3beta-Hydroxy-20(29)-lupene

Ligand id: 9028

Name: 3beta-Hydroxy-20(29)-lupene

Structure and Physico-chemical Properties

2D Structure
Calculated Physico-chemical Properties
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

Molecular properties generated using the CDK

Classification
Compound class Synthetic organic
IUPAC Name
(5aR,7aR,13bR)-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-1,2,3,4,5,6,7,7a,9,10,11,11b,12,13,13a,13b-hexadecahydrocyclopenta[a]chrysen-9-ol
Synonyms
Fagarasterol | Lupeol
Database Links
PubChem CID 16219576
Search Google for chemical match using the InChIKey MQYXUWHLBZFQQO-HQBMYVNCSA-N
Search Google for chemicals with the same backbone MQYXUWHLBZFQQO
Search UniChem for chemical match using the InChIKey MQYXUWHLBZFQQO-HQBMYVNCSA-N
Search UniChem for chemicals with the same backbone MQYXUWHLBZFQQO
Wikipedia https://en.wikipedia.org/wiki/Lupeol
Comments
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.