Page last updated: 2024-11-08

cyclo(l-phe-l-pro)

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 CID443440
CHEMBL ID512845
CHEBI ID69440
SCHEMBL ID2019443
MeSH IDM0439767

Synonyms (32)

Synonym
KUC100417N
MLS001208545
smr000504521
inchi=1/c14h16n2o2/c17-13-12-7-4-8-16(12)14(18)11(15-13)9-10-5-2-1-3-6-10/h1-3,5-6,11-12h,4,7-9h2,(h,15,17)/t11-,12-/m0/s
pyrrolo[1,2-a]pyrazine-1,4-dione, hexahydro-3-(phenylmethyl)-, (3s,8as)-
rel-(3r,8ar)-3-benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
diketopiperazine cyclo(d-pro-d-phe)
3-benzyl-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione
(3s,8as)-3-benzyl-hexahydro-pyrrolo[1,2-a]pyrazine-1,4-dione
3705-26-8
cyclo(l-phe-l-pro)
(3s-trans)-3-benzylhexahydropyrrolo(1,2-a)pyrazine-1,4-dione
AKOS000739487
(3s,8as)-3-benzyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
chebi:69440 ,
CHEMBL512845
HMS2843P17
cyclo(-phe-pro)
SCHEMBL2019443
cyclo-l-phenylalanyl-l-proline
cyclo l-pro-l-phe (fr. 2-2)
bdbm163710
(3s,8as)-3-benzylhexahydropyrrolo[1,2-a]pyrazine-1,4-dione
mfcd00038604
cyclo(pro-phe)
cyclo(l-phenylalanyl-l-prolyl)
(3s,8ar)-3-benzyl-2,3,6,7,8,8a-hexahydropyrrolo[1,2-a]pyrazine-1,4-dione
Q27104973
EX-A3331
AC6021
AS-56632
DTXSID101316106
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
metaboliteAny intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
[role 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]

Drug Classes (1)

ClassDescription
organic molecular entityAny molecular entity that contains carbon.
[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 (3)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Beta-lactamaseEscherichia coli K-12Potency112.20200.044717.8581100.0000AID485294
DNA polymerase iota isoform a (long)Homo sapiens (human)Potency89.12510.050127.073689.1251AID588590
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Dihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)IC50 (µMol)50.00000.00050.742710.0000AID1801348
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (4)

Processvia Protein(s)Taxonomy
UDP biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
'de novo' UMP biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
pyrimidine ribonucleotide biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
'de novo' pyrimidine nucleobase biosynthetic processDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
dihydroorotase activityDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
protein bindingDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
dihydroorotate dehydrogenase (quinone) activityDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
dihydroorotate dehydrogenase activityDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
nucleoplasmDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
mitochondrionDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
mitochondrial inner membraneDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
cytosolDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
mitochondrial inner membraneDihydroorotate dehydrogenase (quinone), mitochondrialHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (37)

Assay IDTitleYearJournalArticle
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588497High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain F protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID1745845Primary qHTS for Inhibitors of ATXN expression
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID651635Viability Counterscreen for Primary qHTS for Inhibitors of ATXN expression
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588501High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Lethal Factor Protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Current protocols in cytometry, Oct, Volume: Chapter 13Microsphere-based flow cytometry protease assays for use in protease activity detection and high-throughput screening.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2006Cytometry. Part A : the journal of the International Society for Analytical Cytology, May, Volume: 69, Issue:5
Microsphere-based protease assays and screening application for lethal factor and factor Xa.
AID588499High-throughput multiplex microsphere screening for inhibitors of toxin protease, specifically Botulinum neurotoxin light chain A protease, MLPCN compound set2010Assay and drug development technologies, Feb, Volume: 8, Issue:1
High-throughput multiplex flow cytometry screening for botulinum neurotoxin type a light chain protease inhibitors.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1265327Inhibition of LPS-induced IL-6 mRNA level in mouse RAW264.7 cells in presence of 1 ug/ml LPS for 6 hrs by qRT-PCR analysis2015Bioorganic & medicinal chemistry letters, Dec-15, Volume: 25, Issue:24
Attenuation of TNF-α secretion by L-proline-based cyclic dipeptides produced by culture broth of Pseudomonas aeruginosa.
AID1238342Antibacterial activity against Escherichia coli ATCC 25922 after 18 hrs by agar diffusion method2015Bioorganic & medicinal chemistry letters, Aug-15, Volume: 25, Issue:16
Antibacterial activity of diketopiperazines isolated from a marine fungus using t-butoxycarbonyl group as a simple tool for purification.
AID1265333Inhibition of LPS-induced TNF-alpha mRNA level in mouse RAW264.7 cells in presence of 1 ug/ml LPS for 6 hrs by qRT-PCR analysis2015Bioorganic & medicinal chemistry letters, Dec-15, Volume: 25, Issue:24
Attenuation of TNF-α secretion by L-proline-based cyclic dipeptides produced by culture broth of Pseudomonas aeruginosa.
AID616299Anti-inflammatory activity in human neutrophils assessed as inhibition of FMLP/CB-induced superoxide anion generation2011Journal of natural products, Sep-23, Volume: 74, Issue:9
Anti-inflammatory principles from Cordyceps sinensis.
AID1265326Cytotoxicity against mouse RAW264.7 cells assessed as decrease in cell viability pretreated at 50 uM for 1 hr followed by addition of LPS incubated for 24 hrs by MTT assay2015Bioorganic & medicinal chemistry letters, Dec-15, Volume: 25, Issue:24
Attenuation of TNF-α secretion by L-proline-based cyclic dipeptides produced by culture broth of Pseudomonas aeruginosa.
AID332429Displacement of [3H]substance P from NK1 receptor in human astrocytoma cells at 200 uM1994Journal of natural products, Apr, Volume: 57, Issue:4
Spiroquinazoline, a novel substance P inhibitor with a new carbon skeleton, isolated from Aspergillus flavipes.
AID659561Induction of TNF-alpha secretion in mouse J774A1 cells at 5 ug/mL after 48 hrs by ELISA relative to control2012Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9
The effects of diketopiperazines from Callyspongia sp. on release of cytokines and chemokines in cultured J774A.1 macrophages.
AID1779410Antibacterial activity against Staphylococcus aureus ATCC 29213 assessed as bacterial growth inhibition at 50 ug/disk measured after 24 to 72 hrs by disk diffusion assay2021Journal of natural products, 07-23, Volume: 84, Issue:7
Broomeanamides: Cyclic Octapeptides from an Isolate of the Fungicolous Ascomycete
AID1265334Toxicity in mouse RAW264.7 cells assessed as effect on NO production by Griess method2015Bioorganic & medicinal chemistry letters, Dec-15, Volume: 25, Issue:24
Attenuation of TNF-α secretion by L-proline-based cyclic dipeptides produced by culture broth of Pseudomonas aeruginosa.
AID1779411Antifungal activity against Candida albicans ATCC10231 assessed as fungal growth inhibition at 50 ug/disk measured after 24 to 72 hrs by disk diffusion assay2021Journal of natural products, 07-23, Volume: 84, Issue:7
Broomeanamides: Cyclic Octapeptides from an Isolate of the Fungicolous Ascomycete
AID1238341Antibacterial activity against Bacillus subtilis NCTC 2116 after 18 hrs by agar diffusion method2015Bioorganic & medicinal chemistry letters, Aug-15, Volume: 25, Issue:16
Antibacterial activity of diketopiperazines isolated from a marine fungus using t-butoxycarbonyl group as a simple tool for purification.
AID616386Antioxidant activity assessed DPPH scavenging activity at 500 uM2011Journal of natural products, Sep-23, Volume: 74, Issue:9
Anti-inflammatory principles from Cordyceps sinensis.
AID616383Anti-inflammatory activity in human neutrophils assessed as inhibition of FMLP/CB-induced elastase release2011Journal of natural products, Sep-23, Volume: 74, Issue:9
Anti-inflammatory principles from Cordyceps sinensis.
AID659559Induction of IFN-gamma secretion in mouse J774A1 cells at 5 ug/mL after 48 hrs by ELISA relative to control2012Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9
The effects of diketopiperazines from Callyspongia sp. on release of cytokines and chemokines in cultured J774A.1 macrophages.
AID1265335Toxicity in mouse RAW264.7 cells assessed as effect on TNF-alpha mRNA level by qRT-PCR analysis2015Bioorganic & medicinal chemistry letters, Dec-15, Volume: 25, Issue:24
Attenuation of TNF-α secretion by L-proline-based cyclic dipeptides produced by culture broth of Pseudomonas aeruginosa.
AID659558Induction of IL10 secretion in mouse J774A1 cells at 5 ug/mL after 48 hrs by ELISA relative to control2012Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9
The effects of diketopiperazines from Callyspongia sp. on release of cytokines and chemokines in cultured J774A.1 macrophages.
AID400687Antibacterial activity against Micrococcus luteus after 2 days by disk assay1996Journal of natural products, Mar, Volume: 59, Issue:3
Metabolites from an Antarctic sponge-associated bacterium, Pseudomonas aeruginosa.
AID400686Antibacterial activity against Bacillus cereus after 2 days by disk assay1996Journal of natural products, Mar, Volume: 59, Issue:3
Metabolites from an Antarctic sponge-associated bacterium, Pseudomonas aeruginosa.
AID1265328Inhibition of LPS-induced IL-1beta mRNA level in mouse RAW264.7 cells in presence of 1 ug/ml LPS for 6 hrs by qRT-PCR analysis2015Bioorganic & medicinal chemistry letters, Dec-15, Volume: 25, Issue:24
Attenuation of TNF-α secretion by L-proline-based cyclic dipeptides produced by culture broth of Pseudomonas aeruginosa.
AID400688Antibacterial activity against Staphylococcus aureus after 2 days by disk assay1996Journal of natural products, Mar, Volume: 59, Issue:3
Metabolites from an Antarctic sponge-associated bacterium, Pseudomonas aeruginosa.
AID659560Induction of MCP-1 secretion in mouse J774A1 cells at 5 ug/mL after 48 hrs by ELISA relative to control2012Bioorganic & medicinal chemistry letters, May-01, Volume: 22, Issue:9
The effects of diketopiperazines from Callyspongia sp. on release of cytokines and chemokines in cultured J774A.1 macrophages.
AID1265336Inhibition of LPS-induced TNF-alpha production in mouse RAW264.7 cells pretreated with compound at 100 uM for 1 hr followed by addition of 1 ug/ml LPS for 6 hrs by ELISA2015Bioorganic & medicinal chemistry letters, Dec-15, Volume: 25, Issue:24
Attenuation of TNF-α secretion by L-proline-based cyclic dipeptides produced by culture broth of Pseudomonas aeruginosa.
AID1238340Antibacterial activity against Staphylococcus aureus ATCC 25923 after 18 hrs by agar diffusion method2015Bioorganic & medicinal chemistry letters, Aug-15, Volume: 25, Issue:16
Antibacterial activity of diketopiperazines isolated from a marine fungus using t-butoxycarbonyl group as a simple tool for purification.
AID1801348DCIP-linked Assay from Article 10.1111/cbdd.12530: \\Novel Diketopiperazine Dihydroorotate Dehydrogenase Inhibitors Purified from Traditional Tibetan Animal Medicine Osteon Myospalacem Baileyi.\\2015Chemical biology & drug design, Oct, Volume: 86, Issue:4
Novel Diketopiperazine Dihydroorotate Dehydrogenase Inhibitors Purified from Traditional Tibetan Animal Medicine Osteon Myospalacem Baileyi.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (13)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's2 (15.38)18.2507
2000's1 (7.69)29.6817
2010's8 (61.54)24.3611
2020's2 (15.38)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.13

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 Index12.13 (24.57)
Research Supply Index2.64 (2.92)
Research Growth Index4.77 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.13)

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]