Structure Database (LMSD)

Common Name
Gentiopicrin
Systematic Name
Synonyms
LM ID
LMPR0102070009
Formula
Exact Mass
Calculate m/z
356.110735
Status
Curated



Classification

Biological Context

Gentiopicrin is an iridoid glycoside that has been found in G. rigescens and has diverse biological activities.1,2,3 In vivo, gentiopicrin (130 mg/kg) attenuates acute cholestasis and liver damage and reverses bile acid dyshomeostasis induced by α-napthylisothiocyanate (ANIT) in mice.1 It increases the paw withdrawal threshold in the cold-plate test and latency to paw withdrawal in the plantar test in mice when administered at doses of 25, 50, and 100 mg/kg.2 Gentiopicrin (100 mg/kg) also decreases NMDA receptor-mediated excitatory postsynaptic currents (EPSCs) in the nucleus accumbens and reverses morphine-induced conditioned place preference in mice.3

This information has been provided by Cayman Chemical

References

String Representations

InChiKey (Click to copy)
DUAGQYUORDTXOR-GPQRQXLASA-N
InChi (Click to copy)
InChI=1S/C16H20O9/c1-2-7-8-3-4-22-14(21)9(8)6-23-15(7)25-16-13(20)12(19)11(18)10(5-17)24-16/h2-3,6-7,10-13,15-20H,1,4-5H2/t7-,10-,11-,12+,13-,15+,16+/m1/s1
SMILES (Click to copy)
O([C@@H]1OC=C2C(=O)OCC=C2[C@H]1C=C)[C@H]1[C@H](O)[C@H]([C@H](O)[C@@H](CO)O1)O

Other Databases

KEGG ID
CHEBI ID
PubChem CID
Cayman ID

Calculated Physicochemical Properties

Heavy Atoms 25
Rings 3
Aromatic Rings 0
Rotatable Bonds 4
Van der Waals Molecular Volume 316.83
Topological Polar Surface Area 141.12
Hydrogen Bond Donors 4
Hydrogen Bond Acceptors 9
logP 0.62
Molar Refractivity 84.59

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Updated at
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