Structure Database (LMSD)
Common Name
Verbenalin
Systematic Name
Synonyms
3D model of Verbenalin
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
Verbenalin is an iridoid glucoside that has been found in V. officinalis and has diverse biological activities.1,2,3 It inhibits the activities of COX-1 and COX-2 by 37 and 48%, respectively, when used at a concentration of 258 µM.2 Verbenalin (129 µM) inhibits proliferation of AGS gastric, SF-268 CNS, HCT116 colon, NCI H460 lung, and MCF-7 breast cancer cells. It reduces carrageenan-induced paw edema, as well as ear edema induced by phorbol 12-myristate 13-acetate (TPA), in mice.3 Verbenalin (5 and 10 mg/kg) reduces increases in malondialdehyde (MDA) levels and the production of reactive oxygen species (ROS) in brain mitochondria isolated from, as well as decreases infarct volume and neurological deficits in, a rat model of ischemia-reperfusion injury induced by middle cerebral artery occlusion (MCAO).1
This information has been provided by Cayman Chemical
References
3. Recio, M.d.C., Giner, R.M., Máñez, S., et al. Structural considerations on the iridoids as anti-inflammatory agents. Planta Med. 60(3), 232-234 (1994).
String Representations
InChiKey (Click to copy)
HLXRWTJXGMHOFN-XJSNKYLASA-N
InChi (Click to copy)
InChI=1S/C17H24O10/c1-6-3-8(19)11-7(15(23)24-2)5-25-16(10(6)11)27-17-14(22)13(21)12(20)9(4-18)26-17/h5-6,9-14,16-18,20-22H,3-4H2,1-2H3/t6-,9+,10+,11-,12+,13-,14+,16-,17-/m0/s1
SMILES (Click to copy)
O([C@@H]1OC=C(C(=O)OC)[C@@]2([H])C(C[C@H](C)[C@]21[H])=O)[C@H]1[C@H](O)[C@H]([C@H](O)[C@H](O1)CO)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
27
Rings
3
Aromatic Rings
0
Rotatable Bonds
5
Van der Waals Molecular Volume
345.56
Topological Polar Surface Area
156.12
Hydrogen Bond Donors
4
Hydrogen Bond Acceptors
10
logP
0.06
Molar Refractivity
89.15
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Updated at
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