Manoalide
{{chembox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 383787917
| ImageFile=Manoalide.svg
| ImageSize=
| PIN=(5R)-5-Hydroxy-4-
| OtherNames=
|Section1={{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|??}}
| CASNo=75088-80-1
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = E1DK0157K9
| PubChem= 6437368
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 66666
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 463914
| KEGG_Ref = {{keggcite|changed|kegg}}
| KEGG = C17156
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 4941932
| 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
| InChI = 1/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-CPIXEKRIBK
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 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
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = FGJIDQWRRLDGDB-CPIXEKRISA-N
}}
|Section2={{Chembox Properties
| Formula=C25H36O5
| MolarMass=416.55034
| Appearance=
| Density=
| MeltingPt=
| BoilingPt=
| Solubility=
}}
|Section3={{Chembox Hazards
| MainHazards=
| FlashPt=
| AutoignitionPt =
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}}
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.Brusca, Richard C. and Brusca, Gary J. Invertebrates. 2nd ed. Sinauer Associates, 2002. p. 202.
Its functions are made possible by the permanent blockage of phospholipase A2 and C{{Cite book|url=https://www.worldcat.org/oclc/743217704|title=Oxford dictionary of biochemistry and molecular biology|date=2006|publisher=Oxford University Press|others=Cammack, Richard, Ph. D.|isbn=978-1-61344-113-8|edition=Rev.|location=Oxford|oclc=743217704}} 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. {{Cite journal|date=2020-12-01|title=Molecular Pharmacology: 98 (6)|url=https://molpharm.aspetjournals.org/content/98/6|journal=Molecular Pharmacology|language=en|volume=98|issue=6|issn=0026-895X}} Due to its potential of permanent inhibition, it was made possible for it to take part in oral cancer{{Cite journal|last1=Wang|first1=Hui-Ru|last2=Tang|first2=Jen-Yang|last3=Wang|first3=Yen-Yun|last4=Farooqi|first4=Ammad Ahmad|last5=Yen|first5=Ching-Yu|last6=F. Yuan|first6=Shyng-Shiou|last7=Huang|first7=Hurng-Wern|last8=Chang|first8=Hsueh-Wei|date=2019|title=Manoalide Preferentially Provides Antiproliferation of Oral Cancer Cells by Oxidative Stress-Mediated Apoptosis and DNA Damage|journal= Cancers|volume=11|issue=9|page=1303|doi=10.3390/cancers11091303|pmid=31487907|pmc=6770486|doi-access=free}} and hepatitis C{{Cite journal|last1=Salam|first1=Kazi Abdus|last2=Furuta|first2=Atsushi|last3=Noda|first3=Naohiro|last4=Tsuneda|first4=Satoshi|last5=Sekiguchi|first5=Yuji|last6=Yamashita|first6=Atsuya|last7=Moriishi|first7=Kohji|last8=Nakakoshi|first8=Masamichi|last9=Tsubuki|first9=Masayoshi|last10=Tani|first10=Hidenori|last11=Tanaka|first11=Junichi|date=2012|title=Inhibition of Hepatitis C Virus NS3 Helicase by Manoalide|journal=Journal of Natural Products|volume=75|issue=4|pages=650–4|doi=10.1021/np200883s|pmid=22394195}} research.