Page last updated: 2024-12-11

3 beta-o-acetylursolic acid

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

Cross-References

ID SourceID
PubMed CID6475119
CHEMBL ID410525
CHEBI ID175831
SCHEMBL ID10951133
MeSH IDM0467616

Synonyms (21)

Synonym
(1s,2r,4as,6ar,6as,6br,8ar,10s,12ar,14bs)-10-acetyloxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid
CHEBI:175831
(1s,2r,4as,6ar,6as,6br,8ar,10s,12ar,14bs)-10-acetoxy-1,2,6a,6b,9,9,12a-heptamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydro-1h-picene-4a-carboxylic acid
ursolic acid acetate
MLS000728570
smr000445682
3-acetylursolic acid
3beta-o-acetylursolic acid
o-acetylursolic acid
CHEMBL410525 ,
NCGC00247636-01
bdbm50346610
AKOS016036256
SCHEMBL10951133
3-o-acetylursolic acid
mfcd09752431
3-(acetyloxy)urs-12-en-28-oic acid
DTXSID40994595
CS-0023373
HY-N2815
A1-34641
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
triterpenoidAny terpenoid derived from a triterpene. The term includes compounds in which the C30 skeleton of the parent triterpene has been rearranged or modified by the removal of one or more skeletal atoms (generally methyl groups).
[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]

Protein Targets (8)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, MAJOR APURINIC/APYRIMIDINIC ENDONUCLEASEHomo sapiens (human)Potency19.95260.003245.467312,589.2998AID2517
Chain A, ATP-DEPENDENT DNA HELICASE Q1Homo sapiens (human)Potency0.56230.125919.1169125.8920AID2549
nonstructural protein 1Influenza A virus (A/WSN/1933(H1N1))Potency3.98110.28189.721235.4813AID2326
DNA polymerase betaHomo sapiens (human)Potency39.81070.022421.010289.1251AID485314
nuclear receptor ROR-gamma isoform 1Mus musculus (house mouse)Potency0.35480.00798.23321,122.0200AID2551
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glycogen phosphorylase, muscle formOryctolagus cuniculus (rabbit)IC50 (µMol)131.41300.01405.93249.0000AID603224
Tyrosyl-DNA phosphodiesterase 1Homo sapiens (human)IC50 (µMol)100.00000.01203.32138.4300AID1662670
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
streptokinase A precursorStreptococcus pyogenes M1 GASEC50 (µMol)2.82800.06008.9128130.5170AID1902
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (3)

Processvia Protein(s)Taxonomy
single strand break repairTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
DNA repairTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
double-strand break repairTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
double-stranded DNA bindingTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
single-stranded DNA bindingTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
exonuclease activityTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
protein bindingTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
3'-tyrosyl-DNA phosphodiesterase activityTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
nucleoplasmTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
cytoplasmTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
plasma membraneTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
intracellular membrane-bounded organelleTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
nucleusTyrosyl-DNA phosphodiesterase 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (36)

Assay IDTitleYearJournalArticle
AID691857Cytotoxicity against human HT-29 cells incubated for 48 hrs by MTT assay2011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Synthesis of [3β-acetoxy-urs-12-en-28-oyl]-1-monoglyceride and investigation on its anti tumor effects against BGC-823.
AID346797Antiproliferative activity against human HeLa cells at 10 uM after 96 hrs by MTT assay2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
The synthesis of ursolic acid derivatives with cytotoxic activity and the investigation of their preliminary mechanism of action.
AID333388Antitrypanosomal activity against Trypanosoma brucei S427 by microdilution method2004Journal of natural products, Oct, Volume: 67, Issue:10
Triterpenoids from Brazilian Ilex species and their in vitro antitrypanosomal activity.
AID1662672Cytotoxicity against human A549 cells assessed as growth inhibition after 72 hrs by MTT assay2020Bioorganic & medicinal chemistry, 06-01, Volume: 28, Issue:11
Secondary metabolites from Isodon ternifolius (D. Don) Kudo and their anticancer activity as DNA topoisomerase IB and Tyrosyl-DNA phosphodiesterase 1 inhibitors.
AID452564Cytotoxicity against human NTUB1 cells after 72 hrs by MTT assay2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Ursolic acid derivatives induce cell cycle arrest and apoptosis in NTUB1 cells associated with reactive oxygen species.
AID346957Antiproliferative activity against human BGC823 cells after 96 hrs by MTT assay2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
The synthesis of ursolic acid derivatives with cytotoxic activity and the investigation of their preliminary mechanism of action.
AID364070Inhibition of aromatase2008European journal of medicinal chemistry, Sep, Volume: 43, Issue:9
Evaluation of ursolic acid isolated from Ilex paraguariensis and derivatives on aromatase inhibition.
AID689291Cytotoxicity against human AsPC1 cells after 72 hrs by MTT assay2012Bioorganic & medicinal chemistry, Oct-01, Volume: 20, Issue:19
Synthesis of novel ursolic acid heterocyclic derivatives with improved abilities of antiproliferation and induction of p53, p21waf1 and NOXA in pancreatic cancer cells.
AID691860Cytotoxicity against human GES-1 cells incubated for 48 hrs by MTT assay2011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Synthesis of [3β-acetoxy-urs-12-en-28-oyl]-1-monoglyceride and investigation on its anti tumor effects against BGC-823.
AID691859Cytotoxicity against human BGC823 cells by MTT assay2011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Synthesis of [3β-acetoxy-urs-12-en-28-oyl]-1-monoglyceride and investigation on its anti tumor effects against BGC-823.
AID333387Antitrypanosomal activity against Trypanosoma cruzi Tulahuen CL2 by microdilution method2004Journal of natural products, Oct, Volume: 67, Issue:10
Triterpenoids from Brazilian Ilex species and their in vitro antitrypanosomal activity.
AID1662671Cytotoxicity against human MCF7 cells assessed as reduction in cell viability after 72 hrs by MTT assay2020Bioorganic & medicinal chemistry, 06-01, Volume: 28, Issue:11
Secondary metabolites from Isodon ternifolius (D. Don) Kudo and their anticancer activity as DNA topoisomerase IB and Tyrosyl-DNA phosphodiesterase 1 inhibitors.
AID1153780Inhibition of TPH-1-mediated serotonin biosynthesis in rat RBL2H3 cells at 10 uM after 48 hrs by RP-HPLC analysis relative to control2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Tryptophan hydroxylase 1 (Tph-1)-targeted bone anabolic agents for osteoporosis.
AID1153782Cytotoxicity against rat RBL2H3 cells by MTT assay2014Journal of medicinal chemistry, Jun-12, Volume: 57, Issue:11
Tryptophan hydroxylase 1 (Tph-1)-targeted bone anabolic agents for osteoporosis.
AID1888106Cytotoxicity against human HeLa cells assessed as inhibition of cell growth incubated for 72 hrs by CCK-8 assay2022European journal of medicinal chemistry, Jan-05, Volume: 227Discovery and radiosensitization research of ursolic acid derivatives as SENP1 inhibitors.
AID1370899Selectivity index, ratio of CC50 for human HepG2 cells to IC50 for chloroquine-resistant Plasmodium falciparum W2
AID320719Inhibition of beta-hematin formation at 1 to 20 mM2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Pharmacomodulation on the 3-acetylursolic acid skeleton: Design, synthesis, and biological evaluation of novel N-{3-[4-(3-aminopropyl)piperazinyl]propyl}-3-O-acetylursolamide derivatives as antimalarial agents.
AID691858Cytotoxicity against human HepG2 cells incubated for 48 hrs by MTT assay2011Bioorganic & medicinal chemistry, Jul-01, Volume: 19, Issue:13
Synthesis of [3β-acetoxy-urs-12-en-28-oyl]-1-monoglyceride and investigation on its anti tumor effects against BGC-823.
AID1888104Inhibition of recombinant human SENP1 catalytic domain at 2 uM using RanGAP1 as substrate preincubated for 10 mins followed by substrate addition and measured after 30 mins by Western blot analysis relative to control2022European journal of medicinal chemistry, Jan-05, Volume: 227Discovery and radiosensitization research of ursolic acid derivatives as SENP1 inhibitors.
AID1662670Inhibition of TDP1 (unknown origin) expressed in Escherichia coli BL21 (DE3) using 5'-FAM-AGGATCTAAAAGACTT-BHQ-3' as substrate preincubated for 30 mins followed by substrate addition by fluorescence assay2020Bioorganic & medicinal chemistry, 06-01, Volume: 28, Issue:11
Secondary metabolites from Isodon ternifolius (D. Don) Kudo and their anticancer activity as DNA topoisomerase IB and Tyrosyl-DNA phosphodiesterase 1 inhibitors.
AID1662669Inhibition of calf thymus Top1 assessed as reduction in supercoiled pBR322 DNA relaxation at 100 uM measured after 30 mins by agarose gel electrophoresis relative to camptothecin2020Bioorganic & medicinal chemistry, 06-01, Volume: 28, Issue:11
Secondary metabolites from Isodon ternifolius (D. Don) Kudo and their anticancer activity as DNA topoisomerase IB and Tyrosyl-DNA phosphodiesterase 1 inhibitors.
AID1370897Cytotoxicity against African green monkey Vero cells after 72 hrs by MTT assay
AID346800Antiproliferative activity against human HeLa cells after 96 hrs by MTT assay2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
The synthesis of ursolic acid derivatives with cytotoxic activity and the investigation of their preliminary mechanism of action.
AID1604321Antiparasitic activity against Toxoplasma gondii2019European journal of medicinal chemistry, Dec-01, Volume: 183Recent progress on anti-Toxoplasma drugs discovery: Design, synthesis and screening.
AID320712Antimalarial activity against chloroquine-resistant Plasmodium falciparum FcB1 after 24 hrs2008Bioorganic & medicinal chemistry, Jan-15, Volume: 16, Issue:2
Pharmacomodulation on the 3-acetylursolic acid skeleton: Design, synthesis, and biological evaluation of novel N-{3-[4-(3-aminopropyl)piperazinyl]propyl}-3-O-acetylursolamide derivatives as antimalarial agents.
AID603224Inhibition of rabbit muscle glycogen phosphorylase A assessed as release of phosphate from glucose-1-phosphate after 25 mins by microplate reader based method2011European journal of medicinal chemistry, Jun, Volume: 46, Issue:6
Identification of pentacyclic triterpenes derivatives as potent inhibitors against glycogen phosphorylase based on 3D-QSAR studies.
AID1662673Cytotoxicity against human HCT116 cells assessed as growth inhibition after 72 hrs by MTT assay2020Bioorganic & medicinal chemistry, 06-01, Volume: 28, Issue:11
Secondary metabolites from Isodon ternifolius (D. Don) Kudo and their anticancer activity as DNA topoisomerase IB and Tyrosyl-DNA phosphodiesterase 1 inhibitors.
AID346799Antiproliferative activity against human BGC823 cells at 10 uM after 96 hrs by MTT assay2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
The synthesis of ursolic acid derivatives with cytotoxic activity and the investigation of their preliminary mechanism of action.
AID1370896Antiplasmodial activity against chloroquine-resistant Plasmodium falciparum W2 infected in human erythrocytes
AID1662676Inhibition of TDP1 (unknown origin) expressed in Escherichia coli BL21 (DE3) at 100 uM using 5'-FAM-AGGATCTAAAAGACTT-BHQ-3' as substrate preincubated for 30 mins followed by substrate addition by fluorescence assay relative to control2020Bioorganic & medicinal chemistry, 06-01, Volume: 28, Issue:11
Secondary metabolites from Isodon ternifolius (D. Don) Kudo and their anticancer activity as DNA topoisomerase IB and Tyrosyl-DNA phosphodiesterase 1 inhibitors.
AID1370898Cytotoxicity against human HepG2 cells after 72 hrs by MTT assay
AID346801Antiproliferative activity against human SKOV3 cells after 96 hrs by MTT assay2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
The synthesis of ursolic acid derivatives with cytotoxic activity and the investigation of their preliminary mechanism of action.
AID346798Antiproliferative activity against human SKOV3 cells at 10 uM after 96 hrs by MTT assay2009Bioorganic & medicinal chemistry, Jan-15, Volume: 17, Issue:2
The synthesis of ursolic acid derivatives with cytotoxic activity and the investigation of their preliminary mechanism of action.
AID1295390Antiplasmodial activity against Plasmodium falciparum Dd2 incubated under low oxygen conditions after 72 hrs by SYBR green assay2016Bioorganic & medicinal chemistry, 06-01, Volume: 24, Issue:11
Antiplasmodial phloroglucinol derivatives from Syncarpia glomulifera.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (15)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's5 (33.33)29.6817
2010's8 (53.33)24.3611
2020's2 (13.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.82

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 Index11.82 (24.57)
Research Supply Index2.77 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.82)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (6.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other14 (93.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]