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oleanonic acid

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Description

oleanonic acid: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID12313704
CHEMBL ID470029
SCHEMBL ID246220
MeSH IDM0419169

Synonyms (26)

Synonym
oleanonic acid
3-oxoolean-12-en-28-oic acid
CHEMBL470029 ,
17990-42-0
olean-12-en-28-oic acid, 3-oxo-
bdbm50346613
S9505 ,
SCHEMBL246220
3-oxo-olean-12-en28-saure
AC-33969
Q-100212
HY-N1487
oleanonic?acid
3-oxooleanolic acid
3-ketooleanolic acid
3-oxooleanolicacid
(4as,6ar,6as,6br,8ar,12ar,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1h-picene-4a-carboxylicacid
CS-5795
AKOS032948921
F16163
mfcd09752411
DTXSID90939279
(4as,6ar,6as,6br,8ar,12ar,14bs)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1h-picene-4a-carboxylic acid
AS-76428
oleoside 11-methylester
oleanonicacid

Research Excerpts

Effects

ExcerptReferenceRelevance
"Oleanonic acid has been isolated from the acetone extracts of the roots and rhizomes of Patrinia scabiosaefolia Fish. "( [Isolation and identification of oleanonic acid from Patrinia scabiosaefolia].
Chen, Y; Jin, M; Tong, L; Yang, B, 1999
)
2.03
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Glycogen phosphorylase, muscle formOryctolagus cuniculus (rabbit)IC50 (µMol)17.89570.01405.93249.0000AID266475; AID404873; AID603224
Tissue factorHomo sapiens (human)IC50 (µMol)0.00020.00010.734410.0000AID1436859
Tyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)IC50 (µMol)5.63000.70004.58049.4500AID409687
Tyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)IC50 (µMol)4.41000.00053.49849.7600AID391031; AID409686
Nitric oxide synthase, inducibleHomo sapiens (human)IC50 (µMol)37.00000.00022.319010.0000AID241425
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (98)

Processvia Protein(s)Taxonomy
positive regulation of gene expressionTissue factorHomo sapiens (human)
positive regulation of interleukin-8 productionTissue factorHomo sapiens (human)
positive regulation of endothelial cell proliferationTissue factorHomo sapiens (human)
activation of plasma proteins involved in acute inflammatory responseTissue factorHomo sapiens (human)
activation of blood coagulation via clotting cascadeTissue factorHomo sapiens (human)
activation of cysteine-type endopeptidase activity involved in apoptotic processTissue factorHomo sapiens (human)
blood coagulationTissue factorHomo sapiens (human)
positive regulation of platelet-derived growth factor receptor signaling pathwayTissue factorHomo sapiens (human)
protein processingTissue factorHomo sapiens (human)
positive regulation of cell migrationTissue factorHomo sapiens (human)
positive regulation of TOR signalingTissue factorHomo sapiens (human)
positive regulation of angiogenesisTissue factorHomo sapiens (human)
positive regulation of positive chemotaxisTissue factorHomo sapiens (human)
cytokine-mediated signaling pathwayTissue factorHomo sapiens (human)
negative regulation of transcription by RNA polymerase IITyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of cell population proliferationTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of tumor necrosis factor-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of lipid storageTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
B cell differentiationTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
T cell differentiationTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
erythrocyte differentiationTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
peptidyl-tyrosine dephosphorylationTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
insulin receptor recyclingTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of epidermal growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of tyrosine phosphorylation of STAT proteinTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
glucose homeostasisTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of macrophage differentiationTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
positive regulation of gluconeogenesisTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of inflammatory responseTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of T cell receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of chemotaxisTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
regulation of type II interferon-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of type II interferon-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of type I interferon-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of interleukin-6-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of ERK1 and ERK2 cascadeTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
regulation of hepatocyte growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of interleukin-2-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of interleukin-4-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of macrophage colony-stimulating factor signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of positive thymic T cell selectionTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
positive regulation of endoplasmic reticulum stress-induced intrinsic apoptotic signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
positive regulation of PERK-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of platelet-derived growth factor receptor-beta signaling pathwayTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
negative regulation of receptor signaling pathway via JAK-STATTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
positive regulation of JUN kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of signal transductionTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
actin cytoskeleton organizationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of endocytosisTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of vascular endothelial growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulum unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of intracellular protein transportTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cellular response to unfolded proteinTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylationTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
platelet-derived growth factor receptor-beta signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor recyclingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of MAP kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of insulin receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of type I interferon-mediated signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
growth hormone receptor signaling pathway via JAK-STATTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of protein tyrosine kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of ERK1 and ERK2 cascadeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
regulation of hepatocyte growth factor receptor signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of endoplasmic reticulum stress-induced intrinsic apoptotic signaling pathwayTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of IRE1-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
negative regulation of PERK-mediated unfolded protein responseTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
peptidyl-tyrosine dephosphorylation involved in inactivation of protein kinase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
positive regulation of receptor catabolic processTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
response to hypoxiaNitric oxide synthase, inducibleHomo sapiens (human)
positive regulation of leukocyte mediated cytotoxicityNitric oxide synthase, inducibleHomo sapiens (human)
innate immune response in mucosaNitric oxide synthase, inducibleHomo sapiens (human)
arginine catabolic processNitric oxide synthase, inducibleHomo sapiens (human)
superoxide metabolic processNitric oxide synthase, inducibleHomo sapiens (human)
nitric oxide biosynthetic processNitric oxide synthase, inducibleHomo sapiens (human)
circadian rhythmNitric oxide synthase, inducibleHomo sapiens (human)
response to bacteriumNitric oxide synthase, inducibleHomo sapiens (human)
negative regulation of gene expressionNitric oxide synthase, inducibleHomo sapiens (human)
peptidyl-cysteine S-nitrosylationNitric oxide synthase, inducibleHomo sapiens (human)
prostaglandin secretionNitric oxide synthase, inducibleHomo sapiens (human)
positive regulation of interleukin-6 productionNitric oxide synthase, inducibleHomo sapiens (human)
positive regulation of interleukin-8 productionNitric oxide synthase, inducibleHomo sapiens (human)
regulation of cell population proliferationNitric oxide synthase, inducibleHomo sapiens (human)
negative regulation of protein catabolic processNitric oxide synthase, inducibleHomo sapiens (human)
defense response to bacteriumNitric oxide synthase, inducibleHomo sapiens (human)
regulation of cellular respirationNitric oxide synthase, inducibleHomo sapiens (human)
cell redox homeostasisNitric oxide synthase, inducibleHomo sapiens (human)
regulation of insulin secretionNitric oxide synthase, inducibleHomo sapiens (human)
defense response to Gram-negative bacteriumNitric oxide synthase, inducibleHomo sapiens (human)
positive regulation of killing of cells of another organismNitric oxide synthase, inducibleHomo sapiens (human)
cellular response to lipopolysaccharideNitric oxide synthase, inducibleHomo sapiens (human)
cellular response to type II interferonNitric oxide synthase, inducibleHomo sapiens (human)
cellular response to xenobiotic stimulusNitric oxide synthase, inducibleHomo sapiens (human)
regulation of cytokine production involved in inflammatory responseNitric oxide synthase, inducibleHomo sapiens (human)
negative regulation of blood pressureNitric oxide synthase, inducibleHomo sapiens (human)
response to hormoneNitric oxide synthase, inducibleHomo sapiens (human)
nitric oxide mediated signal transductionNitric oxide synthase, inducibleHomo sapiens (human)
response to lipopolysaccharideNitric oxide synthase, inducibleHomo sapiens (human)
inflammatory responseNitric oxide synthase, inducibleHomo sapiens (human)
positive regulation of guanylate cyclase activityNitric oxide synthase, inducibleHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (29)

Processvia Protein(s)Taxonomy
serine-type endopeptidase activityTissue factorHomo sapiens (human)
protease bindingTissue factorHomo sapiens (human)
protein bindingTissue factorHomo sapiens (human)
phospholipid bindingTissue factorHomo sapiens (human)
cytokine receptor activityTissue factorHomo sapiens (human)
protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
integrin bindingTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
protein bindingTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
protein kinase bindingTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
syntaxin bindingTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
receptor tyrosine kinase bindingTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
STAT family protein bindingTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
non-membrane spanning protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
RNA bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
insulin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
zinc ion bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
enzyme bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
receptor tyrosine kinase bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cadherin bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
ephrin receptor bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein phosphatase 2A bindingTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
non-membrane spanning protein tyrosine phosphatase activityTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
nitric-oxide synthase activityNitric oxide synthase, inducibleHomo sapiens (human)
protein bindingNitric oxide synthase, inducibleHomo sapiens (human)
calmodulin bindingNitric oxide synthase, inducibleHomo sapiens (human)
FMN bindingNitric oxide synthase, inducibleHomo sapiens (human)
heme bindingNitric oxide synthase, inducibleHomo sapiens (human)
tetrahydrobiopterin bindingNitric oxide synthase, inducibleHomo sapiens (human)
arginine bindingNitric oxide synthase, inducibleHomo sapiens (human)
protein homodimerization activityNitric oxide synthase, inducibleHomo sapiens (human)
metal ion bindingNitric oxide synthase, inducibleHomo sapiens (human)
flavin adenine dinucleotide bindingNitric oxide synthase, inducibleHomo sapiens (human)
NADP bindingNitric oxide synthase, inducibleHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (24)

Processvia Protein(s)Taxonomy
extracellular spaceTissue factorHomo sapiens (human)
plasma membraneTissue factorHomo sapiens (human)
external side of plasma membraneTissue factorHomo sapiens (human)
cell surfaceTissue factorHomo sapiens (human)
membraneTissue factorHomo sapiens (human)
collagen-containing extracellular matrixTissue factorHomo sapiens (human)
serine-type peptidase complexTissue factorHomo sapiens (human)
plasma membraneTissue factorHomo sapiens (human)
plasma membraneTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
nucleoplasmTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
endoplasmic reticulum-Golgi intermediate compartmentTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
cytosolTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
endosome lumenTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
nucleusTyrosine-protein phosphatase non-receptor type 2Homo sapiens (human)
plasma membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial matrixTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytosolTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
mitochondrial cristaTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endosome lumenTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
sorting endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmic side of endoplasmic reticulum membraneTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
protein-containing complexTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
endoplasmic reticulumTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
cytoplasmTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
early endosomeTyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)
nucleusNitric oxide synthase, inducibleHomo sapiens (human)
nucleoplasmNitric oxide synthase, inducibleHomo sapiens (human)
cytoplasmNitric oxide synthase, inducibleHomo sapiens (human)
peroxisomeNitric oxide synthase, inducibleHomo sapiens (human)
peroxisomal matrixNitric oxide synthase, inducibleHomo sapiens (human)
cytosolNitric oxide synthase, inducibleHomo sapiens (human)
cortical cytoskeletonNitric oxide synthase, inducibleHomo sapiens (human)
perinuclear region of cytoplasmNitric oxide synthase, inducibleHomo sapiens (human)
plasma membraneNitric oxide synthase, inducibleHomo sapiens (human)
nucleusNitric oxide synthase, inducibleHomo sapiens (human)
cytosolNitric oxide synthase, inducibleHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (45)

Assay IDTitleYearJournalArticle
AID538211Cytotoxicity against human A549 cells by MTT assay2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Ixorapeptide I and ixorapeptide II, bioactive peptides isolated from Ixora coccinea.
AID22426350 percent inhibitory concentration of compound to inhibit nitric oxide production induced by IFN-gamma in mouse macrophages2000Journal of medicinal chemistry, May-04, Volume: 43, Issue:9
Novel synthetic oleanane and ursane triterpenoids with various enone functionalities in ring A as inhibitors of nitric oxide production in mouse macrophages.
AID1519315Cytotoxicity against human CEM-DNR-bulk cells incubated for 72 hrs by MTS assay2020European journal of medicinal chemistry, Jan-01, Volume: 185Synthesis and biological evaluation of triterpenoid thiazoles derived from betulonic acid, dihydrobetulonic acid, and ursonic acid.
AID378285Antitubercular activity against Mycobacterium tuberculosis H37Rv ATCC 27294 by BACTEC 460 radiorespirometric assay2000Journal of natural products, Dec, Volume: 63, Issue:12
Oleanane triterpenes from Junellia tridens.
AID1187408Inhibition of LPS-induced NO production in mouse J774A1 cells compound preincubated for 1 hr before LPS treatment by Griess reaction2014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
Oleanolic acid analogs as NO, TNF-α and IL-1β inhibitors: synthesis, biological evaluation and docking studies.
AID266475Inhibition of rabbit muscle GPa2006Bioorganic & medicinal chemistry letters, Jun-01, Volume: 16, Issue:11
Pentacyclic triterpenes. Part 3: Synthesis and biological evaluation of oleanolic acid derivatives as novel inhibitors of glycogen phosphorylase.
AID538213Cytotoxicity against human MDA-MB-231 cells by MTT assay2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Ixorapeptide I and ixorapeptide II, bioactive peptides isolated from Ixora coccinea.
AID90586The compound was tested in vitro for its inhibition of the classical pathway activation of human complement; Not active1999Bioorganic & medicinal chemistry letters, Jul-19, Volume: 9, Issue:14
Synthesis and evaluation of potential complement inhibitory semisynthetic analogs of oleanolic acid.
AID201653Compound was tested for its cytotoxicity against human malignant melanoma cell line SK-MEL1999Bioorganic & medicinal chemistry letters, Jul-19, Volume: 9, Issue:14
Synthesis and evaluation of potential complement inhibitory semisynthetic analogs of oleanolic acid.
AID404873Inhibition of rabbit muscle glycogen phosphorylase A assessed as phosphate release from glucose-1-phosphate2008Journal of medicinal chemistry, Jun-26, Volume: 51, Issue:12
Naturally occurring pentacyclic triterpenes as inhibitors of glycogen phosphorylase: synthesis, structure-activity relationships, and X-ray crystallographic studies.
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.
AID391031Inhibition of human recombinant PTP1B after 30 mins2008Journal of natural products, Oct, Volume: 71, Issue:10
Triterpenoids from the leaves of Diospyros kaki (persimmon) and their inhibitory effects on protein tyrosine phosphatase 1B.
AID545992Inhibition of recombinant PTP1B expressed in Escherichia coli BL21 up to 5 ug/ml after 30 mins by spectrophotometry2010Journal of natural products, Nov-29, Volume: 73, Issue:11
Synthesis and biological evaluation of oleanolic acid derivatives as inhibitors of protein tyrosine phosphatase 1B.
AID1519309Cytotoxicity against human A549 cells incubated for 72 hrs by MTS assay2020European journal of medicinal chemistry, Jan-01, Volume: 185Synthesis and biological evaluation of triterpenoid thiazoles derived from betulonic acid, dihydrobetulonic acid, and ursonic acid.
AID402091Antiviral activity against HIV1 3B in human H9 cells after 4 days by p24 antigen ELISA1998Journal of natural products, Sep, Volume: 61, Issue:9
Anti-AIDS agents. 30. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoids.
AID1488673Hepatoprotective activity against APAP-induced cell injury in human HL-7702 cells assessed as increase in survival rate at 10 uM pre-incubated for 24 hrs before APAP addition and measured 6 hrs post APAP challenge by MTT assay2017Bioorganic & medicinal chemistry letters, 08-15, Volume: 27, Issue:16
Discovery and structure-activity relationship of auriculatone: A potent hepatoprotective agent against acetaminophen-induced liver injury.
AID426247Antiosteoclast activity in ICR mouse osteoblast like cells co-cultured with bone marrow cells assessed as effect on 1-alpha,25(OH)2D3-induced TRAP-positive osteoclast like multinucleated cell formation at 20 uM after 6 days medium replaced every 2 days re2009European journal of medicinal chemistry, Jul, Volume: 44, Issue:7
Synthesis and evaluation of a novel series of heterocyclic oleanolic acid derivatives with anti-osteoclast formation activity.
AID1519311Cytotoxicity against human K562-TAX cells incubated for 72 hrs by MTS assay2020European journal of medicinal chemistry, Jan-01, Volume: 185Synthesis and biological evaluation of triterpenoid thiazoles derived from betulonic acid, dihydrobetulonic acid, and ursonic acid.
AID545993Inhibition of recombinant PTP1B expressed in Escherichia coli BL21 after 30 mins by spectrophotometry2010Journal of natural products, Nov-29, Volume: 73, Issue:11
Synthesis and biological evaluation of oleanolic acid derivatives as inhibitors of protein tyrosine phosphatase 1B.
AID232987The compound was tested for its apoptotic activity; DNA migration observed as a smear in the lane1999Bioorganic & medicinal chemistry letters, Jul-19, Volume: 9, Issue:14
Synthesis and evaluation of potential complement inhibitory semisynthetic analogs of oleanolic acid.
AID1519310Cytotoxicity against human K562 cells incubated for 72 hrs by MTS assay2020European journal of medicinal chemistry, Jan-01, Volume: 185Synthesis and biological evaluation of triterpenoid thiazoles derived from betulonic acid, dihydrobetulonic acid, and ursonic acid.
AID538212Cytotoxicity against human MCF7 cells by MTT assay2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Ixorapeptide I and ixorapeptide II, bioactive peptides isolated from Ixora coccinea.
AID279274Antibacterial activity against Helicobacter pylori after 48 hrs2007Antimicrobial agents and chemotherapy, Feb, Volume: 51, Issue:2
In vitro and in vivo activities of Chios mastic gum extracts and constituents against Helicobacter pylori.
AID224273Percent inhibition of nitric oxide production induced by IFN-uM concentration2000Journal of medicinal chemistry, May-04, Volume: 43, Issue:9
Novel synthetic oleanane and ursane triterpenoids with various enone functionalities in ring A as inhibitors of nitric oxide production in mouse macrophages.
AID1436859Inhibition of LPS-induced tissue factor procoagulant activity in human THP1 cells preincubated for 1 hr followed by LPS addition measured after 5 hrs using factor 10a chromogenic substrate in presence of prothrombin complex2017Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4
Microbial hydroxylation and glycosylation of pentacyclic triterpenes as inhibitors on tissue factor procoagulant activity.
AID1519308Cytotoxicity against human BJ cells incubated for 72 hrs by MTS assay2020European journal of medicinal chemistry, Jan-01, Volume: 185Synthesis and biological evaluation of triterpenoid thiazoles derived from betulonic acid, dihydrobetulonic acid, and ursonic acid.
AID538210Cytotoxicity against human Ca9-22 cells by MTT assay2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Ixorapeptide I and ixorapeptide II, bioactive peptides isolated from Ixora coccinea.
AID1519306Cytotoxicity against human MRC5 cells incubated for 72 hrs by MTS assay2020European journal of medicinal chemistry, Jan-01, Volume: 185Synthesis and biological evaluation of triterpenoid thiazoles derived from betulonic acid, dihydrobetulonic acid, and ursonic acid.
AID1519307Cytotoxicity against human U2OS cells incubated for 72 hrs by MTS assay2020European journal of medicinal chemistry, Jan-01, Volume: 185Synthesis and biological evaluation of triterpenoid thiazoles derived from betulonic acid, dihydrobetulonic acid, and ursonic acid.
AID402093Therapeutic index, ratio of IC50 for human H9 cells to EC50 for HIV1 3B1998Journal of natural products, Sep, Volume: 61, Issue:9
Anti-AIDS agents. 30. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoids.
AID538209Cytotoxicity against human Hep3B cells by MTT assay2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Ixorapeptide I and ixorapeptide II, bioactive peptides isolated from Ixora coccinea.
AID1706906Inhibition of Ebola virus pseudoparticle GP HR2 domain-mediated viral entry into human 293T cells at 1 uM incubated for 72 hrs by Bright-Glo reagent based assay relative to control2020Journal of medicinal chemistry, 12-24, Volume: 63, Issue:24
Triterpenoid-Mediated Inhibition of Virus-Host Interaction: Is Now the Time for Discovering Viral Entry/Release Inhibitors from Nature?
AID1187409Cytotoxicity mouse RAW264.7 cells assessed as cell viability by MTT assay relative to control2014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
Oleanolic acid analogs as NO, TNF-α and IL-1β inhibitors: synthesis, biological evaluation and docking studies.
AID1519313Cytotoxicity against human HCT116 cells incubated for 72 hrs by MTS assay2020European journal of medicinal chemistry, Jan-01, Volume: 185Synthesis and biological evaluation of triterpenoid thiazoles derived from betulonic acid, dihydrobetulonic acid, and ursonic acid.
AID538208Cytotoxicity against human HepG2 cells by MTT assay2010Bioorganic & medicinal chemistry letters, Dec-15, Volume: 20, Issue:24
Ixorapeptide I and ixorapeptide II, bioactive peptides isolated from Ixora coccinea.
AID750462Antiviral activity against pseudo HCV infected in human 293T cells assessed as inhibition of HCV pseudo particles entry at 10 uM after 72 hrs by luciferase reporter gene assay2013Journal of medicinal chemistry, Jun-13, Volume: 56, Issue:11
Development of oleanane-type triterpenes as a new class of HCV entry inhibitors.
AID426248Antiosteoclast activity in ICR mouse osteoblast like cells co-cultured with bone marrow cells assessed as effect on 1-alpha,25(OH)2D3-induced TRAP-positive osteoclast like multinucleated cell formation at 2 uM after 6 days medium replaced every 2 days rel2009European journal of medicinal chemistry, Jul, Volume: 44, Issue:7
Synthesis and evaluation of a novel series of heterocyclic oleanolic acid derivatives with anti-osteoclast formation activity.
AID409687Inhibition of TCPTP by pNPP assay2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Oleanolic acid and its derivatives: new inhibitor of protein tyrosine phosphatase 1B with cellular activities.
AID241425Inhibition of inducible nitric oxide synthase in activated macrophages2005Bioorganic & medicinal chemistry letters, May-02, Volume: 15, Issue:9
Studies on the reactivity of CDDO, a promising new chemopreventive and chemotherapeutic agent: implications for a molecular mechanism of action.
AID1519312Cytotoxicity against p53 knockout human HCT116 cells incubated for 72 hrs by MTS assay2020European journal of medicinal chemistry, Jan-01, Volume: 185Synthesis and biological evaluation of triterpenoid thiazoles derived from betulonic acid, dihydrobetulonic acid, and ursonic acid.
AID1187407Inhibition of LPS-induced NO production in mouse RAW264.7 cells compound preincubated for 1 hr before LPS treatment by Griess reaction2014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
Oleanolic acid analogs as NO, TNF-α and IL-1β inhibitors: synthesis, biological evaluation and docking studies.
AID1519314Cytotoxicity against human CCRF-CEM cells incubated for 72 hrs by MTS assay2020European journal of medicinal chemistry, Jan-01, Volume: 185Synthesis and biological evaluation of triterpenoid thiazoles derived from betulonic acid, dihydrobetulonic acid, and ursonic acid.
AID1187410Cytotoxicity against mouse J774A1 cells assessed as cell viability by MTT assay relative to control2014Bioorganic & medicinal chemistry letters, Sep-01, Volume: 24, Issue:17
Oleanolic acid analogs as NO, TNF-α and IL-1β inhibitors: synthesis, biological evaluation and docking studies.
AID402092Cytotoxicity against mock-infected human H9 cells after 4 days1998Journal of natural products, Sep, Volume: 61, Issue:9
Anti-AIDS agents. 30. Anti-HIV activity of oleanolic acid, pomolic acid, and structurally related triterpenoids.
AID409686Inhibition of PTP1B by pNPP assay2008Bioorganic & medicinal chemistry, Sep-15, Volume: 16, Issue:18
Oleanolic acid and its derivatives: new inhibitor of protein tyrosine phosphatase 1B with cellular activities.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (40)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (7.50)18.2507
2000's16 (40.00)29.6817
2010's15 (37.50)24.3611
2020's6 (15.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 24.42

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

MetricThis Compound (vs All)
Research Demand Index24.42 (24.57)
Research Supply Index3.78 (2.92)
Research Growth Index4.87 (4.65)
Search Engine Demand Index26.67 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (24.42)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews2 (4.65%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other41 (95.35%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]