mannostatin A: structure given in first source; isolated from Streptoverticillium verticilllus [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
mannostatin A : An amino cyclitol that is cyclopentane substituted by hydroxy groups at positions 1, 2 and 3, by an amino group at positon 4, and by a methylsulfanediyl group at position 5 (the 1R,2R,3R,4S,5R-stereoisomer). It is isolated from the soil bacterium Streptoverticillium verticillium. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 124189 |
| CHEMBL ID | 9623 |
| CHEBI ID | 191195 |
| MeSH ID | M0167076 |
| Synonym |
|---|
| mannostatin a, 1 |
| mannostatin a, 1a |
| (1r,2r,3r,4s,5r)-4-amino-5-methylsulfanyl-cyclopentane-1,2,3-triol |
| bdbm50078117 |
| 1,2,3-cyclopentanetriol, 4-amino-5-(methylthio)- |
| mannostatin |
| brn 4781487 |
| 1,2,3-cyclopentanetriol, 4-amino-5-(methylthio)-, (1r-(1-alpha,2-alpha,3-alpha,4-alpha,5-beta))- |
| 4-amino-5-methylthio-1,2,3-cyclopentanetriol |
| mannostatin a |
| MSN , |
| (1r,2r,3r,4s,5r)-4-amino-5-(methylthio)cyclopentane-1,2,3-triol |
| 2F7O |
| CHEMBL9623 , |
| (1r,2r,3r,4s,5r)-4-amino-5-methylsulfanylcyclopentane-1,2,3-triol |
| (1r,2r,3r,4s,5r)-4-amino-5-(methylthio)-1,2,3-cyclopentanetriol |
| 102822-56-0 |
| CHEBI:191195 |
| (1r,2r,3r,4s,5r)-4-amino-5-(methylsulfanyl)cyclopentane-1,2,3-triol |
| (+)-mannostatin a |
| mannostatin a hydrochloride |
| Q27463542 |
| 4-amino-5-(methylsulfanyl)cyclopentane-1,2,3-triol |
| DTXSID20908059 |
Mannostatin A is a potent inhibitor of the mannose-trimming enzyme, Golgi alpha-mannosidase II (GMII) GMII acts late in the N-glycan processing pathway.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Mannostatin A is a potent inhibitor of the mannose-trimming enzyme, Golgi alpha-mannosidase II (GMII), which acts late in the N-glycan processing pathway. " | ( The molecular basis of inhibition of Golgi alpha-mannosidase II by mannostatin A. Boons, GJ; Guo, J; Kuntz, DA; Rose, DR; Zhong, W, 2009) | 2.03 |
| "Mannostatin A is a metabolite produced by the microorganism Streptoverticillium verticillus and reported to be a potent competitive inhibitor of rat epididymal alpha-mannosidase. " | ( Mannostatin A, a new glycoprotein-processing inhibitor. Aoyagi, T; Elbein, AD; Kaushal, GP; Mitchell, M; Molyneux, RJ; Pastuszak, I; Tropea, JE, 1990) | 3.16 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "Mannostatin A did not inhibit the growth of either cell line at the concentration effective to inhibit invasion." | ( Inhibition of tumor cell invasion in the Boyden chamber assay by a mannosidase inhibitor, mannostatin A. Aoyagi, T; Atsumi, S; Ochi, Y; Umezawa, K, ) | 1.07 |
| Excerpt | Reference | Relevance |
|---|---|---|
| "Mannostatin A-treated B16/F10 cells also showed decreased metastatic activity in vivo in C57Bl/6 mice." | ( Inhibition of tumor cell invasion in the Boyden chamber assay by a mannosidase inhibitor, mannostatin A. Aoyagi, T; Atsumi, S; Ochi, Y; Umezawa, K, ) | 1.07 |
| Role | Description |
|---|---|
| EC 3.2.1.24 (alpha-mannosidase) inhibitor | An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of alpha-mannosidase (EC 3.2.1.24). |
| bacterial metabolite | Any prokaryotic metabolite produced during a metabolic reaction in bacteria. |
| EC 3.2.1.114 (mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase) inhibitor | An enzyme inhibitor that interferes with the action of mannosyl-oligosaccharide 1,3-1,6-alpha-mannosidase (EC 3.2.1.114), a key enzyme target in the development of anti-cancer therapies. |
| [role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Class | Description |
|---|---|
| methyl sulfide | Any aliphatic sulfide in which at least one of the organyl groups attached to the sulfur is a methyl group. |
| triol | A chemical compound containing three hydroxy groups. |
| amino cyclitol | Any cyclitol having one or more alcoholic hydroxy groups replaced by substituted or unsubstituted amino groups. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| Chain A, alpha-mannosidase II | Drosophila melanogaster (fruit fly) | Ki | 0.0360 | 0.0360 | 0.0360 | 0.0360 | AID977610 |
| Chain A, alpha-mannosidase II | Drosophila melanogaster (fruit fly) | Ki | 0.0360 | 0.0360 | 0.0360 | 0.0360 | AID977610 |
| Mannosyl-oligosaccharide alpha-1,2-mannosidase IA | Drosophila melanogaster (fruit fly) | IC50 (µMol) | 0.1500 | 0.0050 | 0.0775 | 0.1500 | AID587706 |
| Alpha-mannosidase 2 | Drosophila melanogaster (fruit fly) | Ki | 0.0360 | 0.0030 | 0.0195 | 0.0360 | AID1799624 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Assay ID | Title | Year | Journal | Article |
|---|---|---|---|---|
| AID1799624 | Inhibition Assay from Article 10.1002/cbic.200800538: \\The molecular basis of inhibition of Golgi alpha-mannosidase II by mannostatin A.\\ | 2009 | Chembiochem : a European journal of chemical biology, Jan-26, Volume: 10, Issue:2 | The molecular basis of inhibition of Golgi alpha-mannosidase II by mannostatin A. |
| AID587708 | Inhibition of Drosophila melanogaster LM408 by spectrophotometry | 2011 | European journal of medicinal chemistry, Mar, Volume: 46, Issue:3 | α-D-mannose derivatives as models designed for selective inhibition of Golgi α-mannosidase II. |
| AID587706 | Inhibition of Drosophila melanogaster GM2b by spectrophotometry | 2011 | European journal of medicinal chemistry, Mar, Volume: 46, Issue:3 | α-D-mannose derivatives as models designed for selective inhibition of Golgi α-mannosidase II. |
| AID35255 | Compound was tested for the inhibitory activity against alpha-mannosidase | 1999 | Bioorganic & medicinal chemistry letters, Jun-07, Volume: 9, Issue:11 | Synthesis and biological evaluation of alpha-mannosidase inhibitory activity of three deoxy derivatives of mannostatin A. |
| AID35236 | Inhibitory activity against Alpha-mannosidase (Jack bean) | 2000 | Bioorganic & medicinal chemistry letters, May-15, Volume: 10, Issue:10 | Synthesis of a potent aminocyclitol alpha-mannosidase inhibitor, 1L-(1,2,3,5/4)-5-amino-4-O-methyl-1,2,3,4-cyclopentanetetrol. |
| AID977610 | Experimentally measured binding affinity data (Ki) for protein-ligand complexes derived from PDB | 2006 | Journal of the American Chemical Society, Jun-28, Volume: 128, Issue:25 | Structural basis of the inhibition of Golgi alpha-mannosidase II by mannostatin A and the role of the thiomethyl moiety in ligand-protein interactions. |
| AID1811 | Experimentally measured binding affinity data derived from PDB | 2006 | Journal of the American Chemical Society, Jun-28, Volume: 128, Issue:25 | Structural basis of the inhibition of Golgi alpha-mannosidase II by mannostatin A and the role of the thiomethyl moiety in ligand-protein interactions. |
| [information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 2 (13.33) | 18.7374 |
| 1990's | 5 (33.33) | 18.2507 |
| 2000's | 7 (46.67) | 29.6817 |
| 2010's | 1 (6.67) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.
| This Compound (11.83) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 1 (6.25%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 15 (93.75%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||