Demannose

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H12O6
Molecular Weight	180.1559
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OC[C@@H](O)[C@@H](O)[C@H](O)[C@H](O)C=O

InChI

InChIKey=GZCGUPFRVQAUEE-KVTDHHQDSA-N

InChI=1S/C6H12O6/c7-1-3(9)5(11)6(12)4(10)2-8/h1,3-6,8-12H,2H2/t3-,4-,5-,6-/m1/s1

HIDE SMILES / InChI

Description
Sources: http://www.douglaslabs.com/media/DL99471.pdf
Curator's Comment: description was created based on several sources, including http://www.rxlist.com/d-mannose-page2/supplements.htm | https://www.ncbi.nlm.nih.gov/pubmed/6753135 | https://www.ncbi.nlm.nih.gov/pubmed/9736238

D-mannose is a simple sugar found naturally in fruits such as cranberries and pineapples. Unlike many sugars, it is not metabolised or stored in the liver. Much of it is excreted in the urine, where it interferes with particle attachment and prevents certain kind of bacteria from sticking to the walls and causing infection. Mannose supplement is also indicated for treatment of carbohydrate-deficient glycoprotein syndrome, however clinical trials failed to prove its efficacy.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Adhesin protein fimH 1 Target ID: CHEMBL4837 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15659162	Inhibitor 8297		2300.0 nM [Kd]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Urinary tract infections 205 Sources: http://www.rxlist.com/d-mannose-page2/supplements.htm	Curative		Approved 8429	D-MANNOSE Approved Use D-mannose may be a useful dietary supplement for individuals wishing to support normal urinary tract health
Carbohydrate-deficient glycoprotein syndrome 1 Sources: http://www.rxlist.com/d-mannose-page2/supplements.htm	Primary		Approved 8429	D-MANNOSE Approved Use D-mannose is used for treating carbohydrate-deficient glycoprotein syndrome, an inherited metabolic disorder.

PubMed

Title	Date	PubMed
Concanavalin A binding glycoprotein in human stratum corneum.	1984 Mar	6421939
Relationships between glucose and mannose during late gestation in normal pregnancy and pregnancy complicated by diabetes mellitus: concurrent concentrations in maternal plasma and amniotic fluid.	1986 May	3958133
Inhibition of cyclic AMP-dependent induction of ornithine aminotransferase by simple carbohydrates in cultured hepatocytes.	1987 Dec	2827574
Intravenous administration of phosphorylated acid alpha-glucosidase leads to uptake of enzyme in heart and skeletal muscle of mice.	1991 Feb	1991835
Automated screening of urine samples for carbohydrates, organic and amino acids after treatment with urease.	1991 Jan 2	2026685
Upregulation of GLUT2 mRNA by glucose, mannose, and fructose in isolated rat hepatocytes.	1992 Jan	1727734
Isolation and characterization of the mannose receptor from human liver potentially involved in the plasma clearance of tissue-type plasminogen activator.	1992 Jul	1618483
Anti-pig IgM antibodies in human serum react predominantly with Gal(alpha 1-3)Gal epitopes.	1993 Dec 1	7504304
Deficiency of UDP-GlcNAc:Dolichol Phosphate N-Acetylglucosamine-1 Phosphate Transferase (DPAGT1) causes a novel congenital disorder of Glycosylation Type Ij.	2003 Aug	12872255
Oolemmal proteomics--identification of highly abundant heat shock proteins and molecular chaperones in the mature mouse egg and their localization on the plasma membrane.	2003 Feb 14	12646049
Mannose-Escherichia coli interaction in the presence of metal cations studied in vitro by colorimetric polydiacetylene/glycolipid liposomes.	2004 Jun	15149798
Functional evaluation of carbohydrate-centred glycoclusters by enzyme-linked lectin assay: ligands for concanavalin A.	2004 Jun 7	15174159
Synthesis, characterization, and bioavailability of mannosylated shell cross-linked nanoparticles.	2004 May-Jun	15132680
Dendritic cells and vascular endothelial growth factor in colorectal cancer: correlations with clinicobiological findings.	2005	16015045
Acid sphingomyelinase: relation of 93lysine residue on the ratio of intracellular to secreted enzyme activity.	2005 Aug	15997205
Mannose binding lectin genotypes influence recovery from hepatitis B virus infection.	2005 Jul	15994813
Inefficient maturation of the rat luteinizing hormone receptor. A putative way to regulate receptor numbers at the cell surface.	2005 Jul 15	15901736
Carbohydrate localization on Gyrodactylus salaris and G. derjavini and corresponding carbohydrate binding capacity of their hosts Salmo salar and S. trutta.	2005 Mar	15831112
Synthesis of structurally defined scaffolds for bivalent ligand display based on glucuronic acid anilides. The degree of tertiary amide isomerism and folding depends on the configuration of a glycosyl azide.	2005 May 13	15876103
Innate immunity: cells, receptors, and signaling pathways.	2005 May-Jun	15995585
Synthesis and transdermal penetration of NSAID glycoside esters.	2005 Sep 14	16061334
Phosphatidylinositol mannosides: synthesis and suppression of allergic airway disease.	2006 Aug 15	16697208
Analysis of rice glycosyl hydrolase family 1 and expression of Os4bglu12 beta-glucosidase.	2006 Dec 29	17196101
Search for additional influenza virus to cell interactions.	2006 Feb	16575529
Catabolism of 1,5-anhydro-D-fructose in Sinorhizobium morelense S-30.7.5: discovery, characterization, and overexpression of a new 1,5-anhydro-D-fructose reductase and its application in sugar analysis and rare sugar synthesis.	2006 Feb	16461673
Synthesis of a nonavalent mannoside glycodendrimer based on pentaerythritol.	2006 Feb 17	16468786
Oral ingestion of mannose alters the expression level of deaminoneuraminic acid (KDN) in mouse organs.	2006 Jul	16897182
Ablation of mouse phosphomannose isomerase (Mpi) causes mannose 6-phosphate accumulation, toxicity, and embryonic lethality.	2006 Mar 3	16339137
Genomic and metabolic studies of the impact of probiotics on a model gut symbiont and host.	2006 Nov	17132046
Evaluation of the carbohydrate recognition domain of the bacterial adhesin FimH: Design, synthesis and binding properties of mannoside ligands.	2006 Nov 7	17047870
The affinity of the FimH fimbrial adhesin is receptor-driven and quasi-independent of Escherichia coli pathotypes.	2006 Sep	16930149
Design and synthesis of novel multivalent mannosides targeting the mannose receptor.	2007 Dec 28	17880930
Engineering of PA-IIL lectin from Pseudomonas aeruginosa - Unravelling the role of the specificity loop for sugar preference.	2007 Jun 1	17540045
Multi-mannosides based on a carbohydrate scaffold: synthesis, force field development, molecular dynamics studies, and binding affinities for lectin Con A.	2007 Nov 23	17979282
Composition and hierarchical organisation of a spider silk.	2007 Oct 3	17912375
Intervening with urinary tract infections using anti-adhesives based on the crystal structure of the FimH-oligomannose-3 complex.	2008 Apr 30	18446213
Tetra- and hexavalent mannosides inhibit the pro-apoptotic, antiproliferative and cell surface clustering effects of concanavalin-A: impact on MT1-MMP functions in marrow-derived mesenchymal stromal cells.	2008 Feb	18065811
Role of antibody paratope conformational flexibility in the manifestation of molecular mimicry.	2008 Feb 15	18032557
EmbA is an essential arabinosyltransferase in Mycobacterium tuberculosis.	2008 Jan	18174142
Identification of hexose diastereomers by means of tandem mass spectrometry of oxocarbenium ions followed by neural networks analysis.	2008 Jan	17968854
Metal-activated C-peptide facilitates glucose clearance and the release of a nitric oxide stimulus via the GLUT1 transporter.	2008 Jan	17965850
Mannoside hydrolysis: it's a boat!	2008 May	18421282
Colon cancer releases alpha-tocopherol from its O-glycosides better than normal colon tissue.	2009 Mar-Apr	19579594
In vivo expression of innate immunity markers in patients with Mycobacterium tuberculosis infection.	2010 Aug 18	20718957
Taurolidine antiadhesive properties on interaction with E. coli; its transformation in biological environment and interaction with bacteria cell wall.	2010 Jan 28	20126631
Structure-based drug design and optimization of mannoside bacterial FimH antagonists.	2010 Jun 24	20507142
Escherichia coli global gene expression in urine from women with urinary tract infection.	2010 Nov 11	21085611
Crystal structures of a novel anti-HIV mannose-binding lectin from Polygonatum cyrtonema Hua with unique ligand-binding property and super-structure.	2010 Sep	20546901

Patents

Sample Use Guides

In Vivo Use Guide

3 x 1000mg tablets every three hours for a couple of days plus a middle of the night dose is a good guide for most people who need urgent support. Reduce slowly as symptoms improve.

Route of Administration: Oral

In Vitro Use Guide

Two rows of serial two fold dilutions of bacterial suspension in PBS were dispensed in microtiter plates. To each well in the first row an aliquot of a yeast suspension was added; to each raw in the second row an aliquote of washed 3% human group A erythrocytes was added. The plates were gently shaken. Yeast agglutination was scored after 30 min at room temperature, hemagglutination was assessed after the plates were kept overnight at 4°C. To establish whether the agglutination was mannose sensitive or mannose resistant, the bacteria 10^9 cells/ml were suspended in PBS containing 2.5 % methyl alpha-D-mannoside prior to the assay.

Name

Type

Language

MANNOSE

Preferred Name

English

Demannose

Official Name

English

MANNOSE, D-

Preferred Name

English

NSC-26247

Code

English

demannose [INN]

Common Name

English

DEMANNOSE [USAN]

Common Name

English

D-mannose [WHO-DD]

Common Name

English

SEMINOSE

Common Name

English

CARUBINOSE

Common Name

English

D-MANNOSE [MI]

Common Name

English

MANNOSE [VANDF]

Common Name

English

(2S,3S,4R,5R)-2,3,4,5,6-pentahydroxyhexanal

Systematic Name

English

D-MANNOSE

Systematic Name

English

MANNOSE [USP-RS]

Common Name

English

MANNOSE, D- [II]

Common Name

English

MANNOSE [INCI]

Common Name

English

CERC-802

Code

English

Classification Tree Code System Code

DSLD

2627 (Number of products:112)