Page last updated: 2024-11-12

scyphostatin

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

Description

scyphostatin: a neutral sphingomyelinase inhibitor isolated from Trichopeziza mollissima; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID11248738
CHEMBL ID418376
CHEBI ID188858
SCHEMBL ID23958256
MeSH IDM0334663

Synonyms (8)

Synonym
CHEMBL418376 ,
scyphostatin
bdbm50100341
(2e,4e,6e,12e)-(8r,10s,14r)-8,10,12,14-tetramethyl-hexadeca-2,4,6,12-tetraenoic acid [(s)-1-hydroxymethyl-2-((1s,2s,6s)-2-hydroxy-3-oxo-7-oxa-bicyclo[4.1.0]hept-4-en-2-yl)-ethyl]-amide
(+)-scyphostatin
(2e,4e,6e,8r,10s,12e,14r)-n-[(2s)-1-hydroxy-3-[(1s,2s,6s)-2-hydroxy-3-oxo-7-oxabicyclo[4.1.0]hept-4-en-2-yl]propan-2-yl]-8,10,12,14-tetramethylhexadeca-2,4,6,12-tetraenamide
CHEBI:188858
SCHEMBL23958256

Research Excerpts

Overview

Scyphostatin proved to be a potent inhibitor of N-SMase with 95% inhibition observed at 20 microM. It is a specific inhibitor for mammalian neutral magnesium-dependent sphingomyelinase.

ExcerptReferenceRelevance
"Scyphostatin is a specific inhibitor for mammalian neutral magnesium-dependent sphingomyelinase with a fifty percent inhibition concentration (IC50) value of 1.0 microM. "( Biological activities of scyphostatin, a neutral sphingomyelinase inhibitor from a discomycete, Trichopeziza mollissima.
Doi-Yoshioka, H; Kumakura, S; Masuda-Inoue, S; Nara, F; Ogita, T; Suzuki-Konagai, K; Tanaka, M; Yamasato, Y, 1999
)
2.05
"Scyphostatin proved to be a potent inhibitor of N-SMase with 95% inhibition observed at 20 microM scyphostatin."( Purification and characterization of a magnesium-dependent neutral sphingomyelinase from bovine brain.
Bernardo, K; Kreder, D; Krönke, M; Krut, O; Meyer, HE; Micheli, M; Sandhoff, K; Schäfer, R; Schmidt, WE; Schröder, JM; Sickman, A; Wiegmann, K, 2000
)
1.03
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
cyclohexenonesAny six-membered alicyclic ketone having one double bond in the ring.
[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 (2)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Sphingomyelin phosphodiesterase 2Homo sapiens (human)IC50 (µMol)1.00001.00001.00001.0000AID147530
Sphingomyelin phosphodiesterase 2Rattus norvegicus (Norway rat)IC50 (µMol)25.15001.00001.00001.0000AID204029; AID204030
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (4)

Processvia Protein(s)Taxonomy
sphingomyelin catabolic processSphingomyelin phosphodiesterase 2Homo sapiens (human)
sphingolipid catabolic processSphingomyelin phosphodiesterase 2Homo sapiens (human)
ceramide biosynthetic processSphingomyelin phosphodiesterase 2Homo sapiens (human)
sphingomyelin metabolic processSphingomyelin phosphodiesterase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (4)

Processvia Protein(s)Taxonomy
sphingomyelin phosphodiesterase activitySphingomyelin phosphodiesterase 2Homo sapiens (human)
protein bindingSphingomyelin phosphodiesterase 2Homo sapiens (human)
phosphoric diester hydrolase activitySphingomyelin phosphodiesterase 2Homo sapiens (human)
metal ion bindingSphingomyelin phosphodiesterase 2Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (4)

Processvia Protein(s)Taxonomy
plasma membraneSphingomyelin phosphodiesterase 2Homo sapiens (human)
cell peripherySphingomyelin phosphodiesterase 2Homo sapiens (human)
endoplasmic reticulumSphingomyelin phosphodiesterase 2Homo sapiens (human)
caveolaSphingomyelin phosphodiesterase 2Homo sapiens (human)
plasma membraneSphingomyelin phosphodiesterase 2Rattus norvegicus (Norway rat)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (5)

Assay IDTitleYearJournalArticle
AID147530Inhibitory activity against neutral sphingomyelinase (N-SMase) from bovine brain microsomes2003Bioorganic & medicinal chemistry letters, Jan-20, Volume: 13, Issue:2
Synthesis of non-competitive inhibitors of sphingomyelinases with significant activity.
AID204029Inhibitory concentration against neutral sphingomyelinase (N-Smase) from rat brain microsomes2001Bioorganic & medicinal chemistry letters, May-21, Volume: 11, Issue:10
Synthesis and evaluation of a difluoromethylene analogue of sphingomyelin as an inhibitor of sphingomyelinase.
AID89038Inhibitory concentration against liposaccharide induced IL1-beta production in human peripheral monocytes2001Bioorganic & medicinal chemistry letters, May-21, Volume: 11, Issue:10
Synthesis and evaluation of a difluoromethylene analogue of sphingomyelin as an inhibitor of sphingomyelinase.
AID204030Inhibitory concentration against lysosomal neutral sphingomyelinase (N-Smase)2001Bioorganic & medicinal chemistry letters, May-21, Volume: 11, Issue:10
Synthesis and evaluation of a difluoromethylene analogue of sphingomyelin as an inhibitor of sphingomyelinase.
AID147071Inhibitory concentration against the membrane neutral magnesium-dependent Sphingomyelinase (N-SMase) using rat brain microsomes as the enzyme source2003Bioorganic & medicinal chemistry letters, Jun-16, Volume: 13, Issue:12
Sphingomyelin analogues as inhibitors of sphingomyelinase.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (38)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's3 (7.89)18.2507
2000's26 (68.42)29.6817
2010's8 (21.05)24.3611
2020's1 (2.63)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 18.79

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 Index18.79 (24.57)
Research Supply Index3.66 (2.92)
Research Growth Index4.82 (4.65)
Search Engine Demand Index15.26 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (18.79)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (2.63%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other37 (97.37%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]