Page last updated: 2024-12-10

gl-4

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 CID4369162
CHEMBL ID489798
MeSH IDM0055474

Synonyms (12)

Synonym
gl4 ,
(5s,7r,8s,9s,10r)-8,9,10-trihydroxy-7-(hydroxymethyl)-2-thioxo-6-oxa-1,3-diazaspiro[4.5]decan-4-one
8,9,10-trihydroxy-7-hydroxymethyl-2-thioxo-6-oxa-1,3-diaza-spiro[4.5]decan-4-one
DB02964
1HLF
bdbm50263769
(5s,7r,8s,9s,10r)-8,9,10-trihydroxy-7-hydroxymethyl-2-thioxo-6-oxa-1,3-diaza-spiro[4.5]decan-4-one
CHEMBL489798 ,
(2r,3s,4s,5r,6s)-3,4,5-trihydroxy-2-hydroxymethyl-7,9-diaza-1-oxa-spiro[4,5]decane-10-one-8-thione
W-201947
(5s,7r,8s,9s,10r)-8,9,10-trihydroxy-7-(hydroxymethyl)-2-sulfanylidene-6-oxa-1,3-diazaspiro[4.5]decan-4-one
PD059744
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (10)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, Protein (glycogen Phosphorylase)Oryctolagus cuniculus (rabbit)Ki2.30002.30002.70003.1000AID977610
Chain A, Glycogen PhosphorylaseOryctolagus cuniculus (rabbit)Ki2.30002.30002.70003.1000AID977610
Glycogen phosphorylase, muscle formOryctolagus cuniculus (rabbit)Ki5.10000.02504.89039.0000AID1276749; AID387864; AID453252; AID644850
Glycogen phosphorylase, liver formHomo sapiens (human)Ki29.80000.40002.75005.1000AID101851
Cytochrome P450 3A4Homo sapiens (human)Ki29.80000.00011.41629.9000AID101851
Glycogen phosphorylase, liver formRattus norvegicus (Norway rat)Ki22.20007.00007.00007.0000AID101995; AID101996; AID1280560
Glycogen phosphorylase, brain formHomo sapiens (human)Ki7.00000.00404.06807.0000AID141117
Glycogen phosphorylase, muscle formHomo sapiens (human)Ki8.00000.00403.43475.2000AID141231; AID141233
Substance-P receptorCavia porcellus (domestic guinea pig)Ki10.90000.00130.69133.4000AID141231
Leukotriene B4 receptor 1Homo sapiens (human)Ki7.00000.00010.51267.0000AID101996
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (32)

Processvia Protein(s)Taxonomy
glycogen metabolic processGlycogen phosphorylase, liver formHomo sapiens (human)
5-phosphoribose 1-diphosphate biosynthetic processGlycogen phosphorylase, liver formHomo sapiens (human)
response to bacteriumGlycogen phosphorylase, liver formHomo sapiens (human)
glucose homeostasisGlycogen phosphorylase, liver formHomo sapiens (human)
necroptotic processGlycogen phosphorylase, liver formHomo sapiens (human)
glycogen catabolic processGlycogen phosphorylase, liver formHomo sapiens (human)
lipid hydroxylationCytochrome P450 3A4Homo sapiens (human)
lipid metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid catabolic processCytochrome P450 3A4Homo sapiens (human)
xenobiotic metabolic processCytochrome P450 3A4Homo sapiens (human)
steroid metabolic processCytochrome P450 3A4Homo sapiens (human)
cholesterol metabolic processCytochrome P450 3A4Homo sapiens (human)
androgen metabolic processCytochrome P450 3A4Homo sapiens (human)
estrogen metabolic processCytochrome P450 3A4Homo sapiens (human)
alkaloid catabolic processCytochrome P450 3A4Homo sapiens (human)
monoterpenoid metabolic processCytochrome P450 3A4Homo sapiens (human)
calcitriol biosynthetic process from calciolCytochrome P450 3A4Homo sapiens (human)
xenobiotic catabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D metabolic processCytochrome P450 3A4Homo sapiens (human)
vitamin D catabolic processCytochrome P450 3A4Homo sapiens (human)
retinol metabolic processCytochrome P450 3A4Homo sapiens (human)
retinoic acid metabolic processCytochrome P450 3A4Homo sapiens (human)
long-chain fatty acid biosynthetic processCytochrome P450 3A4Homo sapiens (human)
aflatoxin metabolic processCytochrome P450 3A4Homo sapiens (human)
oxidative demethylationCytochrome P450 3A4Homo sapiens (human)
glycogen catabolic processGlycogen phosphorylase, brain formHomo sapiens (human)
glycogen metabolic processGlycogen phosphorylase, muscle formHomo sapiens (human)
glycogen catabolic processGlycogen phosphorylase, muscle formHomo sapiens (human)
muscle contractionLeukotriene B4 receptor 1Homo sapiens (human)
inflammatory responseLeukotriene B4 receptor 1Homo sapiens (human)
immune responseLeukotriene B4 receptor 1Homo sapiens (human)
G protein-coupled receptor signaling pathwayLeukotriene B4 receptor 1Homo sapiens (human)
phospholipase C-activating G protein-coupled receptor signaling pathwayLeukotriene B4 receptor 1Homo sapiens (human)
leukotriene signaling pathwayLeukotriene B4 receptor 1Homo sapiens (human)
neuropeptide signaling pathwayLeukotriene B4 receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (38)

Processvia Protein(s)Taxonomy
purine nucleobase bindingGlycogen phosphorylase, liver formHomo sapiens (human)
protein bindingGlycogen phosphorylase, liver formHomo sapiens (human)
ATP bindingGlycogen phosphorylase, liver formHomo sapiens (human)
glucose bindingGlycogen phosphorylase, liver formHomo sapiens (human)
glycogen phosphorylase activityGlycogen phosphorylase, liver formHomo sapiens (human)
AMP bindingGlycogen phosphorylase, liver formHomo sapiens (human)
vitamin bindingGlycogen phosphorylase, liver formHomo sapiens (human)
bile acid bindingGlycogen phosphorylase, liver formHomo sapiens (human)
identical protein bindingGlycogen phosphorylase, liver formHomo sapiens (human)
linear malto-oligosaccharide phosphorylase activityGlycogen phosphorylase, liver formHomo sapiens (human)
SHG alpha-glucan phosphorylase activityGlycogen phosphorylase, liver formHomo sapiens (human)
pyridoxal phosphate bindingGlycogen phosphorylase, liver formHomo sapiens (human)
monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
steroid bindingCytochrome P450 3A4Homo sapiens (human)
iron ion bindingCytochrome P450 3A4Homo sapiens (human)
protein bindingCytochrome P450 3A4Homo sapiens (human)
steroid hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
retinoic acid 4-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
oxidoreductase activityCytochrome P450 3A4Homo sapiens (human)
oxygen bindingCytochrome P450 3A4Homo sapiens (human)
enzyme bindingCytochrome P450 3A4Homo sapiens (human)
heme bindingCytochrome P450 3A4Homo sapiens (human)
vitamin D3 25-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
caffeine oxidase activityCytochrome P450 3A4Homo sapiens (human)
quinine 3-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
testosterone 6-beta-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1-alpha,25-dihydroxyvitamin D3 23-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 8,9 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 11,12 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
anandamide 14,15 epoxidase activityCytochrome P450 3A4Homo sapiens (human)
aromatase activityCytochrome P450 3A4Homo sapiens (human)
vitamin D 24-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 16-alpha-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
estrogen 2-hydroxylase activityCytochrome P450 3A4Homo sapiens (human)
1,8-cineole 2-exo-monooxygenase activityCytochrome P450 3A4Homo sapiens (human)
protein bindingGlycogen phosphorylase, brain formHomo sapiens (human)
glycogen phosphorylase activityGlycogen phosphorylase, brain formHomo sapiens (human)
linear malto-oligosaccharide phosphorylase activityGlycogen phosphorylase, brain formHomo sapiens (human)
SHG alpha-glucan phosphorylase activityGlycogen phosphorylase, brain formHomo sapiens (human)
pyridoxal phosphate bindingGlycogen phosphorylase, brain formHomo sapiens (human)
nucleotide bindingGlycogen phosphorylase, muscle formHomo sapiens (human)
protein bindingGlycogen phosphorylase, muscle formHomo sapiens (human)
glycogen phosphorylase activityGlycogen phosphorylase, muscle formHomo sapiens (human)
linear malto-oligosaccharide phosphorylase activityGlycogen phosphorylase, muscle formHomo sapiens (human)
SHG alpha-glucan phosphorylase activityGlycogen phosphorylase, muscle formHomo sapiens (human)
pyridoxal phosphate bindingGlycogen phosphorylase, muscle formHomo sapiens (human)
nucleotide bindingLeukotriene B4 receptor 1Homo sapiens (human)
leukotriene receptor activityLeukotriene B4 receptor 1Homo sapiens (human)
G protein-coupled peptide receptor activityLeukotriene B4 receptor 1Homo sapiens (human)
leukotriene B4 receptor activityLeukotriene B4 receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (11)

Processvia Protein(s)Taxonomy
extracellular regionGlycogen phosphorylase, liver formHomo sapiens (human)
cytosolGlycogen phosphorylase, liver formHomo sapiens (human)
secretory granule lumenGlycogen phosphorylase, liver formHomo sapiens (human)
extracellular exosomeGlycogen phosphorylase, liver formHomo sapiens (human)
ficolin-1-rich granule lumenGlycogen phosphorylase, liver formHomo sapiens (human)
cytoplasmGlycogen phosphorylase, liver formHomo sapiens (human)
cytoplasmCytochrome P450 3A4Homo sapiens (human)
endoplasmic reticulum membraneCytochrome P450 3A4Homo sapiens (human)
intracellular membrane-bounded organelleCytochrome P450 3A4Homo sapiens (human)
extracellular regionGlycogen phosphorylase, brain formHomo sapiens (human)
cytoplasmGlycogen phosphorylase, brain formHomo sapiens (human)
membraneGlycogen phosphorylase, brain formHomo sapiens (human)
azurophil granule lumenGlycogen phosphorylase, brain formHomo sapiens (human)
extracellular exosomeGlycogen phosphorylase, brain formHomo sapiens (human)
cytoplasmGlycogen phosphorylase, brain formHomo sapiens (human)
cytosolGlycogen phosphorylase, muscle formHomo sapiens (human)
extracellular exosomeGlycogen phosphorylase, muscle formHomo sapiens (human)
cytoplasmGlycogen phosphorylase, muscle formHomo sapiens (human)
plasma membraneLeukotriene B4 receptor 1Homo sapiens (human)
plasma membraneLeukotriene B4 receptor 1Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (16)

Assay IDTitleYearJournalArticle
AID141119Inhibitory activity against muscle Glycogen Phosphorylase b2001Journal of medicinal chemistry, Aug-16, Volume: 44, Issue:17
Synthesis of and a comparative study on the inhibition of muscle and liver glycogen phosphorylases by epimeric pairs of d-gluco- and d-xylopyranosylidene-spiro-(thio)hydantoins and N-(d-glucopyranosyl) amides.
AID1276749Competitive inhibition of rabbit skeletal muscle glycogen phosphorylase b2016European journal of medicinal chemistry, Jan-27, Volume: 108Glucose-derived spiro-isoxazolines are anti-hyperglycemic agents against type 2 diabetes through glycogen phosphorylase inhibition.
AID141117Inhibitory activity against liver Glycogen Phosphorylase b2001Journal of medicinal chemistry, Aug-16, Volume: 44, Issue:17
Synthesis of and a comparative study on the inhibition of muscle and liver glycogen phosphorylases by epimeric pairs of d-gluco- and d-xylopyranosylidene-spiro-(thio)hydantoins and N-(d-glucopyranosyl) amides.
AID141233Inhibitor constant was measured against Muscle phosphorylase b in rabbit1999Bioorganic & medicinal chemistry letters, May-17, Volume: 9, Issue:10
Efficient inhibition of muscle and liver glycogen phosphorylases by a new glucopyranosylidene-spiro-thiohydantoin.
AID141231Inhibitor constant was measured against Muscle phosphorylase a in rabbit1999Bioorganic & medicinal chemistry letters, May-17, Volume: 9, Issue:10
Efficient inhibition of muscle and liver glycogen phosphorylases by a new glucopyranosylidene-spiro-thiohydantoin.
AID101995Inhibitor constant was measured against Liver phosphorylase a in rat1999Bioorganic & medicinal chemistry letters, May-17, Volume: 9, Issue:10
Efficient inhibition of muscle and liver glycogen phosphorylases by a new glucopyranosylidene-spiro-thiohydantoin.
AID644850Inhibition of rabbit muscle glycogen phosphorylase b assessed as inorganic phosphate release at pH 6.82012Bioorganic & medicinal chemistry, Mar-01, Volume: 20, Issue:5
N-(4-Substituted-benzoyl)-N'-(β-d-glucopyranosyl)ureas as inhibitors of glycogen phosphorylase: Synthesis and evaluation by kinetic, crystallographic, and molecular modelling methods.
AID101852Inhibitory activity against muscle Glycogen Phosphorylase a2001Journal of medicinal chemistry, Aug-16, Volume: 44, Issue:17
Synthesis of and a comparative study on the inhibition of muscle and liver glycogen phosphorylases by epimeric pairs of d-gluco- and d-xylopyranosylidene-spiro-(thio)hydantoins and N-(d-glucopyranosyl) amides.
AID453252Inhibition of rabbit muscle glycogen phosphorylase b2009Bioorganic & medicinal chemistry, Oct-15, Volume: 17, Issue:20
Glucose-based spiro-isoxazolines: a new family of potent glycogen phosphorylase inhibitors.
AID101996Inhibitor constant was measured against Liver phosphorylase b in rat1999Bioorganic & medicinal chemistry letters, May-17, Volume: 9, Issue:10
Efficient inhibition of muscle and liver glycogen phosphorylases by a new glucopyranosylidene-spiro-thiohydantoin.
AID101851Inhibitory activity against liver Glycogen Phosphorylase a2001Journal of medicinal chemistry, Aug-16, Volume: 44, Issue:17
Synthesis of and a comparative study on the inhibition of muscle and liver glycogen phosphorylases by epimeric pairs of d-gluco- and d-xylopyranosylidene-spiro-(thio)hydantoins and N-(d-glucopyranosyl) amides.
AID387864Inhibition of rabbit muscle glycogen phosphorylase b2008Bioorganic & medicinal chemistry letters, Oct-15, Volume: 18, Issue:20
Novel design principle validated: glucopyranosylidene-spiro-oxathiazole as new nanomolar inhibitor of glycogen phosphorylase, potential antidiabetic agent.
AID1563539Inhibition of rabbit muscle Glycogen phosphorylase b using glucose-1-phosphate as substrate in presence of AMP2019Journal of medicinal chemistry, 07-11, Volume: 62, Issue:13
Glucopyranosylidene-spiro-imidazolinones, a New Ring System: Synthesis and Evaluation as Glycogen Phosphorylase Inhibitors by Enzyme Kinetics and X-ray Crystallography.
AID1280560Inhibition of rat liver glycogen phosphorylase2015ACS medicinal chemistry letters, Dec-10, Volume: 6, Issue:12
4(5)-Aryl-2-C-glucopyranosyl-imidazoles as New Nanomolar Glucose Analogue Inhibitors of Glycogen Phosphorylase.
AID977610Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB2002Bioorganic & medicinal chemistry, Feb, Volume: 10, Issue:2
Kinetic and crystallographic studies of glucopyranosylidene spirothiohydantoin binding to glycogen phosphorylase B.
AID1811Experimentally measured binding affinity data derived from PDB2002Bioorganic & medicinal chemistry, Feb, Volume: 10, Issue:2
Kinetic and crystallographic studies of glucopyranosylidene spirothiohydantoin binding to glycogen phosphorylase B.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (9)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's1 (11.11)18.2507
2000's4 (44.44)29.6817
2010's4 (44.44)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: 49.90

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

MetricThis Compound (vs All)
Research Demand Index49.90 (24.57)
Research Supply Index2.30 (2.92)
Research Growth Index4.92 (4.65)
Search Engine Demand Index144.48 (26.88)
Search Engine Supply Index3.95 (0.95)

This Compound (49.90)

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%
Other9 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]