Compounds > l 363301
Page last updated: 2024-11-12

l 363301

Cross-References

ID SourceID
PubMed CID9918828
CHEMBL ID421362
MeSH IDM0121055

Synonyms (8)

Synonym
l-363301
CHEMBL421362 ,
l-363,301
bdbm50065453
l-361,301
(5s,8s,11s,14r,17s,19as)-11-(4-amino-butyl)-5,17-dibenzyl-8-((r)-1-hydroxy-ethyl)-14-(1h-indol-3-ylmethyl)-tetradecahydro-3a,6,9,12,15,18-hexaaza-cyclopentacyclooctadecene-4,7,10,13,16,19-hexaone
cyclo-(pro-phe-d-trp-lys-thr-phe)
cyclo[pro(1)-phe(2)-d-trp(3)-lys(4)-thr(5)-phe(6)]

Research Excerpts

Bioavailability

ExcerptReferenceRelevance
"An increasing number of macrocyclic peptides that cross biological membranes are being reported, suggesting that it might be possible to develop peptides into orally bioavailable therapeutics; however, current understanding of what makes macrocyclic peptides cell permeable is still limited."( Exploring experimental and computational markers of cyclic peptides: Charting islands of permeability.
Chaousis, S; Colless, B; Craik, DJ; Liras, S; Northfield, SE; Price, DA; Swedberg, JE; Wang, CK, 2015)		0.42
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (5)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Somatostatin receptor type 1Homo sapiens (human)Ki0.81550.00030.41232.3920AID203080; AID203390
Somatostatin receptor type 2Homo sapiens (human)Ki0.00290.00000.40914.7200AID203088; AID203409
Somatostatin receptor type 4Homo sapiens (human)Ki0.55000.00060.27333.2000AID203238; AID203570
Somatostatin receptor type 3Homo sapiens (human)Ki0.12740.00010.03200.1290AID203227; AID203551
Somatostatin receptor type 5Homo sapiens (human)Ki0.03240.00010.44794.0700AID203583; AID203709
[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)
Somatostatin receptor type 1Homo sapiens (human)Kd4.57000.01022.29014.5700AID203077
Somatostatin receptor type 2Homo sapiens (human)Kd0.00080.00080.00080.0008AID203083
Somatostatin receptor type 4Homo sapiens (human)Kd8.91308.91308.91308.9130AID203234
Somatostatin receptor type 3Homo sapiens (human)Kd0.52500.52504.61738.7096AID203224
Somatostatin receptor type 5Homo sapiens (human)Kd0.00760.00760.89291.7783AID203579
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (23)

Processvia Protein(s)Taxonomy
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerSomatostatin receptor type 1Homo sapiens (human)
glutamate receptor signaling pathwaySomatostatin receptor type 1Homo sapiens (human)
spermatogenesisSomatostatin receptor type 1Homo sapiens (human)
negative regulation of cell population proliferationSomatostatin receptor type 1Homo sapiens (human)
cerebellum developmentSomatostatin receptor type 1Homo sapiens (human)
forebrain developmentSomatostatin receptor type 1Homo sapiens (human)
somatostatin signaling pathwaySomatostatin receptor type 1Homo sapiens (human)
response to starvationSomatostatin receptor type 1Homo sapiens (human)
cellular response to leukemia inhibitory factorSomatostatin receptor type 1Homo sapiens (human)
cellular response to estradiol stimulusSomatostatin receptor type 1Homo sapiens (human)
neuropeptide signaling pathwaySomatostatin receptor type 1Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerSomatostatin receptor type 2Homo sapiens (human)
adenylate cyclase-inhibiting G protein-coupled receptor signaling pathwaySomatostatin receptor type 2Homo sapiens (human)
spermatogenesisSomatostatin receptor type 2Homo sapiens (human)
negative regulation of cell population proliferationSomatostatin receptor type 2Homo sapiens (human)
cerebellum developmentSomatostatin receptor type 2Homo sapiens (human)
peristalsisSomatostatin receptor type 2Homo sapiens (human)
forebrain developmentSomatostatin receptor type 2Homo sapiens (human)
somatostatin signaling pathwaySomatostatin receptor type 2Homo sapiens (human)
response to starvationSomatostatin receptor type 2Homo sapiens (human)
cellular response to glucocorticoid stimulusSomatostatin receptor type 2Homo sapiens (human)
cellular response to estradiol stimulusSomatostatin receptor type 2Homo sapiens (human)
neuropeptide signaling pathwaySomatostatin receptor type 2Homo sapiens (human)
G protein-coupled receptor signaling pathwaySomatostatin receptor type 4Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerSomatostatin receptor type 4Homo sapiens (human)
negative regulation of cell population proliferationSomatostatin receptor type 4Homo sapiens (human)
cell migrationSomatostatin receptor type 4Homo sapiens (human)
forebrain developmentSomatostatin receptor type 4Homo sapiens (human)
somatostatin signaling pathwaySomatostatin receptor type 4Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeSomatostatin receptor type 4Homo sapiens (human)
positive regulation of arachidonic acid secretionSomatostatin receptor type 4Homo sapiens (human)
negative regulation of adenylate cyclase-activating G protein-coupled receptor signaling pathwaySomatostatin receptor type 4Homo sapiens (human)
neuropeptide signaling pathwaySomatostatin receptor type 4Homo sapiens (human)
cellular response to glucocorticoid stimulusSomatostatin receptor type 4Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerSomatostatin receptor type 3Homo sapiens (human)
cell-cell signalingSomatostatin receptor type 3Homo sapiens (human)
spermatogenesisSomatostatin receptor type 3Homo sapiens (human)
negative regulation of cell population proliferationSomatostatin receptor type 3Homo sapiens (human)
hormone-mediated apoptotic signaling pathwaySomatostatin receptor type 3Homo sapiens (human)
cerebellum developmentSomatostatin receptor type 3Homo sapiens (human)
forebrain developmentSomatostatin receptor type 3Homo sapiens (human)
somatostatin signaling pathwaySomatostatin receptor type 3Homo sapiens (human)
response to starvationSomatostatin receptor type 3Homo sapiens (human)
cellular response to glucocorticoid stimulusSomatostatin receptor type 3Homo sapiens (human)
cellular response to estradiol stimulusSomatostatin receptor type 3Homo sapiens (human)
neuropeptide signaling pathwaySomatostatin receptor type 3Homo sapiens (human)
G protein-coupled receptor signaling pathwaySomatostatin receptor type 5Homo sapiens (human)
G protein-coupled receptor signaling pathway, coupled to cyclic nucleotide second messengerSomatostatin receptor type 5Homo sapiens (human)
negative regulation of cell population proliferationSomatostatin receptor type 5Homo sapiens (human)
positive regulation of cytokinesisSomatostatin receptor type 5Homo sapiens (human)
somatostatin signaling pathwaySomatostatin receptor type 5Homo sapiens (human)
cellular response to glucocorticoid stimulusSomatostatin receptor type 5Homo sapiens (human)
neuropeptide signaling pathwaySomatostatin receptor type 5Homo sapiens (human)
regulation of insulin secretionSomatostatin receptor type 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (6)

Processvia Protein(s)Taxonomy
somatostatin receptor activitySomatostatin receptor type 1Homo sapiens (human)
protein bindingSomatostatin receptor type 1Homo sapiens (human)
neuropeptide bindingSomatostatin receptor type 1Homo sapiens (human)
protein bindingSomatostatin receptor type 2Homo sapiens (human)
PDZ domain bindingSomatostatin receptor type 2Homo sapiens (human)
somatostatin receptor activitySomatostatin receptor type 2Homo sapiens (human)
neuropeptide bindingSomatostatin receptor type 2Homo sapiens (human)
protein bindingSomatostatin receptor type 4Homo sapiens (human)
somatostatin receptor activitySomatostatin receptor type 4Homo sapiens (human)
neuropeptide bindingSomatostatin receptor type 4Homo sapiens (human)
somatostatin receptor activitySomatostatin receptor type 3Homo sapiens (human)
signaling receptor bindingSomatostatin receptor type 3Homo sapiens (human)
protein bindingSomatostatin receptor type 3Homo sapiens (human)
neuropeptide bindingSomatostatin receptor type 3Homo sapiens (human)
G protein-coupled receptor activitySomatostatin receptor type 3Homo sapiens (human)
protein bindingSomatostatin receptor type 5Homo sapiens (human)
neuropeptide bindingSomatostatin receptor type 5Homo sapiens (human)
somatostatin receptor activitySomatostatin receptor type 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (6)

Processvia Protein(s)Taxonomy
plasma membraneSomatostatin receptor type 1Homo sapiens (human)
plasma membraneSomatostatin receptor type 1Homo sapiens (human)
neuron projectionSomatostatin receptor type 1Homo sapiens (human)
cytosolSomatostatin receptor type 2Homo sapiens (human)
plasma membraneSomatostatin receptor type 2Homo sapiens (human)
neuron projectionSomatostatin receptor type 2Homo sapiens (human)
plasma membraneSomatostatin receptor type 2Homo sapiens (human)
plasma membraneSomatostatin receptor type 4Homo sapiens (human)
neuron projectionSomatostatin receptor type 4Homo sapiens (human)
plasma membraneSomatostatin receptor type 4Homo sapiens (human)
plasma membraneSomatostatin receptor type 3Homo sapiens (human)
ciliumSomatostatin receptor type 3Homo sapiens (human)
ciliary membraneSomatostatin receptor type 3Homo sapiens (human)
non-motile ciliumSomatostatin receptor type 3Homo sapiens (human)
neuron projectionSomatostatin receptor type 3Homo sapiens (human)
plasma membraneSomatostatin receptor type 3Homo sapiens (human)
plasma membraneSomatostatin receptor type 5Homo sapiens (human)
plasma membraneSomatostatin receptor type 5Homo sapiens (human)
neuron projectionSomatostatin receptor type 5Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (23)

Assay IDTitleYearJournalArticle
AID203390Binding affinity towards human Somatostatin receptor type 1 (sst1) using Tyr11-[125I]-SRIF as radioligand was determined in CHO cells2003Journal of medicinal chemistry, Jun-05, Volume: 46, Issue:12
A novel somatostatin mimic with broad somatotropin release inhibitory factor receptor binding and superior therapeutic potential.
AID1204627Apparent permeability from apical to basolateral side in human Caco2 cells by LC-MS analysis2015European journal of medicinal chemistry, Jun-05, Volume: 97Exploring experimental and computational markers of cyclic peptides: Charting islands of permeability.
AID234075Selectivity for in vitro inhibitory activity (Ki) against human recombinant hsst3 and hsst2 receptors1998Journal of medicinal chemistry, Jul-16, Volume: 41, Issue:15
Design, synthesis, and biological activities of potent and selective somatostatin analogues incorporating novel peptoid residues.
AID1204626Apparent permeability of the compound at 50 uM after 5 hrs by PAMPA method2015European journal of medicinal chemistry, Jun-05, Volume: 97Exploring experimental and computational markers of cyclic peptides: Charting islands of permeability.
AID203083In vitro inhibition of radioligand binding to human somatostatin receptor (hsst2) expressed in CHO cells.1998Journal of medicinal chemistry, Jul-16, Volume: 41, Issue:15
Design, synthesis, and biological activities of potent and selective somatostatin analogues incorporating novel peptoid residues.
AID203579In vitro inhibition of radioligand binding to human Somatostatin receptor type 5 expressed in CCL-39 cells.1998Journal of medicinal chemistry, Jul-16, Volume: 41, Issue:15
Design, synthesis, and biological activities of potent and selective somatostatin analogues incorporating novel peptoid residues.
AID203077In vitro inhibition of radioligand binding to human somatostatin receptor (hsst1) expressed in hSF6 cells.1998Journal of medicinal chemistry, Jul-16, Volume: 41, Issue:15
Design, synthesis, and biological activities of potent and selective somatostatin analogues incorporating novel peptoid residues.
AID203551Binding affinity towards human Somatostatin receptor type 3 (sst3) using Tyr11-[125I]-SRIF as radioligand was determined in CHO cells2003Journal of medicinal chemistry, Jun-05, Volume: 46, Issue:12
A novel somatostatin mimic with broad somatotropin release inhibitory factor receptor binding and superior therapeutic potential.
AID203224In vitro inhibition of radioligand binding to human somatostatin receptor (hsst3) expressed in CHO cells.1998Journal of medicinal chemistry, Jul-16, Volume: 41, Issue:15
Design, synthesis, and biological activities of potent and selective somatostatin analogues incorporating novel peptoid residues.
AID234076Selectivity for in vitro inhibitory activity (Ki) against human recombinant hsst5 and hsst2 receptors1998Journal of medicinal chemistry, Jul-16, Volume: 41, Issue:15
Design, synthesis, and biological activities of potent and selective somatostatin analogues incorporating novel peptoid residues.
AID203409Binding affinity towards human Somatostatin receptor type 2 (sst2) using Tyr11-[125I]-SRIF as radioligand was determined in CHO cells2003Journal of medicinal chemistry, Jun-05, Volume: 46, Issue:12
A novel somatostatin mimic with broad somatotropin release inhibitory factor receptor binding and superior therapeutic potential.
AID203583In vitro inhibition of radioligand binding to human Somatostatin receptor type 5 expressed in CHO-K1 cells.1998Journal of medicinal chemistry, Jul-16, Volume: 41, Issue:15
Design, synthesis, and biological activities of potent and selective somatostatin analogues incorporating novel peptoid residues.
AID234074Selectivity for in vitro inhibitory activity (Kd) against human recombinant hsst5 and hsst2 receptors1998Journal of medicinal chemistry, Jul-16, Volume: 41, Issue:15
Design, synthesis, and biological activities of potent and selective somatostatin analogues incorporating novel peptoid residues.
AID203227In vitro inhibition of radioligand binding to human somatostatin receptor (hsst3) expressed in CHO-K1 cells.1998Journal of medicinal chemistry, Jul-16, Volume: 41, Issue:15
Design, synthesis, and biological activities of potent and selective somatostatin analogues incorporating novel peptoid residues.
AID234073Selectivity for in vitro inhibitory activity (Kd) against human recombinant hsst3 and hsst2 receptors1998Journal of medicinal chemistry, Jul-16, Volume: 41, Issue:15
Design, synthesis, and biological activities of potent and selective somatostatin analogues incorporating novel peptoid residues.
AID203234In vitro inhibition of radioligand binding to human somatostatin receptor (hsst4) expressed in CHO cells.1998Journal of medicinal chemistry, Jul-16, Volume: 41, Issue:15
Design, synthesis, and biological activities of potent and selective somatostatin analogues incorporating novel peptoid residues.
AID203088In vitro inhibition of radioligand binding to human somatostatin receptor (hsst2) expressed in CHO-K1 cells.1998Journal of medicinal chemistry, Jul-16, Volume: 41, Issue:15
Design, synthesis, and biological activities of potent and selective somatostatin analogues incorporating novel peptoid residues.
AID195175In vitro GH release inhibiting potency on anterior pitutaries from adult male rats, relative to somatostatin1995Journal of medicinal chemistry, May-26, Volume: 38, Issue:11
Three-dimensional quantitative structure-activity relationships of somatostatin analogues. 1. Comparative molecular field analysis of growth hormone release-inhibiting potencies.
AID247988Antiproliferative activity against human epidermiod carcinoma A431 cells2005Journal of medicinal chemistry, Apr-21, Volume: 48, Issue:8
Structure-activity relationship studies optimizing the antiproliferative activity of novel cyclic somatostatin analogues containing a restrained cyclic beta-amino acid.
AID203080In vitro inhibition of radioligand binding to human somatostatin receptor (hsst1) expressed in CHO-K1 cells.1998Journal of medicinal chemistry, Jul-16, Volume: 41, Issue:15
Design, synthesis, and biological activities of potent and selective somatostatin analogues incorporating novel peptoid residues.
AID203238In vitro inhibition of radioligand binding to human somatostatin receptor (hsst4) expressed in CHO-K1 cells.1998Journal of medicinal chemistry, Jul-16, Volume: 41, Issue:15
Design, synthesis, and biological activities of potent and selective somatostatin analogues incorporating novel peptoid residues.
AID203709Binding affinity towards human Somatostatin receptor type 5 (sst5) using Tyr11-[125I]-SRIF as radioligand was determined in COS cell2003Journal of medicinal chemistry, Jun-05, Volume: 46, Issue:12
A novel somatostatin mimic with broad somatotropin release inhibitory factor receptor binding and superior therapeutic potential.
AID203570Binding affinity towards human Somatostatin receptor type 4 (sst4) using Tyr11-[125I]-SRIF as radioligand was determined in CHO cells2003Journal of medicinal chemistry, Jun-05, Volume: 46, Issue:12
A novel somatostatin mimic with broad somatotropin release inhibitory factor receptor binding and superior therapeutic potential.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (5)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (40.00)18.2507
2000's2 (40.00)29.6817
2010's1 (20.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.58

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 Index12.58 (24.57)
Research Supply Index1.79 (2.92)
Research Growth Index4.37 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.58)

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%
Other5 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
atenolol
Atenolol: A cardioselective beta-1 adrenergic blocker possessing properties and potency similar to PROPRANOLOL, but without a negative inotropic effect.. atenolol : An ethanolamine compound having a (4-carbamoylmethylphenoxy)methyl group at the 1-position and an N-isopropyl substituent.		2.1110ethanolamines;
monocarboxylic acid amide;
propanolamine		anti-arrhythmia drug;
antihypertensive agent;
beta-adrenergic antagonist;
environmental contaminant;
sympatholytic agent;
xenobiotic
quinidine
Quinidine: An optical isomer of quinine, extracted from the bark of the CHINCHONA tree and similar plant species. This alkaloid dampens the excitability of cardiac and skeletal muscles by blocking sodium and potassium currents across cellular membranes. It prolongs cellular ACTION POTENTIALS, and decreases automaticity. Quinidine also blocks muscarinic and alpha-adrenergic neurotransmission.. quinidine : A cinchona alkaloid consisting of cinchonine with the hydrogen at the 6-position of the quinoline ring substituted by methoxy.		2.1110cinchona alkaloidalpha-adrenergic antagonist;
anti-arrhythmia drug;
antimalarial;
drug allergen;
EC 1.14.13.181 (13-deoxydaunorubicin hydroxylase) inhibitor;
EC 3.6.3.44 (xenobiotic-transporting ATPase) inhibitor;
muscarinic antagonist;
P450 inhibitor;
potassium channel blocker;
sodium channel blocker
seglitide
seglitide: more potent than somatostatin for inhibition of insulin, glucagon & growth hormone release; used experimentally in treatment of Alzheimer's disease; somatostatin receptor antagonist		2.420
lanreotide
[no description available]		2.420
pasireotide
pasireotide : A six-membered homodetic cyclic peptide composed from L-phenylglycyl, D-tryptophyl, L-lysyl, O-benzyl-L-tyrosyl, L-phenylalanyl and modified L-hydroxyproline residues joined in sequence. A somatostatin analogue with pharmacologic properties mimicking those of the natural hormone somatostatin; used (as its diaspartate salt) for treatment of Cushing's disease.		2.0110homodetic cyclic peptide;
peptide hormone		antineoplastic agent
bim 23052
[no description available]		1.9810
somatostatin
[no description available]		2.0110heterodetic cyclic peptide;
peptide hormone
bim 23056
[no description available]		1.9810
ConditionIndicatedRelationship StrengthStudiesTrials
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