CHEBI:65416 - aplysiallene

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ChEBI Name aplysiallene
ChEBI ID CHEBI:65416
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C15H18Br2O2
Net Charge 0
Average Mass 390.11000
Monoisotopic Mass 387.96736
InChI InChI=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
InChIKey UEQYOOYTFGFGQB-BTWUOVCESA-N
SMILES [H]C(Br)=C=C([H])[C@@]1([H])C[C@]2([H])O[C@]([H])(C[C@]2([H])O1)\C=C\C=C(\Br)CC
Metabolite of Species Details
Aplysia kurodai (NCBI:txid6501) See: PubMed
Roles Classification
Biological Role(s): 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.
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ChEBI Ontology
Outgoing 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 Sources
(−)-aplysiallene ChEBI
(2R,3aS,5R,6aS)-2-[(1E,3E)-4-bromohexa-1,3-dien-1-yl]-5-[(1R)-3-bromopropadienyl]hexahydrofuro[3,2-b]furan IUPAC
Registry Number Type Source
11183914 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
11302194 PubMed citation Europe PMC
17691801 PubMed citation Europe PMC
Last Modified
13 November 2012
General Comment
2012-11-13 Aplysiallene was first isolated from the red alga Laurencia okamurai Yamada by Minoru Suzuki and Etsuro Kurosawa of Hokkaido University, Japan (Phytochemistry, 1985, v24(9), 1999-2002) who determined that the structure included a cis-fused 2,6-dioxabicyclo[3.3.0]octane skeleton containing an (E,E)-bromodiene side-chain and an (R)-bromoallene substituent. The same compound was subsequently isolated from the Japanese sea hare, Aplysia kurodai and named 'aplysiallene' by M. Ojika et al. (Biosci. Biotechnol. Biochem., 2001, v65(2), 474-476) but was misidentified as having only one bromine atom in the molecule, while containing an extra methyl group instead. These errors was corrected in an erratum (M. Ojika et al., Biosci. Biotechnol. Biochem., 2003, v67(2), 460) where the identity of aplysiallene to the compound reported by Suzuki and Kurosawa was confirmed. Subsequently, an elegant total synthesis of aplysiallene by Jian Wang and Brian L. Pagenkopf at the University of Western Ontario (Org. Lett., 2007, v9(18), 3703-3706) resulted in a reassignment of the stereochemistry, affording the structure shown here.