Structure Database (LMSD)

Common Name
Harpagoside
Systematic Name
Synonyms
LM ID
LMPR0102070010
Formula
Exact Mass
Calculate m/z
494.178816
Status
Curated



Classification

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

Taxonomy Information

Curated from
NCBI taxonomy class
Reference
Harpagophytum procumbens (#222879)
Magnoliopsida (#3398)
Die Struktur des Harpagosids. 2. Mitteilung über Iridoide,
Helv Chim Acta, 1966

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

Wikipedia
KEGG ID
CHEBI ID
PubChem CID
Cayman ID

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

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Created at
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Updated at
7th Mar 2024