Structure Database (LMSD)

Common Name
Verbenalin
Systematic Name
Synonyms
LM ID
LMPR0102070016
Formula
Exact Mass
Calculate m/z
388.13695
Status
Curated


Classification

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

KEGG ID
CHEBI ID
PubChem CID
Cayman ID

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

Admin

Created at
-
Updated at
-