dysiherbaine (CHEBI:197431)

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ChEBI Name	dysiherbaine

ChEBI ID	CHEBI:197431

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

Submitter	sbalu

Supplier Information

Download	Molfile XML SDF

Formula

C12H20N2O7

Net Charge

Average Mass

304.299

Monoisotopic Mass

304.12705

InChI

InChI=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

InChIKey

YUSZFKPLFIQTGF-FDNSHYBFSA-N

SMILES

[H][C@@]12C[C@@](C[C@H](N)C(O)=O)(O[C@]1([H])[C@H](NC)[C@H](O)CO2)C(O)=O

Metabolite of Species	Details
Dysidea herbacea (WORMS:220470)	See: DOI

Roles Classification
Chemical Role(s):	Bronsted base A molecular entity capable of accepting a hydron from a donor (Bronsted acid). (via organic amino compound ) Bronsted acid A molecular entity capable of donating a hydron to an acceptor (Bronsted base). (via oxoacid )

Biological Role(s):	excitatory amino acid agonist An agent that binds to and activates excitatory amino acid receptors. 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.

Application(s):	excitatory amino acid agonist An agent that binds to and activates excitatory amino acid receptors.

ChEBI Ontology
Outgoing	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
(−)-dysiherbaine	ChEBI

Registry Number	Type	Source
185245-55-0	CAS Registry Number	SUBMITTER

Last Modified

17 October 2023