3beta-Hydroxy-20(29)-lupene   Click here for help

GtoPdb Ligand ID: 9028

Synonyms: Fagarasterol | Lupeol
Immunopharmacology Ligand
Compound class: Synthetic organic
Comment: Oral administration of Lupeol to dextran sulfate sodium (DSS)-induced colitis mice reduced intestinal inflammation and increased survival. This was associated with decreased expression of M1-related genes and increased expression of M2-related genes. Lupeol ameliorates experimental inflammatory bowel disease, at least in part, through inhibiting M1 and promoting M2 macrophages [2]. Similar results were simultaneously published in a different journal [1]. Note there are many isomers of this structure that can be found using the "same connectivity" operator in the PubChem CID entry.
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 1
Hydrogen bond donors 1
Rotatable bonds 1
Topological polar surface area 20.23
Molecular weight 426.39
XLogP 11.9
No. Lipinski's rules broken 1
Click here for help
Isomeric SMILES CC(=C)C1CCC2([C@H]1C1CCC3C([C@]1(C)CC2)(C)CC[C@@H]1C3(C)CCC(C1(C)C)O)C
InChI InChI=1S/C30H50O/c1-19(2)20-11-14-27(5)17-18-29(7)21(25(20)27)9-10-23-28(6)15-13-24(31)26(3,4)22(28)12-16-30(23,29)8/h20-25,31H,1,9-18H2,2-8H3/t20?,21?,22-,23?,24?,25+,27?,28?,29+,30?/m0/s1
Bioactivity Comments
No direct binding targets were identified but the authors propose that Lupeol acts through a specific receptor and down-stream signaling pathways, such as p38 MAPK, inhibits IRF5 and possibly other transcription factors critical for M1 polarization, resulting in decreased expression of M1 genes and enhanced expression of M2 genes, thereby causing an M1 to M2 switch [2].