Manoalide

Manoalide

Names
Preferred 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
Identifiers
CAS Number	75088-80-1 Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:66666 N
ChEMBL	ChEMBL463914 N
ChemSpider	4941932 N
KEGG	C17156 N
PubChem CID	6437368
UNII	E1DK0157K9 Y
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 N Key: FGJIDQWRRLDGDB-CPIXEKRISA-N N 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 Key: FGJIDQWRRLDGDB-CPIXEKRIBK
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
Properties
Chemical formula	C25H36O5
Molar mass	416.55034
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

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.^[1] Its functions are made possible by the permanent blockage of phospholipase A2 and C^[2] 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. ^[3] Due to its potential of permanent inhibition, it was made possible for it to take part in oral cancer^[4] and Hepatitis C^[5] research.

References

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