CHEBI:88050 - deoxycylindrospermopsin

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ChEBI Name deoxycylindrospermopsin
ChEBI ID CHEBI:88050
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H21N5O6S
Net Charge 0
Average Mass 399.424
Monoisotopic Mass 399.12125
InChI InChI=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
InChIKey UQRKOHUZCZBNCN-GATYQTQLSA-N
SMILES [C@@]12(C[C@@H]([C@@H]([C@@]3(N1C(N[C@](C2)(CC4=CC(NC(N4)=O)=O)[H])=NC3)[H])C)OS(O)(=O)=O)[H]
Metabolite of Species Details
Cylindrospermopsis raciborskii (NCBI:txid77022) See: PubMed
Roles Classification
Biological Role(s): 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.
(via alkaloid )
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ChEBI Ontology
Outgoing 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 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-deoxycylindrospermopsin ChEBI
Manual Xref Database
Cylindrospermopsin Wikipedia
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Citations Waiting for Citations Types Sources
11223086 PubMed citation Europe PMC
11594025 PubMed citation Europe PMC
14969289 PubMed citation Europe PMC
15900531 PubMed citation Europe PMC
17763086 PubMed citation Europe PMC
22287011 PubMed citation Europe PMC
Last Modified
29 September 2015