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CHEBI:88050 - deoxycylindrospermopsin

ChEBI IDCHEBI:88050
ChEBI Namedeoxycylindrospermopsin
Stars
DefinitionA triazaacenaphthylene that is 2,2a,3,4,5,5a,6,7-octahydro-1H-1,8,8b-triazaacenaphthylene which is substituted at positions 3, 4, and 7 by methyl, sulfooxy, and (2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)methyl groups, respectively (the 2aS,3R,4S,5aS,7R stereoisomer). A non-toxic analogue of the cyanotoxins cylindrospermopsin and 7-epi-cylindrospermopsin (the latter two have a hydroxy group attached to the carbon adjacent to the uracil ring), it is produced by several species of freshwater cyanobacteria, such as Cylindrospermopsis raciborskii.
Last Modified29 September 2015
SubmitterSteve
DownloadsMolfile
FormulaC15H21N5O6S
Net Charge0
Average Mass399.429
Monoisotopic Mass399.12125
SMILES[H][C@]1(Cc2cc(=O)nc(=O)n2)C[C@@]2([H])C[C@H](OS(=O)(=O)O)[C@H](C)[C@@]3([H])CN=C(N1)N23
InChIInChI=1S/C15H21N5O6S/c1-7-11-6-16-14-17-8(2-9-4-13(21)19-15(22)18-9)3-10(20(11)14)5-12(7)26-27(23,24)25/h4,7-8,10-12H,2-3,5-6H2,1H3,(H,16,17)(H,23,24,25)(H2,18,19,21,22)/t7-,8+,10+,11-,12+/m1/s1
InChIKeyUQRKOHUZCZBNCN-GATYQTQLSA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Cylindrospermopsis raciborskii (ncbitaxon:77022) - PubMed (11223086)
Roles Classification
Biological Roles:
protein synthesis inhibitor  A compound, usually an anti-bacterial agent or a toxin, which inhibits the synthesis of a protein.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
ChEBI Ontology
Outgoing Relation(s)
deoxycylindrospermopsin (CHEBI:88050) has role protein synthesis inhibitor (CHEBI:48001)
deoxycylindrospermopsin (CHEBI:88050) is a alkaloid (CHEBI:22315)
deoxycylindrospermopsin (CHEBI:88050) is a cylindrospermopsins (CHEBI:88045)
deoxycylindrospermopsin (CHEBI:88050) is a organic sulfate (CHEBI:25704)
deoxycylindrospermopsin (CHEBI:88050) is a pyrimidone (CHEBI:38337)
deoxycylindrospermopsin (CHEBI:88050) is a triazaacenaphthylene (CHEBI:88047)
deoxycylindrospermopsin (CHEBI:88050) is tautomer of deoxycylindrospermopsin zwitterion (CHEBI:143706)
Incoming Relation(s)
deoxycylindrospermopsin zwitterion (CHEBI:143706) is tautomer of deoxycylindrospermopsin (CHEBI:88050)
IUPAC Name 
(2aS,3R,4S,5aS,7R)-7-[(2,6-dioxo-1,2,3,6-tetrahydropyrimidin-4-yl)(hydroxy)methyl]-3-methyl-2a,3,4,5,5a,6,7,8-octahydro-2H-1,8,8b-triazaacenaphthylen-4-yl hydrogen sulfate
Synonym  Source
7-deoxycylindrospermopsinChEBI
Manual XrefsDatabases
CylindrospermopsinWikipedia
Citations