Structure Database (LMSD)
Common Name
Harpagoside
Systematic Name
Synonyms
3D model of Harpagoside
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
Harpagoside is an iridoid glycoside that has been found in H. procumbens, also known as devil’s claw, and has diverse biological activities.1,2,3 It inhibits LPS-induced increases in COX-2 and nitric oxide (NO) levels, as well as TNF mRNA expression in HepG2 cells when used at concentrations ranging from 50 to 200 µM.1 In vivo, harpagoside (10 mg/kg) reduces synovial inflammation, joint destruction, and bone erosion in a mouse model of collagen-induced arthritis.2 It also decreases substantia nigra pars compacta neuronal cell death and increases time spent on the rod in a rotarod test in a mouse model of MPTP-induced Parkinson’s disease.3
This information has been provided by Cayman Chemical
References
References
String Representations
InChiKey (Click to copy)
KVRQGMOSZKPBNS-FMHLWDFHSA-N
InChi (Click to copy)
InChI=1S/C24H30O11/c1-23(35-16(27)8-7-13-5-3-2-4-6-13)11-15(26)24(31)9-10-32-22(20(23)24)34-21-19(30)18(29)17(28)14(12-25)33-21/h2-10,14-15,17-22,25-26,28-31H,11-12H2,1H3/b8-7+/t14-,15-,17-,18+,19-,20-,21+,22+,23+,24-/m1/s1
SMILES (Click to copy)
O([C@@H]1OC=C[C@@]2(O)[C@@H](C[C@](C)(OC(=O)/C=C/C3C=CC=CC=3)[C@]21[H])O)[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O
Other Databases
Calculated Physicochemical Properties
Heavy Atoms
35
Rings
4
Aromatic Rings
1
Rotatable Bonds
7
Van der Waals Molecular Volume
444.27
Topological Polar Surface Area
179.51
Hydrogen Bond Donors
6
Hydrogen Bond Acceptors
11
logP
1.66
Molar Refractivity
123.00
Admin
Created at
-
Updated at
7th Mar 2024