1,4-dideoxy-1,4-iminoarabinitol profile

1,4-dideoxy-1,4-iminoarabinitol, also known as **DNJ** (deoxynojirimycin), is a naturally occurring iminosugar with significant interest in research. Here's why:

**What it is:**

* **Structure:** DNJ is a sugar analog that resembles glucose but with a nitrogen atom replacing the oxygen atom in the ring structure.
* **Natural occurrence:** Found in plants like mulberry and various legumes.
* **Biological activity:** It's a potent inhibitor of α-glucosidase enzymes.

**Why it's important for research:**

**1. Therapeutic Potential:**

* **Type 2 Diabetes:** DNJ inhibits α-glucosidase enzymes, which are responsible for breaking down carbohydrates in the intestines. By delaying carbohydrate absorption, DNJ can help regulate blood glucose levels, making it a potential therapeutic agent for type 2 diabetes.
* **Other diseases:** DNJ has shown potential in treating other diseases like obesity, cancer, and viral infections. It's been explored for its anti-inflammatory and neuroprotective properties.

**2. Drug Development:**

* **Drug lead:** DNJ serves as a lead compound for developing novel α-glucosidase inhibitors with improved pharmacokinetic profiles and therapeutic effects.
* **Targeted delivery:** Research focuses on developing DNJ analogs with enhanced specificity for specific tissues or organs to improve efficacy and minimize side effects.

**3. Research Tool:**

* **Studying enzyme function:** DNJ acts as a valuable tool for investigating the role of α-glucosidases in various biological processes.
* **Understanding metabolism:** DNJ's interaction with carbohydrate metabolism provides insights into the regulation of glucose homeostasis and other metabolic pathways.

**Current Research:**

* **Clinical Trials:** Ongoing clinical trials are evaluating the safety and efficacy of DNJ and its derivatives as treatments for diabetes and other conditions.
* **Novel Analogs:** Researchers are actively designing and synthesizing new DNJ analogs with improved pharmacological properties.
* **Mechanistic Studies:** Investigations are underway to understand the precise mechanisms by which DNJ exerts its therapeutic effects.

**In summary:** 1,4-dideoxy-1,4-iminoarabinitol (DNJ) is a promising iminosugar with significant potential in therapeutic applications, drug development, and research. Its ability to inhibit α-glucosidases and its versatility as a research tool make it a valuable compound for exploring various aspects of human health and disease.

1,4-dideoxy-1,4-iminoarabinitol: RN given refers to (2S-(2alpha,3beta,4alpha))-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

ID Source	ID
PubMed CID	127716
CHEMBL ID	406973
SCHEMBL ID	754269
MeSH ID	M0162282

Synonym
3,4-pyrrolidinediol, 2-(hydroxymethyl)-, [2s-(2a,3b,4a)]-
1,4-dideoxy-1,4-imino-l-arabinitol
3,4-pyrrolidinediol, 2-(hydroxymethyl)-, (2s,3s,4s)-
(2s,3s,4s)-2-(hydroxymethyl)pyrrolidine-3,4-diol
100937-53-9
DB03411
CHEMBL406973 ,
EDG ,
bdbm50375511
l-arabinitol, 1,4-dideoxy-1,4-imino-
1,4-dideoxy-1,4-iminoarabinitol
1,4-dideoxy-1,4-iminoribitol
z330x18gmd ,
2-hydroxymethylpyrrolidine-3,4-diol
unii-z330x18gmd
1,4-ddir
SCHEMBL754269
Q27094339
C91319
DTXSID10905855
(2s,3s,4s)-3,4-dihydroxy-2-hydroxymethylpyrrolidine
GLXC-26785
gaa stabilizer 21
1,4-dideoxy-1,4-imino-l-arabinitol; (2s,3s,4s)-2-(hydroxymethyl)pyrrolidine-3,4-diol
PD007012

Excerpt	Reference	Relevance
"To further characterize the properties of 1,4-dideoxy-1,4-imino-d-arabinitol (DAB), a recently described novel and potent inhibitor of glycogen phosphorylase and potential anti-diabetic agent, we have determined its pharmacokinetic properties in rats, dogs and mice and compared these to its pharmacodynamic anti-hyperglycaemic efficacy."	( Pharmacokinetics and anti-hyperglycaemic efficacy of a novel inhibitor of glycogen phosphorylase, 1,4-dideoxy-1,4-imino-d- arabinitol, in glucagon-challenged rats and dogs and in diabetic ob/ob mice. Andersen, JV; Mackay, P; McCormack, JG; Ynddal, L, 2003)	0.32

Excerpt	Reference	Relevance
") administration; the oral bioavailability was 89%."	( Pharmacokinetics and anti-hyperglycaemic efficacy of a novel inhibitor of glycogen phosphorylase, 1,4-dideoxy-1,4-imino-d- arabinitol, in glucagon-challenged rats and dogs and in diabetic ob/ob mice. Andersen, JV; Mackay, P; McCormack, JG; Ynddal, L, 2003)	0.32

Excerpt	Relevance	Reference
" DAB was very rapidly cleared in mice; nevertheless, a dose-dependent reduction of blood glucose of up to 9 mmol/l was seen in diabetic ob/ob mice dosed subcutaneously, with statistically significant effects evident from 30 to 120 min."	( Pharmacokinetics and anti-hyperglycaemic efficacy of a novel inhibitor of glycogen phosphorylase, 1,4-dideoxy-1,4-imino-d- arabinitol, in glucagon-challenged rats and dogs and in diabetic ob/ob mice. Andersen, JV; Mackay, P; McCormack, JG; Ynddal, L, 2003)	0.32

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Trehalase	Sus scrofa (pig)	IC50 (µMol)	131.0000	2.5000	2.5000	2.5000	AID711095
Beta-galactosidase	Escherichia coli K-12	Ki	4.3000	4.3000	4.3000	4.3000	AID1322901
Sucrase-isomaltase, intestinal	Homo sapiens (human)	IC50 (µMol)	1.0000	0.0490	2.7294	7.8000	AID1819252
Sucrase-isomaltase, intestinal	Rattus norvegicus (Norway rat)	IC50 (µMol)	0.8286	0.0400	1.8483	10.0000	AID1879699; AID1879700; AID324678; AID324679; AID324680; AID711102; AID711103
Glycogen debranching enzyme	Homo sapiens (human)	IC50 (µMol)	200.0000	8.4000	9.5143	10.0000	AID324673
Lactase-phlorizin hydrolase	Rattus norvegicus (Norway rat)	IC50 (µMol)	415.0000	0.1200	2.9867	4.4000	AID711098
Alpha-galactosidase	Coffea arabica (coffee)	Ki	2.0000	0.0130	1.0065	2.0000	AID1322900
Lysosomal alpha-glucosidase	Rattus norvegicus (Norway rat)	IC50 (µMol)	0.9300	0.0800	2.5061	9.8500	AID1879698; AID711104
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Process	via Protein(s)	Taxonomy
lactose catabolic process	Beta-galactosidase	Escherichia coli K-12
carbohydrate metabolic process	Beta-galactosidase	Escherichia coli K-12
lactose catabolic process	Beta-galactosidase	Escherichia coli K-12
sucrose catabolic process	Sucrase-isomaltase, intestinal	Homo sapiens (human)
polysaccharide digestion	Sucrase-isomaltase, 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)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
magnesium ion binding	Beta-galactosidase	Escherichia coli K-12
beta-galactosidase activity	Beta-galactosidase	Escherichia coli K-12
hydrolase activity, acting on glycosyl bonds	Beta-galactosidase	Escherichia coli K-12
carbohydrate binding	Beta-galactosidase	Escherichia coli K-12
alkali metal ion binding	Beta-galactosidase	Escherichia coli K-12
identical protein binding	Beta-galactosidase	Escherichia coli K-12
metal ion binding	Beta-galactosidase	Escherichia coli K-12
oligo-1,6-glucosidase activity	Sucrase-isomaltase, intestinal	Homo sapiens (human)
sucrose alpha-glucosidase activity	Sucrase-isomaltase, intestinal	Homo sapiens (human)
protein binding	Sucrase-isomaltase, intestinal	Homo sapiens (human)
carbohydrate binding	Sucrase-isomaltase, intestinal	Homo sapiens (human)
alpha-1,4-glucosidase activity	Sucrase-isomaltase, 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)
[Information is prepared from geneontology information from the June-17-2024 release]

Process	via Protein(s)	Taxonomy
beta-galactosidase complex	Beta-galactosidase	Escherichia coli K-12
Golgi apparatus	Sucrase-isomaltase, intestinal	Homo sapiens (human)
plasma membrane	Sucrase-isomaltase, intestinal	Homo sapiens (human)
brush border	Sucrase-isomaltase, intestinal	Homo sapiens (human)
apical plasma membrane	Sucrase-isomaltase, intestinal	Homo sapiens (human)
extracellular exosome	Sucrase-isomaltase, 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)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (35)

Assay ID	Title	Year	Journal	Article
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.
AID711093	Inhibition of human beta-glucocerebrosidase at 1000 uM	2012	Journal of medicinal chemistry, Dec-13, Volume: 55, Issue:23	α-1-C-butyl-1,4-dideoxy-1,4-imino-l-arabinitol as a second-generation iminosugar-based oral α-glucosidase inhibitor for improving postprandial hyperglycemia.
AID711094	Inhibition of rat intestinal cellobiase using cellobiose as substrate at 1000 uM	2012	Journal of medicinal chemistry, Dec-13, Volume: 55, Issue:23	α-1-C-butyl-1,4-dideoxy-1,4-imino-l-arabinitol as a second-generation iminosugar-based oral α-glucosidase inhibitor for improving postprandial hyperglycemia.
AID711096	Inhibition of rat intestinal trehalase	2012	Journal of medicinal chemistry, Dec-13, Volume: 55, Issue:23	α-1-C-butyl-1,4-dideoxy-1,4-imino-l-arabinitol as a second-generation iminosugar-based oral α-glucosidase inhibitor for improving postprandial hyperglycemia.
AID324681	Inhibition of human lysosomal 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.
AID1322877	Inhibition of Penicillium decumbens naringinase at 2 mM after 10 to 30 mins by spectrophotometric method	2016	European journal of medicinal chemistry, Oct-04, Volume: 121	Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp(2)-iminosugar conjugates against glycosidases: A structure-activity relationship study in Gaucher fibroblasts.
AID1879700	Inhibition of rat intestinal sucrase assessed as release of p-nitrophenol using p-nitrophenyl glycoside as substrate by spectrometric assay	2022	European journal of medicinal chemistry, Apr-05, Volume: 233	Design, synthesis and glycosidase inhibition of C-4 branched LAB and DAB derivatives.
AID1322900	Inhibition of green coffee bean alpha-galactosidase using o-nitrophenyl alpha-D-galactopyranoside after 10 to 30 mins by spectrophotometric method	2016	European journal of medicinal chemistry, Oct-04, Volume: 121	Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp(2)-iminosugar conjugates against glycosidases: A structure-activity relationship study in Gaucher fibroblasts.
AID711095	Inhibition of porcine kidney trehalase	2012	Journal of medicinal chemistry, Dec-13, Volume: 55, Issue:23	α-1-C-butyl-1,4-dideoxy-1,4-imino-l-arabinitol as a second-generation iminosugar-based oral α-glucosidase inhibitor for improving postprandial hyperglycemia.
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.
AID710955	Inhibition of bovine liver beta-galactosidase at 1000 uM	2012	Journal of medicinal chemistry, Dec-13, Volume: 55, Issue:23	α-1-C-butyl-1,4-dideoxy-1,4-imino-l-arabinitol as a second-generation iminosugar-based oral α-glucosidase inhibitor for improving postprandial hyperglycemia.
AID1879699	Inhibition of rat intestinal isomaltase assessed as release of p-nitrophenol using p-nitrophenyl glycoside as substrate by spectrometric assay	2022	European journal of medicinal chemistry, Apr-05, Volume: 233	Design, synthesis and glycosidase inhibition of C-4 branched LAB and DAB derivatives.
AID1322871	Competitive inhibition of almond beta-glucosidase using beta-D-glycopyranoside as substrate after 10 to 30 mins by Lineweaver-Burk plot analysis	2016	European journal of medicinal chemistry, Oct-04, Volume: 121	Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp(2)-iminosugar conjugates against glycosidases: A structure-activity relationship study in Gaucher fibroblasts.
AID1322868	Competitive inhibition of baker's yeast isomaltase after 10 to 30 mins by Lineweaver-Burk plot analysis	2016	European journal of medicinal chemistry, Oct-04, Volume: 121	Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp(2)-iminosugar conjugates against glycosidases: A structure-activity relationship study in Gaucher fibroblasts.
AID1322901	Inhibition of Escherichia coli beta-galactosidase using o-nitrophenyl beta-D-galactopyranoside after 10 to 30 mins by spectrophotometric method	2016	European journal of medicinal chemistry, Oct-04, Volume: 121	Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp(2)-iminosugar conjugates against glycosidases: A structure-activity relationship study in Gaucher fibroblasts.
AID1322869	Competitive inhibition of Aspergillus niger amyloglucosidase after 10 to 30 mins by Lineweaver-Burk plot analysis	2016	European journal of medicinal chemistry, Oct-04, Volume: 121	Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp(2)-iminosugar conjugates against glycosidases: A structure-activity relationship study in Gaucher fibroblasts.
AID1322867	Competitive inhibition of baker's yeast alpha-glucosidase using alpha-D-glycopyranoside as substrate after 10 to 30 mins by Lineweaver-Burk plot analysis	2016	European journal of medicinal chemistry, Oct-04, Volume: 121	Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp(2)-iminosugar conjugates against glycosidases: A structure-activity relationship study in Gaucher fibroblasts.
AID711102	Inhibition of rat intestinal sucrase using sucrose as substrate	2012	Journal of medicinal chemistry, Dec-13, Volume: 55, Issue:23	α-1-C-butyl-1,4-dideoxy-1,4-imino-l-arabinitol as a second-generation iminosugar-based oral α-glucosidase inhibitor for improving postprandial hyperglycemia.
AID711098	Inhibition of rat intestinal lactase using lactose as substrate	2012	Journal of medicinal chemistry, Dec-13, Volume: 55, Issue:23	α-1-C-butyl-1,4-dideoxy-1,4-imino-l-arabinitol as a second-generation iminosugar-based oral α-glucosidase inhibitor for improving postprandial hyperglycemia.
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.
AID1322880	Inhibition of jack bean alpha-mannosidase at 2 mM after 10 to 30 mins by spectrophotometric method	2016	European journal of medicinal chemistry, Oct-04, Volume: 121	Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp(2)-iminosugar conjugates against glycosidases: A structure-activity relationship study in Gaucher fibroblasts.
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.
AID1819252	Inhibition of Sucrase (unknown origin)	2022	Journal of medicinal chemistry, 02-10, Volume: 65, Issue:3	5-
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.
AID1322881	Inhibition of Helix pomatia beta-mannosidase at 2 mM after 10 to 30 mins by spectrophotometric method	2016	European journal of medicinal chemistry, Oct-04, Volume: 121	Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp(2)-iminosugar conjugates against glycosidases: A structure-activity relationship study in Gaucher fibroblasts.
AID1879698	Inhibition of rat intestinal maltase assessed as release of D-glucose using maltose as substrate by colorimetric analysis	2022	European journal of medicinal chemistry, Apr-05, Volume: 233	Design, synthesis and glycosidase inhibition of C-4 branched LAB and DAB derivatives.
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.
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.
AID711092	Inhibition of bovine liver beta-glucosidase at 1000 uM	2012	Journal of medicinal chemistry, Dec-13, Volume: 55, Issue:23	α-1-C-butyl-1,4-dideoxy-1,4-imino-l-arabinitol as a second-generation iminosugar-based oral α-glucosidase inhibitor for improving postprandial hyperglycemia.
AID711104	Inhibition of rat intestinal maltase using moltose as substrate	2012	Journal of medicinal chemistry, Dec-13, Volume: 55, Issue:23	α-1-C-butyl-1,4-dideoxy-1,4-imino-l-arabinitol as a second-generation iminosugar-based oral α-glucosidase inhibitor for improving postprandial hyperglycemia.
AID1879701	Inhibition of human lysosomal alpha glucosidase assessed as release of p-nitrophenol using p-nitrophenyl glycoside as substrate by spectrometric assay	2022	European journal of medicinal chemistry, Apr-05, Volume: 233	Design, synthesis and glycosidase inhibition of C-4 branched LAB and DAB derivatives.
AID1322875	Inhibition of bovine liver cytosolic beta-glucosidase using beta-D-glycopyranoside as substrate at 2 mM after 10 to 30 mins by spectrophotometric method	2016	European journal of medicinal chemistry, Oct-04, Volume: 121	Inhibitor versus chaperone behaviour of d-fagomine, DAB and LAB sp(2)-iminosugar conjugates against glycosidases: A structure-activity relationship study in Gaucher fibroblasts.
AID1879710	Inhibition of bovine liver beta-glucosidase assessed as release of p-nitrophenol at 1000 uM using p-nitrophenyl glycoside as substrate by spectrometric assay relative to control	2022	European journal of medicinal chemistry, Apr-05, Volume: 233	Design, synthesis and glycosidase inhibition of C-4 branched LAB and DAB derivatives.
AID1879703	Inhibition of almond beta-glucosidase assessed as release of p-nitrophenol at 1000 uM using p-nitrophenyl glycoside as substrate by spectrometric assay relative to control	2022	European journal of medicinal chemistry, Apr-05, Volume: 233	Design, synthesis and glycosidase inhibition of C-4 branched LAB and DAB derivatives.
AID711103	Inhibition of rat intestinal isomaltase using isomaltase as substrate	2012	Journal of medicinal chemistry, Dec-13, Volume: 55, Issue:23	α-1-C-butyl-1,4-dideoxy-1,4-imino-l-arabinitol as a second-generation iminosugar-based oral α-glucosidase inhibitor for improving postprandial hyperglycemia.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (1.75)	18.7374
1990's	6 (10.53)	18.2507
2000's	24 (42.11)	29.6817
2010's	20 (35.09)	24.3611
2020's	6 (10.53)	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 (1.72%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	57 (98.28%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
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.	4.02	13	2-hydroxy monocarboxylic acid	algal metabolite; Daphnia magna metabolite
dihydroxyacetone phosphate Dihydroxyacetone Phosphate: An important intermediate in lipid biosynthesis and in glycolysis.. dihydroxyacetone phosphate : A member of the class of glycerone phosphates that consists of glycerone bearing a single phospho substituent.	2.1	1	glycerone phosphates; primary alpha-hydroxy ketone	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
ethanolamine [no description available]	2.1	1	ethanolamines; primary alcohol; primary amine	Escherichia coli metabolite; human metabolite; mouse metabolite
3-nitropropionic acid 3-nitropropionic acid: succinate dehydrogenase inactivator; biosynthesized by FABACEAE plants from ASPARAGINE. 3-nitropropanoic acid : A C-nitro compound that is propanoic acid in which one of the methyl hydrogens has been replaced by a nitro group.	2.31	1	C-nitro compound	antimycobacterial drug; EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor; mycotoxin; neurotoxin
caffeine [no description available]	2.42	2	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
hydroxyproline Hydroxyproline: A hydroxylated form of the imino acid proline. A deficiency in ASCORBIC ACID can result in impaired hydroxyproline formation.. hydroxyproline : A proline derivative that is proline substituted by at least one hydroxy group.	3.11	1	4-hydroxyproline; L-alpha-amino acid zwitterion	human metabolite; mouse metabolite; plant metabolite
alanine Alanine: A non-essential amino acid that occurs in high levels in its free state in plasma. It is produced from pyruvate by transamination. It is involved in sugar and acid metabolism, increases IMMUNITY, and provides energy for muscle tissue, BRAIN, and the CENTRAL NERVOUS SYSTEM.. alanine : An alpha-amino acid that consists of propionic acid bearing an amino substituent at position 2.	2.02	1	alanine zwitterion; alanine; L-alpha-amino acid; proteinogenic amino acid; pyruvate family amino acid	EC 4.3.1.15 (diaminopropionate ammonia-lyase) inhibitor; fundamental metabolite
aspartic acid Aspartic Acid: One of the non-essential amino acids commonly occurring in the L-form. It is found in animals and plants, especially in sugar cane and sugar beets. It may be a neurotransmitter.. aspartic acid : An alpha-amino acid that consists of succinic acid bearing a single alpha-amino substituent. L-aspartic acid : The L-enantiomer of aspartic acid.	2.44	2	aspartate family amino acid; aspartic acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; mouse metabolite; neurotransmitter
glutamine Glutamine: A non-essential amino acid present abundantly throughout the body and is involved in many metabolic processes. It is synthesized from GLUTAMIC ACID and AMMONIA. It is the principal carrier of NITROGEN in the body and is an important energy source for many cells.. L-glutamine : An optically active form of glutamine having L-configuration.. glutamine : An alpha-amino acid that consists of butyric acid bearing an amino substituent at position 2 and a carbamoyl substituent at position 4.	2.03	1	amino acid zwitterion; glutamine family amino acid; glutamine; L-alpha-amino acid; polar amino acid zwitterion; proteinogenic amino acid	EC 1.14.13.39 (nitric oxide synthase) inhibitor; Escherichia coli metabolite; human metabolite; metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
adenosine diphosphate Adenosine Diphosphate: Adenosine 5'-(trihydrogen diphosphate). An adenine nucleotide containing two phosphate groups esterified to the sugar moiety at the 5'-position.	2.03	1	adenosine 5'-phosphate; purine ribonucleoside 5'-diphosphate	fundamental metabolite; human metabolite
adenosine monophosphate Adenosine Monophosphate: Adenine nucleotide containing one phosphate group esterified to the sugar moiety in the 2'-, 3'-, or 5'-position.	2.03	1	adenosine 5'-phosphate; purine ribonucleoside 5'-monophosphate	adenosine A1 receptor agonist; cofactor; EC 3.1.3.1 (alkaline phosphatase) inhibitor; EC 3.1.3.11 (fructose-bisphosphatase) inhibitor; fundamental metabolite; micronutrient; nutraceutical
xylitol xylooligosaccharide: structure in first source. pentitol : An alditol obtained by reduction of any pentose.. xylooligosaccharide : An oligosaccharide comprised of xylose residues.	3.11	5
trehalose alpha,alpha-trehalose : A trehalose in which both glucose residues have alpha-configuration at the anomeric carbon.	2.03	1	trehalose	Escherichia coli metabolite; geroprotector; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
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.	2.1	1	pyrrole; secondary amine
oxazoles Oxazoles: Five-membered heterocyclic ring structures containing an oxygen in the 1-position and a nitrogen in the 3-position, in distinction from ISOXAZOLES where they are at the 1,2 positions.. 1,3-oxazole : A five-membered monocyclic heteroarene that is an analogue of cyclopentadiene with O in place of CH2 at position 1 and N in place of CH at position 3.. oxazole : An azole based on a five-membered heterocyclic aromatic skeleton containing one N and one O atom.	2.08	1	1,3-oxazoles; mancude organic heteromonocyclic parent; monocyclic heteroarene
cuprizone [no description available]	2.15	1	organonitrogen compound; organooxygen compound
hematoxylin Hematoxylin: A dye obtained from the heartwood of logwood (Haematoxylon campechianum Linn., Leguminosae) used as a stain in microscopy and in the manufacture of ink.	2.05	1	organic heterotetracyclic compound; oxacycle; polyphenol; tertiary alcohol	histological dye; plant metabolite
2,2-bis(bromomethyl)-1,3-propanediol 2,2-bis(bromomethyl)-1,3-propanediol: structure given in first source	2.04	1	primary alcohol
mannose mannopyranose : The pyranose form of mannose.	2.02	1	D-aldohexose; D-mannose; mannopyranose	metabolite
dideoxyadenosine Dideoxyadenosine: A dideoxynucleoside compound in which the 3'-hydroxy group on the sugar moiety has been replaced by a hydrogen. This modification prevents the formation of phosphodiester linkages which are needed for the completion of nucleic acid chains. The compound is an inhibitor of HIV replication, acting as a chain-terminator of viral DNA by binding to reverse transcriptase. Its principal side effect is nephrotoxicity. In vivo, dideoxyadenosine is rapidly metabolized to DIDANOSINE (ddI) by enzymatic deamination; ddI is then converted to dideoxyinosine monophosphate and ultimately to dideoxyadenosine triphosphate, the putative active metabolite.	2.1	1	adenosines; purine 2',3'-dideoxyribonucleoside	EC 3.5.4.4 (adenosine deaminase) inhibitor; EC 4.6.1.1 (adenylate cyclase) inhibitor
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.	3.14	5	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
glutamic acid Glutamic Acid: A non-essential amino acid naturally occurring in the L-form. Glutamic acid is the most common excitatory neurotransmitter in the CENTRAL NERVOUS SYSTEM.. glutamic acid : An alpha-amino acid that is glutaric acid bearing a single amino substituent at position 2.	2.44	2	glutamic acid; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	Escherichia coli metabolite; ferroptosis inducer; micronutrient; mouse metabolite; neurotransmitter; nutraceutical
miglustat miglustat: a glucosylceramide synthase inhibitor. miglustat : A hydroxypiperidine that is deoxynojirimycin in which the amino hydrogen is replaced by a butyl group.	2.55	2	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.	1.97	1	indolizidine alkaloid	antineoplastic agent; EC 3.2.1.114 (mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase) inhibitor; immunological adjuvant; plant metabolite
2',5'-dideoxyadenosine [no description available]	2.1	1	deoxyribonucleoside
chlorosulfonyl isocyanate chlorosulfonyl isocyanate: structure in first source	2.03	1
fagomine fagomine: structure in first source	2.11	1	piperidines
mor-14 N-methyldeoxynojirimycin: glucosidase inhibitor	2.41	1	hydroxypiperidine; piperidine alkaloid; tertiary amino compound	anti-HIV agent; cardioprotective agent; EC 3.2.1.20 (alpha-glucosidase) inhibitor; plant metabolite
arabitol arabitol: RN given refers to cpd without isomeric designation. arabinitol : A pentitol that is the sugar alcohol produced by the reduction of arabinose or lyxose. It is found in serum or urine of human infected with Candida albicans.. D-arabinitol : The D-enantiomer of arabinitol.	2.6	1	arabinitol
3,4-dehydroproline 3,4-dehydroproline: RN given refers to cpd without stereoisomeric designation	1.98	1
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
deoxyglucose Deoxyglucose: 2-Deoxy-D-arabino-hexose. An antimetabolite of glucose with antiviral activity.. deoxyglucose : A deoxyhexose comprising glucose having at least one hydroxy group replaced by hydrogen.	2.5	2
ribonolactone ribonolactone: structure given in first source; RN given refers to cpd without isomeric designation. D-ribono-1,4-lactone : A five-membered form of ribonolactone having D-configuration.	1.98	1	butan-4-olide; ribonolactone	metabolite
deoxyfuconojirimycin deoxyfuconojirimycin: structure given in first source. 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.	2.41	1	hydroxypiperidine; triol	fungal metabolite
2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine 2,5-dihydroxymethyl-3,4-dihydroxypyrrolidine: structure given in first source	2.04	1	dihydroxypyrrolidine
proline Proline: A non-essential amino acid that is synthesized from GLUTAMIC ACID. It is an essential component of COLLAGEN and is important for proper functioning of joints and tendons.. proline : An alpha-amino acid that is pyrrolidine bearing a carboxy substituent at position 2.	1.98	1	amino acid zwitterion; glutamine family amino acid; L-alpha-amino acid; proline; proteinogenic amino acid	algal metabolite; compatible osmolytes; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical; Saccharomyces cerevisiae metabolite
n-acetylglucopyranosylamine N-acetylglucopyranosylamine: structure given in first source	2.01	1
australine australine: RN & structure given in first source; inhibits amyloglucosidase & glycoprotein processing	2.21	1
glycogen glycogen : A polydisperse, highly branched glucan composed of chains of D-glucopyranose residues in alpha(1->4) glycosidic linkage, joined together by alpha(1->6) glycosidic linkages. A small number of alpha(1->3) glycosidic linkages and some cumulative alpha(1->6) links also may occur. The branches in glycogen typically contain 8 to 12 glucose residues.	4.18	16
arabinose [no description available]	6.39	51	L-arabinose	Escherichia 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.	2.69	3	D-glucosamine	Escherichia coli metabolite; geroprotector; mouse metabolite
monensin Monensin: An antiprotozoal agent produced by Streptomyces cinnamonensis. It exerts its effect during the development of first-generation trophozoites into first-generation schizonts within the intestinal epithelial cells. It does not interfere with hosts' development of acquired immunity to the majority of coccidial species. Monensin is a sodium and proton selective ionophore and is widely used as such in biochemical studies.. monensin A : A spiroketal, monensin A is the major component of monensin, a mixture of antibiotic substances produced by Streptomyces cinnamonensis. An antiprotozoal, it is used as the sodium salt as a feed additive for the prevention of coccidiosis in poultry and as a growth promoter in cattle.	2.08	1	cyclic hemiketal; monocarboxylic acid; polyether antibiotic; spiroketal	antifungal agent; coccidiostat; ionophore
miglitol [no description available]	2.07	1	piperidines
lentiginosine lentiginosine: from Astragalus lentiginosus	2.03	1	indolizines
ao 128 AO 128: alpha-glucosidase inhibitor; structure given in first source	2.07	1	organic molecular entity
acarbose [no description available]	2.07	1	amino cyclitol; glycoside
cp 320626 CP 320626: structure in first source	2.42	2
2,5-dideoxy-2,5-imino-d-glucitol 2,5-dideoxy-2,5-imino-D-glucitol: structure in first source	2.04	1
cocaine Cocaine: An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.. cocaine : A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.	2.53	2	benzoate ester; methyl ester; tertiary amino compound; tropane alkaloid	adrenergic uptake inhibitor; central nervous system stimulant; dopamine uptake inhibitor; environmental contaminant; local anaesthetic; mouse metabolite; plant metabolite; serotonin uptake inhibitor; sodium channel blocker; sympathomimetic agent; vasoconstrictor agent; xenobiotic
1,4-dideoxy-1,4-iminoarabinitol, (2r-(2alpha,3beta,4beta))-isomer [no description available]	2.04	1	pyrrolidines
isofagomine [no description available]	2.17	1	piperidines
1,4-dideoxy-1,4-imino-d-arabinitol [no description available]	3.06	4
chlorogenic acid caffeoylquinic acid: Antiviral Agent; structure in first source. chlorogenate : A monocarboxylic acid anion that is the conjugate base of chlorogenic acid; major species at pH 7.3.	2.02	1	cinnamate ester; tannin	food component; plant metabolite
krn 7000 KRN 7000: has an alpha-galactosylceramide structure; structure given in first source. alpha-galactosylceramide : A galactosylceramide in which the galactosyl residue has alpha anomeric conofiguration.. 1-O-(alpha-D-galactosyl)-N-hexacosanoylphytosphingosine : A glycophytoceramide having an alpha-D-galactosyl residue at the O-1 position and a hexacosanoyl group attached to the nitrogen.	2.03	1	glycophytoceramide; N-acyl-beta-D-galactosylphytosphingosine	allergen; antigen; antineoplastic agent; epitope; immunological adjuvant
4-amino-4-deoxyarabinose [no description available]	1.97	1
quercetin [no description available]	2.03	1	7-hydroxyflavonol; pentahydroxyflavone	antibacterial agent; antineoplastic agent; antioxidant; Aurora kinase inhibitor; chelator; EC 1.10.99.2 [ribosyldihydronicotinamide dehydrogenase (quinone)] inhibitor; geroprotector; phytoestrogen; plant metabolite; protein kinase inhibitor; radical scavenger
deoxyribose [no description available]	1.99	1	deoxypentose	human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite
salacinol salacinol: a sulfated thiosugar from Salacia reticulata (CELASTRACEAE); structure in first source	2.04	1
allosamine allosamine: structure in first source	2.03	1
cp 91149 CP 91149: inhibits liver glycogen phosphorylase; structure in first source	2.01	1
muromonab-cd3 xestospongin C: was indexed to xestospongin A; from Xestospongia sponge; empties the ER calcium store but does not inhibit InsP3-induced Ca2+ release. xestospongin C : An organic heteropentacyclic compound that is isolated from the marine sponge Xestospongia exigua.	2.08	1	alkaloid; macrocycle; organic heteropentacyclic compound; organonitrogen heterocyclic compound; oxacycle; tertiary amino compound	antineoplastic agent; EC 2.7.10.1 (receptor protein-tyrosine kinase) inhibitor; IP3 receptor antagonist; marine metabolite
casuarine casuarine: structure in first source; do not confuse with tannin casuariin	2.1	1
lipid a Lipid A: Lipid A is the biologically active component of lipopolysaccharides. It shows strong endotoxic activity and exhibits immunogenic properties.. lipid A : The glycolipid moiety of bacterial lipopolysaccharide (R can be either hydrogen or a fatty acyl group).	1.97	1	dodecanoate ester; lipid A; tetradecanoate ester	Escherichia coli metabolite
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).	2.13	1	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
ribose ribopyranose : The pyranose form of ribose.	1.98	1	D-ribose; ribopyranose
glucagon Glucagon: A 29-amino acid pancreatic peptide derived from proglucagon which is also the precursor of intestinal GLUCAGON-LIKE PEPTIDES. Glucagon is secreted by PANCREATIC ALPHA CELLS and plays an important role in regulation of BLOOD GLUCOSE concentration, ketone metabolism, and several other biochemical and physiological processes. (From Gilman et al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 9th ed, p1511). glucagon : A 29-amino acid peptide hormone consisting of His, Ser, Gln, Gly, Thr, Phe, Thr, Ser, Asp, Tyr, Ser, Lys, Tyr, Leu, Asp, Ser, Arg, Arg, Ala, Gln, Asp, Phe, Val, Gln, Trp, Leu, Met, Asn and Thr residues joined in sequence.	2.92	4	peptide hormone
glycolipids [no description available]	1.97	1
neosalacinol [no description available]	2.04	1
phenyliminoribitol phenyliminoribitol: inhibits inosine-guanosine hydrolase; structure given in first source	1.99	1
inosine [no description available]	2.39	2	inosines; purines D-ribonucleoside	Escherichia coli metabolite; human metabolite; mouse metabolite; Saccharomyces cerevisiae metabolite

Condition	Relationship Strength	Studies
Hyperglycemia, Postprandial Abnormally high BLOOD GLUCOSE level after a meal.	2.07	1
Hyperglycemia Abnormally high BLOOD GLUCOSE level.	2.07	1
Acid beta-Glucosidase Deficiency [description not available]	2.13	1
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.	2.13	1
Acid Alpha-Glucosidase Deficiency [description not available]	2.41	1
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)	2.41	1
Pain, Chronic [description not available]	2.31	1
Disease Models, Animal Naturally-occurring or experimentally-induced animal diseases with pathological processes analogous to human diseases.	2.49	2
Chronic Pain Aching sensation that persists for more than a few months. It may or may not be associated with trauma or disease, and may persist after the initial injury has healed. Its localization, character, and timing are more vague than with acute pain.	2.31	1
Anoxemia [description not available]	2.1	1
Hypoxia Sub-optimal OXYGEN levels in the ambient air of living organisms.	2.1	1
Recrudescence [description not available]	2.13	1
Cocaine Abuse [description not available]	2.53	2
Cocaine-Related Disorders Disorders related or resulting from use of cocaine.	2.53	2
Clinically Isolated CNS Demyelinating Syndrome [description not available]	2.15	1
Demyelinating Diseases Diseases characterized by loss or dysfunction of myelin in the central or peripheral nervous system.	2.15	1
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)	2.01	1
Alloxan Diabetes [description not available]	2.01	1
Diabetes Mellitus, Adult-Onset [description not available]	2.7	3
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.	2.7	3

1,4-dideoxy-1,4-iminoarabinitol

Description

Cross-References

Synonyms (25)

Research Excerpts

Pharmacokinetics

Bioavailability

Dosage Studied

Protein Targets (9)

Inhibition Measurements

Biological Processes (8)

Molecular Functions (17)

Ceullar Components (15)

Bioassays (35)

Research

Studies (57)

Market Indicators

Research Demand Index: 11.34

Study Types

1,4-dideoxy-1,4-iminoarabinitol

Description

Cross-References

Synonyms (25)

Research Excerpts

Pharmacokinetics

Bioavailability

Dosage Studied

Protein Targets (9)

Inhibition Measurements

Biological Processes (8)

Molecular Functions (17)

Ceullar Components (15)

Bioassays (35)

Research

Studies (57)

Market Indicators

Research Demand Index: 11.34

Study Types

Related Drugs (70)

Related Conditions (20)