Page last updated: 2024-12-07

3-acetyllupeol

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

Description

3-Acetyllupeol is a triterpene compound isolated from various plant sources, including lupeol, a naturally occurring pentacyclic triterpene found in many plants. 3-Acetyllupeol exhibits a range of biological activities, including antioxidant, anti-inflammatory, anticancer, and antimicrobial properties. Its synthesis involves the acetylation of lupeol, typically using acetic anhydride and a catalyst. Research on 3-acetyllupeol is driven by its potential therapeutic applications in various diseases. The compound is investigated for its effects on cell proliferation, apoptosis, and inflammation, as well as its ability to modulate signaling pathways involved in disease development. Furthermore, its antioxidant properties are being studied for their potential to protect against oxidative stress-related diseases. 3-acetyllupeol is gaining attention as a promising lead compound for the development of new therapeutic agents.'
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3-acetyllupeol: from root of Euphorbia fischeriana Steud; RN refers to (3beta)-isomer [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
EuphorbiagenusA large plant genus of the family EUPHORBIACEAE, order Euphorbiales, subclass Rosidae. They have a milky sap and a female flower consisting of a single pistil surrounded by numerous male flowers of one stamen each. Euphorbia hirta is rarely called milkweed but that name is normally used for ASCLEPIAS.[MeSH]EuphorbiaceaeThe spurge family of flowering plants in the order Malpighiales. The family consists of annual and perennial herbs and woody shrubs or trees. Members contain securinine.[MeSH]
Euphorbia fischerianaspecies[no description available]EuphorbiaceaeThe spurge family of flowering plants in the order Malpighiales. The family consists of annual and perennial herbs and woody shrubs or trees. Members contain securinine.[MeSH]

Cross-References

ID SourceID
PubMed CID92157
CHEMBL ID453802
CHEBI ID69744
SCHEMBL ID936136
MeSH IDM0155828

Synonyms (33)

Synonym
[(1r,3ar,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-yl] acetate
acetic acid (1r,3ar,4s,5ar,5br,7ar,9s,11ar,11br,13ar,13br)-1-isopropenyl-3a,5a,5b,8,8,11a-hexamethyl-eicosahydro-cyclopenta[a]chrysen-9-yl ester
lup-20(29)-en-3-ol, acetate, (3.beta.)-
lupeyl acetate
nsc-281806
lupenyl acetate
3-o-acetyllupeol
lup-20(29)-en-3.beta.-ol, acetate
lupeol acetate
C08630
1617-68-1
3-acetyllupeol
LMPR0106130002
CHEMBL453802
chebi:69744 ,
lup-20(29)-en-3beta-ol, acetate
lup-20(29)-en-3-ol, acetate, (3beta)-
einecs 216-575-8
nsc 281806
wj3a89g0h6 ,
unii-wj3a89g0h6
lup-20(29)-en-3.beta.-yl acetate
lup-20(30)-en-3.beta.-ol, acetate
clerodol acetate
3.beta.-oac-20(29)-lupene
lupeol acetate [mi]
SCHEMBL936136
mfcd00017362
Q27104976
HY-126114
CS-0090571
MS-28664
AKOS040760532
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[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
organic molecular entityAny molecular entity that contains carbon.
[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 (35)

Assay IDTitleYearJournalArticle
AID327685Cytotoxicity against human NCI-H187 cells at 10 ug/mL2008Journal of natural products, Feb, Volume: 71, Issue:2
Seco-terpenoids and other constituents from Elateriospermum tapos.
AID338356Cytotoxicity against human Raji cells assessed as cell viability at 1000 mol ratio after 48 hrs relative to TPA
AID338355Cytotoxicity against human Raji cells assessed as cell viability at 5000 mol ratio after 48 hrs relative to TPA
AID334049Inhibition of larval development in zebra fish at 10 ug/mL1997Journal of natural products, Dec, Volume: 60, Issue:12
Mueggelone, a novel inhibitor of fish development from the fresh water cyanobacterium Aphanizomenon flos-aquae.
AID335874Cytotoxicity against human A2780 cells2002Journal of natural products, Aug, Volume: 65, Issue:8
Two new triterpene esters from the twigs of Brachylaena ramiflora from the Madagascar rainforest.
AID334273Induction of melanogenesis in mouse B16 2F2 cells assessed as intracellular melanin content after 3 days2002Journal of natural products, May, Volume: 65, Issue:5
Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line.
AID1332165Cytotoxicity against human Hep3B cells assessed as cell growth inhibition by MTT assay
AID334272Growth inhibition of mouse B16 2F2 cells after 3 days2002Journal of natural products, May, Volume: 65, Issue:5
Differentiation- and apoptosis-inducing activities by pentacyclic triterpenes on a mouse melanoma cell line.
AID489306Antituberculosis activity against Mycobacterium tuberculosis H37Rv ATCC 27294 in stationary phase culture at pH 5.8 up to 200 ug/ml after 3 days followed by washout from day 4 to week 4 by microbroth dilution method2010Bioorganic & medicinal chemistry letters, Jul-15, Volume: 20, Issue:14
In vitro antituberculosis activities of the constituents isolated from Haloxylon salicornicum.
AID489305Antituberculosis activity against Mycobacterium tuberculosis H37Rv ATCC 27294 after 2 weeks by microbroth dilution method2010Bioorganic & medicinal chemistry letters, Jul-15, Volume: 20, Issue:14
In vitro antituberculosis activities of the constituents isolated from Haloxylon salicornicum.
AID338352Inhibition of TPA-induced EBV-early antigen activation in human Raji cells assessed as early antigen activation at 100 mol ratio after 48 hrs relative to TPA
AID1179490Cytotoxicity against mouse RAW264.7 cells assessed as cell viability at IC50 by MTT assay relative to control2014Bioorganic & medicinal chemistry letters, Aug-01, Volume: 24, Issue:15
Synthesis of new heterocyclic lupeol derivatives as nitric oxide and pro-inflammatory cytokine inhibitors.
AID334038Inhibition of larval development in zebra fish assessed as induction of edema in heart at 100 ug/mL after 5 days1997Journal of natural products, Dec, Volume: 60, Issue:12
Mueggelone, a novel inhibitor of fish development from the fresh water cyanobacterium Aphanizomenon flos-aquae.
AID1332166Cytotoxicity against human A549 cells assessed as cell growth inhibition by MTT assay
AID1179488Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced NO production incubated for 1 hr prior to LPS challenge measured after 24 hrs by Griess method2014Bioorganic & medicinal chemistry letters, Aug-01, Volume: 24, Issue:15
Synthesis of new heterocyclic lupeol derivatives as nitric oxide and pro-inflammatory cytokine inhibitors.
AID334050Inhibition of larval development in zebra fish assessed as effect on larval mortality at 10 ug/mL1997Journal of natural products, Dec, Volume: 60, Issue:12
Mueggelone, a novel inhibitor of fish development from the fresh water cyanobacterium Aphanizomenon flos-aquae.
AID334048Inhibition of larval development in zebra fish assessed as tail bending at 100 ug/mL after 5 days1997Journal of natural products, Dec, Volume: 60, Issue:12
Mueggelone, a novel inhibitor of fish development from the fresh water cyanobacterium Aphanizomenon flos-aquae.
AID338354Inhibition of EBV-early antigen activation in human Raji cells assessed as early antigen activation at 1 uM ratio after 48 hrs
AID327686Cytotoxicity against human breast cancer cells at 10 ug/mL2008Journal of natural products, Feb, Volume: 71, Issue:2
Seco-terpenoids and other constituents from Elateriospermum tapos.
AID477821Antiinflammatory activity against mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide release after 24 hrs2010Journal of natural products, Apr-23, Volume: 73, Issue:4
Terpenoids from Daphne aurantiaca and their potential anti-inflammatory activity.
AID1179489Antiinflammatory activity in mouse J774A1 cells assessed as inhibition of LPS-induced NO production incubated for 1 hr prior to LPS challenge measured after 24 hrs by Griess method2014Bioorganic & medicinal chemistry letters, Aug-01, Volume: 24, Issue:15
Synthesis of new heterocyclic lupeol derivatives as nitric oxide and pro-inflammatory cytokine inhibitors.
AID337068Cytotoxicity against human A2780 cells2003Journal of natural products, Mar, Volume: 66, Issue:3
New cytotoxic lupane triterpenoids from the twigs of Coussarea paniculata.
AID402278Cytotoxicity against human A2780 cells2004Journal of natural products, May, Volume: 67, Issue:5
New cytotoxic terpenoids from the wood of Vepris punctata from the Madagascar Rainforest.
AID338357Cytotoxicity against human Raji cells assessed as cell viability at 100 mol ratio after 48 hrs relative to TPA
AID334051Inhibition of larval development in zebra fish assessed as effect on larval mortality at 100 ug/mL1997Journal of natural products, Dec, Volume: 60, Issue:12
Mueggelone, a novel inhibitor of fish development from the fresh water cyanobacterium Aphanizomenon flos-aquae.
AID667668Inhibition of X4-tropic HIV1 envelope glycoprotein-mediated cell-cell fusion between viral envelope expressing human virus-infected HeLa ADA cells to human HeLa P5 cells at 5 uM after 16 hrs by beta-galactosidase reporter gene assay using chemiluminescenc2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Synthesis and anti-HIV activity of lupane and olean-18-ene derivatives. Absolute configuration of 19,20-epoxylupanes by VCD.
AID1297379Antitrichomonal activity against metronidazole-sensitive Trichomonas vaginalis ATCC 30236 clinical isolate trophozoites assessed as parasite viability at 100 uM after 24 hrs by trypan blue dye based hemocytometry2016Bioorganic & medicinal chemistry letters, May-01, Volume: 26, Issue:9
Caatinga plants: Natural and semi-synthetic compounds potentially active against Trichomonas vaginalis.
AID334046Inhibition of larval development in zebra fish assessed as induction of edema in heart at 100 ug/mL after 3 days1997Journal of natural products, Dec, Volume: 60, Issue:12
Mueggelone, a novel inhibitor of fish development from the fresh water cyanobacterium Aphanizomenon flos-aquae.
AID334047Inhibition of larval development in zebra fish assessed as tail bending at 100 ug/mL after 3 days1997Journal of natural products, Dec, Volume: 60, Issue:12
Mueggelone, a novel inhibitor of fish development from the fresh water cyanobacterium Aphanizomenon flos-aquae.
AID667667Inhibition of R5-tropic HIV1 envelope glycoprotein-mediated cell-cell fusion between viral envelope expressing human virus-infected HeLa ADA cells to human HeLa P5 cells at 5 uM after 16 hrs by beta-galactosidase reporter gene assay using chemiluminescenc2012Journal of natural products, Apr-27, Volume: 75, Issue:4
Synthesis and anti-HIV activity of lupane and olean-18-ene derivatives. Absolute configuration of 19,20-epoxylupanes by VCD.
AID338351Inhibition of TPA-induced EBV-early antigen activation in human Raji cells assessed as early antigen activation at 1000 mol ratio after 48 hrs relative to TPA
AID338358Cytotoxicity against human Raji cells assessed as cell viability at 10 mol ratio after 48 hrs relative to TPA
AID1179491Cytotoxicity against mouse J774A1 cells assessed as cell viability at IC50 by MTT assay relative to control2014Bioorganic & medicinal chemistry letters, Aug-01, Volume: 24, Issue:15
Synthesis of new heterocyclic lupeol derivatives as nitric oxide and pro-inflammatory cytokine inhibitors.
AID338350Inhibition of TPA-induced EBV-early antigen activation in human Raji cells assessed as early antigen activation at 5000 mol ratio after 48 hrs relative to TPA
AID338353Inhibition of TPA-induced EBV-early antigen activation in human Raji cells assessed as early antigen activation at 10 mol ratio after 48 hrs relative to TPA
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19901 (7.69)18.7374
1990's1 (7.69)18.2507
2000's5 (38.46)29.6817
2010's6 (46.15)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: 12.43

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 Index12.43 (24.57)
Research Supply Index2.71 (2.92)
Research Growth Index5.14 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.43)

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%
Other14 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]