Structure via PubChem · Public domain (PubChem)
manoalide
Sign in to saveManoalide is a calcium channel blocker. It has antibiotic, analgesic and anti-inflammatory effects and is found in some sponges, including the West Pacific species Luffariella variabilis. Its functions are made possible by the permanent blockage of phospholipase A2 and C with lysine residues. This could be made possible through the functional groups incorporated in gamma-hydroxybutenolide, alpha-hydroxydihydropyran and the trimethylcyclohexenyl. The gamma-hydroxybutenolide ring is present in the reaction between manoalide and phospholipase A2, the hemiacetal in alpha-hydroxydihydropyran is nee
Chemical data
- Formula
- C25H36O5
- Molecular weight
- 416.5 g/mol
- IUPAC name
- (2R)-2-hydroxy-3-[(2R,6R)-6-hydroxy-5-[(E)-4-methyl-6-(2,6,6-trimethylcyclohexen-1-yl)hex-3-enyl]-3,6-dihydro-2H-pyran-2-yl]-2H-furan-5-one
- SMILES
- CC1=C(C(CCC1)(C)C)CC/C(=C/CCC2=CC[C@@H](O[C@H]2O)C3=CC(=O)O[C@H]3O)/C
- InChIKey
- FGJIDQWRRLDGDB-CPIXEKRISA-N
- XLogP
- 3.5
- Polar surface area
- 76 Ų
- H-bond donors
- 2
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
197 papers- Manoalide.Current medicinal chemistry · 1999
- Manoalide Induces Intrinsic Apoptosis by Oxidative Stress and Mitochondrial Dysfunction in Human Osteosarcoma Cells.Antioxidants (Basel, Switzerland) · 2023
- Manoalide Preferentially Provides Antiproliferation of Oral Cancer Cells by Oxidative Stress-Mediated Apoptosis and DNA Damage.Cancers · 2019
- A calcium channel blocker, manoalide exerts an anti-allergic inflammatory effect through attenuating NF-κB activity.Immunopharmacology and immunotoxicology · 2021
- Manoalide Shows Mutual Interaction between Cellular and Mitochondrial Reactive Species with Apoptosis in Oral Cancer Cells.Oxidative medicine and cellular longevity · 2021
via PubMed
Wikidata facts
- Mass
- 416.256274
Show 5 more facts
- isomeric SMILES
- CC1=C(C(CCC1)(C)C)CC/C(=C/CCC2=CC[C@@H](O[C@H]2O)C3=CC(=O)O[C@H]3O)/C
- chemical formula
- C₂₅H₃₆O₅
- canonical SMILES
- CC1=C(C(CCC1)(C)C)CCC(=CCCC2=CCC(OC2O)C3=CC(=O)OC3O)C
- found in taxon
- Spongiidae
- subject has role
- phosphodiesterase inhibitor
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
{{chembox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 383787917 | ImageFile=Manoalide.svg | ImageSize= | PIN=(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 | OtherNames= |Section1= |Section2= |Section3= }} Manoalide is a calcium channel blocker. It has antibiotic, analgesic and anti-inflammatory effects and is found in some sponges, including the West Pacific species Luffariella variabilis. Its functions are made possible by the permanent blockage of phospholipase A2 and C with lysine residues. This could be made possible through the functional groups incorporated in gamma-hydroxybutenolide, alpha-hydroxydihydropyran and the trimethylcyclohexenyl. The gamma-hydroxybutenolide ring is present in the reaction between manoalide and phospholipase A2, the hemiacetal in alpha-hydroxydihydropyran is needed for permanent binding and hydrophobic trimethylcyclohexenyl ring makes it possible for non-bonded interactions to interact between manoalide and phospholipase A2 to strengthen the reaction. Due to its potential of permanent inhibition, it was made possible for it to take part in oral cancer and hepatitis C research.
==References==
Excerpted from Wikipedia’s “manoalide” article, available under the CC BY-SA 4.0 licence.