CHEBI:66666 - manoalide

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ChEBI Name manoalide
ChEBI ID CHEBI:66666
Definition A sesterterpenoid isolated from the marine sponge Luffariella variabilis and which has been shown to exhibit inhibitory activity towards phospholipase A2.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C25H36O5
Net Charge 0
Average Mass 416.55030
Monoisotopic Mass 416.256
InChI InChI=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
InChIKey FGJIDQWRRLDGDB-CPIXEKRISA-N
SMILES C\C(CCC1=C(C)CCCC1(C)C)=C/CCC1=CC[C@@H](O[C@H]1O)C1=CC(=O)O[C@H]1O
Metabolite of Species Details
Luffariella var.abilis (WORMS:165365) See: DOI
Roles Classification
Biological Role(s): metabolite
Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
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).
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 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.
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ChEBI Ontology
Outgoing 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 Xrefs Databases
C17156 KEGG COMPOUND
CA1297030 Patent
LMPR0105020001 LIPID MAPS
Manoalide Wikipedia
US4839385 Patent
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Registry Numbers Types Sources
10729444 Reaxys Registry Number Reaxys
75088-80-1 CAS Registry Number ChemIDplus
Citations Waiting for Citations Types Sources
10101221 PubMed citation Europe PMC
10437157 PubMed citation Europe PMC
22394195 PubMed citation Europe PMC
25584012 PubMed citation Europe PMC
2586492 PubMed citation Europe PMC
3997864 PubMed citation Europe PMC
8149454 PubMed citation Europe PMC
Last Modified
07 February 2018