Molecule ID: 102357824

IUPAC Name: 2-[(1R,2S,5S,9R,12S,16R)-1,5,12-trimethyl-11-oxo-10-oxatetracyclo[7.6.1.02,7.012,16]hexadec-7-en-5-yl]ethyl hydrogen sulfate

Description: The molecule is an organic heterotetracyclic compound that is isopimarane in which a hydrogen at position 2 of the 13-ethyl substituent has been replaced by a (sulfooxy) group, a double bond has been introduced at the 7-8 position, and the beta-methyl group at position 4 has been oxidised to the corrsponding carboxy group and coupled to position 6 to give a gamma-lactone. Isolated from an avendophytic fungus, Xylaria sp. YM 311647, obtained from Azadirachta indica, it shows potent inhibitory activity against C. albicans and Pyricularia oryzae. It has a role as an antifungal agent and a fungal metabolite. It is a diterpene, a gamma-lactone, an organic sulfate, an organic heterotetracyclic compound and an isopimarane diterpenoid.

SMILES: C[C@]1(CCOS(=O)(=O)O)CC[C@H]2C(=C[C@H]3OC(=O)[C@@]4(C)CCC[C@@]2(C)[C@@H]34)C1

SELFIES: [C][C@][Branch1][N][C][C][O][S][=Branch1][C][=O][=Branch1][C][=O][O][C][C][C@H1][C][=Branch2][Ring1][#Branch2][=C][C@H1][O][C][=Branch1][C][=O][C@@][Branch1][C][C][C][C][C][C@@][Ring1][=N][Branch1][C][C][C@@H1][Ring1][N][Ring1][Branch2][C][Ring2][Ring1][#Branch2]

InChI: InChI=1S/C20H30O6S/c1-18(9-10-25-27(22,23)24)8-5-14-13(12-18)11-15-16-19(14,2)6-4-7-20(16,3)17(21)26-15/h11,14-16H,4-10,12H2,1-3H3,(H,22,23,24)/t14-,15+,16+,18+,19+,20-/m0/s1

Molecular Properties:
- Polar Surface Area: 98.3 Ų
- LogP: 3.5