Compounds > cyclo(d-tyrosyl-arginyl-arginyl-3-(2-naphthyl)alanyl-glycyl)
Page last updated: 2024-11-10

cyclo(d-tyrosyl-arginyl-arginyl-3-(2-naphthyl)alanyl-glycyl)

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

Cross-References

ID SourceID
PubMed CID5275843
CHEMBL ID436283
CHEMBL ID2180076
CHEBI ID183910
SCHEMBL ID15987252
MeSH IDM0481365

Synonyms (20)

Synonym
fc 131
fc-131
cyclo(-nal-gly-d-tyr-arg-arg-)
1-[3-[(2s,5s,8s,14r)-5-(3-guanidinopropyl)-14-[(4-hydroxyphenyl)methyl]-8-(2-naphthylmethyl)-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentazacyclopentadec-2-yl]propyl]guanidine
cyclo(-d-tyr-arg-arg-nal-gly-)
fc131
n-{3-[(2s,5s,8s,14r)-5-(3-guanidino-propyl)-14-(4-hydroxy-benzyl)-8-naphthalen-2-ylmethyl-3,6,9,12,15-pentaoxo-1,4,7,10,13pentaaza-cyclopentadec-2-yl]-propyl}-guanidine
bdbm50166106
CHEMBL436283 ,
2-[3-[(2s,5s,8s,14r)-5-[3-(diaminomethylideneamino)propyl]-14-[(4-hydroxyphenyl)methyl]-8-(naphthalen-2-ylmethyl)-3,6,9,12,15-pentaoxo-1,4,7,10,13-pentazacyclopentadec-2-yl]propyl]guanidine
CHEBI:183910
cyclo[3-(2-naphthalenyl)-l-alanylglycyl-d-tyrosyl-l-arginyl-l-arginyl]
CHEMBL2180076 ,
bdbm50399002
SCHEMBL15987252
606968-52-9
CS-0027759
HY-P1104
cyclo[2-nal-gly-d-tyr-arg-arg]
AKOS040745190
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
oligopeptideA peptide containing a relatively small number of amino acids.
[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 (4)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Adenosine receptor A2bRattus norvegicus (Norway rat)IC50 (µMol)0.12600.00240.68169.0000AID668820
Adenosine receptor A2aRattus norvegicus (Norway rat)IC50 (µMol)0.12600.00120.48289.0000AID668820
C-X-C chemokine receptor type 4Homo sapiens (human)IC50 (µMol)0.24290.00030.28766.2000AID1186325; AID1229746; AID242223; AID344154; AID662899; AID668820
[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)
Atypical chemokine receptor 3Homo sapiens (human)EC50 (µMol)2.19761.99532.19762.4000AID1229747
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (53)

Processvia Protein(s)Taxonomy
angiogenesisAtypical chemokine receptor 3Homo sapiens (human)
vasculogenesisAtypical chemokine receptor 3Homo sapiens (human)
cell adhesionAtypical chemokine receptor 3Homo sapiens (human)
negative regulation of cell population proliferationAtypical chemokine receptor 3Homo sapiens (human)
oculomotor nerve developmentAtypical chemokine receptor 3Homo sapiens (human)
receptor internalizationAtypical chemokine receptor 3Homo sapiens (human)
chemokine-mediated signaling pathwayAtypical chemokine receptor 3Homo sapiens (human)
positive regulation of ERK1 and ERK2 cascadeAtypical chemokine receptor 3Homo sapiens (human)
negative regulation of intrinsic apoptotic signaling pathway in response to DNA damageAtypical chemokine receptor 3Homo sapiens (human)
positive regulation of mesenchymal stem cell migrationAtypical chemokine receptor 3Homo sapiens (human)
cell chemotaxisAtypical chemokine receptor 3Homo sapiens (human)
calcium-mediated signalingAtypical chemokine receptor 3Homo sapiens (human)
immune responseAtypical chemokine receptor 3Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationAtypical chemokine receptor 3Homo sapiens (human)
calcium-mediated signalingC-X-C chemokine receptor type 4Homo sapiens (human)
response to hypoxiaC-X-C chemokine receptor type 4Homo sapiens (human)
neuron migrationC-X-C chemokine receptor type 4Homo sapiens (human)
epithelial cell developmentC-X-C chemokine receptor type 4Homo sapiens (human)
dendritic cell chemotaxisC-X-C chemokine receptor type 4Homo sapiens (human)
apoptotic processC-X-C chemokine receptor type 4Homo sapiens (human)
inflammatory responseC-X-C chemokine receptor type 4Homo sapiens (human)
G protein-coupled receptor signaling pathwayC-X-C chemokine receptor type 4Homo sapiens (human)
neuron recognitionC-X-C chemokine receptor type 4Homo sapiens (human)
response to virusC-X-C chemokine receptor type 4Homo sapiens (human)
response to activityC-X-C chemokine receptor type 4Homo sapiens (human)
telencephalon cell migrationC-X-C chemokine receptor type 4Homo sapiens (human)
regulation of cell adhesionC-X-C chemokine receptor type 4Homo sapiens (human)
positive regulation of cell migrationC-X-C chemokine receptor type 4Homo sapiens (human)
positive regulation of vascular wound healingC-X-C chemokine receptor type 4Homo sapiens (human)
CXCL12-activated CXCR4 signaling pathwayC-X-C chemokine receptor type 4Homo sapiens (human)
regulation of programmed cell deathC-X-C chemokine receptor type 4Homo sapiens (human)
myelin maintenanceC-X-C chemokine receptor type 4Homo sapiens (human)
endothelial cell differentiationC-X-C chemokine receptor type 4Homo sapiens (human)
symbiont entry into host cellC-X-C chemokine receptor type 4Homo sapiens (human)
positive regulation of oligodendrocyte differentiationC-X-C chemokine receptor type 4Homo sapiens (human)
regulation of viral processC-X-C chemokine receptor type 4Homo sapiens (human)
regulation of chemotaxisC-X-C chemokine receptor type 4Homo sapiens (human)
positive regulation of chemotaxisC-X-C chemokine receptor type 4Homo sapiens (human)
detection of temperature stimulus involved in sensory perception of painC-X-C chemokine receptor type 4Homo sapiens (human)
detection of mechanical stimulus involved in sensory perception of painC-X-C chemokine receptor type 4Homo sapiens (human)
regulation of calcium ion transportC-X-C chemokine receptor type 4Homo sapiens (human)
cardiac muscle contractionC-X-C chemokine receptor type 4Homo sapiens (human)
endothelial tube morphogenesisC-X-C chemokine receptor type 4Homo sapiens (human)
cellular response to cytokine stimulusC-X-C chemokine receptor type 4Homo sapiens (human)
cellular response to organonitrogen compoundC-X-C chemokine receptor type 4Homo sapiens (human)
cellular response to xenobiotic stimulusC-X-C chemokine receptor type 4Homo sapiens (human)
positive regulation of cold-induced thermogenesisC-X-C chemokine receptor type 4Homo sapiens (human)
response to tacrolimusC-X-C chemokine receptor type 4Homo sapiens (human)
positive regulation of dendrite extensionC-X-C chemokine receptor type 4Homo sapiens (human)
positive regulation of vasculature developmentC-X-C chemokine receptor type 4Homo sapiens (human)
positive regulation of mesenchymal stem cell migrationC-X-C chemokine receptor type 4Homo sapiens (human)
response to ultrasoundC-X-C chemokine receptor type 4Homo sapiens (human)
positive regulation of macrophage migration inhibitory factor signaling pathwayC-X-C chemokine receptor type 4Homo sapiens (human)
neurogenesisC-X-C chemokine receptor type 4Homo sapiens (human)
cell chemotaxisC-X-C chemokine receptor type 4Homo sapiens (human)
positive regulation of cytosolic calcium ion concentrationC-X-C chemokine receptor type 4Homo sapiens (human)
immune responseC-X-C chemokine receptor type 4Homo sapiens (human)
brain developmentC-X-C chemokine receptor type 4Homo sapiens (human)
calcium-mediated signalingC-X-C chemokine receptor type 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (16)

Processvia Protein(s)Taxonomy
scavenger receptor activityAtypical chemokine receptor 3Homo sapiens (human)
protein bindingAtypical chemokine receptor 3Homo sapiens (human)
coreceptor activityAtypical chemokine receptor 3Homo sapiens (human)
C-X-C chemokine receptor activityAtypical chemokine receptor 3Homo sapiens (human)
C-X-C chemokine bindingAtypical chemokine receptor 3Homo sapiens (human)
C-C chemokine receptor activityAtypical chemokine receptor 3Homo sapiens (human)
C-C chemokine bindingAtypical chemokine receptor 3Homo sapiens (human)
G protein-coupled adenosine receptor activityAdenosine receptor A2aRattus norvegicus (Norway rat)
virus receptor activityC-X-C chemokine receptor type 4Homo sapiens (human)
actin bindingC-X-C chemokine receptor type 4Homo sapiens (human)
G protein-coupled receptor activityC-X-C chemokine receptor type 4Homo sapiens (human)
protein bindingC-X-C chemokine receptor type 4Homo sapiens (human)
coreceptor activityC-X-C chemokine receptor type 4Homo sapiens (human)
C-X-C chemokine receptor activityC-X-C chemokine receptor type 4Homo sapiens (human)
C-C chemokine bindingC-X-C chemokine receptor type 4Homo sapiens (human)
ubiquitin protein ligase bindingC-X-C chemokine receptor type 4Homo sapiens (human)
myosin light chain bindingC-X-C chemokine receptor type 4Homo sapiens (human)
small molecule bindingC-X-C chemokine receptor type 4Homo sapiens (human)
C-X-C motif chemokine 12 receptor activityC-X-C chemokine receptor type 4Homo sapiens (human)
ubiquitin bindingC-X-C chemokine receptor type 4Homo sapiens (human)
C-C chemokine receptor activityC-X-C chemokine receptor type 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (17)

Processvia Protein(s)Taxonomy
endosomeAtypical chemokine receptor 3Homo sapiens (human)
early endosomeAtypical chemokine receptor 3Homo sapiens (human)
plasma membraneAtypical chemokine receptor 3Homo sapiens (human)
clathrin-coated pitAtypical chemokine receptor 3Homo sapiens (human)
cell surfaceAtypical chemokine receptor 3Homo sapiens (human)
intracellular membrane-bounded organelleAtypical chemokine receptor 3Homo sapiens (human)
recycling endosomeAtypical chemokine receptor 3Homo sapiens (human)
external side of plasma membraneAtypical chemokine receptor 3Homo sapiens (human)
Golgi membraneAdenosine receptor A2aRattus norvegicus (Norway rat)
lysosomeC-X-C chemokine receptor type 4Homo sapiens (human)
early endosomeC-X-C chemokine receptor type 4Homo sapiens (human)
cytoplasmC-X-C chemokine receptor type 4Homo sapiens (human)
lysosomeC-X-C chemokine receptor type 4Homo sapiens (human)
early endosomeC-X-C chemokine receptor type 4Homo sapiens (human)
late endosomeC-X-C chemokine receptor type 4Homo sapiens (human)
plasma membraneC-X-C chemokine receptor type 4Homo sapiens (human)
cell surfaceC-X-C chemokine receptor type 4Homo sapiens (human)
cell leading edgeC-X-C chemokine receptor type 4Homo sapiens (human)
cytoplasmic vesicleC-X-C chemokine receptor type 4Homo sapiens (human)
extracellular exosomeC-X-C chemokine receptor type 4Homo sapiens (human)
anchoring junctionC-X-C chemokine receptor type 4Homo sapiens (human)
protein-containing complexC-X-C chemokine receptor type 4Homo sapiens (human)
external side of plasma membraneC-X-C chemokine receptor type 4Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (14)

Assay IDTitleYearJournalArticle
AID242223Inhibition of [125I]SDF-1 binding to C-X-C chemokine receptor type 4 (CXCR4) expressed in CHO cells2005Journal of medicinal chemistry, May-05, Volume: 48, Issue:9
Identification of novel low molecular weight CXCR4 antagonists by structural tuning of cyclic tetrapeptide scaffolds.
AID1229747Agonist activity at CXCR7 (unknown origin) expressed in HEK293E cells co-transfected with receptor-eYFP construct and beta-arrestin2-Rluc assessed as induction of receptor-mediated beta-arrestin recruitment by BRET assay2015Journal of medicinal chemistry, Jul-09, Volume: 58, Issue:13
Development of novel CXC chemokine receptor 7 (CXCR7) ligands: selectivity switch from CXCR4 antagonists with a cyclic pentapeptide scaffold.
AID668822Antiviral activity against Human immunodeficiency virus 1 NL4.3 infected in human HeLa cells assessed as inhibition of viral replication after 48 hrs by MAGI assay2011ACS medicinal chemistry letters, Jun-09, Volume: 2, Issue:6
Potent CXCR4 antagonists containing amidine type Peptide bond isosteres.
AID662899Displacement of [125I]SDF-1alpha from CXCR4 expressed in HEK293 cell membrane after 1 hr2012Journal of medicinal chemistry, Mar-22, Volume: 55, Issue:6
Structure-activity relationship study of a CXC chemokine receptor type 4 antagonist, FC131, using a series of alkene dipeptide isosteres.
AID668824Antiviral activity against CCR5-tropic Human immunodeficiency virus 1 Ba-L infected in human HeLa cells assessed as inhibition of viral replication at 10 uM after 48 hrs by MAGI assay2011ACS medicinal chemistry letters, Jun-09, Volume: 2, Issue:6
Potent CXCR4 antagonists containing amidine type Peptide bond isosteres.
AID662535Cytotoxicity against human MT4 cells assessed as reduction of cell viability2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Pharmacophore-based small molecule CXCR4 ligands.
AID668823Antiviral activity against Human immunodeficiency virus 1 3B infected in human HeLa cells assessed as inhibition of viral replication after 48 hrs by MAGI assay2011ACS medicinal chemistry letters, Jun-09, Volume: 2, Issue:6
Potent CXCR4 antagonists containing amidine type Peptide bond isosteres.
AID1186325Inhibition of CXCR4 (unknown origin)2014Bioorganic & medicinal chemistry, Sep-01, Volume: 22, Issue:17
Design, synthesis, and biological evaluation of scaffold-based tripeptidomimetic antagonists for CXC chemokine receptor 4 (CXCR4).
AID344154Displacement of [125I]SDF1 from human CXCR4 expressed in CHO cells2008Bioorganic & medicinal chemistry letters, Jul-15, Volume: 18, Issue:14
Identification of novel non-peptide CXCR4 antagonists by ligand-based design approach.
AID1229746Inhibition of [125I]SDF-1alpha binding to CXCR4 (unknown origin) expressed in HEK293 cell membranes incubated for 1 hr by radioligand displacement assay2015Journal of medicinal chemistry, Jul-09, Volume: 58, Issue:13
Development of novel CXC chemokine receptor 7 (CXCR7) ligands: selectivity switch from CXCR4 antagonists with a cyclic pentapeptide scaffold.
AID662533Displacement of [125I]-CXCL12 from CXCR4 expressed in human Jurkat cells at 10 uM relative to T1402012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Pharmacophore-based small molecule CXCR4 ligands.
AID662534Antiviral activity against X4-tropic HIV1 NL4.3 infected in human MT4 cells assessed as protection from virus-induced cytopathogenicity2012Bioorganic & medicinal chemistry letters, Jun-15, Volume: 22, Issue:12
Pharmacophore-based small molecule CXCR4 ligands.
AID1229745Inhibition of [125I]SDF-1alpha binding to CXCR7 (unknown origin) expressed in CHO cell membranes incubated for 1 hr by radioligand displacement assay2015Journal of medicinal chemistry, Jul-09, Volume: 58, Issue:13
Development of novel CXC chemokine receptor 7 (CXCR7) ligands: selectivity switch from CXCR4 antagonists with a cyclic pentapeptide scaffold.
AID668820Displacement of [125I]-SDF-1alpha from CXCR4 receptor expressed in HEK293 cells after 1 hr by scintillation counting2011ACS medicinal chemistry letters, Jun-09, Volume: 2, Issue:6
Potent CXCR4 antagonists containing amidine type Peptide bond isosteres.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (7)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's0 (0.00)18.2507
2000's2 (28.57)29.6817
2010's5 (71.43)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: 12.75

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 Index12.75 (24.57)
Research Supply Index2.08 (2.92)
Research Growth Index4.83 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.75)

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%
Other7 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
zidovudine
Zidovudine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by an azido group. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is a potent inhibitor of HIV replication, acting as a chain-terminator of viral DNA during reverse transcription. It improves immunologic function, partially reverses the HIV-induced neurological dysfunction, and improves certain other clinical abnormalities associated with AIDS. Its principal toxic effect is dose-dependent suppression of bone marrow, resulting in anemia and leukopenia.. zidovudine : A pyrimidine 2',3'-dideoxyribonucleoside compound having a 3'-azido substituent and thymine as the nucleobase.		2.0710azide;
pyrimidine 2',3'-dideoxyribonucleoside		antimetabolite;
antiviral drug;
HIV-1 reverse transcriptase inhibitor
krh 1636
KRH 1636: structure in first source		2.0710
vicriviroc
vicriviroc: structure in first source		2.0710(trifluoromethyl)benzenes
ConditionIndicatedRelationship StrengthStudiesTrials