methyl ursolate profile

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

ID Source	ID
PubMed CID	636516
CHEMBL ID	260673
SCHEMBL ID	3917132
MeSH ID	M0423959

Synonym
MEGXP0_001727
915-32-2
ursolic acid, methyl ester
(1s,2r,4as,6as,6br,8ar,10s,12ar,14bs)-10-hydroxy-1,2,6a,6b,9,9,12a-heptamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydro-2h-picene-4a-carboxylic acid methyl ester
methyl (1s,2r,4as,6ar,6as,6br,8ar,10s,12ar,14bs)-10-hydroxy-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-carboxylate
CHEMBL260673
bdbm50058810
methyl ursolate
AKOS016036340
SCHEMBL3917132
mfcd00017383
DTXSID60348374
ursolic acid methylester with hplc

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Carbonic anhydrase 2	Bos taurus (cattle)	Ki	10.0000	0.0025	1.1325	7.5858	AID1188769
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
angiotensin-activated signaling pathway	Carbonic anhydrase 2	Bos taurus (cattle)
regulation of monoatomic anion transport	Carbonic anhydrase 2	Bos taurus (cattle)
regulation of intracellular pH	Carbonic anhydrase 2	Bos taurus (cattle)
positive regulation of dipeptide transmembrane transport	Carbonic anhydrase 2	Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
zinc ion binding	Carbonic anhydrase 2	Bos taurus (cattle)
cyanamide hydratase activity	Carbonic anhydrase 2	Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
cytoplasm	Carbonic anhydrase 2	Bos taurus (cattle)
plasma membrane	Carbonic anhydrase 2	Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (29)

Assay ID	Title	Year	Journal	Article
AID327757	Cytotoxicity against human Panc28 cells	2008	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 18, Issue:8	Structure-dependent inhibition of bladder and pancreatic cancer cell growth by 2-substituted glycyrrhetinic and ursolic acid derivatives.
AID1066417	Cytotoxicity against human A549 cells after 96 hrs by SRB assay	2014	European journal of medicinal chemistry, Jan-24, Volume: 72	The chemical and biological potential of C ring modified triterpenoids.
AID327755	Cytotoxicity against human KU7 cells	2008	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 18, Issue:8	Structure-dependent inhibition of bladder and pancreatic cancer cell growth by 2-substituted glycyrrhetinic and ursolic acid derivatives.
AID1066418	Cytotoxicity against human HT-29 cells after 96 hrs by SRB assay	2014	European journal of medicinal chemistry, Jan-24, Volume: 72	The chemical and biological potential of C ring modified triterpenoids.
AID377097	Cytotoxicity against human VA13 cells after 48 hrs by WST-8 assay	2005	Journal of natural products, Feb, Volume: 68, Issue:2	Three new triterpenes from Nerium oleander and biological activity of the isolated compounds.
AID689291	Cytotoxicity against human AsPC1 cells after 72 hrs by MTT assay	2012	Bioorganic & 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.
AID1188769	Inhibition of bovine erythrocyte carbonic anhydrase 2 using 4-nitrophenyl acetate substrate by photometric assay	2014	European journal of medicinal chemistry, Oct-30, Volume: 86	Sulfamates of methyl triterpenoates are effective and competitive inhibitors of carbonic anhydrase II.
AID327756	Cytotoxicity against human Panc1 cells	2008	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 18, Issue:8	Structure-dependent inhibition of bladder and pancreatic cancer cell growth by 2-substituted glycyrrhetinic and ursolic acid derivatives.
AID377095	Cytotoxicity against human A549 cells assessed as cell viability after 24 hrs by MTT assay	2005	Journal of natural products, Feb, Volume: 68, Issue:2	Three new triterpenes from Nerium oleander and biological activity of the isolated compounds.
AID1888104	Inhibition 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 control	2022	European journal of medicinal chemistry, Jan-05, Volume: 227	Discovery and radiosensitization research of ursolic acid derivatives as SENP1 inhibitors.
AID458321	Inhibition of human recombinant 11beta-HSD2 expressed in HEK293 cells assessed as reduction of cortisone to cortisol conversion at 20 uM by scintillation counting	2010	Bioorganic & medicinal chemistry, Feb-15, Volume: 18, Issue:4	11beta-Hydroxysteroid dehydrogenase 1 inhibiting constituents from Eriobotrya japonica revealed by bioactivity-guided isolation and computational approaches.
AID1243948	Cytotoxicity against human HT-29 cells assessed as cell survival after 96 hrs by SRB assay	2015	European journal of medicinal chemistry, Aug-28, Volume: 101	Incorporation of a Michael acceptor enhances the antitumor activity of triterpenoic acids.
AID1243947	Cytotoxicity against human A549 cells assessed as cell survival after 96 hrs by SRB assay	2015	European journal of medicinal chemistry, Aug-28, Volume: 101	Incorporation of a Michael acceptor enhances the antitumor activity of triterpenoic acids.
AID1066419	Cytotoxicity against human A2780 cells after 96 hrs by SRB assay	2014	European journal of medicinal chemistry, Jan-24, Volume: 72	The chemical and biological potential of C ring modified triterpenoids.
AID1250813	Antiproliferative activity against human MCF7 cells after 48 hrs by CCK-8 assay	2015	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20	Design, synthesis, and biofunctional evaluation of novel pentacyclic triterpenes bearing O-[4-(1-piperazinyl)-4-oxo-butyryl moiety as antiproliferative agents.
AID377098	Cytotoxicity against human Hep G2 cells after 48 hrs by WST-8 assay	2005	Journal of natural products, Feb, Volume: 68, Issue:2	Three new triterpenes from Nerium oleander and biological activity of the isolated compounds.
AID377094	Antiinflammatory activity against human A549 cells assessed as inhibition of IL-1-alpha-induced ICAM1 expression treated after 1 hr before IL1alpha challenge	2005	Journal of natural products, Feb, Volume: 68, Issue:2	Three new triterpenes from Nerium oleander and biological activity of the isolated compounds.
AID452564	Cytotoxicity against human NTUB1 cells after 72 hrs by MTT assay	2009	Bioorganic & 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.
AID1243945	Cytotoxicity against human 518A2 cells assessed as cell survival after 96 hrs by SRB assay	2015	European journal of medicinal chemistry, Aug-28, Volume: 101	Incorporation of a Michael acceptor enhances the antitumor activity of triterpenoic acids.
AID1066421	Cytotoxicity against human 518A2 cells after 96 hrs by SRB assay	2014	European journal of medicinal chemistry, Jan-24, Volume: 72	The chemical and biological potential of C ring modified triterpenoids.
AID1243949	Cytotoxicity against human MCF7 cells assessed as cell survival after 96 hrs by SRB assay	2015	European journal of medicinal chemistry, Aug-28, Volume: 101	Incorporation of a Michael acceptor enhances the antitumor activity of triterpenoic acids.
AID1066416	Cytotoxicity against human MCF7 cells after 96 hrs by SRB assay	2014	European journal of medicinal chemistry, Jan-24, Volume: 72	The chemical and biological potential of C ring modified triterpenoids.
AID327754	Cytotoxicity against human 253JBV cells	2008	Bioorganic & medicinal chemistry letters, Apr-15, Volume: 18, Issue:8	Structure-dependent inhibition of bladder and pancreatic cancer cell growth by 2-substituted glycyrrhetinic and ursolic acid derivatives.
AID1250814	Antiproliferative activity against human HeLa cells after 48 hrs by CCK-8 assay	2015	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20	Design, synthesis, and biofunctional evaluation of novel pentacyclic triterpenes bearing O-[4-(1-piperazinyl)-4-oxo-butyryl moiety as antiproliferative agents.
AID1243946	Cytotoxicity against human 8505C cells assessed as cell survival after 96 hrs by SRB assay	2015	European journal of medicinal chemistry, Aug-28, Volume: 101	Incorporation of a Michael acceptor enhances the antitumor activity of triterpenoic acids.
AID377096	Cytotoxicity against human WI 38 cells after 48 hrs by WST-8 assay	2005	Journal of natural products, Feb, Volume: 68, Issue:2	Three new triterpenes from Nerium oleander and biological activity of the isolated compounds.
AID1250815	Antiproliferative activity against human A549 cells after 48 hrs by CCK-8 assay	2015	Bioorganic & medicinal chemistry letters, Oct-15, Volume: 25, Issue:20	Design, synthesis, and biofunctional evaluation of novel pentacyclic triterpenes bearing O-[4-(1-piperazinyl)-4-oxo-butyryl moiety as antiproliferative agents.
AID1066420	Cytotoxicity against human 8505C cells after 96 hrs by SRB assay	2014	European journal of medicinal chemistry, Jan-24, Volume: 72	The chemical and biological potential of C ring modified triterpenoids.
AID1888106	Cytotoxicity against human HeLa cells assessed as inhibition of cell growth incubated for 72 hrs by CCK-8 assay	2022	European journal of medicinal chemistry, Jan-05, Volume: 227	Discovery and radiosensitization research of ursolic acid derivatives as SENP1 inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	0 (0.00)	18.2507
2000's	5 (35.71)	29.6817
2010's	8 (57.14)	24.3611
2020's	1 (7.14)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	14 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
acetazolamide Acetazolamide: One of the CARBONIC ANHYDRASE INHIBITORS that is sometimes effective against absence seizures. It is sometimes useful also as an adjunct in the treatment of tonic-clonic, myoclonic, and atonic seizures, particularly in women whose seizures occur or are exacerbated at specific times in the menstrual cycle. However, its usefulness is transient often because of rapid development of tolerance. Its antiepileptic effect may be due to its inhibitory effect on brain carbonic anhydrase, which leads to an increased transneuronal chloride gradient, increased chloride current, and increased inhibition. (From Smith and Reynard, Textbook of Pharmacology, 1991, p337)	2.1	1	monocarboxylic acid amide; sulfonamide; thiadiazoles	anticonvulsant; diuretic; EC 4.2.1.1 (carbonic anhydrase) inhibitor
diazepam Diazepam: A benzodiazepine with anticonvulsant, anxiolytic, sedative, muscle relaxant, and amnesic properties and a long duration of action. Its actions are mediated by enhancement of GAMMA-AMINOBUTYRIC ACID activity.. diazepam : A 1,4-benzodiazepinone that is 1,3-dihydro-2H-1,4-benzodiazepin-2-one substituted by a chloro group at position 7, a methyl group at position 1 and a phenyl group at position 5.	3.03	1	1,4-benzodiazepinone; organochlorine compound	anticonvulsant; anxiolytic drug; environmental contaminant; sedative; xenobiotic
glycyrrhetinic acid [no description available]	2.52	2	cyclic terpene ketone; hydroxy monocarboxylic acid; pentacyclic triterpenoid	immunomodulator; plant metabolite
oleanolic acid [no description available]	4.24	6	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
paclitaxel Taxus: Genus of coniferous yew trees or shrubs, several species of which have medicinal uses. Notable is the Pacific yew, Taxus brevifolia, which is used to make the anti-neoplastic drug taxol (PACLITAXEL).	2.44	2	taxane diterpenoid; tetracyclic diterpenoid	antineoplastic agent; human metabolite; metabolite; microtubule-stabilising agent
staurosporine [no description available]	2.1	1	indolocarbazole alkaloid; organic heterooctacyclic compound	apoptosis inducer; bacterial metabolite; EC 2.7.11.13 (protein kinase C) inhibitor; geroprotector
ursolic acid [no description available]	3.46	7	hydroxy monocarboxylic acid; pentacyclic triterpenoid	geroprotector; plant metabolite
betulinic acid [no description available]	3.38	2	hydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-HIV agent; anti-inflammatory agent; antimalarial; antineoplastic agent; EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor; plant metabolite
platanic acid platanic acid: inhibits HIV replication; isolated from Syzigium claviflorum; structure in first source. platanic acid : A pentacyclic triterpenoid that is 30-norlupan-28-oic acid substituted by a 3beta-hydroxy and an oxo group at position 20. It is isolated from the leaves of Syzygium claviflorum and exhibits anti-HIV activity.	2.11	1	hydroxy monocarboxylic acid; methyl ketone; pentacyclic triterpenoid	anti-HIV agent; metabolite
baicalin [no description available]	2.03	1	dihydroxyflavone; glucosiduronic acid; glycosyloxyflavone; monosaccharide derivative	antiatherosclerotic agent; antibacterial agent; anticoronaviral agent; antineoplastic agent; antioxidant; cardioprotective agent; EC 2.7.7.48 (RNA-directed RNA polymerase) inhibitor; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; ferroptosis inhibitor; neuroprotective agent; non-steroidal anti-inflammatory drug; plant metabolite; prodrug
betulin betulin: isolated from various white birch bark (BETULA). betulin : A pentacyclic triterpenoid that is lupane having a double bond at position 20(29) as well as 3beta-hydroxy and 28-hydroxymethyl substituents.	2.02	1	diol; pentacyclic triterpenoid	analgesic; anti-inflammatory agent; antineoplastic agent; antiviral agent; metabolite
beta-amyrin beta-amyrin: alpha-amyrin is also available; a 5 ring triterpene derived from oleanane that differs from alpha-amyrin in having the 29-carbon at the 20 position; RN given refers to (3 beta)-isomer. beta-amyrin : A pentacyclic triterpenoid that is oleanane substituted at the 3beta-position by a hydroxy group and containing a double bond between positions 12 and 13. It is one of the most commonly occurring triterpenoids in higher plants.	3.03	1	pentacyclic triterpenoid; secondary alcohol	Aspergillus metabolite; plant metabolite
alpha-amyrin alpha-amyrin: beta-amyrin is also available; a 5 ring triterpene derived from taraxasterol that differs from beta-amyrin in having the 29-carbon at the 19 position. alpha-amyrin : A pentacyclic triterpenoid that is ursane which contains a double bond between positions 12 and 13 and in which the hydrogen at the 3beta position is substituted by a hydroxy group.	2.02	1	pentacyclic triterpenoid; secondary alcohol
Tormentic acid tormentic acid: aglycone of Rosamultin	2.05	1	triterpenoid	metabolite
betulinic acid methyl ester betulinic acid methyl ester: from the roots of Saussurea lappa; structure in first source	2.1	1	triterpenoid
maslinic acid (2Alpha,3beta)-2,3-dihydroxyolean-12-en-28-oic acid: from Luehea divaricata and Agrimonia eupatoria	2.1	1	dihydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory agent; antineoplastic agent; antioxidant; plant metabolite
uvaol uvaol: from Vauquelinia corymbosa (Rosaceae)	2.44	2	triterpenoid	metabolite
asiatic acid [no description available]	2.11	1	monocarboxylic acid; pentacyclic triterpenoid; triol	angiogenesis modulating agent; metabolite
gefitinib [no description available]	2.11	1	aromatic ether; monochlorobenzenes; monofluorobenzenes; morpholines; quinazolines; secondary amino compound; tertiary amino compound	antineoplastic agent; epidermal growth factor receptor antagonist
scoparianoside b scoparianoside B: isolated from the fruit of Japanese Kochia scoparia; structure given in first source	2.41	1	triterpenoid saponin
sitosterol, (3beta)-isomer Sobatum: tradename; active fraction of Solanum trilobatum; reduces side-effects of radiation-induced toxicity. sitosterol : A member of the class of phytosterols that is stigmast-5-ene substituted by a beta-hydroxy group at position 3.	2.05	1	3beta-hydroxy-Delta(5)-steroid; 3beta-sterol; C29-steroid; phytosterols; stigmastane sterol	anticholesteremic drug; antioxidant; mouse metabolite; plant metabolite; sterol methyltransferase inhibitor
Bardoxolone [no description available]	2.11	1	cyclohexenones
ganoderic acid a [no description available]	2.05	1	triterpenoid
sesquiterpenes [no description available]	2.01	1
rutin Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.	2.03	1	disaccharide derivative; quercetin O-glucoside; rutinoside; tetrahydroxyflavone	antioxidant; metabolite
3 beta-o-acetylursolic acid [no description available]	2.79	3	triterpenoid
corosolic acid [no description available]	2.05	1	triterpenoid	metabolite
11-keto-boswellic acid [no description available]	2.05	1
3-oxo-12-ursen-28-oic acid 3-oxo-12-ursen-28-oic acid: from Potentilla chinensis	2.46	2	triterpenoid
oleanderolide oleanderolide: oleanane-type triterpene from Nerium oleander; structure in first source	2.46	2
acetyl-11-ketoboswellic acid acetyl-11-ketoboswellic acid: a 5-lipoxygenase inhibitor; structure given in first source	2.05	1	triterpenoid
2-hydroxyursolic acid 2-hydroxyursolic acid: isolated from the stem bark of Physocarpus intermedius; structure in first source	3.03	1

Condition	Relationship Strength	Studies
Bladder Cancer [description not available]	2.04	1
Cancer of Pancreas [description not available]	2.46	2
Urinary Bladder Neoplasms Tumors or cancer of the URINARY BLADDER.	2.04	1
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).	2.46	2
Rheumatoid Arthritis [description not available]	7.1	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.1	1
Anasarca [description not available]	2.1	1
Arthritis, Rheumatoid A chronic systemic disease, primarily of the joints, marked by inflammatory changes in the synovial membranes and articular structures, widespread fibrinoid degeneration of the collagen fibers in mesenchymal tissues, and by atrophy and rarefaction of bony structures. Etiology is unknown, but autoimmune mechanisms have been implicated.	2.1	1
Edema Abnormal fluid accumulation in TISSUES or body cavities. Most cases of edema are present under the SKIN in SUBCUTANEOUS TISSUE.	2.1	1

methyl ursolate

Description

Cross-References

Synonyms (13)

Research Excerpts

Protein Targets (1)

Inhibition Measurements

Biological Processes (4)

Molecular Functions (2)

Ceullar Components (2)

Bioassays (29)

Research

Studies (14)

Study Types

methyl ursolate

Description

Cross-References

Synonyms (13)

Research Excerpts

Protein Targets (1)

Inhibition Measurements

Biological Processes (4)

Molecular Functions (2)

Ceullar Components (2)

Bioassays (29)

Research

Studies (14)

Study Types

Related Drugs (32)

Related Conditions (9)