2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine profile

2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine: structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	124702
CHEMBL ID	312653
CHEBI ID	4289
SCHEMBL ID	466574
MeSH ID	M0127052

Synonym
CHEMBL312653 ,
chebi:4289 ,
2r,5r-dihydroxymethyl-3r,4r-dihydroxypyrrolidine
bdbm50031481
(2r,3r,4r,5r)-2,5-bis-hydroxymethyl-pyrrolidine-3,4-diol
DQQ ,
2,5-pyrrolidinedimethanol, 3,4-dihydroxy-, (2r,3r,4r,5r)-
2,5-dideoxy-2,5-imino-d-mannitol
(2r,3r,4r,5r)-2,5-bis(hydroxymethyl)pyrrolidine-3,4-diol
2(r),5(r)-bis(hydroxymethyl)-3(r),4(r)-dihydroxypyrrolidine
nsc624987
nsc613239
2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine
dmdp
59920-31-9
9D7F3C44-69AD-44CB-89DE-8A2E1A4AE7D1
AKOS006280967
2,5-dihydroxymethyl-3,4-dihydroxy-pyrrolidine
d-mannitol, 2,5-dideoxy-2,5-imino-, (6r-(6alpha,7alpha,7(r*)))-
nsc 624987
2,5-imino-2,5-dideoxy-d-mannitol
SCHEMBL466574
2,5-bis(hydroxymethyl)-3,4-dihydroxypyrrolidine
W-203234
210115-92-7
DTXSID50943312
Q27106325
PD119439
CS-0650793
HY-N11598
di(hydroxymethyl)dihydroxypyrrolidine (dmdp)

Class	Description
dihydroxypyrrolidine
[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	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Trehalase	Sus scrofa (pig)	IC50 (µMol)	350.0000	2.5000	2.5000	2.5000	AID338569; AID400773
Maltase-glucoamylase, intestinal	Homo sapiens (human)	IC50 (µMol)	50.0000	0.0400	3.4652	9.0000	AID104668
Alpha-glucosidase MAL62	Saccharomyces cerevisiae (brewer's yeast)	IC50 (µMol)	2.0000	0.8400	1.4200	2.0000	AID338567
Sucrase-isomaltase, intestinal	Rattus norvegicus (Norway rat)	IC50 (µMol)	111.6667	0.0400	1.8483	10.0000	AID208985; AID324678; AID324679; AID324680; AID400757; AID91639
Glycogen debranching enzyme	Homo sapiens (human)	IC50 (µMol)	9.8000	8.4000	9.5143	10.0000	AID324673
Lactase-phlorizin hydrolase	Rattus norvegicus (Norway rat)	IC50 (µMol)	3.6000	0.1200	2.9867	4.4000	AID400767; AID99232
Lysosomal alpha-glucosidase	Rattus norvegicus (Norway rat)	IC50 (µMol)	191.0000	0.0800	2.5061	9.8500	AID400755; AID400761
Non-lysosomal glucosylceramidase	Homo sapiens (human)	IC50 (µMol)	150.0000	0.0003	0.0897	0.3000	AID324686
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
maltose catabolic process	Maltase-glucoamylase, intestinal	Homo sapiens (human)
starch catabolic process	Maltase-glucoamylase, intestinal	Homo sapiens (human)
dextrin catabolic process	Maltase-glucoamylase, intestinal	Homo sapiens (human)
glycogen biosynthetic process	Glycogen debranching enzyme	Homo sapiens (human)
glycogen catabolic process	Glycogen debranching enzyme	Homo sapiens (human)
response to nutrient	Glycogen debranching enzyme	Homo sapiens (human)
response to glucocorticoid	Glycogen debranching enzyme	Homo sapiens (human)
carbohydrate metabolic process	Non-lysosomal glucosylceramidase	Homo sapiens (human)
glucosylceramide catabolic process	Non-lysosomal glucosylceramidase	Homo sapiens (human)
cholesterol metabolic process	Non-lysosomal glucosylceramidase	Homo sapiens (human)
bile acid metabolic process	Non-lysosomal glucosylceramidase	Homo sapiens (human)
glycoside catabolic process	Non-lysosomal glucosylceramidase	Homo sapiens (human)
central nervous system neuron development	Non-lysosomal glucosylceramidase	Homo sapiens (human)
lipid glycosylation	Non-lysosomal glucosylceramidase	Homo sapiens (human)
regulation of actin filament polymerization	Non-lysosomal glucosylceramidase	Homo sapiens (human)
regulation of microtubule polymerization	Non-lysosomal glucosylceramidase	Homo sapiens (human)
glycosphingolipid catabolic process	Non-lysosomal glucosylceramidase	Homo sapiens (human)
regulation of membrane lipid distribution	Non-lysosomal glucosylceramidase	Homo sapiens (human)
central nervous system development	Non-lysosomal glucosylceramidase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
catalytic activity	Maltase-glucoamylase, intestinal	Homo sapiens (human)
glucan 1,4-alpha-glucosidase activity	Maltase-glucoamylase, intestinal	Homo sapiens (human)
alpha-1,4-glucosidase activity	Maltase-glucoamylase, intestinal	Homo sapiens (human)
protein binding	Maltase-glucoamylase, intestinal	Homo sapiens (human)
amylase activity	Maltase-glucoamylase, intestinal	Homo sapiens (human)
carbohydrate binding	Maltase-glucoamylase, intestinal	Homo sapiens (human)
maltose alpha-glucosidase activity	Maltase-glucoamylase, intestinal	Homo sapiens (human)
glycogen debranching enzyme activity	Glycogen debranching enzyme	Homo sapiens (human)
4-alpha-glucanotransferase activity	Glycogen debranching enzyme	Homo sapiens (human)
amylo-alpha-1,6-glucosidase activity	Glycogen debranching enzyme	Homo sapiens (human)
protein binding	Glycogen debranching enzyme	Homo sapiens (human)
polysaccharide binding	Glycogen debranching enzyme	Homo sapiens (human)
polyubiquitin modification-dependent protein binding	Glycogen debranching enzyme	Homo sapiens (human)
beta-maltose 4-alpha-glucanotransferase activity	Glycogen debranching enzyme	Homo sapiens (human)
galactosylceramidase activity	Non-lysosomal glucosylceramidase	Homo sapiens (human)
glucosylceramidase activity	Non-lysosomal glucosylceramidase	Homo sapiens (human)
beta-glucosidase activity	Non-lysosomal glucosylceramidase	Homo sapiens (human)
glucosyltransferase activity	Non-lysosomal glucosylceramidase	Homo sapiens (human)
steryl-beta-glucosidase activity	Non-lysosomal glucosylceramidase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
plasma membrane	Maltase-glucoamylase, intestinal	Homo sapiens (human)
apical plasma membrane	Maltase-glucoamylase, intestinal	Homo sapiens (human)
extracellular exosome	Maltase-glucoamylase, intestinal	Homo sapiens (human)
tertiary granule membrane	Maltase-glucoamylase, intestinal	Homo sapiens (human)
ficolin-1-rich granule membrane	Maltase-glucoamylase, intestinal	Homo sapiens (human)
extracellular region	Glycogen debranching enzyme	Homo sapiens (human)
nucleus	Glycogen debranching enzyme	Homo sapiens (human)
cytoplasm	Glycogen debranching enzyme	Homo sapiens (human)
cytosol	Glycogen debranching enzyme	Homo sapiens (human)
inclusion body	Glycogen debranching enzyme	Homo sapiens (human)
sarcoplasmic reticulum	Glycogen debranching enzyme	Homo sapiens (human)
secretory granule lumen	Glycogen debranching enzyme	Homo sapiens (human)
ficolin-1-rich granule lumen	Glycogen debranching enzyme	Homo sapiens (human)
isoamylase complex	Glycogen debranching enzyme	Homo sapiens (human)
Golgi membrane	Non-lysosomal glucosylceramidase	Homo sapiens (human)
endoplasmic reticulum membrane	Non-lysosomal glucosylceramidase	Homo sapiens (human)
smooth endoplasmic reticulum	Non-lysosomal glucosylceramidase	Homo sapiens (human)
cytosol	Non-lysosomal glucosylceramidase	Homo sapiens (human)
plasma membrane	Non-lysosomal glucosylceramidase	Homo sapiens (human)
membrane	Non-lysosomal glucosylceramidase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (73)

Assay ID	Title	Year	Journal	Article
AID33285	Concentration that causes 50% inhibition of mammalian alpha-mannosidase was determined in rat epididymis; NI is less than 50 % inhibition at 1000 uM	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID105142	Concentration giving 50% inhibition of HIV-1 induced cytopathogenicity in MT-4 cells	1995	Journal of medicinal chemistry, Jun-23, Volume: 38, Issue:13	N-alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication.
AID324686	Inhibition of human lysosomal beta glucosidase	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Effect of five-membered sugar mimics on mammalian glycogen-degrading enzymes and various glucosidases.
AID1329707	Inhibition of yeast alpha-glucosidase using p-nitrophenyl-glycoside as substrate by spectrophotometric method	2017	Bioorganic & medicinal chemistry, 01-01, Volume: 25, Issue:1	Strategy for designing selective α-l-rhamnosidase inhibitors: Synthesis and biological evaluation of l-DMDP cyclic isothioureas.
AID37287	Concentration that causes 50% inhibition of mammalian alpha-glucosidase (maltase) was determined in rat intestine; NI is less than 50 % inhibition at 1000 uM	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID91639	Inhibition of Glycosidases (isomaltase)in rat intestinal brush border membranes by D-glucose oxidase-peroxidase method	1995	Journal of medicinal chemistry, Jun-23, Volume: 38, Issue:13	N-alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication.
AID324673	Inhibition of amylo-1,6-glucosidase	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Effect of five-membered sugar mimics on mammalian glycogen-degrading enzymes and various glucosidases.
AID35369	Inhibition of lysosomal Alpha-mannosidase II in rat liver	1995	Journal of medicinal chemistry, Jun-23, Volume: 38, Issue:13	N-alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication.
AID40435	Concentration that causes 50% inhibition of mammalian cellobiase beta-glucosidase was determined in rat intestine	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID324680	Inhibition of rat sucrase	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Effect of five-membered sugar mimics on mammalian glycogen-degrading enzymes and various glucosidases.
AID400760	Inhibition of Wistar rat intestinal sucrase at 1000 uM	1998	Journal of natural products, May, Volume: 61, Issue:5	Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.
AID400361	Antihyperglycemic effect in STZ-diabetic ddY mouse assessed as reduction in blood glucose level at 150 umol/kg, ip after 4 hrs by glucose oxidase method	1998	Journal 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.
AID400757	Inhibition of Wistar rat intestinal isomaltase	1998	Journal of natural products, May, Volume: 61, Issue:5	Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.
AID52058	Inhibition of Cellobiase in rat intestinal brush border membranes by D-glucose oxidase-peroxidase method	1995	Journal of medicinal chemistry, Jun-23, Volume: 38, Issue:13	N-alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication.
AID40438	Concentration that causes 50% inhibition of mammalian lysosomal beta-glucosidase was determined in rat liver; NI is less than 50 % inhibition at 1000 uM	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID1329722	Inhibition of Aspergillus niger amyloglucosidase assessed as D-glucose level using maltose as substrate measured after 10 to 30 mins	2017	Bioorganic & medicinal chemistry, 01-01, Volume: 25, Issue:1	Strategy for designing selective α-l-rhamnosidase inhibitors: Synthesis and biological evaluation of l-DMDP cyclic isothioureas.
AID36815	Concentration that causes 50% inhibition of mammalian alpha-L-fucosidase was determined in bovine epididymis; NI is less than 50 % inhibition at 1000 uM	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID37272	Inhibition of mammalian alpha-glucosidase (lysosomal) was determined in bovine liver	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID37437	Concentration that causes 50% inhibition of mammalian alpha-glucosidase (endoplasmic reticulum glucosidase II) was determined in rat liver; NI is less than 50 % inhibition at 1000 uM	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID335082	Inhibition of yeast alpha-glucosidase	1993	Journal of natural products, Aug, Volume: 56, Issue:8	2-Hydroxymethyl-3,4-dihydroxy-6-methyl-pyrrolidine (6-deoxy-DMDP), an alkaloid beta-mannosidase inhibitor from seeds of Angylocalyx pynaertii.
AID400771	Inhibition of almond beta-glucosidase	1998	Journal of natural products, May, Volume: 61, Issue:5	Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.
AID37284	Concentration that causes 50% inhibition of mammalian alpha-glucosidase (lysosomal) was determined in rat liver	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID210966	Concentration that causes 50% inhibition of mammalian trehalase was determined in rat intestine	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID1329709	Inhibition of almond beta-glucosidase using p-nitrophenyl-glycoside as substrate by spectrophotometric method	2017	Bioorganic & medicinal chemistry, 01-01, Volume: 25, Issue:1	Strategy for designing selective α-l-rhamnosidase inhibitors: Synthesis and biological evaluation of l-DMDP cyclic isothioureas.
AID400769	Inhibition of bovine epididymis alpha-L-fucosidase	1998	Journal of natural products, May, Volume: 61, Issue:5	Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.
AID36808	Inhibition of endoplasmic reticulum Alpha-Glucosidase II in rat liver	1995	Journal of medicinal chemistry, Jun-23, Volume: 38, Issue:13	N-alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication.
AID400753	Inhibition of rice alpha-glucosidase	1998	Journal of natural products, May, Volume: 61, Issue:5	Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.
AID324672	Inhibition of rabbit muscle glycogen phosphorylase b at 400 uM	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Effect of five-membered sugar mimics on mammalian glycogen-degrading enzymes and various glucosidases.
AID208985	Inhibition of Sucrase in rat intestinal brush border membranes by D-glucose oxidase-peroxidase method	1995	Journal of medicinal chemistry, Jun-23, Volume: 38, Issue:13	N-alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication.
AID400773	Inhibition of pig kidney alpha alpha-trehalase	1998	Journal of natural products, May, Volume: 61, Issue:5	Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.
AID400767	Inhibition of Wistar rat intestinal lactase	1998	Journal of natural products, May, Volume: 61, Issue:5	Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.
AID40148	Concentration that causes 50% inhibition of mammalian lysosomal beta-galactosidase was determined in bovine liver; NI is less than 50 % inhibition at 1000 uM	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID40144	Concentration that causes 50% inhibition of mammalian cytosolic beta-galactosidase was determined in bovine liver	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID324676	Inhibition of rice alpha-glucosidase	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Effect of five-membered sugar mimics on mammalian glycogen-degrading enzymes and various glucosidases.
AID40171	Concentration that causes 50% inhibition of mammalian epididymal beta-galactosidase was determined in rat epididymis; NI is less than 50 % inhibition at 1000 uM	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID400775	Inhibition of Wistar rat intestinal alpha alpha-trehalase	1998	Journal of natural products, May, Volume: 61, Issue:5	Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.
AID1329712	Inhibition of bovine liver beta-glucosidase using p-nitrophenyl-glycoside as substrate by spectrophotometric method	2017	Bioorganic & medicinal chemistry, 01-01, Volume: 25, Issue:1	Strategy for designing selective α-l-rhamnosidase inhibitors: Synthesis and biological evaluation of l-DMDP cyclic isothioureas.
AID104771	Concentration giving 50% inhibition of growth of mock-infected MT-4 cells	1995	Journal of medicinal chemistry, Jun-23, Volume: 38, Issue:13	N-alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication.
AID335083	Inhibition of almonds beta-glucosidase	1993	Journal of natural products, Aug, Volume: 56, Issue:8	2-Hydroxymethyl-3,4-dihydroxy-6-methyl-pyrrolidine (6-deoxy-DMDP), an alkaloid beta-mannosidase inhibitor from seeds of Angylocalyx pynaertii.
AID338567	Inhibition of yeast maltase alpha-glucosidase assessed as p-nitrophenol release by spectrophotometrically	2002	Journal of natural products, Feb, Volume: 65, Issue:2	New sugar-mimic alkaloids from the pods of Angylocalyx pynaertii.
AID105266	Concentration giving 50% inhibition of growth of mock-infected MOLT-4 cells	1995	Journal of medicinal chemistry, Jun-23, Volume: 38, Issue:13	N-alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication.
AID210969	Inhibition of Glycosidases (trehalase)in rat intestinal brush border membranes by D-glucose oxidase-peroxidase method	1995	Journal of medicinal chemistry, Jun-23, Volume: 38, Issue:13	N-alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication.
AID36809	Inhibition of lysosomal Alpha-Glucosidase II in rat liver	1995	Journal of medicinal chemistry, Jun-23, Volume: 38, Issue:13	N-alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication.
AID35370	Inhibition of soluble Alpha-mannosidase II in rat liver	1995	Journal of medicinal chemistry, Jun-23, Volume: 38, Issue:13	N-alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication.
AID1329717	Inhibition of coffee bean alpha-galactosidase at 1000 uM using p-nitrophenyl-glycoside as substrate by spectrophotometric method	2017	Bioorganic & medicinal chemistry, 01-01, Volume: 25, Issue:1	Strategy for designing selective α-l-rhamnosidase inhibitors: Synthesis and biological evaluation of l-DMDP cyclic isothioureas.
AID489424	Inhibition of Agrobacterium sp. beta-glucosidase	2010	Bioorganic & medicinal chemistry letters, Jul-15, Volume: 20, Issue:14	Synthesis and biological evaluation of novel biotin-iminoalditol conjugates.
AID1329719	Inhibition of Jack bean alpha-mannosidase at 1000 uM preincubated for 45 mins followed by addition of p-nitrophenyl-glycoside as substrate measured after 30 mins by fluorescence spectrophometry	2017	Bioorganic & medicinal chemistry, 01-01, Volume: 25, Issue:1	Strategy for designing selective α-l-rhamnosidase inhibitors: Synthesis and biological evaluation of l-DMDP cyclic isothioureas.
AID104668	Inhibition of Glycosidases (maltase) in rat intestinal brush border membranes by D-glucose oxidase-peroxidase method maltase	1995	Journal of medicinal chemistry, Jun-23, Volume: 38, Issue:13	N-alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication.
AID99232	Inhibition of Glycosidases (lactase)in rat intestinal brush border membranes by D-glucose oxidase-peroxidase method	1995	Journal of medicinal chemistry, Jun-23, Volume: 38, Issue:13	N-alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication.
AID338568	Inhibition of yeast isomaltase alpha-glucosidase assessed as p-nitrophenol release by spectrophotometrically	2002	Journal of natural products, Feb, Volume: 65, Issue:2	New sugar-mimic alkaloids from the pods of Angylocalyx pynaertii.
AID400755	Inhibition of Wistar rat intestinal maltase	1998	Journal of natural products, May, Volume: 61, Issue:5	Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.
AID338569	Inhibition of pig kidney trehalase assessed as p-nitrophenol release by spectrophotometrically	2002	Journal of natural products, Feb, Volume: 65, Issue:2	New sugar-mimic alkaloids from the pods of Angylocalyx pynaertii.
AID1329715	Inhibition of human lysosomal beta-glucosidase at 1000 uM using 4-methylumbelliferyl-beta-D-glucopyranoside as substrate preincubated for 45 mins followed by substrate addition measured after 30 mins by fluorescence spectrophotometric method	2017	Bioorganic & medicinal chemistry, 01-01, Volume: 25, Issue:1	Strategy for designing selective α-l-rhamnosidase inhibitors: Synthesis and biological evaluation of l-DMDP cyclic isothioureas.
AID400761	Inhibition of Wistar rat liver lysosomal alpha-glucosidase	1998	Journal of natural products, May, Volume: 61, Issue:5	Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.
AID400763	Inhibition of Caldocellum saccharolyticum beta-glucosidase	1998	Journal of natural products, May, Volume: 61, Issue:5	Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.
AID33280	Concentration that causes 50% inhibition of mammalian alpha-mannosidase (golgi II) was determined in rat liver; NI is less than 50 % inhibition at 1000 uM	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID1329718	Inhibition of Escherichia coli beta-galactosidase at 1000 uM using p-nitrophenyl-glycoside as substrate by spectrophotometric method	2017	Bioorganic & medicinal chemistry, 01-01, Volume: 25, Issue:1	Strategy for designing selective α-l-rhamnosidase inhibitors: Synthesis and biological evaluation of l-DMDP cyclic isothioureas.
AID400772	Inhibition of yeast alpha-glucosidase	1998	Journal of natural products, May, Volume: 61, Issue:5	Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.
AID35815	Concentration that causes 50% inhibition of soluble mammalian alpha-mannosidase in rat liver; NI is less than 50 % inhibition at 1000 uM	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID33282	Concentration that causes 50% inhibition of mammalian alpha-mannosidase (lysosomal) was determined in rat liver; NI is less than 50 % inhibition at 1000 uM	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID35262	Inhibition of golgi Alpha-mannosidase II in rat liver	1995	Journal of medicinal chemistry, Jun-23, Volume: 38, Issue:13	N-alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication.
AID1329720	Inhibition of Helix pomatia beta-mannosidase using p-nitrophenyl-glycoside as substrate by spectrophotometric method	2017	Bioorganic & medicinal chemistry, 01-01, Volume: 25, Issue:1	Strategy for designing selective α-l-rhamnosidase inhibitors: Synthesis and biological evaluation of l-DMDP cyclic isothioureas.
AID40176	Concentration that causes 50% inhibition of mammalian lactase beta-galactosidase was determined in rat intestine	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID400765	Inhibition of bovine liver beta-galactosidase	1998	Journal of natural products, May, Volume: 61, Issue:5	Nitrogen-containing furanose and pyranose analogues from Hyacinthus orientalis.
AID324678	Inhibition of rat intestinal maltase	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Effect of five-membered sugar mimics on mammalian glycogen-degrading enzymes and various glucosidases.
AID1329704	Inhibition of Penicillium decumbens alpha-L-rhamnosidase at 1000 uM using p-nitrophenyl-glycoside as substrate by spectrophotometric method	2017	Bioorganic & medicinal chemistry, 01-01, Volume: 25, Issue:1	Strategy for designing selective α-l-rhamnosidase inhibitors: Synthesis and biological evaluation of l-DMDP cyclic isothioureas.
AID210962	Concentration that causes 50% inhibition of mammalian trehalase was determined in porcine kidney	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID40274	Concentration that causes 50% inhibition of mammalian lysosomal beta-galactosidase was determined in rat liver; NI is less than 50 % inhibition at 1000 uM	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID105269	Concentration giving 50% inhibition of HIV-1 induced cytopathogenicity in MOLT-4 cells	1995	Journal of medicinal chemistry, Jun-23, Volume: 38, Issue:13	N-alkylated nitrogen-in-the-ring sugars: conformational basis of inhibition of glycosidases and HIV-1 replication.
AID324677	Inhibition of yeast alpha-glucosidase	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Effect of five-membered sugar mimics on mammalian glycogen-degrading enzymes and various glucosidases.
AID37277	Concentration that causes 50% inhibition of mammalian alpha-glucosidase (isomaltase) was determined in rat intestine	1994	Journal of medicinal chemistry, Oct-28, Volume: 37, Issue:22	Nitrogen-in-the-ring pyranoses and furanoses: structural basis of inhibition of mammalian glycosidases.
AID324679	Inhibition of rat isomaltase	2008	Bioorganic & medicinal chemistry, Mar-15, Volume: 16, Issue:6	Effect of five-membered sugar mimics on mammalian glycogen-degrading enzymes and various glucosidases.
AID33276	Concentration that causes 50% inhibition of mammalian alpha-mannosidase (golgi I) was determined in rat liver NI is less than 50 % inhibition at 1000 uM	1994	Journal 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]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	6 (17.65)	18.7374
1990's	10 (29.41)	18.2507
2000's	13 (38.24)	29.6817
2010's	5 (14.71)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	1 (2.63%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	37 (97.37%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
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.	1.99	1	monochlorobenzenes; 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
sorbitol D-glucitol : The D-enantiomer of glucitol (also known as D-sorbitol).	2.03	1	glucitol	cathartic; Escherichia coli metabolite; food humectant; human metabolite; laxative; metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite; sweetening agent
galactose galactopyranose : The pyranose form of galactose.	2.39	2	D-galactose; galactopyranose	Escherichia coli metabolite; mouse metabolite
lactose Lactose: A disaccharide of GLUCOSE and GALACTOSE in human and cow milk. It is used in pharmacy for tablets, in medicine as a nutrient, and in industry.. lactose : A glycosylglucose disaccharide, found most notably in milk, that consists of D-galactose and D-glucose fragments bonded through a beta-1->4 glycosidic linkage. The glucose fragment can be in either the alpha- or beta-pyranose form, whereas the galactose fragment can only have the beta-pyranose form.. beta-lactose : The beta-anomer of lactose.	2.02	1	lactose
mannitol [no description available]	5.7	26	mannitol	allergen; antiglaucoma drug; compatible osmolytes; Escherichia coli metabolite; food anticaking agent; food bulking agent; food humectant; food stabiliser; food thickening agent; hapten; metabolite; osmotic diuretic; sweetening agent
pyrroles 1H-pyrrole : A tautomer of pyrrole that has the double bonds at positions 2 and 4.. pyrrole : A five-membered monocyclic heteroarene comprising one NH and four CH units which forms the parent compound of the pyrrole group of compounds. Its five-membered ring structure has three tautomers. A 'closed class'.. azole : Any monocyclic heteroarene consisting of a five-membered ring containing nitrogen. Azoles can also contain one or more other non-carbon atoms, such as nitrogen, sulfur or oxygen.	2.01	1	pyrrole; secondary amine
3,4-epoxy-1-butene 3,4-epoxy-1-butene: RN given refers to monomer	2.03	1
mannose mannopyranose : The pyranose form of mannose.	1.96	1	D-aldohexose; D-mannose; mannopyranose	metabolite
palladium Palladium: A chemical element having an atomic weight of 106.4, atomic number of 46, and the symbol Pd. It is a white, ductile metal resembling platinum, and following it in abundance and importance of applications. It is used in dentistry in the form of gold, silver, and copper alloys.. palladium : Chemical element (nickel group element atom) with atomic number 46.	2.03	1	metal allergen; nickel group element atom; platinum group metal atom
fluorine Fluorine: A nonmetallic, diatomic gas that is a trace element and member of the halogen family. It is used in dentistry as fluoride (FLUORIDES) to prevent dental caries.	2.05	1	diatomic fluorine; gas molecular entity	NMR chemical shift reference compound
clodronic acid Clodronic Acid: A diphosphonate which affects calcium metabolism. It inhibits bone resorption and soft tissue calcification.. clodronic acid : An organochlorine compound that is methylene chloride in which both hydrogens are replaced by phosphonic acid groups. It inhibits bone resorption and soft tissue calcification, and is used (often as the disodium salt tetrahydrate) as an adjunct in the treatment of severe hypercalcaemia associated with malignancy, and in the management of osteolytic lesions and bone pain associated with skeletal metastases.	1.97	1	1,1-bis(phosphonic acid); one-carbon compound; organochlorine compound	antineoplastic agent; bone density conservation agent
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.	9.96	12	2-(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.	1.98	1	piperidines; tertiary amino compound	anti-HIV agent; EC 2.4.1.80 (ceramide glucosyltransferase) inhibitor
swainsonine Swainsonine: An indolizidine alkaloid from the plant Swainsona canescens that is a potent alpha-mannosidase inhibitor. Swainsonine also exhibits antimetastatic, antiproliferative, and immunomodulatory activity.. swainsonine : An indolizidine alkaloid isolated from the plant Swainsona canescens with three hydroxy substituents at positions 1, 2 and 8.	2.66	3	indolizidine alkaloid	antineoplastic agent; EC 3.2.1.114 (mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase) inhibitor; immunological adjuvant; plant metabolite
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).	2.89	4	indolizidine alkaloid	anti-HIV-1 agent; anti-inflammatory agent; EC 3.2.1.* (glycosidase) inhibitor; metabolite
chlorosulfonyl isocyanate chlorosulfonyl isocyanate: structure in first source	2.03	1
1-deoxymannojirimycin [no description available]	1.98	1
fagomine fagomine: structure in first source	2.39	2	piperidines
mor-14 N-methyldeoxynojirimycin: glucosidase inhibitor	1.98	1	hydroxypiperidine; piperidine alkaloid; tertiary amino compound	anti-HIV agent; cardioprotective agent; EC 3.2.1.20 (alpha-glucosidase) inhibitor; plant metabolite
cyanates Cyanates: Organic salts of cyanic acid containing the -OCN radical.. cyanates : Salts and esters of cyanic acid, HOC#N; compounds carrying the cyanate functional group -O-C#N.. isocyanates : Organonitrogen compounds that are derivatives of isocyanic acid; compounds containing the isocyanate functional group -N=C=O (as opposed to the cyanate group, -O-C#N).	2.03	1
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	2.04	1
homonojirimycin homonojirimycin: inhibits alpha-glucosidase; RN given for (2R-(2alpha,3alpha,4beta,5alpha,6beta))-isomer; structure in first source	2.74	3
gulonolactone gulonolactone: RN given refers to cpd without isomeric designation	2.02	1	gamma-lactone
migalastat migalastat: a potent inhibitor of glycolipid biosynthesis	2.05	1	piperidines
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.	2.66	3	D-glucosamine	Escherichia coli metabolite; geroprotector; mouse metabolite
miglitol [no description available]	2.01	1	piperidines
2,5-dideoxy-2,5-imino-d-glucitol 2,5-dideoxy-2,5-imino-D-glucitol: structure in first source	2.44	2
1,4-dideoxy-1,4-iminoarabinitol, (2r-(2alpha,3beta,4beta))-isomer [no description available]	2.43	2	pyrrolidines
1,4-dideoxy-1,4-imino-d-arabinitol [no description available]	2.91	4
D-fructopyranose [no description available]	2.03	1	cyclic hemiketal; D-fructose; fructopyranose	sweetening agent
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.	2.08	1	harmala alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; metabolite
harman harman: a beta-carboline; RN given refers to parent cpd; structure. harman : An indole alkaloid fundamental parent with a structure of 9H-beta-carboline carrying a methyl substituent at C-1. It has been isolated from the bark of Sickingia rubra, Symplocus racemosa, Passiflora incarnata, Peganum harmala, Banisteriopsis caapi and Tribulus terrestris, as well as from tobacco smoke. It is a specific, reversible inhibitor of monoamine oxidase A.	2.08	1	harmala alkaloid; indole alkaloid fundamental parent; indole alkaloid	anti-HIV agent; EC 1.4.3.4 (monoamine oxidase) inhibitor; plant metabolite
geldanamycin [no description available]	2.02	1
salacinol salacinol: a sulfated thiosugar from Salacia reticulata (CELASTRACEAE); structure in first source	2.04	1
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).	2.39	2	amino 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
piperidines Piperidines: A family of hexahydropyridines.	1.99	1
neosalacinol [no description available]	2.04	1
warfarin Warfarin: An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide.. warfarin : A racemate comprising equal amounts of (R)- and (S)-warfarin. Extensively used as both an anticoagulant drug and as a pesticide against rats and mice.. 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one : A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.	2	1	benzenes; hydroxycoumarin; methyl ketone

Condition	Relationship Strength	Studies
Alloxan Diabetes [description not available]	1.99	1
Cell Transformation, Viral An inheritable change in cells manifested by changes in cell division and growth and alterations in cell surface properties. It is induced by infection with a transforming virus.	2.37	2
HIV Human immunodeficiency virus. A non-taxonomic and historical term referring to any of two species, specifically HIV-1 and/or HIV-2. Prior to 1986, this was called human T-lymphotropic virus type III/lymphadenopathy-associated virus (HTLV-III/LAV). From 1986-1990, it was an official species called HIV. Since 1991, HIV was no longer considered an official species name; the two species were designated HIV-1 and HIV-2.	3.29	2
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	1.98	1
Acute Disease Disease having a short and relatively severe course.	1.98	1
Invasiveness, Neoplasm [description not available]	1.97	1
Ganglioside Storage Diseases [description not available]	1.96	1
Cat Diseases Diseases of the domestic cat (Felis catus or F. domesticus). This term does not include diseases of the so-called big cats such as CHEETAHS; LIONS; tigers, cougars, panthers, leopards, and other Felidae for which the heading CARNIVORA is used.	1.96	1
Gangliosidoses A group of autosomal recessive lysosomal storage disorders marked by the accumulation of GANGLIOSIDES. They are caused by impaired enzymes or defective cofactors required for normal ganglioside degradation in the LYSOSOMES. Gangliosidoses are classified by the specific ganglioside accumulated in the defective degradation pathway.	1.96	1

2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine

Description

Cross-References

Synonyms (31)

Drug Classes (1)

Protein Targets (9)

Inhibition Measurements

Biological Processes (19)

Molecular Functions (18)

Ceullar Components (18)

Bioassays (73)

Research

Studies (34)

Market Indicators

Research Demand Index: 10.84

Study Types

2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine

Description

Cross-References

Synonyms (31)

Drug Classes (1)

Protein Targets (9)

Inhibition Measurements

Biological Processes (19)

Molecular Functions (18)

Ceullar Components (18)

Bioassays (73)

Research

Studies (34)

Market Indicators

Research Demand Index: 10.84

Study Types

Related Drugs (38)

Related Conditions (9)