Molecule ID: 5276375

IUPAC Name: (4S,4aR,5S,7R,8R,8aS)-2,5,8-trihydroxy-4-[(Z)-3-hydroxyprop-2-enoyl]-4,7-dimethyl-3-[(2R)-octan-2-yl]-4a,5,6,7,8,8a-hexahydronaphthalen-1-one

Description: The molecule is a carbobicyclic compound that is 4a,5,6,7,8,8a-hexahydronaphthalen-1(4H)-one substituted by hydroxy groups at positions 2, 5 and 8, a (2Z)-3-hydroxyprop-2-enoyl group at position 4, methyl groups at positions 4 and 7 and a 2R-octan-2-yl group at position 3 (the 4S,4aR,5S,7R,8R,8aS stereoisomer). It is isolated from the fermentation extracts of Sporormiella australis and exhibits antifungal activity by interfering with the fungal lipid metabolism. It has a role as a metabolite, an EC 2.3.1.24 (sphingosine N-acyltransferase) inhibitor, a HIV-1 integrase inhibitor and an antifungal agent. It is an enol, an enone, a secondary alcohol and a carbobicyclic compound.

SMILES: CCCCCC[C@@H](C)C1=C(O)C(=O)[C@@H]2[C@H](O)[C@H](C)C[C@H](O)[C@H]2[C@]1(C)C(=O)/C=C\O

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

InChI: InChI=1S/C23H36O6/c1-5-6-7-8-9-13(2)18-22(29)21(28)17-19(15(25)12-14(3)20(17)27)23(18,4)16(26)10-11-24/h10-11,13-15,17,19-20,24-25,27,29H,5-9,12H2,1-4H3/b11-10-/t13-,14-,15+,17+,19-,20-,23-/m1/s1

Molecular Properties:
- Polar Surface Area: 115.0 Ų
- LogP: 3.9