Page last updated: 2024-11-08

pseudoprotopine

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

Description

pseudoprotopine: from Thalictrum delavayi; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

FloraRankFlora DefinitionFamilyFamily Definition
ThalictrumgenusA plant genus of the family RANUNCULACEAE. Members contain isoquinoline alkaloids and triterpene glycosides.[MeSH]RanunculaceaeThe buttercup plant family of the order RANUNCULALES, class MAGNOLIOPSIDA. The leaves are usually alternate and stalkless. The flowers usually have two to five free sepals and may be radially symmetrical or irregular.[MeSH]

Cross-References

ID SourceID
PubMed CID185559
CHEMBL ID486179
MeSH IDM0385700

Synonyms (13)

Synonym
c20h19no5
24240-05-9
CHEMBL486179
7,13a-secoberbin-13a-one, 7-methyl-2,3:10,11-bis(methylenedioxy)-
bis(1,3)benzodioxolo(5,6-c:5',6'-g)azecin-14(6h)-one, 5,7,8,15-tetrahydro-6-methyl-
pseudoprotopine
bdbm50377937
DTXSID00178935
NCGC00385257-01
ncgc00385257-01_c20h19no5_1,3-benzodioxolo[5,6-c][1,3]benzodioxolo[5,6-g]azecin-14(6h)-one, 5,7,8,15-tetrahydro-6-methyl-
14-methyl-7,9,20,22-tetraoxa-14-azapentacyclo[15.7.0.04,12.06,10.019,23]tetracosa-1(24),4,6(10),11,17,19(23)-hexaen-2-one
pseudo protopine
AKOS040735231

Research Excerpts

Toxicity

ExcerptReferenceRelevance
" To ensure a safe and effective product, botanical dietary supplements should be developed in a manner analogous to pharmaceuticals that involves identification of mechanisms of action and active constituents, chemical standardization based on the active compounds, biological standardization based on pharmacological activity, preclinical evaluation of toxicity and potential for drug-botanical interactions, metabolism of active compounds, and finally, clinical studies of safety and efficacy."( Development of Safe and Effective Botanical Dietary Supplements.
van Breemen, RB, 2015
)
0.42

Bioavailability

ExcerptReferenceRelevance
"The ATP-binding cassette transporter P-glycoprotein (P-gp) is known to limit both brain penetration and oral bioavailability of many chemotherapy drugs."( A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
Ambudkar, SV; Brimacombe, KR; Chen, L; Gottesman, MM; Guha, R; Hall, MD; Klumpp-Thomas, C; Lee, OW; Lee, TD; Lusvarghi, S; Robey, RW; Shen, M; Tebase, BG, 2019
)
0.51
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cytochrome P450 3A4Homo sapiens (human)IC50 (µMol)80.00000.00011.753610.0000AID380506
Cytochrome P450 2D6Homo sapiens (human)Ki0.07800.00011.19868.0000AID1254736
[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)
5-hydroxytryptamine receptor 1AHomo sapiens (human)EC50 (µMol)100.00000.00010.25718.0000AID380503
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (40)

Processvia Protein(s)Taxonomy
lipid hydroxylationCytochrome P450 3A4Homo sapiens (human)
lipid metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid catabolic processCytochrome P450 3A4Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid metabolic processCytochrome P450 3A4Homo sapiens (human)
cholesterol metabolic processCytochrome P450 3A4Homo sapiens (human)
androgen metabolic processCytochrome P450 3A4Homo sapiens (human)
estrogen metabolic processCytochrome P450 3A4Homo sapiens (human)
alkaloid catabolic processCytochrome P450 3A4Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 3A4Homo sapiens (human)
calcitriol biosynthetic process from calciolCytochrome P450 3A4Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D metabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D catabolic processCytochrome P450 3A4Homo sapiens (human)
retinol metabolic processCytochrome P450 3A4Homo sapiens (human)
retinoic acid metabolic processCytochrome P450 3A4Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 3A4Homo sapiens (human)
aflatoxin metabolic processCytochrome P450 3A4Homo sapiens (human)
oxidative demethylationCytochrome P450 3A4Homo sapiens (human)
behavioral fear response5-hydroxytryptamine receptor 1AHomo sapiens (human)
G protein-coupled receptor signaling pathway5-hydroxytryptamine receptor 1AHomo sapiens (human)
adenylate cyclase-inhibiting serotonin receptor signaling pathway5-hydroxytryptamine receptor 1AHomo sapiens (human)
serotonin receptor signaling pathway5-hydroxytryptamine receptor 1AHomo sapiens (human)
gamma-aminobutyric acid signaling pathway5-hydroxytryptamine receptor 1AHomo sapiens (human)
positive regulation of cell population proliferation5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of serotonin secretion5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of vasoconstriction5-hydroxytryptamine receptor 1AHomo sapiens (human)
exploration behavior5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of dopamine metabolic process5-hydroxytryptamine receptor 1AHomo sapiens (human)
serotonin metabolic process5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of hormone secretion5-hydroxytryptamine receptor 1AHomo sapiens (human)
regulation of behavior5-hydroxytryptamine receptor 1AHomo sapiens (human)
chemical synaptic transmission5-hydroxytryptamine receptor 1AHomo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messenger5-hydroxytryptamine receptor 1AHomo sapiens (human)
xenobiotic metabolic processCytochrome P450 2D6Homo sapiens (human)
steroid metabolic processCytochrome P450 2D6Homo sapiens (human)
cholesterol metabolic processCytochrome P450 2D6Homo sapiens (human)
estrogen metabolic processCytochrome P450 2D6Homo sapiens (human)
coumarin metabolic processCytochrome P450 2D6Homo sapiens (human)
alkaloid metabolic processCytochrome P450 2D6Homo sapiens (human)
alkaloid catabolic processCytochrome P450 2D6Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 2D6Homo sapiens (human)
isoquinoline alkaloid metabolic processCytochrome P450 2D6Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 2D6Homo sapiens (human)
retinol metabolic processCytochrome P450 2D6Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 2D6Homo sapiens (human)
negative regulation of bindingCytochrome P450 2D6Homo sapiens (human)
oxidative demethylationCytochrome P450 2D6Homo sapiens (human)
negative regulation of cellular organofluorine metabolic processCytochrome P450 2D6Homo sapiens (human)
arachidonic acid metabolic processCytochrome P450 2D6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (28)

Processvia Protein(s)Taxonomy
monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
steroid bindingCytochrome P450 3A4Homo sapiens (human)
iron ion bindingCytochrome P450 3A4Homo sapiens (human)
protein bindingCytochrome P450 3A4Homo sapiens (human)
steroid hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
retinoic acid 4-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
oxidoreductase activityCytochrome P450 3A4Homo sapiens (human)
oxygen bindingCytochrome P450 3A4Homo sapiens (human)
enzyme bindingCytochrome P450 3A4Homo sapiens (human)
heme bindingCytochrome P450 3A4Homo sapiens (human)
vitamin D3 25-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
caffeine oxidase activityCytochrome P450 3A4Homo sapiens (human)
quinine 3-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
testosterone 6-beta-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1-alpha,25-dihydroxyvitamin D3 23-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 8,9 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 11,12 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 14,15 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
aromatase activityCytochrome P450 3A4Homo sapiens (human)
vitamin D 24-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 2-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1,8-cineole 2-exo-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
G protein-coupled serotonin receptor activity5-hydroxytryptamine receptor 1AHomo sapiens (human)
protein binding5-hydroxytryptamine receptor 1AHomo sapiens (human)
receptor-receptor interaction5-hydroxytryptamine receptor 1AHomo sapiens (human)
neurotransmitter receptor activity5-hydroxytryptamine receptor 1AHomo sapiens (human)
serotonin binding5-hydroxytryptamine receptor 1AHomo sapiens (human)
monooxygenase activityCytochrome P450 2D6Homo sapiens (human)
iron ion bindingCytochrome P450 2D6Homo sapiens (human)
oxidoreductase activityCytochrome P450 2D6Homo sapiens (human)
oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygenCytochrome P450 2D6Homo sapiens (human)
heme bindingCytochrome P450 2D6Homo sapiens (human)
anandamide 8,9 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
anandamide 11,12 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
anandamide 14,15 epoxidase activityCytochrome P450 2D6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (8)

Processvia Protein(s)Taxonomy
cytoplasmCytochrome P450 3A4Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 3A4Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 3A4Homo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 1AHomo sapiens (human)
synapse5-hydroxytryptamine receptor 1AHomo sapiens (human)
plasma membrane5-hydroxytryptamine receptor 1AHomo sapiens (human)
dendrite5-hydroxytryptamine receptor 1AHomo sapiens (human)
mitochondrionCytochrome P450 2D6Homo sapiens (human)
endoplasmic reticulumCytochrome P450 2D6Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 2D6Homo sapiens (human)
cytoplasmCytochrome P450 2D6Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 2D6Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (28)

Assay IDTitleYearJournalArticle
AID1347160Primary screen NINDS Rhodamine qHTS for Zika virus inhibitors2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1296008Cytotoxic Profiling of Annotated Libraries Using Quantitative High-Throughput Screening2020SLAS discovery : advancing life sciences R & D, 01, Volume: 25, Issue:1
Cytotoxic Profiling of Annotated and Diverse Chemical Libraries Using Quantitative High-Throughput Screening.
AID1346986P-glycoprotein substrates identified in KB-3-1 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1347159Primary screen GU Rhodamine qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID1346987P-glycoprotein substrates identified in KB-8-5-11 adenocarcinoma cell line, qHTS therapeutic library screen2019Molecular pharmacology, 11, Volume: 96, Issue:5
A High-Throughput Screen of a Library of Therapeutics Identifies Cytotoxic Substrates of P-glycoprotein.
AID1254736Competitive inhibition of CYP2D6 (unknown origin) using dextromethorphan substrate2015Journal of medicinal chemistry, Nov-12, Volume: 58, Issue:21
Development of Safe and Effective Botanical Dietary Supplements.
AID400864Spasmolytic activity in isolated guinea pig ileum assessed as spasmogen-induced inhibition of smooth muscle contraction
AID380503Displacement of [3H]8-OH-DPAT from human recombinant 5HT1A receptor expressed in CHO cells2006Journal of natural products, Mar, Volume: 69, Issue:3
Alkaloids from Eschscholzia californica and their capacity to inhibit binding of [3H]8-Hydroxy-2-(di-N-propylamino)tetralin to 5-HT1A receptors in Vitro.
AID400829Spasmolytic activity against guinea pig ileum assessed as inhibition of spasmogen-induced contraction at 10 ug
AID378591Antiplasmodial activity against multi drug-resistant Plasmodium falciparum K1 in erythrocytes by [3H]hypoxanthine uptake2000Journal of natural products, Dec, Volume: 63, Issue:12
In vitro antiplasmodial, antiamoebic, and cytotoxic activities of some monomeric isoquinoline alkaloids.
AID334627Inhibition of acetylcholine-induced contraction in guinea pig ileum preincubated for 10 mins before acetylcholine challenge
AID380506Inhibition of CYP3A42006Journal of natural products, Mar, Volume: 69, Issue:3
Alkaloids from Eschscholzia californica and their capacity to inhibit binding of [3H]8-Hydroxy-2-(di-N-propylamino)tetralin to 5-HT1A receptors in Vitro.
AID400831Spasmolytic activity against guinea pig ileum assessed as inhibition of spasmogen-induced contraction
AID334628Inhibition of acetylcholine-induced contraction in guinea pig ileum preincubated for 20 mins before acetylcholine challenge
AID400830Spasmolytic activity against guinea pig ileum assessed as inhibition of spasmogen-induced contraction at 50 ug
AID493705Cytotoxicity against human A549 cells by SRB assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Benzylisoquinoline alkaloids from the tubers of Corydalis ternata and their cytotoxicity.
AID334629Inhibition of histamine-induced contraction in guinea pig ileum
AID378593Cytotoxicity against human KB cells after 72 hrs2000Journal of natural products, Dec, Volume: 63, Issue:12
In vitro antiplasmodial, antiamoebic, and cytotoxic activities of some monomeric isoquinoline alkaloids.
AID378592Antiamnesic activity against Entamoeba histolytica NIH 200 after 72 hrs by microdilution technique2000Journal of natural products, Dec, Volume: 63, Issue:12
In vitro antiplasmodial, antiamoebic, and cytotoxic activities of some monomeric isoquinoline alkaloids.
AID493706Cytotoxicity against human SKOV3 cells by SRB assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Benzylisoquinoline alkaloids from the tubers of Corydalis ternata and their cytotoxicity.
AID493707Cytotoxicity against human SK-MEL-2 cells by SRB assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Benzylisoquinoline alkaloids from the tubers of Corydalis ternata and their cytotoxicity.
AID400863Spasmolytic activity in isolated guinea pig ileum assessed as spasmogen-induced inhibition of smooth muscle contraction at 10 ug
AID493708Cytotoxicity against human HCT15 cells by SRB assay2010Bioorganic & medicinal chemistry letters, Aug-01, Volume: 20, Issue:15
Benzylisoquinoline alkaloids from the tubers of Corydalis ternata and their cytotoxicity.
AID400862Spasmolytic activity in isolated guinea pig ileum assessed as spasmogen-induced inhibition of smooth muscle contraction at 10 ug
AID632313Antiinflammatory activity in mouse RAW264.7 cells assessed as inhibition of LPS-induced nitric oxide production after 24 hrs by griess assay2011Bioorganic & medicinal chemistry letters, Dec-01, Volume: 21, Issue:23
Alkaloids from Chelidonium majus and their inhibitory effects on LPS-induced NO production in RAW264.7 cells.
AID632314Cytotoxicity against mouse RAW264.7 cells assessed as cell viability at 50 uM after 24 hrs by MTT assay2011Bioorganic & medicinal chemistry letters, Dec-01, Volume: 21, Issue:23
Alkaloids from Chelidonium majus and their inhibitory effects on LPS-induced NO production in RAW264.7 cells.
AID377193Antimicrobial activity against Staphylococcus aureus 4222 with norA KLE 820(3) mutation2000Journal of natural products, Aug, Volume: 63, Issue:8
5'-Methoxyhydnocarpin-D and pheophorbide A: Berberis species components that potentiate berberine growth inhibition of resistant Staphylococcus aureus.
AID334626Inhibition of acetylcholine-induced contraction in guinea pig ileum preincubated for 5 mins before acetylcholine challenge
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's4 (40.00)29.6817
2010's4 (40.00)24.3611
2020's2 (20.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.10

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 Index12.10 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.10)

All Compounds (24.57)

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%
Other13 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]