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
Noeuromycin, a glycosyl cation mimic that strongly inhibits glycosidases.	2001 May 30	11457350
1,5-Anhydro-D-fructose; a versatile chiral building block: biochemistry and chemistry.	2002 May 13	12007470
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
Glycosidase inhibitors: update and perspectives on practical use.	2003 Oct	12851286
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
{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
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 UTC 2023` Edited by `admin` on `Sat Dec 16 09:32:47 UTC 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