5-hydroxy-4-{6-hydroxy-5-[4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl}-2,5-dihydrofuran-2-one

• ChemBase ID: 105164
• Molecular Formular: C25H36O5
• Molecular Mass: 416.55034
• Monoisotopic Mass: 416.25627425
• SMILES: C/C(=C\CCC1=CCC(OC1O)C1=CC(=O)OC1O)/CCC1=C(C)CCCC1(C)C
• Canonical SMILES: C/C(=C\CCC1=CCC(OC1O)C1=CC(=O)OC1O)/CCC1=C(C)CCCC1(C)C
• 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
• InChIKey: FGJIDQWRRLDGDB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-hydroxy-4-{6-hydroxy-5-[4-methyl-6-(2,6,6-trimethylcyclohex-1-en-1-yl)hex-3-en-1-yl]-3,6-dihydro-2H-pyran-2-yl}-2,5-dihydrofuran-2-one
• IUPAC Traditional name: manoalide
• Synonyms: MANOALIDE

Database IDs

• CAS Number: 75088-80-1
• PubChem SID: 162091948
• PubChem CID: 5942250

CALCULATED PROPERTIES

• Acid pKa: 5.449862
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 4.609973
• LogD (pH = 7.4): 2.994391
• Log P: 4.936632
• Molar Refractivity: 119.4826 cm^3
• Polarizability: 46.31746 Å^3
• Polar Surface Area: 75.99 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• Storage Condition: -20°C

Product Information

• Purity: ≥95%

DETAILS

MP Biomedicals - 02158951

From Luffariella variabilis
Purity: >95%
Phospholipase A₂ and C inhibitor. Also blocks the release of arachidonate and inhibits calcium channels.

REFERENCES

• Jacobson, P.B., et al., Biochem. Pharmacol. , 39 : 1557, (1990).
• Wheeler, L.A., et al., J. Biol. Chem. , 262 : 6531, (1987).
• Glaser, K.B. and Jacobs, R.S., ibid. , 36 : 2079, (1987).
• Lombardo, D. and Dennis, E.A., J. Biol. Chem. , 260 : 7234, (1985).
• Mayer, A.M.S., et al., J. Pharm. Exp. Ther. , 244 : 871, (1988).
• Bennertt, C., et al., Pharmacologist , 28 : 538, (1986)