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CHEBI:65416 - aplysiallene

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:
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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).
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
(−)-aplysialleneChEBI
(2R,3aS,5R,6aS)-2-[(1E,3E)-4-bromohexa-1,3-dien-1-yl]-5-[(1R)-3-bromopropadienyl]hexahydrofuro[3,2-b]furanIUPAC
Registry NumbersSources
Reaxys:11183914Reaxys
Citations