Molecule ID: 121596210

IUPAC Name: (1R,5S,6R)-5-hydroxy-4-methoxy-1-[(2E,6E)-3,7,11-trimethyldodeca-2,6,10-trienyl]-7-oxabicyclo[4.1.0]hept-3-en-2-one

Description: The molecule is a class II yanuthone that is 5,6-epoxy-cyclohex-2-en-1-one which is substituted at positions 3, 4, and 6 by methoxy, hydroxy, and trans,trans-farnesyl groups, respectively (the 4S,5R,6R stereoisomer). Isolated from the filamentous fungus Aspergillus niger, it shows antifungal activity towards the pathogenic yeast Candida albicans (IC50 = 51.7 +-4.7 muM). It has a role as an Aspergillus metabolite and an antifungal agent. It is a class II yanuthone, an enol ether and a secondary alcohol. It derives from a (2-trans,6-trans)-farnesol.

SMILES: COC1=CC(=O)[C@]2(C/C=C(\C)CC/C=C(\C)CCC=C(C)C)O[C@@H]2[C@@H]1O

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

InChI: InChI=1S/C22H32O4/c1-15(2)8-6-9-16(3)10-7-11-17(4)12-13-22-19(23)14-18(25-5)20(24)21(22)26-22/h8,10,12,14,20-21,24H,6-7,9,11,13H2,1-5H3/b16-10+,17-12+/t20-,21-,22+/m1/s1

Molecular Properties:
- Polar Surface Area: 59.1 Ų
- LogP: 4.4