Compounds > alpha-methylene gamma-butyrolactone
Page last updated: 2024-11-06

alpha-methylene gamma-butyrolactone

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Description

Alpha-methylene gamma-butyrolactone (AMGBL) is a natural product with a range of biological activities. It has been isolated from various sources, including plants and marine organisms. AMGBL exhibits anti-inflammatory, anti-cancer, and antimicrobial properties. Its synthesis typically involves a ring-closing metathesis reaction. Researchers study AMGBL due to its potential for developing new drugs. The compound's diverse biological activities make it a valuable target for medicinal chemistry research. AMGBL is also a useful building block for the synthesis of other bioactive compounds.'

alpha-methylene gamma-butyrolactone : A butan-4-olide having a methylene group at the 3-position. [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 CID68352
CHEMBL ID275748
CHEBI ID104120
MeSH IDM0062339

Synonyms (69)

Synonym
AKOS015840479
3-methylenedihydro-2(3h)-fuanone
2-methylenebutyrolactone
3-methylenetetrahydrofuran-2-one
securolide
lmsv-6
nsc 205367
alpha-methylene gamma-butyrolactone
alpha-methylene-gamma-butyrolactone
ai3-63021
alpha-methylene butyrolactone
einecs 208-931-6
tulipalin a
nsc-205367
2(3h)-furanone, dihydro-3-methylene-
.alpha.-methylene-.gamma.-butyrolactone
dihydro-3-methylene-2(3h)-furanone
.alpha.-methylene butyrolactone
nsc205367
547-65-9
3-methylenedihydrofuran-2(3h)-one
inchi=1/c5h6o2/c1-4-2-3-7-5(4)6/h1-3h
alpha-methylene-gamma-butyrolactone, 97%
tulipaline a
CHEMBL275748
M0907
3-methylideneoxolan-2-one
CHEBI:104120 ,
3-methylenedihydro-2(3h)-furanone
alpha-methylidene-gamma-butyrolactone
unii-362y256bol
362y256bol ,
tulipane
FT-0601116
2-methylenebutanolactone
C20578
EPITOPE ID:120381
methylene butyrolactone, alpha-
tulipalin 98
tulipalin a [inci]
.alpha.-methylene butyrolactone [mi]
a-methylene-g-butyrolactone
GEO-03235
a-methyl-y-butyrolactone
3-methylenedihydrofuran-2 (3h)-one
dihydro-3-methylene-(3h)-furanone
3-methylenedihydro-2(3h)-furanone #
W-105604
FD18014
2(3h)-furanone, dihydro-3-methylene- (
DTXSID2074663
mfcd00005407
AS-62141
BCP18620
SY013907
Q18882035
AMY7315
a-methylene-y-butyrolactone
CCG-266026
CS-W016660
4-(3-formyl-2,5-dimethyl-1h-pyrrol-1-yl)benzenecarboxylicacid
S5148
HY-N7087
3-methylenedihydrofuran-2(3h)-one (stabilized with 1% bht)
EN300-189208
-methylene butyrolactone
2(3h)-furanone, dihydro-3-methylene- (
alpha -methylene- gamma -butyrolactone
Z1255438435
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
gastrointestinal drugA drug used for its effects on the gastrointestinal system, e.g. controlling gastric acidity, regulating gastrointestinal motility and water flow, and improving digestion.
anti-ulcer drugOne of various classes of drugs with different action mechanisms used to treat or ameliorate peptic ulcer or irritation of the gastrointestinal tract.
[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 (1)

ClassDescription
butan-4-olideAny gamma-lactone having the lactone moiety derived from 4-hydroxybutanoic acid.
[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 (108)

Assay IDTitleYearJournalArticle
AID77524Compound was measured for open epicutaneous test on sensitized guinea pig after sensitization of compound (4-Hydroxy-3-methylene-1-oxa-spiro[4.5]decan-2-one)1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Allergenic alpha-methylene-gamma-butyrolactones. Study of the capacity of beta-acetoxy- and beta-hydroxy-alpha-methylene-gamma-butyrolactones to induce allergic contact dermatitis in guinea pigs.
AID1099307Insecticidal activity against adult Thrips palmi assessed as mortality at 75 ug/disk after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099280Insecticidal activity against adult Nilaparvata lugens (brown planthopper) assessed as mortality at 60 ug/disc after 48 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID403615Antimicrobial activity against Bacillus subtilis at 60 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID1099288Insecticidal activity against adult Plutella xylostella (diamondback moth) assessed as mortality at 60 ug/disc after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID403618Antimicrobial activity against Escherichia coli at 120 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID403614Antimicrobial activity against Bacillus subtilis at 120 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID170004Effect of compound (12.5 mg/kg) on Blood Ethanol level in Ethanol loaded rats after 1 hr1999Bioorganic & medicinal chemistry letters, Sep-20, Volume: 9, Issue:18
Preventive effect of sesquiterpenes from bay leaf on blood ethanol elevation in ethanol-loaded rat: structure requirement and suppression of gastric emptying.
AID1099281Insecticidal activity against adult Spodoptera litura assessed as mortality at 600 ug/disc after 48 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID76012Number of guinea pigs sensitized to alpha-methylene-gamma-butyrolactone (out of 10 guinea pigs)1980Journal of medicinal chemistry, Sep, Volume: 23, Issue:9
Synthesis of alpha-methylene-gamma-butyrolactones: a structure-activity relationship study of their allergenic power.
AID1099285Insecticidal activity against adult Plutella xylostella (diamondback moth) assessed as mortality at 600 ug/disc after 48 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099313Insecticidal activity against adult Thrips palmi assessed as mortality at 25 ug/disk after 72 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID170006Effect of compound (12.5 mg/kg) on Blood Ethanol level in Ethanol loaded rats after 30 minutes1999Bioorganic & medicinal chemistry letters, Sep-20, Volume: 9, Issue:18
Preventive effect of sesquiterpenes from bay leaf on blood ethanol elevation in ethanol-loaded rat: structure requirement and suppression of gastric emptying.
AID183545Effect of compound (50 mg/kg) on Gastric emptying in Ethanol loaded rats after 30 minutes1999Bioorganic & medicinal chemistry letters, Sep-20, Volume: 9, Issue:18
Preventive effect of sesquiterpenes from bay leaf on blood ethanol elevation in ethanol-loaded rat: structure requirement and suppression of gastric emptying.
AID403621Antimicrobial activity against Escherichia coli at 15 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID1099278Insecticidal activity against adult Nilaparvata lugens (brown planthopper) assessed as mortality at 600 ug/disc after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID170009Effect of compound (25 mg/kg) on Blood Ethanol level in Ethanol loaded rats after 30 minutes1999Bioorganic & medicinal chemistry letters, Sep-20, Volume: 9, Issue:18
Preventive effect of sesquiterpenes from bay leaf on blood ethanol elevation in ethanol-loaded rat: structure requirement and suppression of gastric emptying.
AID403625Antimicrobial activity against Pseudomonas aeruginosa at 15 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
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.
AID74912Compound was measured for open epicutaneous test on sensitized guinea pig after sensitization of compound (4-Hydroxy-3-methylene-1-oxa-spiro[4.5]decan-2-one). average skin reaction.1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Allergenic alpha-methylene-gamma-butyrolactones. Study of the capacity of beta-acetoxy- and beta-hydroxy-alpha-methylene-gamma-butyrolactones to induce allergic contact dermatitis in guinea pigs.
AID249153Lethal concentration required to kill 50% Ramos RA1 cells of the human lymphocyte with a mutation at Asp 2542004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Identification and structure-activity relationship studies of 3-methylene-2-norbornanone as potent anti-proliferative agents presumably working through p53 mediated apoptosis.
AID516578Antimicrobial activity against Escherichia coli BL21 assessed as growth inhibition at 200 uM after 24 hrs2010Bioorganic & medicinal chemistry letters, Oct-01, Volume: 20, Issue:19
Structure-activity relationships of tulipalines, tuliposides, and related compounds as inhibitors of MurA.
AID713583Cytotoxicity against human HL60/A cells after 18 hrs by annexin-V labeling-based flow cytometry2012Journal of medicinal chemistry, Oct-25, Volume: 55, Issue:20
Guaianolide sesquiterpene lactones, a source to discover agents that selectively inhibit acute myelogenous leukemia stem and progenitor cells.
AID249152Lethal concentration required to kill 50% C33A cells of the human cervical cells with a mutation at Cys 2732004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Identification and structure-activity relationship studies of 3-methylene-2-norbornanone as potent anti-proliferative agents presumably working through p53 mediated apoptosis.
AID1099308Insecticidal activity against adult Thrips palmi assessed as mortality at 50 ug/disk after 48 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID516581Electrophilicity, glutathione reactivity of the compound assessed as half life2010Bioorganic & medicinal chemistry letters, Oct-01, Volume: 20, Issue:19
Structure-activity relationships of tulipalines, tuliposides, and related compounds as inhibitors of MurA.
AID77648Compound was measured for open epicutaneous test on sensitized guinea pig after sensitization of compound itself1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Allergenic alpha-methylene-gamma-butyrolactones. Study of the capacity of beta-acetoxy- and beta-hydroxy-alpha-methylene-gamma-butyrolactones to induce allergic contact dermatitis in guinea pigs.
AID1099293Insecticidal activity against adult Frankliniella occidentalis (western flower thrips) assessed as mortality at 12.5 ug/disc after 48 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099311Insecticidal activity against adult Thrips palmi assessed as mortality at 37.5 ug/disk after 48 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099279Insecticidal activity against adult Nilaparvata lugens (brown planthopper) assessed as mortality at 60 ug/disc after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099310Insecticidal activity against adult Thrips palmi assessed as mortality at 37.5 ug/disk after 72 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099312Insecticidal activity against adult Thrips palmi assessed as mortality at 37.5 ug/disk after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID77525Compound was measured for open epicutaneous test on sensitized guinea pig after sensitization of compound (4-Hydroxy-3-methylene-dihydro-furan-2-one)1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Allergenic alpha-methylene-gamma-butyrolactones. Study of the capacity of beta-acetoxy- and beta-hydroxy-alpha-methylene-gamma-butyrolactones to induce allergic contact dermatitis in guinea pigs.
AID403903Cytotoxicity against african green monkey BSC1 cells at 60 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID403626Antimicrobial activity against Trichophyton mentagrophytes at 120 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID170010Effect of compound (50 mg/kg) on Blood Ethanol level in Ethanol loaded rats after 1 hr1999Bioorganic & medicinal chemistry letters, Sep-20, Volume: 9, Issue:18
Preventive effect of sesquiterpenes from bay leaf on blood ethanol elevation in ethanol-loaded rat: structure requirement and suppression of gastric emptying.
AID77523Compound was measured for open epicutaneous test on sensitized guinea pig after sensitization of compound (3-Methylene-1-oxa-spiro[4.5]decan-2-one)1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Allergenic alpha-methylene-gamma-butyrolactones. Study of the capacity of beta-acetoxy- and beta-hydroxy-alpha-methylene-gamma-butyrolactones to induce allergic contact dermatitis in guinea pigs.
AID403900Antimicrobial activity against Trichophyton mentagrophytes at 30 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID1099283Insecticidal activity against adult Spodoptera litura assessed as mortality at 60 ug/disc after 48 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID252828Fold selectivity expressed as ratio of LC50 for Caki cells with non-mutant p53 to LC50 for C33A cells with a mutation at Cys 2732004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Identification and structure-activity relationship studies of 3-methylene-2-norbornanone as potent anti-proliferative agents presumably working through p53 mediated apoptosis.
AID403906Cytotoxicity against mouse P388 cells1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID170008Effect of compound (25 mg/kg) on Blood Ethanol level in Ethanol loaded rats after 2 hr1999Bioorganic & medicinal chemistry letters, Sep-20, Volume: 9, Issue:18
Preventive effect of sesquiterpenes from bay leaf on blood ethanol elevation in ethanol-loaded rat: structure requirement and suppression of gastric emptying.
AID1099314Insecticidal activity against adult Thrips palmi assessed as mortality at 25 ug/disk after 48 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099296Insecticidal activity against adult Frankliniella intonsa assessed as mortality at 50 ug/disk after 72 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099305Insecticidal activity against adult Frankliniella intonsa assessed as mortality at 12.5 ug/disk after 48 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID403624Antimicrobial activity against Pseudomonas aeruginosa at 30 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID77647Compound was measured for open epicutaneous test on sensitized guinea pig after sensitization of compound (Acetic acid 4-methylene-5-oxo-tetrahydro-furan-3-yl ester)1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Allergenic alpha-methylene-gamma-butyrolactones. Study of the capacity of beta-acetoxy- and beta-hydroxy-alpha-methylene-gamma-butyrolactones to induce allergic contact dermatitis in guinea pigs.
AID516575Inhibition of Escherichia coli MurA2010Bioorganic & medicinal chemistry letters, Oct-01, Volume: 20, Issue:19
Structure-activity relationships of tulipalines, tuliposides, and related compounds as inhibitors of MurA.
AID1099292Insecticidal activity against adult Frankliniella occidentalis (western flower thrips) assessed as mortality at 12.5 ug/disc after 72 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID403901Antimicrobial activity against Trichophyton mentagrophytes at 15 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID183543Effect of compound (25 mg/kg) on Gastric emptying in Ethanol loaded rats after 30 minutes1999Bioorganic & medicinal chemistry letters, Sep-20, Volume: 9, Issue:18
Preventive effect of sesquiterpenes from bay leaf on blood ethanol elevation in ethanol-loaded rat: structure requirement and suppression of gastric emptying.
AID74905Average skin reaction in guinea pig sensitized to the sesquiterpene alantolactone1980Journal of medicinal chemistry, Sep, Volume: 23, Issue:9
Synthesis of alpha-methylene-gamma-butyrolactones: a structure-activity relationship study of their allergenic power.
AID403617Antimicrobial activity against Bacillus subtilis at 15 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID1099286Insecticidal activity against adult Plutella xylostella (diamondback moth) assessed as mortality at 600 ug/disc after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID403616Antimicrobial activity against Bacillus subtilis at 30 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID1099295Insecticidal activity against adult Frankliniella intonsa assessed as mortality at 75 ug/disk after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID77526Compound was measured for open epicutaneous test on sensitized guinea pig after sensitization of compound (Acetic acid 3-methylene-2-oxo-1-oxa-spiro[4.5]dec-4-yl ester)1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Allergenic alpha-methylene-gamma-butyrolactones. Study of the capacity of beta-acetoxy- and beta-hydroxy-alpha-methylene-gamma-butyrolactones to induce allergic contact dermatitis in guinea pigs.
AID403902Cytotoxicity against african green monkey BSC1 cells at 120 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID1099303Insecticidal activity against adult Frankliniella intonsa assessed as mortality at 25 ug/disk after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID170011Effect of compound (50 mg/kg) on Blood Ethanol level in Ethanol loaded rats after 2 hr1999Bioorganic & medicinal chemistry letters, Sep-20, Volume: 9, Issue:18
Preventive effect of sesquiterpenes from bay leaf on blood ethanol elevation in ethanol-loaded rat: structure requirement and suppression of gastric emptying.
AID1099309Insecticidal activity against adult Thrips palmi assessed as mortality at 50 ug/disk after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099277Insecticidal activity against adult Nilaparvata lugens (brown planthopper) assessed as mortality at 600 ug/disc after 48 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099306Insecticidal activity against adult Frankliniella intonsa assessed as mortality at 12.5 ug/disk after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099289Insecticidal activity against adult Frankliniella occidentalis (western flower thrips) assessed as mortality at 75 ug/disc after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099301Insecticidal activity against adult Frankliniella intonsa assessed as mortality at 25 ug/disk after 72 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID74916Compound was measured for open epicutaneous test on sensitized guinea pig after sensitization of compound itself1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Allergenic alpha-methylene-gamma-butyrolactones. Study of the capacity of beta-acetoxy- and beta-hydroxy-alpha-methylene-gamma-butyrolactones to induce allergic contact dermatitis in guinea pigs.
AID170007Effect of compound (25 mg/kg) on Blood Ethanol level in Ethanol loaded rats after 1 hr1999Bioorganic & medicinal chemistry letters, Sep-20, Volume: 9, Issue:18
Preventive effect of sesquiterpenes from bay leaf on blood ethanol elevation in ethanol-loaded rat: structure requirement and suppression of gastric emptying.
AID516577Inhibition of Escherichia coli MurA C115D mutant at 25 uM2010Bioorganic & medicinal chemistry letters, Oct-01, Volume: 20, Issue:19
Structure-activity relationships of tulipalines, tuliposides, and related compounds as inhibitors of MurA.
AID1099300Insecticidal activity against adult Frankliniella intonsa assessed as mortality at 37.5 ug/disk after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID403623Antimicrobial activity against Pseudomonas aeruginosa at 60 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID249150Lethal concentration required to kill 50% Caki-1 cells of the human renal carcinoma with non-mutant wt p532004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Identification and structure-activity relationship studies of 3-methylene-2-norbornanone as potent anti-proliferative agents presumably working through p53 mediated apoptosis.
AID1099290Insecticidal activity against adult Frankliniella occidentalis (western flower thrips) assessed as mortality at 37.5 ug/disc after 48 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID74911Compound was measured for open epicutaneous test on sensitized guinea pig after sensitization of compound (3-Methylene-1-oxa-spiro[4.5]decan-2-one) average skin reaction.1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Allergenic alpha-methylene-gamma-butyrolactones. Study of the capacity of beta-acetoxy- and beta-hydroxy-alpha-methylene-gamma-butyrolactones to induce allergic contact dermatitis in guinea pigs.
AID1099315Insecticidal activity against adult Thrips palmi assessed as mortality at 25 ug/disk after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID74914Compound was measured for open epicutaneous test on sensitized guinea pig after sensitization of compound (Acetic acid 3-methylene-2-oxo-1-oxa-spiro[4.5]dec-4-yl ester)1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Allergenic alpha-methylene-gamma-butyrolactones. Study of the capacity of beta-acetoxy- and beta-hydroxy-alpha-methylene-gamma-butyrolactones to induce allergic contact dermatitis in guinea pigs.
AID1099304Insecticidal activity against adult Frankliniella intonsa assessed as mortality at 12.5 ug/disk after 72 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099317Insecticidal activity against adult Thrips palmi assessed as mortality at 12.5 ug/disk after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID74915Compound was measured for open epicutaneous test on sensitized guinea pig after sensitization of compound (Acetic acid 4-methylene-5-oxo-tetrahydro-furan-3-yl ester) average skin reaction1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Allergenic alpha-methylene-gamma-butyrolactones. Study of the capacity of beta-acetoxy- and beta-hydroxy-alpha-methylene-gamma-butyrolactones to induce allergic contact dermatitis in guinea pigs.
AID74913Compound was measured for open epicutaneous test on sensitized guinea pig after sensitization of compound (4-Hydroxy-3-methylene-dihydro-furan-2-one) average skin reaction1986Journal of medicinal chemistry, May, Volume: 29, Issue:5
Allergenic alpha-methylene-gamma-butyrolactones. Study of the capacity of beta-acetoxy- and beta-hydroxy-alpha-methylene-gamma-butyrolactones to induce allergic contact dermatitis in guinea pigs.
AID183542Effect of compound (12.5 mg/kg) on Gastric emptying in Ethanol loaded rats after 30 minutes1999Bioorganic & medicinal chemistry letters, Sep-20, Volume: 9, Issue:18
Preventive effect of sesquiterpenes from bay leaf on blood ethanol elevation in ethanol-loaded rat: structure requirement and suppression of gastric emptying.
AID74903Average skin reaction in guinea pig sensitized to alpha-methylene-gamma-butyrolactone1980Journal of medicinal chemistry, Sep, Volume: 23, Issue:9
Synthesis of alpha-methylene-gamma-butyrolactones: a structure-activity relationship study of their allergenic power.
AID516842Antimicrobial activity against Escherichia coli BL21 assessed as growth inhibition at 200 uM in presence of minimum medium2010Bioorganic & medicinal chemistry letters, Oct-01, Volume: 20, Issue:19
Structure-activity relationships of tulipalines, tuliposides, and related compounds as inhibitors of MurA.
AID403905Cytotoxicity against african green monkey BSC1 cells at 15 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID1132950Cytotoxicity against human KB cells1978Journal of medicinal chemistry, Aug, Volume: 21, Issue:8
Potential antitumor agents. Synthesis, reactivity, and cytoxicity of alpha-methylene carbonyl compounds.
AID403622Antimicrobial activity against Pseudomonas aeruginosa at 120 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID1099299Insecticidal activity against adult Frankliniella intonsa assessed as mortality at 37.5 ug/disk after 48 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID403899Antimicrobial activity against Trichophyton mentagrophytes at 60 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID1099297Insecticidal activity against adult Frankliniella intonsa assessed as mortality at 50 ug/disk after 48 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099298Insecticidal activity against adult Frankliniella intonsa assessed as mortality at 37.5 ug/disk after 72 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099316Insecticidal activity against adult Thrips palmi assessed as mortality at 12.5 ug/disk after 72 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099282Insecticidal activity against adult Spodoptera litura assessed as mortality at 600 ug/disc after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID252829Fold selectivity expressed as ratio of LC50 for Caki cells with non-mutant p53 to LC50 for Ramos RA1 cells with a mutation at Asp 2542004Bioorganic & medicinal chemistry letters, Nov-15, Volume: 14, Issue:22
Identification and structure-activity relationship studies of 3-methylene-2-norbornanone as potent anti-proliferative agents presumably working through p53 mediated apoptosis.
AID713584Cytotoxicity against human HL60 cells after 18 hrs by annexin-V labeling-based flow cytometry2012Journal of medicinal chemistry, Oct-25, Volume: 55, Issue:20
Guaianolide sesquiterpene lactones, a source to discover agents that selectively inhibit acute myelogenous leukemia stem and progenitor cells.
AID403904Cytotoxicity against african green monkey BSC1 cells at 30 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID170005Effect of compound (12.5 mg/kg) on Blood Ethanol level in Ethanol loaded rats after 2 hr1999Bioorganic & medicinal chemistry letters, Sep-20, Volume: 9, Issue:18
Preventive effect of sesquiterpenes from bay leaf on blood ethanol elevation in ethanol-loaded rat: structure requirement and suppression of gastric emptying.
AID403619Antimicrobial activity against Escherichia coli at 60 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID1099294Insecticidal activity against adult Frankliniella occidentalis (western flower thrips) assessed as mortality at 12.5 ug/disc after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099287Insecticidal activity against adult Plutella xylostella (diamondback moth) assessed as mortality at 60 ug/disc after 48 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1144809Cytotoxicity against human 9KB cells1976Journal of medicinal chemistry, Feb, Volume: 19, Issue:2
Potential antitumor agents. Synthesis of bifunctional alpha-methylene-gamma-butyrolactones.
AID1469804Glutathione reactivity of the compound assessed as second order rate constant by 1H NMR analysis2017Journal 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.
AID403620Antimicrobial activity against Escherichia coli at 30 ug/disk1997Journal of natural products, Jun, Volume: 60, Issue:6
Antimicrobial and cytotoxic phenolic glycoside esters from the New Zealand tree Toronia toru.
AID1099291Insecticidal activity against adult Frankliniella occidentalis (western flower thrips) assessed as mortality at 37.5 ug/disc after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID516576Inhibition of Escherichia coli MurA at 25 uM2010Bioorganic & medicinal chemistry letters, Oct-01, Volume: 20, Issue:19
Structure-activity relationships of tulipalines, tuliposides, and related compounds as inhibitors of MurA.
AID76013Number guinea pigs sensitized to the sesquiterpene alantolactone (out of 7 guinea pigs)1980Journal of medicinal chemistry, Sep, Volume: 23, Issue:9
Synthesis of alpha-methylene-gamma-butyrolactones: a structure-activity relationship study of their allergenic power.
AID170012Effect of compound (50 mg/kg) on Blood Ethanol level in Ethanol loaded rats after 30 minutes1999Bioorganic & medicinal chemistry letters, Sep-20, Volume: 9, Issue:18
Preventive effect of sesquiterpenes from bay leaf on blood ethanol elevation in ethanol-loaded rat: structure requirement and suppression of gastric emptying.
AID1099302Insecticidal activity against adult Frankliniella intonsa assessed as mortality at 25 ug/disk after 48 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099284Insecticidal activity against adult Spodoptera litura assessed as mortality at 60 ug/disc after 24 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
AID1099318Insecticidal activity against adult Thrips palmi assessed as mortality at 12.5 ug/disk after 48 hr relative to control1999Bioscience, biotechnology, and biochemistry, , Volume: 63, Issue:4
Insecticidal Activity of α-Methylene-γ-butyrolactone against Several Insect Pests.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (87)

TimeframeStudies, This Drug (%)All Drugs %
pre-199012 (13.79)18.7374
1990's20 (22.99)18.2507
2000's19 (21.84)29.6817
2010's30 (34.48)24.3611
2020's6 (6.90)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews6 (6.45%)6.00%
Case Studies5 (5.38%)4.05%
Observational0 (0.00%)0.25%
Other82 (88.17%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
coumarin
2H-chromen-2-one: coumarin derivative		2.420coumarinsfluorescent dye;
human metabolite;
plant metabolite
hydroquinone
[no description available]		1.9910benzenediol;
hydroquinones		antioxidant;
carcinogenic agent;
cofactor;
Escherichia coli metabolite;
human xenobiotic metabolite;
mouse metabolite;
skin lightening agent
naphthalene
[no description available]		1.9910naphthalenes;
ortho-fused bicyclic arene		apoptosis inhibitor;
carcinogenic agent;
environmental contaminant;
mouse metabolite;
plant metabolite;
volatile oil component
thymine
[no description available]		210pyrimidine nucleobase;
pyrimidone		Escherichia coli metabolite;
human metabolite;
mouse metabolite
uracil
2,4-dihydroxypyrimidine: a urinary biomarker for bipolar disorder		210pyrimidine nucleobase;
pyrimidone		allergen;
Daphnia magna metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
prodrug;
Saccharomyces cerevisiae metabolite
iodoacetamide
[no description available]		2.1510
ethylmaleimide
Ethylmaleimide: A sulfhydryl reagent that is widely used in experimental biochemical studies.		2.1510maleimidesanticoronaviral agent;
EC 1.3.1.8 [acyl-CoA dehydrogenase (NADP(+))] inhibitor;
EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor;
EC 2.7.1.1 (hexokinase) inhibitor
pd168393
PD 168393 : A member of the class of quinazolines carrying bromoanilino and acrylamido substituents at positions 4 and 6 respectively.		2.1510acrylamides;
bromobenzenes;
quinazolines;
secondary carboxamide;
substituted aniline		epidermal growth factor receptor antagonist
bromouracil
Bromouracil: 5-Bromo-2,4(1H,3H)-pyrimidinedione. Brominated derivative of uracil that acts as an antimetabolite, substituting for thymine in DNA. It is used mainly as an experimental mutagen, but its deoxyriboside (BROMODEOXYURIDINE) is used to treat neoplasms.. 5-bromouracil : A pyrimidine having keto groups at the 2- and 4-positions and a bromo group at the 5-position. Used mainly as an experimental mutagen.		210nucleobase analogue;
pyrimidines		mutagen
pilocarpine
Pilocarpine: A slowly hydrolyzed muscarinic agonist with no nicotinic effects. Pilocarpine is used as a miotic and in the treatment of glaucoma.. (+)-pilocarpine : The (+)-enantiomer of pilocarpine.		2.0110pilocarpineantiglaucoma drug
tyrosine
Tyrosine: A non-essential amino acid. In animals it is synthesized from PHENYLALANINE. It is also the precursor of EPINEPHRINE; THYROID HORMONES; and melanin.. tyrosine : An alpha-amino acid that is phenylalanine bearing a hydroxy substituent at position 4 on the phenyl ring.		1.9810amino acid zwitterion;
erythrose 4-phosphate/phosphoenolpyruvate family amino acid;
L-alpha-amino acid;
proteinogenic amino acid;
tyrosine		EC 1.3.1.43 (arogenate dehydrogenase) inhibitor;
fundamental metabolite;
micronutrient;
nutraceutical
isoprene
isoprene: used in manufacture of ''synthetic'' rubber, butyl rubber; copolymer in production of elastomers; structure. isoprene : A hemiterpene with the formula CH2=C(CH3)CH=CH2; the monomer of natural rubber and a common structure motif to the isoprenoids, a large class of other naturally occurring compounds.		2.5420alkadiene;
hemiterpene;
volatile organic compound		plant metabolite
methacrylaldehyde
[no description available]		2.1510enal
3-buten-2-one
buten-2-one : A methyl ketone that is butan-2-one with an unsaturation at position 3.		2.1510enone;
methyl ketone
acrylamide
[no description available]		2.1510acrylamides;
N-acylammonia;
primary carboxamide		alkylating agent;
carcinogenic agent;
Maillard reaction product;
mutagen;
neurotoxin
methylmethacrylate
Methylmethacrylate: The methyl ester of methacrylic acid. It polymerizes easily to form POLYMETHYL METHACRYLATE. It is used as a bone cement.. methyl methacrylate : An enoate ester having methacrylic acid as the carboxylic acid component and methanol as the alcohol component.		2.9840enoate ester;
methyl ester		allergen;
polymerisation monomer
quinoline
[no description available]		1.9910azaarene;
mancude organic heterobicyclic parent;
ortho-fused heteroarene;
quinolines
isatin
tribulin: endogenous MONOAMINE OXIDASE inhibitory activity extractable into ethyl acetate found in brain and many mammalian tissues and fluids; ISATIN is a major component; produced in excess following alcohol withdrawal;		2.8330indoledioneEC 1.4.3.4 (monoamine oxidase) inhibitor;
plant metabolite
methyl acrylate
[no description available]		2.5220enoate ester
4-butyrolactone
4-Butyrolactone: One of the FURANS with a carbonyl thereby forming a cyclic lactone. It is an endogenous compound made from gamma-aminobutyrate and is the precursor of gamma-hydroxybutyrate. It is also used as a pharmacological agent and solvent.. tetrahydrofuranone : Any oxolane having an oxo- substituent at any position on the tetrahydrofuran ring.. gamma-butyrolactone : A butan-4-olide that is tetrahydrofuran substituted by an oxo group at position 2.		7.63770butan-4-olidemetabolite;
neurotoxin
styrene
Styrene: A colorless, toxic liquid with a strong aromatic odor. It is used to make rubbers, polymers and copolymers, and polystyrene plastics.. styrene : A vinylarene that is benzene carrying a vinyl group. It has been isolated from the benzoin resin produced by Styrax species.		2.0610styrenes;
vinylarene;
volatile organic compound		mouse metabolite;
mutagen;
plant metabolite
benzonitrile
benzonitrile : A nitrile that is hydrogen cyanide in which the hydrogen has been replaced by a phenyl group.		2.0610benzenes;
nitrile
acrolein
[no description available]		2.1510enalherbicide;
human xenobiotic metabolite;
toxin
acrylonitrile
[no description available]		1.9910aliphatic nitrile;
volatile organic compound		antifungal agent;
carcinogenic agent;
fungal metabolite;
mutagen;
polar aprotic solvent
tetrahydrofuran
oxolane : A cyclic ether that is butane in which one hydrogen from each methyl group is substituted by an oxygen.		210cyclic ether;
oxolanes;
saturated organic heteromonocyclic parent;
volatile organic compound		polar aprotic solvent
diethylene glycol
glycol ether : A hydroxyether which contains both an ether and alcohol functional groups. It is one of the most versatile classes of organic solvents which are commonly used in paints, cleaners, adhesives, pharmaceuticals and cosmetics.		2.0710hydroxyether
ethyl acrylate
[no description available]		2.4420enoate ester
n-butyl acrylate
butyl acrylate : An acrylate ester obtained by the formal condensation of the hydroxy group of butan-1-ol with the carboxy group of acrylic acid.		2.520acrylate ester
mesityl oxide
mesityl oxide: solvent for extraction of nitrocellulose, many resins, & tellurium; structure		2.1510olefinic compound
cyclopentane
Cyclopentanes: A group of alicyclic hydrocarbons with the general formula R-C5H9.. cyclopentanes : Cyclopentane and its derivatives formed by substitution.		2.420cycloalkane;
cyclopentanes;
volatile organic compound		non-polar solvent
propiolic acid
propiolic acid: RN given refers to parent cpd; structure. propynoic acid : A terminal acetylenic compound that is a 3-carbon, straight-chain, monounsaturated fatty acid having one acetylenic bond.		2.0810acetylenic fatty acid;
alpha,beta-unsaturated monocarboxylic acid;
monounsaturated fatty acid;
short-chain fatty acid;
terminal acetylenic compound		xenobiotic metabolite
norcamphor
norcamphor: RN given refers to cpd without isomeric desination		2.0210
ethyl propiolate
ethyl propiolate : The ethyl ester of prop-2-ynoic acid.		2.4420ethyl ester;
terminal acetylenic compound;
ynoate ester
cyclopentenone
2-cyclopenten-1-one : An enone that is cyclopentanone having a C=C double bond at position 2.		2.7130alicyclic ketone;
enone		Hsp70 inducer
bisphenol a-glycidyl methacrylate
Bisphenol A-Glycidyl Methacrylate: The reaction product of bisphenol A and glycidyl methacrylate that undergoes polymerization when exposed to ultraviolet light or mixed with a catalyst. It is used as a bond implant material and as the resin component of dental sealants and composite restorative materials.		1.9810diarylmethane
iridium
Iridium: A metallic element with the atomic symbol Ir, atomic number 77, and atomic weight 192.22.		2.0710cobalt group element atom;
platinum group metal atom
palladium
Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.		2.7830metal allergen;
nickel group element atom;
platinum group metal atom
rhodium
Rhodium: A hard and rare metal of the platinum group, atomic number 45, atomic weight 102.905, symbol Rh.. rhodium atom : A cobalt group element atom of atomic number 45.		2.0110cobalt group element atom
ruthenium
Ruthenium: A hard, brittle, grayish-white rare earth metal with an atomic symbol Ru, atomic number 44, and atomic weight 101.07. It is used as a catalyst and hardener for PLATINUM and PALLADIUM.		2.4620iron group element atom;
platinum group metal atom
chromium
Chromium: A trace element that plays a role in glucose metabolism. It has the atomic symbol Cr, atomic number 24, and atomic weight 52. According to the Fourth Annual Report on Carcinogens (NTP85-002,1985), chromium and some of its compounds have been listed as known carcinogens.. chromium ion : An chromium atom having a net electric charge.. chromium atom : A chromium group element atom that has atomic number 24.		2.4920chromium group element atom;
metal allergen		micronutrient
phosphine
phosphane : The simplest phosphine, consisting of a single phosphorus atom with three hydrogens attached.. phosphine : Phosphane (PH3) and compounds derived from it by substituting one, two or three hydrogen atoms by hydrocarbyl groups: RPH2, R2PH, R3P (R =/= H) are called primary, secondary and tertiary phosphines, respectively. A specific phosphine is preferably named as a substituted phosphane.		2.3110mononuclear parent hydride;
phosphanes;
phosphine		carcinogenic agent;
fumigant insecticide
pyrrolidine
[no description available]		2.0810azacycloalkane;
pyrrolidines;
saturated organic heteromonocyclic parent
alkenes
[no description available]		2.0310
3-methyl-2-butenal
3-methylbut-2-enal : An enal consisting of but-2-ene with a methyl substituent at position 3 and an oxo group at position 1.		2.1510enalmetabolite
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		2.420D-glucopyranoseepitope;
mouse metabolite
silver
[no description available]		2.0510
dehydrocostus lactone
dehydrocostus lactone : An organic heterotricyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-bis(methylene)decahydoazulen-5-yl group and in which the hydroxy group and the carboxy group have undergone formal condensation to afford the corresponding gamma-lactone.		3.1150gamma-lactone;
guaiane sesquiterpenoid;
organic heterotricyclic compound;
sesquiterpene lactone		antimycobacterial drug;
antineoplastic agent;
apoptosis inducer;
cyclooxygenase 2 inhibitor;
metabolite;
trypanocidal drug
isoalantolactone
isoalantolactone: RN given refers to (3aR-(3aalpha,4aalpha,8abeta,9aalpha))-isomer; structure. isoalantolactone : A sesquiterpene lactone of the eudesmanolide group. It has been isolated from Inula helenium.		1.9510eudesmane sesquiterpenoid;
sesquiterpene lactone		antifungal agent;
apoptosis inducer;
plant metabolite
beta-eudesmol
beta-eudesmol: found in Atractylodes and other plants; RN given refers to (2R-(2alpha,4aalpha,8abeta))-isomer. beta-eudesmol : A carbobicyclic compound that is trans-decalin substituted at positions 2, 4a, and 8 by 2-hydroxypropan-2-yl, methyl and methylidene groups, respectively (the 2R,4aR,8aS-diastereoisomer).		210carbobicyclic compound;
eudesmane sesquiterpenoid;
tertiary alcohol		volatile oil component
4-methoxydalbergione
4-methoxydalbergione: causes dermititis; RN given refers to cpd without isomeric designation		1.9610
tuliposide a
tuliposide A: RN given refers to (beta-D-Glucopyranose); RN for cpd without isomeric designation not available 2/90; found in the Alstroemeria plant		3.2560beta-D-glucoside;
homoallylic alcohol;
O-acyl carbohydrate
parthenolide
[no description available]		3.0540germacranolide
tiglic acid
tiglic acid : A 2-methylbut-2-enoic acid having its double bond in trans-configuration.. 2-methylbut-2-enoic acid : A branched-chain fatty acid consisting of 2-butenoic acid having a methyl group at position 2.		1.99102-methylbut-2-enoic acidplant metabolite
methylenolactocin
methylenolactocin: from Penicillium sp.; structure given in first source		2.4920
frullanolide
frullanolide: allergenic; structure		1.9610sesquiterpenoid
tulipalin b
tulipalin B: RN given refers to (S)-isomer; structure given in first source. tulipalin B : A member of the class of butan-4-olides that is 3-methylidenebutan-4-olide carrying an additional hydroxy substituent at position 4 (the 4R-enantiomer)		2.6830
mokko lactone
mokko lactone: isolated from mokko, Saussurea lappa; structure in first source		2.4120
santamarine
santamarine: sesquiterpene derivative of costunolide. santamarin : A sesquiterpene lactone of the eudesmanolide group.		210sesquiterpene lactone
n-phenylacrylamide
N-phenylacrylamide: structure in first source		2.1510
benzofurans
Benzofurans: Compounds that contain a BENZENE ring fused to a furan ring.		1.9610
wortmannin
[no description available]		2.1510acetate ester;
cyclic ketone;
delta-lactone;
organic heteropentacyclic compound		anticoronaviral agent;
antineoplastic agent;
autophagy inhibitor;
EC 2.7.1.137 (phosphatidylinositol 3-kinase) inhibitor;
geroprotector;
Penicillium metabolite;
radiosensitizing agent
2-oxindole
2-oxindole: RN given refers to parent cpd; structure. indolin-2-one : An indolinone carrying an oxo group at position 2.		2.4920gamma-lactam;
indolinone
2,2-bis(hydroxymethyl)-1-azabicyclo(2,2,2,)octan-3-one
2,2-bis(hydroxymethyl)-1-azabicyclo(2,2,2,)octan-3-one: structure in first source		2.0210cyclic ketone;
quinuclidines
piperitenone
piperitenone: structure given in first source		1.9910p-menthadien-3-one
arbutin
hydroquinone O-beta-D-glucopyranoside : A monosaccharide derivative that is hydroquinone attached to a beta-D-glucopyranosyl residue at position 4 via a glycosidic linkage.		1.9910beta-D-glucoside;
monosaccharide derivative		Escherichia coli metabolite;
plant metabolite
micheliolide
micheliolide: has antineoplastic activity; structure in first source		2.0710sesquiterpene lactone
parthenin
parthenin: sesqiterpene lactone from Parthenium hysterophorus; structure; RN given refers to 3aS-(3aalpha,6beta,6abeta,9abeta,9balpha)-isomer		2.0610sesquiterpene lactone
vernolepin
[no description available]		2.1510delta-lactone
lignans
Lignans: A class of dibenzylbutane derivatives which occurs in higher plants and in fluids (bile, serum, urine, etc.) in man and other animals. These compounds, which have a potential anti-cancer role, can be synthesized in vitro by human fecal flora. (From Singleton & Sainsbury, Dictionary of Microbiology and Molecular Biology, 2d ed)		2.0610
e-z cinnamic acid
cinnamic acid : A monocarboxylic acid that consists of acrylic acid bearing a phenyl substituent at the 3-position. It is found in Cinnamomum cassia.. trans-cinnamic acid : The E (trans) isomer of cinnamic acid		1.9910cinnamic acidplant metabolite
fosfomycin
Fosfomycin: An antibiotic produced by Streptomyces fradiae.. fosfomycin : A phosphonic acid having an (R,S)-1,2-epoxypropyl group attached to phosphorus.		2.0510epoxide;
phosphonic acids		antimicrobial agent;
EC 2.5.1.7 (UDP-N-acetylglucosamine 1-carboxyvinyltransferase) inhibitor
cinnamaldehyde
3-phenylprop-2-enal : A member of the class of cinnamaldehydes that is prop-2-enal in which a hydrogen at position 3 has been replaced by a phenyl group. The configuration of the double bond is not specified; the name "cinnamaldehyde" is widely used to refer to the E (trans) isomer.. (E)-cinnamaldehyde : The E (trans) stereoisomer of cinnamaldehyde, the parent of the class of cinnamaldehydes.		2.44203-phenylprop-2-enal;
cinnamaldehydes		antifungal agent;
EC 4.3.1.24 (phenylalanine ammonia-lyase) inhibitor;
flavouring agent;
hypoglycemic agent;
plant metabolite;
sensitiser;
vasodilator agent
methyl cinnamate
methyl cinnamate: RN given refers to cpd without isomeric designation. methyl cinnamate : A methyl ester resulting from the formal condensation of methyl cinnamic acid with methanol. It is found naturally in the essential oils of Alpinia and Basil leaf oil, and widely used in the flavor and perfume industries.. methyl trans-cinnamate : The E (trans) isomer of methyl cinnamate.		1.9910methyl cinnamateantibacterial agent;
fungal metabolite;
nematicide;
plant metabolite
glycosides
[no description available]		3.5180
chalcone
trans-chalcone : The trans-isomer of chalcone.		2.1510chalconeEC 3.2.1.1 (alpha-amylase) inhibitor
dibenzylidene acetone
dibenzylidene acetone: structure in first source		2.1510
sesquiterpenes
[no description available]		3.73100
curcumin
Curcumin: A yellow-orange dye obtained from tumeric, the powdered root of CURCUMA longa. It is used in the preparation of curcuma paper and the detection of boron. Curcumin appears to possess a spectrum of pharmacological properties, due primarily to its inhibitory effects on metabolic enzymes.. curcumin : A beta-diketone that is methane in which two of the hydrogens are substituted by feruloyl groups. A natural dyestuff found in the root of Curcuma longa.		2.1510aromatic ether;
beta-diketone;
diarylheptanoid;
enone;
polyphenol		anti-inflammatory agent;
antifungal agent;
antineoplastic agent;
biological pigment;
contraceptive drug;
dye;
EC 1.1.1.205 (IMP dehydrogenase) inhibitor;
EC 1.1.1.21 (aldehyde reductase) inhibitor;
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor;
EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor;
EC 1.8.1.9 (thioredoxin reductase) inhibitor;
EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor;
EC 3.5.1.98 (histone deacetylase) inhibitor;
flavouring agent;
food colouring;
geroprotector;
hepatoprotective agent;
immunomodulator;
iron chelator;
ligand;
lipoxygenase inhibitor;
metabolite;
neuroprotective agent;
nutraceutical;
radical scavenger
2,2'-bis(diphenylphosphino)-1,1'-biphenyl
2,2'-bis(diphenylphosphino)-1,1'-biphenyl: structure in first source		2.0810
fraxetin
fraxetin : A hydroxycoumarin that is 6-methoxycoumarin in which the hydrogens at positions 7 and 8 have been replaced by hydroxy groups.		1.9910aromatic ether;
hydroxycoumarin		anti-inflammatory agent;
antibacterial agent;
antimicrobial agent;
antioxidant;
apoptosis inducer;
apoptosis inhibitor;
Arabidopsis thaliana metabolite;
hepatoprotective agent;
hypoglycemic agent
7-hydroxycoumarin
7-oxycoumarin: derivatives have anti-oxidant properties. umbelliferone : A hydroxycoumarin that is coumarin substituted by a hydroxy group ay position 7.		1.9910hydroxycoumarinfluorescent probe;
food component;
plant metabolite
costunolide
[no description available]		2.4320germacranolide;
heterobicyclic compound		anthelminthic drug;
antiinfective agent;
antineoplastic agent;
antiparasitic agent;
antiviral drug;
metabolite
cerulenin
Cerulenin: An epoxydodecadienamide isolated from several species, including ACREMONIUM, Acrocylindrum, and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.. cerulenin : An epoxydodecadienamide isolated from several species, including Acremonium, Acrocylindrum and Helicoceras. It inhibits the biosynthesis of several lipids by interfering with enzyme function.		2.0510epoxide;
monocarboxylic acid amide		antifungal agent;
antiinfective agent;
antilipemic drug;
antimetabolite;
antimicrobial agent;
fatty acid synthesis inhibitor
2-octenal
2-octenal: RN given refers to cpd without isomeric designation. (E)-oct-2-enal : The (E)-isomer of oct-2-enal.. oct-2-enal : An enal consisting of oct-2-ene having an oxo group at the 1-position.		2.1510oct-2-enalantifungal agent;
volatile oil component
15-deoxy-delta(12,14)-prostaglandin j2
15-deoxy-delta(12,14)-prostaglandin J2: 15-deoxy-PGJ2 is also available; check for double bonds (indicated by delta) at 12 and 14 positions. 15-deoxy-Delta(12,14)-prostaglandin J2 : A prostaglandin J derivative comprising prostaglandin J2 lacking the 15-hydroxy group and having C=C double bonds at the 12- and 14-positions.		2.1510prostaglandins Jelectrophilic reagent;
insulin-sensitizing drug;
metabolite
andrographolide
[no description available]		2.0710carbobicyclic compound;
gamma-lactone;
labdane diterpenoid;
primary alcohol;
secondary alcohol		anti-HIV agent;
anti-inflammatory drug;
antineoplastic agent;
metabolite
palbociclib
[no description available]		2.2510aminopyridine;
aromatic ketone;
cyclopentanes;
piperidines;
pyridopyrimidine;
secondary amino compound;
tertiary amino compound		antineoplastic agent;
EC 2.7.11.22 (cyclin-dependent kinase) inhibitor
indium
Indium: A metallic element, atomic number 49, atomic weight 114.818, symbol In. It is named from its blue line in the spectrum.. indium atom : A metallic element first identified and named from the brilliant indigo (Latin indicum) blue line in its flame spectrum.		2.4820boron group element atom
2-pentenal
2-pentenal: RN given refers to cpd without isomeric designation. 2-pentenal : An enal consisting of pent-2-ene having an oxo group at the 1-position. (E)-2-pentenal : A 2-pentenal in which the double bond has (E)-configuration. It is found in cigarette smoke, virgin olive oil, and milk.		2.15102-pentenalplant metabolite
costunolide
[no description available]		2.730
arglabin
arglabin: a sesquiterpene lactone from the Chinese herb Artemisia myriantha; structure given in first source. arglabin : An organic heterotetracyclic compound and guaianolide sesquiterpene lactone that is acrylic acid which is substituted at position 2 by a 4-hydroxy-3,8-dimethyl-1,3a,4,5,6,7-hexahydroazulen-5-yl group in which the double bond in the 7-membered ring has been epoxidised and in which the hydroxy group and the carboxy group have undergone formal condensation to give the corresponding gamma-lactone. It is found in Artemisia glabella. Arglabin-DMA HCl, the hydrochloride salt of the adduct resulting from the conjugate addition of dimethylamine to the ene-lactone moiety, has been successfully used in Khazakhstan for the treatment of breast, colon, ovarian and lung cancers.		2.5120epoxide;
gamma-lactone;
organic heterotetracyclic compound;
sesquiterpene lactone		antineoplastic agent;
metabolite
9-oxo-15-hydroxy-delta 7,10,13-prostatrienoic acid methyl ester
[no description available]		2.1510
ci 940
leptomycin : A complex, very long chain, polyunsaturated fatty acid whose core structure comprises 8-oxononadeca-2,10,12,16,18-pentaenoic acid having methyl substituents at positions 3, 5, 7, 9, 11 and 15 and a 3,6-dihydropyran-6-one-2-yl group at position 19.		2.1510hydroxy polyunsaturated fatty acid;
leptomycin		antifungal agent;
bacterial metabolite
fr 148083
5Z-7-oxozeaenol : A macrolide that is the 7-oxo derivative of zeaenol (the 5Z stereoisomer). Isolated from Fungi, it exhibits cytotoxic, antibacterial and inhibitory activity against NF-kappaB.		2.1510aromatic ether;
macrolide;
phenols;
secondary alcohol;
secondary alpha-hydroxy ketone		antibacterial agent;
antineoplastic agent;
metabolite;
NF-kappaB inhibitor
4-methylene-2-octyl-5-oxofuran-3-carboxylic acid
4-methylene-2-octyl-5-oxofuran-3-carboxylic acid: an anorectic fatty acid synthase inhibitor; structure in first source. (2R,3S)-C75 : A 4-methylidene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid that has 2R,3S-configuration.		2104-methylidene-2-octyl-5-oxotetrahydrofuran-3-carboxylic acid;
gamma-lactone
cp 31398
CP 31398: structure in first source		2.0210
pyrrocidine a
pyrrocidine A: an antifungal antibiotic isolated from Acremonium zeae; structure in first souce		2.1510
hydroxymatairesinol
hydroxymatairesinol: a plant lignan from Norway spruce (Picea abies); structure in first source		2.0610
cytochrome c-t
Cytochromes c: Cytochromes of the c type that are found in eukaryotic MITOCHONDRIA. They serve as redox intermediates that accept electrons from MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX III and transfer them to MITOCHONDRIAL ELECTRON TRANSPORT COMPLEX IV.		2.0410
6-tuliposide a
6-tuliposide A: from Alstroemeria ligtu L.; structure given in first source; RN given from Chem Abstr. Index Guide 1985; RN not Chemline 9/85. 6-tuliposide A : A 6-O-acyl-D-glucose that is the 6-O-(4-hydroxy-2-methylenebutanoyl) derivative of D-glucopyranose.		2.75306-O-acyl-D-glucose;
homoallylic alcohol		allergen;
metabolite
sodium oxybate
Sodium Oxybate: The sodium salt of 4-hydroxybutyric acid. It is used for both induction and maintenance of ANESTHESIA.		3.5180
piperidines
Piperidines: A family of hexahydropyridines.		2.2510
warfarin
Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.		1.9910benzenes;
hydroxycoumarin;
methyl ketone
4-hydroxycoumarin
2-hydroxychromone: structure		1.9910hydroxycoumarin
rociletinib
rociletinib: inhibits epidermal growth factor receptor tyrosine kinase activity; structure in first source		2.1510
osimertinib
osimertinib: an EGFR tyrosine kinase inhibitor. osimertinib : A member of the class of aminopyrimidines that is 4-(1-methylindol-3-yl)pyrimidin-2-amine in which one of the amino hydrogens is replaced by a 2-methoxy-4-[2-(dimethylamino)ethyl](methyl)amino-5-acrylamidophenyl group. Used (as the mesylate salt) for treatment of EGFR T790M mutation positive non-small cell lung cancer.		2.1510acrylamides;
aminopyrimidine;
biaryl;
indoles;
monomethoxybenzene;
secondary amino compound;
secondary carboxamide;
substituted aniline;
tertiary amino compound		antineoplastic agent;
epidermal growth factor receptor antagonist
ConditionIndicatedRelationship StrengthStudiesTrials
Carcinoma 256, Walker
A transplantable carcinoma of the rat that originally appeared spontaneously in the mammary gland of a pregnant albino rat, and which now resembles a carcinoma in young transplants and a sarcoma in older transplants. (Stedman, 25th ed)		01.9510
Leukemia L 1210
[description not available]		01.9510
Contact Dermatitis
[description not available]		04.13160
Dermatitis, Contact
A type of acute or chronic skin reaction in which sensitivity is manifested by reactivity to materials or substances coming in contact with the skin. It may involve allergic or non-allergic mechanisms.		04.13160
Gastric Ulcer
[description not available]		02.420
Stomach Ulcer
Ulceration of the GASTRIC MUCOSA due to contact with GASTRIC JUICE. It is often associated with HELICOBACTER PYLORI infection or consumption of nonsteroidal anti-inflammatory drugs (NSAIDS).		02.420
Acute Myelogenous Leukemia
[description not available]		02.0710
Leukemia, Myeloid, Acute
Clonal expansion of myeloid blasts in bone marrow, blood, and other tissue. Myeloid leukemias develop from changes in cells that normally produce NEUTROPHILS; BASOPHILS; EOSINOPHILS; and MONOCYTES.		02.0710
Dermatitis, Eczematous
[description not available]		03.3340
Eczema
A pruritic papulovesicular dermatitis occurring as a reaction to many endogenous and exogenous agents (Dorland, 27th ed).		03.3340
Colorectal Cancer
[description not available]		02.2510
Colorectal Neoplasms
Tumors or cancer of the COLON or the RECTUM or both. Risk factors for colorectal cancer include chronic ULCERATIVE COLITIS; FAMILIAL POLYPOSIS COLI; exposure to ASBESTOS; and irradiation of the CERVIX UTERI.		02.2510
Cancer of Ovary
[description not available]		02.2510
Ovarian Neoplasms
Tumors or cancer of the OVARY. These neoplasms can be benign or malignant. They are classified according to the tissue of origin, such as the surface EPITHELIUM, the stromal endocrine cells, and the totipotent GERM CELLS.		02.2510
Dermatitis, Occupational
A recurrent contact dermatitis caused by substances found in the work place.		04.1660
Hand Dermatosis
[description not available]		04.61100
Hand Dermatoses
Skin diseases involving the HANDS.		04.61100
Cancer of Pancreas
[description not available]		02.0810
Pancreatic Neoplasms
Tumors or cancer of the PANCREAS. Depending on the types of ISLET CELLS present in the tumors, various hormones can be secreted: GLUCAGON from PANCREATIC ALPHA CELLS; INSULIN from PANCREATIC BETA CELLS; and SOMATOSTATIN from the SOMATOSTATIN-SECRETING CELLS. Most are malignant except the insulin-producing tumors (INSULINOMA).		02.0810
Allergic Contact Dermatitis
[description not available]		04.3170
Dermatitis, Allergic Contact
A contact dermatitis due to allergic sensitization to various substances. These substances subsequently produce inflammatory reactions in the skin of those who have acquired hypersensitivity to them as a result of prior exposure.		04.3170
Carcinoma, Ehrlich Tumor
A transplantable, poorly differentiated malignant tumor which appeared originally as a spontaneous breast carcinoma in a mouse. It grows in both solid and ascitic forms.		02.0610
Cancer of Colon
[description not available]		02.0610
Cancer of Prostate
[description not available]		02.0610
Colonic Neoplasms
Tumors or cancer of the COLON.		02.0610
Prostatic Neoplasms
Tumors or cancer of the PROSTATE.		02.0610
Invasiveness, Neoplasm
[description not available]		02.0210
Dermatitis, Irritant
A non-allergic contact dermatitis caused by prolonged exposure to irritants and not explained by delayed hypersensitivity mechanisms.		02.9110
Agricultural Worker Disease
[description not available]		01.9910
Diseases, Occupational
[description not available]		0210
Experimental Neoplasms
[description not available]		01.9710