Molecule ID: 121596209

IUPAC Name: [(1R,6R)-6-[(2E,6E)-11-hydroxy-3,7,11-trimethyldodeca-2,6-dienyl]-3-methyl-5-oxo-7-oxabicyclo[4.1.0]hept-3-en-2-yl] acetate

Description: The molecule is a class I yanuthone that is yanuthone K in which the double bond at the terminal end of the farnesyl substituent has undergone hydration to afford the corresponding tertiary alcohol. Isolated from the filamentous fungus Aspergillus niger, it shows antifungal activity towards the pathogenic yeast Candida albicans (IC50 = 77.5 +-3.7 muM). It has a role as an Aspergillus metabolite and an antifungal agent. It is an acetate ester, a class I yanuthone and a tertiary amine. It derives from a yanuthone K.

SMILES: CC(=O)OC1C(C)=CC(=O)[C@]2(C/C=C(\C)CC/C=C(\C)CCCC(C)(C)O)O[C@H]12

SELFIES: [C][C][=Branch1][C][=O][O][C][C][Branch1][C][C][=C][C][=Branch1][C][=O][C@][Branch2][Ring1][=Branch2][C][/C][=C][Branch1][C][\C][C][C][/C][=C][Branch1][C][\C][C][C][C][C][Branch1][C][C][Branch1][C][C][O][O][C@H1][Ring2][Ring1][=Branch2][Ring2][Ring1][Ring1]

InChI: InChI=1S/C24H36O5/c1-16(11-8-13-23(5,6)27)9-7-10-17(2)12-14-24-20(26)15-18(3)21(22(24)29-24)28-19(4)25/h9,12,15,21-22,27H,7-8,10-11,13-14H2,1-6H3/b16-9+,17-12+/t21?,22-,24+/m1/s1

Molecular Properties:
- Polar Surface Area: 76.1 Ų
- LogP: 3.9