Structure Database (LMSD)
Common Name
Lupeol
Systematic Name
Synonyms
3D model of Lupeol
Please note: Where there are chiral atoms but the stereochemistry is undefined, the 3D model takes an arbitrary conformation
Classification
Category
Main Class
Sub Class
Level 4 Class
Biological Context
Lupeol, a dietary triterpene found in certain fruits, vegetables, and medicinal plants, has potent anti-inflammatory, anticarcinogenic, antimutagenic, and antimalarial activity. It suppresses the growth of hepatocellular carcinoma cell lines SMMC7721 and HepG2 with IC50 values of 45 and 48.5 μM and melanoma cell lines Mel 928 and Mel 1241 with IC50 values of 75 and 72 μM.1,2 At 0.76 g/kg lupeol causes a significant decrease in the blood pressure of stroke-prone hypertensive rats and reduces expression of hepatic genes involved in triglyceride and cholesterol synthesis.3 It also has significant anti-inflammatory effects at 50 mg/kg in a carrageenan-induced edema model, inhibiting neutrophil migration.4
This information has been provided by Cayman Chemical
References
1. Tarapore, R.S., Siddiqui, I.A., Saleem, M., et al. Specific targeting of Wnt/β-catenin signaling in human melanoma cells by a dietary triterpene lupeol. Carcinogenesis 31(10), 1844-1853 (2010).
3. He, Y., Liu, F., Zhang, L., et al. Growth inhibition and apoptosis induced by lupeol, a dietary triterpene, in human hepatocellular carcinoma cells. Bio. Pharm. Bull. 34(4), 517-522 (2011).
4. Lucetti, D.L., Lucetti, E.C., Bandeira, M.A., et al. Anti-inflammatory effects and possible mechanism of action of lupeol acetate isolated from Himatanthus drasticus (Mart.) Plumel. J. Inflamm. (Lond.) 7(60), 1-11 (2010).
String Representations
InChiKey (Click to copy)
MQYXUWHLBZFQQO-QGTGJCAVSA-N
InChi (Click to copy)
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
SMILES (Click to copy)
[C@@]12(C)CC[C@@]3(C)CC[C@@]([H])(C(=C)C)[C@]3([H])[C@@]1([H])CC[C@]1([H])[C@@]3(C)CC[C@H](O)C(C)(C)[C@]3([H])CC[C@@]21C
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
31
Rings
5
Aromatic Rings
0
Rotatable Bonds
1
Van der Waals Molecular Volume
471.91
Topological Polar Surface Area
20.23
Hydrogen Bond Donors
1
Hydrogen Bond Acceptors
1
logP
8.31
Molar Refractivity
131.16
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Created at
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Updated at
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