oleanolic acid 3-o-monoglucuronide

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

Description

oleanolic acid 3-O-monoglucuronide: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID Source	ID
PubMed CID	176079
CHEMBL ID	446866
CHEBI ID	37658
MeSH ID	M0208571

Synonyms (39)

Synonym
momordin ib
oleanolic acid 3-o-glucuronide
CHEBI:37658 ,
glycoside st-e
calenduloside e
oleanolic acid 3-o-beta-d-glucosiduronic acid
3-o-(beta-d-glucopyranuronosyl)oleanolic acid
28-hydroxy-28-oxoolean-12-en-3beta-yl beta-d-glucopyranosiduronic acid
oleanoic acid 3-o-glucuronide
silphioside f
C08964
26020-14-4
oleanolic acid 3-o-monoglucuronide
(2s,3s,4s,5r,6r)-6-[[(3s,4ar,6ar,6bs,8as,12as,14ar,14br)-8a-carboxy-4,4,6a,6b,11,11,14b-heptamethyl-1,2,3,4a,5,6,7,8,9,10,12,12a,14,14a-tetradecahydropicen-3-yl]oxy]-3,4,5-trihydroxyoxane-2-carboxylic acid
CHEMBL446866
beta-d-glucopyranosiduronic acid, (3beta)-17-carboxy-28-norolean-12-en-3-yl
oleanolic acid 3-o-beta-d-glucuronopyranoside
184358rycu ,
olean-12-en-28-oic acid, 3beta-(beta-d-glucopyranuronosyloxy)-
glucopyranosiduronic acid, 3beta-hydroxyolean-12-en-28-oic acid, beta-d-
unii-184358rycu
oleanolic acid 3-o-.beta.-d-glucuronopyranoside
.beta.-d-glucopyranosiduronic acid, (3.beta.)-17-carboxy-28-norolean-12-en-3-yl
28-desglucosylchikusetsusaponin iva
glucopyranosiduronic acid, 3.beta.-hydroxyolean-12-en-28-oic acid, .beta.-d-
olean-12-en-28-oic acid, 3.beta.-(.beta.-d-glucopyranuronosyloxy)-
3-o-(.beta.-d-glucopyranuronosyl)oleanolic acid
AC-34369
DTXSID90180668 ,
AKOS030528265
108322-31-2
Q27104421
HY-N6850
CS-0100275
MS-30872
b-d-glucopyranosiduronic acid,(3b)-17-carboxy-28-norolean-12-en-3-yl
momordin b
calendulosidee
dtxcid30103159

Research Excerpts

Pharmacokinetics

Excerpt	Reference	Relevance
" In the pharmacokinetic (PK) study, beagle dogs were given oral doses of calenduloside E (1."	( Pharmacokinetic study of calenduloside E and its active metabolite oleanolic acid in beagle dog using liquid chromatography-tandem mass spectrometry. Cheng, L; Fawcett, JP; Gu, J; Shi, M; Sun, X; Sun, Y; Xu, H; Yang, Y; Zhao, S, 2014)	0.4

Bioavailability

Excerpt	Reference	Relevance
" The bioavailability of 29 was significantly improved in comparison with its aglycon."	( Synthesis and anti-inflammatory activity of saponin derivatives of δ-oleanolic acid. Chen, C; Cheng, K; Dai, L; Hu, K; Li, H; Liu, L; Sun, H; Wen, X; Xu, Q; Yuan, H, 2021)	0.62

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

Class	Description
beta-D-glucosiduronic acid	A glucosiduronic acid resulting from the formal condensation of any substance with beta-D-glucuronic acid to form a glycosidic bond.
[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 (2)

Assay ID	Title	Year	Journal	Article
AID1235938	Cytotoxicity against human NCI-H460 cells incubated for 72 hrs by cell-titer 96 aqueous non-radioactive cell proliferation assay	2015	Journal of natural products, Aug-28, Volume: 78, Issue:8	Digging Deep for New Compounds from the Compass Plant, Silphium laciniatum.
AID1728066	Activation of AMPK in human Huh-7 cells assessed as increase in AMPK phosphorylation at Thr172 residue at 10 uM measured after 12 hrs by Western blot analysis	2021	European journal of medicinal chemistry, Jan-01, Volume: 209	Synthesis and anti-inflammatory activity of saponin derivatives of δ-oleanolic acid.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (21)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	5 (23.81)	18.2507
2000's	1 (4.76)	29.6817
2010's	8 (38.10)	24.3611
2020's	7 (33.33)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.50

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.

Metric	This Compound (vs All)
Research Demand Index	12.50 (24.57)
Research Supply Index	3.09 (2.92)
Research Growth Index	5.59 (4.65)
Search Engine Demand Index	0.00 (26.88)
Search Engine Supply Index	0.00 (0.95)

This Compound (12.50)

All Compounds (24.57)

Study Types

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	21 (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
ketanserin Ketanserin: A selective serotonin receptor antagonist with weak adrenergic receptor blocking properties. The drug is effective in lowering blood pressure in essential hypertension. It also inhibits platelet aggregation. It is well tolerated and is particularly effective in older patients.. ketanserin : A member of the class of quinazolines that is quinazoline-2,4(1H,3H)-dione which is substituted at position 3 by a 2-[4-(p-fluorobenzoyl)piperidin-1-yl]ethyl group.	2.31	1	aromatic ketone; organofluorine compound; piperidines; quinazolines	alpha-adrenergic antagonist; antihypertensive agent; cardiovascular drug; EC 3.4.21.26 (prolyl oligopeptidase) inhibitor; serotonergic antagonist
glycyrrhetinic acid [no description available]	2.31	1	cyclic terpene ketone; hydroxy monocarboxylic acid; pentacyclic triterpenoid	immunomodulator; plant metabolite
oleanolic acid [no description available]	4.32	18	hydroxy monocarboxylic acid; pentacyclic triterpenoid	plant metabolite
malondialdehyde Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.	2.06	1	dialdehyde	biomarker
glycyrrhizic acid glycyrrhizinic acid : A triterpenoid saponin that is the glucosiduronide derivative of 3beta-hydroxy-11-oxoolean-12-en-30-oic acid.	2.31	1	enone; glucosiduronic acid; pentacyclic triterpenoid; tricarboxylic acid; triterpenoid saponin	EC 3.4.21.5 (thrombin) inhibitor; plant metabolite
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.	1.98	1	D-glucopyranose	epitope; mouse metabolite
ursolic acid [no description available]	2.31	1	hydroxy monocarboxylic acid; pentacyclic triterpenoid	geroprotector; plant metabolite
betulinic acid [no description available]	2.31	1	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
hederagenin [no description available]	2.31	1	dihydroxy monocarboxylic acid; pentacyclic triterpenoid; sapogenin	plant metabolite
madecassic acid [no description available]	2.31	1	monocarboxylic acid; pentacyclic triterpenoid; tetrol	antioxidant; plant metabolite
maslinic acid (2Alpha,3beta)-2,3-dihydroxyolean-12-en-28-oic acid: from Luehea divaricata and Agrimonia eupatoria	2.31	1	dihydroxy monocarboxylic acid; pentacyclic triterpenoid	anti-inflammatory agent; antineoplastic agent; antioxidant; plant metabolite
p-methoxy-n-methylphenethylamine p-Methoxy-N-methylphenethylamine: A potent mast cell degranulator. It is involved in histamine release.. N,O-dimethyltyramine : A secondary amino compound that is tyramine in which the hydrogen of the phenolic hydroxy group has been replaced by a methyl group.	1.99	1	aromatic ether; secondary amino compound	metabolite
asiatic acid [no description available]	2.31	1	monocarboxylic acid; pentacyclic triterpenoid; triol	angiogenesis modulating agent; metabolite
scoparianoside b scoparianoside B: isolated from the fruit of Japanese Kochia scoparia; structure given in first source	2.31	1	triterpenoid saponin
glycosides [no description available]	2	1
capsaicin ALGRX-4975: an injectable capsaicin (TRPV1 receptor agonist) formulation for longlasting pain relief. capsaicinoid : A family of aromatic fatty amides produced as secondary metabolites by chilli peppers.	2	1	capsaicinoid	non-narcotic analgesic; TRPV1 agonist; voltage-gated sodium channel blocker
ginsenosides ginsenoside : Triterpenoid saponins with a dammarane-like skeleton originally isolated from ginseng (Panax) species. Use of the term has been extended to include semi-synthetic derivatives.	2.61	2
beta-escin [no description available]	4.01	12
corosolic acid [no description available]	2.31	1	triterpenoid	metabolite
oleanane oleanane: from the aerial roots of Ficus microcarpa; structure in first source	2.21	1	terpenoid fundamental parent; triterpene
kalopanax saponin b kalopanax saponin B: isolated from Kalopanax septemlobus; structure given in first source. kalopanaxsaponin B : A triterpenoid saponin with hederagenin as the aglycone part. It has been isolated from the stem bark of Kalopanax pictus.	2.31	1	carboxylic ester; pentacyclic triterpenoid; triterpenoid saponin	anti-inflammatory agent; plant metabolite
ginsenoside ro ginsenoside Ro: from ginseng; RN given refers to ginsenoside Ro, (all-D)-isomer	2.66	2	triterpenoid saponin	metabolite
chikusetsu saponin iva chikusetsu saponin IVa: from the tubers of Hemsleya pengxianensis (Cucurbitaceae)	2.97	4	triterpenoid saponin	metabolite
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.	2.41	1
madecassoside [no description available]	2.31	1	carboxylic ester; pentacyclic triterpenoid; trisaccharide derivative; triterpenoid saponin	anti-inflammatory agent; antioxidant; antirheumatic drug; plant metabolite; vulnerary
ziyuglycoside i ziyuglycoside I: isolated from the leaves of Hex pupurea; structure in first source	2.31	1
ziyuglycoside ii ziyuglycoside II: isolated from Sanguisorba officinalis; structure in first source	2.31	1

Condition	Relationship Strength	Studies
Carcinoma, Non-Small Cell Lung [description not available]	2.11	1
Carcinoma, Non-Small-Cell Lung A heterogeneous aggregate of at least three distinct histological types of lung cancer, including SQUAMOUS CELL CARCINOMA; ADENOCARCINOMA; and LARGE CELL CARCINOMA. They are dealt with collectively because of their shared treatment strategy.	2.11	1
Injury, Myocardial Reperfusion [description not available]	2.76	2
Cerebral Ischemia [description not available]	2.41	1
Injury, Ischemia-Reperfusion [description not available]	2.41	1
Brain Ischemia Localized reduction of blood flow to brain tissue due to arterial obstruction or systemic hypoperfusion. This frequently occurs in conjunction with brain hypoxia (HYPOXIA, BRAIN). Prolonged ischemia is associated with BRAIN INFARCTION.	2.41	1
Reperfusion Injury Adverse functional, metabolic, or structural changes in tissues that result from the restoration of blood flow to the tissue (REPERFUSION) following ISCHEMIA.	2.41	1
Atherogenesis [description not available]	2.6	1
Atherosclerosis A thickening and loss of elasticity of the walls of ARTERIES that occurs with formation of ATHEROSCLEROTIC PLAQUES within the ARTERIAL INTIMA.	2.6	1
Fatty Liver, Nonalcoholic [description not available]	3.14	1
Innate Inflammatory Response [description not available]	3.14	1
Inflammation A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.	3.14	1
Non-alcoholic Fatty Liver Disease Fatty liver finding without excessive ALCOHOL CONSUMPTION.	3.14	1
Extravascular Hemolysis [description not available]	2.21	1
B16 Melanoma [description not available]	2.21	1
Cancer of Skin [description not available]	2.21	1
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.21	1
Skin Neoplasms Tumors or cancer of the SKIN.	2.21	1
Hepatocellular Carcinoma [description not available]	2.31	1
Cancer of Liver [description not available]	2.31	1
Carcinoma, Hepatocellular A primary malignant neoplasm of epithelial liver cells. It ranges from a well-differentiated tumor with EPITHELIAL CELLS indistinguishable from normal HEPATOCYTES to a poorly differentiated neoplasm. The cells may be uniform or markedly pleomorphic, or form GIANT CELLS. Several classification schemes have been suggested.	2.31	1
Liver Neoplasms Tumors or cancer of the LIVER.	2.31	1
Genital Herpes [description not available]	2.05	1
Viral Diseases [description not available]	2.05	1
Herpes Genitalis Infection of the genitals (GENITALIA) with HERPES SIMPLEX VIRUS in either the males or the females.	2.05	1
Virus Diseases A general term for diseases caused by viruses.	2.05	1
Alloxan Diabetes [description not available]	1.99	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2	1
Intestinal Obstruction Any impairment, arrest, or reversal of the normal flow of INTESTINAL CONTENTS toward the ANAL CANAL.	2	1

chemdatabank.com