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CHEBI:197431 - dysiherbaine

Default Structure
ChEBI IDCHEBI:197431
ChEBI Namedysiherbaine
Stars
DefinitionA furopyran that is (3aR,7aR)-hexahydro-2H-furo[3,2-b]pyran substituted by carboxy, (2S)-2-amino-2-carboxyethyl, hydroxy and methylamino groups at positions 2, 2, 6, and 7, respectively (the 2R,3aR,6S,7R,7aR-stereoisomer). A convulsant isolated from the marine sponge Dysidea herbacea that has high affinity for kainate ionotropic glutamate receptors.
Last Modified17 October 2023
Submittersbalu
DownloadsMolfile
FormulaC12H20N2O7
Net Charge0
Average Mass304.299
Monoisotopic Mass304.12705
SMILES[H][C@@]12C[C@](C[C@H](N)C(=O)O)(C(=O)O)O[C@]1([H])[C@H](NC)[C@H](O)CO2
InChIInChI=1S/C12H20N2O7/c1-14-8-6(15)4-20-7-3-12(11(18)19,21-9(7)8)2-5(13)10(16)17/h5-9,14-15H,2-4,13H2,1H3,(H,16,17)(H,18,19)/t5-,6+,7+,8+,9-,12+/m0/s1
InChIKeyYUSZFKPLFIQTGF-FDNSHYBFSA-N
Species of MetaboliteComponentSourceComments
Dysidea herbacea (WORMS:220470) - DOI (10.1021/ja963953z)
Roles Classification
Chemical Roles:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
animal metabolite  Any eukaryotic metabolite produced during a metabolic reaction in animals that include diverse creatures from sponges, insects to mammals.
marine metabolite  Any metabolite produced during a metabolic reaction in marine macro- and microorganisms.
neurotoxin  A poison that interferes with the functions of the nervous system.
excitatory amino acid agonist  An agent that binds to and activates excitatory amino acid receptors.
Application:
excitatory amino acid agonist  An agent that binds to and activates excitatory amino acid receptors.
ChEBI Ontology
Outgoing Relation(s)
dysiherbaine (CHEBI:197431) has role animal metabolite (CHEBI:75767)
dysiherbaine (CHEBI:197431) has role excitatory amino acid agonist (CHEBI:50103)
dysiherbaine (CHEBI:197431) has role marine metabolite (CHEBI:76507)
dysiherbaine (CHEBI:197431) has role neurotoxin (CHEBI:50910)
dysiherbaine (CHEBI:197431) is a amino dicarboxylic acid (CHEBI:36164)
dysiherbaine (CHEBI:197431) is a furopyran (CHEBI:74927)
dysiherbaine (CHEBI:197431) is a hydroxy carboxylic acid (CHEBI:24669)
dysiherbaine (CHEBI:197431) is a secondary amino compound (CHEBI:50995)
IUPAC Name 
(2R,3aR,6S,7R,7aR)-2-[(2S)-2-amino-2-carboxyethyl]-6-hydroxy-7-(methylamino)hexahydro-2H-furo[3,2-b]pyran-2-carboxylic acid
Synonym  Source
(−)-dysiherbaineChEBI
Manual XrefsDatabases
C00028227KNApSAcK
DYHPDBeChem
WO2004089956Patent
Registry NumbersSources
CAS:185245-55-0SUBMITTER
Citations