Molecule ID: 53355241

IUPAC Name: [(8R,9S,10R,13R,14S,17R)-17-[(1S,2S)-1-[(2R,3R,4R)-3,4-dimethyl-5-oxooxolan-2-yl]-1-hydroxypropan-2-yl]-10-methyl-3-oxo-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-13-yl]methyl acetate

Description: The molecule is a withanolide that is 23,26-epoxyergosta-1,4-diene substituted by an acetyloxy group at position 18, a hydroxy group at position 22 and oxo groups at positions 3 and 26. Isolated from a Formosan soft coral Paraminabea acronocephala, it has been found to inhibit the accumulation of the pro-inflammatory iNOS protein. It has a role as an EC 1.14.13.39 (nitric oxide synthase) inhibitor and a coral metabolite. It is a gamma-lactone, an acetate ester, an ergostanoid, a withanolide, a secondary alcohol, a steroid ester and a 3-oxo-Delta(1),Delta(4)-steroid.

SMILES: CC(=O)OC[C@]12CC[C@H]3[C@@H](CCC4=CC(=O)C=C[C@@]43C)[C@@H]1CC[C@@H]2[C@H](C)[C@H](O)[C@@H]1OC(=O)[C@H](C)[C@H]1C

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

InChI: InChI=1S/C30H42O6/c1-16-17(2)28(34)36-27(16)26(33)18(3)23-8-9-25-22-7-6-20-14-21(32)10-12-29(20,5)24(22)11-13-30(23,25)15-35-19(4)31/h10,12,14,16-18,22-27,33H,6-9,11,13,15H2,1-5H3/t16-,17-,18+,22-,23-,24+,25+,26+,27-,29+,30+/m1/s1

Molecular Properties:
- Polar Surface Area: 89.9 Ų
- LogP: 5.3