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
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Physico-chemical Properties
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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
SMILES / InChI / InChIKey
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Canonical SMILES CC(=C)C1CCC2(C1C1CCC3C(C1(C)CC2)(C)CCC1C3(C)CCC(C1(C)C)O)C
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
InChI Key MQYXUWHLBZFQQO-HQBMYVNCSA-N
Classification Click here for help
Compound class Synthetic organic
IUPAC Name Click here for help
(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 Click here for help
Fagarasterol | Lupeol
Database Links Click here for help
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