Page last updated: 2024-11-08

asperlicin

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

Description

asperlicin: cholecystokinin antagonist; isolated from Aspergillus alliaceus; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3035433
CHEMBL ID283117
SCHEMBL ID1004269
MeSH IDM0134382

Synonyms (19)

Synonym
asperlicin
93413-04-8
(s-(2alpha,9beta,9(r*),9alpha,beta))-6,7-dihydro-7-((2,3,9,9a-tetrahydro-9-hydroxy-2-(2-methylpropyl)-3-oxo-1h-imidazo(1,2-a)indol-9-yl)methyl)quinazolino(3,2-a)(1,4)benzodiazepine-5,13-dione
quinazolino(3,2-a)(1,4)benzodiazepine-5,13-dione, 6,7-dihydro-7-((2,3,9,9a-tetrahydro-9-hydroxy-2-(2-methylpropyl)-3-oxo-1h-imidazo(1,2-a)indol-9-yl)methyl)-, (2s-(2alpha,9beta,9(r*),9abeta))-
CHEMBL283117 ,
(7s)-7-[[(2s,3as,4s)-4-hydroxy-2-(2-methylpropyl)-1-oxo-3,3a-dihydro-2h-imidazo[1,2-a]indol-4-yl]methyl]-6,7-dihydroquinazolino[3,2-a][1,4]benzodiazepine-5,13-dione
bdbm50019777
7-(9-hydroxy-2-isobutyl-3-oxo-2,3,9,9a-tetrahydro-1h-imidazo[1,2-a]indol-9-ylmethyl)-6,7-dihydro-6,8,13a-triaza-benzo[3,4]cyclohepta[1,2-b]naphthalene-5,13-dione
7-(9-hydroxy-2-isobutyl-3-oxo-2,3,9,9a-tetrahydro-1h-imidazo[1,2-a]indol-9-ylmethyl)-6,7-dihydro-6,8,13a-triaza-benzo[3,4]cyclohepta[1,2-b]naphthalene-5,13-dione(asperlicin)
7-(9-hydroxy-2-isobutyl-3-oxo-2,3,9,9a-tetrahydro-1h-imidazo[1,2-a]indol-9-ylmethyl)-6,7-dihydro-6,8,13a-triaza-benzo[3,4]cyclohepta[1,2-b]naphthalene-5,13-dione (asperlicin)
unii-u0mje9lrxv
u0mje9lrxv ,
(7s)-6,7-dihydro-7-(((2s,9s,9as)-2,3,9,9a-tetrahydro-9-hydroxy-2-(2-methylpropyl)-3-oxo-1h-imidazo(1,2-a)indol-9-yl)methyl)quinazolino(3,2-a)(1,4)benzodiazepine-5,13-dione
(-)-asperlicin
asperlicin [mi]
SCHEMBL1004269
1-benzyl-3(r)-methylpiperazine
DTXSID20918456
Q4807912

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
" Discovery of the natural product Asperlicin provided a new class of non-peptidal CCK antagonists, but oral bioavailability in this class remained elusive."( Molecular design of potent specific antagonists for the gastrin and cholecystokinin receptors.
Evans, BE, 1991
)
0.28

Dosage Studied

ExcerptRelevanceReference
" L364718 caused a parallel rightward shift of the dose-response curve of CCK8."( Effect of L364718, a new CCK antagonist, on amylase secretion in isolated rat pancreatic acini.
Chowdhury, P; Hosotani, R; McKay, D; Rayford, PL, 1988
)
0.27
" The caerulein dose-response curve was gradually shifted to the right by increasing doses of CR 1409, indicating competitive-like kinetics."( Comparative effects of CCK receptor antagonists on rat pancreatic secretion in vivo.
Grendell, JH; Niederau, C; Niederau, M; Strohmeyer, G, 1989
)
0.28
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (19)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Gamma-aminobutyric acid receptor subunit piRattus norvegicus (Norway rat)IC50 (µMol)50.00000.00010.507510.0000AID40817
Gamma-aminobutyric acid receptor subunit beta-1Rattus norvegicus (Norway rat)IC50 (µMol)50.00000.00010.507510.0000AID40817
Gamma-aminobutyric acid receptor subunit deltaRattus norvegicus (Norway rat)IC50 (µMol)50.00000.00010.507510.0000AID40817
Gamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)IC50 (µMol)50.00000.00010.505710.0000AID40817
Gamma-aminobutyric acid receptor subunit alpha-5Rattus norvegicus (Norway rat)IC50 (µMol)50.00000.00010.497310.0000AID40817
Gamma-aminobutyric acid receptor subunit alpha-3Rattus norvegicus (Norway rat)IC50 (µMol)50.00000.00010.507510.0000AID40817
Gamma-aminobutyric acid receptor subunit gamma-1Rattus norvegicus (Norway rat)IC50 (µMol)50.00000.00010.498810.0000AID40817
Gamma-aminobutyric acid receptor subunit alpha-2Rattus norvegicus (Norway rat)IC50 (µMol)50.00000.00010.504610.0000AID40817
Gamma-aminobutyric acid receptor subunit alpha-4Rattus norvegicus (Norway rat)IC50 (µMol)50.00000.00010.507510.0000AID40817
Gamma-aminobutyric acid receptor subunit gamma-3Rattus norvegicus (Norway rat)IC50 (µMol)50.00000.00010.507510.0000AID40817
Gamma-aminobutyric acid receptor subunit alpha-6Rattus norvegicus (Norway rat)IC50 (µMol)50.00000.00010.507510.0000AID40817
Cholecystokinin receptor type ARattus norvegicus (Norway rat)IC50 (µMol)1.40000.00000.43624.3000AID52410; AID52419
Gastrin/cholecystokinin type B receptorRattus norvegicus (Norway rat)IC50 (µMol)1.40000.00010.24801.4000AID52410; AID52419
Cholecystokinin receptor type AHomo sapiens (human)IC50 (µMol)1.40000.00010.30381.9000AID402081; AID50523
Gamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)IC50 (µMol)50.00000.00010.506510.0000AID40817
Gamma-aminobutyric acid receptor subunit beta-3Rattus norvegicus (Norway rat)IC50 (µMol)50.00000.00010.505710.0000AID40817
Gamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)IC50 (µMol)50.00000.00010.507510.0000AID40817
GABA theta subunitRattus norvegicus (Norway rat)IC50 (µMol)50.00000.00010.507510.0000AID40817
Gamma-aminobutyric acid receptor subunit epsilonRattus norvegicus (Norway rat)IC50 (µMol)50.00000.00010.507510.0000AID40817
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
neuron migrationCholecystokinin receptor type AHomo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayCholecystokinin receptor type AHomo sapiens (human)
axonogenesisCholecystokinin receptor type AHomo sapiens (human)
forebrain developmentCholecystokinin receptor type AHomo sapiens (human)
cholecystokinin signaling pathwayCholecystokinin receptor type AHomo sapiens (human)
G protein-coupled receptor signaling pathwayCholecystokinin receptor type AHomo sapiens (human)
cellular response to hormone stimulusCholecystokinin receptor type AHomo sapiens (human)
regulation of hormone secretionCholecystokinin receptor type AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (3)

Processvia Protein(s)Taxonomy
cholecystokinin receptor activityCholecystokinin receptor type AHomo sapiens (human)
peptide hormone bindingCholecystokinin receptor type AHomo sapiens (human)
peptide bindingCholecystokinin receptor type AHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
plasma membraneGamma-aminobutyric acid receptor subunit gamma-2Rattus norvegicus (Norway rat)
nucleoplasmCholecystokinin receptor type AHomo sapiens (human)
cytosolCholecystokinin receptor type AHomo sapiens (human)
plasma membraneCholecystokinin receptor type AHomo sapiens (human)
membraneCholecystokinin receptor type AHomo sapiens (human)
plasma membraneCholecystokinin receptor type AHomo sapiens (human)
plasma membraneGamma-aminobutyric acid receptor subunit alpha-1Rattus norvegicus (Norway rat)
plasma membraneGamma-aminobutyric acid receptor subunit beta-2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (9)

Assay IDTitleYearJournalArticle
AID229422Selectivity of binding to pancreatic CCK and brain benzodiazepine receptors, ratio of IC501987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
Design of nonpeptidal ligands for a peptide receptor: cholecystokinin antagonists.
AID52410Half-maximal inhibition of [125I]-CCK-33 binding to rat pancreas cholecystokinin receptor1987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
Design of nonpeptidal ligands for a peptide receptor: cholecystokinin antagonists.
AID40817Displacement of [3H]diazepam from rat brain GABA-A benzodiazepine receptor1987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
Design of nonpeptidal ligands for a peptide receptor: cholecystokinin antagonists.
AID52275Half-maximal inhibition of [125I]CCK-33 binding to guinea pig brain(cortex) cholecystokinin receptor1987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
Design of nonpeptidal ligands for a peptide receptor: cholecystokinin antagonists.
AID52419Inhibition of [125I]CCK binding to rat pancreatic Cholecystokinin receptor1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Cholecystokinin antagonists. Synthesis of asperlicin analogues with improved potency and water solubility.
AID52404Inhibition of [125I]CCK binding to Cholecystokinin receptor in guinea pig cortical membranes at 100 uM1986Journal of medicinal chemistry, Oct, Volume: 29, Issue:10
Cholecystokinin antagonists. Synthesis of asperlicin analogues with improved potency and water solubility.
AID402081Inhibition of cholecystokinin A receptor1998Journal of natural products, Aug, Volume: 61, Issue:8
Recent natural products based drug development: a pharmaceutical industry perspective.
AID50523Antagonistic activity against cholecystokinin type A receptor1993Journal of medicinal chemistry, Jul-23, Volume: 36, Issue:15
Excursions in drug discovery.
AID132604In vivo activity on the basis of the ability to antagonize CCK-8 inhibition of charcoal meal gastric emptying in mice after oral administration1987Journal of medicinal chemistry, Jul, Volume: 30, Issue:7
Design of nonpeptidal ligands for a peptide receptor: cholecystokinin antagonists.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (37)

TimeframeStudies, This Drug (%)All Drugs %
pre-199020 (54.05)18.7374
1990's11 (29.73)18.2507
2000's4 (10.81)29.6817
2010's1 (2.70)24.3611
2020's1 (2.70)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%
Reviews7 (18.92%)6.00%
Case Studies1 (2.70%)4.05%
Observational0 (0.00%)0.25%
Other29 (78.38%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]