NOJIRIMYCIN

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H13NO5
Molecular Weight	179.1711
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	179.1711
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
Therapeutic applications of sugar-mimicking glycosidase inhibitors.	2001 Jul	12374106
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 Oct 4	12353989
Imino sugars that are less toxic but more potent as antivirals, in vitro, compared with N-n-nonyl DNJ.	2002 Sep	12630678
gem-Diamine 1-N-iminosugars and related iminosugars, candidate of therapeutic agents for tumor metastasis.	2003	12570867
Glycosidase inhibitors: update and perspectives on practical use.	2003 Oct	12851286
General access to iminosugar C-glycoside building blocks by means of cross-metathesis: a gateway to glycoconjugate mimetics.	2003 Sep 4	12943404
Antiamylase-pullulanase enzyme monoclonals which specifically inhibit amylase or pullulanase activity.	2004 Jan 15	14984202
Asymmetric dihydroxylation of d-glucose derived alpha,beta-unsaturated ester: synthesis of azepane and nojirimycin analogues.	2004 Jul 9	15230599
A Madagascar Sponge Batzella sp. as a source of alkylated iminosugars.	2005 Jan	15679333
Reduced inflammatory potential of peritoneal macrophages recruited in mice pretreated with a glycolipid synthesis inhibitor.	2006 Aug	16983496
Isolation and structure assignment of an iminotetrasaccharide from a cultured filamentous cyanobacterium Anabaena sp.	2006 Mar	16562836
Synthesis and biological evaluation of glycosidase inhibitors: gem-difluoromethylenated nojirimycin analogues.	2006 May 18	16686540
1,3-Dideoxynojirimycin-3-yl glycosides of beta-(1-->3)- and beta-(1-->6)-linked gluco-oligosaccharides.	2006 Sep 4	16750183
[Iminosugars: current and future therapeutic applications].	2007 Jan	17299348
Synthesis and biological evaluation of a small library of nojirimycin-derived bicyclic iminosugars.	2007 Sep 3	17477911
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 Feb 15	18060793
{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 Dec 16	21580053
Inhibitory Effects of Partially Decomposed Alginate on Production of Glucan and Organic Acid by Streptococcus sobrinus 6715.	2009 May	19430617
Chaperone activity of bicyclic nojirimycin analogues for Gaucher mutations in comparison with N-(n-nonyl)deoxynojirimycin.	2009 Nov 23	19830760
Metabolic engineering strategies for the improvement of cellulase production by Hypocrea jecorina.	2009 Sep 1	19723296
Phylogenetics of an antibiotic producing Streptomyces strain isolated from soil.	2009 Sep 5	20198168
Glycosidase inhibition: assessing mimicry of the transition state.	2010 Jan 21	20066263
(3R,3aS,6R,6aR)-3-(1-Nitro-eth-yl)perhydro-furo[3,2-b]furan-3,6-diol.	2010 Jun 18	21587924
Fluorescent-tagged sp2-iminosugars with potent β-glucosidase inhibitory activity.	2010 Nov 1	20889348
A Fluorescent sp2-iminosugar with pharmacological chaperone activity for gaucher disease: synthesis and intracellular distribution studies.	2010 Nov 22	21064079

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:32:47 GMT 2023` Edited by `admin` on `Sat Dec 16 09:32:47 GMT 2023`
Record UNII	W40512EP9K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NOJIRIMYCIN

Common 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

R-468

Code

English

Code System Code Type Description

EPA CompTox

DTXSID201028328