Compounds > deoxyfuconojirimycin
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deoxyfuconojirimycin

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

Description

Deoxyfuconojirimycin is a potent inhibitor of α-glucosidase, an enzyme that plays a critical role in carbohydrate metabolism. It has been studied for its potential therapeutic applications in treating type 2 diabetes and other metabolic disorders. The synthesis of deoxyfuconojirimycin involves a multi-step process, often utilizing chemical reactions and enzymatic transformations. Its effects on the body are mainly attributed to its ability to inhibit α-glucosidase, which leads to a slower breakdown of carbohydrates and a decrease in blood sugar levels. Studies on deoxyfuconojirimycin are motivated by its promising antidiabetic properties, as well as its potential applications in other areas such as drug delivery and anti-viral therapy. '

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

deoxyfuconojirimycin : A hydroxypiperidine in which the three hydroxy substituents are located at positions 3, 4 and 5 together with an additional methyl substituent at position 2. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID122618
CHEMBL ID314772
CHEBI ID132866
SCHEMBL ID4378188
MeSH IDM0173332

Synonyms (21)

Synonym
CHEMBL314772 ,
1,5-dideoxy-1,5-imino-l-fucitol
99212-30-3
(2s,3r,4s,5r)-2-methylpiperidine-3,4,5-triol
deoxyfuconojirimycin
3,4,5-piperidinetriol, 2-methyl-, (2s,3r,4s,5r)-
l-fuco-deoxynojirimycin
1,5-dideoxy-1,5-iminofucitol
CHEBI:132866
1,2,6-trideoxy-2,6-imino-d-galactitol
bdbm50065258
fucosidase inhibitor, 3
(2s,3r,4s,5r)-2-methyl-piperidine-3,4,5-triol
AKOS006283710
deoxyfuco-nojirimycin
d-galactitol, 1,2,6-trideoxy-2,6-imino-
deoxyfuconojirimycin hcl
SCHEMBL4378188
1-deoxyfuconojirimycin
DTXSID60912837
Q27459214
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
fungal metaboliteAny eukaryotic metabolite produced during a metabolic reaction in fungi, the kingdom that includes microorganisms such as the yeasts and moulds.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (2)

ClassDescription
hydroxypiperidine
triolA chemical compound containing three hydroxy groups.
[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 (3)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Tissue alpha-L-fucosidaseHomo sapiens (human)IC50 (µMol)0.23000.14000.23500.4100AID1819246; AID36819; AID779302
Tissue alpha-L-fucosidaseHomo sapiens (human)Ki0.04500.01001.59674.7000AID263091; AID36836
Tissue alpha-L-fucosidaseRattus norvegicus (Norway rat)IC50 (µMol)0.34000.34000.34000.3400AID779303
Tissue alpha-L-fucosidaseBos taurus (cattle)IC50 (µMol)0.05750.00500.05750.1100AID261196; AID779304
Tissue alpha-L-fucosidaseBos taurus (cattle)Ki0.00260.00171.17694.7000AID238243; AID261196; AID453109
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (4)

Processvia Protein(s)Taxonomy
fucose metabolic processTissue alpha-L-fucosidaseHomo sapiens (human)
glycosaminoglycan catabolic processTissue alpha-L-fucosidaseHomo sapiens (human)
glycoside catabolic processTissue alpha-L-fucosidaseHomo sapiens (human)
glycolipid catabolic processTissue alpha-L-fucosidaseHomo sapiens (human)
glycolipid catabolic processTissue alpha-L-fucosidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (2)

Processvia Protein(s)Taxonomy
alpha-L-fucosidase activityTissue alpha-L-fucosidaseHomo sapiens (human)
protein bindingTissue alpha-L-fucosidaseHomo sapiens (human)
alpha-L-fucosidase activityTissue alpha-L-fucosidaseBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (7)

Processvia Protein(s)Taxonomy
extracellular regionTissue alpha-L-fucosidaseHomo sapiens (human)
cytoplasmTissue alpha-L-fucosidaseHomo sapiens (human)
azurophil granule lumenTissue alpha-L-fucosidaseHomo sapiens (human)
lysosomal lumenTissue alpha-L-fucosidaseHomo sapiens (human)
intracellular membrane-bounded organelleTissue alpha-L-fucosidaseHomo sapiens (human)
extracellular exosomeTissue alpha-L-fucosidaseHomo sapiens (human)
lysosomeTissue alpha-L-fucosidaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (22)

Assay IDTitleYearJournalArticle
AID261196Inhibition of bovine alpha-L-fucosidase2006Bioorganic & medicinal chemistry letters, Mar-01, Volume: 16, Issue:5
Asymmetric synthesis of the L-fuco-nojirimycin, a nanomolar alpha-L-fucosidase inhibitor.
AID779309Inhibition of snail beta-mannosidase assessed as inhibition of p-nitrophenol release at 1000 uM by spectrophotometry2013Bioorganic & medicinal chemistry, Nov-01, Volume: 21, Issue:21
Synthesis and biological evaluation of N-(2-fluorophenyl)-2β-deoxyfuconojirimycin acetamide as a potent inhibitor for α-l-fucosidases.
AID263091Inhibition of human liver alpha-L-fucosidase2006Bioorganic & medicinal chemistry letters, Apr-15, Volume: 16, Issue:8
Fluorescent glycosidase inhibiting 1,5-dideoxy-1,5-iminoalditols.
AID40152Inhibitory activity against Beta-galactosidase in bovine liver was determined;NI means no inhibition2002Bioorganic & medicinal chemistry letters, Oct-21, Volume: 12, Issue:20
Convenient synthesis and evaluation of enzyme inhibitory activity of several N-alkyl-, N-phenylalkyl, and cyclic isourea derivatives of 5a-carba-alpha-DL-fucopyranosylamine.
AID453112Inhibition of Penicillium decumbens Alpha-L-rhamnosidase by para-nitrophenolate release assay2009Bioorganic & medicinal chemistry, Dec-01, Volume: 17, Issue:23
The spirocyclopropyl moiety as a methyl surrogate in the structure of l-fucosidase and l-rhamnosidase inhibitors.
AID779310Inhibition of jack beans alpha-mannosidase assessed as inhibition of p-nitrophenol release at 1000 uM by spectrophotometry2013Bioorganic & medicinal chemistry, Nov-01, Volume: 21, Issue:21
Synthesis and biological evaluation of N-(2-fluorophenyl)-2β-deoxyfuconojirimycin acetamide as a potent inhibitor for α-l-fucosidases.
AID36827Binding affinity against alpha-L-fucosidase in bovine kidney was determined2002Bioorganic & medicinal chemistry letters, Oct-21, Volume: 12, Issue:20
Convenient synthesis and evaluation of enzyme inhibitory activity of several N-alkyl-, N-phenylalkyl, and cyclic isourea derivatives of 5a-carba-alpha-DL-fucopyranosylamine.
AID36819Inhibition of bovine kidney alpha-L-fucosidase2002Bioorganic & medicinal chemistry letters, Oct-21, Volume: 12, Issue:20
Convenient synthesis and evaluation of enzyme inhibitory activity of several N-alkyl-, N-phenylalkyl, and cyclic isourea derivatives of 5a-carba-alpha-DL-fucopyranosylamine.
AID779299Inhibition of coffee beans alpha-galactosidase assessed as inhibition of p-nitrophenol release at 1000 uM by spectrophotometry2013Bioorganic & medicinal chemistry, Nov-01, Volume: 21, Issue:21
Synthesis and biological evaluation of N-(2-fluorophenyl)-2β-deoxyfuconojirimycin acetamide as a potent inhibitor for α-l-fucosidases.
AID36836Inhibitory activity measured against alpha-L-fucosidase of bovine epididymis by colorimetric assay using the D-glucose oxidase-peroxidase method1998Journal of medicinal chemistry, Jul-02, Volume: 41, Issue:14
Homonojirimycin isomers and N-alkylated homonojirimycins: structural and conformational basis of inhibition of glycosidases.
AID779301Inhibition of rat intestinal maltase using maltose as substrate assessed as inhibition of D-glucose production at 1000 uM after 10 mins by spectrophotometry2013Bioorganic & medicinal chemistry, Nov-01, Volume: 21, Issue:21
Synthesis and biological evaluation of N-(2-fluorophenyl)-2β-deoxyfuconojirimycin acetamide as a potent inhibitor for α-l-fucosidases.
AID453109Inhibition of bovine kidney alpha-L-fucosidase by para-nitrophenolate release assay2009Bioorganic & medicinal chemistry, Dec-01, Volume: 17, Issue:23
The spirocyclopropyl moiety as a methyl surrogate in the structure of l-fucosidase and l-rhamnosidase inhibitors.
AID779304Inhibition of bovine kidney alpha-L-fucosidase assessed as inhibition of release of p-nitrophenol by spectrophotometry2013Bioorganic & medicinal chemistry, Nov-01, Volume: 21, Issue:21
Synthesis and biological evaluation of N-(2-fluorophenyl)-2β-deoxyfuconojirimycin acetamide as a potent inhibitor for α-l-fucosidases.
AID779297Inhibition of bovine liver beta-galactosidase assessed as inhibition of p-nitrophenol release at 1000 uM by spectrophotometry2013Bioorganic & medicinal chemistry, Nov-01, Volume: 21, Issue:21
Synthesis and biological evaluation of N-(2-fluorophenyl)-2β-deoxyfuconojirimycin acetamide as a potent inhibitor for α-l-fucosidases.
AID218950Inhibitory activity against alpha-L-fucosidase in bovine epididymis; Competitive Inhibition type1998Bioorganic & medicinal chemistry letters, Nov-17, Volume: 8, Issue:22
Thio-sugars. IV: Design and synthesis of S-linked fucoside analogs as a new class of alpha-L-fucosidase inhibitors.
AID779303Inhibition of rat epididymis alpha-L-fucosidase assessed as inhibition of release of p-nitrophenol by spectrophotometry2013Bioorganic & medicinal chemistry, Nov-01, Volume: 21, Issue:21
Synthesis and biological evaluation of N-(2-fluorophenyl)-2β-deoxyfuconojirimycin acetamide as a potent inhibitor for α-l-fucosidases.
AID779308Inhibition of Escherichia coli beta-glucuronidase assessed as inhibition of p-nitrophenol release at 1000 uM by spectrophotometry2013Bioorganic & medicinal chemistry, Nov-01, Volume: 21, Issue:21
Synthesis and biological evaluation of N-(2-fluorophenyl)-2β-deoxyfuconojirimycin acetamide as a potent inhibitor for α-l-fucosidases.
AID238243Ki value against bovine alpha-L-fucosidase2005Journal of medicinal chemistry, Mar-24, Volume: 48, Issue:6
Biological properties of D- and L-1-deoxyazasugars.
AID779302Inhibition of human lysosome alpha-L-fucosidase using 4-methylumbelliferyl-alpha-L-fucopyranoside by spectrophotometry2013Bioorganic & medicinal chemistry, Nov-01, Volume: 21, Issue:21
Synthesis and biological evaluation of N-(2-fluorophenyl)-2β-deoxyfuconojirimycin acetamide as a potent inhibitor for α-l-fucosidases.
AID1819246Inhibition of placental alpha-L-fucosidase (unknown origin)2022Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3
5-
AID779300Inhibition of bovine liver beta-glucosidase assessed as inhibition of p-nitrophenol release at 1000 uM by spectrophotometry2013Bioorganic & medicinal chemistry, Nov-01, Volume: 21, Issue:21
Synthesis and biological evaluation of N-(2-fluorophenyl)-2β-deoxyfuconojirimycin acetamide as a potent inhibitor for α-l-fucosidases.
AID1799637Enzyme Assay from Article 10.1002/cbic.201000339: \\Structural and thermodynamic analyses of u00CEu00B1-L-fucosidase inhibitors.\\2010Chembiochem : a European journal of chemical biology, Sep-24, Volume: 11, Issue:14
Structural and thermodynamic analyses of α-L-fucosidase inhibitors.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (20)

TimeframeStudies, This Drug (%)All Drugs %
pre-19900 (0.00)18.7374
1990's5 (25.00)18.2507
2000's8 (40.00)29.6817
2010's6 (30.00)24.3611
2020's1 (5.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 11.55

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

MetricThis Compound (vs All)
Research Demand Index11.55 (24.57)
Research Supply Index3.04 (2.92)
Research Growth Index4.59 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (11.55)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews1 (5.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other19 (95.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
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.		2.9440fucopyranose;
L-fucose		Escherichia coli metabolite;
mouse metabolite
deuterium oxide
Deuterium Oxide: The isotopic compound of hydrogen of mass 2 (deuterium) with oxygen. (From Grant & Hackh's Chemical Dictionary, 5th ed) It is used to study mechanisms and rates of chemical or nuclear reactions, as well as biological processes.		1.9910deuterated compound;
water		NMR solvent
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.		5.151402-(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
alkenes
[no description available]		2.0710
miglustat
miglustat: a glucosylceramide synthase inhibitor. miglustat : A hydroxypiperidine that is deoxynojirimycin in which the amino hydrogen is replaced by a butyl group.		2.4110piperidines;
tertiary amino compound		anti-HIV agent;
EC 2.4.1.80 (ceramide glucosyltransferase) inhibitor
1-deoxymannojirimycin
[no description available]		2.7130
mor-14
N-methyldeoxynojirimycin: glucosidase inhibitor		2.4110hydroxypiperidine;
piperidine alkaloid;
tertiary amino compound		anti-HIV agent;
cardioprotective agent;
EC 3.2.1.20 (alpha-glucosidase) inhibitor;
plant metabolite
2-acetamido-1,5-imino-1,2,5-trideoxy-d-glucitol
2-acetamido-1,5-imino-1,2,5-trideoxy-D-glucitol: structure given in first source		2.0310
benzyne
benzyne: structure in first source. benzyne : 1,2-didehydrobenzene and its derivatives formed by substitution.		2.0710aryne;
benzyne
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		2.4110
homonojirimycin
homonojirimycin: inhibits alpha-glucosidase; RN given for (2R-(2alpha,3alpha,4beta,5alpha,6beta))-isomer; structure in first source		1.9910
migalastat
migalastat: a potent inhibitor of glycolipid biosynthesis		2.4320piperidines
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.		3.4820D-glucosamineEscherichia coli metabolite;
geroprotector;
mouse metabolite
n-acetyllactosamine
N-acetyllactosamine: RN given refers to D-isomer. N-acetyllactosamine : A beta-D-galactopyranosyl-(1->4)-N-acetyl-D-glucosamine having beta-configuration at the reducing end anomeric centre.		1.9910beta-D-Galp-(1->4)-D-GlcpNAc
isofagomine
[no description available]		2.0310piperidines
1,4-dideoxy-1,4-imino-d-arabinitol
[no description available]		2.4110
melphalan
Melphalan: An alkylating nitrogen mustard that is used as an antineoplastic in the form of the levo isomer - MELPHALAN, the racemic mixture - MERPHALAN, and the dextro isomer - MEDPHALAN; toxic to bone marrow, but little vesicant action; potential carcinogen.. melphalan : A phenylalanine derivative comprising L-phenylalanine having [bis(2-chloroethyl)amino group at the 4-position on the phenyl ring.		2.2110L-phenylalanine derivative;
nitrogen mustard;
non-proteinogenic L-alpha-amino acid;
organochlorine compound		alkylating agent;
antineoplastic agent;
carcinogenic agent;
drug allergen;
immunosuppressive agent
l-altro-1-deoxynojirimycin
L-altro-1-deoxynojirimycin: structure in first source		2.0210
lewis x antigen
Lewis X Antigen: A trisaccharide antigen expressed on glycolipids and many cell-surface glycoproteins. In the blood the antigen is found on the surface of NEUTROPHILS; EOSINOPHILS; and MONOCYTES. In addition, Lewis X antigen is a stage-specific embryonic antigen.		2.4120
guanosine diphosphate
Guanosine Diphosphate: A guanine nucleotide containing two phosphate groups esterified to the sugar moiety.		1.9910guanosine 5'-phosphate;
purine ribonucleoside 5'-diphosphate		Escherichia coli metabolite;
mouse metabolite;
uncoupling protein inhibitor
cytarabine
Guanosine Diphosphate Fucose: A nucleoside diphosphate sugar formed from GDPmannose, which provides fucose for lipopolysaccharides of bacterial cell walls, and for blood group substances and other glycoproteins.		1.9910GDP-fucose
ConditionIndicatedRelationship StrengthStudiesTrials
Acid Alpha-Glucosidase Deficiency
[description not available]		02.4110
Glycogen Storage Disease Type II
An autosomal recessively inherited glycogen storage disease caused by GLUCAN 1,4-ALPHA-GLUCOSIDASE deficiency. Large amounts of GLYCOGEN accumulate in the LYSOSOMES of skeletal muscle (MUSCLE, SKELETAL); HEART; LIVER; SPINAL CORD; and BRAIN. Three forms have been described: infantile, childhood, and adult. The infantile form is fatal in infancy and presents with hypotonia and a hypertrophic cardiomyopathy (CARDIOMYOPATHY, HYPERTROPHIC). The childhood form usually presents in the second year of life with proximal weakness and respiratory symptoms. The adult form consists of a slowly progressive proximal myopathy. (From Muscle Nerve 1995;3:S61-9; Menkes, Textbook of Child Neurology, 5th ed, pp73-4)		02.4110
Reproductive Sterility
[description not available]		02.0810
Infertility
A reduced or absent capacity to reproduce.		02.0810
Disease Exacerbation
[description not available]		02.0410
Breast Cancer
[description not available]		02.0410
Invasiveness, Neoplasm
[description not available]		02.0410
Breast Neoplasms
Tumors or cancer of the human BREAST.		02.0410