CHEBI:191195 - mannostatin A

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ChEBI Name mannostatin A
ChEBI ID CHEBI:191195
Definition 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:44106
Supplier Information
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Formula C6H13NO3S
Net Charge 0
Average Mass 179.230
Monoisotopic Mass 179.06161
InChI InChI=1S/C6H13NO3S/c1-11-6-2(7)3(8)4(9)5(6)10/h2-6,8-10H,7H2,1H3/t2-,3+,4+,5+,6+/m0/s1
InChIKey BLOFGONIVNXZME-YDMGZANHSA-N
SMILES CS[C@@H]1[C@@H](N)[C@@H](O)[C@@H](O)[C@H]1O
Metabolite of Species Details
Streptoverticillium verticillium subsp. quintum (NCBI:txid1433418) of strain ME3-AG3 See: PubMed
Roles Classification
Biological Role(s): 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.
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ChEBI Ontology
Outgoing mannostatin A (CHEBI:191195) has role bacterial metabolite (CHEBI:76969)
mannostatin A (CHEBI:191195) has role EC 3.2.1.114 (mannosyl-oligosaccharide 1,3-1,6-α-mannosidase) inhibitor (CHEBI:65239)
mannostatin A (CHEBI:191195) has role EC 3.2.1.24 (α-mannosidase) inhibitor (CHEBI:191196)
mannostatin A (CHEBI:191195) is a amino cyclitol (CHEBI:61689)
mannostatin A (CHEBI:191195) is a methyl sulfide (CHEBI:86315)
mannostatin A (CHEBI:191195) is a triol (CHEBI:27136)
IUPAC Name
(1R,2R,3R,4S,5R)-4-amino-5-(methylsulfanyl)cyclopentane-1,2,3-triol
Synonyms Sources
(+)-mannostatin A KNApSAcK
(1R,2R,3R,4S,5R)-4-amino-5-(methylthio)-1,2,3-cyclopentanetriol ChEBI
(1R,2R,3R,4S,5R)-4-amino-5-(methylthio)cyclopentane-1,2,3-triol PDBeChem
mannostatin ChemIDplus
Manual Xrefs Databases
110651 ChemSpider
C00017678 KNApSAcK
MSN PDBeChem
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Registry Numbers Types Sources
102822-56-0 CAS Registry Number ChemIDplus
4781487 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
10386924 PubMed citation Europe PMC
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Last Modified
21 April 2022