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CHEBI:66666 - manoalide

Default Structure
ChEBI IDCHEBI:66666
ChEBI Namemanoalide
Stars
DefinitionA sesterterpenoid isolated from the marine sponge Luffariella variabilis and which has been shown to exhibit inhibitory activity towards phospholipase A2.
Last Modified7 February 2018
DownloadsMolfile
FormulaC25H36O5
Net Charge0
Average Mass416.558
Monoisotopic Mass416.25627
SMILESCC1=C(CC/C(C)=C/CCC2=CC[C@H](C3=CC(=O)O[C@H]3O)O[C@H]2O)C(C)(C)CCC1
InChIInChI=1S/C25H36O5/c1-16(10-12-20-17(2)8-6-14-25(20,3)4)7-5-9-18-11-13-21(29-23(18)27)19-15-22(26)30-24(19)28/h7,11,15,21,23-24,27-28H,5-6,8-10,12-14H2,1-4H3/b16-7+/t21-,23-,24-/m1/s1
InChIKeyFGJIDQWRRLDGDB-CPIXEKRISA-N
Wikipedia
Species of MetaboliteComponentSourceComments
Luffariella variabilis (WORMS:165365) - DOI (10.1016/S0040-4039(00)77766-5)
Roles Classification
Biological Roles:
EC 5.99.1.2 (DNA topoisomerase) inhibitor  A topoisomerase inhibitor that inhibits the bacterial enzymes of the DNA topoisomerases, Type I class (EC 5.99.1.2) that catalyze ATP-independent breakage of one of the two strands of DNA, passage of the unbroken strand through the break, and rejoining of the broken strand. These bacterial enzymes reduce the topological stress in the DNA structure by relaxing negatively, but not positively, supercoiled DNA.
EC 3.1.1.4 (phospholipase A2) inhibitor  An EC 3.1.1.* (carboxylic ester hydrolase) inhibitor that interferes with the action of phospholipase A2 (EC 3.1.1.4).
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor  A topoisomerase inhibitor that inhibits DNA topoisomerase (ATP-hydrolysing), EC 5.99.1.3 (also known as topoisomerase II and as DNA gyrase), which catalyses ATP-dependent breakage of both strands of DNA, passage of the unbroken strands through the breaks, and rejoining of the broken strands.
ChEBI Ontology
Outgoing Relation(s)
manoalide (CHEBI:66666) has role EC 3.1.1.4 (phospholipase A2) inhibitor (CHEBI:50469)
manoalide (CHEBI:66666) has role EC 5.99.1.2 (DNA topoisomerase) inhibitor (CHEBI:50276)
manoalide (CHEBI:66666) has role EC 5.99.1.3 [DNA topoisomerase (ATP-hydrolysing)] inhibitor (CHEBI:50750)
manoalide (CHEBI:66666) has role metabolite (CHEBI:25212)
manoalide (CHEBI:66666) is a butenolide (CHEBI:50523)
manoalide (CHEBI:66666) is a lactol (CHEBI:38131)
manoalide (CHEBI:66666) is a sesterterpenoid (CHEBI:26660)
IUPAC Name 
(5R)-5-hydroxy-4-{(2R,6R)-6-hydroxy-5-[(3E)-4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl}furan-2(5H)-one
Manual XrefsDatabases
C17156KEGG COMPOUND
CA1297030Patent
LMPR0105020001LIPID MAPS
ManoalideWikipedia
US4839385Patent
Registry NumbersSources
Reaxys:10729444Reaxys
CAS:75088-80-1ChemIDplus
Citations