Compounds > cyclo(phenylalanyl-phenylalanyl)
Page last updated: 2024-12-07

cyclo(phenylalanyl-phenylalanyl)

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

Description

cyclo(L-phenylalanyl-L-phenylalanyl) : A member of the class of 2,5-diketopiperazines that is piperazine-2,5-dione in which one hydrogen at position 3 and one hydrogen at position 6 are replaced by benzyl groups (the 3S,6S-diastereomer). [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]

Cross-References

ID SourceID
PubMed CID76116
CHEMBL ID126124
CHEBI ID71610
SCHEMBL ID1405670
MeSH IDM0194170

Synonyms (25)

Synonym
cyclo(phe-phe)
2,5-piperazinedione, 3,6-bis(phenylmethyl)-, (3s-cis)-
2862-51-3
cyclo(-phe-phe)
cyclo(phenylalanyl-phenylalanyl)
cyclo(l-phe-l-phe)
CHEMBL126124 ,
chebi:71610 ,
(3s,6s)-3,6-dibenzylpiperazine-2,5-dione
2,5-piperazinedione, 3,6-bis(phenylmethyl)-, (3s,6s)-
cyclo(l-phenylalanyl-l-phenylalanyl)
(3s,6z)-3,6-dibenzylpiperazine-2,5-dione
SCHEMBL1405670
DTXSID00182799
AKOS028113012
JUAPMRSLDANLAS-HOTGVXAUSA-N
(3s,6s)-3,6-bis(phenylmethyl)piperazine-2,5-dione
(3s,6s)-3,6-bis(phenylmethyl)-piperazine-2,5-dione
bdbm50505726
J-017161
mfcd00190985
Q27139753
E78058
CS-0661771
HY-W549438
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
2,5-diketopiperazinesAny piperazinone that has a piperazine-2,5-dione skeleton.
[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)

Activation Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Cytochrome P450 Mycobacterium tuberculosisKd2.40002.40002.40002.4000AID1526909
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (26)

Assay IDTitleYearJournalArticle
AID1543348Growth inhibition of Listeria monocytogenes WSLC 1001 incubated for 24 hrs under aerobic condition by microdilution method2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens.
AID1526909Binding affinity to Mycobacterium tuberculosis CYP121 expressed in Escherichia coli HMS174 (DE3) by UV-visible scanning spectrophotometric analysis2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Structure-Activity Relationships of
AID492016Cytotoxicity against human Bel7402 cells2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Thiodiketopiperazines produced by the endophytic fungus Epicoccum nigrum.
AID19254Partition coefficient of compound was measured in heptane/water system1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
Solvent-dependent conformation and hydrogen-bonding capacity of cyclosporin A: evidence from partition coefficients and molecular dynamics simulations.
AID1526914Binding affinity to Mycobacterium tuberculosis CYP121 expressed in Escherichia coli HMS174 (DE3) assessed as compound-adduct formation by measuring high spin complex at 0.5 to 2 mM incubated for 20 mins by EPR Spectroscopic method (Rvb = 0%)2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Structure-Activity Relationships of
AID1543336Antibiofilm activity against Porphyromonas gingivalis ATCC 33277 assessed as inhibition of biofilm formation up to 96 ug/mL after 24 hrs by crystal violet staining based assay2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens.
AID492017Cytotoxicity against human BGC823 cells2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Thiodiketopiperazines produced by the endophytic fungus Epicoccum nigrum.
AID717065Antimalarial activity against schizonts of chloroquine-sensitive Plasmodium berghei ANKA 2.34 after 16 hrs2012Bioorganic & medicinal chemistry letters, Dec-01, Volume: 22, Issue:23
Linear and cyclic dipeptides with antimalarial activity.
AID492019Cytotoxicity against human A2780 cells2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Thiodiketopiperazines produced by the endophytic fungus Epicoccum nigrum.
AID1543350Growth inhibition of Pseudomonas aeruginosa ATCC 10145 incubated for 24 hrs under aerobic condition by microdilution method2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens.
AID1543354Antibiofilm activity against Streptococcus mutans ATCC 25175 assessed as inhibition of biofilm formation up to 96 ug/mL after 24 hrs by crystal violet staining-based assay2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens.
AID1543335Antibiofilm activity against Fusobacterium nucleatum ATCC 25586 assessed as inhibition of biofilm formation up to 96 ug/mL after 24 hrs by crystal violet staining based assay2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens.
AID492015Cytotoxicity against human HCT116 cells2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Thiodiketopiperazines produced by the endophytic fungus Epicoccum nigrum.
AID492018Cytotoxicity against human A549 cells2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Thiodiketopiperazines produced by the endophytic fungus Epicoccum nigrum.
AID1543351Growth inhibition of Escherichia coli ATCC 15939 incubated for 24 hrs under aerobic condition by microdilution method2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens.
AID1526916Antimycobacterial activity against Mycobacterium tuberculosis H37Rv assessed as reduction in bacterial growth after 7 days by resazurin based fluorescence assay2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Structure-Activity Relationships of
AID717064Antimalarial activity against schizonts of chloroquine-sensitive Plasmodium berghei ANKA 2.34 assessed as chemosuppression of schizont numbers at 200 uM after 16 hrs relative to control2012Bioorganic & medicinal chemistry letters, Dec-01, Volume: 22, Issue:23
Linear and cyclic dipeptides with antimalarial activity.
AID1543364Inhibition of planktonic growth of Streptococcus mutans ATCC 25175 up to 96 ug/mL after 24 hrs relative to control2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens.
AID1543342Antibiofilm activity against Lactobacillus fermentum LacB1 assessed as inhibition of biofilm formation up to 96 ug/mL after 24 hrs by crystal violet staining based assay2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens.
AID492014Cytotoxicity against human HCT8 cells2010Journal of natural products, Jul-23, Volume: 73, Issue:7
Thiodiketopiperazines produced by the endophytic fungus Epicoccum nigrum.
AID243890Percent inhibition of human calpain 1 at 280 uM; Inhibition within 110%2005Bioorganic & medicinal chemistry letters, Jun-15, Volume: 15, Issue:12
Synthesis of a small library of diketopiperazines as potential inhibitors of calpain.
AID15680Partition coefficient (logP)1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
Solvent-dependent conformation and hydrogen-bonding capacity of cyclosporin A: evidence from partition coefficients and molecular dynamics simulations.
AID1526911Stability in Mycobacterium tuberculosis assessed as CYP121-catalyzed turnover2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Structure-Activity Relationships of
AID1526912Binding affinity to Mycobacterium tuberculosis Mycobacterium tuberculosis CYP121 expressed in Escherichia coli HMS174 (DE3) assessed as compound-adduct formation by measuring high spin complex by UV-visible scanning spectrophotometric analysis relative to2019Journal of medicinal chemistry, 11-14, Volume: 62, Issue:21
Structure-Activity Relationships of
AID19255Partition coefficient (logP)1993Journal of medicinal chemistry, Nov-26, Volume: 36, Issue:24
Solvent-dependent conformation and hydrogen-bonding capacity of cyclosporin A: evidence from partition coefficients and molecular dynamics simulations.
AID1543349Growth inhibition of Staphylococcus aureus ATCC 6538 incubated for 24 hrs under aerobic condition by microdilution method2019Bioorganic & medicinal chemistry, 06-15, Volume: 27, Issue:12
Anti-biofilm and anti-adherence properties of novel cyclic dipeptides against oral pathogens.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (8)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (25.00)18.2507
2000's1 (12.50)29.6817
2010's5 (62.50)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: 12.54

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 Index12.54 (24.57)
Research Supply Index2.20 (2.92)
Research Growth Index4.73 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.54)

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%
Other8 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
hydrogen
Hydrogen: The first chemical element in the periodic table with atomic symbol H, and atomic number 1. Protium (atomic weight 1) is by far the most common hydrogen isotope. Hydrogen also exists as the stable isotope DEUTERIUM (atomic weight 2) and the radioactive isotope TRITIUM (atomic weight 3). Hydrogen forms into a diatomic molecule at room temperature and appears as a highly flammable colorless and odorless gas.. dihydrogen : An elemental molecule consisting of two hydrogens joined by a single bond.		1.9710elemental hydrogen;
elemental molecule;
gas molecular entity		antioxidant;
electron donor;
food packaging gas;
fuel;
human metabolite
acetanilide
acetanilide: a phenylacetamide; use ACETANILIDES for the plural group meaning of the singular term. N-phenylacetamide : A member of the class of acetamides that is acetamide in which one of the hydrogens attached to the nitrogen is substituted by a phenyl group.		1.9810acetamides;
anilide		analgesic
4-nitrophenol
4-nitrophenol: RN given refers to parent cpd. mononitrophenol : A nitrophenol that is phenol carrying a single nitro substituent at unspecified position.. 4-nitrophenol : A member of the class of 4-nitrophenols that is phenol in which the hydrogen that is para to the hydroxy group has been replaced by a nitro group.		1.98104-nitrophenolshuman xenobiotic metabolite;
mouse metabolite
phenol
[no description available]		1.9810phenolsantiseptic drug;
disinfectant;
human xenobiotic metabolite;
mouse metabolite
benzamide
benzamide : An aromatic amide that consists of benzene bearing a single carboxamido substituent. The parent of the class of benzamides.		1.9810benzamides
chloroquine
Chloroquine: The prototypical antimalarial agent with a mechanism that is not well understood. It has also been used to treat rheumatoid arthritis, systemic lupus erythematosus, and in the systemic therapy of amebic liver abscesses.. chloroquine : An aminoquinoline that is quinoline which is substituted at position 4 by a [5-(diethylamino)pentan-2-yl]amino group at at position 7 by chlorine. It is used for the treatment of malaria, hepatic amoebiasis, lupus erythematosus, light-sensitive skin eruptions, and rheumatoid arthritis.		2.0710aminoquinoline;
organochlorine compound;
secondary amino compound;
tertiary amino compound		anticoronaviral agent;
antimalarial;
antirheumatic drug;
autophagy inhibitor;
dermatologic drug
2-nitrophenol
nitrophenol : Any member of the class of phenols or substituted phenols carrying at least 1 nitro group.		1.98102-nitrophenols
4-fluorobenzamide
4-fluorobenzamide: structure in first source		1.9810
histidylglycine
histidylglycine: RN given refers to all (L)-isomer. His-Gly : A dipeptide formed from L-histidine and glycine residues.		2.0710dipeptidemetabolite
cyclo(alanylalanyl)
[no description available]		2.2110
cyclo(tyrosyl-prolyl)
cyclo(tyrosyl-prolyl): structure in first source		2.0710organonitrogen compound;
organooxygen compound
cyclo(prolylprolyl)
cyclo(prolylprolyl): structure in first source		2.2110
cyclo(l-leucyl-l-tryptophyl)
cyclo(L-leucyl-L-tryptophyl): structure in first source		2.0210
cyclosporine
ramihyphin A: one of the metabolites produced by Fusarium sp. S-435; RN given refers to cpd with unknown MF		1.9810homodetic cyclic peptideanti-asthmatic drug;
anticoronaviral agent;
antifungal agent;
antirheumatic drug;
carcinogenic agent;
dermatologic drug;
EC 3.1.3.16 (phosphoprotein phosphatase) inhibitor;
geroprotector;
immunosuppressive agent;
metabolite
ginkgolide b
[no description available]		2.0510
cyclo(leucyl-prolyl)
cyclo(leucyl-prolyl): structure in first source. cyclo(L-Leu-L-Pro) : A homodetic cyclic peptide composed from leucyl and prolyl residues.		2.2110dipeptide;
homodetic cyclic peptide;
pyrrolopyrazine		bacterial metabolite;
marine metabolite
cyclo(leucyl-phenylalanyl)
cyclo(leucyl-phenylalanyl): has pronuclear fusion inhibitory activity; isolated from Streptomyces albulus; structure in first source. cyclo(L-phenylalanyl-L-leucyl) : A member of the class of 2,5-diketopiperazines that is piperazine-2,5-dione in which one hydrogen at position 3 and one hydrogen at position 6 are replaced by benzyl and isobutyl groups (the 3S,6S-diastereomer).		2.48202,5-diketopiperazinesmetabolite
(11S,14S)-Cyclo-(L-Trp-L-Phe)
[no description available]		2.0210indolesAspergillus metabolite
pd 150606
PD 150606: a calpain inhibitor; structure given in first source. (Z)-3-(4-iodophenyl)-2-mercaptoacrylic acid : An organoiodine compound that is acrylic acid in which the vinylic hydrogens at positions 2 and 3 are replaced by mercapto and 4-iodophenyl groups respectively (the Z geoisomer).		2.0210cinnamic acids;
organoiodine compound;
thioenol		apoptosis inhibitor;
calpain inhibitor
phevalin
phevalin: isolated from a Streptomyces sp.; structure given in first source. phevalin : A member of the class of pyrazinones that is pyrazin-2(1H)-one substituted by an isopropyl and benzyl groups at position 3 and 6, respectively. It is a natural product found in Staphylococcus aureus that inhibits calpain in a casein hydrolysis assay (IC50 = 1.3 muM), contributes to S. aureus infection in mice, and alters human keratinocyte gene expression.		2.0210benzenes;
pyrazinone		bacterial metabolite;
calpain inhibitor
calpain inhibitor iii
calpain inhibitor III: potential anticataract drug		2.0210
cyclo(tyrosyl-tyrosyl)
cyclo(L-tyrosyl-L-tyrosyl) : A cyclo(tyrosyl-tyrosyl) in which both stereocentres have L-configuration. Synthesized by Mycobacterium tuberculosis.		2.7930cyclo(tyrosyl-tyrosyl)metabolite
mycocyclosin
mycocyclosin: a secondary metabolite produced by Mycobacterium tuberculosis; structure in first source. mycocyclosin : An organic heterotetracyclic compound obtained via intramolecular oxidative aromatic coupling of cyclo(L-tyrosyl-L-tyrosyl).		2.21102,5-diketopiperazines;
organic heterotetracyclic compound;
polyphenol		metabolite
ConditionIndicatedRelationship StrengthStudiesTrials