NOJIRIMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H13NO5
Molecular Weight	179.1714
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

N[C@H](CO)[C@@H](O)[C@H](O)[C@@H](O)C=O

InChI

InChIKey=KLXQAXYSOJNJRI-JGWLITMVSA-N

InChI=1S/C6H13NO5/c7-3(1-8)5(11)6(12)4(10)2-9/h2-6,8,10-12H,1,7H2/t3-,4+,5-,6-/m1/s1

HIDE SMILES / InChI

Molecular Formula	C6H13NO5
Molecular Weight	179.1714
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Approval Year

PubMed

Title	Date	PubMed
A Fluorescent sp2-iminosugar with pharmacological chaperone activity for gaucher disease: synthesis and intracellular distribution studies.	2010-11-22	21064079
Fluorescent-tagged sp2-iminosugars with potent β-glucosidase inhibitory activity.	2010-11-01	20889348
(3R,3aS,6R,6aR)-3-(1-Nitro-eth-yl)perhydro-furo[3,2-b]furan-3,6-diol.	2010-06-18	21587924
Glycosidase inhibition: assessing mimicry of the transition state.	2010-01-21	20066263
{6-[2,5-Bis(chloro-meth-yl)-3,4-dihydroxy-tetra-hydro-furan-2-yl-oxy]-3-chloro-4,5-dihydr-oxy-3,4,5,6-tetra-hydro-2H-pyran-2-yl}methyl acetate dihydrate.	2009-12-16	21580053
Chaperone activity of bicyclic nojirimycin analogues for Gaucher mutations in comparison with N-(n-nonyl)deoxynojirimycin.	2009-11-23	19830760
Phylogenetics of an antibiotic producing Streptomyces strain isolated from soil.	2009-09-05	20198168
Metabolic engineering strategies for the improvement of cellulase production by Hypocrea jecorina.	2009-09-01	19723296
Inhibitory Effects of Partially Decomposed Alginate on Production of Glucan and Organic Acid by Streptococcus sobrinus 6715.	2009-05	19430617
An expeditious one-pot synthesis of 1,6-dideoxy-N-alkylated nojirimycin derivatives and their inhibitory effects on the secretion of IFN-gamma and IL-4.	2008-02-15	18060793
Synthesis and biological evaluation of a small library of nojirimycin-derived bicyclic iminosugars.	2007-09-03	17477911
[Iminosugars: current and future therapeutic applications].	2007-01	17299348
1,3-Dideoxynojirimycin-3-yl glycosides of beta-(1-->3)- and beta-(1-->6)-linked gluco-oligosaccharides.	2006-09-04	16750183
Reduced inflammatory potential of peritoneal macrophages recruited in mice pretreated with a glycolipid synthesis inhibitor.	2006-08	16983496
Synthesis and biological evaluation of glycosidase inhibitors: gem-difluoromethylenated nojirimycin analogues.	2006-05-18	16686540
Isolation and structure assignment of an iminotetrasaccharide from a cultured filamentous cyanobacterium Anabaena sp.	2006-03	16562836
A Madagascar Sponge Batzella sp. as a source of alkylated iminosugars.	2005-01	15679333
Asymmetric dihydroxylation of d-glucose derived alpha,beta-unsaturated ester: synthesis of azepane and nojirimycin analogues.	2004-07-09	15230599
Antiamylase-pullulanase enzyme monoclonals which specifically inhibit amylase or pullulanase activity.	2004-01-15	14984202
Glycosidase inhibitors: update and perspectives on practical use.	2003-10	12851286
General access to iminosugar C-glycoside building blocks by means of cross-metathesis: a gateway to glycoconjugate mimetics.	2003-09-04	12943404
gem-Diamine 1-N-iminosugars and related iminosugars, candidate of therapeutic agents for tumor metastasis.	2003	12570867
A general strategy for the practical synthesis of nojirimycin C-glycosides and analogues. Extension to the first reported example of an iminosugar 1-phosphonate.	2002-10-04	12353989
Imino sugars that are less toxic but more potent as antivirals, in vitro, compared with N-n-nonyl DNJ.	2002-09	12630678
1,5-Anhydro-D-fructose; a versatile chiral building block: biochemistry and chemistry.	2002-05-13	12007470
Therapeutic applications of sugar-mimicking glycosidase inhibitors.	2001-07	12374106
Noeuromycin, a glycosyl cation mimic that strongly inhibits glycosidases.	2001-05-30	11457350

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:42:53 GMT 2025` Edited by `admin` on `Mon Mar 31 22:42:53 GMT 2025`
Record UNII	W40512EP9K
Record Status	`FAILED`
Record Version

Download

Name

Type

Language

NOJIRIMYCIN

Common Name

English

R-468

Preferred Name

English

5-AMINO-5-DEOXY-D-GLUCOPYRANOSE

Common Name

English

(+)-NOJIRIMYCIN

Common Name

English

2,3,4,5-PIPERIDINETETROL, 6-(HYDROXYMETHYL)-, (3R,4S,5R,6R)-

Systematic Name

English

U-51640

Code

English

(3R,4S,5R,6R)-6-(HYDROXYMETHYL)PIPERIDINE-2,3,4,5-TETRAOL

Systematic Name

English

(2R,3S,4R,5R)-5-AMINO-2,3,4,6-TETRAHYDROXYHEXANAL

Systematic Name

English

Code System Code Type Description

EPA CompTox

DTXSID201028328