Page last updated: 2024-11-12

rutundic acid

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

Description

rutundic acid: isolated from the leaves of Hex pupurea; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID12315075
CHEMBL ID1271052
CHEBI ID70684
SCHEMBL ID1045049
MeSH IDM0465572

Synonyms (23)

Synonym
CHEMBL1271052 ,
chebi:70684 ,
rotundic acid
(3beta,4alpha)-3,19,23-trihydroxyurs-12-en-28-oic acid
20137-37-5
urs-12-en-28-oic acid, 3,19,23-trihydroxy-, (3beta,4alpha)-
bdbm50391059
S9514 ,
SCHEMBL1045049
rutundic acid
DTXSID80173963
AKOS032949054
Q27139015
(1r,2r,4as,6ar,6as,6br,8ar,9r,10s,12ar,14bs)-1,10-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-2,3,4,5,6,6a,7,8,8a,10,11,12,13,14b-tetradecahydropicene-4a-carboxylic acid
mfcd13186912
i1exo1ic acid
CS-0019536
HY-N2217
22-deoxyilexolic acid a
3ss,19a,23-trihydroxyurs-12-en-28-oic acid
MS-29090
(1r,2r,4as,6as,6br,8ar,9r,10s,12ar,12br,14bs)-1,10-dihydroxy-9-(hydroxymethyl)-1,2,6a,6b,9,12a-hexamethyl-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-4a(2h)-carboxylic acid
A879816

Research Excerpts

Pharmacokinetics

ExcerptReferenceRelevance
" Although many studies about the total saponins have been reported, the absorption triterpenoids and pharmacokinetic behaviors were unclear."( Rapid profiling and pharmacokinetic studies of multiple potential bioactive triterpenoids in rat plasma using UPLC/Q-TOF-MS/MS after oral administration of Ilicis Rotundae Cortex extract.
Jin, J; Li, H; Liu, Z; Ruan, Q; Tong, Y; Xuan, S; Yang, B; Zhao, Z, 2018
)
0.48
" In this study, we evaluated the pharmacokinetic interactions of rotundic acid with pedunculoside and other ingredients from Ilicis Rotundae Cortex with rotundic acid and pedunculoside, and preliminarily investigated the effects of gut microbiota on their pharmacokinetics using a pseudo-germ-free rat model."( Effects of Gut Microbiota and Ingredient-Ingredient Interaction on the Pharmacokinetic Properties of Rotundic Acid and Pedunculoside.
Chen, X; Cui, H; Jin, J; Li, H; Liu, Z; Ruan, Q; Xuan, S; Yang, B; Zhao, Z, 2019
)
0.51
"These findings indicated that verapamil could significantly affect the pharmacokinetic profiles of RA in rats."( Influence of verapamil on the pharmacokinetics of rotundic acid in rats and its potential mechanism.
Ci, X; Gu, Y; Liu, C; Ma, H; Shang, H; Si, D; Sun, Y; Wang, Z, 2021
)
0.62

Bioavailability

ExcerptReferenceRelevance
" The poor bioavailability limits its further development and potential clinic application."( Influence of verapamil on the pharmacokinetics of rotundic acid in rats and its potential mechanism.
Ci, X; Gu, Y; Liu, C; Ma, H; Shang, H; Si, D; Sun, Y; Wang, Z, 2021
)
0.62
" It was demonstrated that P-gp and CYP3A were involved in the transport and metabolism of RA, which might contribute to the low oral bioavailability of RA."( Influence of verapamil on the pharmacokinetics of rotundic acid in rats and its potential mechanism.
Ci, X; Gu, Y; Liu, C; Ma, H; Shang, H; Si, D; Sun, Y; Wang, Z, 2021
)
0.62
[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
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 (1)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Tyrosine-protein phosphatase non-receptor type 1Homo sapiens (human)IC50 (µMol)20.10000.00053.49849.7600AID683328
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (27)

Processvia Protein(s)Taxonomy
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (12)

Processvia Protein(s)Taxonomy
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID1668310Inhibition of LPS-induced TNF-alpha production in human BV2 cells at 250 ug/ml preincubated for 4 hrs followed by LPS stimulation and measured after 24 hrs by ELISA2020Bioorganic & medicinal chemistry letters, 06-15, Volume: 30, Issue:12
Betulin isolated from Pyrola incarnata Fisch. inhibited lipopolysaccharide (LPS)-induced neuroinflammation with the guidance of computer-aided drug design.
AID745203Cytotoxicity against human SPC-A1 cells after 24 hrs by MTT assay2013Bioorganic & medicinal chemistry letters, May-01, Volume: 23, Issue:9
Design, synthesis and cytotoxicity of cell death mechanism of rotundic acid derivatives.
AID745200Cytotoxicity against human HeLa cells after 24 hrs by MTT assay2013Bioorganic & medicinal chemistry letters, May-01, Volume: 23, Issue:9
Design, synthesis and cytotoxicity of cell death mechanism of rotundic acid derivatives.
AID745199Cytotoxicity against human NCI-H446 cells after 24 hrs by MTT assay2013Bioorganic & medicinal chemistry letters, May-01, Volume: 23, Issue:9
Design, synthesis and cytotoxicity of cell death mechanism of rotundic acid derivatives.
AID527185Cytotoxicity against human fibroblast cells at 10 uM after 48 hrs2010Journal of natural products, Oct-22, Volume: 73, Issue:10
Cytotoxic Hexacyclic Triterpene Acids from Euscaphis japonica.
AID745201Cytotoxicity against human HepG2 cells after 24 hrs by MTT assay2013Bioorganic & medicinal chemistry letters, May-01, Volume: 23, Issue:9
Design, synthesis and cytotoxicity of cell death mechanism of rotundic acid derivatives.
AID527184Cytotoxicity against human CEM cells at 10 uM after 48 hrs2010Journal of natural products, Oct-22, Volume: 73, Issue:10
Cytotoxic Hexacyclic Triterpene Acids from Euscaphis japonica.
AID745202Cytotoxicity against human A375 cells after 24 hrs by MTT assay2013Bioorganic & medicinal chemistry letters, May-01, Volume: 23, Issue:9
Design, synthesis and cytotoxicity of cell death mechanism of rotundic acid derivatives.
AID527181Cytotoxicity against human MCF7 cells at 10 uM after 48 hrs2010Journal of natural products, Oct-22, Volume: 73, Issue:10
Cytotoxic Hexacyclic Triterpene Acids from Euscaphis japonica.
AID527182Cytotoxicity against human NCI-H460 cells at 10 uM after 48 hrs2010Journal of natural products, Oct-22, Volume: 73, Issue:10
Cytotoxic Hexacyclic Triterpene Acids from Euscaphis japonica.
AID1668306Cytotoxicity against human BV2 cells assessed as survival rate at 250 ug/ml2020Bioorganic & medicinal chemistry letters, 06-15, Volume: 30, Issue:12
Betulin isolated from Pyrola incarnata Fisch. inhibited lipopolysaccharide (LPS)-induced neuroinflammation with the guidance of computer-aided drug design.
AID527183Cytotoxicity against human HT-29 cells at 10 uM after 48 hrs2010Journal of natural products, Oct-22, Volume: 73, Issue:10
Cytotoxic Hexacyclic Triterpene Acids from Euscaphis japonica.
AID683328Inhibition of human recombinant PTP1B using p-nitrophenyl phosphate as substrate assessed as p-nitrophenol release after 30 mins2012Bioorganic & medicinal chemistry letters, Oct-01, Volume: 22, Issue:19
Rhododendric acid A, a new ursane-type PTP1B inhibitor from the endangered plant Rhododendron brachycarpum G. Don.
AID1436764Anticomplement activity in New Zealand White rabbit erythrocytes assessed as concentration required for 50% hemolytic inhibition by alternative pathway preincubated for 10 mins with normal human serum followed by erythrocyte addition measured after 30 min2017Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4
Anticomplement triterpenoids from the roots of Ilex asprella.
AID1668311Inhibition of LPS-induced IL-1beta production in human BV2 cells at 250 ug/ml preincubated for 4 hrs followed by LPS stimulation and measured after 24 hrs by ELISA2020Bioorganic & medicinal chemistry letters, 06-15, Volume: 30, Issue:12
Betulin isolated from Pyrola incarnata Fisch. inhibited lipopolysaccharide (LPS)-induced neuroinflammation with the guidance of computer-aided drug design.
AID1436763Anticomplement activity in sheep erythrocytes assessed as concentration required for 50% hemolytic inhibition by classic pathway preincubated for 10 mins with guinea pig serum followed by erythrocyte addition measured after 30 mins by spectrophotometer2017Bioorganic & medicinal chemistry letters, 02-15, Volume: 27, Issue:4
Anticomplement triterpenoids from the roots of Ilex asprella.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (24)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's1 (4.17)29.6817
2010's15 (62.50)24.3611
2020's8 (33.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

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%
Other24 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]