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CHEBI:191195 - mannostatin A

ChEBI IDCHEBI:191195
ChEBI Namemannostatin A
Stars
DefinitionAn 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.
Secondary ChEBI IDCHEBI:44106
Last Modified21 April 2022
SubmitterAdnan
DownloadsMolfile
FormulaC6H13NO3S
Net Charge0
Average Mass179.241
Monoisotopic Mass179.06161
SMILESCS[C@@H]1[C@@H](N)[C@@H](O)[C@@H](O)[C@H]1O
InChIInChI=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
InChIKeyBLOFGONIVNXZME-YDMGZANHSA-N
Species of MetaboliteComponentSourceComments
Streptoverticillium verticillium subsp. quintum (ncbitaxon:1433418) - PubMed (2737947) Strain: ME3-AG3
Roles Classification
Biological Roles:
bacterial metabolite  Any prokaryotic metabolite produced during a metabolic reaction in bacteria.
EC 3.2.1.24 (alpha-mannosidase) inhibitor  An EC 3.2.1.* (glycosidase) inhibitor that interferes with the action of α-mannosidase (EC 3.2.1.24).
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-α-mannosidase (EC 3.2.1.114), a key enzyme target in the development of anti-cancer therapies.
ChEBI Ontology
Outgoing Relation(s)
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  Source
(1R,2R,3R,4S,5R)-4-amino-5-(methylthio)cyclopentane-1,2,3-triolPDBeChem
mannostatinChemIDplus
(+)-mannostatin AKNApSAcK
(1R,2R,3R,4S,5R)-4-amino-5-(methylthio)-1,2,3-cyclopentanetriolChEBI
Manual XrefsDatabases
MSNPDBeChem
C00017678KNApSAcK
110651ChemSpider
Registry NumbersSources
Reaxys:4781487Reaxys
CAS:102822-56-0ChemIDplus
Citations