Structure Database (LMSD)
Common Name
Aucubin
Systematic Name
Synonyms
3D model of Aucubin
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
Aucubin is an iridoid glycoside that has been found in E. ulmoides with diverse biological activities.1,2 Aucubin (0.001-1 μg/ml) dose-dependently inhibits the IgE-stimulated secretion of IL-6 and TNF-α by RBL-2H3 mast cells (IC50s = 0.19 and 0.1 μg/ml, respectively).1 It reduces UVB-induced expression of matrix metalloproteinase-1 (MMP-1) in HS68 human foreskin fibroblasts by 57% when used at a concentration of 0.01 μg/ml.2 Aucubin (0.01-1 μg/ml) also dose-dependently reduces production of reactive oxygen species (ROS) and malondialdehyde (MDA) levels, a marker of lipid peroxidation. In a mouse model of pulmonary fibrosis induced by bleomycin , aucubin (5 mg/kg, i.p.) decreases the breathing frequency, increases lung dynamic compliance, alleviates parenchymal fibrotic changes, and reduces expression of TGF-β1 and α-smooth muscle actin (α-SMA).3 Aucubin (5 mg/kg, i.p.) reduces blood glucose levels and lipid peroxidation in the liver and kidneys of rats with diabetes induced by streptozotocin .4 It also reduces the number of errors made in a Y-maze and enhances neuronal survival by approximately 7- and 4-fold, respectively, in rats with streptozotocin-induced diabetes.5
This information has been provided by Cayman Chemical
References
2. Ho, J.N., Lee, Y.H., Park, J.S., et al. Protective effects of aucubin isolated from Eucommia ulmoides against UVB-induced oxidative stress in human skin fibroblasts. Biol. Pharm. Bull. 29(7), 1244-1248 (2005).
3. Zhou, Y., Li, P., Duan, J.X., et al. Aucubin alleviates bleomycin-induced pulmonary fibrosis in a mouse model. Inflammation 40(6), 2062-2073 (2017).
String Representations
InChiKey (Click to copy)
RJWJHRPNHPHBRN-FKVJWERZSA-N
InChi (Click to copy)
InChI=1S/C15H22O9/c16-4-6-3-8(18)7-1-2-22-14(10(6)7)24-15-13(21)12(20)11(19)9(5-17)23-15/h1-3,7-21H,4-5H2/t7-,8+,9+,10+,11+,12-,13+,14-,15-/m0/s1
SMILES (Click to copy)
O([C@@H]1OC=C[C@@]2([H])[C@@H](C=C([C@@]12[H])CO)O)[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
24
Rings
3
Aromatic Rings
0
Rotatable Bonds
4
Van der Waals Molecular Volume
304.81
Topological Polar Surface Area
153.21
Hydrogen Bond Donors
6
Hydrogen Bond Acceptors
9
logP
-0.23
Molar Refractivity
81.58
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Updated at
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