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
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.
Database Links
GtoPdb PubChem SID 315661113
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