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

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

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Updated at
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