Compounds > fagomine
Page last updated: 2024-12-06

fagomine

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Description

fagomine: structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID72259
CHEMBL ID108084
CHEBI ID4969
SCHEMBL ID142574
MeSH IDM0275519

Synonyms (32)

Synonym
HY-13005
(2r,3r,4r)-2-(hydroxymethyl)piperidine-3,4-diol
3,4-piperidinediol, 2-(hydroxymethyl)-, (2r,3r,4r)-
1,2,5-trideoxy-1,5-imino-d-arabino-hexitol
FAG ,
53185-12-9
fagomine
bdbm50240725
(2r,3r,4r)-2-hydroxymethyl-piperidine-3,4-diol
chebi:4969 ,
d-fagomine
CHEMBL108084 ,
AKOS006345435
unii-1m10c1p4sm
1m10c1p4sm ,
d-arabino-hexitol, 1,2,5-trideoxy-1,5-imino-
CS-0365
(2r,3r,4r)-2-(hydroxymethyl)-3,4-piperidinediol
fagomine, (+)-
fagomine, (d)-
SCHEMBL142574
1,5-imino-1,2,5-trideoxy-d-arabino-hexitol
YZNNBIPIQWYLDM-HSUXUTPPSA-N
AC-26456
surecn142574
DTXSID10201243
2-(hydroxymethyl)-(2r,3r,4r)-3,4-piperidinediol
(2r,3r,4r)-2-hydroxymethylpiperidine-3,4-diol
Q27106598
(d)-fagomine
F83787
MS-22836

Research Excerpts

Overview

D-Fagomine is an iminosugar first found in buckwheat (Fagopyrum esculentum Moench) If used as a dietary supplement, it may reduce the risks of developing insulin resistance, becoming overweight and suffering from an excess of potentially pathogenic bacteria.

ExcerptReferenceRelevance
"d-Fagomine is an iminosugar found in buckwheat that is capable of inhibiting the adhesion of potentially pathogenic bacteria to epithelial mucosa and reducing the postprandial blood glucose concentration. "( Fate of d-Fagomine after Oral Administration to Rats.
Amézqueta, S; Hereu, M; Martínez-Guimet, C; Moreno, A; Ramos-Romero, S; Torres, JL, 2017)		1.58
"d-Fagomine is an iminosugar that has been shown to selectively agglutinate Enterobacteriales in vitro."( Effect of (D)-fagomine on excreted Enterobacteria and weight gain in rats fed a high-fat high-sucrose diet.
Casado, M; Clapés, P; Gómez, L; Molinar-Toribio, E; Pérez-Jiménez, J; Piña, B; Ramos-Romero, S; Torres, JL, 2014)		1.32
"d-Fagomine is a natural iminosugar that counteracts the short-term effects of a high-energy-dense diet on body weight, fasting blood glucose levels and the proportion of gut Enterobacteriales. "( D-Fagomine attenuates metabolic alterations induced by a high-energy-dense diet in rats.
Adeva, A; Clapés, P; Gómez, L; Jáuregui, O; Joglar, J; Molinar-Toribio, E; Nogués, MR; Pérez-Jiménez, J; Ramos-Romero, S; Taltavull, N; Torres, JL, 2015)		1.86
"D-Fagomine is an iminosugar originally isolated from seeds of buckwheat (Fagopyrum sculentum Moench), present in the human diet and now available as a pure crystalline product. "( D-Fagomine lowers postprandial blood glucose and modulates bacterial adhesion.
Adelantado, C; Calvo-Torras, MÁ; Cañas, X; Clapés, P; Gómez, L; Juan, ME; Lozano, C; Molinar-Toribio, E; Planas, JM; Pumarola, S; Torres, JL, 2012)		1.82
"D-Fagomine is an iminosugar first found in buckwheat (Fagopyrum esculentum Moench) which if used as a dietary supplement or functional food component may reduce the risks of developing insulin resistance, becoming overweight and suffering from an excess of potentially pathogenic bacteria. "( Determination of D-fagomine in buckwheat and mulberry by cation exchange HPLC/ESI-Q-MS.
Abián, J; Amézqueta, S; Carrascal, M; Fuguet, E; Galán, E; Torres, JL, 2012)		1.43

Bioavailability

ExcerptReferenceRelevance
" Knowledge regarding the in vivo bioavailability and bioactivity of MLIs are crucial to understand their role and function and human health."( A comprehensive review on the production, pharmacokinetics and health benefits of mulberry leaf iminosugars: Main focus on 1-deoxynojirimycin, d-fagomine, and 2-O-ɑ-d-galactopyranosyl-DNJ.
Nakagawa, K; Parida, IS; Takasu, S, 2023)		1.11
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
piperidines
[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 (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Ceramide glucosyltransferaseMus musculus (house mouse)IC50 (µMol)10.00000.20001.46674.0000AID652571
Sucrase-isomaltase, intestinalRattus norvegicus (Norway rat)IC50 (µMol)133.40000.04001.848310.0000AID342795; AID342797; AID402839; AID613047; AID613048
Glycogen debranching enzymeOryctolagus cuniculus (rabbit)IC50 (µMol)2.10000.11000.69752.1000AID342805
Lysosomal acid glucosylceramidaseBos taurus (cattle)IC50 (µMol)250.00005.60005.60005.6000AID613051
Beta-galactosidaseBos taurus (cattle)IC50 (µMol)38.00001.50002.70003.6000AID613054
Lysosomal alpha-glucosidaseRattus norvegicus (Norway rat)IC50 (µMol)820.00000.08002.50619.8500AID342793
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (7)

Processvia Protein(s)Taxonomy
glucosylceramide catabolic processLysosomal acid glucosylceramidaseBos taurus (cattle)
autophagyLysosomal acid glucosylceramidaseBos taurus (cattle)
lysosome organizationLysosomal acid glucosylceramidaseBos taurus (cattle)
cholesterol metabolic processLysosomal acid glucosylceramidaseBos taurus (cattle)
lipid glycosylationLysosomal acid glucosylceramidaseBos taurus (cattle)
regulation of TOR signalingLysosomal acid glucosylceramidaseBos taurus (cattle)
carbohydrate metabolic processBeta-galactosidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
galactosylceramidase activityLysosomal acid glucosylceramidaseBos taurus (cattle)
glucosylceramidase activityLysosomal acid glucosylceramidaseBos taurus (cattle)
glucosyltransferase activityLysosomal acid glucosylceramidaseBos taurus (cattle)
steryl-beta-glucosidase activityLysosomal acid glucosylceramidaseBos taurus (cattle)
beta-galactosidase activityBeta-galactosidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (5)

Processvia Protein(s)Taxonomy
lysosomeLysosomal acid glucosylceramidaseBos taurus (cattle)
lysosomal membraneLysosomal acid glucosylceramidaseBos taurus (cattle)
endoplasmic reticulumLysosomal acid glucosylceramidaseBos taurus (cattle)
Golgi apparatusLysosomal acid glucosylceramidaseBos taurus (cattle)
trans-Golgi networkLysosomal acid glucosylceramidaseBos taurus (cattle)
lysosomeBeta-galactosidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (62)

Assay IDTitleYearJournalArticle
AID40436Concentration that causes 50% inhibition of mammalian cellobiase beta-glucosidase was determined in rat intestine; NI is less than 50 % inhibition at 1000 uM1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID37285Concentration that causes 50% inhibition of mammalian alpha-glucosidase (lysosomal) was determined in rat liver; NI is less than 50 % inhibition at 1000 uM1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID400360Potentiation of 8.3 mM glucose-induced immunoreactive insulin release in perfused Wistar rat pancreas at 1 mM by radioimmunoassay1998Journal of natural products, Mar, Volume: 61, Issue:3
Antihyperglycemic effects of N-containing sugars from Xanthocercis zambesiaca, Morus bombycis, Aglaonema treubii, and Castanospermum australe in streptozotocin-diabetic mice.
AID400356Antihyperglycemic effect on STZ-diabetic ddY mouse assessed as increase in plasma insulin level at 300 umol/kg, ip after 30 mins by ELISA1998Journal of natural products, Mar, Volume: 61, Issue:3
Antihyperglycemic effects of N-containing sugars from Xanthocercis zambesiaca, Morus bombycis, Aglaonema treubii, and Castanospermum australe in streptozotocin-diabetic mice.
AID37277Concentration that causes 50% inhibition of mammalian alpha-glucosidase (isomaltase) was determined in rat intestine1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID613035Inhibition of almond beta-glucosidase assessed as production of 4-methylumbelliferone using 4-methylumbelliferyl beta-D-glucoside as substrate at 1000 uM by spectrophotometry2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.
AID400354Antihyperglycemic effect on fasted normal ddY mouse assessed as reduction in blood glucose level at 300 umol/kg, ip by glucose oxidase method1998Journal of natural products, Mar, Volume: 61, Issue:3
Antihyperglycemic effects of N-containing sugars from Xanthocercis zambesiaca, Morus bombycis, Aglaonema treubii, and Castanospermum australe in streptozotocin-diabetic mice.
AID342800Inhibition of human lysosomal alpha-glucosidase at 1000 uM2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.
AID652570Inhibition of glucosylceramide synthase in mouse RAW cells up to 20 uM preincubated for 15 mins followed by substrate addition and measured after 1 hr by fluorescence scanner2011ACS medicinal chemistry letters, Jul-14, Volume: 2, Issue:7
Assessment of partially deoxygenated deoxynojirimycin derivatives as glucosylceramide synthase inhibitors.
AID402839Inhibition of Wistar rat intestinal isomaltase by glucose B-test1997Journal of natural products, Mar, Volume: 60, Issue:3
Fagomine isomers and glycosides from Xanthocercis zambesiaca.
AID342803Inhibition of rabbit glycogen phosphorylase B2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.
AID342802Inhibition of human lysosomal beta-glucosidase at 1000 uM2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.
AID40176Concentration that causes 50% inhibition of mammalian lactase beta-galactosidase was determined in rat intestine1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID33282Concentration that causes 50% inhibition of mammalian alpha-mannosidase (lysosomal) was determined in rat liver; NI is less than 50 % inhibition at 1000 uM1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID33277Concentration that causes 50% inhibition of mammalian alpha-mannosidase (golgi I) was determined in rat liver; NI is less than 50 % inhibition at 1000 uM1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID37435Concentration that causes 50% inhibition of mammalian alpha-glucosidase (endoplasmic reticulum glucosidase II) was determined in rat liver1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID402847Inhibition of green coffee bean alpha-galactosidase by spectrophotometry1997Journal of natural products, Mar, Volume: 60, Issue:3
Fagomine isomers and glycosides from Xanthocercis zambesiaca.
AID613054Inhibition of bovine liver beta-galactosidase assessed as production of p-nitrophenol by spectrophotometry2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.
AID613046Inhibition of rat intestinal maltase assessed as production of D-glucose using maltose as substrate after 10 to 30 mins by spectrophotometry2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.
AID37272Inhibition of mammalian alpha-glucosidase (lysosomal) was determined in bovine liver1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID400353Antihyperglycemic effect in STZ-diabetic ddY mouse assessed as reduction in blood glucose level at 150 umol/kg, ip after 2 hrs by glucose oxidase method1998Journal of natural products, Mar, Volume: 61, Issue:3
Antihyperglycemic effects of N-containing sugars from Xanthocercis zambesiaca, Morus bombycis, Aglaonema treubii, and Castanospermum australe in streptozotocin-diabetic mice.
AID402851Inhibition of bovine liver beta-galactosidase by spectrophotometry1997Journal of natural products, Mar, Volume: 60, Issue:3
Fagomine isomers and glycosides from Xanthocercis zambesiaca.
AID36813Concentration that causes 50% inhibition of mammalian alpha-L-fucosidase was determined in bovine epididymis1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID613056Inhibition of rat intestinal lactase assessed as production of p-nitrophenol at 1000 uM by spectrophotometry2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.
AID402846Inhibition of rat liver lysosomal alpha-galactosidase at 1000 uM by spectrophotometry1997Journal of natural products, Mar, Volume: 60, Issue:3
Fagomine isomers and glycosides from Xanthocercis zambesiaca.
AID402849Inhibition of rat liver beta-galactosidase by spectrophotometry1997Journal of natural products, Mar, Volume: 60, Issue:3
Fagomine isomers and glycosides from Xanthocercis zambesiaca.
AID342805Inhibition of rabbit muscle amylo-1,6-glucosidase2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.
AID613055Inhibition of rice alpha-glucosidase assessed as production of D-glucose using maltose as substrate after 10 to 30 mins by spectrophotometry2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.
AID342797Inhibition of rat intestinal brush border membrane sucrase2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.
AID33285Concentration that causes 50% inhibition of mammalian alpha-mannosidase was determined in rat epididymis; NI is less than 50 % inhibition at 1000 uM1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID613051Inhibition of bovine liver beta-glucosidase assessed as production of 4-methylumbelliferone using 4-methylumbelliferyl beta-D-glucoside as substrate by spectrophotometry2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.
AID652572Inhibition of recombinant glucosylceramidase 1 using 4-methylumbelliferyl-B-glucoside as substrate by fluorimetric analysis2011ACS medicinal chemistry letters, Jul-14, Volume: 2, Issue:7
Assessment of partially deoxygenated deoxynojirimycin derivatives as glucosylceramide synthase inhibitors.
AID613042Inhibition of jack beans alpha-mannosidase assessed as production of p-nitrophenol at 1000 uM by spectrophotometry2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.
AID40148Concentration that causes 50% inhibition of mammalian lysosomal beta-galactosidase was determined in bovine liver; NI is less than 50 % inhibition at 1000 uM1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID210968Concentration that causes 50% inhibition of mammalian trehalase was determined in rat intestine; NI is less than 50 % inhibition at 1000 uM1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID40438Concentration that causes 50% inhibition of mammalian lysosomal beta-glucosidase was determined in rat liver; NI is less than 50 % inhibition at 1000 uM1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID400357Antihyperglycemic effect on STZ-diabetic ddY mouse assessed as increase in plasma insulin level at 300 umol/kg, ip after 2 hrs by ELISA1998Journal of natural products, Mar, Volume: 61, Issue:3
Antihyperglycemic effects of N-containing sugars from Xanthocercis zambesiaca, Morus bombycis, Aglaonema treubii, and Castanospermum australe in streptozotocin-diabetic mice.
AID613048Inhibition of rat intestinal sucrase assessed as production of p-nitrophenol at by spectrophotometry2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.
AID652571Inhibition of glucosylceramide synthase in mouse RAW cells preincubated for 15 mins followed by substrate addition and measured after 1 hr by fluorescence scanner2011ACS medicinal chemistry letters, Jul-14, Volume: 2, Issue:7
Assessment of partially deoxygenated deoxynojirimycin derivatives as glucosylceramide synthase inhibitors.
AID613044Inhibition of bovine epididymis alpha-L-fucosidase assessed as production of p-nitrophenol at 1000 uM by spectrophotometry2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.
AID342795Inhibition of rat intestinal brush border membrane isomaltase2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.
AID402842Inhibition of rat liver lysosomal beta-glucosidase at 1000 uM by spectrophotometry1997Journal of natural products, Mar, Volume: 60, Issue:3
Fagomine isomers and glycosides from Xanthocercis zambesiaca.
AID613043Inhibition of snail beta-mannosidase assessed as production of p-nitrophenol at 1000 uM by spectrophotometry2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.
AID342793Inhibition of rat intestinal brush border membrane maltase2008Bioorganic & medicinal chemistry, Aug-01, Volume: 16, Issue:15
In vitro inhibition of glycogen-degrading enzymes and glycosidases by six-membered sugar mimics and their evaluation in cell cultures.
AID40171Concentration that causes 50% inhibition of mammalian epididymal beta-galactosidase was determined in rat epididymis; NI is less than 50 % inhibition at 1000 uM1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID40274Concentration that causes 50% inhibition of mammalian lysosomal beta-galactosidase was determined in rat liver; NI is less than 50 % inhibition at 1000 uM1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID613045Inhibition of Penicillium decumbens alpha-L-rhamnosidase assessed as production of p-nitrophenol at 1000 uM by spectrophotometry2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.
AID402836Inhibition of Wistar rat intestinal cellobiase at 1000 uM by glucose B-test1997Journal of natural products, Mar, Volume: 60, Issue:3
Fagomine isomers and glycosides from Xanthocercis zambesiaca.
AID613047Inhibition of rat intestinal isomaltase assessed as production of p-nitrophenol at by spectrophotometry2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.
AID400359Effect on 2.8 mM glucose-induced immunoreactive insulin release in perfused Wistar rat pancreas at 1 mM by radioimmunoassay1998Journal of natural products, Mar, Volume: 61, Issue:3
Antihyperglycemic effects of N-containing sugars from Xanthocercis zambesiaca, Morus bombycis, Aglaonema treubii, and Castanospermum australe in streptozotocin-diabetic mice.
AID652573Inhibition of glucosylceramidase 2 from spleen of patient with gaucher's disease by fluorimetric analysis2011ACS medicinal chemistry letters, Jul-14, Volume: 2, Issue:7
Assessment of partially deoxygenated deoxynojirimycin derivatives as glucosylceramide synthase inhibitors.
AID210963Concentration that causes 50% inhibition of mammalian trehalase was determined in porcine kidney; NI is less than 50 % inhibition at 1000 uM1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID37286Concentration that causes 50% inhibition of mammalian alpha-glucosidase (maltase) was determined in rat intestine1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID613036Inhibition of rat intestinal cellobiase assessed as production of p-nitrophenol at 1000 uM by spectrophotometry2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.
AID402845Inhibition of almond beta-glucosidase at 1000 uM by spectrophotometry1997Journal of natural products, Mar, Volume: 60, Issue:3
Fagomine isomers and glycosides from Xanthocercis zambesiaca.
AID400358Potentiation of 8.3 mM glucose-induced immunoreactive insulin release in perfused Wistar rat pancreas by radioimmunoassay1998Journal of natural products, Mar, Volume: 61, Issue:3
Antihyperglycemic effects of N-containing sugars from Xanthocercis zambesiaca, Morus bombycis, Aglaonema treubii, and Castanospermum australe in streptozotocin-diabetic mice.
AID40144Concentration that causes 50% inhibition of mammalian cytosolic beta-galactosidase was determined in bovine liver1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID613038Inhibition of human lysosome beta-glucosidase assessed as production of 4-methylumbelliferone using 4-methylumbelliferyl beta-D-glucoside as substrate at 1000 uM by spectrophotometry2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.
AID613039Inhibition of coffee beans alpha-galactosidase assessed as production of p-nitrophenol at 1000 uM by spectrophotometry2011Bioorganic & medicinal chemistry, Jun-01, Volume: 19, Issue:11
Docking and SAR studies of D- and L-isofagomine isomers as human β-glucocerebrosidase inhibitors.
AID402837Inhibition of rice alpha-glucosidase by glucose B-test1997Journal of natural products, Mar, Volume: 60, Issue:3
Fagomine isomers and glycosides from Xanthocercis zambesiaca.
AID33278Concentration that causes 50% inhibition of mammalian alpha-mannosidase (golgi II) was determined in rat liver1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID35815Concentration that causes 50% inhibition of soluble mammalian alpha-mannosidase in rat liver; NI is less than 50 % inhibition at 1000 uM1994Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22
Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (45)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's4 (8.89)18.2507
2000's8 (17.78)29.6817
2010's27 (60.00)24.3611
2020's6 (13.33)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 25.84

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 Index25.84 (24.57)
Research Supply Index3.83 (2.92)
Research Growth Index5.00 (4.65)
Search Engine Demand Index29.35 (26.88)
Search Engine Supply Index2.00 (0.95)

This Compound (25.84)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews3 (6.67%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other42 (93.33%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
carbamates
[no description available]		2.0810amino-acid anion
gallic acid
gallate : A trihydroxybenzoate that is the conjugate base of gallic acid.		2.0410trihydroxybenzoic acidantineoplastic agent;
antioxidant;
apoptosis inducer;
astringent;
cyclooxygenase 2 inhibitor;
EC 1.13.11.33 (arachidonate 15-lipoxygenase) inhibitor;
geroprotector;
human xenobiotic metabolite;
plant metabolite
lactic acid
Lactic Acid: A normal intermediate in the fermentation (oxidation, metabolism) of sugar. The concentrated form is used internally to prevent gastrointestinal fermentation. (From Stedman, 26th ed). 2-hydroxypropanoic acid : A 2-hydroxy monocarboxylic acid that is propanoic acid in which one of the alpha-hydrogens is replaced by a hydroxy group.		1.99102-hydroxy monocarboxylic acidalgal metabolite;
Daphnia magna metabolite
glyceraldehyde
Glyceraldehyde: An aldotriose containing the propionaldehyde structure with hydroxy groups at the 2- and 3-positions. It is involved in the formation of ADVANCED GLYCOSYLATION END PRODUCTS.. glyceraldehyde : An aldotriose comprising propanal having hydroxy groups at the 2- and 3-positions. It plays role in the formation of advanced glycation end-products (AGEs), a deleterious accompaniment to ageing.. aldose : Aldehydic parent sugars (polyhydroxy aldehydes H[CH(OH)]nC(=O)H, n >= 2) and their intramolecular hemiacetals.		7.4320aldotriosefundamental metabolite
pipecolic acid
pipecolic acid: RN given refers to cpd without isomeric designation. pipecolic acid : A piperidinemonocarboxylic acid in which the carboxy group is located at position C-2.. pipecolate : A piperidinecarboxylate that is the conjugate base of pipecolic acid.		7.110piperidinemonocarboxylic acid
uric acid
Uric Acid: An oxidation product, via XANTHINE OXIDASE, of oxypurines such as XANTHINE and HYPOXANTHINE. It is the final oxidation product of purine catabolism in humans and primates, whereas in most other mammals URATE OXIDASE further oxidizes it to ALLANTOIN.. uric acid : An oxopurine that is the final oxidation product of purine metabolism.. 6-hydroxy-1H-purine-2,8(7H,9H)-dione : A tautomer of uric acid having oxo groups at C-2 and C-8 and a hydroxy group at C-6.. 7,9-dihydro-1H-purine-2,6,8(3H)-trione : An oxopurine in which the purine ring is substituted by oxo groups at positions 2, 6, and 8.		2.2510uric acidEscherichia coli metabolite;
human metabolite;
mouse metabolite
glyburide
Glyburide: An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide. glyburide : An N-sulfonylurea that is acetohexamide in which the acetyl group is replaced by a 2-(5-chloro-2-methoxybenzamido)ethyl group.		1.9910monochlorobenzenes;
N-sulfonylurea		anti-arrhythmia drug;
EC 2.7.1.33 (pantothenate kinase) inhibitor;
EC 3.6.3.49 (channel-conductance-controlling ATPase) inhibitor;
hypoglycemic agent
sucrose
Saccharum: A plant genus of the family POACEAE widely cultivated in the tropics for the sweet cane that is processed into sugar.		9.1830glycosyl glycosidealgal metabolite;
Escherichia coli metabolite;
human metabolite;
mouse metabolite;
osmolyte;
Saccharomyces cerevisiae metabolite;
sweetening agent
adenosine diphosphate
Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.		1.9910adenosine 5'-phosphate;
purine ribonucleoside 5'-diphosphate		fundamental metabolite;
human metabolite
galactose
galactopyranose : The pyranose form of galactose.		2.0510D-galactose;
galactopyranose		Escherichia coli metabolite;
mouse metabolite
piperidine
[no description available]		2.0810azacycloalkane;
piperidines;
saturated organic heteromonocyclic parent;
secondary amine		base;
catalyst;
human metabolite;
non-polar solvent;
plant metabolite;
protic solvent;
reagent
quinazolines
Quinazolines: A group of aromatic heterocyclic compounds that contain a bicyclic structure with two fused six-membered aromatic rings, a benzene ring and a pyrimidine ring.. quinazoline : A mancude organic heterobicyclic parent that is naphthalene in which the carbon atoms at positions 1 and 3 have been replaced by nitrogen atoms.. quinazolines : Any organic heterobicyclic compound based on a quinazoline skeleton and its substituted derivatives.		2.0610azaarene;
mancude organic heterobicyclic parent;
ortho-fused heteroarene;
quinazolines
hydrazine
diamine : Any polyamine that contains two amino groups.		2.0510azane;
hydrazines		EC 4.3.1.10 (serine-sulfate ammonia-lyase) inhibitor
vasicinone
vasicinone: isolated from Adhatoda vasica; structure given in first source		2.0610
malondialdehyde
Malondialdehyde: The dialdehyde of malonic acid.. malonaldehyde : A dialdehyde that is propane substituted by two oxo groups at the terminal carbon atoms respectively. A biomarker of oxidative damage to lipids caused by smoking, it exists in vivo mainly in the enol form.		2.1710dialdehydebiomarker
fucose
Fucose: A six-member ring deoxysugar with the chemical formula C6H12O5. It lacks a hydroxyl group on the carbon at position 6 of the molecule.. L-fucopyranose : The pyranose form of L-fucose.. fucose : Any deoxygalactose that is deoxygenated at the 6-position.		2.0810fucopyranose;
L-fucose		Escherichia coli metabolite;
mouse metabolite
1-deoxynojirimycin
1-deoxy-nojirimycin: structure in first source. duvoglustat : An optically active form of 2-(hydroxymethyl)piperidine-3,4,5-triol having 2R,3R,4R,5S-configuration.		10.011202-(hydroxymethyl)piperidine-3,4,5-triol;
piperidine alkaloid		anti-HIV agent;
anti-obesity agent;
bacterial metabolite;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
hepatoprotective agent;
hypoglycemic agent;
plant metabolite
miglustat
miglustat: a glucosylceramide synthase inhibitor. miglustat : A hydroxypiperidine that is deoxynojirimycin in which the amino hydrogen is replaced by a butyl group.		2.0610piperidines;
tertiary amino compound		anti-HIV agent;
EC 2.4.1.80 (ceramide glucosyltransferase) inhibitor
castanospermine
castanospermine: indolizidine alkaloid from seeds of Australian legume, Castanospermum australe. castanospermine : A tetrahydroxyindolizidine alkaloid that consists of octahydroindolizine having four hydroxy substituents located at positions 1, 6, 7 and 8 (the 1S,6S,7R,8R,8aR-diastereomer).		1.9910indolizidine alkaloidanti-HIV-1 agent;
anti-inflammatory agent;
EC 3.2.1.* (glycosidase) inhibitor;
metabolite
glucose, (beta-d)-isomer
beta-D-glucose : D-Glucopyranose with beta configuration at the anomeric centre.. (1->4)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->4) linkages.. (1->3)-beta-D-glucan : A beta-D-glucan in which the glucose units are connected by (1->3) linkages.		2.730D-glucopyranoseepitope;
mouse metabolite
nojirimycin
nojirimycin: from Streptomyces ficellus; RN given refers to parent cpd without isomeric designation		7.0210amino monosaccharide;
hydroxypiperidine
2,3-trimethylene-4-quinazolone
2,3-trimethylene-4-quinazolone: structure in first source		2.0610quinazolines
fructose-6-phosphate
fructose-6-phosphate: RN given refers to parent cpd with unspecified isomeric designation. fructose 6-phosphate : A ketohexose monophosphate consisting of fructose having a phosphate group located at the 6-position.		7.3110D-fructose 6-phosphate
4-nitrophenyl-alpha-l-fucoside
4-nitrophenylfucoside: RN given refers to (alpha-L-isomer). 4-nitrophenyl alpha-L-fucoside : An alpha-L-fucoside that is alpha-L-fucopyranose in which the anomeric hydroxy hydrogen is replaced by a 4-nitrophenyl group.		2.0510alpha-L-fucoside;
C-nitro compound		chromogenic compound
4-nitrophenyl alpha-glucoside
4-nitrophenyl alpha-glucoside: RN given refers to (alpha)-anomer; see also (beta)-anomers: 29857-05-4, 2492-87-7; cpd with unspecified anomer: 5779-46-4. 4-nitrophenyl alpha-D-glucoside : An alpha-D-glucoside that is beta-D-glucopyranose in which the anomeric hydroxy hydrogen is replaced by a 4-nitrophenyl group.		2.0510alpha-D-glucoside;
C-nitro compound;
monosaccharide derivative		chromogenic compound
cobalt
Cobalt: A trace element that is a component of vitamin B12. It has the atomic symbol Co, atomic number 27, and atomic weight 58.93. It is used in nuclear weapons, alloys, and pigments. Deficiency in animals leads to anemia; its excess in humans can lead to erythrocytosis.. cobalt(1+) : A monovalent inorganic cation obtained from cobalt.. cobalt atom : A cobalt group element atom that has atomic number 27.		2.3110cobalt group element atom;
metal allergen		micronutrient
2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine
2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine: structure given in first source		2.3920dihydroxypyrrolidine
1,4-dideoxy-1,4-iminoarabinitol
1,4-dideoxy-1,4-iminoarabinitol: RN given refers to (2S-(2alpha,3beta,4alpha))-isomer; structure given in first source		2.1110
homonojirimycin
homonojirimycin: inhibits alpha-glucosidase; RN given for (2R-(2alpha,3alpha,4beta,5alpha,6beta))-isomer; structure in first source		2.4220
valiolamine
valiolamine: isolated from Streptomyces hygroscopicus; RN from CA Index; RN not in Chemline 2/85		2.0410
migalastat
migalastat: a potent inhibitor of glycolipid biosynthesis		2.0810piperidines
glyceraldehyde 3-phosphate
Glyceraldehyde 3-Phosphate: An aldotriose which is an important intermediate in glycolysis and in tryptophan biosynthesis.. glyceraldehyde 3-phosphate : An aldotriose phosphate that is the 3-phospho derivative of glyceraldehyde. It is an important metabolic intermediate in several central metabolic pathways in all organisms.		1.9910glyceraldehyde 3-phosphatemouse metabolite
arabinose
[no description available]		2.1110L-arabinoseEscherichia coli metabolite;
mouse metabolite
glucosamine
D-glucosamine : An amino sugar whose structure comprises D-glucose having an amino substituent at position 2.. 2-amino-2-deoxy-D-glucopyranose : A D-glucosamine whose structure comprises D-glucopyranose having an amino substituent at position 2.		2.0210D-glucosamineEscherichia coli metabolite;
geroprotector;
mouse metabolite
miglitol
[no description available]		2.0410piperidines
ao 128
AO 128: alpha-glucosidase inhibitor; structure given in first source		2.0410organic molecular entity
acarbose
[no description available]		2.0410amino cyclitol;
glycoside
acetyl coenzyme a
Acetyl Coenzyme A: Acetyl CoA participates in the biosynthesis of fatty acids and sterols, in the oxidation of fatty acids and in the metabolism of many amino acids. It also acts as a biological acetylating agent.		1.9910acyl-CoAacyl donor;
coenzyme;
effector;
fundamental metabolite
eicosapentaenoic acid
icosapentaenoic acid : Any straight-chain, C20 polyunsaturated fatty acid having five C=C double bonds.. all-cis-5,8,11,14,17-icosapentaenoic acid : An icosapentaenoic acid having five cis-double bonds at positions 5, 8, 11, 14 and 17.		3.3510icosapentaenoic acid;
omega-3 fatty acid		anticholesteremic drug;
antidepressant;
antineoplastic agent;
Daphnia galeata metabolite;
fungal metabolite;
micronutrient;
mouse metabolite;
nutraceutical
isofagomine
[no description available]		7.7730piperidines
1,4-dideoxy-1,4-imino-d-arabinitol
[no description available]		2.0410
glycosides
[no description available]		7.4420
vasicine
vasicine: RN given refers to (R)-isomer		2.0610
leukotriene b4
Leukotriene B4: The major metabolite in neutrophil polymorphonuclear leukocytes. It stimulates polymorphonuclear cell function (degranulation, formation of oxygen-centered free radicals, arachidonic acid release, and metabolism). (From Dictionary of Prostaglandins and Related Compounds, 1990). leukotriene B4 : A leukotriene composed of (6Z,8E,10E,14Z)-icosatetraenoic acid having (5S)- and (12R)-hydroxy substituents. It is a lipid mediator of inflammation that is generated from arachidonic acid via the 5-lipoxygenase pathway.		2.4110dihydroxy monocarboxylic acid;
hydroxy polyunsaturated fatty acid;
leukotriene;
long-chain fatty acid		human metabolite;
mouse metabolite;
plant metabolite;
vasoconstrictor agent
rutin
Hydroxyethylrutoside: Monohydroxyethyl derivative of rutin. Peripheral circulation stimulant used in treatment of venous disorders.		2.0410disaccharide derivative;
quercetin O-glucoside;
rutinoside;
tetrahydroxyflavone		antioxidant;
metabolite
kaempferol
[no description available]		2.03107-hydroxyflavonol;
flavonols;
tetrahydroxyflavone		antibacterial agent;
geroprotector;
human blood serum metabolite;
human urinary metabolite;
human xenobiotic metabolite;
plant metabolite
harmine
Harmine: Alkaloid isolated from seeds of PEGANUM HARMALA; ZYGOPHYLLACEAE. It is identical to banisterine, or telepathine, from Banisteria caapi and is one of the active ingredients of hallucinogenic drinks made in the western Amazon region from related plants. It has no therapeutic use, but (as banisterine) was hailed as a cure for postencephalitic PARKINSON DISEASE in the 1920's.. harmine : A harmala alkaloid in which the harman skeleton is methoxy-substituted at C-7.		2.0610harmala alkaloidanti-HIV agent;
EC 1.4.3.4 (monoamine oxidase) inhibitor;
metabolite
salacinol
salacinol: a sulfated thiosugar from Salacia reticulata (CELASTRACEAE); structure in first source		3.3510
n-(5-adamantane-1-yl-methoxy-pentyl)deoxynojirimycin
[no description available]		2.0610
3-epi-fagomine
3-epi-fagomine : A member of the class of hydroxypiperidines that is piperidine carrying a hydroxymethyl substituent at position 2 as well as two hydroxy substituents at positions 3 and 4 (the 2R,3R,4S-diastereomer).		3.1150amino monosaccharide;
hydroxypiperidine;
primary alcohol;
secondary alcohol;
secondary amino compound;
triol		EC 3.2.1.10 (oligo-1,6-glucosidase) inhibitor;
EC 3.2.1.23 (beta-galactosidase) inhibitor;
plant metabolite
1-azafagomine
1-azafagomine: inhibits processing glycosidase; structure in first source		710
sepharose
agarose : A linear polysaccharide made up from alternating D-galactose and 3,6-anhydro-alpha-L-galactopyranose residues joined by alpha-(1->3)- and beta-(1->4)-linkages.		2.3110
piperidines
Piperidines: A family of hexahydropyridines.		3.6390
leptin
Leptin: A 16-kDa peptide hormone secreted from WHITE ADIPOCYTES. Leptin serves as a feedback signal from fat cells to the CENTRAL NERVOUS SYSTEM in regulation of food intake, energy balance, and fat storage.		2.8730
ConditionIndicatedRelationship StrengthStudiesTrials
Alloxan Diabetes
[description not available]		01.9910
Acid beta-Glucosidase Deficiency
[description not available]		02.4820
Gaucher Disease
An autosomal recessive disorder caused by a deficiency of acid beta-glucosidase (GLUCOSYLCERAMIDASE) leading to intralysosomal accumulation of glycosylceramide mainly in cells of the MONONUCLEAR PHAGOCYTE SYSTEM. The characteristic Gaucher cells, glycosphingolipid-filled HISTIOCYTES, displace normal cells in BONE MARROW and visceral organs causing skeletal deterioration, hepatosplenomegaly, and organ dysfunction. There are several subtypes based on the presence and severity of neurological involvement.		02.4820
Body Weight
The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.		08.2650
Innate Inflammatory Response
[description not available]		02.6620
Inflammation
A pathological process characterized by injury or destruction of tissues caused by a variety of cytologic and chemical reactions. It is usually manifested by typical signs of pain, heat, redness, swelling, and loss of function.		02.6620
Fatty Liver, Nonalcoholic
[description not available]		02.2510
Blood Pressure, High
[description not available]		02.2510
Hypertension
Persistently high systemic arterial BLOOD PRESSURE. Based on multiple readings (BLOOD PRESSURE DETERMINATION), hypertension is currently defined as when SYSTOLIC PRESSURE is consistently greater than 140 mm Hg or when DIASTOLIC PRESSURE is consistently 90 mm Hg or more.		07.2510
Non-alcoholic Fatty Liver Disease
Fatty liver finding without excessive ALCOHOL CONSUMPTION.		02.2510
Prediabetes
[description not available]		07.5920
Prediabetic State
The time period before the development of symptomatic diabetes. For example, certain risk factors can be observed in subjects who subsequently develop INSULIN RESISTANCE as in type 2 diabetes (DIABETES MELLITUS, TYPE 2).		02.5920
Sensitivity and Specificity
Binary classification measures to assess test results. Sensitivity or recall rate is the proportion of true positives. Specificity is the probability of correctly determining the absence of a condition. (From Last, Dictionary of Epidemiology, 2d ed)		02.5220
Diabetes Mellitus, Adult-Onset
[description not available]		0310
Diabetes Mellitus, Type 2
A subclass of DIABETES MELLITUS that is not INSULIN-responsive or dependent (NIDDM). It is characterized initially by INSULIN RESISTANCE and HYPERINSULINEMIA; and eventually by GLUCOSE INTOLERANCE; HYPERGLYCEMIA; and overt diabetes. Type II diabetes mellitus is no longer considered a disease exclusively found in adults. Patients seldom develop KETOSIS but often exhibit OBESITY.		0310
Disease Models, Animal
Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.		02.110
Obesity
A status with BODY WEIGHT that is grossly above the recommended standards, usually due to accumulation of excess FATS in the body. The standards may vary with age, sex, genetic or cultural background. In the BODY MASS INDEX, a BMI greater than 30.0 kg/m2 is considered obese, and a BMI greater than 40.0 kg/m2 is considered morbidly obese (MORBID OBESITY).		05.2860
Weight Gain
Increase in BODY WEIGHT over existing weight.		07.110
Classic Globoid Cell Leukodystrophy
[description not available]		02.1310
Leukodystrophy, Globoid Cell
An autosomal recessive metabolic disorder caused by a deficiency of GALACTOSYLCERAMIDASE leading to intralysosomal accumulation of galactolipids such as GALACTOSYLCERAMIDES and PSYCHOSINE. It is characterized by demyelination associated with large multinucleated globoid cells, predominantly involving the white matter of the central nervous system. The loss of MYELIN disrupts normal conduction of nerve impulses.		02.1310
Insulin Sensitivity
[description not available]		04.9340
Insulin Resistance
Diminished effectiveness of INSULIN in lowering blood sugar levels: requiring the use of 200 units or more of insulin per day to prevent HYPERGLYCEMIA or KETOSIS.		04.9340