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CHEBI:65416 - aplysiallene

Default Structure
ChEBI IDCHEBI:65416
ChEBI Nameaplysiallene
Stars
DefinitionA furofuran that is hexahydrofuro[3,2-b]furan which is substituted at position 2 by a (1E,3E)-4-bromohexa-1,3-dien-1-yl group and at position 5 by a (1R)-3-bromopropadienyl group (the 2R,3aS,5R,6aS diastereoisomer). A natural product first isolated from the red alga Laurencia okamurai Yamada and subsequently found in the sea hare Aplysia kurodai, aplysiallene is an inhibitor of sodium-potassium adenosine triphosphatase.
Last Modified13 November 2012
DownloadsMolfile
FormulaC15H18Br2O2
Net Charge0
Average Mass390.115
Monoisotopic Mass387.96735
SMILES[H]C(Br)=C=C([H])[C@@]1([H])C[C@]2([H])O[C@@]([H])(/C=C/C=C(/Br)CC)C[C@]2([H])O1
InChIInChI=1S/C15H18Br2O2/c1-2-11(17)5-3-6-12-9-14-15(18-12)10-13(19-14)7-4-8-16/h3,5-8,12-15H,2,9-10H2,1H3/b6-3+,11-5+/t4-,12-,13-,14-,15-/m0/s1
InChIKeyUEQYOOYTFGFGQB-BTWUOVCESA-N
Species of MetaboliteComponentSourceComments
Aplysia kurodai (ncbitaxon:6501) - PubMed (11302194)
Roles Classification
Biological Roles:
EC 3.6.3.9 (Na(+)/K(+)-transporting ATPase) inhibitor  An EC 3.6.3.* (acid anhydride hydrolase catalysing transmembrane movement of substances) inhibitor that interferes with the action of Na+/K+-transporting ATPase (EC 3.6.3.9).
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)
aplysiallene (CHEBI:65416) has role EC 3.6.3.9 (Na+/K+-transporting ATPase) inhibitor (CHEBI:63510)
aplysiallene (CHEBI:65416) has role metabolite (CHEBI:25212)
aplysiallene (CHEBI:65416) is a allenes (CHEBI:37602)
aplysiallene (CHEBI:65416) is a furofuran (CHEBI:47790)
aplysiallene (CHEBI:65416) is a organobromine compound (CHEBI:37141)
IUPAC Name 
(1R,6R)-1,4:3,6-dianhydro-1-[(1E,3E)-4-bromohexa-1,3-dien-1-yl]-6-[(1R)-3-bromopropadienyl]-2,5-dideoxy-L-threo-hexitol
Synonyms  Source
(2R,3aS,5R,6aS)-2-[(1E,3E)-4-bromohexa-1,3-dien-1-yl]-5-[(1R)-3-bromopropadienyl]hexahydrofuro[3,2-b]furanIUPAC
(−)-aplysialleneChEBI
Registry NumbersSources
Reaxys:11183914Reaxys
Citations