammonia production preincubated with enzyme followed by addition of varying levels of urea as substrate measured for 120 mins by Lineweaver-Burk plot analysis2017Bioorganic & medicinal chemistry letters, 03-15, Volume: 27, Issue:6
Potent covalent inhibitors of bacterial urease identified by activity-reactivity profiling.
AID1517970Inhibition of human FBPase expressed in Escherichia coli BL21 (DE3) at 500 uM using FBP as substrate incubated for 5 mins by malachite green dye based spectrophotometry relative to control2019European journal of medicinal chemistry, Dec-15, Volume: 184Discovery of novel allosteric site and covalent inhibitors of FBPase with potent hypoglycemic effects.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (318)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (0.94)18.7374
1990's10 (3.14)18.2507
2000's141 (44.34)29.6817
2010's136 (42.77)24.3611
2020's28 (8.81)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 41.22

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 strong demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index41.22 (24.57)
Research Supply Index5.79 (2.92)
Research Growth Index5.62 (4.65)
Search Engine Demand Index60.35 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (41.22)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews25 (7.65%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other302 (92.35%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]