Compounds > phevalin
Page last updated: 2024-11-12

phevalin

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

Description

phevalin: isolated from a Streptomyces sp.; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

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. [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 CID10376483
CHEMBL ID419498
CHEBI ID167320
SCHEMBL ID16431626
SCHEMBL ID21333942
MeSH IDM0255012

Synonyms (21)

Synonym
6-benzyl-3-propan-2-yl-1h-pyrazin-2-one
CHEMBL419498 ,
6-benzyl-3-isopropyl-1h-pyrazin-2-one
phevalin
6-benzyl-3-(propan-2-yl)pyrazin-2(1h)-one
aureusimine b
170713-71-0
6-benzyl-3-(propan-2-yl)-1,2-dihydropyrazin-2-one
CHEBI:167320
bdbm50104646
6-benzyl-3-isopropyl-2(1h)-pyrazinone
SCHEMBL16431626
mfcd00930483
6-benzyl-3-isopropylpyrazin-2-one
AKOS027325863
J-010645
6-benzyl-3-isopropylpyrazin-2(1h)-one
SCHEMBL21333942
EN300-107994
CS-0065625
HY-116486
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (2)

RoleDescription
bacterial metaboliteAny prokaryotic metabolite produced during a metabolic reaction in bacteria.
calpain inhibitorAn EC 3.4.22.* (cysteine endopeptidase) inhibitor that interferes with the action of any calpain.
[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 (2)

ClassDescription
benzenesAny benzenoid aromatic compound consisting of the benzene skeleton and its substituted derivatives.
pyrazinoneAny pyrazine carrying one or more oxo substituents.
[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)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Calpain-1 catalytic subunitHomo sapiens (human)IC50 (µMol)1.20000.00021.059210.0000AID46332
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Processvia Protein(s)Taxonomy
proteolysisCalpain-1 catalytic subunitHomo sapiens (human)
positive regulation of cell population proliferationCalpain-1 catalytic subunitHomo sapiens (human)
regulation of macroautophagyCalpain-1 catalytic subunitHomo sapiens (human)
receptor catabolic processCalpain-1 catalytic subunitHomo sapiens (human)
regulation of catalytic activityCalpain-1 catalytic subunitHomo sapiens (human)
mammary gland involutionCalpain-1 catalytic subunitHomo sapiens (human)
self proteolysisCalpain-1 catalytic subunitHomo sapiens (human)
regulation of NMDA receptor activityCalpain-1 catalytic subunitHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
calcium-dependent cysteine-type endopeptidase activityCalpain-1 catalytic subunitHomo sapiens (human)
calcium ion bindingCalpain-1 catalytic subunitHomo sapiens (human)
protein bindingCalpain-1 catalytic subunitHomo sapiens (human)
peptidase activityCalpain-1 catalytic subunitHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Processvia Protein(s)Taxonomy
cornified envelopeCalpain-1 catalytic subunitHomo sapiens (human)
extracellular regionCalpain-1 catalytic subunitHomo sapiens (human)
mitochondrionCalpain-1 catalytic subunitHomo sapiens (human)
lysosomeCalpain-1 catalytic subunitHomo sapiens (human)
cytosolCalpain-1 catalytic subunitHomo sapiens (human)
plasma membraneCalpain-1 catalytic subunitHomo sapiens (human)
focal adhesionCalpain-1 catalytic subunitHomo sapiens (human)
membraneCalpain-1 catalytic subunitHomo sapiens (human)
extracellular exosomeCalpain-1 catalytic subunitHomo sapiens (human)
calpain complexCalpain-1 catalytic subunitHomo sapiens (human)
ficolin-1-rich granule lumenCalpain-1 catalytic subunitHomo sapiens (human)
cytoplasmCalpain-1 catalytic subunitHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (3)

Assay IDTitleYearJournalArticle
AID240485Concentration required for inhibition of calpain2005Bioorganic & medicinal chemistry letters, Jun-15, Volume: 15, Issue:12
Synthesis of a small library of diketopiperazines as potential inhibitors of calpain.
AID243896Percent inhibition of human calpain 1 at 550 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.
AID46332Compound was tested for its inhibitory activity against calpain isolated from Streptomyces species2001Bioorganic & medicinal chemistry letters, Oct-08, Volume: 11, Issue:19
Synthesis of a reported calpain inhibitor isolated from Streptomyces griseus.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (10)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (10.00)18.2507
2000's2 (20.00)29.6817
2010's6 (60.00)24.3611
2020's1 (10.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 17.75

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 moderate demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index17.75 (24.57)
Research Supply Index2.40 (2.92)
Research Growth Index4.96 (4.65)
Search Engine Demand Index10.37 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (17.75)

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%
Other10 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
pyrazines
Pyrazines: A heterocyclic aromatic organic compound with the chemical formula C4H4N2.. pyrazine : A diazine that is benzene in which the carbon atoms at positions 1 and 4 have been replaced by nitrogen atoms.		3.6790diazine;
pyrazines		Daphnia magna metabolite
cyclo(phenylalanyl-phenylalanyl)
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).		2.02102,5-diketopiperazines
isopropyl thiogalactoside
Isopropyl Thiogalactoside: A non-metabolizable galactose analog that induces expression of the LAC OPERON.. isopropyl beta-D-thiogalactopyranoside : An S-glycosyl compound consisting of beta-D-1-thiogalactose having an isopropyl group attached to the anomeric sulfur.		2.0810S-glycosyl compound
cyclo(l-leucyl-l-tryptophyl)
cyclo(L-leucyl-L-tryptophyl): structure in first source		2.0210
alpha-chymotrypsin
Chymotrypsin: A serine endopeptidase secreted by the pancreas as its zymogen, CHYMOTRYPSINOGEN and carried in the pancreatic juice to the duodenum where it is activated by TRYPSIN. It selectively cleaves aromatic amino acids on the carboxyl side.		2.1510
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).		2.02102,5-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
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.		2.0210cyclo(tyrosyl-tyrosyl)metabolite
calpain
Calpain: Cysteine proteinase found in many tissues. Hydrolyzes a variety of endogenous proteins including NEUROPEPTIDES; CYTOSKELETAL PROTEINS; proteins from SMOOTH MUSCLE; CARDIAC MUSCLE; liver; platelets; and erythrocytes. Two subclasses having high and low calcium sensitivity are known. Removes Z-discs and M-lines from myofibrils. Activates phosphorylase kinase and cyclic nucleotide-independent protein kinase. This enzyme was formerly listed as EC 3.4.22.4.		7.4120
ConditionIndicatedRelationship StrengthStudiesTrials
Extravascular Hemolysis
[description not available]		02.0510
Infections, Staphylococcal
[description not available]		02.0510
Hemolysis
The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.		02.0510
Staphylococcal Infections
Infections with bacteria of the genus STAPHYLOCOCCUS.		02.0510
Bacteremia
The presence of viable bacteria circulating in the blood. Fever, chills, tachycardia, and tachypnea are common acute manifestations of bacteremia. The majority of cases are seen in already hospitalized patients, most of whom have underlying diseases or procedures which render their bloodstreams susceptible to invasion.		02.0510