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 Source	ID
PubMed CID	10376483
CHEMBL ID	419498
CHEBI ID	167320
SCHEMBL ID	16431626
SCHEMBL ID	21333942
MeSH ID	M0255012

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)

Role	Description
bacterial metabolite	Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
calpain inhibitor	An 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)

Class	Description
benzenes	Any benzenoid aromatic compound consisting of the benzene skeleton and its substituted derivatives.
pyrazinone	Any 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

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Calpain-1 catalytic subunit	Homo sapiens (human)	IC50 (µMol)	1.2000	0.0002	1.0592	10.0000	AID46332
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (8)

Process	via Protein(s)	Taxonomy
proteolysis	Calpain-1 catalytic subunit	Homo sapiens (human)
positive regulation of cell population proliferation	Calpain-1 catalytic subunit	Homo sapiens (human)
regulation of macroautophagy	Calpain-1 catalytic subunit	Homo sapiens (human)
receptor catabolic process	Calpain-1 catalytic subunit	Homo sapiens (human)
regulation of catalytic activity	Calpain-1 catalytic subunit	Homo sapiens (human)
mammary gland involution	Calpain-1 catalytic subunit	Homo sapiens (human)
self proteolysis	Calpain-1 catalytic subunit	Homo sapiens (human)
regulation of NMDA receptor activity	Calpain-1 catalytic subunit	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Process	via Protein(s)	Taxonomy
calcium-dependent cysteine-type endopeptidase activity	Calpain-1 catalytic subunit	Homo sapiens (human)
calcium ion binding	Calpain-1 catalytic subunit	Homo sapiens (human)
protein binding	Calpain-1 catalytic subunit	Homo sapiens (human)
peptidase activity	Calpain-1 catalytic subunit	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (12)

Process	via Protein(s)	Taxonomy
cornified envelope	Calpain-1 catalytic subunit	Homo sapiens (human)
extracellular region	Calpain-1 catalytic subunit	Homo sapiens (human)
mitochondrion	Calpain-1 catalytic subunit	Homo sapiens (human)
lysosome	Calpain-1 catalytic subunit	Homo sapiens (human)
cytosol	Calpain-1 catalytic subunit	Homo sapiens (human)
plasma membrane	Calpain-1 catalytic subunit	Homo sapiens (human)
focal adhesion	Calpain-1 catalytic subunit	Homo sapiens (human)
membrane	Calpain-1 catalytic subunit	Homo sapiens (human)
extracellular exosome	Calpain-1 catalytic subunit	Homo sapiens (human)
calpain complex	Calpain-1 catalytic subunit	Homo sapiens (human)
ficolin-1-rich granule lumen	Calpain-1 catalytic subunit	Homo sapiens (human)
cytoplasm	Calpain-1 catalytic subunit	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (3)

Assay ID	Title	Year	Journal	Article
AID240485	Concentration required for inhibition of calpain	2005	Bioorganic & medicinal chemistry letters, Jun-15, Volume: 15, Issue:12	Synthesis of a small library of diketopiperazines as potential inhibitors of calpain.
AID243896	Percent inhibition of human calpain 1 at 550 uM; Inhibition within 110%	2005	Bioorganic & medicinal chemistry letters, Jun-15, Volume: 15, Issue:12	Synthesis of a small library of diketopiperazines as potential inhibitors of calpain.
AID46332	Compound was tested for its inhibitory activity against calpain isolated from Streptomyces species	2001	Bioorganic & 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)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	0 (0.00)	18.7374
1990's	1 (10.00)	18.2507
2000's	2 (20.00)	29.6817
2010's	6 (60.00)	24.3611
2020's	1 (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.

Metric	This Compound (vs All)
Research Demand Index	17.75 (24.57)
Research Supply Index	2.40 (2.92)
Research Growth Index	4.96 (4.65)
Search Engine Demand Index	10.37 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (17.75)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	10 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
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.	3.67	9	diazine; 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).	2.02	1	2,5-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.	2.08	1	S-glycosyl compound
cyclo(l-leucyl-l-tryptophyl) cyclo(L-leucyl-L-tryptophyl): structure in first source	2.02	1
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.	2.15	1
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).	2.02	1	2,5-diketopiperazines	metabolite
(11S,14S)-Cyclo-(L-Trp-L-Phe) [no description available]	2.02	1	indoles	Aspergillus 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).	2.02	1	cinnamic acids; organoiodine compound; thioenol	apoptosis inhibitor; calpain inhibitor
calpain inhibitor iii calpain inhibitor III: potential anticataract drug	2.02	1
cyclo(tyrosyl-tyrosyl) cyclo(L-tyrosyl-L-tyrosyl) : A cyclo(tyrosyl-tyrosyl) in which both stereocentres have L-configuration. Synthesized by Mycobacterium tuberculosis.	2.02	1	cyclo(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.	7.41	2

Condition	Relationship Strength	Studies
Extravascular Hemolysis [description not available]	2.05	1
Infections, Staphylococcal [description not available]	2.05	1
Hemolysis The destruction of ERYTHROCYTES by many different causal agents such as antibodies, bacteria, chemicals, temperature, and changes in tonicity.	2.05	1
Staphylococcal Infections Infections with bacteria of the genus STAPHYLOCOCCUS.	2.05	1
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.	2.05	1

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